Six cytoxic annonaceous acetogenins from Annona squamosa seeds

CHEN Yong; CHEN Jianwei; WANG Yu; XU Shasha; LI Xiang

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Six cytoxic annonaceous acetogenins from Annona squamosa seeds

CHEN Yong 1,CHEN Jianwei 2,WANG Yu 2,XU Shasha 2,LI Xiang 2 * #

1.College of Pharmacy, Nanjing University of Chinese Medicine, NanJing 210046

2.College of Pharmacy,Nanjing University of Chinese Medicine,Nanjing,210046

*Correspondence author

#Submitted by

Subject:

Funding: Doctoral Fund of Ministry of Education of China（No.No.20113237110009）, 2011Program sponsored for scientific innovation research of college graduate in Jiansu provinc（No.No.790）, Jiansu Key Laboratory for Pharmacology and Safety Evaluation of Chinese Material Medica（No.No.P09018）, the Project Funded by the Priority Academic Program Development of Jiansu Higher Education Institutions（No.No.ysxk-2010）

Opened online:23 May 2012

Accepted by: none

Citation: CHEN Yong,CHEN Jianwei,WANG Yu.Six cytoxic annonaceous acetogenins from Annona squamosa seeds[OL]. [23 May 2012] http://en.paper.edu.cn/en_releasepaper/content/4478772

Custard apple (Annona squamosa L.) is an edible tropical fruit, and its seeds had been used in south China as folk medicine to treat "malignant sore" (cancer) and other usage as insecticide. Phytochemical investigation of the ethanol fraction of custard apple seeds led to the isolation of six new annonaceous acetogenins, annosquacins A-D (1-4), annosquatin A (5) and annosquatin B (6). Their structures were elucidated by spectroscopic analysis. Compounds 1-4 are adjacent bistetrahydrofuran annonaceous acetogenins. Compounds 5 and 6 are non-adjacent bistetrahydrofuran annonaceous acetogenins and the first examples in which the tetrahydrofuran ring system is located between C-9 and C-20. The absolute configurations of 1-6 were defined by the application of the Mosher method. Compounds 1-6 exhibited potent cytotoxic activity in vitro against five human tumor cell lines. 5 and 6 showed a high selectivity toward the MCF-7 and A-549 cell line respectively.

Keywords:Chemistry of Chinese Medicine; Annona squamosa L.; Annonaceous acetogenins; Annosquacins A-D; Annosquatin A; Annosquatin B; Cytotoxic activity

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