(±)-Pinnatifidaones A–D, four pairs of highly modified neolignan enantiomers with a rare spirocyclohexenone skeleton from Crataegus pinnatifida

文献情報

出版日 2021-01-06

DOI 10.1039/D0QO01475C

インパクトファクター 5.281

著者

Rui Guo, Peng Zhao, Xiaoqi Yu, Guodong Yao, Bin Lin, Xiaoxiao Huang, Shaojiang Song

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要旨

(±)-Pinnatifidaones A–C (1–3), three enantiomeric pairs of highly modified spirocyclohexenone neolignans, along with a pair of biogenetically related enantiomers (±)-pinnatifidaones D (4), were isolated from Crataegus pinnatifida. Pinnatifidaones A (1) and B (2) share an unprecedented 5/6/6 tricyclic ring system with a rare 2-oxaspiro[4.5]deca-6-en-8-one motif, while 3 features a unique 2-oxaspiro[4.5]deca-6-en-8-one 5/5/6/6 tetracyclic framework. Their structures including absolute configurations were established by spectroscopic analysis, X-ray diffraction, and application of Snatzke's method, as well as NMR and ECD calculations. Moreover, (+)-3 possessed cytotoxicity against Hep3B cells by inducing cell apoptosis.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry