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Antiproliferative withanolides from several Solanaceous species
Zhang, Huaping Cao, Cong-Mei Gallagher, Robert J. Timmermann, Barbara N.
Zhang, Huaping
Cao, Cong-Mei
Gallagher, Robert J.
Timmermann, Barbara N.
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Abstract
To date, our work on Solanaceous species (Datura wrightii, Jaborosa caulescens, Physalis hispida, P. longifolia, Vassobia breviflora, and Withania somnifera) has resulted in the isolation of 65 withanolides, 31 of which were new, as well as the semi-synthesis of a further 30 withanolides. Structure identification and MTS assay-based antiproliferative evaluation of these 95 compounds revealed that a Δ2-1-oxo functionality in ring A; in conjunction with either a 5β,6β-epoxy or 5α-chloro-6β-hydroxy moiety in ring B; are the minimum structural requirements for withanolides to produce potent cytotoxic activity. Such structural-activity relationship analysis (SARA) also revealed that oxygenation (the –OH or –OR groups) at C-4, 7, 11, and 12; as well as C-14 to C-28; did not contribute toward the observed antiproliferative activity. Herein we present a complete overview of our work as it relates to the withanolides reported from 1965 to 2013.
Description
This is an Accepted Manuscript of an article published by Taylor & Francis in Natural Product Research in November 2014, available online: http://www.tandfonline.com/10.1080/14786419.2014.919286.
Date
2014-11
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Taylor & Francis
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Keywords
Withanolide, Solanaceae, Datura wrightii, Jaborosa caulescens, Physalis hispida, Physalis longifolia, Vassobia breviflora, Withania somnifera, Antiproliferative, Cytotoxicity, Structure activity relationship
Citation
Zhang, H., Cao, C.-M., Gallagher, R. J., & Timmermann, B. N. (2014). Antiproliferative withanolides from several Solanaceous species. Natural Product Research, 28(22), 1941–1951. http://doi.org/10.1080/14786419.2014.919286