Chemopreventive Agents from Physalis minima Function as Michael Reaction Acceptors

Ruizhi Men; Ning Li; Chihong Ding; Yingzhan Tang; Yachao Xing; Wanjing Ding; Zhongjun Ma

doi:10.4103/0973-1296.182153

Chemopreventive Agents from Physalis minima Function as Michael Reaction Acceptors

Pharmacogn Mag. 2016 May;12(Suppl 2):S231-6. doi: 10.4103/0973-1296.182153. Epub 2016 May 11.

Authors

Ruizhi Men¹, Ning Li¹, Chihong Ding², Yingzhan Tang¹, Yachao Xing¹, Wanjing Ding², Zhongjun Ma²

Affiliations

¹ School of Traditional Chinese Materia Medica, Ministry of Education, Wenhua Road 103, Shenyang 110016, PR China; Key Laboratory of Structure-Based Drug Design and Discovery (Shenyang Pharmaceutical University), Ministry of Education, Wenhua Road 103, Shenyang 110016, PR China.
² Institute of Marine Biology, Ocean College, Zhejiang University, Zijingang Campus, No. 866 Yuhangtang Road, Hangzhou 310058, PR China.

Abstract

Background: The fruits of some varieties of genus Physalis have been used as delicious fruits and functional food in the Northeast of China.

Materials and methods: To reveal the functional material basis, we performed bioactivity-guided phytochemical research and chemopreventive effect assay of the constituents from Physalis minima.

Results: It was demonstrated that the ethyl acetate extract of P. minima L. (EEPM) had potential quinone reductase (QR) inducing activity with induction ratio (IR, QR induction activity) value of 1.47 ± 0.24, and glutathione binding property as potential Michael reaction acceptors (with an α, β-unsaturated ketone moiety). Furthermore, bioactivity-guided phytochemical research led eight compounds (1-8), which were elucidated as 3-isopropyl-5-acetoxycyclohexene-2-one-1 (1), isophysalin B (2), physalin G (3), physalin D (4), physalin I (5), physordinose B (6), stigmasterol-3-O-β-D-glucopyranoside (7) and 5α-6β-dihydroxyphysalin R (8) on the basis of nuclear magnetic resonance spectroscopy analyses and HRESIMS. Then, isophysalin B (2) and physordinose B (6) showed significant QR inducing activity with IR value of 2.80 ± 0.19 and 2.38 ± 0.46, respectively.

Summary: An ultra-performance liquid chromatographic method with glutathione as the substrate was used to detect the Michael reaction acceptors in extracts of Physalis minima (EPM)We investigated the chemical constituents of EPM guided by biological activity methodIsophysalin B (1) and physordinose B (6) showed strong quinone reductase inducing activity with induction ratio values of 2.80 ± 0.19 and 2.38 ± 0.46This study generated useful information for consumers and many encourage researchers to utilize edible fruits from Physalis as a source of phytochemicals Abbreviations used: EPM: Extracts of Physalis minima, EEPM: Ethyl acetate extract of Physalis minima L., GSH: Glutathione, MRAs: Michael reaction acceptors, QR: Quinone reductase.

Keywords: Glutathione; Michael reaction acceptors; Physalis; Physalis minima; quinone reductase inducing activity.