Highly Aromatic Norditerpenoid Heterodimers and Monomers from Trigonostemon fragilis

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外文摘要：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 phenan-threnone 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 elu-cidation 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 half-maximal inhibition concentration(IC50)value of(0.46±0.11)μmol·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.

外文关键词：

Norditerpenoid heterodimerTrigonostemon fragilisEuphorbiaceaeTrigofragiloidStructural revisionAdenosine triphosphate-citrate lyase(ACLY)inhibitory activity

作者：

Jun-Su Zhou、Long Cheng、Yuan Gao、Zhan-Peng Ge、Bin Zhou、Jing-Ya Li、Jin-Xin Zhao、Jian-Min Yue

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作者单位：

State Key Laboratory of Drug Research,Shanghai Institute of Materia Medica,Chinese Academy of Sciences,Shanghai 201203,China

Shandong Laboratory of Yantai Drug Discovery,Bohai Rim Advanced Research Institute for Drug Discovery,Yantai 264117,China

基金：

National Natural Science Foundation of ChinaNational Natural Science Foundation of ChinaBiological Resources Program of Chinese Academy of Sciences(CAS)Youth Innovation Promotion Association of Chinese Academy of Sciences

项目编号：

2223700722177122KFJ-BRP-008-0012022282

出版年：

2024

DOI：

10.1016/j.eng.2023.09.015

工程(英文)

CSTPCDEI

ISSN：2095-8099

年,卷(期)：2024.38(7)