147 results on '"Yuanqiang Guo"'
Search Results
2. Modification of a natural diterpene and its antitumor mechanism: Promoting apoptosis, suppressing migration, and inhibiting angiogenesis
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Yuhui Liu, Sibei Wang, Maoqin Peng, Jun Ma, Qi Zhang, Yuanqiang Guo, and Jing Xu
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3,4-seco-Sonderianol ,Triphenylphosphonium modification ,Mitochondrial targeting ,Apoptosis and migration ,Angiogenesis ,Chemistry ,QD1-999 - Abstract
The synthesis or derivation of a series of structural analogues based on natural products is a common strategy for discovering antitumor drugs. As a unique natural diterpene derived from Trigonostemon howii, 3,4-seco-sonderianol (1) exhibited moderate cytotoxic effects. To improve the activity, a new diterpene derivative (1b) with a mitochondrial targeting function was synthesized by coupling triphenylphosphine to compound 1. Compared to the parent molecule, the antitumor activity of 1b increased greatly. A series of mechanistic experiments revealed that compound 1b induced cancer cell apoptosis and inhibited cancer cell migration by targeting the mitochondria and regulating the STAT3 and FAK signaling pathways. Meanwhile, 1b was found to inhibit angiogenesis in a transgenic zebrafish model. It is worth noting that 1b also demonstrated excellent antitumor effects in zebrafish tumor xenotransplantation models. All the evidence supports that compound 1b targeting mitochondria has the potential to be a candidate for an antitumor drug.
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- 2024
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3. Biotin-modified hyaluronic acid double-target nanoparticles for quercetin and IR780 delivery: Fabrication, characterization, and biological properties
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Linan Zhou, Ying Li, Zhen Lin, Xiaotang Gong, Jing Xu, and Yuanqiang Guo
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Nanocarrier system ,Chemo-phototherapy combination ,IR780 ,Quercetin ,Tumor targeting ,Chemistry ,QD1-999 - Abstract
Currently, the use of nanotechnology to repurpose traditional drugs has emerged as a promising strategy for cancer treatment. Quercetin (Qu), a chemotherapy molecule, has excellent antitumor activity, and IR780, a photosensitizer, possesses sound tumor phototherapy effects. However, both compounds have poor water solubility and other drawbacks that hinder their extensive clinical applications. To effectively utilize two molecules in the fight against cancer, a new multifunctional chemical-phototherapy nanoplatform with tumor target and glutathione (GSH) response was designed. By modifying hyaluronic acid (HA), the amphiphilic molecule carrying biotin and IR780 was obtained, which self-assembled to load the antitumor active molecule Qu, namely Qu@BHSI. In addition to addressing the hydrophobic issue of Qu and IR780, the prepared nanoparticles can rapidly release Qu with high concentrations of GSH present and generate heat and cytotoxic reactive oxygen species (ROS) under near-infrared light. The biological function research showed that Qu@BHSI nanoparticles had the ability to suppress the growth of A549 cells, induce cell apoptosis, stimulate ROS production in zebrafish, and inhibit angiogenesis in transgenic zebrafish. The construction of nanosystems provides new or alternative strategies and approaches for effectively repurposing classical drug molecules including photosensitizers and chemotherapy drugs.
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- 2024
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4. Trigothysoid N inhibits tumor proliferation and migration by targeting mitochondria and the STAT3/FAK pathway
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Ying Li, Yuhui Liu, Yeling Li, Feng Liu, Yinan Zhao, Jing Xu, and Yuanqiang Guo
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Natural diterpenoid ,Anti-tumor activity ,Zebrafish xenograft model ,Mitochondria ,STAT3 ,FAK ,Chemistry ,QD1-999 - Abstract
Natural products are one of the essential sources of innovative drugs. Trigothysoid N, a natural daphnane diterpenoid obtained from Trigonostemon thyrsoideus, possessed the strong ability to inhibit the proliferation of A549 cells. Besides interrupting the cell cycle, the mechanism examination revealed that trigothysoid N can inhibit tumor proliferation and migration by targeting mitochondria, regulating the STAT3/FAK signal pathway, and suppressing angiogenesis. In addition to the possible mechanism, in vivo antitumor experiments were performed to explore the potential of trigothysoid N for treating non-small cell lung cancer (NSCLC). Collectively, these findings supported the great potential of trigothysoid N as a hopeful therapeutic agent against NSCLC.
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- 2023
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5. Characterization, selenylation, and antineoplastic effects on HepG2 cells in vitro and in vivo of an arabinofuranan from the fruits of Akebia quinata
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Huimei Wang, Zhen Lin, Ying Li, Xuelian Wang, Jing Xu, and Yuanqiang Guo
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Arabinofuranan ,Selenylation ,Akebia quinata ,HepG2 cells ,Zebrafish ,Antiangiogenic ,Chemistry ,QD1-999 - Abstract
Akebia quinata is a traditional medicinal plant distributed in East Asia and its fruits are applicated in food and pharmaceutical fields. Herein, a novel polysaccharide (AQP70-2A) with a molecular weight of 1.49 × 104 Da was isolated from the fruits of A. quinata. Results of the chemical and spectroscopic analysis indicated that AQP70-2A was an arabinofuranan with a backbone mainly consisting of → 5)-α-l-Araf-(1→, →3,5)-α-l-Araf-(1→, and → 2,3,5)-α-l-Araf-(1→, and it also contained two types of branch chains. At the cellular level, AQP70-2A did not show significant antitumor properties, while selenylation significantly made the inhibitory effect of this natural macromolecule on HepG2 cells to be increased. Furthermore, the zebrafish xenograft model confirmed that selenized polysaccharide Se-AQP70-2A effectively blocked hepatocellular carcinoma cells invasion and metastasis. Meanwhile, the inhibition of Se-AQP70-2A on development of intersegmental vessels revealed its antiangiogenic activity.
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- 2023
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6. A novel polysaccharide from Paeonia lactiflora exerts anti-tumor activity via immunoregulation
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Xuelian Wang, Na Li, Ying Li, Yinan Zhao, Liang Zhang, Yanjun Sun, Yasushi Ohizumi, Jing Xu, and Yuanqiang Guo
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Polysaccharide ,Anti-tumor activity ,Immunomodulatory activity ,RAW264.7 ,Zebrafish ,Paeonia lactiflora ,Chemistry ,QD1-999 - Abstract
An unreported polysaccharide, PLP90-1B, was isolated from Paeonia lactiflora. Structural analysis showed that PLP90-1B contained arabinose and glucose, which was a highly-linear gluco-arabinan having a molecular weight of about 9.5 kDa. The backbone of PLP90-1B consisted of → 5)-α-l-Araf-(1→, →3,5)-α-l-Araf-(1→, →2,3,5)-α-l-Araf-(1→, and → 4)-α-d-Glcp-(1→, terminating with α-l-Araf. PLP90-1B was found to have anti-tumor activity by suppressing the proliferation and migration of HepG2 cells microinjected into the zebrafish. The further mechanism investigation revealed that the anti-tumor activity of PLP90-1B was closely related to immune regulation, which can improve phagocytic ability and enhance the release of NO and cytokines (IL-6, IL-1β, and TNF-α) in RAW264.7 cells. The immunopotentiation activity was further corroborated by zebrafish experiments. All these results exhibited that PLP90-1B may have the potential to become a potentially immune-mediated anti-tumor drug in the future.
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- 2022
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7. Preparation, characterization, and antitumor activity of Chaenomeles speciosa polysaccharide-based selenium nanoparticles
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Linan Zhou, Yeling Li, Xiaotang Gong, Zhengguo Li, Honglin Wang, Lingling Ma, Muhetaer Tuerhong, Munira Abudukeremu, Yasushi Ohizumi, Jing Xu, and Yuanqiang Guo
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Selenium nanoparticles ,Antitumor ,Chaenomeles speciosa polysaccharide ,Zebrafish ,Chemistry ,QD1-999 - Abstract
Nanoparticles have been found to possess unique advantages in many fields, especially in the field of cancer treatment. Herein, based on the unique physical and chemical properties of natural polysaccharides, the polysaccharide from the edible and medicinal fruits of Chaenomeles speciosa was prepared, and the complex nanoparticles constructed by combining C. speciosa polysaccharide with selenium have been successfully developed by a chemical method. Monodisperse spherical nanoparticles with the particle size of 80.5 nm were characterized by various methods, which exhibited ideal size distribution and prominent stability under physiological conditions and alkaline conditions. Cellular studies demonstrated the nanoparticles significantly inhibited the growth of MCF-7 cells with an IC50 value of 8.37 ± 0.97 μg/mL through inducing the apoptosis and arresting the cell circle at S phase. Moreover, the zebrafish assays confirmed the antitumor effects of the nanoparticles, which suppressed the proliferation and migration of tumor and blocked the angiogenesis of transgenic zebrafish. Collectively, the results suggested that the nanoparticles may be considered as a candidate agent to treat breast cancer.
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- 2022
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8. Anti-inflammatory Limonoids From Cortex Dictamni
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Yue Chen, Jingya Ruan, Fan Sun, Huimei Wang, Shengcai Yang, Ying Zhang, Jiejing Yan, Haiyang Yu, Yuanqiang Guo, Yi Zhang, and Tao Wang
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Cortex Dictamni ,dictamlimonoside ,dictamlimonol ,tumor necrosis factor ,interleukin-6 ,inducible nitric oxide synthase ,Chemistry ,QD1-999 - Abstract
The root barks of perennial herb Dictamnus dasycarpus (Cortex Dictamni) were reported to be rich in anti-inflammation activity constituents, limonoids. Then, the investigation of anti-inflammation therapeutic limonoids from this plant was developed in the present study. Through the combination of various chromatographies isolation, six new limonoids, named dictamlimonol A (1), dictamlimonoside B (2), and dictamlimonols C–F (3–6), along with seven known ones (7–13), were obtained. Their structures were ascertained based on the extensive spectroscopic methods and ECD data analysis. Among them, compound 1 was the first 7,19-epoxy limonoid found in natural products. The anti-inflammatory effects of all limonoids were evaluated in lipopolysaccharide (LPS)-treated RAW 264.7 cell lines. Compounds 5, 7–11, and 13 were found to inhibit LPS-induced nitric oxide (NO) production. Moreover, dictamlimonol D (5), fraxinellone (11), and dasylactone A (13) were found to reduce the LPS-induced expressions of interleukin-6 (IL-6), tumor necrosis factor (TNF-α), inducible nitric oxide synthase (iNOS), nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB), and cyclooxygenase-2 (COX-2) at the protein levels in a dose-dependent manner. These findings support that the administration of Cortex Dictamni may be beneficial for inflammation.
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- 2020
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9. Construction and antitumor activity of selenium nanoparticles decorated with the polysaccharide extracted from Citrus limon (L.) Burm. f. (Rutaceae)
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Shaojie Zhang, Yeling Li, Ziteng Song, Jing Xu, Yuanqiang Guo, and Linan Zhou
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Citrus ,Metal Nanoparticles ,chemistry.chemical_element ,Antineoplastic Agents ,Apoptosis ,Polysaccharide ,Biochemistry ,Animals, Genetically Modified ,Selenium ,Polysaccharides ,Structural Biology ,In vivo ,Spectroscopy, Fourier Transform Infrared ,Animals ,Humans ,Bioassay ,Molecular Biology ,IC50 ,Zebrafish ,chemistry.chemical_classification ,Neovascularization, Pathologic ,biology ,Chemistry ,Monosaccharides ,Hep G2 Cells ,General Medicine ,biology.organism_classification ,Xenograft Model Antitumor Assays ,Bioavailability ,Rutaceae ,Spectrophotometry, Ultraviolet ,HeLa Cells - Abstract
Selenium nanoparticles (SeNPs), a potential cancer therapeutic agent, have attracted widespread attention owing to their high bioavailability and remarkable anticancer activity. Nevertheless, the poor water solubility and dispersibility of SeNPs seriously limit their applications. In the present study, we synthesized stable and individual spherical selenium nanoparticles (CL90-Tw-SeNP2) with an average diameter of approximately 79 nm using a polysaccharide extracted from Citrus limon (CL90) and Tween-80 as the decorator and stabilizers. The proportion of selenium in CL90-Tw-SeNP2 was 10.6%. CL90-Tw-SeNP2 possessed high stability and good dispersion in water for more than three months. The subsequent biological assay revealed that CL90-Tw-SeNP2 showed remarkable antitumor effects against HepG2 cells, with an IC50 value of 49.13 μg/mL, by inducing cell apoptosis. Furthermore, an in vivo zebrafish assay to explore possible applications indicated that CL90-Tw-SeNP2 could inhibit the proliferation and migration of tumors and the zebrafish angiogenesis. These results indicated that CL90-Tw-SeNP2 could be a potential agent for cancer treatment, especially against human liver hepatoma cancer.
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- 2021
10. A new α-pyrone from Arthrinium pseudosinense culture medium and its estrogenic activity in MCF-7 cells
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Dongho Lee, Ki Sung Kang, Jae Jin Kim, Yuanqiang Guo, Sang Hee Shim, Quynh Nhu Nguyen, Ki-Hyun Kim, Haeun Kwon, Myung Woo Na, and Joung Han Yim
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Magnetic Resonance Spectroscopy ,medicine.drug_class ,Stereochemistry ,Chemical structure ,Breast Neoplasms ,Mass Spectrometry ,chemistry.chemical_compound ,Ascomycota ,Drug Discovery ,medicine ,Humans ,Cell Proliferation ,Pharmacology ,Arthrinium ,Estrogen Receptor alpha ,Absolute configuration ,Estrogens ,Pyrone ,chemistry ,MCF-7 ,Pyrones ,Estrogen ,Cancer cell ,MCF-7 Cells ,Phosphorylation ,Female - Abstract
A new α-pyrone analog, arthrifuranone A (1) was isolated from an EtOAc-extract of Arthrinium pseudosinense culture medium. The isolation workflow was guided by a Molecular Networking-based dereplication strategy. The chemical structure of the new compound was elucidated using MS and NMR spectroscopic techniques, and the absolute configuration was established by the Mosher's method and gauge-including atomic orbital NMR chemical shift calculations, followed by DP4 + analysis. The isolated compound was evaluated for its estrogenic activity using the MCF-7 estrogen responsive human breast cancer cells. Compound 1 showed estrogenic activity by increasing the proliferation of MCF-7 cells at the concentration of 3.125 μM via phosphorylation of estrogen receptor-α.
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- 2021
11. Diarylheptanoid‐flavanone Hybrids as Multiple‐target Antidiabetic Agents from Alpinia katsumadai
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Yuanqiang Guo, Xiao-Yan Huang, Ji-Jun Chen, Tian-Ze Li, Chang-An Geng, Xue-Mei Zhang, Jing Hu, and Xiao-Feng He
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chemistry.chemical_compound ,chemistry ,biology ,Traditional medicine ,Diarylheptanoid ,Alpinia ,General Chemistry ,biology.organism_classification ,Multiple target ,Flavanone ,Antidiabetic agents - Published
- 2021
12. Cytotoxic and Antiangiogenetic Xanthones Inhibiting Tumor Proliferation and Metastasis from Garcinia xipshuanbannaensis
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Shaojie Zhang, Dongho Lee, Huimei Wang, Anna-Mari Reid, Yasushi Ohizumi, Jing Xu, Yuanqiang Guo, Xuke Zhang, Jie Zhang, Namrita Lall, Chunyan Wang, Ying Li, and Ziteng Song
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Pharmacology ,biology ,010405 organic chemistry ,Chemistry ,Organic Chemistry ,Pharmaceutical Science ,Cell cycle ,biology.organism_classification ,medicine.disease ,01 natural sciences ,0104 chemical sciences ,Analytical Chemistry ,Metastasis ,HeLa ,010404 medicinal & biomolecular chemistry ,Complementary and alternative medicine ,Prenylation ,In vivo ,Apoptosis ,Drug Discovery ,medicine ,Molecular Medicine ,Cytotoxic T cell ,Cytotoxicity - Abstract
Eight prenylated xanthones including four new analogues were extracted and purified from the leaves of Garcinia xipshuanbannaensis. Multiple techniques including UV, 1D and 2D NMR, and HRESIMS were used to determine the structures of the isolated xanthones. These xanthones were evaluated for their cytotoxicity toward human cancer cells, and compound 4 exhibited activity against HeLa cells. A cytotoxic mechanism examination revealed the active compound induced cell apoptosis by arresting the cell cycle, increasing the levels of ROS, and inhibiting the expression of p-STAT3 in HeLa cells. In in vivo zebrafish experiments, compound 4 was found to block tumor proliferation and migration and have antiangiogenetic activity, and thus seems worthy of further laboratory evaluation.
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- 2021
13. Isolation of Adenosine and Cordysinin B from Anredera cordifolia that Stimulates CRE-Mediated Transcription in PC12 Cells
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Akira Nakajima, Yasushi Ohizumi, Yasumasa Hara, Masami Ishibashi, Maki Kamada, Yuanqiang Guo, Koji Kajima, Nobuyuki Uozumi, and Michi Kawada
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0303 health sciences ,biology ,Chemistry ,Ethyl acetate ,biology.organism_classification ,Adenosine ,03 medical and health sciences ,chemistry.chemical_compound ,0302 clinical medicine ,Column chromatography ,Biochemistry ,Transcription (biology) ,medicine ,Cyclic adenosine monophosphate ,Signal transduction ,Receptor ,Anredera cordifolia ,030217 neurology & neurosurgery ,030304 developmental biology ,medicine.drug - Abstract
Alzheimer’s disease is a typical neurodegenerative disorder, and its prevention or treatment poses great concern in advanced countries. In our survey of numerous natural resources with neurotrophic activities, we found that Anredera cordifolia improved memory impairment and increased cyclic adenosine monophosphate (AMP) response element-mediated transcription, an important step in signal transduction for memory formation. The extracts of this food were dissolved in methanol and then partitioned with three organic solvents and water, separating into n-hexane, ethyl acetate, n-butanol, and water layers. The n-butanol layer with the strongest activity on cyclic AMP-response element-dependent transcription was fractionated using silica gel column chromatography and then the activity was monitored using preparative high-performance liquid chromatography to give adenosine and cordysinin B, respectively. Both compounds showed a concentration-dependent increase in cyclic AMP-response element-mediated transcription activity. These results suggest that both adenosine and cordysinin B may participate in improving the action of A. cordifolia on memory impairment, and these actions, at least in part, result from the activation of adenosine A1, A2A, and A2B receptors.
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- 2021
14. Tsaokols A and B, unusual flavanol-monoterpenoid hybrids as α-glucosidase inhibitors from Amomum tsao-ko
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Chang-An Geng, Tian-Ze Li, Xue-Mei Zhang, Xuke Zhang, Xiao-Feng He, Jing Hu, Ji-Jun Chen, and Yuanqiang Guo
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chemistry.chemical_classification ,Circular dichroism ,Dried fruit ,biology ,Bicyclic molecule ,Chemistry ,Stereochemistry ,02 engineering and technology ,General Chemistry ,010402 general chemistry ,021001 nanoscience & nanotechnology ,biology.organism_classification ,01 natural sciences ,Amomum ,0104 chemical sciences ,Enzyme ,Docking (molecular) ,Michael reaction ,medicine ,0210 nano-technology ,Acarbose ,medicine.drug - Abstract
Tsaokols A (1) and B (2), two complicated flavanol-monoterpenoid hybrids, were isolated from the dried fruits of Amomum tsao-ko under the guidance of LCMS and bioassay. Their structures were determined by extensive spectroscopic analyses and electronic circular dichroism (ECD) calculations. Compounds 1 and 2 shared a flavanol backbone fused with 5/7 and 5/6 bicyclic monoterpenoid scaffolds, which were biogenetically condensed by Michael addition and acetalization. Compounds 1 and 2 exhibited significant α-glucosidase inhibitory activity with IC50 values of 18.8 and 38.6 μmol/L (acarbose, IC50 = 213 μmol/L). Docking study supported the strong interactions of 1 and 2 bonding with enzyme by mainly hydrophobic and hydrogen-bond effects. Compounds 1 and 2 could be fast distinguished by the diagnostic ions at m/z 289 and 313 in negative MS2 experiments.
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- 2021
15. The inhibition of Mpro, the primary protease of COVID-19, by Poria cocos and its active compounds: a network pharmacology and molecular docking study
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Xiao-Xue Chen, Dan-Shui Zhou, Liping Ren, Wei-Ju Ni, Zhi-Min Wu, Zhengpu Zhang, Yu Zeng, Yuanqiang Guo, Weile Ye, and Shanshan Chai
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Active ingredient ,chemistry.chemical_classification ,0303 health sciences ,Primary (chemistry) ,Protease ,biology ,Coronavirus disease 2019 (COVID-19) ,General Chemical Engineering ,medicine.medical_treatment ,Active site ,General Chemistry ,03 medical and health sciences ,0302 clinical medicine ,Triterpene ,chemistry ,Biochemistry ,030220 oncology & carcinogenesis ,Network pharmacology ,biology.protein ,medicine ,IC50 ,030304 developmental biology - Abstract
Poria cocos is a traditional Chinese medicine (TCM) that can clear dampness, promote diuresis, and strengthen the spleen and stomach. Poria cocos has been detected in many TCM compounds that are used for COVID-19 intervention. However, the active ingredients and mechanisms associated with the effect of Poria cocos on COVID-19 remain unclear. In this paper, the active ingredients of Poria cocos, along with their potential targets related to COVID-19, were screened using TCMSP, GeneCards, and other databases, by means of network pharmacology. We then investigated the active components, potential targets, and interactions, that are associated with COVID-19 intervention. The primary protease of COVID-19, Mpro, is currently a key target in the design of potential inhibitors. Molecular docking techniques and molecular dynamics simulations demonstrated that the active components of Poria cocos could bind stably to the active site of Mpro with high levels of binding activity. Pachymic acid is based on a triterpene structure and was identified as the main component of Poria cocos; its triterpene active component has low binding energy with Mpro. The pachymic acid of Mpro activity was further characterized and the IC50 was determined to be 18.607 μmol L−1. Our results indicate that pachymic acid exhibits a certain inhibitory effect on the Mpro protease.
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- 2021
16. Antimicrobial Furancarboxylic Acids from a Penicillium sp
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Yuanqiang Guo, Xuke Zhang, Hong-Zhe Xu, Ming Zhou, Jin-Ling Chang, Han-Li Ruan, and Jia Zhou
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Pharmacology ,Circular dichroism ,biology ,Stereochemistry ,Organic Chemistry ,Pharmaceutical Science ,Antimicrobial ,biology.organism_classification ,medicine.disease_cause ,Analytical Chemistry ,chemistry.chemical_compound ,Complementary and alternative medicine ,chemistry ,Drug Discovery ,Penicillium ,medicine ,Thiophene ,Molecular Medicine ,Moiety ,Epimer ,Fermentation ,Escherichia coli - Abstract
Ten novel (1, 2, 3a, 3b, 4a, 4b, 5a, 5b, 6a, and 6b) furancarboxylic acids including four pairs of epimers (3a, 3b; 4a, 4b; 5a, 5b; 6a, 6b), together with seven known analogues (7a, 7b, 8a, 8b, 9a, 9b, and 10), were isolated from the fermentation of the soil-derived fungus Penicillium sp. sb62. Their structures were established on the basis of spectroscopic data analysis, and the absolute configurations were determined by time-dependent density functional theory electronic circular dichroism calculations, comparison of the specific optical rotation values, and modified Mosher's method. Compounds 1-4 represent the first class of natural furancarboxylic acids featuring a thiophene moiety. Compounds 1-7 showed antimicrobial inhibitory activities against Escherichia coli, Staphylococcus aureus, and Candida albicans with MIC values ranging from 0.9 to 7.0 μg/mL, from 1.7 to 3.5 μg/mL, and from 3.3 to 7.0 μg/mL, respectively.
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- 2020
17. Anti-Inflammatory ent-Kaurane Diterpenoids from Isodon serra
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Dongho Lee, Munira Abudukeremu, Jie Zhang, Jing Xu, Dihua Li, Honghong Xing, Ziteng Song, Namrita Lall, Yuanqiang Guo, Huimei Wang, Shanshan Li, Chunyan Wang, Lijun An, and Muhetaer Tuerhong
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Circular dichroism ,Stereochemistry ,medicine.drug_class ,Pharmaceutical Science ,01 natural sciences ,Anti-inflammatory ,Analytical Chemistry ,Nitric oxide ,chemistry.chemical_compound ,Drug Discovery ,medicine ,No production ,Ent kaurane ,Pharmacology ,biology ,010405 organic chemistry ,Organic Chemistry ,Isodon serra ,0104 chemical sciences ,Nitric oxide synthase ,010404 medicinal & biomolecular chemistry ,Complementary and alternative medicine ,chemistry ,biology.protein ,Molecular Medicine ,Epimer - Abstract
Ten new ent-kaurane diterpenoids, including two pairs of epimers 1/2 and 4/5 and a 6,7-seco-ent-kauranoid 10, were obtained from the aerial parts of Isodon serra. The structures of the new compounds were confirmed by extensive spectroscopic methods and electronic circular dichroism (ECD) data analysis. An anti-inflammatory assay was applied to evaluate their nitric oxide (NO) inhibitory activities by using LPS-stimulated BV-2 cells. Compounds 1 and 9 exhibited notable NO production inhibition with IC50 values of 15.6 and 7.3 μM, respectively. Moreover, the interactions of some bioactive diterpenoids with inducible nitric oxide synthase (iNOS) were explored by employing molecular docking studies.
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- 2020
18. Nineteen New Flavanol–Fatty Alcohol Hybrids with α-Glucosidase and PTP1B Dual Inhibition: One Unusual Type of Antidiabetic Constituent from Amomum tsao-ko
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Tian-Ze Li, Yuanqiang Guo, Xiao-Feng He, Chang-An Geng, Xue-Mei Zhang, Jing Hu, Xuke Zhang, and Ji-Jun Chen
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biology ,Dried fruit ,Stereochemistry ,Fatty alcohol ,Alcohol ,General Chemistry ,biology.organism_classification ,Amomum ,chemistry.chemical_compound ,chemistry ,medicine ,Hemiacetal ,Enzyme kinetics ,General Agricultural and Biological Sciences ,IC50 ,Acarbose ,medicine.drug - Abstract
The dried fruits of Amomum tsao-ko were first revealed to have hypoglycemic effects on db/db mice at a concentration of 200 mg/kg. In order to clarify the antidiabetic constituents, 19 new flavanol-fatty alcohol hybrids, tsaokoflavanols A-S (1-19), were isolated and determined by extensive spectroscopic data and ECD calculations. Most of the compounds showed α-glucosidase and PTP1B dual inhibition, among which 1, 2, 6, 11, and 18 exhibited obvious activity against α-glucosidase with IC50 values of 5.2-9.0 μM, 20-35 times stronger than that of acarbose (IC50, 180.0 μM); meanwhile, 6, 10-12, and 19 were PTP1B/TCPTP-selective inhibitors with IC50 values of 56.4-80.4 μM, 2-4 times stronger than that of suramin sodium (IC50, 200.5 μM). Enzyme kinetics study indicated that compounds 1, 2, 6, and 11 were α-glucosidase and PTP1B mixed-type inhibitors with Ki values of 13.0, 11.7, 2.9, and 5.3 μM and 142.3, 88.9, 39.2, and 40.8 μM, respectively. Docking simulations proved the importance of hemiacetal hydroxy, the orientation of 3,4-dihydroxyphenyl, and the length of alkyl in binding with α-glucosidase and PTP1B.
- Published
- 2020
19. Euphnerins A and B, Diterpenoids with a 5/6/6 Rearranged Spirocyclic Carbon Skeleton from the Stems of Euphorbia neriifolia
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Lijun An, Min Du, Yuanqiang Guo, and Jing Xu
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Pharmacology ,Circular dichroism ,Chemistry ,Stereochemistry ,Organic Chemistry ,Carbon skeleton ,Pharmaceutical Science ,Nuclear magnetic resonance spectroscopy ,Molecular conformation ,Terpenoid ,Analytical Chemistry ,Complementary and alternative medicine ,Drug Discovery ,Molecular Medicine ,Molecule ,Euphorbia neriifolia - Abstract
Euphnerins A (1) and B (2), two extremely modified diterpenoids possessing an unprecedented 5/6/6 rearranged spirocyclic carbon skeleton, and a biosynthetically related known diterpenoid (3) were purified from the stems of Euphorbia neriifolia. Their structures were identified by NMR experiments and X-ray diffraction analysis, as well as experimental and calculated electronic circular dichroism data comparison. A putative biosynthetic relationship of 1 and 2 with their presumed precursor 3 is proposed. Compound 1 showed NO inhibitory effects in lipopolysaccharide-stimulated BV-2 cells with an IC50 value of 22.4 μM.
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- 2020
20. Analysis of chemical composition of Inula japonica Thunb. extract and in vitro screening for anti-pulmonary fibrosis active components
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Honggang Zhou, Shaoyan Gao, Feng Liu, Bingchen Zhou, Xiaohe Li, Yuanqiang Guo, Shuaishuai Liu, Mengying Huang, and Bai Jiakun
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010405 organic chemistry ,Chemistry ,Plant Science ,Pharmacology ,medicine.disease ,01 natural sciences ,Biochemistry ,High-performance liquid chromatography ,In vitro ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,Idiopathic pulmonary fibrosis ,Column chromatography ,Fibrosis ,Pulmonary fibrosis ,medicine ,MTT assay ,Cytotoxicity ,Agronomy and Crop Science ,Biotechnology - Abstract
Idiopathic pulmonary fibrosis (IPF) is a fatal and progressive lung disease with limited therapies, while transforming growth factor-β1 (TGF-β1) plays a central role in the pathogenesis of IPF. Here, we aim to investigate the chemical constituents and biological activities of Inula japonica Thunb. on the TGF-β1/Smad3 signaling pathway to determine the principal compounds of anti-pulmonary fibrosis drugs. Extracts of Inula japonica Thunb. were separated by silica gel column chromatography, ODS medium pressure liquid chromatography and HPLC. The purities and structures were established by NMR, MS and circular dichroism. These extracts’ cytotoxicity and proliferation inhibition of fibroblasts were determined by MTT assay. The lung fibroblasts stably transformed with TGF-β1/Smad3-luciferase reporter gene were used to screen for active ingredients that exert an inhibitory effect on the TGF-β1/Smad3 signaling pathway. Real-time PCR assays were used to detect whether the selected compounds could interfere with the activation of fibroblasts. Among the nineteen compounds extracted from Inula japonica Thunb., 15 and 17 have shown significant inhibitory activity of the TGF-β1/Smad3 pathway in fibroblasts. Additionally, mRNA levels of α-SMA and collagen 1 in myofibroblasts after TGF-β1 stimulation were suppressed by 15 and 17. In conclusion, chemical components of the extract from Inula japonica Thunb. might be potential agents for the treatment of IPF.
- Published
- 2020
21. Anti-inflammatory neo-Clerodane Diterpenoids from Ajuga pantantha
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Xuke Zhang, Muhetaer Tuerhong, Dongho Lee, Chunyan Wang, Namrita Lall, Lijun An, Munira Abudukeremu, Ling Shuai, Jing Xu, Yuanqiang Guo, Xueyuan Yang, Bangjian Dong, Wenpei Liu, and Qing Du
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Pharmacology ,Plant Components ,Circular dichroism ,biology ,010405 organic chemistry ,medicine.drug_class ,Stereochemistry ,Chemistry ,Organic Chemistry ,Pharmaceutical Science ,Nuclear magnetic resonance spectroscopy ,biology.organism_classification ,01 natural sciences ,Anti-inflammatory ,Ajuga ,0104 chemical sciences ,Analytical Chemistry ,Nitric oxide synthase ,010404 medicinal & biomolecular chemistry ,Complementary and alternative medicine ,Drug Discovery ,Ic50 values ,medicine ,biology.protein ,Molecular Medicine - Abstract
Eight new neo-clerodane diterpenoids (1-8) were acquired from the aerial parts of Ajuga pantantha. Spectroscopic data analysis permitted the definition of their structures, and experimental and calculated electronic circular dichroism data were used to define their absolute configurations. Compounds 2 and 4-8 were found to have NO inhibitory effects with IC50 values of 20.2, 45.5, 34.0, 27.0, 45.0, and 25.8 μM, respectively. The more potent compounds 2, 6, and 8 were analyzed to establish their anti-inflammatory mechanism, including regulation of the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) proteins as well as their binding interactions with the two proteins.
- Published
- 2020
22. Anti-inflammatory Metabolites from Chaetomium nigricolor
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Seung Mok Ryu, Min Jee Kim, Haeun Kwon, Hyuncheol Oh, Dong-Cheol Kim, Youn-Chul Kim, Dongho Lee, Seung Beom Hong, Yuanqiang Guo, and Jaeyoung Kwon
- Subjects
Pharmacology ,010405 organic chemistry ,medicine.drug_class ,Chemistry ,Kinase ,Organic Chemistry ,Pharmaceutical Science ,Interleukin ,01 natural sciences ,Anti-inflammatory ,0104 chemical sciences ,Analytical Chemistry ,Nitric oxide ,010404 medicinal & biomolecular chemistry ,Enzyme activator ,chemistry.chemical_compound ,Complementary and alternative medicine ,Biochemistry ,Drug Discovery ,medicine ,Molecular Medicine ,Tumor necrosis factor alpha ,Prostaglandin E2 ,RAW 264.7 Cells ,medicine.drug - Abstract
Twelve metabolites were obtained from the culture media of Chaetomium nigricolor, including a new furan derivative, methyl succinyl Sumiki's acid (1), and two new atropisomers of the previously reported bis-naphtho-γ-pyrones, (aS)-asperpyrone A and (aS)-fonsecinone A (2 and 3). The structures were elucidated by spectroscopic, chemical, and chiroptical techniques. Compounds 2 and 3 inhibited nitric oxide production in lipopolysaccharide-stimulated RAW 264.7 macrophages. Compound 2 was found to inhibit nuclear factor-kappa B and c-Jun N-terminal kinase activation, in turn suppressing pro-inflammatory mediators and cytokines including nitric oxide, prostaglandin E2, interleukin (IL)-1β, tumor necrosis factor-α, IL-6, and IL-12.
- Published
- 2020
23. Clerodane Diterpenoids Isolated from the Leaves of Casearia graveolens
- Author
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Zhaohui Song, Yuanqiang Guo, Zhaoyu Shi, Jin Jin, Feng Liu, Munira Abudukeremu, Chunyan Wang, Dongho Lee, Dihua Li, Jun Ma, Muhetaer Tuerhong, Huimei Wang, Ling Shuai, Qi Zhang, and Jing Xu
- Subjects
Pharmacology ,A549 cell ,Casearia ,biology ,Traditional medicine ,010405 organic chemistry ,Human lung cancer ,Chemistry ,Organic Chemistry ,Pharmaceutical Science ,biology.organism_classification ,01 natural sciences ,0104 chemical sciences ,Analytical Chemistry ,010404 medicinal & biomolecular chemistry ,Complementary and alternative medicine ,Phytochemical ,Drug Discovery ,Molecular Medicine ,Cytotoxic T cell ,Biological evaluation - Abstract
A phytochemical survey aiming to acquire pharmacologically active substances has resulted in the isolation of nine new clerodane diterpenoids, named graveospenes A-I (1-9), from the leaves of Casearia graveolens. Spectroscopic methods were employed to establish the structures with their absolute configurations being confirmed by ECD data analysis. A biological evaluation was performed, and compound 1 was found to be cytotoxic to both human lung cancer cells (A549) and human hepatocellular carcinoma cells (HepG2). A mechanism-of-action study on 1 revealed this compound to induce apoptosis of A549 cells and impede them at the G0/G1 stage.
- Published
- 2020
24. Xylodon flaviporus-Derived Drimane Sesquiterpenoids That Inhibit Osteoclast Differentiation
- Author
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Hak Cheol Kwon, Jong Soon Kang, Hyaemin Lee, Dongho Lee, Jae Jin Kim, Yeongseon Jang, Jaeyoung Kwon, Seung Mok Ryu, and Yuanqiang Guo
- Subjects
Pharmacology ,biology ,010405 organic chemistry ,Chemistry ,Activator (genetics) ,Organic Chemistry ,Pharmaceutical Science ,Nuclear magnetic resonance spectroscopy ,Inhibitory postsynaptic potential ,biology.organism_classification ,01 natural sciences ,Molecular biology ,0104 chemical sciences ,Analytical Chemistry ,010404 medicinal & biomolecular chemistry ,medicine.anatomical_structure ,Complementary and alternative medicine ,Osteoclast ,Drug Discovery ,Ic50 values ,Flaviporus ,medicine ,Molecular Medicine ,Bone marrow ,Receptor - Abstract
The presence of excessive osteoclasts is a major factor in skeletal diseases. The present study aimed to discover osteoclast differentiation inhibitors from the basidiomycete Xylodon flaviporus. Seven new drimane sesquiterpenoids (1-7) and 7-ketoisodrimenin-5-ene (8) were obtained and characterized by various spectroscopic methods. The isolated compounds were evaluated for their inhibitory effects against receptor activator of nuclear factor-kappa-B ligand-induced osteoclastogenesis in mouse bone marrow macrophages. Compounds 1, 3, and 6 showed potent activities with IC50 values of 1.6, 0.9, and 2.1 μM, respectively, while 4, 5, and 7 exhibited relatively weak activities with IC50 values of 10.7, 10.1, and 8.5 μM, respectively.
- Published
- 2019
25. Design and construction of IR780- and EGCG-based and mitochondrial targeting nanoparticles and their application in tumor chemo-phototherapy
- Author
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Yinan Zhao, Jiahe Bao, Yuanqiang Guo, and Jing Xu
- Subjects
Indoles ,Cell Survival ,Photothermal Therapy ,Biomedical Engineering ,Nanoparticle ,Antineoplastic Agents ,complex mixtures ,Catechin ,chemistry.chemical_compound ,In vivo ,Cell Line, Tumor ,Amphiphile ,Hyaluronic acid ,Materials Testing ,Animals ,Humans ,General Materials Science ,Nir laser ,Zebrafish ,Cell Proliferation ,Fluorescent Dyes ,Photosensitizing Agents ,Molecular Structure ,Chemistry ,food and beverages ,General Chemistry ,General Medicine ,Neoplasms, Experimental ,Iodides ,Green tea ,Combinatorial chemistry ,Bioavailability ,Mitochondria ,Drug Design ,Mitochondrial targeting ,Nanoparticles ,Drug Screening Assays, Antitumor - Abstract
An integration combination of phototherapy and chemotherapy to treat carcinoma, addressing the inner limitation of individual-modal chemical agents-based therapy or phototherapy, emerges to be a strategy with high prospect for achieving synergistic curative effects. The dye IR780-iodide (IR780) close to infrared radiation is a phototherapy agent with high prospect, however, it is limited in its application in clinic for poor solubility of water. While, epigallocatechin-3-gallate (EGCG), naturally resourced green tea polyphenol, has been extensively proven with intrinsic antitumor activity, but it is largely restricted by its low bioavailability in vivo. Hence, a novel multiple-function nanoparticle according to hyaluronic acid (HA) and IR780 were proposed to deliver EGCG, defined as EGCG@THSI nano-scale particles (EGCG@THSI NPs), thereby rapidly solving limitations of EGCG and IR780. Amphiphilic nano-scale carrier was prepared by triphenylphosphine (TPP), hyaluronic acid (HA), disulfide bond, and IR780, termed as TPP-HA-SS-IR780, and EGCG was loaded into the amphiphilic copolymer by self-assembly. The TPP-HA-SS-IR780 endowed the as-synthesized EGCG@THSI NPs with excellent TPP-mediated mitochondrial-targeted and glutathione-triggered rapid drug release properties. As impacted by the integration of phototherapy and chemotherapy, the EGCG@THSI NPs under NIR laser irradiation showed prominent anti-tumor effect. Taken together, this study presented a smart multiple-function nano-scale carrier platform with high prospect in improving therapeutic efficacy of anti-carcinoma drugs.
- Published
- 2021
26. The Antitumor Activity and Mechanism of a Natural Diterpenoid From Casearia graveolens
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Yeling Li, Jun Ma, Han Zhang, Yinan Zhao, Ziteng Song, Yuanqiang Guo, Ying Li, and Jing Xu
- Subjects
Cancer Research ,Casearia ,01 natural sciences ,03 medical and health sciences ,In vivo ,Cytotoxic T cell ,FAK-MMPs ,Zebrafish ,RC254-282 ,cytotoxic activity ,030304 developmental biology ,zebrafish xenograft model ,0303 health sciences ,biology ,010405 organic chemistry ,Chemistry ,Cell growth ,apoptosis ,Neoplasms. Tumors. Oncology. Including cancer and carcinogens ,Cell cycle ,biology.organism_classification ,Terpenoid ,0104 chemical sciences ,Cell biology ,Oncology ,Apoptosis ,cell cycle ,antiangiogenesis inhibitors - Abstract
Casearlucin A, a diterpenoid obtained from Casearia graveolens, has been reported to possess strong cytotoxic activity. However, the in vivo anti-tumor effects and the action mechanism of casearlucin A remain poorly understood. Our study revealed that casearlucin A arrested cell cycle at G0/G1 stage and induced cell apoptosis in cell level. Additionally, casearlucin A inhibited HepG2 cell migration via regulating a few of metastasis-related proteins. Furthermore, it inhibited tumor angiogenesis in zebrafish in vivo. More importantly, casearlucin A significantly inhibited cell proliferation and migration in an in vivo zebrafish xenograft model. Collectively, these results are valuable for the further development and application of casearlucin A as an anticancer agent.
- Published
- 2021
27. Preparation and structural properties of selenium modified heteropolysaccharide from the fruits of Akebia quinata and in vitro and in vivo antitumor activity
- Author
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Jing Xu, Ying Li, Muhetaer Tuerhong, Yuanqiang Guo, Yuhao Li, Jianlin Cui, Munira Abudukeremu, Xuelian Wang, Da-Qing Jin, and Huimei Wang
- Subjects
Arabinose ,Polymers and Plastics ,Ranunculales ,Rhamnose ,chemistry.chemical_element ,Angiogenesis Inhibitors ,Polysaccharide ,Akebia quinata ,chemistry.chemical_compound ,Selenium ,Liver Neoplasms, Experimental ,In vivo ,Cell Movement ,Polysaccharides ,Materials Chemistry ,Carbohydrate Conformation ,Animals ,Humans ,Zebrafish ,Cell Proliferation ,chemistry.chemical_classification ,biology ,Neovascularization, Pathologic ,Organic Chemistry ,Hep G2 Cells ,biology.organism_classification ,Antineoplastic Agents, Phytogenic ,In vitro ,Biochemistry ,chemistry ,Galactose ,Fruit ,Drug Screening Assays, Antitumor - Abstract
Cancer is a complex disease, and blocking tumor angiogenesis has become one of the most promising approaches in cancer therapy. Here, an exopoly heteropolysaccharide (AQP70-2B) was firstly isolated from the Akebia quinata. Monosaccharide composition indicated that the AQP70-2B was composed of rhamnose, glucose, galactose, and arabinose. The backbone of AQP70-2B consisted of →1)-L-Araf, →3)-L-Araf-(1→, →5)-L-Araf-(1→, →3,5)-L-Araf-(1→, →2,5)-L-Araf-(1→, →4)-D-Glcp-(1→, →6)-D-Galp-(1→, and →1)-D-Rhap residues. Based on the close relationship between selenium and anti-tumor activity, AQP70-2B was modified with selenium to obtain selenized polysaccharide Se-AQP70-2B. Then, a series of methods for analysis and characterization, especially scanning electron microscopy coupled with energy dispersive spectrometry (SEM-EDS), indicated that Se-AQP70-2B was successfully synthesized. Furthermore, zebrafish xenografts and anti-angiogenesis experiments indicated that selenization could improve the antitumor activity by inhibiting tumor cell proliferation and migration and blocking angiogenesis.
- Published
- 2021
28. Clerodane diterpenoids from Casearia kurzii and their cytotoxic activities
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Annan Li, Yuan Shuo, Yuanqiang Guo, Feng Liu, Jun Ma, Dongho Lee, Qi Zhang, Yasushi Ohizumi, Chenyue Zhang, and Xueyuan Yang
- Subjects
Circular dichroism ,Magnetic Resonance Spectroscopy ,Casearia ,Stereochemistry ,Pharmacology toxicology ,01 natural sciences ,Diterpenes, Clerodane ,HeLa ,Cell Line, Tumor ,Humans ,Cytotoxic T cell ,Plants, Medicinal ,Molecular Structure ,biology ,010405 organic chemistry ,Chemistry ,Circular Dichroism ,biology.organism_classification ,Antineoplastic Agents, Phytogenic ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,Cell culture ,Molecular Medicine ,Drug Screening Assays, Antitumor ,Human cancer ,HeLa Cells - Abstract
A search for bioactive natural products as anticancer lead compounds resulted in the isolation of one previously undescribed and three known clerodane diterpenoids (1–4) from Casearia kurzii. The structures of these compounds were established by analysis of their NMR, MS, and electronic circular dichroism data. The cytotoxic activities of four compounds against three human cancer cell lines were evaluated. Compound 2 was found to be the most active with an IC50 value of 4.1 μM against HeLa cells, and was selected to investigate the possible cytotoxic mechanism.
- Published
- 2019
29. Cytotoxic clerodane diterpenoids from the leaves of Casearia kurzii
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Jie Zhang, Chunfeng Xie, Xueyuan Yang, Qi Zhang, Dongho Lee, Jing Xu, Jun Ma, Yasushi Ohizumi, Yuanqiang Guo, Xuke Zhang, Muhetaer Tuerhong, and Da Qing Jin
- Subjects
Casearia ,Apoptosis ,01 natural sciences ,Biochemistry ,Diterpenes, Clerodane ,HeLa ,Cell Line, Tumor ,Drug Discovery ,medicine ,Humans ,Cytotoxic T cell ,Molecular Biology ,A549 cell ,biology ,010405 organic chemistry ,Chemistry ,Organic Chemistry ,Cancer ,Stereoisomerism ,Cell cycle ,biology.organism_classification ,medicine.disease ,Antineoplastic Agents, Phytogenic ,G1 Phase Cell Cycle Checkpoints ,0104 chemical sciences ,Plant Leaves ,010404 medicinal & biomolecular chemistry ,Cell culture ,Drug Screening Assays, Antitumor - Abstract
A phytochemical investigation to obtain bioactive substances as lead compounds or agents for cancer led to the obtainment of six new clerodane diterpenoids, designated as kurzipenes A–F (1–6), from the leaves of Casearia kurzii. Their structures were elucidated on the basis of NMR spectroscopic data analysis and the absolute configurations were confirmed by the time-dependent density functional theory (TDDFT) electronic circular dichroism (ECD) calculations. The cytotoxic activities of compounds 1–6 were evaluated against human lung cancer A549 cell line, human cervical cancer Hela cell line, and human hepatocellular carcinoma HepG2 cell line. Most diterpenoids showed potent cytotoxicities against the three selected cancer cell lines. The preliminary mechanism studies revealed that the most active compound 2, with an IC50 value of 5.3 μM against Hela cells, induced apoptosis and arrested the Hela cell cycle at the G0/G1 stage to exert cytotoxic effects.
- Published
- 2019
30. Nitric oxide inhibitory limonoids as potential anti-neuroinflammatory agents from Swietenia mahagoni
- Author
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Jie Zhang, Yasushi Ohizumi, Lijun An, Da Qing Jin, Yaru Xi, Jing Xu, Yuan Shuo, Dongho Lee, Yuanqiang Guo, Zhaoyu Shi, Xueyuan Yang, and Chenyue Zhang
- Subjects
Limonins ,Lipopolysaccharides ,Circular dichroism ,Nitric Oxide ,Limonoid ,01 natural sciences ,Biochemistry ,Cell Line ,Nitric oxide ,Mice ,Structure-Activity Relationship ,chemistry.chemical_compound ,Drug Discovery ,medicine ,Animals ,Orthoester ,Meliaceae ,Swietenia mahagoni ,Molecular Biology ,Neuroinflammation ,Dose-Response Relationship, Drug ,Molecular Structure ,biology ,010405 organic chemistry ,Chemistry ,Anti-Inflammatory Agents, Non-Steroidal ,Organic Chemistry ,biology.organism_classification ,0104 chemical sciences ,Molecular Docking Simulation ,Nitric oxide synthase ,010404 medicinal & biomolecular chemistry ,Phytochemical ,Fruit ,biology.protein ,medicine.drug - Abstract
Recent studies have revealed that there is a close relationship between neuroinflammation and Alzheimer's disease (AD) and compounds with anti-neuroinflammatory effects are potentially useful for the treatment of AD. A phytochemical investigation to obtain new neuroinflammatory inhibitors resulted in the isolation of four new and three known limonoids from Swietenia mahagoni. The structures of these limonoids were established by NMR, MS, and electronic circular dichroism (ECD) data analysis. Compounds 1–3 feature complicated polycyclic caged structures of limonoid orthoester and represent new examples of phragmalin-type limonoids. All of the isolates showed anti-neuroinflammatory activities by inhibiting nitric oxide (NO) release in LPS-induced murine microglial BV-2 cells with compounds 1 and 3–6 having IC50 values of 26.8, 26.1, 26.0, 37.1, and 16.5 μM, respectively. The possible mechanism of NO inhibition of some bioactive compounds was also investigated using molecular docking, which revealed the interactions of bioactive compounds with the inducible nitric oxide synthase (iNOS) protein.
- Published
- 2019
31. Bioactive Diterpenoids from the Stems of Euphorbia royleana
- Author
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Yasushi Ohizumi, Chenyue Zhang, Yuanqiang Guo, Peixia Wang, Jing Xu, Chunfeng Xie, Shuo Yuan, Muhetaer Tuerhong, Lijun An, Jie Zhang, Da Qing Jin, Dongho Lee, Xueyuan Yang, and Yaru Xi
- Subjects
Pharmacology ,Magnetic Resonance Spectroscopy ,Plant Stems ,biology ,Plant Extracts ,Stereochemistry ,Chemistry ,Organic Chemistry ,Pharmaceutical Science ,Nitric Oxide ,biology.organism_classification ,Terpenoid ,Analytical Chemistry ,Euphorbia royleana ,Molecular Docking Simulation ,Complementary and alternative medicine ,Euphorbia ,Drug Discovery ,Ic50 values ,Molecular Medicine ,Diterpenes - Abstract
Two ingenane- (1 and 2), two ent-atisane- (3 and 4), two ent-kaurane- (5 and 6), two ent-abietane- (7 and 8), and one ent-isopimarane-type (9) diterpenoid and 12 known analogues have been isolated from the methanolic extract of the stems of Euphorbia royleana. Their structures, including absolute configurations, were determined by extensive spectroscopic methods and ECD data analysis. The nitric oxide inhibitory activities of those diterpenoids were examined biologically in lipopolysaccharide-stimulated BV-2 cells, with compounds 1, 2, 5–7, 10, and 12 having IC50 values lower than 40 μM. Molecular docking was used to investigated the possible mechanism of compounds 1, 2, 5–7, 10, and 12.
- Published
- 2019
32. Enantiomeric Isoflavones with neuroprotective activities from the Fruits of Maclura tricuspidata
- Author
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Bang Yeon Hwang, Dongho Lee, Sungeun Hong, Jaeyoung Kwon, Nahyun Kim, Nguyen Tuan Hiep, Woongchon Mar, and Yuanqiang Guo
- Subjects
0301 basic medicine ,Magnetic Resonance Spectroscopy ,Maclura ,Phytochemicals ,Ethyl acetate ,lcsh:Medicine ,High-performance liquid chromatography ,Neuroprotection ,Article ,03 medical and health sciences ,chemistry.chemical_compound ,0302 clinical medicine ,Cell Line, Tumor ,Humans ,Maclura tricuspidata ,lcsh:Science ,EC50 ,Multidisciplinary ,Chromatography ,Cell Death ,Molecular Structure ,biology ,Plant Extracts ,Chemistry ,lcsh:R ,Nuclear magnetic resonance spectroscopy ,Isoflavones ,biology.organism_classification ,Neuroprotective Agents ,030104 developmental biology ,Fruit ,lcsh:Q ,Enantiomer ,Reactive Oxygen Species ,030217 neurology & neurosurgery ,Signal Transduction - Abstract
Seven pairs of enantiomeric isoflavones (1a/1b–7a/7b) were obtained from the ethyl acetate extract of the fruits of Maclura tricuspidata (syn. Cudrania tricuspidata), and successfully separated by chiral high-pressure liquid chromatography (HPLC). The structures and absolute configurations of the enantiomeric isoflavones were established on the basic of comprehensive spectroscopic analyses and quantum chemical calculation methods. Compounds 1, 1a, and 1b exhibited neuroprotective activities against oxygen-glucose deprivation/reoxygenation (ODG/R)-induced SH-SY5Y cells death with EC50 values of 5.5 µM, 4.0 µM, and 10.0 µM, respectively. Furthermore, 1, 1a, and 1b inhibited OGD/R-induced reactive oxygen species generation in SH-5Y5Y cells with IC50 values of 6.9 µM, 4.5 µM, and 9.5 µM, respectively.
- Published
- 2019
33. Xylopins A–F, six rare guaiane dimers with three different connecting modes from Xylopia vielana
- Author
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Shi-Kai Yan, Xisong Ke, Rong Yan, Yuanqiang Guo, Huang Piao, Weidong Zhang, Yang-Guo Xie, Xianglong Zhong, Hui-Zi Jin, and Ishaq Muhammad
- Subjects
medicine.diagnostic_test ,Stereochemistry ,General Chemical Engineering ,Wnt signaling pathway ,02 engineering and technology ,General Chemistry ,Cell cycle ,010402 general chemistry ,021001 nanoscience & nanotechnology ,Sesquiterpene ,01 natural sciences ,0104 chemical sciences ,Flow cytometry ,chemistry.chemical_compound ,Western blot ,chemistry ,medicine ,Signal transduction ,0210 nano-technology ,Two-dimensional nuclear magnetic resonance spectroscopy ,Xylopia vielana - Abstract
Six rare guaiane-type sesquiterpene dimers xylopins A–F, having three different connecting modes through two direct C–C bonds, were isolated from the roots of Xylopia vielana. Their absolute configurations were established by NOESY analysis, Cu Kα X-ray crystallography, and experimental and calculated electronic circular dichroism spectra. Flow cytometry demonstrated the fact that compound 6 arrested the cell cycle at G2 phase and concentration-dependently induced apoptosis of DU145 cells. Furthermore, the EPT2-TGC cell model, zebrafish study and western blot analysis illustrated compound 6 could induce apoptosis by efficiently inhibiting the Wnt/β-catenin signaling pathway via decreasing the expression of β-catenin.
- Published
- 2019
34. Chemical constituents from basidiomycete Basidioradulum radula culture medium and their cytotoxic effect on human prostate cancer DU-145 cells
- Author
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Yuanqiang Guo, Jaeyoung Kwon, Joung Han Yim, Sun Lul Kwon, Hyaemin Lee, Sullim Lee, Bang Yeon Hwang, Quynh Nhu Nguyen, Haeun Kwon, Jun Lee, Dongho Lee, Ki Sung Kang, Jae Jin Kim, and Seung Mok Ryu
- Subjects
Antineoplastic Agents ,Apoptosis ,01 natural sciences ,Biochemistry ,Mice ,Structure-Activity Relationship ,Downregulation and upregulation ,Drug Discovery ,Splenocyte ,medicine ,Tumor Cells, Cultured ,Cytotoxic T cell ,Animals ,Humans ,Viability assay ,Cytotoxicity ,Molecular Biology ,Cyclophosphamide ,Caspase ,Cell Proliferation ,biology ,Dose-Response Relationship, Drug ,Molecular Structure ,010405 organic chemistry ,Chemistry ,Basidiomycota ,Organic Chemistry ,Cancer ,medicine.disease ,Molecular biology ,0104 chemical sciences ,Mice, Inbred C57BL ,010404 medicinal & biomolecular chemistry ,biology.protein ,Drug Screening Assays, Antitumor ,Spleen - Abstract
Eight new naphtho[1,2-c]furan derivatives (1–8) along with six known analogues (9–14) were isolated from culture medium of the basidiomycete Basidioradulum radula. The structures of these compounds were identified using spectroscopic analysis, and their absolute configurations were resolved using X-ray diffraction, ECD, and VCD. Compounds 7 and 14 inhibited the cell viability of human prostate cancer DU-145 cells with IC50 values of 7.54 ± 0.03 μM and 5.04 ± 0.03 μM, respectively. At 8 μM, compounds 7 and 14 increased the percentage of apoptotic cells and upregulated the protein expression related to the apoptosis caspase pathways in DU-145 cells. Furthermore, the hallmarks of cells undergoing apoptosis, such as chromatin condensation, were also observed at this concentration. However, compound 7 and 14 showed no effect on the proliferation of splenocytes isolated from cyclophosphamide-induce immunosuppressed mice.
- Published
- 2021
35. Polyoxygenated sesquiterpenoids from Salvia castanea and their potential anti-Alzheime's disease bioactivities
- Author
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Xu Liu, Yue-Qian Li, Yuanqiang Guo, Wen-Bo Cui, Dong-Qing Fei, Ru-Yue Wang, Feng-Ming Qi, Zhi Dejuan, Komi Djimabi, Zong-Ping Zhang, Xiao-Han Chen, Zhan-Xin Zhang, and Pan-Jie Su
- Subjects
China ,food.ingredient ,Phytochemicals ,Sesquiterpene ,01 natural sciences ,chemistry.chemical_compound ,food ,Alzheimer Disease ,Drug Discovery ,Animals ,Salvia ,Caenorhabditis elegans ,Salvia castanea ,Pharmacology ,biology ,Traditional medicine ,Molecular Structure ,010405 organic chemistry ,Plant Extracts ,Physical health ,General Medicine ,biology.organism_classification ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,Disease Models, Animal ,chemistry ,Herb ,Nubenolide ,Sesquiterpenes - Abstract
Salvia castanea (Family Labiatae), a perennial fragrant herb with castaneous flowers, is mainly distributed in areas with an altitude of 2500–3750 m. The roots of this plant were used as a tea drink by local residents to strengthen physical health. The aim of present study was to acquire secondary metabolites of the ethanol extract obtained from the whole plant of S. castanea and to evaluate their potential anti-Alzheimer's disease. Six new sesquiterpene lactones, salcastanins A-F (1–6), together with three known guaiane-type sesquiterpenoids nubiol (7), nubdienolide (8), and nubenolide (9), were separated from the whole plant of S. castanea. The structures of these compounds were determined by HRESIMS and NMR experiments. The absolute configurations of 1–6 were ascertained by electronic circular dichroism (ECD) experiments. The humanized Caenorhabditis elegans AD pathological model was used to evaluate anti-Alzheimer's disease (AD) activities of 1–9. The results showed the compounds 1–3 and 7 significantly delayed AD-like symptoms of worm paralysis phenotype, which could be used as novel anti-AD candidates.
- Published
- 2020
36. Structural analysis and biological effects of a neutral polysaccharide from the fruits of Rosa laevigata
- Author
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Yuanqiang Guo, Ziteng Song, Caixia Dong, Honglin Wang, Yasushi Ohizumi, Ying Li, Jing Xu, Shaojie Zhang, Jiaojiao Zhang, and Jiahe Bao
- Subjects
Arabinose ,Polymers and Plastics ,Cell ,Mannose ,Antineoplastic Agents ,02 engineering and technology ,010402 general chemistry ,Polysaccharide ,Nitric Oxide ,Rosa ,01 natural sciences ,Immunomodulation ,chemistry.chemical_compound ,Mice ,Cell Movement ,Polysaccharides ,Mole ,Materials Chemistry ,medicine ,Bioassay ,Animals ,Humans ,Immunologic Factors ,Rosa laevigata ,Zebrafish ,Cell Proliferation ,chemistry.chemical_classification ,biology ,Chemistry ,Organic Chemistry ,Monosaccharides ,021001 nanoscience & nanotechnology ,biology.organism_classification ,0104 chemical sciences ,Molecular Weight ,medicine.anatomical_structure ,RAW 264.7 Cells ,Biochemistry ,Galactose ,Fruit ,0210 nano-technology ,K562 Cells ,Reactive Oxygen Species - Abstract
A neutral water-soluble polysaccharide (RLP50-2) was extracted and purified from the fruits of Rosa laevigata. The absolute molecular weight was determined as 1.26 × 104 g/mol. Monosaccharide composition analysis showed that RLP50-2 mainly consisted of glucose, arabinose, and galactose. Structural analysis revealed that RLP50-2 consisted of →5)-α-L-Araf-(1→, →2,5)-α-L-Araf-(1→, →3,5)-α-L-Araf-(1→, →4)-α-D-Glcp-(1→, →6)-α-D-Glcp-(1→, →3,6)-β-D-Glcp-(1→, →4)-α-D-Galp-(1→, →6)-β-D-Galp-(1→, →2)-β-D-Xylp-(1→, terminal α-L-arabinose, and terminal β-D-mannose. Biological assays showed that RLP50-2 had immunomodulatory activities using cell and zebrafish models. Moreover, RLP50-2 showed significantly antitumor activities by inhibiting tumor cell proliferation and migration and blocking angiogenesis. These results suggested that RLP50-2 could be developed as a potential immunomodulatory agent or antitumor candidate drug in biomedicine field.
- Published
- 2020
37. Structural elucidation of an immunological arabinan from the rhizomes of Ligusticum chuanxiong, a traditional Chinese medicine
- Author
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Jiahe Bao, Da-Qing Jin, Shaojie Zhang, Honglin Wang, Namrita Lall, Yuhao Li, Jing Xu, Xiaozhong Lan, Erhao Zhang, Xuelian Wang, Yuanqiang Guo, Anna-Mari Reid, Zhengguo Li, Lijuan Shi, and Lijun An
- Subjects
Arabinose ,Phagocytosis ,Cell ,Interleukin-1beta ,02 engineering and technology ,Polysaccharide ,Nitric Oxide ,Biochemistry ,Chemistry Techniques, Analytical ,03 medical and health sciences ,chemistry.chemical_compound ,Mice ,Structural Biology ,Polysaccharides ,medicine ,Carbohydrate Conformation ,Animals ,Secretion ,Ligusticum ,Molecular Biology ,Zebrafish ,Nuclear Magnetic Resonance, Biomolecular ,030304 developmental biology ,chemistry.chemical_classification ,0303 health sciences ,biology ,Molecular Structure ,Interleukin-6 ,Tumor Necrosis Factor-alpha ,Absolute configuration ,General Medicine ,Macrophage Activation ,021001 nanoscience & nanotechnology ,biology.organism_classification ,In vitro ,Molecular Weight ,medicine.anatomical_structure ,RAW 264.7 Cells ,chemistry ,Carbohydrate Sequence ,Microscopy, Electron, Scanning ,0210 nano-technology ,Reactive Oxygen Species ,Rhizome ,Drugs, Chinese Herbal - Abstract
In the present study, an immunological arabinan, LCP70-2A, was isolated from Ligusticum chuanxiong for the first time. The absolute molecular weight of LCP70-2A was determined to be 6.46 × 104 g/mol using the HPSEC-MALLS-RID method. The absolute configuration of arabinose in LCP70-2A was determined to be L-configuration. Physicochemical characterization revealed that LCP70-2A was a homogeneous polysaccharide and had a backbone of (1 → 5)-linked α-L-Araf with terminal α-L-arabinose residues at position O-2 and O-3. Molecular conformation analysis showed that LCP70-2A was a branching polysaccharide with a compact coil chain conformation in 0.1 M NaCl solution. In addition, in vitro cell assays showed that LCP70-2A can activate macrophages by enhancing the phagocytosis and potentiating the secretion of immunoregulatory factors including NO, TNF-α, IL-6, and IL-1β. Furthermore, LCP70-2A was proved to promote the production of ROS and NO using the zebrafish model, suggesting that LCP70-2A can be further developed as a candidate supplement for immunological enhancement.
- Published
- 2020
38. Structural characteristics and in vitro and in vivo immunoregulatory properties of a gluco-arabinan from Angelica dahurica
- Author
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Jianlin Cui, Yanjun Sun, Linan Zhou, Yuanqiang Guo, Jiahe Bao, Zhengguo Li, Honglin Wang, Lijun An, Yuhao Li, Shaojie Zhang, Jing Xu, Jie Zhang, Da-Qing Jin, and Xuelian Wang
- Subjects
Arabinose ,Phagocytosis ,02 engineering and technology ,Polysaccharide ,Nitric Oxide ,Biochemistry ,Nitric oxide ,03 medical and health sciences ,chemistry.chemical_compound ,Mice ,Structural Biology ,In vivo ,Polysaccharides ,Carbohydrate Conformation ,Animals ,Immunologic Factors ,Secretion ,Molecular Biology ,Zebrafish ,030304 developmental biology ,Angelica ,chemistry.chemical_classification ,0303 health sciences ,biology ,Plant Extracts ,Angelica dahurica ,General Medicine ,Zebrafish Proteins ,021001 nanoscience & nanotechnology ,biology.organism_classification ,In vitro ,RAW 264.7 Cells ,chemistry ,Cytokines ,Inflammation Mediators ,0210 nano-technology ,Reactive Oxygen Species - Abstract
A water-soluble polysaccharide identified here as ADP80-2 was acquired from Angelica dahurica. ADP80-2 was a gluco-arabinan composed of arabinose and a trace of glucose with a molecular weight of 9950 g/mol. The backbone of ADP80-2 comprised →5)-α-L-Araf-(1→, →3, 5)-α-L-Araf-(1→, →6)-α-D-Glcp-(1→, with a terminal branch α-L-Araf-(1 → residue. In terms of immunoregulatory activity, ADP80-2 can significantly promote the phagocytosis, the production of nitric oxide (NO), and the secretion of cytokines (IL-6, IL-1β, and TNF-α) of macrophage. In addition to the cellular immunomodulatory activities, the chemokines related to immunoregulation were significantly increased in the zebrafish model after treated with ADP80-2. These biological results indicated that ADP80-2 with immunomodulatory effects was expected to be useful for the development of new immunomodulatory agents. Simultaneously, the discovery of ADP80-2 further revealed the chemical composition of A. dahurica used as a traditional Chinese medicine and spice.
- Published
- 2020
39. Quality Control of Polycarboxylate Superplasticizer-Gel Permeation Chromatography
- Author
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Yuliang Ke, Yuanqiang Guo, Manyu Su, Zhong Lina, and Yunhui Fang
- Subjects
Gel permeation chromatography ,Water reducer ,chemistry.chemical_classification ,Chromatography ,chemistry ,Computer science ,Superplasticizer ,Molar mass distribution ,Polymer ,Cement paste - Abstract
The control variables were used to study the accuracy of the gel permeation chromatography method, and the changes in polymer molecular weight and molecular weight distribution were studied on different architectures. Then, GPC-molecular weight comparison is performed between the standard sample and the synthetic sample, and the result is compared with the performance of cement paste mixed with water reducer. Gel permeation chromatography (GPC) analysis showed that: The Mn, Mw, and Mw values of the water reducer are different under different variables, and the most affected is the Mw-Mass-average molecular weight of the polymer. By comparison, it was found that the samples showed consistent physical performance results in the GPC and the fluidity of cement paste tests. In this regard, we can evaluate the stable quality of water reducer products through the Mw, it is an accurate and effective method to check the quality of Polycarboxylate superplasticizer products.
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- 2020
40. Ellagic Acid and Its Microbial Metabolite Urolithin A Alleviate Diet-Induced Insulin Resistance in Mice
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Orian S. Shirihai, Zhaoping Li, David Heber, Jieping Yang, Jin Zhong, Jianfeng Long, Yuanqiang Guo, Brenda Chan, Susanne M. Henning, Rebeca Acín-Pérez, and Anton Petcherski
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0301 basic medicine ,Blood Glucose ,Male ,obesity ,Sucrose ,Gene Expression ,Mitochondria, Liver ,Mitochondrion ,chemistry.chemical_compound ,Mice ,Coumarins ,insulin resistance ,2.1 Biological and endogenous factors ,Aetiology ,Microbial metabolite ,Nutrition and Dietetics ,urolithin A ,Diabetes ,Skeletal ,Lipids ,Mitochondria ,medicine.anatomical_structure ,Liver ,Mice, Inbred DBA ,Public Health and Health Services ,Muscle ,Cytokines ,Adiponectin ,Biotechnology ,Ellagic acid ,medicine.medical_specialty ,Carbohydrate metabolism ,Diet, High-Fat ,Article ,03 medical and health sciences ,Insulin resistance ,Food Sciences ,Ellagic Acid ,Internal medicine ,medicine ,Inbred DBA ,Animals ,Muscle, Skeletal ,Metabolic and endocrine ,Nutrition ,Inflammation ,030109 nutrition & dietetics ,Nutrition & Dietetics ,Skeletal muscle ,Metabolism ,medicine.disease ,Lipid Metabolism ,Urolithin ,Diet ,High-Fat ,030104 developmental biology ,Endocrinology ,chemistry ,Insulin Resistance ,Food Science - Abstract
SCOPE: We aimed at evaluating the effect of dietary ellagic acid (EA) and its microbial metabolite urolithin A (UA) on glucose metabolism and insulin resistance (IR) in mice with diet-induced IR. METHODS AND RESULTS: DBA2J mice were fed a high fat/high sucrose diet (HF/HS) for 8 weeks to induce IR and then 0.1% EA, UA, or EA and UA combined (EA+UA) were added to the HF/HS-diet for another 8 weeks. UA significantly decreased fasting glucose and increased serum adiponectin compared with HF/HS-controls. During intraperitoneal insulin tolerance test, EA+UA significantly improved insulin-mediated glucose lowering effects at 15 and 120 min and reduced blood triglycerides compared with HF/HS-controls. Serum free fatty acids were significantly decreased by EA, UA and EA+UA. We observed differential expression of genes related to mitochondrial function by EA, UA and EA+UA in liver and skeletal muscle. Primary hepatocytes from IR-mice had higher proton leak, basal and ATP-linked oxygen consumption rates compared with healthy controls. EA and EA+UA but not UA reduced the proton leak in hepatocytes from IR-mice. CONCLUSION: EA and UA induced different metabolic benefits in HF/HS diet induced IR mice. The effects of EA and UA on mitochondrial function suggest a potentially novel mechanism modulating metabolism. This article is protected by copyright. All rights reserved.
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- 2020
41. Nitric oxide inhibitory iridoids as potential anti-inflammatory agents from Valeriana jatamansi
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Jing Xu, Peng Wu, Jie Zhang, Ziteng Song, Muhetaer Tuerhong, Yuanqiang Guo, Zhaoyu Shi, Honghong Xing, and Huimei Wang
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Circular dichroism ,medicine.drug_class ,Stereochemistry ,Valeriana jatamansi ,Anti-Inflammatory Agents ,Inflammation ,Inhibitory postsynaptic potential ,Nitric Oxide ,01 natural sciences ,Biochemistry ,Anti-inflammatory ,Nitric oxide ,chemistry.chemical_compound ,Mice ,Structure-Activity Relationship ,Valerian ,Drug Discovery ,medicine ,Ic50 values ,Animals ,Humans ,Iridoids ,Molecular Biology ,Biological evaluation ,Molecular Structure ,010405 organic chemistry ,Chemistry ,Organic Chemistry ,0104 chemical sciences ,Molecular Docking Simulation ,010404 medicinal & biomolecular chemistry ,medicine.symptom - Abstract
Five new iridoids, jatadomins A−E (1–5), together with six known analogues (6–11) and one known sesquiterpenoid (12), were isolated from the roots of Valeriana jatamansi Jones. Their structures were determined by analysis of their NMR, HRESIMS, and electronic circular dichroism calculations (ECD) data. The biological evaluation revealed that compounds 1–6 had anti-inflammatory activities by inhibiting nitric oxide (NO) release in LPS-induced murine microglial BV-2 cells, with IC50 values of 24.4, 9.2, 21.2, 25.9, 30.6, and 0.4 μM, respectively. Further molecular docking studies revealed a potential mechanism for NO inhibition by the bioactive compounds.
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- 2020
42. Three new guaiane-type sesquiterpenoids and a monoterpenoid from Litsea lancilimba Merr
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Xian-peng Ma, Ishaq Muhammad, Shi-Kai Yan, Hui-Zi Jin, Xue Xiao, Yong Zhen Xiao, Syed Shams ul Hassan, and Yuanqiang Guo
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Litsea ,biology ,010405 organic chemistry ,Chemistry ,Organic Chemistry ,Plant Science ,Lauraceae ,biology.organism_classification ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,Analytical Chemistry ,010404 medicinal & biomolecular chemistry ,Botany - Abstract
Three undescribed guaiane-type sesquiterpenes (1–3), and a monoterpenoid (4) along with eleven known compounds (5 − 15) were isolated from the crude extract of Litsea lancilimba Merr. The structures of all the isolated compounds were extensively elucidated on the basis of comprehensive spectroscopic techniques (HRESIMS, 1 D NMR, and 2 D NMR). Their relative and absolute configurations were comprehensively established by NOESY spectroscopy, circular dichroism (ECD) and the calculated ECD analysis. All the isolates were tested for anti-inflammatory activity by measuring the amount of nitric oxide production. Amongst tested compounds, compounds 1 − 3 exhibited moderate inhibitory activities against the production of nitric oxide with IC50 value of 35.5, 32.1, 46.7 μM in RAW264.7 cells stimulated by LPS, respectively.
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- 2020
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43. NMR and MS data for novel bioactive constituents from Pugionium cornutum L. Gaertn
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Lu Qu, Yi Zhang, Tao Wang, Chang Zheng, Zhijuan Ding, Jiejing Yan, Wenzhong Shi, Yuanqiang Guo, and Jingya Ruan
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0303 health sciences ,Multidisciplinary ,Traditional medicine ,Chemistry ,Pugionium cornutum L. Gaertn ,lcsh:Computer applications to medicine. Medical informatics ,Intestinal motility ,03 medical and health sciences ,Thiohydantoin derivatives ,0302 clinical medicine ,Pugionium cornutum ,lcsh:R858-859.7 ,Research article ,Traditional Mongolian medicine ,lcsh:Science (General) ,Two-dimensional nuclear magnetic resonance spectroscopy ,030217 neurology & neurosurgery ,lcsh:Q1-390 ,030304 developmental biology ,Novel bioactive constituents - Abstract
The data presented in this article are associated with the research article entitled “Bioactive Constituents Study of Pugionium cornutum L. Gaertn on Intestinal Motility” [1]. The aim of this data was to provide the 1D, 2D NMR and MS spectrum of novel bioactive compounds from P. cornutum. Keywords: Traditional Mongolian medicine, Pugionium cornutum L. Gaertn, Novel bioactive constituents, Thiohydantoin derivatives
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- 2020
44. Chemical Constituents of the Leaves of Butterbur (Petasites japonicus) and Their Anti-Inflammatory Effects
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Dongho Lee, Seung Mok Ryu, Jin Su Lee, Yuanqiang Guo, Jun Lee, Dae Sik Jang, Jung Hye Choi, Sangsu Park, Ziteng Song, and Miran Jeong
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lignan ,Lipopolysaccharides ,Circular dichroism ,medicine.drug_class ,Stereochemistry ,Anti-Inflammatory Agents ,PGE2 ,Nitric Oxide Synthase Type II ,Asteraceae ,Nitric Oxide ,01 natural sciences ,Biochemistry ,Anti-inflammatory ,Article ,Dinoprostone ,Lignans ,NO ,chemistry.chemical_compound ,Mice ,medicine ,Animals ,Molecular Biology ,chemistry.chemical_classification ,Lignan ,biology ,010405 organic chemistry ,Plant Extracts ,Petasites japonicus ,molecular docking ,Petasites ,COX-2 ,anti-inflammation ,0104 chemical sciences ,Nitric oxide synthase ,iNOS ,Plant Leaves ,010404 medicinal & biomolecular chemistry ,Enzyme ,RAW 264.7 Cells ,chemistry ,Cyclooxygenase 2 ,Vibrational circular dichroism ,biology.protein ,Lactone - Abstract
Two new aryltetralin lactone lignans, petasitesins A and B were isolated from the hot water extract of the leaves of butterbur (Petasites japonicus) along with six known compounds. The chemical structures of lignans 1 and 2 were elucidated on the basis of 1D and 2D nuclear magnetic resonance (NMR) spectroscopic data, electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) spectra. Petasitesin A and cimicifugic acid D showed significant inhibitory effects on the production of both prostaglandin E2 (PGE2) and NO in RAW264.7 macrophages. The expressions of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) were inhibited by compound 1 in RAW264.7 cells. Furthermore, compounds 1 and 3 exhibited strong affinities with both iNOS and COX-2 enzymes in molecular docking studies.
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- 2019
45. Seco-labdane diterpenoids from the leaves of Callicarpa nudiflora showing nitric oxide inhibitory activity
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Dongho Lee, Yuanqiang Guo, Jing Xu, Chunfeng Xie, Jinghan Wang, Xueyuan Yang, Jie Zhang, Xiaocong Sun, Yasushi Ohizumi, Feng Liu, Bangjian Dong, and Da Qing Jin
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Lipopolysaccharides ,Stereochemistry ,Nitric Oxide Synthase Type II ,Plant Science ,Horticulture ,Callicarpa ,Nitric Oxide ,Inhibitory postsynaptic potential ,01 natural sciences ,Biochemistry ,Nitric oxide ,Labdane ,Mice ,chemistry.chemical_compound ,Animals ,Nuclear Magnetic Resonance, Biomolecular ,Molecular Biology ,Callicarpa nudiflora ,Molecular Structure ,biology ,010405 organic chemistry ,Verbenaceae ,General Medicine ,biology.organism_classification ,Circular dichroism spectra ,0104 chemical sciences ,Plant Leaves ,Nitric oxide synthase ,010404 medicinal & biomolecular chemistry ,chemistry ,biology.protein ,Microglia ,Diterpenes ,Two-dimensional nuclear magnetic resonance spectroscopy ,Drugs, Chinese Herbal - Abstract
Nine previously undescribed seco-labdane diterpenoids, nudiflopenes A−I, were isolated from the leaves of Callicarpa nudiflora. Their structures were elucidated on the basis of extensive 1D and 2D NMR spectroscopic data analysis, and the absolute configurations of these compounds were established by the modified Mosher's method and experimental and calculated electronic circular dichroism spectra. Nudiflopenes A−I belong to the class of seco-labdane diterpenoids. All of the isolates showed inhibitory activities on lipopolysaccharide-induced nitric oxide (NO) production in murine microglial BV-2 cells. The possible mechanism of NO inhibition of some bioactive compounds was also investigated using molecular docking, which revealed interactions of bioactive compounds with the inducible nitric oxide synthase (iNOS) protein.
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- 2018
46. NO inhibitory constituents as potential anti-neuroinflammatory agents for AD from Blumea balsamifera
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Zhaoyu Shi, Yasushi Ohizumi, Bangjian Dong, Jing Xu, Dongho Lee, Jun Ma, Quanhui Ren, Da Qing Jin, Yuanqiang Guo, and Jie Zhang
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Circular dichroism ,Stereochemistry ,Nitric Oxide Synthase Type II ,Asteraceae ,Nitric Oxide ,Inhibitory postsynaptic potential ,01 natural sciences ,Biochemistry ,Cell Line ,Nitric oxide ,Labdane ,Mice ,chemistry.chemical_compound ,Drug Discovery ,Animals ,Inos protein ,Molecular Biology ,No release ,Molecular Structure ,biology ,Terpenes ,010405 organic chemistry ,Chemistry ,Anti-Inflammatory Agents, Non-Steroidal ,Organic Chemistry ,Plant Components, Aerial ,biology.organism_classification ,Terpenoid ,0104 chemical sciences ,Molecular Docking Simulation ,010404 medicinal & biomolecular chemistry ,Neuroprotective Agents ,Microglia ,Blumea balsamifera - Abstract
Our continuous search for new nitric oxide (NO) inhibitory substances as anti-neuroinflammatory agents for AD resulted in the isolation of one new labdane diterpenoid and three new guaiane sesquiterpenoids, as well as ten known compounds from Blumea balsamifera. Their structures were elucidated by NMR spectroscopic data analysis and the time-dependent density functional theory (TDDFT) electronic circular dichroism (ECD) calculations. The anti-neuroinflammatory effects were examined by inhibiting NO release in LPS-induced murine microglial BV-2 cells. The possible mechanism of NO inhibition of some bioactive compounds was also investigated using molecular docking, which revealed the interactions of bioactive compounds with the iNOS protein.
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- 2018
47. Nitric oxide inhibitors with a spiro diterpenoid skeleton from Scutellaria formosana : Structures, NO inhibitory effects, and interactions with iNOS
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Yuanqiang Guo, Peixia Wang, Dongho Lee, Da Qing Jin, Yue Liang, Jing Xu, Yasushi Ohizumi, Xueyuan Yang, Guochen Su, Feng Liu, and Muhetaer Tuerhong
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Circular dichroism ,Scutellaria ,Stereochemistry ,Nitric Oxide Synthase Type II ,Nitric Oxide ,Inhibitory postsynaptic potential ,01 natural sciences ,Biochemistry ,Cell Line ,Nitric oxide ,Mice ,chemistry.chemical_compound ,Catalytic Domain ,Drug Discovery ,Animals ,Inos protein ,Molecular Biology ,Molecular Structure ,biology ,010405 organic chemistry ,Organic Chemistry ,Plant Components, Aerial ,biology.organism_classification ,Terpenoid ,0104 chemical sciences ,Molecular Docking Simulation ,010404 medicinal & biomolecular chemistry ,chemistry ,Phytochemical ,Microglia ,Diterpenes ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
A phytochemical investigation to obtain new NO inhibitors resulted in the isolation of five new spiro diterpenoids (1 −5) from the aerial parts of Scutellaria formosana. The structures were elucidated on the basis of extensive 1D and 2D NMR spectroscopic data analysis, and the absolute configurations of these compounds were established via comparison of experimental and calculated electronic circular dichroism (ECD) spectra. The nitric oxide (NO) inhibitory effects were evaluated and all of the compounds showed inhibitory effects on lipopolysaccharide-induced NO production in murine microglial BV-2 cells. The possible mechanism of NO inhibition of bioactive compounds was also investigated using molecular docking, which revealed the interactions of bioactive compounds with the iNOS protein.
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- 2018
48. Structural elucidation and immunomodulatory evaluation of a polysaccharide from Stevia rebaudiana leaves
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Zhengguo Li, Zhaoyu Shi, Yuanqiang Guo, Shaojie Zhang, Munira Abudukeremu, Lijun An, Jiahe Bao, Jing Xu, and Muhetaer Tuerhong
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Arabinose ,Mannose ,Polysaccharide ,01 natural sciences ,Analytical Chemistry ,Nitric oxide ,chemistry.chemical_compound ,0404 agricultural biotechnology ,Polysaccharides ,Animals ,Stevia ,Zebrafish ,chemistry.chemical_classification ,Monosaccharides ,010401 analytical chemistry ,04 agricultural and veterinary sciences ,General Medicine ,Nuclear magnetic resonance spectroscopy ,040401 food science ,0104 chemical sciences ,Plant Leaves ,Stevia rebaudiana ,chemistry ,Biochemistry ,Galactose ,ARAF ,Food Science - Abstract
Stevia rebaudiana, a sweetener with medicinal functions, has attracted extensive attention due to its application in food and pharmaceutical fields. However, a few studies were performed to explore polysaccharides in this plant. Herein, SRP70-1 was derived from S. rebaudiana. Structural analysis (monosaccharide composition analysis, high-performance liquid chromatography-multi-angle light scattering detection, gas chromatography-mass spectrometry, and nuclear magnetic resonance spectroscopy) revealed that SRP70-1 was composed of mannose, glucose, galactose, and arabinose at the molar ratio of 1.35:1.00:3.23:3.47, with an absolute molecular weight of 7698 Da. SRP70-1 was found to contain → 5)-α- l -Araf-(1→, →2,3,5)-α- l -Araf-(1→, →4)-β- l -Arap-(1→, →4)-β- d -Galp-(1→, →6)-β- d -Galp-(1→, →4)-β- d -Manp-(1→, →6)-β- d -Manp-(1→, and terminal α- l -Araf, β- d -Galp, and β- d -Glcp residues. Cell experiments showed that SRP70-1 could significantly promote phagocytosis and increase the release of nitric oxide and cytokines including IL-1β, IL-6, and TNF-α. Further zebrafish experiments confirmed the immunological enhancement effects of SRP70-1. This study revealed that SRP70-1 may be useful for the development of functional foods.
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- 2021
49. A dandelion polysaccharide and its selenium nanoparticles: Structure features and evaluation of anti-tumor activity in zebrafish models
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Linan Zhou, Yasushi Ohizumi, Jing Xu, Ziteng Song, Da-Qing Jin, Yuanqiang Guo, Shaojie Zhang, Yuhao Li, Lijuan Shi, Jianlin Cui, and Jie Zhang
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Taraxacum ,Polymers and Plastics ,Angiogenesis ,Antineoplastic Agents ,Apoptosis ,Dandelion ,02 engineering and technology ,010402 general chemistry ,01 natural sciences ,HeLa ,Selenium ,Polysaccharides ,In vivo ,Neoplasms ,Materials Chemistry ,Animals ,Humans ,Zebrafish ,Cell Proliferation ,biology ,Chemistry ,Organic Chemistry ,Hydrogen Bonding ,Hep G2 Cells ,021001 nanoscience & nanotechnology ,biology.organism_classification ,In vitro ,Fructans ,0104 chemical sciences ,Cell biology ,A549 Cells ,Cancer cell ,Nanoparticles ,0210 nano-technology ,HeLa Cells - Abstract
In this study, an inulin fructan (TMP50-2) with moderate anti-tumor activity was obtained from dandelion. To further improve the anti-tumor activity of TMP50-2, a monodisperse and stable spherical nanoparticle (Tw-TMP-SeNP, 50 nm) was fabricated. Physico-chemical analysis revealed that TMP50-2 and Tween 80 were tightly wrapped on the surface of SeNPs by forming C O⋯Se bonds or through hydrogen bonding interaction (O H⋯Se). In vitro anti-tumor assay showed that Tw-TMP-SeNP treatment could significantly inhibit the proliferation of cancer cells (HepG2, A549, and HeLa) in a dose-dependent manner, while HepG2 cells were more susceptible to Tw-TMP-SeNP with an IC50 value of 46.8 μg/mL. The apoptosis induction of HepG2 cells by Tw-TMP-SeNP was evidenced by increasing the proportion of apoptotic cells ranging from 12.5% to 27.4%. Furthermore, in vivo zebrafish model confirmed the anti-tumor activity of Tw-TMP-SeNP by inhibiting the proliferation and migration of tumor cells as well as the angiogenesis of zebrafish embryos.
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- 2021
50. Chemical Constituents Isolated from the Leaves of Toricellia angulata Oliv. var. intermedia (Harms.) Hu
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Zhong-Yao Han, Zheng-Min Yang, Yuanqiang Guo, Fang Cao, Yan Li, Yue-Sheng Yu, and Fu-Jun Zhou
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Pharmacology ,Toricellia angulata ,Complementary and alternative medicine ,Traditional medicine ,Chemistry ,Chemical constituents ,Drug Discovery ,Plant Science ,General Medicine ,Intermedia ,Chemical composition - Abstract
In our survey on the chemical composition of Chinese folk medicines, nine compounds were isolated from methanol extract of the leaves of Toricellia angulata Oliv. var. intermedia (Harms.) Hu (Corniaceae). The structures of these compounds were elucidated on the basis of NMR data analysis, which were identified as dimethyl 2-(hydroxymethyl)-5-oxocyclohexane-1,4-dicarboxylate (1), methyl succinate (2), 5-hydroxymethyl-2-furfuraldehyde (3), 7-hydroxy-6-methoxycoumarin (4), loliolide (5), (8 S)-deca-2-trans-2,9-diene-4,6-diyn-1,8-diol (6), methyl malate (7), griselinoside (8), and methyl linoleate (9), respectively. Among them, compound 1 is a new cyclohexanone derivative and given a trivial name torriangulate A, while others are categorized to be organic acids (2, 7, and 9), a coumarin derivative (4), a terpene lactone (5), a polyacetylene (6), and an iridoid glycoside (8). Compounds 3–5 were isolated from this genus for the first time and compound 9 was first identified from this species. The discovered compounds with novel or known structures further reveal the chemical basis of T. angulata var . intermedia, which lays a foundation for the development of T. angulata var . intermedia used as a traditionally folk medicine.
- Published
- 2021
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