Withanolides from the stems and leaves of Physalis pubescens and their cytotoxic activity

Guiyang Xia; Yang Li; Jiawen Sun; Liqing Wang; Xiaolong Tang; Bin Lin; Ning Kang; Jian Huang; Lixia Chen; Feng Qiu

doi:10.1016/j.steroids.2016.09.002

Withanolides from the stems and leaves of Physalis pubescens and their cytotoxic activity

Steroids. 2016 Nov:115:136-146. doi: 10.1016/j.steroids.2016.09.002. Epub 2016 Sep 10.

Authors

Guiyang Xia¹, Yang Li², Jiawen Sun², Liqing Wang², Xiaolong Tang², Bin Lin³, Ning Kang⁴, Jian Huang², Lixia Chen⁵, Feng Qiu⁶

Affiliations

¹ Department of Natural Products Chemistry, School of Traditional Chinese Materia Medica, Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China; Tianjin State Key Laboratory of Modern Chinese Medicine and School of Chinese Materia Medica, Tianjin University of Traditional Chinese Medicine, 312 Anshanxi Road, Nankai District, Tianjin 300193, People's Republic of China.
² Department of Natural Products Chemistry, School of Traditional Chinese Materia Medica, Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China.
³ Department of Medicinal Chemistry, School of Pharmaceutical Engineering, Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China.
⁴ Tianjin State Key Laboratory of Modern Chinese Medicine and School of Chinese Materia Medica, Tianjin University of Traditional Chinese Medicine, 312 Anshanxi Road, Nankai District, Tianjin 300193, People's Republic of China.
⁵ Department of Natural Products Chemistry, School of Traditional Chinese Materia Medica, Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China. Electronic address: syzyclx@163.com.
⁶ Department of Natural Products Chemistry, School of Traditional Chinese Materia Medica, Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China; Tianjin State Key Laboratory of Modern Chinese Medicine and School of Chinese Materia Medica, Tianjin University of Traditional Chinese Medicine, 312 Anshanxi Road, Nankai District, Tianjin 300193, People's Republic of China. Electronic address: fengqiu20070118@163.com.

PMID: 27623060
DOI: 10.1016/j.steroids.2016.09.002

Abstract

A phytochemical study of Physalis pubescens L. afforded twelve compounds, including six new withanolides (1, 4, and 6i-9), four new withanolide glucosides (2, 3, 5, and 6), and two known withanolides (10 and 11). Their structures were established via extensive spectroscopic analysis. The absolute configuration of 3 was assigned using X-ray crystallography, and the absolute configurations of the 1,2-diol moiety in 1 were determined using the in situ dimolybdenum electronic circular dichroism method. Compounds 7, 9, and 10 exhibited significant cytotoxicity against human prostate cancer cells (C4-2B and 22Rvl), human renal carcinoma cells (786-O, A-498, Caki-2, and ACHN), human melanoma cells (A375 and A375-S2), and human normal hepatic cell line (L02) with IC₅₀ values in the range of 0.17-5.30μM.

Keywords: Cytotoxic activity; Physalis pubescens; Withanolides.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cell Line, Tumor
Cell Survival / drug effects
Crystallography, X-Ray
Female
Humans
Male
Molecular Structure
Physalis / chemistry*
Plant Extracts / chemistry*
Plant Extracts / pharmacology*
Plant Leaves / chemistry*
Plant Stems / chemistry*
Withanolides / chemistry*
Withanolides / pharmacology*

Substances

Plant Extracts
Withanolides