59 results on '"Lie-Jun, Huang"'
Search Results
2. Maillard Reaction Products with Anti-Tobacco Mosaic Virus Activities Generated in Processed Thermopsis lanceolata R. Br. Seed Extract
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Zhan-Xing Hu, Peng Zhang, Ji-Bin Zou, Qiao An, Ping Yi, Chun-Mao Yuan, Jue Yang, Wei Gu, Lie-Jun Huang, Li-Hua Zhao, and Xiao-Jiang Hao
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Organic Chemistry - Published
- 2022
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3. Synthesis and Antifungal Activity of Curcumol Derivatives
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Fu‐Tian Gao, Jun Jin, Jun‐You Jian, Liang Chen, Wei Gu, Chun‐Mao Yuan, Xiao‐Jiang Hao, and Lie‐Jun Huang
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Molecular Medicine ,Bioengineering ,General Chemistry ,General Medicine ,Molecular Biology ,Biochemistry - Published
- 2023
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4. Chemical Constituents of Primulina eburnea (Gesneriaceae) and Their Cytotoxic Activities
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Li‐Yuan Yang, Ping Yi, Jun‐Lei Chen, Yu‐Huan Li, Jue‐Lin Qiu, Zhao‐Yang Wang, Mao Fu, Chun‐Mao Yuan, Lie‐Jun Huang, Xiao‐Jiang Hao, and Wei Gu
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Molecular Medicine ,Bioengineering ,General Chemistry ,General Medicine ,Molecular Biology ,Biochemistry - Published
- 2023
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5. Quinoline alkaloids from the roots of Orixa japonica with the Anti-pathogenic Fungi Activities
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Jun‐You Jian, Yi‐Min Fan, Qian Liu, Jun Jin, Chun‐Mao Yuan, Wei Gu, Zhan‐Xing Hu, Lie‐Jun Huang, and Xiao‐Jiang Hao
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Molecular Medicine ,Bioengineering ,General Chemistry ,General Medicine ,Molecular Biology ,Biochemistry - Abstract
A new quinoline alkaloid, 5-hydroxy-6-methoxy-N-methyl-2-phenylquinoline-4-one (1), and seventeen known quinoline alkaloids (2-18) were isolated from the roots of Orixa japonica. The structure of 1 was determined by analysis of spectroscopic data. Among them, compounds 2, 3, and 13 were isolated from this plant for the first time. All isolates were screened for the anti-pathogenic fungi activities, including Rhizoctonia solani, Magnaporthe oryzae, and Phomopsis sp.. The results showed that five compounds (4, 8, 10, 11, and 12) exhibited significant anti-pathogenic fungi effects at 50.0 μg/mL. In special, compound 10 exhibited the best antifungal activities toward R. solani and M. oryzae with the IC50 values of 37.86 and 44.72 μM, respectively, better than that of the positive control, hymexazol (IC50 121.21 and 1518.18 μM, respectively). Moreover, eleven new quinoline alkaloids derivatives (12a-12k) were designed and synthesized to investigate the structure-activity relationships (SARs). The SARs analysis indicated that the furo [2, 3-b] quinoline skeleton and the methoxy at C-7 (compounds 8, 11, and 12) played a key role for improving the antifungal activities.
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- 2022
6. Hypermonones A—I, New Polyprenylated Acylphloroglucinols from Hypericum monogynum with Multidrug Resistance Reversal Activity
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Yan-Rong Zeng, Ya-Nan Li, Ping Yi, Yanmei Li, Wei Gu, Xiao-Jiang Hao, Lei Huang, Lie-Jun Huang, Jue Yang, Zhanxing Hu, and Chun-Mao Yuan
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Multiple drug resistance ,Phytochemistry ,Traditional medicine ,Chemistry ,General Chemistry ,Hypericum monogynum - Published
- 2021
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7. Hypermoins A–D: Rearranged Nor-Polyprenylated Acylphloroglucinols from the Flowers of Hypericum monogynum
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Yan-Rong Zeng, Wei Gu, Ya-Nan Li, Zhan-Xing Hu, Xiao-Jiang Hao, Lie-Jun Huang, Zi-Zhen Zhang, Yanmei Li, and Chun-Mao Yuan
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010405 organic chemistry ,Stereochemistry ,Organic Chemistry ,Absolute configuration ,Positive control ,010402 general chemistry ,Pathway analysis ,01 natural sciences ,0104 chemical sciences ,Multiple drug resistance ,chemistry.chemical_compound ,Biosynthesis ,chemistry ,MDR Modulators ,Hypericum monogynum - Abstract
Hypermonins A-D (1-4), four rearranged nor-polycyclic polyprenylated acylphloroglucinols (PPAPs) with unprecedented skeletons, together with two new biosynthesis related PPAPs (5 and 6) were isolated and identified from the flowers of Hypericum monogynum. Hypermoins A-D represented the first examples of highly modified norPPAPs characterized by a rare 7/6/6/5-tetracyclic system. From the biogenic synthesis pathway analysis, all isolates shared the same biosynthetic intermediate, and the addition of two methyls or one methyl to this intermediate through methyltranferase could generate different types of PPAPs (1-7). Their planner structures as well as absolute configuration were confirmed via spectroscopic analysis, ECD calculation, and X-ray crystallography. All isolates potentially reversed multidrug resistance (MDR) activity in both two cancer cells, HepG2/ADR and MCF-7/ADR. Specifically, hypermoin E (5) and hyperielliptone HA (7) were found to be the best MDR modulators with the reversal fold ranging from 41 to 236, which is higher than the positive control verapamil.
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- 2021
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8. Hymoins A–D: Two Pairs of Polyprenylated Acylphloroglucinols from Hypericum monogynum and Their Light-Induced Transformation
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Chun-Mao Yuan, Zhan-Xing Hu, Ya-Nan Li, Lie-Jun Huang, Xiao-Jiang Hao, Wei Gu, and Yan-Rong Zeng
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Circular dichroism ,010405 organic chemistry ,Stereochemistry ,Chemistry ,Organic Chemistry ,Light irradiation ,010402 general chemistry ,Ring (chemistry) ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,Transformation (genetics) ,Light induced ,Physical and Theoretical Chemistry ,Hypericum monogynum - Abstract
Hymoins A-D (1-4), two pairs of light-induced transformative polyprenylated acylphloroglucinols with an unprecedented pentacyclic skeleton, were isolated from the flowers of Hypericum monogynum. The first decarbonylative ring contraction of complex natural products was investigated by light irradiation. Their structures were elucidated by nuclear magnetic resonance analysis, X-ray crystallography, and electronic circular dichroism calculations. In addition, compound 3 showed moderate inhibition efficacy of the platelet-activating-factor-induced aggregation of rabbit platelets.
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- 2021
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9. Two new seco-polycyclic polyprenylated acylphloroglucinol from Hypericum sampsonii
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Lie-Jun Huang, Wei Gu, Ya-Nan Li, Chun-Mao Yuan, Xiao-Jiang Hao, Yan-Rong Zeng, Zi-Zhen Zhang, and Zhanxing Hu
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Chemistry ,Stereochemistry ,Resistant cancer ,Organic Chemistry ,Hypericum sampsonii ,Physical and Theoretical Chemistry ,Circular dichroism spectra ,Biochemistry - Abstract
Hypsampsone A (1) and hyperhexanone F (2), two novel seco-polycyclic polyprenylated acylphloroglucinols, were isolated from Hypericum sampsonii. Hypsampsone A (1) features the first spirocyclic system fused with 5/6/5/5 tetracyclic skeleton. Hyperhexanone F (2) represents the second novel 1,2-seco-bicyclo[3.3.1]-PPAP skeleton. Their structures were established by extensive spectroscopic analysis, computer-assisted structure elucidation software, and calculated electronic circular dichroism spectra. A plausible biogenetic pathway of 1 was also proposed. Compounds 1 and 2 showed moderate multidrug resistance reversal activity to adriamycin (ADR) resistant cancer cell lines, HepG2/ADR and MCF-7/ADR, with the fold-reversals ranging from 16 to 38 at noncytotoxic concentration of 10 μM.
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- 2021
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10. New sesquiterpeniod esters form Blumea balsamifera (L.) DC. and their anti-influenza virus activity
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Rongmei Gao, Yuhuan Li, Yan Xiong, Caixia Du, Chun-Mao Yuan, Lie-Jun Huang, Hua-Yong Lou, Wei Gu, Xiao-Jiang Hao, Yu Zhang, Zhan-Xing Hu, Ping Yi, Jiayu Zhang, and Junlei Chen
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biology ,Traditional medicine ,010405 organic chemistry ,Organic Chemistry ,Plant Science ,Asteraceae ,biology.organism_classification ,01 natural sciences ,Biochemistry ,Virus ,0104 chemical sciences ,Analytical Chemistry ,010404 medicinal & biomolecular chemistry ,Phytochemical ,Blumea balsamifera - Abstract
Phytochemical studies led to the isolation of five new sesquiterpeniod esters, named balsamiferine N-R, along with ten known compounds (6-15) from the leaves of Blumea balsamifera (L.) DC. The skel...
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- 2020
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11. Ethnobotanical study on medicinal plants from the Dragon Boat Festival herbal markets of Qianxinan, southwestern Guizhou, China
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Shengji Pei, Lie-Jun Huang, Jiayu Zhang, Zehuan Wang, Wei Gu, and Xiao-Jiang Hao
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0106 biological sciences ,Artemisia argyi ,Endangered species ,Ethnobotanical study ,Plant Science ,010603 evolutionary biology ,01 natural sciences ,lcsh:Botany ,Dragon boat festival ,Traditional knowledge ,China ,Medicinal plants ,lcsh:QH301-705.5 ,Qianxinan buyi and miao autonomous prefecture ,Ecology, Evolution, Behavior and Systematics ,Traditional medicine ,lcsh:QK1-989 ,Herbal markets ,Geography ,lcsh:Biology (General) ,Ethnobotany ,Conservation status ,Ethnomedicine ,Research Paper ,010606 plant biology & botany - Abstract
Dragon Boat Festival herbal markets in the Qianxinan Buyi and Miao Autonomous Prefecture of southwestern Guizhou have a long well-conserved history. These markets, which are a feature of Buyi and Miao traditional medicines, contain a rich diversity of medicinal plants and traditional medical knowledge. Today, people in southwestern Guizhou still believe that using herbs during the Dragon Boat Festival prevents and can treat disease. In this study, we identified the fresh herbal plants sold at the herbal markets of Xingren City and Zhenfeng County in Qianxinan Buyi and Miao Autonomous Prefecture and quantified their importance. We identified 141 plant species (belonging to 114 genera and 61 families). The plant family with the most species was Asteraceae (14 species). Informants reported that most medicinal plants are herbaceous, with 95.7% of plants used for decoction and 30.5% used for medicinal baths. Medicinal plants are most commonly used to treat rheumatism, injury, and abdominal diseases. The utilization frequency index and relative importance values indicated that Artemisia argyi and Acorus calamus are the most important plants sold at herbal markets during the Dragon Boat Festival. The price of medicinal materials sold in the market may serve as an indicator of the conservation status of species in the region. These findings indicate that the Dragon Boat Festival herbal markets in the Qianxinan Buyi and Miao Autonomous Prefecture fully embodies the characteristics of indigenous ethnomedicine and culture, and also exhibits the diversity of plant resources. We recommend that rare and endangered plants in this region be domesticated and protected.
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- 2020
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12. Hyperfols A and B: Two Highly Modified Polycyclic Polyprenylated Acylphloroglucinols from Hypericum perforatum
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Wei Gu, Yanmei Li, Lie-Jun Huang, Xiao-Jiang Hao, Chun-Mao Yuan, Hua-Yong Lou, Zhan-Xing Hu, Jun-You Jian, Ya-Nan Li, and Ping Yi
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Circular dichroism ,010405 organic chemistry ,Chemistry ,Stereochemistry ,Organic Chemistry ,Hypericum perforatum ,Physical and Theoretical Chemistry ,010402 general chemistry ,Cytotoxicity ,01 natural sciences ,Biochemistry ,0104 chemical sciences - Abstract
Two novel polycyclic polyprenylated acylphloroglucinols (PPAPs), hyperfols A (1) and B (2), and two known biosynthetically related precursors (3 and 4) were isolated from Hypericum perforatum. Compound 1 possesses an unprecedented 2,3-seco-PPAP with a fused 5/5/9/5 tetracyclic skeleton, and 2 features a 30-norPPAP. Their structures were established by spectroscopic analysis, computer-assisted structure elucidation software, and electronic circular dichroism calculations. Moreover, compounds 1 and 4 exhibit significant cytotoxicity against human erythroleukemia cells by inducing cell apoptosis.
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- 2020
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13. Three New Pregnanes Isolated from the Cynanchum auriculatum
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Yi‐Min Fan, Jun Jin, Jun‐You Jian, Wei Gu, Chun‐Mao Yuan, Zhan‐Xing Hu, Xiao‐Jiang Hao, and Lie‐Jun Huang
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Sapogenins ,Cynanchum ,Molecular Medicine ,Bioengineering ,General Chemistry ,General Medicine ,Glycosides ,Pregnanes ,Molecular Biology ,Biochemistry ,Plant Roots - Abstract
Three new compounds named cynansteroid A (1), cynansteroid B (2) and cynansteroid C (3), together with nine known C
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- 2022
14. Two new cytisine-type alkaloids from the seeds of
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Peng, Zhang, Ji-Bin, Zou, Qiao, An, Ping, Yi, Chun-Mao, Yuan, Lie-Jun, Huang, Wei, Gu, Zhan-Xing, Hu, and Xiao-Jiang, Hao
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Alkaloids ,Molecular Structure ,Seeds ,Fabaceae ,Azocines ,Antiviral Agents ,Quinolizines - Abstract
Two new (
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- 2022
15. The Cardiac Sapogenins from Periploca Forrestii
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Jun Jin, Man Meng, Jun-you Jian, Wei Gu, Chun-mao Yuan, Xiao-jiang Hao, and Lie-jun Huang
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- 2022
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16. Oreocharioside A-G, New Acylated C-Glycosylflavones from Oreocharis Auricula (Gesneriaceae)
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Rui-Xuan, Xie, Jun-Lei, Chen, Li-Qiang, Zhou, Xian-Jie, Fu, Chun-Mao, Yuan, Zhan-Xing, Hu, Lie-Jun, Huang, Xiao-Jiang, Hao, and Wei, Gu
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Pharmacology ,History ,Molecular Structure ,Polymers and Plastics ,Plant Extracts ,Drug Discovery ,Anti-Inflammatory Agents ,General Medicine ,Business and International Management ,Antioxidants ,Industrial and Manufacturing Engineering - Abstract
Seven new acylated C-glycosylflavones, oreocharioside A-G, together with two known compounds were isolated from the whole plant of Oreocharis auricula. Their structures were characterized by the comprehensive analysis of their NMR, IR, UV, CD spectra and HRESIMS data. All the new compounds were evaluated for the antioxidant and anti-inflammatory activities. The results showed that compounds 1 and 2 had significant DPPH and ABTS radical scavenging activities, with the IC
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- 2022
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17. A novelty pregnane C21-steroid from Cynanchum auriculatum
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Lie-jun Huang, Yi-min Fan, Jun Jin, Ping Yi, Wei Gu, Jun-you Jian, Chun-mao Yuan, and Xiao-jiang Hao
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Biochemistry ,Ecology, Evolution, Behavior and Systematics - Published
- 2022
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18. Two new secondary metabolites from Oreocharis auricula and their chemotaxonomic significance
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Wei Gu, Rui-xuan Xie, Jun-lei Chen, Chun-mao Yuan, Lie-jun Huang, Ping Yi, and Xiao-jiang Hao
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Biochemistry ,Ecology, Evolution, Behavior and Systematics - Published
- 2022
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19. Chemical constituents from the flowers of Hypericum monogynum L. with COX-2 inhibitory activity
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Lie-Jun Huang, Xiao-Jiang Hao, Wei Gu, Junlei Chen, Chun-Mao Yuan, Jue Yang, Wenwen He, Lulu Deng, Ya-Nan Li, Ping Yi, Yan-Rong Zeng, and Zhanxing Hu
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Plant Science ,Flowers ,Horticulture ,Hypericaceae ,Phloroglucinol ,Inhibitory postsynaptic potential ,Biochemistry ,chemistry.chemical_compound ,Flavonoid derivatives ,Ic50 values ,Hypericum monogynum ,Molecular Biology ,Taxonomy ,Traditional medicine ,biology ,Molecular Structure ,Chemistry ,General Medicine ,Biodiversity ,biology.organism_classification ,Multiple drug resistance ,Molecular Docking Simulation ,Cyclooxygenase 2 ,Chemical constituents ,Quercetin ,Hypericum - Abstract
Hypericum monogynum L. (Hypericaceae) has been used as a folk Chinese medicine for the treatment of inflammatory related diseases. Cyclooxygenase-2 (COX-2) is a crucial target for the development of agents to treat inflammation. To search for anti-inflammatory compounds from traditional Chinese medicines, a chemical constituent study along with COX-2 inhibitory activity analysis was performed for this plant. In this study, sixteen chemical monomers, including three undescribed oxidative degradation polycyclic polyprenylated acylphloroglucinols (PPAPs, hypemoins C–E), two undescribed PPAPs (hypemoins A and B), and 11 known compounds, were identified from the flowers of H. monogynum. Their structures were characterized by HRESIMS, NMR techniques, ECD, and single crystal X-ray diffraction. Four flavonoid derivatives showed remarkable COX-2 inhibitory activities, with IC50 values ranging from 0.220 ± 0.006 to 1.655 ± 0.098 μM. Among these compounds, the possible recognition mechanism between quercetin 3-(6″-O-caffeoyl)-β-3-D-galactoside and COX-2 was predicted by molecular docking analysis. Moreover, the multidrug resistance reversal activities for the selected compounds were evaluated.
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- 2021
20. Polycyclic polyprenylated acylphloroglucinol derivatives with neuroprotective effects from Hypericum monogynum
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Ya-Na Li, Wei Gu, Jun-You Jian, Xiao-Jiang Hao, Guanhua Du, Yan-Rong Zeng, Hua-Yong Lou, Chun-Mao Yuan, and Lie-Jun Huang
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Pharmacology ,Traditional medicine ,010405 organic chemistry ,Chemistry ,Organic Chemistry ,Pharmaceutical Science ,General Medicine ,01 natural sciences ,Neuroprotection ,0104 chemical sciences ,Analytical Chemistry ,010404 medicinal & biomolecular chemistry ,Complementary and alternative medicine ,Drug Discovery ,Molecular Medicine ,Hypericum monogynum - Abstract
A new polycyclic polyprenylated acylphloroglucinol (PPAP), hypermonin C (1), along with nine known PPAPs (2–10) were obtained from the leaves and twigs of Hypericum monogynum. The structures of the isolates were determined on the basis of extensive spectroscopic analysis. The neuroprotective effects of the isolates against several chemical-induced injuries in SH-SY5Y and PC12 cells were assessed, and most of the compounds exhibited significant protective effects at 10 μg/ml. Especially, three compounds (1, 3, and 7) showed excellent neuroprotective activity with a cell viability of 92.4% ∼ 95.8% in KCl-induced SH-SY5Y cell injury. Their preliminary structure-activity relationship was also discussed and the configuration of substituent in furohyperforin may be critical for the neuroprotective activity of PPAP derivatives.
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- 2019
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21. Synthesis of novel guttiferone E and xanthochymol derivatives with cytotoxicities by inducing cell apoptosis and arresting the cell cycle phase
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Jialei Song, Yanmei Li, Xin Lin, Dongsong Tian, Wei Gu, Yan-Hui Fu, Min Wen, Lie-Jun Huang, Chun-Mao Yuan, Yaacov Ben-David, Xiao-Jiang Hao, and Ya-Nan Li
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Spectrometry, Mass, Electrospray Ionization ,Magnetic Resonance Spectroscopy ,Cell cycle checkpoint ,Cell ,Apoptosis ,Resting Phase, Cell Cycle ,01 natural sciences ,HeLa ,Benzophenones ,03 medical and health sciences ,Cell Line, Tumor ,Drug Discovery ,medicine ,Humans ,Cyclin D1 ,Polycyclic Compounds ,MTT assay ,Cytotoxicity ,bcl-2-Associated X Protein ,030304 developmental biology ,Pharmacology ,0303 health sciences ,Leukemia ,Molecular Structure ,biology ,Cytotoxins ,010405 organic chemistry ,Chemistry ,Organic Chemistry ,Cell Cycle Checkpoints ,General Medicine ,Cell cycle ,biology.organism_classification ,Molecular biology ,0104 chemical sciences ,medicine.anatomical_structure ,Proto-Oncogene Proteins c-bcl-2 ,Cell culture - Abstract
The mixture of GX (guttiferone E and xanthochymol), an inseparable polycyclic polyprenylated acylphloroglucinol (PPAP), showed moderate cytotoxic activities. The chemical transformation of GX yielded three different types of PPAPs (1, 2, and 3/4). A series of analogs were prepared, and the structures of the 40 newly synthesized compounds were elucidated by 1D and 2D NMR and HR-ESI-MS. The derivatives were screened in vitro for antiproliferative activity against five human cancer cell lines: human leukemic cell lines (HEL and K562), cervical cancer cell line (Hela), human breast adenocarcinoma cell line (MCF-7), and human non-small cell lung cancer cell line (A549), using the MTT assay, and most of the derivatives showed good cytotoxic activities. Noticeably, compound 2, a novel tautomer with a hemiketal, exhibited selective cytotoxic activities against HEL (IC50 = 4.79 ± 0.23 μM) and K562 (IC50 = 7.69 ± 0.34 μM) leukemia cells. The mechanism studies indicated that compound 2 induced apoptosis and arrested the cell cycle at the G0/G1 phase in the HEL cell line. Furthermore, compound 2 activated the intrinsic pathway by reducing the expression of anti-apoptotic protein Bcl-2 and cell cycle-specific cyclin D1 and by enhancing the pro-apoptotic protein Bax. Moreover, the caspase-3 and PPRP1 levels were also upregulated. Our present results suggest that compound 2 is a potential candidate for developing novel anti-leukemia agents in the future.
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- 2019
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22. Hymoins A-D: Two Pairs of Polyprenylated Acylphloroglucinols from
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Yan-Rong, Zeng, Chun-Mao, Yuan, Ya-Nan, Li, Lie-Jun, Huang, Zhan-Xing, Hu, Wei, Gu, and Xiao-Jiang, Hao
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Magnetic Resonance Spectroscopy ,Molecular Structure ,Circular Dichroism ,Animals ,Rabbits ,Phloroglucinol ,Crystallography, X-Ray ,Nuclear Magnetic Resonance, Biomolecular ,Hypericum - Abstract
Hymoins A-D (
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- 2021
23. Anti-tobacco mosaic virus (TMV) activity of chemical constituents from the seeds of
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Zhan-Xing, Hu, Ji-Bin, Zou, Qiao, An, Ping, Yi, Chun-Mao, Yuan, Wei, Gu, Lie-Jun, Huang, Hua-Yong, Lou, Li-Hua, Zhao, and Xiao-Jiang, Hao
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Tobacco Mosaic Virus ,Molecular Structure ,Seeds ,Antiviral Agents ,Sophora - Abstract
Two new compounds, including one new arylbenzofuran (
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- 2021
24. Anti-tobacco mosaic virus (TMV) activity of chemical constituents from the seeds of Sophora tonkinensis
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Ji-Bin Zou, Ping Yi, Lie-Jun Huang, Zhanxing Hu, Li-Hua Zhao, Chun-Mao Yuan, Hua-Yong Lou, Wei Gu, Qiao An, and Xiao-Jiang Hao
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Pharmacology ,Mosaic virus ,Traditional medicine ,biology ,010405 organic chemistry ,Chemistry ,Organic Chemistry ,Sophora tonkinensis ,Pharmaceutical Science ,General Medicine ,biology.organism_classification ,01 natural sciences ,0104 chemical sciences ,Analytical Chemistry ,010404 medicinal & biomolecular chemistry ,Tobacco mosaic virus TMV ,Complementary and alternative medicine ,Chemical constituents ,Drug Discovery ,Tobacco mosaic virus ,Molecular Medicine - Abstract
Two new compounds, including one new arylbenzofuran (1) and one new pterocarpanoid (2), along with nine known ones, were isolated from the seeds of Sophora tonkinensis. The structures of the new compounds were elucidated based on a comprehensive spectroscopic data analysis. Compounds 2 and 3 exhibited good anti-tobacco mosaic virus (TMV) activities with the protective inhibition rate of 69.62% and 68.72% respectively, at concentration of 100 μg/ml.
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- 2021
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25. Thermlanseedlines A–G, seven thermopsine-based alkaloids with antiviral and insecticidal activities from the seeds of Thermopsis lanceolata R. Br
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Peng, Zhang, Qiao, An, Ping, Yi, Yue, Cui, Ji-Bin, Zou, Chun-Mao, Yuan, Yu, Zhang, Wei, Gu, Lie-Jun, Huang, Li-Hua, Zhao, Zhan-Xing, Hu, and Xiao-Jiang, Hao
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Pharmacology ,Insecticides ,Alkaloids ,Molecular Structure ,Seeds ,Drug Discovery ,General Medicine ,Antiviral Agents - Abstract
Seven undescribed thermopsine-based alkaloids (1-7), including one undescribed biogenetically related intermediate (7), were isolated from the seeds of Thermopsis lanceolata R. Br. Compound 1 possessed a 6/6-6 tricyclic skeleton, while compounds 2-6 represented three rare dimerization patterns constructed by quinolizidine alkaloids. Their structures were elucidated by comprehensive spectroscopic data analysis as well as ECD calculations. Biologically, compound 6 displayed significant anti-Tomato spotted wilt virus (TSWV) activity compared with the positive control ningnanmycin. Moreover, compound 1 exhibited good insecticidal activity against Aphis fabae with LC
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- 2022
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26. A C21-steroidal derivative suppresses T-cell lymphoma in mice by inhibiting SIRT3 via SAP18-SIN3
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Yaacov Ben-David, Chunlin Wang, Eldad Zacksenhaus, Wuling Liu, Cui Juiwei, Xiao-Jiang Hao, Klarke M. Sample, Krishnapriya Madhu Varier, Lie-Jun Huang, and Babu Gajendran
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0301 basic medicine ,Programmed cell death ,Phenotypic screening ,SIRT3 ,Protein Conformation ,Medicine (miscellaneous) ,Antineoplastic Agents ,Drug development ,Lymphoma, T-Cell ,Histone Deacetylases ,Article ,General Biochemistry, Genetics and Molecular Biology ,Target validation ,Mice ,03 medical and health sciences ,0302 clinical medicine ,Cell Line, Tumor ,Sirtuin 3 ,Target identification ,medicine ,Animals ,T-cell lymphoma ,Acute lymphocytic leukaemia ,Molecular Structure ,Cell growth ,Chemistry ,RNA-Binding Proteins ,medicine.disease ,Chromatin ,030104 developmental biology ,Gene Expression Regulation ,Cell culture ,030220 oncology & carcinogenesis ,Cancer cell ,Cancer research ,Histone deacetylase complex ,Steroids ,General Agricultural and Biological Sciences ,Co-Repressor Proteins - Abstract
The SIN3 repressor complex and the NAD-dependent deacetylase SIRT3 control cell growth, and development as well as malignant transformation. Even then, a little known about cross-talks between these two chromatin modifiers or whether their interaction explored therapeutically. Here we describe the identification of a C21-steroidal derivative compound, 3-O-chloroacetyl-gagamine, A671, which potently suppresses the growth of mouse and human T-cell lymphoma and erythroleukemia in vitro and preclinical models. A671 exerts its anti-neoplastic effects by direct interaction with Histone deacetylase complex subunit SAP18, a component of the SIN3 suppressor complex. This interaction stabilizes and activates SAP18, leading to transcriptional suppression of SIRT3, consequently to inhibition of proliferation and cell death. The resistance of cancer cells to A671 correlated with diminished SAP18 activation and sustained SIRT3 expression. These results uncover the SAP18-SIN3-SIRT3 axis that can be pharmacologically targeted by a C21-steroidal agent to suppress T-cell lymphoma and other malignancies., Gajendran et al. show that a C21-steroidal derivative called A671, 3-O-chloroacetyl-gagamine, suppresses the growth of T-cell lymphoma in mice. They find that A671 activates SAP18 to suppress the transcription of SIRT3, inhibiting cell growth. This study presents a new pharmacological target pathway for T-cell lymphoma.
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- 2020
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27. Two new seco-polycyclic polyprenylated acylphloroglucinol from
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Zi-Zhen, Zhang, Yan-Rong, Zeng, Ya-Nan, Li, Zhan-Xing, Hu, Lie-Jun, Huang, Wei, Gu, Xiao-Jiang, Hao, and Chun-Mao, Yuan
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Models, Molecular ,Prenylation ,Drug Resistance, Neoplasm ,MCF-7 Cells ,Molecular Conformation ,Humans ,Antineoplastic Agents ,Hep G2 Cells ,Phloroglucinol ,Hypericum - Abstract
Hypsampsone A (1) and hyperhexanone F (2), two novel seco-polycyclic polyprenylated acylphloroglucinols, were isolated from Hypericum sampsonii. Hypsampsone A (1) features the first spirocyclic system fused with 5/6/5/5 tetracyclic skeleton. Hyperhexanone F (2) represents the second novel 1,2-seco-bicyclo[3.3.1]-PPAP skeleton. Their structures were established by extensive spectroscopic analysis, computer-assisted structure elucidation software, and calculated electronic circular dichroism spectra. A plausible biogenetic pathway of 1 was also proposed. Compounds 1 and 2 showed moderate multidrug resistance reversal activity to adriamycin (ADR) resistant cancer cell lines, HepG2/ADR and MCF-7/ADR, with the fold-reversals ranging from 16 to 38 at noncytotoxic concentration of 10 μM.
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- 2020
28. Hyperfols A and B: Two Highly Modified Polycyclic Polyprenylated Acylphloroglucinols from
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Hua-Yong, Lou, Ya-Nan, Li, Ping, Yi, Jun-You, Jian, Zhan-Xing, Hu, Wei, Gu, Lie-Jun, Huang, Yan-Mei, Li, Chun-Mao, Yuan, and Xiao-Jiang, Hao
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Magnetic Resonance Spectroscopy ,Molecular Structure ,Circular Dichroism ,Humans ,Apoptosis ,Phloroglucinol ,Antineoplastic Agents, Phytogenic ,Hypericum - Abstract
Two novel polycyclic polyprenylated acylphloroglucinols (PPAPs), hyperfols A (
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- 2020
29. Polycyclic polyprenylated acylphloroglucinols with acetylcholinesterase inhibitory activities from Hypericum perforatum
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Yan-Rong Zeng, Ya-Nan Li, Lie-Jun Huang, Hua-Yong Lou, Ping Yi, Xiao-Jiang Hao, Zhan-Xing Hu, Chun-Mao Yuan, and Wei Gu
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Circular dichroism ,China ,Magnetic Resonance Spectroscopy ,Stereochemistry ,Phytochemicals ,Phloroglucinol ,Inhibitory postsynaptic potential ,01 natural sciences ,chemistry.chemical_compound ,Drug Discovery ,Ic50 values ,Pharmacology ,Quantum chemical ,biology ,Molecular Structure ,010405 organic chemistry ,Chemistry ,Circular Dichroism ,Hypericum perforatum ,General Medicine ,Plant Components, Aerial ,biology.organism_classification ,Acetylcholinesterase ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,Cholinesterase Inhibitors ,Hypericum ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
Six new polycyclic polyprenylated acylphloroglucinols, hyperfols C H (1–6), along with seven known ones (7–13), were isolated from the aerial parts of Hypericum perforatum. The structures were identified on the basis of comprehensive spectroscopic data analysis including 1D and 2D NMR, and the absolute configurations of the new compounds were determined by quantum chemical electronic circular dichroism (ECD) calculations. In addition, compounds 4 and 12 exhibited moderate acetylcholinesterase (AChE) inhibitory activities, with IC50 values of 20.32 and 27.37 μM, respectively.
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- 2020
30. C 21 -steroidal pregnane sapogenins and their derivatives as anti-inflammatory agents
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Chun-Mao Yuan, Wei Gu, Xiao-Jiang Hao, Bao-Jian Guo, Shao-Ru Chen, Ying Wang, Yitao Wang, and Lie-Jun Huang
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0301 basic medicine ,Chemistry ,Organic Chemistry ,Clinical Biochemistry ,Pregnane ,Pharmaceutical Science ,Sapogenin ,Pharmacology ,Biochemistry ,03 medical and health sciences ,TLR2 ,chemistry.chemical_compound ,030104 developmental biology ,TNF receptor associated factor ,Drug Discovery ,TLR3 ,TLR4 ,Molecular Medicine ,Ectopic expression ,Tumor necrosis factor alpha ,Molecular Biology - Abstract
During the screening of natural anti-inflammatory agent, we identified some C21-steroidal pregnane sapogenins or the derivatives to inhibit TLR2, TLR3, and TLR4-initiatedinflammatory responses respectively. Treatment with active compounds 10, 2j and 3p failed to impact tumor necrosis factor-α (TNF-α) induced nucleus translocation of NF-κB p65 subunit. However, these compounds regulated distinct canonical or non-canonical NF-κB family members. Ectopic expression of TNF receptor associated factor 6 (TRAF6) abrogated the inhibitory activity of the compounds on production of pro-inflammatory cytokines downstream of TLR4. These results suggested that compounds 10, 2j, and 3p suppressed TLR-initiated innate immunity through TRAF6 with differential regulation of NF-κB family proteins.
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- 2017
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31. Cytotoxic and anti-oxidant biphenyl derivatives from the leaves and twigs of Garcinia multiflora
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Lie-Jun Huang, Qing Rao, Yan-Hui Fu, Chun-Mao Yuan, Liping Wang, Wei Gu, Tao Huang, Dongsong Tian, Xiao-Jiang Hao, and Jian-Xin Zhang
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biology ,010405 organic chemistry ,Chemistry ,Biphenyl derivatives ,Plant Science ,Nuclear magnetic resonance spectroscopy ,Anti oxidant ,Mass spectrometry ,biology.organism_classification ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,Human tumor ,010404 medicinal & biomolecular chemistry ,Garcinia multiflora ,Organic chemistry ,Cytotoxic T cell ,Cytotoxicity ,Agronomy and Crop Science ,Biotechnology - Abstract
Three new biphenyl derivatives ( 1 – 3 ), together with five known compounds, were isolated from the leaves and twigs of Garcinia multiflora . Their structures were determined by extensive spectroscopic techniques including NMR spectroscopy and mass spectrometry. All eight isolates showed weak cytotoxicity on five human tumor cell lines. In addition, the three biphenyl derivatives showed moderate anti-oxidant activity with IC 50 values ranging from 7.78 to 8.78 μ M.
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- 2017
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32. Polycyclic polyprenylated acylphloroglucinol derivatives with neuroprotective effects from
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Yan-Rong, Zeng, Ya-Na, Li, Hua-Yong, Lou, Jun-You, Jian, Wei, Gu, Lie-Jun, Huang, Guan-Hua, Du, Chun-Mao, Yuan, and Xiao-Jiang, Hao
- Subjects
Plant Leaves ,Neuroprotective Agents ,Molecular Structure ,Animals ,Phloroglucinol ,PC12 Cells ,Hypericum ,Rats - Abstract
A new polycyclic polyprenylated acylphloroglucinol (PPAP), hypermonin C (
- Published
- 2019
33. Design, synthesis, and cytotoxic activities of novel hybrids of parthenolide and thiazolidinedione via click chemistry
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Yanmei Li, Juan Chen, Wei Gu, Jie Qiu, Chun-Mao Yuan, Lie-Jun Huang, Xiao-Jiang Hao, Jun-You Jian, Min Wen, and Ya-Nan Li
- Subjects
medicine.drug_class ,Pharmaceutical Science ,Antineoplastic Agents ,01 natural sciences ,Analytical Chemistry ,chemistry.chemical_compound ,Cell Line, Tumor ,Drug Discovery ,otorhinolaryngologic diseases ,medicine ,Cytotoxic T cell ,Humans ,Parthenolide ,Thiazolidinedione ,Cell Proliferation ,Pharmacology ,Molecular Structure ,010405 organic chemistry ,Chemistry ,Organic Chemistry ,General Medicine ,Combinatorial chemistry ,0104 chemical sciences ,Coupling (electronics) ,010404 medicinal & biomolecular chemistry ,Complementary and alternative medicine ,Design synthesis ,Click chemistry ,Molecular Medicine ,Click Chemistry ,Thiazolidinediones ,Drug Screening Assays, Antitumor ,Sesquiterpenes - Abstract
A series of novel parthenolide–thiazolidinedione hybrids have been synthesized via a click chemistry-mediated coupling between parthenolide and thiazolidinedione, and evaluated for their cytotoxic activities. The results indicated that all the hybrids showed moderate cytotoxic effects on human cancer cell lines, including human erythroleukemia cell line (HEL), prostate (PC3), and breast (MDA-MB-231) by MTT assay. In particular, compound VI-6 exhibited the best cytotoxic activities against the MDA-MB-231 cells with IC50 value of 2.07 µM, which was about eight times more active than that of the original compound (PTL). These interesting results might be used to develop novel lead scaffolds for potential anticancer agents.
- Published
- 2019
34. Cytotoxic phenolic constituents from Hypericum japonicum
- Author
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Lian Duan, Yanmei Li, Wei Zhu, Xiao-Jiang Hao, Jun-You Jian, Hua-Yong Lou, Wei Gu, Yan-Rong Zeng, Jie Qiu, Chun-Mao Yuan, Mingxing Zuo, Lie-Jun Huang, and Ping Yi
- Subjects
0106 biological sciences ,Circular dichroism ,Stereochemistry ,Plant Science ,Horticulture ,01 natural sciences ,Biochemistry ,chemistry.chemical_compound ,Structure-Activity Relationship ,Phenols ,Cell Line, Tumor ,Cytotoxic T cell ,Structure–activity relationship ,Humans ,MTT assay ,Cytotoxicity ,Molecular Biology ,Cell Proliferation ,Dose-Response Relationship, Drug ,Molecular Structure ,010405 organic chemistry ,General Medicine ,Nuclear magnetic resonance spectroscopy ,Antineoplastic Agents, Phytogenic ,0104 chemical sciences ,chemistry ,Cell culture ,Drug Screening Assays, Antitumor ,Derivative (chemistry) ,Hypericum ,010606 plant biology & botany - Abstract
Nine undescribed compounds, including five xanthone derivatives, two flavonoids, one 2-pyrone derivative, and one undescribed naturally occurring compound, along with 30 known phenolic compounds, were isolated from Hypericum japonicum. In addition, hyperjaponols A and B were identified as racemates. The structures and absolute configurations of the undescribed compounds were determined by comprehensive MS, NMR spectroscopy, and electronic circular dichroism (ECD) calculations. The cytotoxic effects of the isolated compounds on two human tumour cell lines (HEL and MDA-MB-231) were evaluated by the MTT assay. Eighteen compounds showed good inhibitory activities against the HEL cell line, with IC50 values of 3.53–18.7 μM, while nine compounds exhibited moderate cytotoxicity against the MDA-MB-231 cancer cell line, with IC50 values ranging from 4.92 to 10.75 μM. Their preliminary structure-activity relationship of the isolated compounds was also discussed.
- Published
- 2019
35. Hypermogins A–D, four highly modified polycyclic polyprenylated acylphloroglucinols from Hypericum monogynum
- Author
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Wei Gu, Ya-Nan Li, Xiao-Jiang Hao, Ping Yi, Chun-Mao Yuan, Jue Yang, Yan-Rong Zeng, and Lie-Jun Huang
- Subjects
chemistry.chemical_classification ,Circular dichroism ,Double bond ,010405 organic chemistry ,Stereochemistry ,Organic Chemistry ,Nuclear magnetic resonance spectroscopy ,010402 general chemistry ,Pinacol rearrangement ,Pathway analysis ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,Hydrolysis ,chemistry ,Drug Discovery ,Hypericum monogynum - Abstract
Four highly modified polycyclic polyprenylated acylphloroglucinols (PPAPs) with an unusual 6,5,5-tricyclic system, hypermogins A–D (1–4), together with one known analogue (5), were isolated from the flowers of Hypericum monogynum. From a possible biogenic synthesis pathway analysis, compounds 2 and 3 could be obtained by oxidation of a double bond and hydrolysis for 1 and 5. In addition, compound 3 might undergo a pinacol rearrangement to produce compound 4. The structures of the isolates were determined by comprehensive MS, NMR spectroscopy and electronic circular dichroism (ECD) calculations. All compounds significantly reversed multidrug resistance in MCF-7/ADR cells.
- Published
- 2021
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36. Synthesis and evaluation of antifungal activity of C21-steroidal derivatives
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Bin Wang, Shu-Zhen Mu, Chun-Mao Yuan, Xiao-Jiang Hao, Wei Gu, Jian-Xin Zhang, and Lie-Jun Huang
- Subjects
Antifungal ,Antifungal Agents ,Stereochemistry ,medicine.drug_class ,Clinical Biochemistry ,Molecular Conformation ,Pharmaceutical Science ,Microbial Sensitivity Tests ,Cynanchum ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Structure-Activity Relationship ,Ascomycota ,Drug Discovery ,Ic50 values ,medicine ,Structure–activity relationship ,Molecular Biology ,Mycelium ,Dose-Response Relationship, Drug ,biology ,010405 organic chemistry ,Chemistry ,Organic Chemistry ,Sclerotinia sclerotiorum ,biology.organism_classification ,0104 chemical sciences ,Cynanchum wilfordii ,Molecular Medicine ,Steroids - Abstract
The antifungal activities of eleven C21-steroidal compounds isolated from Cynanchum wilfordii, together with thirty-six derivatives of caudatin and qingyangshengenin were evaluated on Sclerotinia sclerotiorum and other five fungal strains by the mycelium growth rate method. Four derivatives 1k, 1y, 10d, and 10j exhibited much stronger inhibitions on growth of S. sclerotiorum with IC50 values of 0.0084, 0.0049, 0.0053, and 0.0034 μM, respectively.
- Published
- 2016
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37. A new acorane sesquiterpenes of Lysionotus pauciflorus maxim. Form Guizhou province, China
- Author
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Ping Yi, Caixia Du, Yu Zhang, Wei Gu, Yan Xiong, Lie-Jun Huang, Chun-Mao Yuan, Jiayu Zhang, and Xiao-Jiang Hao
- Subjects
Lysionotus ,010405 organic chemistry ,Biology ,biology.organism_classification ,Sesquiterpene ,01 natural sciences ,Biochemistry ,Gesneriaceae ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,chemistry.chemical_compound ,Lysionotus pauciflorus ,chemistry ,Genus ,Botany ,Maxim ,Ecology, Evolution, Behavior and Systematics - Abstract
A new acorane sesquiterpene (1), together with fourteen known compounds were isolated from the whole plant of Lysionotus pauciflorus Maxim. The chemical structures of the compounds were identified by physio-chemical properties and 1D-NMR, 2D-NMR, ESI-MS, IR and ECD spectra. Among them, six compounds (1, 4, 6, 7, 13, 15) were first found in the genus Lysionotus. The chemotaxonomic significance of the isolated compounds in the genus Lysionotus and family Gesneriaceae were discussed.
- Published
- 2020
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38. A new adduct of iriflophene and flavonoid from Sedum aizoon L
- Author
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Jiayu Zhang, Yan Xiong, Chun-Mao Yuan, Wei Gu, Lie-Jun Huang, Ping Yi, Xiao-Jiang Hao, and Caixia Du
- Subjects
chemistry.chemical_classification ,biology ,010405 organic chemistry ,Stereochemistry ,Flavonoid ,Aizoon ,biology.organism_classification ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,Adduct ,010404 medicinal & biomolecular chemistry ,chemistry ,Sedum aizoon ,Spectral data ,Ecology, Evolution, Behavior and Systematics - Abstract
A new adduct of iriflophene and flavonoid, 1, 8, 10, 10b-tetrahydroxy-3-methoxy-5a-(3,4-dihydr- oxyphenyl)-9-(4-hydroxybenzoyl)-5a,10b-dihydro-11H-benzofuro[2,3-b]chromen-11-one (1), together with six known compounds were isolated from the EtOH extract from Sedum aizoon L. Their chemical structures were elucidated by analyses of spectral data. The chemotaxonomic analysis of the compounds was discussed, compounds 1–4 provide important chemotaxonomic markers for S. aizoon.
- Published
- 2020
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39. Chemical constituents from Valeriana officinalis L. var. Iatifolia Miq. and their chemotaxonomic significance
- Author
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Li He, Wei Gu, Chun-Mao Yuan, Shuliang Wang, Lie-Jun Huang, Xiao-Jiang Hao, Ya-Nan Li, Yan-Rong Zeng, and Zhan-Xing Hu
- Subjects
010404 medicinal & biomolecular chemistry ,Valerianaceae ,Valeriana officinalis ,biology ,Traditional medicine ,010405 organic chemistry ,Chemical constituents ,Officinalis ,biology.organism_classification ,01 natural sciences ,Biochemistry ,Ecology, Evolution, Behavior and Systematics ,0104 chemical sciences - Abstract
Twenty-one compounds, including four monoterpenoids (1–4) (two new natural products, 1 and 2), four sesquiterpenes (5–8), two iridoids (9 and 10), four steroids (11–14), five phenolic compounds (15–19), and two alkaloids (20 and 21), were isolated from the roots of Valeriana officinalis L. var. Iatifolia Miq. Their chemical structures were established by spectroscopic methods and further confirmed by comparison with published data in the literature. Among them, eight compounds (1, 2, 6–8, 13, 18, and 21) are being reported from the family Valerianaceae for the first time, and compounds 9–12 were obtained from V. officinalis for the first time. The chemotaxonomic significance of the isolated compounds is discussed.
- Published
- 2020
- Full Text
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40. Phenolic derivatives from Garcinia multiflora Champion ex Bentham and their chemotaxonomic significance
- Author
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Lie-Jun Huang, Wei Gu, Hao-Jie Yang, Xiao-Jiang Hao, Chun-Mao Yuan, Yan-Rong Zeng, and Dongsong Tian
- Subjects
010404 medicinal & biomolecular chemistry ,biology ,Phytochemical ,Traditional medicine ,010405 organic chemistry ,Garcinia multiflora ,Ic50 values ,Garcinia ,biology.organism_classification ,01 natural sciences ,Biochemistry ,Ecology, Evolution, Behavior and Systematics ,0104 chemical sciences - Abstract
A phytochemical investigation of the leaves and twigs of Garcinia multiflora Champion ex Bentham led to the isolation of eleven phenolic derivatives, including a new polycyclic polyprenylated acylphloroglucinol (PPAP, 1), five known PPAPs (2–6), three xanthones (7–9), a benzophenone (10), and a methyl phenyl acetate derivative (11). Their structures were established by extensive spectroscopic analysis, including HR-ESI-MS and NMR. Five compounds (1, 2, 4, 5, and 11) were first found in the genus Garcinia, of which compounds 1 and 11 were reported from the family Guttiferae for the first time. The chemotaxonomic significance of the isolated compounds was discussed. Furthermore, six PPAPs showed good cytotoxicities with IC50 values ranging from 1.79 to 9.40 μM.
- Published
- 2020
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41. Two Unusual Polycyclic Polyprenylated Acylphloroglucinols, Including a Pair of Enantiomers from Garcinia multiflora
- Author
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Jian-Xin Zhang, Lie-Jun Huang, Chen Yan, Xiao-Jiang Hao, Yan Li, Chun-Mao Yuan, Wei Gu, Chonglin Yang, Yuan Ma, Yang Li, Ping Yi, Yi-Min Fan, and Tao Huang
- Subjects
Circular dichroism ,Stereochemistry ,HL-60 Cells ,Stereoisomerism ,Phloroglucinol ,Biochemistry ,HeLa ,chemistry.chemical_compound ,Humans ,Molecule ,Physical and Theoretical Chemistry ,Molecular Structure ,biology ,Chemistry ,Organic Chemistry ,Tridecane ,biology.organism_classification ,Antineoplastic Agents, Phytogenic ,Garcinia multiflora ,Drug Screening Assays, Antitumor ,Enantiomer ,Garcinia ,Lysosomes ,Human cancer ,HeLa Cells - Abstract
Two polycyclic polyprenylated acylphloroglucinols, garcimulins A and B ((+/-)-1 and 2), including a pair of enantiomers with the unique caged tetracyclo[5.4.1.1(1,5).0(9,13)]tridecane skeleton were isolated from Garcinia multiflora. Their structures and absolute configurations were determined by extensive analysis of spectroscopic data and electronic circular dichroism (ECD) calculations. Compounds 1 and 2 exhibited cytotoxic activities against five human cancer cell lines in vitro (IC50 3.42-13.23 mu M). The acidification of lysosomes in HeLa cell was obviously affected by compound 2.
- Published
- 2015
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42. Chromanopyrones and a flavone from Hypericum monogynum
- Author
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Chun-Mao Yuan, Xiao-Jiang Hao, Yan-Rong Zeng, Wei Gu, Liping Wang, Ping Yi, Wan-Xia Yang, Lie-Jun Huang, and Zhan-Xing Hu
- Subjects
Glycoside Hydrolase Inhibitors ,Stereochemistry ,01 natural sciences ,Flavones ,Antioxidants ,chemistry.chemical_compound ,Alpha-Glucosidases ,Drug Discovery ,Ic50 values ,Hypericum monogynum ,IC50 ,Pharmacology ,chemistry.chemical_classification ,biology ,Molecular Structure ,010405 organic chemistry ,Chemistry ,alpha-Glucosidases ,General Medicine ,biology.organism_classification ,Pyrone ,0104 chemical sciences ,Plant Leaves ,010404 medicinal & biomolecular chemistry ,Pyrones ,Hypericum - Abstract
Six new compounds, including three pyrone derivatives (2-4), one new flavone (5), and two new naturally-occurring compounds (1 and 6), together with 16 known compounds were isolated from the leaves and twigs of Hypericum monogynum. In addition, compounds 2-4 are racemates. Their structures and absolute configurations were determined on the basis of extensive analysis of spectroscopic data and ECD calculation. All compounds were evaluated for the inhibitory effects on α-glucosidase, compounds 1, 5, and 7 showed moderate inhibitory activities with IC50 values of 161.46, 257.78, and 11.54μg/ml, respectively. Compound 8 exhibited weak anti-oxidant activity with IC50 value of 12.55μg/ml.
- Published
- 2017
43. C
- Author
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Lie-Jun, Huang, Shao-Ru, Chen, Chun-Mao, Yuan, Wei, Gu, Bao-Jian, Guo, Yi-Tao, Wang, Ying, Wang, and Xiao-Jiang, Hao
- Subjects
Lipopolysaccharides ,Structure-Activity Relationship ,Sapogenins ,Dose-Response Relationship, Drug ,Molecular Structure ,Anti-Inflammatory Agents ,Cytokines ,Humans ,Cells, Cultured - Abstract
During the screening of natural anti-inflammatory agent, we identified some C
- Published
- 2017
44. Seco-pregnane steroidal glycosides from the roots of Cynanchum atratum and their anti-TMV activity
- Author
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Chen Yan, Xiao-Jiang Hao, Jian-Xin Zhang, Ying Yan, Lie-Jun Huang, Tao Huang, Kai-xing Liu, Sheng Liu, and Shu-Zhen Mu
- Subjects
Steroidal glycosides ,Stereochemistry ,Positive control ,Microbial Sensitivity Tests ,Coat protein ,Antiviral Agents ,Plant Roots ,chemistry.chemical_compound ,Western blot ,Tobacco ,Drug Discovery ,medicine ,Tobacco mosaic virus ,Secosteroids ,Glycosides ,Plant Diseases ,Pharmacology ,Molecular Structure ,Mosaic virus ,medicine.diagnostic_test ,Chemistry ,Pregnane ,Phytosterols ,Vincetoxicum ,General Medicine ,Saponins ,Tobacco Mosaic Virus ,Cynanchum atratum - Abstract
Fifteen new seco -pregnane steroidal glycosides cynanosides A–O ( 1 – 15 ) together with twenty-seven known ones were isolated from the roots of Cynanchum atratum . The structures of 1 – 15 were determined by extensive analysis of spectroscopic data. The anti-tobacco mosaic virus (TMV) activity of these steroidal glycosides was screened by the conventional half-leaf method, enzyme-linked immunosorbent assay, and Western blot methods, most of them showed potent anti-TMV activity. Among them, compounds 1 , 7 , 13 , 28 and 31 showed significantly anti-TMV activity with an IC 50 value of 20.5, 18.6, 22.0, 19.2 and 22.2 μg/mL, respectively, and were much more effective than the positive control, ningnanmycin (IC 50 = 49.6 μg/mL).
- Published
- 2014
- Full Text
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45. Synthesis and the hepatoprotective activity of dibenzocyclooctadiene lignan derivatives
- Author
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Jing-Zhen Shi, Tao He, Qing-Yao Wang, Shu-Zhen Mu, Xiao-Jiang Hao, Chen Yan, Tian-yun Fan, Sheng Liu, and Lie-Jun Huang
- Subjects
Cell Survival ,Stereochemistry ,Clinical Biochemistry ,Molecular Conformation ,Pharmaceutical Science ,Positive control ,Biochemistry ,Lignans ,Cyclooctanes ,Structure-Activity Relationship ,chemistry.chemical_compound ,Drug Discovery ,Humans ,Structure–activity relationship ,Carbon Tetrachloride ,Molecular Biology ,Cell survival ,Schizandrin B ,Dibenzocyclooctadiene lignan ,Dose-Response Relationship, Drug ,Organic Chemistry ,Schisanhenol ,Cell survival rate ,Liver ,chemistry ,Carbon tetrachloride ,Molecular Medicine - Abstract
The halogenated and oxidized derivatives (1a-1e, 1a'-1c', 2a-2d, 2a'-2b', 3a-3e, 3' and 3a'-3b') of schizandrin (1), schizandrin B (2) and schisanhenol (3) were synthesized. The hepatoprotective effects of these dibenzocyclooctadiene lignan analogues against CCl4-induced injury were preliminarily evaluated. Most of the analogues exhibited higher protective effects than the positive control biphenyldicarboxylate (DDB). Among these active analogues, dichloroschisanhenol (3a) exhibited the strongest protective activity (cell survival rate exceeding 98.0%).
- Published
- 2014
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46. Garmultins A-G, Biogenetically Related Polycyclic Acylphloroglucinols from Garcinia multiflora
- Author
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Xin Xiao, Yi Min Fan, Dong Song Tian, Ying-Tong Di, Lie Jun Huang, Wei Gu, Lei Xia, Yaacov Ben-David, Xiao-Jiang Hao, Ping Yi, and Chun Mao Yuan
- Subjects
Circular dichroism ,Stereochemistry ,Cell Survival ,Acylation ,HL-60 Cells ,Decane ,Phloroglucinol ,010402 general chemistry ,01 natural sciences ,Biochemistry ,chemistry.chemical_compound ,Molecule ,Humans ,Physical and Theoretical Chemistry ,Polycyclic Aromatic Hydrocarbons ,biology ,Molecular Structure ,010405 organic chemistry ,Organic Chemistry ,biology.organism_classification ,Antineoplastic Agents, Phytogenic ,0104 chemical sciences ,chemistry ,Garcinia multiflora ,A549 Cells ,MCF-7 Cells ,Undecane ,Garcinia - Abstract
Garmultins A and B (1 and 2), two polycyclic polyprenylated acylphloroglucinols characterized by the coupling of two novel cages, 2,11-dioxatricyclo[4.4.1.03,9]undecane and tricyclo[4.3.1.03,7]decane, along with five biogenetically related analogues (3–7), were isolated from Garcinia multiflora. Their structures and absolute configurations were determined by extensive NMR analysis, X-ray crystallography, and electronic circular dichroism calculations. Three compounds were capable of inhibiting oncogene expression and inducing apoptosis in human erythroleukemia cells.
- Published
- 2016
47. Alkaloids from Daphniphyllum oldhami
- Author
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Lie-Jun Huang, Chun-Shun Li, Ying-Tong Di, Xiao-Sheng Yang, Xiao-Jiang Hao, Shu-Zhen Mu, Jun-Song Wang, Ye Wang, Hong-Ping He, Yu Zhang, and Xin Fang
- Subjects
Quinolizidines ,Stereochemistry ,Molecular Conformation ,Pharmaceutical Science ,Daphniphyllum oldhami ,Pharmacognosy ,Crystallography, X-Ray ,Analytical Chemistry ,chemistry.chemical_compound ,Alkaloids ,Drug Discovery ,Nuclear Magnetic Resonance, Biomolecular ,Daphniphyllum ,Pharmacology ,chemistry.chemical_classification ,Plants, Medicinal ,Quinolizidine ,Natural product ,Molecular Structure ,biology ,Alkaloid ,Saxifragaceae ,Organic Chemistry ,biology.organism_classification ,Complementary and alternative medicine ,chemistry ,Molecular Medicine ,Two-dimensional nuclear magnetic resonance spectroscopy ,Platelet Aggregation Inhibitors ,Lactone ,Drugs, Chinese Herbal - Abstract
Four new Daphniphyllum alkaloids, daphnioldhanines H-K ( 1- 4), along with 34 known alkaloids, were isolated from Daphniphyllum oldhami. The known alkaloid dehydrodaphnigraciline ( 5) is now reported as a natural product. Their structures were elucidated by spectroscopic methods, especially 2D NMR techniques. The effects against platelet aggregation of compounds 1, 3, and 5 were evaluated, and 3 showed stronger activity against platelet aggregation induced by PAF. This is the first report of quinolizidine alkaloids from the genus Daphniphyllum.
- Published
- 2008
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48. Diterpene alkaloids and diterpenes from Spiraea japonica and their anti-tobacco mosaic virus activity
- Author
-
Wei Gu, Xin-Ying Mao, Yuan Ma, Xiao-Jiang Hao, Yi-Min Fan, Chun-Mao Yuan, Tao Huang, Chen Yan, Lie-Jun Huang, and Jian-Xin Zhang
- Subjects
0301 basic medicine ,Positive control ,Biology ,01 natural sciences ,Antiviral Agents ,03 medical and health sciences ,chemistry.chemical_compound ,Structure-Activity Relationship ,Alkaloids ,Drug Discovery ,Botany ,Tobacco mosaic virus ,Pharmacology ,Natural product ,Mosaic virus ,Molecular Structure ,010405 organic chemistry ,Plant Extracts ,General Medicine ,biology.organism_classification ,0104 chemical sciences ,Spiraea ,Tobacco Mosaic Virus ,030104 developmental biology ,chemistry ,Spiraea japonica ,Diterpene ,Diterpenes - Abstract
Five new naturally occurring natural products, including two atisine-type diterpene alkaloids (1 and 2), two atisane-type diterpenes (3 and 4), and a new natural product spiramine C2 (5), along with nine known ones (6-14), were isolated from the ethanolic extracts of the whole plant of Spiraea japonica var. acuminata Franch. Their structures were elucidated by extensive spectroscopic analysis. The anti-tobacco mosaic virus (TMV) activities of all the compounds were evaluated by the conventional half-leaf method. Six compounds (2, 3, 6, 7, 11, and 12) exhibited moderate activities at 100 μg/mL with inhibition rates in the range of 69.4-92.9%, which were higher than that of the positive control, ningnanmycin. Their preliminary structure-activity relationships were also discussed.
- Published
- 2015
49. A novel isocoumarin with anti-influenza virus activity from Strobilanthes cusia
- Author
-
Li-ping Wang, Wei Gu, Wei Wang, Lie-Jun Huang, Xiao-Nian Li, Chun-Mao Yuan, Yu Zhang, and Xiao-Jiang Hao
- Subjects
Magnetic Resonance Spectroscopy ,Stereochemistry ,Orthomyxoviridae ,Antiviral Agents ,Plant Roots ,Virus ,Mass Spectrometry ,chemistry.chemical_compound ,X-Ray Diffraction ,Acanthaceae ,Drug Discovery ,Moiety ,Pharmacology ,biology ,Molecular Structure ,General Medicine ,Nuclear magnetic resonance spectroscopy ,biology.organism_classification ,In vitro ,Isocoumarin ,Biochemistry ,chemistry ,Isocoumarins ,Strobilanthes ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
Strobilanthes A (1), a novel isocoumarin with an unusual tetrahydro-4H-pyran-4-one moiety fused isocoumarin core skeleton, together with a known compound (2) was isolated from Strobilanthes cusia. Its chemical structures were elucidated by 2D NMR spectroscopy, mass spectrometry and single-crystal X-ray diffraction analysis. The biosynthetic pathway of 1 could be supposed to be originally derived from 3-methylisocoumarin, a product of AA-MA pathway. Both of two compounds displayed anti-influenza virus activity in vitro.
- Published
- 2015
50. [Study on chemical constituents of Inula cappa]
- Author
-
Li-hua, Zheng, Xiao-jiang, Hao, Chun-mao, Yuan, Lie-jun, Huang, Jian-xin, Zhang, Fen, Dong, Tian-yun, Fan, Gui-hui, Wu, Yan, Chen, Yuan, Ma, Yi-min, Fan, and Wei, Gu
- Subjects
Spectrometry, Mass, Electrospray Ionization ,Molecular Structure ,Inula ,Drugs, Chinese Herbal - Abstract
Column chromatographies over silica gel, Sephadex LH-20, reverse phase C18, and MCI, and semi-preparative HPLC were used for separation and purification of constituents from Inula cappa. The 22 compounds were obtained and their strutures were determined by NMR and MS spectra data as nine flavonoids: luteolin (1), apigenin (2), chrysoeriol (3), artemetin (4), 2', 5-di- hydroxy-3, 6, 7, 4', 5'-pentamethoxyflavone (5), chrysosplenol C (6), apigenin-5-0-β-D-glucopyranoside (7), luteolin-3-methyl, luteolin-3-methylether-4'-0-β-D-glucopyranoside (8), luteolin-4'-0-β-D-glucopyranoside (9); four triterpenes: darma-20, 24-dien- 3β-0-acetate (10), darma-20, 24-dien-3β-ol (11), epirfiedelanol (12), friedelin (13); three coumarins: scopoletin (14) , isosco- poletin (15) , scopolin(16) , and other types of compounds stigmasta-5, 22-dien-3β-0-7-one (17), stigmasterol (18), palmitic acid (19), linoleic acid (20), linoleic acid methyl ester (21), (E) -9, 12, 13-trihydroxyoetadee-10-enoie acid (22). Compound 5 is a new natural product. Compounds 3-9, 15, 17, 21, and 22 were isolated from this genus for the first time.
- Published
- 2015
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