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Highly Aromatic Norditerpenoid Heterodimers and Monomers from Trigonostemon fragilis

文献类型：期刊论文

作者Zhou, Jun-Su2; Cheng, Long2; Gao, Yuan2; Ge, Zhan-Peng2; Zhou, Bin1,2; Li, Jing-Ya2; Zhao, Jin-Xin1,2; Yue, Jian-Min1,2
刊名ENGINEERING
出版日期2024-07-01
卷号38页码:144-154
关键词Norditerpenoid heterodimer Trigonostemon fragilis Euphorbiaceae Trigofragiloid Structural revision Adenosine triphosphate-citrate lyase (ACLY) inhibitory activity
ISSN号2095-8099
DOI10.1016/j.eng.2023.09.0152095-8099
通讯作者Zhao, Jin-Xin(jxzhao@simm.ac.cn) ; Yue, Jian-Min(jmyue@simm.ac.cn)
英文摘要Four new norditerpenoid heterodimers with different dimerization patterns-namely, trigofragiloids A-C (denoted as compounds 1-3) and (+)- and (-)-trigofragiloid D (compound 4)-and three new phenanthrenone norditerpenoids-namely, trigofragiloids E-G (compounds 5-7)-were isolated from Trigonostemon fragilis. Compounds 1 and 2 feature a novel heterodimeric carbon skeleton formed by the conjugation of a tetra-norditerpenoid and an ennea-norditerpenoid; they have been identified as class 2 atropisomers by means of quantum chemical calculations. Compound 3 is an unprecedented phenylpropanoid-norditerpenoid adduct with a new dimerization pattern. Compounds (+)- and (-)-4 are the first example of S-shaped 1,4-dioxane-fused norditerpenoid dimers. Inspired by the structure elucidation of compound 4, two co-occurring analogues, actephilol A and epiactephilol A, were structurally revised as a pair of geometrical isomers and were identified as two pairs of enantiomers, (+)- and (-)-8 and (+)- and (-)-9, respectively. Their structures were characterized using a combined method. Notably, compound 7 exhibits remarkable adenosine triphosphate-citrate lyase (ACLY) inhibition with a halfmaximal inhibition concentration (IC50) value of (0.46 +/- 0.11) mu mol center dot L-1, as active as the positive control BMS-303141, and a molecular docking study offers deep insight into the interaction between compound 7 and ACLY. (c) 2023 THE AUTHORS. Published by Elsevier LTD on behalf of Chinese Academy of Engineering and Higher Education Press Limited Company.
WOS关键词DAPHNANE-TYPE DITERPENOIDS ; DEGRADED DITERPENOIDS ; INHIBITORY-ACTIVITIES ; A-C ; STEMS ; CONSTITUENTS ; TERPENOIDS ; TWIGS ; BARK ; INOS
资助项目National Natural Science Foundation of China[22237007] ; National Natural Science Foundation of China[22177122] ; Biological Resources Program of Chinese Academy of Sciences (CAS)[KFJ-BRP-008-001] ; Youth Innovation Promotion Associa-tion of Chinese Academy of Sciences[2022282]
WOS研究方向Engineering
语种英语
WOS记录号WOS:001299767600001
出版者ELSEVIER
源URL[http://119.78.100.183/handle/2S10ELR8/313023]  
专题新药研究国家重点实验室
通讯作者Zhao, Jin-Xin; Yue, Jian-Min
作者单位1.Bohai Rim Adv Res Inst Drug Discovery, Shandong Lab Yantai Drug Discovery, Yantai 264117, Peoples R China
2.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
推荐引用方式
GB/T 7714		 Zhou, Jun-Su,Cheng, Long,Gao, Yuan,et al. Highly Aromatic Norditerpenoid Heterodimers and Monomers from Trigonostemon fragilis[J]. ENGINEERING,2024,38:144-154.
APA Zhou, Jun-Su.,Cheng, Long.,Gao, Yuan.,Ge, Zhan-Peng.,Zhou, Bin.,...&Yue, Jian-Min.(2024).Highly Aromatic Norditerpenoid Heterodimers and Monomers from Trigonostemon fragilis.ENGINEERING,38,144-154.
MLA Zhou, Jun-Su,et al."Highly Aromatic Norditerpenoid Heterodimers and Monomers from Trigonostemon fragilis".ENGINEERING 38(2024):144-154.

入库方式： OAI收割

来源：上海药物研究所

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