70 results on '"Ya-nan Yang"'
Search Results
2. Photoinduced Irreversible Intramolecular Proton Transfer of Arnebinones B, D, and E: The Case of Photoenolization at the p-Benzoquinone-CH2/CH-π System
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Ya-Nan Yang, Xu Zhang, Hai-Wei Yan, Xiang Yuan, Pei-Cheng Zhang, and Ling-Hao Zhao
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Pharmacology ,chemistry.chemical_classification ,Double bond ,Proton ,Organic Chemistry ,Pharmaceutical Science ,Planar chirality ,Photochemistry ,Benzoquinone ,Analytical Chemistry ,Complementary and alternative medicine ,chemistry ,Intramolecular force ,Drug Discovery ,Molecular Medicine ,Common key ,Moiety ,Epimer - Abstract
Arnebinones B, E, and D (1-3) have been found to be sensitive to light, generating complex and diverse proton transfer products when triggered by light. A unique two-step irreversible intramolecular proton transfer of 1 produced five scalemic mixtures, of which four possessed intriguing dual planar chirality. The unprecedented orientation epimerization equilibrium of the intra-annular double bond was first observed and researched in the homologous meroterpenoids by HPLC monitoring and DFT calculations. A "p-benzoquinone-CH2/CH-π" moiety in the structure was the common key feature for the occurrence of this type of photoenolization reaction. The product transformation processes and universality of this photoinduced irreversible proton transfer reaction were analyzed together with the cytotoxic activities of arnebinones B, D, and E, and their photoreaction products.
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- 2021
3. Eight new arnebinol B-based meroterpenoids with planar chirality in the constrained 6/10/5 tricyclic skeleton from Arnebia euchroma and their cytotoxicities
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Hai-Wei Yan, Ya-Nan Yang, Xu Zhang, Jian-Shuang Jiang, Xiang Yuan, Zi-Ming Feng, and Pei-Cheng Zhang
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Molecular Structure ,Terpenes ,Organic Chemistry ,Drug Discovery ,Boraginaceae ,Molecular Biology ,Biochemistry ,Plant Roots ,Skeleton - Abstract
Eight new arnebinol B-based meroterpenoids ((-)-1, 2, 3, (-)-5, and 7-10) with a constrained 6/10/5 tricyclic backbone were isolated from the roots of Arnebia euchroma. The planar and steric structures of these new compounds were unambiguously elucidated by extensive spectroscopic analyses, X-ray diffraction crystallography, and ECD calculations. The predominant relative orientation between H-7 and the Z double bond with a methyl substituent in the rigid 10-membered carbocycle, along with the planar chirality of the Z double bond was analyzed and discussed for the first time. The illustration of the planar chirality derived from the Z double bond should be paid great importance during the structure elucidation on these homologous meroterpenoids. All the isolated meroterpenoids were screened for their cytotoxicities against the HCT-8, PANC-1, HGC-27, HepG2, and PC9 cell lines, and compounds (+)-5 and (-)-5 exhibited the most potent cytotoxicity.
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- 2022
4. Bioactive amides from Polygonum cuspidatum
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Zi-Ming Feng, Jian-Shuang Jiang, Fu Liu, Ya-Nan Yang, Xu Zhang, and Pei-Cheng Zhang
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Pharmacology ,biology ,010405 organic chemistry ,Stereochemistry ,Chemistry ,Organic Chemistry ,Pharmaceutical Science ,General Medicine ,biology.organism_classification ,01 natural sciences ,Nmr data ,Polygonaceae ,0104 chemical sciences ,Analytical Chemistry ,Rhizome ,010404 medicinal & biomolecular chemistry ,Complementary and alternative medicine ,Drug Discovery ,Molecular Medicine ,Enantiomer ,POLYGONUM CUSPIDATUM - Abstract
One pair of new amides enantiomers (1a and 1b) and two known amides were isolated from the rhizomes of Polygonum cuspidatum. Their structures were established using UV, IR, HRESIMS, and NMR data. Notably, compound 1 possesses unique C-C connection between feruloyltyramine and resveratrol. Their absolute configurations were determined by the ECD method. All compounds were evaluated for their α-glucosidase inhibitory activity and compounds 2 and 3 showed significant inhibitory activity with IC50 values of 2.82 and 13.06 μmol/L, respectively (positive control acarbose, IC50 385 μmol/L).
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- 2021
5. Three new monocyclic monoterpenoid O-glycosides from the roots of Glycyrrhiza uralensis
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Jian-Shuang Jiang, Ya-Nan Yang, Xu Zhang, Yuan Meng, Zi-Ming Feng, and Pei-Cheng Zhang
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Pharmacology ,chemistry.chemical_classification ,biology ,010405 organic chemistry ,Stereochemistry ,Chemistry ,Organic Chemistry ,Glycyrrhiza uralensis ,Pharmaceutical Science ,Glycoside ,General Medicine ,biology.organism_classification ,01 natural sciences ,0104 chemical sciences ,Analytical Chemistry ,010404 medicinal & biomolecular chemistry ,Complementary and alternative medicine ,Drug Discovery ,Molecular Medicine ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
Three new monocyclic monoterpenoid containing β-D-apiofuranosyl-(1→2)-O-β-D-glucopyranosyl moieties, together with three other known monocyclic monoterpenoid O-glycosides, were obtained from the roots of Glycyrrhiza uralensis for the first time. Their structures were determined by UV, IR, HRESIMS, and 1D and 2D NMR data.
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- 2020
6. Three new compounds from the rhizome of Ligusticum chuanxiong and their anti-inflammation activities
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Jian-Shuang Jiang, Xiang Yuan, Pei-Cheng Zhang, Ya-Nan Yang, Bin Han, and Zi-Ming Feng
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Pharmacology ,Apiaceae ,Ligusticum chuanxiong ,Traditional medicine ,biology ,010405 organic chemistry ,Organic Chemistry ,Pharmaceutical Science ,Anti inflammation ,General Medicine ,biology.organism_classification ,01 natural sciences ,0104 chemical sciences ,Analytical Chemistry ,Rhizome ,Nitric oxide ,010404 medicinal & biomolecular chemistry ,chemistry.chemical_compound ,Complementary and alternative medicine ,chemistry ,Phytochemical ,Drug Discovery ,Curcumin ,Molecular Medicine ,Spectral data - Abstract
Phytochemical investigation of the rhizome of Ligusticum chuanxiong Hort led to the isolation and identification of three new compounds, chuanxiongoside A, (2E,4E)-8-(6-O-inositolyl)-8-oxo-2,7-dimethyl-octadienoic acid (2), chuanxiongoside C (3). The structures of these compounds were unambiguously established by HR-ESI-MS, UV, IR, CD, NMR spectral data and comparison to reported data. All the isolated compounds (1-3) were investigated for their inhibitory effects on nitric oxide (NO) production in LPS-induced RAW 264.7 cells. All compounds showed excellent inhibition of NO production stronger than curcumin. [Formula: see text].
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- 2020
7. 1,2-Dibromoethane and KI mediated α-acyloxylation of ketones with carboxylic acids
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Xujie Wang, Ya-Nan Yang, Zi-Ming Feng, Pei-Cheng Zhang, Jian-Shuang Jiang, and Gangsheng Li
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Reaction mechanism ,Compatibility (geochemistry) ,02 engineering and technology ,General Chemistry ,010402 general chemistry ,021001 nanoscience & nanotechnology ,01 natural sciences ,0104 chemical sciences ,chemistry.chemical_compound ,chemistry ,Transition metal ,1,2-Dibromoethane ,Organic chemistry ,0210 nano-technology - Abstract
The 1,2-dibromoethane- and KI-mediated α-acyloxylation of ketones is reported in moderate to good yield without the use of transition metals and strong oxidants. Various acids are well tolerated with wide functional group compatibility. An 1,2-dibromoethane- and KI-catalysed reaction mechanism is proposed based on the results of control experiments.
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- 2020
8. Archromones A–F, unusual polycyclic dearomatic geranylquinol derivatives from the roots of Arnebia euchroma
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Hai-Wei Yan, Zi-Ming Feng, Pei-Cheng Zhang, Ya-Nan Yang, Xu Zhang, and Jian-Shuang Jiang
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biology ,010405 organic chemistry ,Stereochemistry ,Chemistry ,Arnebia euchroma ,Organic Chemistry ,Absolute configuration ,Hydronaphthalene ,biology.organism_classification ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,HeLa ,010404 medicinal & biomolecular chemistry ,Ic50 values ,Moiety ,Physical and Theoretical Chemistry ,Cytotoxicity - Abstract
Eight new geranylquinol derivatives (1-8) were purified from the roots of Arnebia euchroma. Compounds 1-6 possess an unprecedented dearomatic benzocogeijerene skeleton with a rare trans-fused hydronaphthalene moiety. Their structures and absolute configurations were elucidated by HRESIMS, NMR, ECD, and X-ray diffraction. A convenient strategy for rapid determination of the relative configuration of H-1/H-7/Me-16 and the absolute configuration at C-1 for 1-6 was summarized. Compound 2 exhibited cytotoxicity against all the tested cell lines, namely PC9, BGC823, HCT116, HepG2, HeLa, and U87-MG, with IC50 values ranging from 13.7 to 29.3 μM.
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- 2020
9. Two dimers generated by lithospermic decarboxylation coupling from Danshen
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Quan-Chang, Gu, Xiao-Li, Wei, Qing, Ji, Zi-Ming, Feng, Jian-Shuang, Jiang, Xu Zhang, Xiang, Yuan, Xiao-Wei, Zhang, Pei-Cheng, Zhang, and Ya-Nan, Yang
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Matrix Metalloproteinase 9 ,Organic Chemistry ,Drug Discovery ,Salvia miltiorrhiza ,Decarboxylation ,Plant Roots ,Molecular Biology ,Biochemistry ,Rhizome - Abstract
To further reveal the active ingredients of Danshen, we systematically studied its chemical components and obtained two new lithospermic acid derivatives (compounds 1 and 2) together with five known phenylpropionic acids (compounds 3-7) from the dried rhizomes of Salvia miltiorrhiza. The structures of the two new compounds were determined by multiple spectral analyses (UV, IR, HR-ESI-MS, NMR, and ECD). In addition, the absolute configurations were established by chiral analysis and calculated and experimental circular dichroism spectra. Biological research indicated that compound 1 could significantly inhibit the proliferation of isoproterenol (ISO)-treated cardiac fibroblasts (AC16 cells), and MMP9 was found to be the most likely target of compound 1. The protein expression and mRNA levels of MMP9 were increased in ISO-induced AC16 cells, which could be reversed by treatment with compound 1. Furthermore, this treatment could alleviate the migration and activation of ISO-induced cardiac fibroblasts.
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- 2022
10. Two new lignans from the fruits of Forsythia suspensa
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Jun Cao, Zi-Ming Feng, Si-Yuan Shao, Xiang Yuan, Pei-Cheng Zhang, Ya-Nan Yang, Xu Zhang, and Jian-Shuang Jiang
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Pharmacology ,Forsythia suspensa ,biology ,Traditional medicine ,010405 organic chemistry ,Chemistry ,Organic Chemistry ,Pharmaceutical Science ,Moderate activity ,General Medicine ,biology.organism_classification ,01 natural sciences ,0104 chemical sciences ,Analytical Chemistry ,010404 medicinal & biomolecular chemistry ,Complementary and alternative medicine ,Drug Discovery ,Molecular Medicine - Abstract
Two new lignans, wikstronoside B (1) and forsysesquinorlignan (2), were isolated from the fruits of Forsythia suspensa, along with two known sesquineolignans, hedyotol A and hedyotol C (3 and 4). The structures of new compounds were established via extensive spectroscopy techniques, including UV, IR, HRESIMS, NMR, and ECD. Compounds 3 and 4 were isolated from this plant for the first time. Their anti-inflammatory effects were evaluated via a detection model with LPS-induced murine macrophage RAW264.7 cells, and compound 3 showed a moderate activity.
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- 2019
11. A concise approach for determining the relative configuration of H-7 and H-8 in 8,4′-oxyneolignans by 1H NMR spectroscopy
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Zi-Ming Feng, Jian-Shuang Jiang, Peng-Fei Yang, Bing Han, Ya-Nan Yang, and Pei-Cheng Zhang
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1h nmr spectroscopy ,Key point ,010405 organic chemistry ,Chemistry ,Computational chemistry ,Organic Chemistry ,Molecular configuration ,010402 general chemistry ,01 natural sciences ,0104 chemical sciences - Abstract
The determination of molecular configuration is usually a difficult and key point in the structure elucidation of natural products. However, due to the small number of available samples and the multiple chiral centers and complex structures of natural products, it is difficult to rapidly and accurately determine their relative configurations. In this paper, we use an NMR technique to comprehensively study 8,4′-oxyneolignan glucosides and find that the chemical shift difference between H-9a and H-9b can be used to accurately and rapidly determine the relative configuration of H-7 and H-8. Our finding can be directly applied to 8,4′-oxyneolignan glucosides without the need for hydrolysis.
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- 2019
12. Stereospecific acyloin ring contraction controlled by glucose and concise total synthesis of saffloneoside
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Xiang Yuan, Pei-Cheng Zhang, Zi-Ming Feng, Ya-Nan Yang, Zhong Chen, Xu Zhang, Wan Gao, and Jian-Shuang Jiang
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Contraction (grammar) ,biology ,010405 organic chemistry ,Chemistry ,Stereochemistry ,Organic Chemistry ,Carthamus ,Total synthesis ,010402 general chemistry ,biology.organism_classification ,01 natural sciences ,0104 chemical sciences ,Stereospecificity ,Moiety - Abstract
Saffloneoside (1), a structurally unusual p-hydroxycinnamylcyclopentenone C-glucoside obtained from the florets of Carthamus tinctorius, was synthesized on a gram scale in seven steps. A stereospecific acyloin ring contraction controlled by the chirality of glucose moiety at the C5 position of highly substituted cyclohexadienones was discovered. The possible β-orientation hydrogen migration mechanism in the transformation of C5(sp2) into C5(sp3) was proposed.
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- 2019
13. Neuroprotective and anti-inflammatory phenylethanoidglycosides from the fruits of Forsythia suspensa
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Zi-Meng Feng, Pei-Cheng Zhang, Ya-Nan Yang, Fan Zhang, Jian-Shuang Jiang, and Si-Yuan Shao
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Lipopolysaccharides ,medicine.drug_class ,Cell Survival ,Anti-Inflammatory Agents ,Molecular Conformation ,Pharmacology ,01 natural sciences ,Biochemistry ,Neuroprotection ,PC12 Cells ,Anti-inflammatory ,chemistry.chemical_compound ,Mice ,Drug Discovery ,medicine ,Animals ,Viability assay ,Glycosides ,Molecular Biology ,IC50 ,Forsythia ,Neuroinflammation ,Forsythia suspensa ,biology ,010405 organic chemistry ,Plant Extracts ,Tumor Necrosis Factor-alpha ,Macrophages ,Organic Chemistry ,Rotenone ,biology.organism_classification ,0104 chemical sciences ,Rats ,010404 medicinal & biomolecular chemistry ,Neuroprotective Agents ,RAW 264.7 Cells ,chemistry ,Fruit ,Tumor necrosis factor alpha - Abstract
Neuroinflammation is emerging as a crucial reason of major neurodegenerative diseases in recent years. Increasingly evidences have supported that bioactive natural products from traditional Chinese medicines have efficiency for neuroinflammation. Forsythia suspensa, a typical medicinal herb, showed potential neuroprotective and anti-inflammatory properties in previous pharmacological studies. In our research to obtain neuroprotective and anti-inflammatory natural products, three unprecedented C6–C7′/C6–C16′ linked phenylethanoid glycoside dimers (1–3), three new phenylethanoid glycosides (4–6), and six known compounds (7–12) were isolated from the fruits of Forsythia suspensa. Their structures were determined by comprehensive spectroscopic data and comparison to the literature data. All isolated compounds were evaluated their neuroprotective and anti-inflammatory activities. Compounds 1 and 10 exhibited significant neuroprotective activities with the cell viability values of 75.24 ± 8.05% and 93.65 ± 10.17%, respectively, for the serum-deprivation and rotenone induced pheochromocytoma (PC12) cell injury. Meanwhile, compound 1 exhibited excellent anti-inflammatory activity against tumor necrosis factor (TNF)-α expression in LPS induced RAW264.7 cells with the IC50 value of 1.30 μM. This study revealed that the bioactive phenylethanoid glycosides may attenuate neuroinflammation through their neuroprotective and anti-inflammatory activities.
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- 2021
14. Chemical constituents of Ligusticum chuanxiong and their anti-inflammation and hepatoprotective activities
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Jian-Shuang Jiang, Ya-Nan Yang, Xiang Yuan, Zi-Ming Feng, Bing Han, and Pei-Cheng Zhang
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Lipopolysaccharides ,Ligusticum chuanxiong ,Anti-Inflammatory Agents ,Nitric Oxide ,01 natural sciences ,Biochemistry ,chemistry.chemical_compound ,Mice ,Drug Discovery ,Animals ,Humans ,Ligusticum ,Phenols ,No production ,Spectral data ,Molecular Biology ,Traditional medicine ,010405 organic chemistry ,Chemistry ,Spectrum Analysis ,Organic Chemistry ,Anti inflammation ,Hep G2 Cells ,0104 chemical sciences ,Rhizome ,010404 medicinal & biomolecular chemistry ,RAW 264.7 Cells ,Liver ,Chemical constituents ,Curcumin - Abstract
Ligusticum chuanxiong Hort is a famous health promoting plant cultivated in China, and widely consumed due to its various curative effects. To study the potential bioactive constituents from the rhizome of L. chuanxiong, a chemical investigation was thus performed. In present study, we report the isolation and identification of ten new compounds, including two coumarins (1-2), four lignans (3-6), and four phenols (7-10), along with five known compounds (11-15) from the rhizome of L. chuanxiong. The structures of these compounds were unambiguously established by HR-ESI-MS, UV, IR, CD, NMR spectral data and comparison to reported data. Meanwhile, the anti-inflammation and hepatoprotective activities of all these compounds were evaluated. The results show that compounds 5, 6 and 7 showed excellent inhibition of NO production in LPS-induced RAW 264.7 cells stronger than curcumin, and compounds 5, 7 and 9 exhibited greater hepatoprotective effect than that of bicyclol.
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- 2020
15. Three 11,12-seco-tanshinone derivatives from the rhizomes of Salvia miltiorrhiza
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Pei-Cheng Zhang, Jian-Shuang Jiang, Ya-Nan Yang, Xu Zhang, Quan-Chang Gu, Zi-Ming Feng, and Zhao-Kun Yin
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Pharmacology ,Traditional medicine ,010405 organic chemistry ,Chemistry ,Organic Chemistry ,Pharmaceutical Science ,General Medicine ,Salvianolic acid ,01 natural sciences ,Salvia miltiorrhiza ,0104 chemical sciences ,Analytical Chemistry ,Rhizome ,010404 medicinal & biomolecular chemistry ,Complementary and alternative medicine ,Drug Discovery ,Molecular Medicine - Abstract
Three new compounds named tanshinoic acid A (1), tanshinoic acid B (2), and tanshinoic acid C (3) were isolated from the rhizomes of Salvia miltiorrhiza, together with two known compounds methyl salvianolate A (4) and methyl salvianolate C (5). Their structures were determined on the basis of spectroscopic data (UV, IR, HRESIMS, 1 D and 2 D NMR). The in vitro assay indicated that 4 and 5 could improve the survived rate of cells on oxygen glucose deprivation (OGD) induced neurons damage model and glutamate-induced neurons damage model at a concentration of 10 μM.
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- 2020
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16. New benzoic acid glycosides from Sophora flavescens
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Ya-Nan Yang, Xiang Yuan, Pei-Cheng Zhang, Xu Zhang, Jian-Shuang Jiang, Zi-Ming Feng, and Yi Shen
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Pharmacology ,chemistry.chemical_classification ,Sophora flavescens ,biology ,010405 organic chemistry ,Organic Chemistry ,Pharmaceutical Science ,Glycoside ,General Medicine ,biology.organism_classification ,01 natural sciences ,0104 chemical sciences ,Analytical Chemistry ,010404 medicinal & biomolecular chemistry ,chemistry.chemical_compound ,Complementary and alternative medicine ,chemistry ,Drug Discovery ,Molecular Medicine ,Organic chemistry ,Benzoic acid - Abstract
Two new benzoic acid derivatives, sophophenoside A (1) and sophophenoside B (2), were isolated from Sophora flavescens. Their structures were elucidated by detailed spectroscopic analysis and chemical methods. Compounds 1 and 2 were assayed for their hepatoprotective activity on the cytotoxic effect of D-galactosamine on HL-7702 cells, and compound 1 exhibited a moderate hepatoprotective activity at a concentration of 10 μM.
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- 2020
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17. Two new quinochalcone glycosides from the safflower yellow pigments
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Hao Zhang, Chen-Ping Duan, Jian-Shuang Jiang, Ya-Nan Yang, Xu Zhang, Pei-Cheng Zhang, Luo Xia, and Zi-Ming Feng
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Carthamus tinctorius ,Pharmaceutical Science ,01 natural sciences ,Analytical Chemistry ,Pigment ,Mice ,Chalcone ,Drug Discovery ,Botany ,Animals ,Glycosides ,Pharmacology ,chemistry.chemical_classification ,biology ,Molecular Structure ,010405 organic chemistry ,Organic Chemistry ,Carthamus ,Glycoside ,General Medicine ,Asteraceae ,biology.organism_classification ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,Complementary and alternative medicine ,chemistry ,visual_art ,visual_art.visual_art_medium ,Molecular Medicine ,Safflower yellow - Abstract
Two new quinochalcone glycosides, hydroxysafflor yellow A-4'-O-β-D-glucopyranoside (1) and 3'-hydroxyhydroxysafflor yellow A (2), were isolated from the safflower yellow pigments of Carthamus tinctorius. The structures of new compounds were elucidated by a detailed spectroscopic analysis (UV, IR, HR-ESI-MS, 1D and 2D NMR, ECD). The in vitro assay indicated that compound 1 could improve the survived rate of primary mouse cortical neurons on glutamate-induced neurons damage model at a concentration of 10 μM.
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- 2020
- Full Text
- View/download PDF
18. Sophoflavanones A and B, two novel prenylated flavanones from the roots of Sophora flavescens
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Zi-Ming Feng, Jian-Shuang Jiang, Hui Zhu, Pei-Cheng Zhang, and Ya-Nan Yang
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Circular dichroism ,Antioxidant ,Stereochemistry ,Chemical structure ,medicine.medical_treatment ,Plant composition ,Positive control ,010402 general chemistry ,Plant Roots ,01 natural sciences ,Biochemistry ,Antioxidants ,chemistry.chemical_compound ,Prenylation ,Cell Line, Tumor ,Drug Discovery ,medicine ,Humans ,Molecular Biology ,Sophora flavescens ,biology ,010405 organic chemistry ,Organic Chemistry ,Stereoisomerism ,biology.organism_classification ,0104 chemical sciences ,chemistry ,Pyran ,Flavanones ,Microsomes, Liver ,Sophora - Abstract
In our ongoing investigation of the bioactive compounds from the extract of the roots of Sophora flavescens, two novel prenylated flavanones, named sophoflavanones A (1) and B (2), each with an unusual pyran ring were isolated. Their structures, as well as their absolute configurations, were elucidated based on spectroscopic data including a comparison of their experimental and calculated electronic circular dichroism (ECD) spectra. Additionally, compounds 1 and 2 showed moderate antioxidant activities against Fe2+/cysteine-induced toxicity at a concentration of 0.1 µM (inhibition values of 71.65% and 72.49%, respectively, using vitamin C as a positive control (87.83%)).
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- 2018
19. An Efficient Method for Determining the Relative Configuration of Furofuran Lignans by 1H NMR Spectroscopy
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Si-Yuan Shao, Pei-Cheng Zhang, Zi-Ming Feng, Ya-Nan Yang, and Jian-Shuang Jiang
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Pharmacology ,1h nmr spectroscopy ,010405 organic chemistry ,Chemistry ,Organic Chemistry ,Substituent ,Pharmaceutical Science ,Aromaticity ,01 natural sciences ,0104 chemical sciences ,Analytical Chemistry ,010404 medicinal & biomolecular chemistry ,chemistry.chemical_compound ,Complementary and alternative medicine ,Computational chemistry ,Drug Discovery ,Proton NMR ,Molecular Medicine ,Moiety ,Conformational isomerism - Abstract
An efficient 1H NMR spectroscopic approach for determining the relative configurations of lignans with a 7,9′:7′,9-diepoxy moiety has been established. Using the chemical shift differences of H2-9 and H2-9′ (ΔδH-9 and ΔδH-9′), the configurations of 8-H and 8-OH furofuran lignans can be rapidly and conveniently determined. The rule is applicable for data acquired in DMSO-d6, methanol-d4, or CDCl3. Notably, the rule should be applied carefully when the C-2 or C-6 substituent of the aromatic rings may alter the dominant conformers of the furofuran moiety.
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- 2018
20. Novel phenylpropanoid–amino acid adducts fromLigusticum chuanxiong
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Zi-Ming Feng, Jian-Shuang Jiang, Ya-Nan Yang, Xu Zhang, Bing Han, and Pei-Cheng Zhang
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chemistry.chemical_classification ,Ligusticum chuanxiong ,Phenylpropanoid ,010405 organic chemistry ,Stereochemistry ,Organic Chemistry ,01 natural sciences ,0104 chemical sciences ,Amino acid ,Rhizome ,Adduct ,010404 medicinal & biomolecular chemistry ,Acetic acid ,chemistry.chemical_compound ,Hydrolysis ,chemistry ,Nucleophilic substitution - Abstract
Eight new amino acid derivatives (1–8) and two known compounds (9–10) were isolated from the rhizome of Ligusticum chuanxiong Hort. Their structures were established using UV, IR, HRESIMS, and NMR data. Notably, phenylpropanoid–amino acid adducts 1–6 are the first reported natural products, which possess a unique adduct structure. In addition, their analogues (1–5) were successfully synthesized by nucleophilic substitution and hydrolysis. The absolute configurations of 1–5 were determined by comparison of the specific rotations with those of their analogues and the natural amino acid methyl ester hydrochloride in acetic acid. In addition, these compounds were all evaluated for their neuroprotective effects, and compound 9 showed a moderate protective effect towards human neuroblastoma SH-SY5Y cell injury induced by H2O2.
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- 2018
21. New dimeric phloroglucinol derivatives from Agrimonia pilosa and their hepatoprotective activities
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Jian-Shuang Jiang, Xiang Yuan, Jia Zhang, Ya-Nan Yang, Xu Zhang, Pei-Cheng Zhang, and Zi-Ming Feng
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Dose-Response Relationship, Drug ,Molecular Structure ,biology ,Cell Survival ,Chemistry ,Stereochemistry ,Organic Chemistry ,Phloroglucinol ,Agrimonia ,Hep G2 Cells ,Protective Agents ,biology.organism_classification ,Ring (chemistry) ,Biochemistry ,Agrimonia pilosa ,Structure-Activity Relationship ,chemistry.chemical_compound ,Hepg2 cells ,Drug Discovery ,Humans ,Molecular Biology ,Two-dimensional nuclear magnetic resonance spectroscopy ,Acetaminophen - Abstract
Five new dimeric phloroglucinol derivatives, agrimones A − E (1–5), were isolated from the whole plant of Agrimonia pilosa. Their structures including absolute configurations were determined by a series of spectroscopic data (UV, IR, HR-ESI-MS, 1D and 2D NMR), complemented with the comparison of the experimental and calculated ECD spectra, and gauge-independent atomic orbital (GIAO) NMR calculations. Notably, compounds 1 and 2 represent a highly oxidized 6/6/6 tricyclic ring skeleton based on the cis-fused paraquinone and chroman. Compounds 1a, 4, and 5 exhibited moderate hepatoprotective activities against APAP-induced HepG2 cell injury at 10 μM.
- Published
- 2021
22. Neuroprotective phenylethanoid glycosides with dioxane units from the fruits of Forsythia suspensa
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Pei-Cheng Zhang, Fan Zhang, Zi-Ming Feng, Jian-Shuang Jiang, Ya-Nan Yang, and Si-Yuan Shao
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chemistry.chemical_classification ,Forsythia suspensa ,biology ,010405 organic chemistry ,Stereochemistry ,Organic Chemistry ,Glycoside ,Rotenone ,Phenylethanoid ,biology.organism_classification ,01 natural sciences ,Biochemistry ,Nmr data ,Neuroprotection ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,chemistry.chemical_compound ,chemistry ,Drug Discovery ,Organic chemistry ,Serum deprivation - Abstract
Six new phenylethanoid glycosides possessing dioxane moieties, named forsyoxasides A−F ( 1–6 ), together with four known such compounds ( 7–10 ) were isolated from the fruits of Forsythia suspensa . These structures were illustrated by extensive NMR spectroscopic techniques and by comparing their NMR data with the related literatures. Notably, forsyoxaside A ( 1 ) is a novel dioxane phenylethanoid glycoside with an axial aromatic ring, which is rare in the natural sources. Compounds 1 , 4 , 7 and 8 showed remarkable bioactivities against rotenone induced PC12 cell damage. Furthermore, 1 and 7 displayed strong activities against serum deprivation induced damage on the same cells.
- Published
- 2017
23. New heterocyclic compounds from Ranunculus ternatus Thunb
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Jian-Shuang Jiang, Pei-Cheng Zhang, Zi-Ming Feng, Ya-Nan Yang, and Zhi-lai Zhan
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Ranunculus ,chemistry.chemical_classification ,Circular dichroism ,Molecular Structure ,010405 organic chemistry ,Stereochemistry ,Circular Dichroism ,Organic Chemistry ,010402 general chemistry ,Furfural ,Ranunculus ternatus ,Plant Roots ,01 natural sciences ,Biochemistry ,Nmr data ,0104 chemical sciences ,chemistry.chemical_compound ,chemistry ,Heterocyclic Compounds ,Heterocyclic compound ,Drug Discovery ,Quantum Theory ,Organic chemistry ,Molecular Biology - Abstract
Five new heterocyclic compounds, 5-α-d-fructofuranosylmethyl-furfural (1), 5-β-d-fructofuranosylmethyl-furfural (2), 5-β-d-fructopyranosylmethyl-furfural (3), 4-(2-((2S-2,3-dihydroxypropoxy)methyl)-5-formyl-1H-pyrrol-1-yl)butanoic acid (4), and 3S,4S-4,5,8-trihydroxy-3-(prop-1-en-2-yl)isochroman-1-one (5), were obtained from the root of Ranunculus ternatus Thunb., which is a traditional Chinese anti-tuberculosis medicine. Their structures were elucidated by UV, IR, HRESIMS, NMR data, and the comparison of experimental and calculated electronic circular dichroism (ECD) spectra. Notably, compounds 1-3 are rarely occurring furfural fructosides in natural sources. These heterocyclic compounds could be further studied for the synthetic chemists and pharmacologists due to the source and structural properties.
- Published
- 2017
24. Four new iridoid glucosides containing the furan ring from the fruit of Cornus officinalis
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Xiao-Xue Wang, Ya-Nan Yang, Jun He, Jie-Kun Xu, Bing-Zhi Ma, Pei-Cheng Zhang, Xian-Sheng Ye, and Wei-Ku Zhang
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0301 basic medicine ,Circular dichroism ,Iridoid ,medicine.drug_class ,Stereochemistry ,Iridoid Glucosides ,PC12 Cells ,01 natural sciences ,03 medical and health sciences ,chemistry.chemical_compound ,Cornus ,Glucoside ,Furan ,Drug Discovery ,medicine ,Animals ,Organic chemistry ,Pharmacology ,Molecular Structure ,biology ,Chemistry ,Acetal ,General Medicine ,Cornus officinalis ,biology.organism_classification ,Rats ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,Neuroprotective Agents ,030104 developmental biology ,Fruit ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
Four new and rare iridoid glucosides, cornusfuroside A-D (1-4), containing the furan ring were identified from water extract of the fruit of Cornus officinalis. These new chemical structures were determined through extensive spectroscopic analysis, including 1D and 2D NMR, IR, HRESIMS, experimental and calculated electronic circular dichroism (ECD). Notably, this study is the first report on the isolation of four iridoid glucoside structures with acetal functions in the sugar moiety. The neuroprotective effects of these compounds were also evaluated in vitro.
- Published
- 2017
25. Neuroprotective Caffeoylquinic Acid Derivatives from the Flowers of Chrysanthemum morifolium
- Author
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Ya-Nan Yang, Zi-Ming Feng, Peng-Fei Yang, Jian-Shuang Jiang, and Pei-Cheng Zhang
- Subjects
Chrysanthemum ,Stereochemistry ,Pharmaceutical Science ,Flowers ,01 natural sciences ,Analytical Chemistry ,Drug Discovery ,Nuclear Magnetic Resonance, Biomolecular ,Chromatography, High Pressure Liquid ,Flavonoids ,Pharmacology ,Molecular Structure ,biology ,010405 organic chemistry ,Chemistry ,Chrysanthemum morifolium ,Organic Chemistry ,Hydrogen Peroxide ,Circular dichroism spectra ,biology.organism_classification ,Cycloaddition ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,Caffeoylquinic acid ,Glucose ,Neuroprotective Agents ,Complementary and alternative medicine ,Molecular Medicine ,Chlorogenic Acid ,Drugs, Chinese Herbal - Abstract
Three new caffeoylquinic acid derivatives, chrysanthemorimic acids A-C (1-3), and 11 known compounds (4-14) were isolated and characterized from the flowers of Chrysanthemum morifolium. Their structures were confirmed by spectroscopic data as well as by comparison of the experimental and calculated electronic circular dichroism spectra. Chrysanthemorimic acids A-C possess a rare 8-oxa-bicyclo[3.2.1]oct-3-en-2-one ring that is formed through a [5+2] cycloaddition of caffeoylquinic acid with a d-glucose derivative. Compounds 1-3, 6-8, 12, and 13 displayed significant effects against hydrogen peroxide-induced neurotoxicity in SH-SY5Y cells at 10 μM.
- Published
- 2017
26. Sesquiterpenoid and C 14 -polyacetylene glycosides from the rhizomes of Atractylodes lancea
- Author
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Kuo Xu, Pei-Cheng Zhang, Zi-Ming Feng, Jian-Shuang Jiang, and Ya-Nan Yang
- Subjects
chemistry.chemical_classification ,Circular dichroism ,biology ,010405 organic chemistry ,Stereochemistry ,Glycoside ,General Chemistry ,010402 general chemistry ,biology.organism_classification ,01 natural sciences ,0104 chemical sciences ,Rhizome ,Polyacetylene ,chemistry.chemical_compound ,chemistry ,Chiral derivatization ,Monosaccharide ,Organic chemistry ,Atractylodes lancea ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
Four new glycosides including a eudesmane-type sesquiterpenoid (1), a guaiane-type sesquiterpenoid (2), and two C14-polyacetylenes (3, 4) were isolated from the rhizomes of Atractylodes lancea. Their structures were elucidated by means of spectroscopic and spectrometric analyses (UV, IR, 1D and 2D NMR, and HR-ESIMS). The absolute configurations of their aglycones were established based on the experimental and calculated electronic circular dichroism (ECD), whereas those of monosaccharide moieties were determined by the GC method after chiral derivatization. Compound 4 showed weak anti-inflammatory effects on the LPS-induced NO production in microglia BV2 cells at a concentration of 10 μmol L−1.
- Published
- 2017
27. Direct Assignment of the Threo and Erythro Configurations in Polyacetylene Glycosides by 1H NMR Spectroscopy
- Author
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Ya-Nan Yang, Kuo Xu, Zi-Ming Feng, Pei-Cheng Zhang, Peng-Fei Yang, and Jian-Shuang Jiang
- Subjects
chemistry.chemical_classification ,010405 organic chemistry ,Stereochemistry ,Organic Chemistry ,Diol ,Diastereomer ,Glycoside ,010402 general chemistry ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,Solvent ,chemistry.chemical_compound ,Hydrolysis ,Polyacetylene ,chemistry ,Physical and Theoretical Chemistry ,Derivatization ,Vicinal - Abstract
An approach for discriminating the threo and erythro configurations of polyacetylene glycosides by 1H NMR spectroscopy was developed. Using acetic acid-d4/D2O as the solvent, a relatively larger 3JHH value (7.0 Hz) for the acyclic vicinal diol group was unambiguously assigned to the threo configuration, whereas the smaller value (3.5 Hz) was assigned to the erythro configuration. This convenient method requires no hydrolysis or derivatization and is suitable for micromolar concentrations of polyacetylene glycosides. The underlying mechanism is discussed via visualized conformations.
- Published
- 2017
28. Forsythenethosides A and B: two new phenylethanoid glycosides with a 15-membered ring from Forsythia suspensa
- Author
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Pei-Cheng Zhang, Jian-Shuang Jiang, Ya-Nan Yang, Zi-Ming Feng, and Si-Yuan Shao
- Subjects
Models, Molecular ,Stereochemistry ,Molecular Conformation ,Ring (chemistry) ,PC12 Cells ,01 natural sciences ,Biochemistry ,Molecular conformation ,chemistry.chemical_compound ,Forsythia ,Animals ,Glycosides ,Physical and Theoretical Chemistry ,chemistry.chemical_classification ,Forsythia suspensa ,biology ,010405 organic chemistry ,Organic Chemistry ,Glycoside ,Phenylethanoid ,Nuclear magnetic resonance spectroscopy ,Phenylethyl Alcohol ,biology.organism_classification ,Rats ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,Neuroprotective Agents ,chemistry ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
Forsythenethosides A (1) and B (2), two new phenylethanoid glycosides with an unprecedented 15-membered carbon scaffold ring, were isolated from the fruits of Forsythia suspensa. Their structures, including their geometric configurations, were determined via extensive NMR spectroscopy techniques, especially using 2D NMR data combined with systematic conformational analysis. Forsythenethosides A and B showed strong neuroprotective activities against serum-deprivation-induced PC12 cell damage. Furthermore, they were active on rotenone-induced PC12 cell damage.
- Published
- 2017
29. Four new C10-polyacetylene glycosides from the rhizomes of Atractylodes lancea
- Author
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Pei-Cheng Zhang, Zi-Ming Feng, Kuo Xu, Jian-Shuang Jiang, and Ya-Nan Yang
- Subjects
Stereochemistry ,Pharmaceutical Science ,01 natural sciences ,Analytical Chemistry ,Polyacetylene ,chemistry.chemical_compound ,Drug Discovery ,Organic chemistry ,Pharmacology ,chemistry.chemical_classification ,biology ,010405 organic chemistry ,Organic Chemistry ,Glycoside ,General Medicine ,biology.organism_classification ,0104 chemical sciences ,Rhizome ,010404 medicinal & biomolecular chemistry ,Complementary and alternative medicine ,chemistry ,Phytochemical ,Hepg2 cells ,Atractylodes ,Molecular Medicine ,Atractylodes lancea ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
An ongoing phytochemical investigation of the rhizomes of Atractylodes lancea resulted in the isolation of four new C10-type polyacetylene glycosides (1-4). Their structures were elucidated on the basis of extensive spectroscopic data (UV, IR, 1D and 2D NMR, and HRESIMS). The absolute configurations of compounds 2-4 were determined by comparing the specific rotations of their aglycones. Notably, compounds 2 and 3 exhibited significant hepatoprotective activities against APAP-induced HepG2 cell injury at a concentration of 10 μM. Compounds 2 and 3 showed weak anti-inflammatory effects on LPS-induced NO production in microglia BV2 cells at a concentration of 10 μM.
- Published
- 2016
30. Seven new flavonoid glycosides from the roots of Glycyrrhiza uralensis and their biological activities
- Author
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Ya-Nan Yang, Yuan-Yuan Liu, Jian-Shuang Jiang, Zi-Ming Feng, and Pei-Cheng Zhang
- Subjects
Antioxidant ,medicine.medical_treatment ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Plant Roots ,Antioxidants ,Analytical Chemistry ,medicine ,Glycyrrhiza uralensis ,Glycosides ,Sugar ,Flavonoids ,Traditional medicine ,biology ,Flavonoid glycosides ,Dose-Response Relationship, Drug ,010405 organic chemistry ,Chemistry ,Organic Chemistry ,General Medicine ,biology.organism_classification ,0104 chemical sciences ,Liver ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
As part of our ongoing investigation of the bioactive constituents from the roots of Glycyrrhiza uralensis Fisch., seven new flavonoid glycosides (1–7) were obtained along with 19 known compounds (8–26). All of the isolates possessed one or more sugar moieties. Their structures, as well as the absolute configurations, were elucidated on the basis of spectroscopic data (UV, IR, HRESIMS, 1D and 2D NMR, and CD). In the in vitro assay, compounds 3 and 7 showed moderate antioxidant activities at a concentration of 0.1 μM; compound 2 showed hepatoprotective activity at a concentration of 10 μM.
- Published
- 2019
31. Base-catalyzed oxidative dearomatization of multisubstituted phloroglucinols: An easy access to C-glucosyl 3,5,6-trihydroxycyclohexa-2,4-dienone derivatives
- Author
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Zhong Chen, Pei-Cheng Zhang, Zi-Ming Feng, Xiang Yuan, Ya-Nan Yang, Xu Zhang, Jian-Shuang Jiang, and Wan Gao
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chemistry.chemical_classification ,Base (chemistry) ,Organic Chemistry ,Stereoisomerism ,General Medicine ,Oxidative phosphorylation ,Phloroglucinol ,Biochemistry ,Combinatorial chemistry ,Catalysis ,Analytical Chemistry ,chemistry ,Carbohydrate Sequence ,Glucosides ,Carbohydrate Conformation ,Oxidation-Reduction - Abstract
An efficient and simple method for the protecting group-free synthesis of C-glucosyl 3,5,6-trihydroxycyclohexa-2,4-dienone has been firstly established. This method is compatible with various functional groups, such as benzyl and phenethyl groups, affording a range of C-glucosyl 3,5,6-trihydroxycyclohexa-2,4-dienone derivatives.
- Published
- 2019
32. New Caffeoylquinic Acid Derivatives and Flavanone Glycoside from the Flowers of Chrysanthemum morifolium and Their Bioactivities
- Author
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Pei-Cheng Zhang, Yu-Feng Fu, Peng-Fei Yang, Zhi-Fei Chen, Ya-Nan Yang, Qi-Shan Yuan, Duobin Mao, Sheng-Chen Zhao, and Chun-Yu He
- Subjects
0106 biological sciences ,Pharmaceutical Science ,Chrysanthemum morifolium ,01 natural sciences ,neuroprotective activity ,Analytical Chemistry ,lcsh:QD241-441 ,03 medical and health sciences ,chemistry.chemical_compound ,lcsh:Organic chemistry ,Drug Discovery ,Physical and Theoretical Chemistry ,030304 developmental biology ,chemistry.chemical_classification ,0303 health sciences ,caffeoylquinic acid ,Traditional medicine ,biology ,Organic Chemistry ,Glycoside ,biology.organism_classification ,flavanone glycoside ,010601 ecology ,Caffeoylquinic acid ,chemistry ,Chemistry (miscellaneous) ,Molecular Medicine ,Flavanone - Abstract
The Chrysanthemum morifolium flower is widely used in China and Japan as a food, beverage, and medicine for many diseases. In our work, two new caffeoylquinic acid derivatives (1, 2), a new flavanone glycoside (3), and six reported flavanones (4&ndash, 9) were isolated and identified from the flowers of C. morifolium. The chemical structures of all isolates were elucidated by the analysis of comprehensive spectroscopic data as well as by comparison with previously reported data. The isolated constituents 1&ndash, 8 were evaluated for their neuroprotective activity, and compounds 3 and 4 displayed neuroprotective effects against hydrogen peroxide-induced neurotoxicity in human neuroblastoma SH-SY5Y cells.
- Published
- 2019
33. Antioxidant epoxydon and benzolactone derivatives from the insect-associated fungus Phoma sp
- Author
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Xiao-Ying Xie, Chunping Xu, Dan-Dan Meng, Gai-Gai Xu, Li Tianxiao, Bing Bai, Ya-Nan Yang, Ying Wang, and Ya-Xin Guo
- Subjects
Insecta ,Antioxidant ,Stereochemistry ,media_common.quotation_subject ,medicine.medical_treatment ,Pharmaceutical Science ,Insect ,Fungus ,01 natural sciences ,Antioxidants ,Analytical Chemistry ,Ascomycota ,Drug Discovery ,medicine ,Animals ,Humans ,media_common ,Pharmacology ,Molecular Structure ,biology ,010405 organic chemistry ,Chemistry ,Circular Dichroism ,fungi ,Organic Chemistry ,General Medicine ,biology.organism_classification ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,Complementary and alternative medicine ,Phoma ,Epoxy Compounds ,Molecular Medicine - Abstract
One new epoxydon ester (1) and a new benzolactone derivative (2), along with four known compounds (3−6), were isolated from the insect-associated fungus Phoma sp. Their structures were confirmed by extensive MS and NMR spectroscopic analysis and their absolute configurations were determined by a combination of modified Mosher method and Mo2(OCOCH3)4-induced electronic circular dichroism (ECD) experiments. Compounds 1 and 5 were revealed to have potent antioxidant activities, which were approximate to the potency of the positive control trolox. In addition, 1 also exhibited moderate cytotoxic effect against human MGC-803 tumor cell line.
- Published
- 2019
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34. New phenolic glycosides from Polygonum cuspidatum
- Author
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Fu-Shuang Li, Zi-Ming Feng, Jian-Shuang Jiang, Pei-Cheng Zhang, and Ya-Nan Yang
- Subjects
Pharmacology ,chemistry.chemical_classification ,Stereochemistry ,Organic Chemistry ,Pharmaceutical Science ,Glycoside ,General Medicine ,Analytical Chemistry ,Isocoumarin ,chemistry.chemical_compound ,Complementary and alternative medicine ,chemistry ,Drug Discovery ,Molecular Medicine ,Cytotoxicity ,POLYGONUM CUSPIDATUM - Abstract
Two new isobenzofuranone derivatives, polyphthaliside A (1) and polyphthaliside B (2), and a new isocoumarin derivative, polyisocoumarin (3), were isolated from Polygonum cuspidatum. Their structures were elucidated by detailed spectroscopic analysis and chemical methods. The cytotoxicity activity and PTP1B inhibitory activity of compounds 1–3 were estimated and none of them exhibited activities at a concentration of 10 μM.
- Published
- 2019
- Full Text
- View/download PDF
35. Eight new biflavonoids with lavandulyl units from the roots of Sophora flavescens and their inhibitory effect on PTP1B
- Author
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Xiang Yuan, Hui Zhu, Zi-Ming Feng, Hai-Wei Yan, Jian-Shuang Jiang, Pei-Cheng Zhang, and Ya-Nan Yang
- Subjects
genetic structures ,Stereochemistry ,Acyclic Monoterpenes ,01 natural sciences ,Biochemistry ,Plant Roots ,chemistry.chemical_compound ,Structure-Activity Relationship ,Chalcones ,Drug Discovery ,Bioassay ,Biflavonoids ,Humans ,Enzyme Inhibitors ,Molecular Biology ,Inhibitory effect ,Protein Tyrosine Phosphatase, Non-Receptor Type 1 ,Sophora flavescens ,biology ,Dose-Response Relationship, Drug ,Molecular Structure ,010405 organic chemistry ,Plant Extracts ,Organic Chemistry ,Dihydrochalcone ,biology.organism_classification ,Recombinant Proteins ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,chemistry ,Flavanone ,Sophora - Abstract
In the course of studying the components from the roots of Sophora flavescens, eight new unusual biflavonoids consisting of a flavanone fused with a dihydrochalcone skeleton were isolated. These new chemical structures were elucidated by means of UV, IR, HRESIMS, NMR and ECD spectroscopic data and a comparison of experimental ECD spectra with calculated ECD spectra. Some compounds were subjected to an antidiabetic bioassay on human recombinant PTP1B inhibition, and showed strong inhibitory activity.
- Published
- 2018
36. An Approach for Determining the Absolute Configuration of C-2 in 2-Oxygenated Phenylethanoid Glycosides by 1H NMR Spectroscopy
- Author
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Fan Zhang, Jian-Shuang Jiang, Ya-Nan Yang, Pei-Cheng Zhang, Zi-Ming Feng, and Si-Yuan Shao
- Subjects
chemistry.chemical_classification ,1h nmr spectroscopy ,010405 organic chemistry ,Organic Chemistry ,Absolute configuration ,Analytical chemistry ,Glycoside ,Phenylethanoid ,010402 general chemistry ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,Crystallography ,chemistry.chemical_compound ,chemistry ,Physical and Theoretical Chemistry ,Methylene - Abstract
The absolute configurations of 2-oxygenated phenylethanoid glycosides were conveniently determined by (1)H NMR spectroscopy. A comparison of the chemical shift differences (Δδ) of the diastereotopic methylene protons (H-1) demonstrate that a large chemical shift difference corresponds to an R configuration and a small chemical shift difference indicates S for the 2-alkoxy form. However, the situation is contrary to that of the 2-hydroxy form. Furthermore, the mechanism underlying this result is discussed based on the visualized conformations of such compounds.
- Published
- 2016
37. Bioactive Octahydroxylated C21 Steroids from the Root Bark of Lycium chinense
- Author
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Ya-Nan Yang, Pei-Cheng Zhang, Zhi-lai Zhan, Jian-Shuang Jiang, Fei Ye, Jing Xie, Zi-Ming Feng, and Ya-Wen An
- Subjects
0301 basic medicine ,Stereochemistry ,Pharmaceutical Science ,Plant Roots ,01 natural sciences ,Analytical Chemistry ,03 medical and health sciences ,Lycium chinense ,Islet cells ,Drug Discovery ,Autophagy ,Humans ,Viability assay ,Sugar ,C21 steroid ,Pharmacology ,Molecular Structure ,biology ,Plant Extracts ,010405 organic chemistry ,Organic Chemistry ,Data interpretation ,Lycium ,Pregnanes ,biology.organism_classification ,0104 chemical sciences ,030104 developmental biology ,Complementary and alternative medicine ,Biochemistry ,visual_art ,Plant Bark ,visual_art.visual_art_medium ,Molecular Medicine ,Bark - Abstract
Lyciumsterols A-K (1-11), 11 new octahydroxylated C21 steroids, were isolated from the root bark of Lycium chinense, along with 15 known compounds. Characterization of these C21 steroids showed the presence of eight hydroxy groups on the C21 steroid skeleton with a (2E,4E)-5-phenyl-2,4-pentadienoate group at C-12 or C-20 and various 2,6-deoxy sugar residues at C-3. The structures of these compounds were elucidated using spectroscopic data interpretation. Compounds 2, 3, and 7 exhibited dose-dependent protective effects on pancreatic islet cells and may help to improve cell viability. In addition, it was found that compounds 7, 8, 9, and 11 exhibited autophagy activation.
- Published
- 2016
38. Seven New Acyl Glycosides fromErycibe obtusifolia
- Author
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Kuo Xu, Ya-Nan Yang, Pei-Cheng Zhang, Zi-Ming Feng, Zhao-zhen Liu, and Jian-Shuang Jiang
- Subjects
chemistry.chemical_classification ,Erycibe obtusifolia ,Traditional medicine ,010405 organic chemistry ,Chemistry ,Organic Chemistry ,Glycoside ,01 natural sciences ,Biochemistry ,Catalysis ,0104 chemical sciences ,Inorganic Chemistry ,010404 medicinal & biomolecular chemistry ,Drug Discovery ,Physical and Theoretical Chemistry - Published
- 2016
39. Stereoselective synthesis of (Z)-3-ylidenephthalides via AlCl3-mediated cyclization with 2-acylbenzoic acids
- Author
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Zi-Ming Feng, Pei-Cheng Zhang, Gangsheng Li, Xujie Wang, Ya-Nan Yang, Xu Zhang, and Jian-Shuang Jiang
- Subjects
Natural product ,010405 organic chemistry ,Organic Chemistry ,010402 general chemistry ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,Catalysis ,chemistry.chemical_compound ,chemistry ,Yield (chemistry) ,Drug Discovery ,Organic chemistry ,Stereoselectivity ,Selectivity - Abstract
An efficient method for the synthesis of (Z)-3-ylidenephthalides is reported in moderate to high yield with AlCl3 as catalyst. Different substrates of the 2-acylbenzoic acids are well performed in the Z/E selectivity. This method is highlighted by the gram-scale synthesis of the natural product (Z)-3-butylidene-5-hydroxyphthalide with anti-inflammatory activity.
- Published
- 2020
40. New triacetic acid lactone glycosides from the fruits of Forsythia suspensa and their nitric oxide production inhibitory activity
- Author
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Pei-Cheng Zhang, Zi-Ming Feng, Si-Yuan Shao, Ya-Nan Yang, and Jian-Shuang Jiang
- Subjects
Lipopolysaccharides ,Lipopolysaccharide ,Stereochemistry ,Nitric Oxide ,010402 general chemistry ,Inhibitory postsynaptic potential ,01 natural sciences ,Biochemistry ,Cell Line ,Analytical Chemistry ,Nitric oxide ,Mice ,chemistry.chemical_compound ,Animals ,Monosaccharide ,Glycosides ,Forsythia ,chemistry.chemical_classification ,Triacetic acid lactone ,Forsythia suspensa ,Molecular Structure ,biology ,Plant Extracts ,010405 organic chemistry ,Organic Chemistry ,Glycoside ,General Medicine ,biology.organism_classification ,0104 chemical sciences ,Carbohydrate Sequence ,chemistry ,Pyrones ,Microglia - Abstract
Three new triacetic acid lactone (TAL) glycosides, forsyphensides A-C (1-3) were isolated from the fruits of Forsythia suspensa. Their structures were elucidated by comprehensive spectroscopic techniques. The absolute configurations of their monosaccharides were determined by GC analysis. Notably, forsyphensides A-C were relatively rare TAL glycosides identified from plants. Compound 1 exhibited inhibitory activity against the lipopolysaccharide (LPS)-induced nitric oxide (NO) production in microglia BV2 cells with the inhibition rate of 69.40%.
- Published
- 2020
41. Bioactive butylphthalide derivatives from Ligusticum chuanxiong
- Author
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Ya-Nan Yang, Xu Zhang, Jian-Shuang Jiang, Zi-Ming Feng, and Pei-Cheng Zhang
- Subjects
Circular dichroism ,Ligusticum chuanxiong ,Magnetic Resonance Spectroscopy ,Stereochemistry ,Cell Survival ,Molecular Conformation ,Protective Agents ,Biochemistry ,Plant Roots ,chemistry.chemical_compound ,Cell Line, Tumor ,Drug Discovery ,Humans ,Ligusticum ,Molecular Biology ,Benzofurans ,Ethanol ,Circular Dichroism ,Organic Chemistry ,Diastereomer ,Stereoisomerism ,Butylphthalide ,chemistry ,Hepg2 cells ,Enantiomer ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
Seven new butylphthalide derivatives, ligusticumolide A-G (1–7), together with two known butylphthalide derivatives (8–9) were isolated from an ethanol extract of Ligusticum chuanxiong Hort. The structures of these derivatives were elucidated from analysis of 1D/2D NMR, UV, IR and HRESIMS data. The absolute configurations of these derivatives were determined by electronic circular dichroism (ECD) calculations and Mosher′s method. Ligusticumolide A (1) and ligusticumolide B (2) are enantiomers that were obtained by chiral separation. Ligusticumolide C (3) and ligusticumolide D (4) are diastereomers. All of the compounds were evaluated for their hepatoprotective activity against N-acetyl-p-aminophenol-induced HepG2 cell injury. Compounds 4, 5, and 7–9 showed more significant hepatoprotective activity than that of the positive control drug (bicyclol) at a concentration of 10 μM (p
- Published
- 2018
42. Six new compounds from the flowers of Chrysanthemum morifolium and their biological activities
- Author
-
Zi-Ming Feng, Pei-Cheng Zhang, Peng-Fei Yang, Jian-Shuang Jiang, and Ya-Nan Yang
- Subjects
Chrysanthemum ,Catechols ,Flowers ,01 natural sciences ,Biochemistry ,Lignans ,Mice ,Glucosides ,Cell Line, Tumor ,Drug Discovery ,Animals ,Humans ,Molecular Biology ,Folk medicine ,chemistry.chemical_classification ,Traditional medicine ,biology ,010405 organic chemistry ,Chemistry ,Chrysanthemum morifolium ,Organic Chemistry ,Glycoside ,Hydrogen Peroxide ,biology.organism_classification ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,Oxidative Stress ,Neuroprotective Agents ,RAW 264.7 Cells - Abstract
Flower of Chrysanthemum morifolium is widely used in China and Japan as a folk medicine in treatment of many diseases. However, its active compounds remain largely unknown. In the present work, we have isolated, purified and characterized six new compounds (1-6), including two new arylnaphthalene lignans and four new phenolic glycosides, together with eight known compounds (7-14), from the flower of C. morifolium. Their structures and absolute configurations were elucidated in detail using 1D and 2D NMR, UV, IR, ORD, HRESIMS and ECD spectrometric data. In addition, compounds 1-3 possessed the significant neuroprotective activity against hydrogen peroxide-induced neurotoxicity in human neuroblastoma SH-SY5Y cells.
- Published
- 2018
43. Anti-inflammatory phenylpropanoid glycosides from the fruits of Forsythia suspensa
- Author
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Zi-Ming Feng, Ya-Nan Yang, Si-Yuan Shao, Jian-Shuang Jiang, and Pei-Cheng Zhang
- Subjects
Lipopolysaccharides ,Anomer ,Lipopolysaccharide ,Phenylpropanoid glycosides ,Propanols ,medicine.drug_class ,Clinical Biochemistry ,Anti-Inflammatory Agents ,Pharmaceutical Science ,Biochemistry ,Anti-inflammatory ,chemistry.chemical_compound ,Phenols ,Drug Discovery ,medicine ,Humans ,Glycosides ,Sugar ,Forsythia ,Molecular Biology ,IC50 ,Forsythia suspensa ,biology ,Plant Extracts ,Tumor Necrosis Factor-alpha ,Macrophages ,Organic Chemistry ,biology.organism_classification ,chemistry ,Fruit ,Molecular Medicine ,Tumor necrosis factor alpha - Abstract
Five new phenylpropanoid glycosides, susaroysides A–E (1–5) were isolated from the fruits of Forsythia suspensa. Their structures were elucidated by comprehensive spectroscopic data analysis. The absolute configurations of their sugars were determined by GC analysis. Notably, susaroysides A–D possessed a sugar with an unsubstituted anomeric carbon, which is relatively rare in natural sources. Compound 1 exhibited significant anti-inflammatory activity against the lipopolysaccharide (LPS)-induced tumor necrosis factor (TNF)-α expression in macrophage cells with the IC50 value of 1.053 μM.
- Published
- 2019
44. Two new thiophene polyacetylene glycosides from Atractylodes lancea
- Author
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Jian-Shuang Jiang, Jinghua Zhang, Ya-Nan Yang, Pei-Cheng Zhang, Wei Wang, Ning Du, Zi-Ming Feng, and Kuo Xu
- Subjects
Circular dichroism ,Anti-Inflammatory Agents ,Pharmaceutical Science ,Thiophenes ,01 natural sciences ,Analytical Chemistry ,chemistry.chemical_compound ,Polyacetylene ,Drug Discovery ,Thiophene ,Organic chemistry ,Glycosides ,Pharmacology ,chemistry.chemical_classification ,biology ,Molecular Structure ,010405 organic chemistry ,Organic Chemistry ,Absolute configuration ,Glycoside ,Polyynes ,General Medicine ,Atractylodes ,biology.organism_classification ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,Complementary and alternative medicine ,chemistry ,Phytochemical ,Molecular Medicine ,Atractylodes lancea ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
Phytochemical investigation on the rhizomes of Atractylodes lancea led to the isolation of two new thiophene polyacetylene glycosides (1 and 2) and six known compounds (3-8). Their structures were elucidated based on the extensive spectroscopic data (UV, IR, 1D and 2D NMR, and HRESIMS). The absolute configurations of new compounds were established by calculated and experimental circular dichroism. All the compounds were assessed on the lipopolysaccharide-induced NO production in BV2 cells and compounds 3, 7, and 8 showed moderate inhibitory activities.
- Published
- 2018
45. Forsythoneosides A–D, Neuroprotective Phenethanoid and Flavone Glycoside Heterodimers from the Fruits of Forsythia suspensa
- Author
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Xiu-Yun Song, Li Li, Pei-Cheng Zhang, Jian-Shuang Jiang, Fan Zhang, Ya-Nan Yang, Zi-Ming Feng, Si-Yuan Shao, and Nai-Hong Chen
- Subjects
Circular dichroism ,Stereochemistry ,Flavonoid ,Pharmaceutical Science ,PC12 Cells ,Flavones ,Lignans ,Analytical Chemistry ,Cardiac Glycosides ,chemistry.chemical_compound ,Forsythia ,Drug Discovery ,Animals ,Glycosides ,Pharmacology ,chemistry.chemical_classification ,Forsythia suspensa ,Molecular Structure ,biology ,Circular Dichroism ,Organic Chemistry ,Glycoside ,Phenylethanoid ,biology.organism_classification ,Rats ,Neuroprotective Agents ,Complementary and alternative medicine ,chemistry ,Pyran ,Fruit ,Molecular Medicine ,Drugs, Chinese Herbal - Abstract
Forsythoneosides A-D (1-4), four unusual adducts of a flavonoid unit fused to a phenylethanoid glycoside through a pyran ring or carbon-carbon bond, and four new phenylethanoid glycosides (5-8) were isolated from the fruits of Forsythia suspensa, together with nine known compounds. The structures of 1-8, including their absolute configurations, were elucidated by spectroscopic data as well as experimental and calculated electronic circular dichroism analysis. Compounds 2 and 4 inhibited PC12 cell damage induced by rotenone, and increased cell viability from 53.9 ± 7.1% to 70.1 ± 4.0% and 67.9 ± 5.2% at 0.1 μM, respectively.
- Published
- 2015
46. NMR Spectroscopic Method for the Assignment of 3,5-Dioxygenated Aromatic Rings in Natural Products
- Author
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Zhong Chen, Ya-Wen An, Hui Zhu, Pei-Cheng Zhang, Zi-Ming Feng, Jian-Shuang Jiang, Fu Liu, and Ya-Nan Yang
- Subjects
Models, Molecular ,Proton ,Carbon-13 NMR satellite ,Stereochemistry ,Pharmaceutical Science ,Lignans ,Spectral line ,Analytical Chemistry ,Computational chemistry ,Drug Discovery ,Molecule ,Polycyclic Aromatic Hydrocarbons ,Nuclear Magnetic Resonance, Biomolecular ,Flavonoids ,Pharmacology ,Biological Products ,Molecular Structure ,Chemistry ,Organic Chemistry ,Temperature ,Aromaticity ,Carbon-13 NMR ,Complementary and alternative medicine ,Deuterium ,Solvents ,Proton NMR ,Molecular Medicine ,Protons - Abstract
In recent years, certain "new" naturally occurring compounds (1-28) with 3,5-dioxygenated aromatic rings have been reported. A comparison of the NMR data of these compounds with the data of four model compounds (A-D) indicated that the structures of these "new" compounds were erroneous. The reason for the incorrect elucidation of the structures of 1-28 was attributed to "deceptively simple" (1)H NMR spectra, which displayed two broad singlets with integrations of 1:2 for H-2 and H-5, H-6, respectively. To expose the misleading results from the spectra, serial (1)H NMR experiments on compounds A-D were performed using various deuterated solvents and temperatures. The results revealed separated proton signals for the ABX system in certain deuterated solvents. Additionally, the characteristic differences between 3,4- and 3,5-dioxygenated aromatic rings in their (13)C NMR spectra are summarized based on our experiment and data reported. This approach is useful for analyzing the patterns of dioxygenated aromatic rings in natural products, especially when "deceptively simple" (1)H NMR spectra are displayed.
- Published
- 2015
47. Neuroprotective naphthalene and flavan derivatives from Polygonum cuspidatum
- Author
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Jian-Shuang Jiang, Fu Liu, Li Li, Pei-Cheng Zhang, Fu-Shuang Li, Ya-Nan Yang, and Zi-Ming Feng
- Subjects
Stereochemistry ,Plant Science ,Naphthalenes ,Horticulture ,PC12 Cells ,Biochemistry ,Neuroprotection ,Polygonaceae ,chemistry.chemical_compound ,Flavan ,Fallopia japonica ,Rotenone ,Animals ,Humans ,Organic chemistry ,Nuclear Magnetic Resonance, Biomolecular ,Molecular Biology ,Naphthalene ,Piceid ,Flavonoids ,chemistry.chemical_classification ,Molecular Structure ,biology ,Glycoside ,General Medicine ,biology.organism_classification ,In vitro ,Rats ,Neuroprotective Agents ,chemistry ,Algorithms - Abstract
Ten naphthalene derivatives including two unusual glycosides possessing a naphthalene-fused piceid via a [C8'-O-C6-C5-C7']-trans-dihydrofuran ring, two flavan derivatives, as well as sixteen known phenolic compounds, were isolated from Polygonum cuspidatum. The structures were determined by extensive NMR, MS, CD data, and chemical evidence. In the in vitro neuroprotective assays, at the concentration of 10 μM, five of these compounds exhibited significant effects against PC12 cells injured by rotenone.
- Published
- 2015
48. Sophopterocarpan A, a novel pterocarpine derivative with a benzotetrahydrofuran-fused bicyclo [3.3.1] nonane from Sophora flavescens
- Author
-
Ya-Nan Yang, Kuo Xu, Jing Xie, Jian-Shuang Jiang, Hui Zhu, Zi-Ming Feng, and Pei-Cheng Zhang
- Subjects
0301 basic medicine ,Models, Molecular ,Sophora ,Pterocarpans ,Stereochemistry ,Cell Survival ,Stereoisomerism ,Biochemistry ,Plant Roots ,03 medical and health sciences ,chemistry.chemical_compound ,Structure-Activity Relationship ,Cell Line, Tumor ,Structure–activity relationship ,Humans ,Physical and Theoretical Chemistry ,Cell Proliferation ,Sophora flavescens ,Bicyclic molecule ,biology ,Cell Death ,Dose-Response Relationship, Drug ,Molecular Structure ,Activator (genetics) ,Chemistry ,Organic Chemistry ,biology.organism_classification ,Antineoplastic Agents, Phytogenic ,030104 developmental biology ,Nonane ,Drug Screening Assays, Antitumor ,Derivative (chemistry) - Abstract
Sophopterocarpan A (1), with a novel benzotetrahydrofuran-fused bicyclo [3.3.1] nonane ring, was isolated from the roots of Sophora flavescens Ait. Its unusual structure, including its stereochemistry, was determined on the basis of a comprehensive spectroscopic data analysis. A plausible biogenetic pathway for 1 is presented. Sophopterocarpan A was identified as a potential autophagy activator. Additionally, it was found that 1 exhibited cytotoxic activity in MCF-7 cells with an IC50 of 29.36 μM.
- Published
- 2017
49. Hepatoprotective acyl glycosides obtained from Erycibe hainanesis
- Author
-
Shuang Song, Ya-Wen An, Pei-Cheng Zhang, Zi-Ming Feng, Jian-Shuang Jiang, and Ya-Nan Yang
- Subjects
Lignan ,chemistry.chemical_classification ,biology ,Glycoside ,Plant Science ,biology.organism_classification ,Biochemistry ,chemistry.chemical_compound ,Column chromatography ,chemistry ,Galactosamine ,Organic chemistry ,Bioassay ,Convolvulaceae ,Agronomy and Crop Science ,Biotechnology - Abstract
An ongoing search for naturally occurring hepatoprotective constituents has identified three new acyl glycosides (1–3) and a new lignan glycoside (4) in the roots and stems of Erycibe hainanesis using various column chromatography methods. The structures of these compounds have been determined based on chemical and spectroscopic evidence, and the following bioassay indicates that all four glycosides have moderate hepatoprotective activities against d -galactosamine induced toxicity in WB-F344 rat hepatic epithelial stem-like cells.
- Published
- 2014
50. Dibenzoyl and Isoflavonoid Glycosides from Sophora flavescens: Inhibition of the Cytotoxic Effect of <scp>d</scp>-Galactosamine on Human Hepatocyte HL-7702
- Author
-
Jian-Shuang Jiang, Ya-Nan Yang, Yi Shen, Pei-Cheng Zhang, and Zi-Ming Feng
- Subjects
Stereochemistry ,Nitric Oxide Synthase Type II ,Pharmaceutical Science ,D galactosamine ,Galactosamine ,Benzoates ,Plant Roots ,Analytical Chemistry ,Isoflavonoid ,Drug Discovery ,Humans ,Cytotoxic T cell ,Glycosides ,Acetic Acid ,Flavonoids ,Pharmacology ,chemistry.chemical_classification ,Sophora flavescens ,Molecular Structure ,biology ,Organic Chemistry ,Glycoside ,biology.organism_classification ,Human hepatocyte ,Complementary and alternative medicine ,Biochemistry ,chemistry ,Hepatocytes ,Hepatic stellate cell ,Molecular Medicine ,Sophora ,Drugs, Chinese Herbal - Abstract
Twelve new dibenzoyl derivatives sophodibenzoside A-L (1-12) and five new isoflavone glycosides (13-17) have been isolated from the roots of Sophora flavescens together with eight known compounds (18-25). Notably, the use of acetic acid-d4 was required to enable identification of the dibenzoyl glycoside structures. Compounds 1, 2, 13, 14, and 19 exhibited weak inhibition of the cytotoxic effect of d-galactosamine on the human hepatic cell line HL-7702.
- Published
- 2013
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