Antiproliferative withanolides from several solanaceous species
| Autor: | Robert J. Gallagher, Huaping Zhang, Barbara N. Timmermann, Cong-Mei Cao |
|---|---|
| Rok vydání: | 2014 |
| Předmět: |
Molecular Structure
biology Stereochemistry Organic Chemistry Datura wrightii Plant Science Withania somnifera biology.organism_classification Antineoplastic Agents Phytogenic Biochemistry Article Analytical Chemistry Structure-Activity Relationship chemistry.chemical_compound Withanolide chemistry Physalis Physalis longifolia Structure–activity relationship Drug Screening Assays Antitumor Cytotoxicity Nuclear Magnetic Resonance Biomolecular Withanolides Solanaceae |
| Zdroj: | Natural Product Research. 28:1941-1951 |
| ISSN: | 1478-6427 1478-6419 |
| DOI: | 10.1080/14786419.2014.919286 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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