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prenylated flavonoids from Glycyrrhiza uralensis as promising anti-cancer agents: a preliminary structure-activity study

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Journal of Chinese Pharmaceutical Sciences 2016年第1期25卷 23-29页

作者：唐叔南黄维季帅王永瑞裴道勇叶敏余四旺北京大学医学部药学院化学生物学系北京100191 北京大学医学部药学院天然药物学系北京100191

prenylated flavonoids are mainly distributed in Leguminosae and Moraceae plants, and they have been reported to possess various biological activities. Previously, we have reported a prenylated isoflavonoid, isoangustone A（IAA） from licorice（Glycyrrhiza uralensis）, which induces apoptosis in colorectal cancer cells by disrupting mitochondrial functions. In the present study, we compared a group of flavonoids from licorice with IAA for their anti-proliferation activities and effects on intracellular signaling. The results indicated that the isoprenyl groups on the A and B rings, the hydroxyl groups at the ortho position of isoprenyl on A ring and the conjugated plane of C ring might contribute to the anti-cancer activity of prenylated flavonoids. Based on the above structure-activity relationship, we further identified four prenylated flavonoids with similar anti-cancer activities from licorice. Taken together, our present study established a preliminary structure-activity relationship of anti-cancer prenylated flavonoids, and our data provided important leading compounds from licorice, which deserved further research and development.

关键词： prenylated flavonoids Licorice Anti-cancer Structure-activity relationship

Minor prenylated flavonoids from the Twigs of Macaranga adenantha and Their Cytotoxic Activity

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Natural Products and Bioprospecting 2015年第2期5卷 105-109页

作者： Da-Song Yang Shuang-Mei Wang Wei-Bing Peng Yong-Ping Yang Ke-Chun Liu Xiao-Li Li Wei-Lie Xiao Key Laboratory of Economic Plants and Biotechnology Germplasm Bank of Wild Species in Southwest ChinaInstitute of Tibetan Plateau Research at KunmingKunming Institute of BotanyChinese Academy of SciencesKunming 650201People’s Republic of China Biology Institute of Shandong Academy of Sciences Jinan 250014People’s Republic of China State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of SciencesKunming 650201People’s Republic of China

Three new minor prenylated flavonoids,named macadenanthins A–C(1–3),together with three known ones(4–6),were isolated from the twigs of Macaranga *** structures were elucidated on the basis of extensive spectroscopic analysis including NMR,UV and *** prenyl moieties in compounds 1–3 were further modified by cyclization and *** new compounds were tested for their cytotoxicity against four cancer cell lines(MCF-7,Hep G2,Hela and P388)and showed IC50 values in the range of 13.76–22.27 lM.

关键词： Macaranga adenantha prenylated flavonoids Macadenanthins A-C Cytotoxicity

New prenylated flavonoid glycosides derived from Epimedium wushanense byβ-glucosidase hydrolysis and their testosterone production-promoting effects

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Chinese Journal of Natural Medicines 2022年第9期20卷 712-720页

作者： SUN Xin-Guang PANG Xu LIANG Hai-Zhen ZHANG Jie WANG Bei LI Qi WANG Jie CHEN Xiao-Juan GUO Bao-Lin MA Bai-Ping Department of Pharmaceutical Sciences Beijing Institute of Radiation MedicineBeijing 100850China Institute of Medicinal Plant Development Chinese Academy of Medical Sciences&Peking Union Medical CollegeBeijing 100193China

Six new prenylated flavonoid glycosides,including four new furan-flavonoid glycosides wushepimedoside A–D(1–4)and two new prenyl flavonoid derivatives wushepimedoside E–F(5–6),and one know analog epimedkoreside B(7)were isolated from biotransformation products of the aerial parts of Epimedium *** structures were elucidated according to comprehensive analysis of HR-MS and NMR spectroscopic data,and the absolute configurations were assigned using experimental and calculated electronic circular dichroism(ECD)*** regulatory activity of compounds 1–7 on the production of testosterone in primary rat Leydig cells were investigated,and 4 and 5 exhibited testosterone production-promoting *** docking analysis suggested that bioactive compounds 4 and 5 showed the stable binding with 3β-HSD and 4 also had good affinity with Cyp17A1,which suggested that these compounds may regulate testosterone production through stimulating the expression of the above two key proteins.

关键词： Epimedium wushanense Biotransformation prenylated flavonoids Regulation on testosterone production

flavonoids isolated from Sinopodophylli Fructus and their bioactivities against human breast cancer cells

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Chinese Journal of Natural Medicines 2017年第3期15卷 225-233页

作者： WANG Qing-Hui GUO Shuai YANG Xue-Yan ZHANG Yi-Fan SHANG Ming-Ying SHANG Ying-Hui XIAO Jun-Jun CAI Shao-Qing Department of Natural Medicine School of Pharmaceutical SciencesPeking University Health Science CenterBeijing 100191China Department of Cell Biology School of Basic Medical SciencesPeking University Health Science CenterBeijing 100191China

Four prenylated flavonoids compounds 1-4,named sinopodophyllines A-D,and a flavonoid glycoside(compound 13),sinopodophylliside A,together with 19 known compounds(compounds 5-12 and 14-24) were isolated from the fruits of Sinopodophyllum *** structures of new compounds were elucidated by extensive spectroscopic analysis,including HRESIMS,1D and 2D *** 1-6,9-11,and 14-17 were tested for their cytotoxicity against human breast-cancer T47 D,MCF-7 and MDA-MB-231 cells in vitro,and compounds 2,5,6,10 and 11 showed significant cytotoxicity(IC50 values < 10 μmol·L^(-1))against T47 D cells.

关键词： Sinopodophylli Fructus prenylated flavonoids Flavonoid glycosides Breast-cancer cell lines