Arid
DOI10.1016/j.bmc.2008.10.091
2,3-Dihydrowithaferin A-3 beta-O-sulfate, a new potential prodrug of withaferin A from aeroponically grown Withania somnifera
Xu, Ya-ming1; Marron, Marilyn T.1; Seddon, Emily1; McLaughlin, Steven P.1; Ray, Dennis T.2; Whitesell, Luke3; Gunatilaka, A. A. Leslie1,4
通讯作者Gunatilaka, A. A. Leslie
来源期刊BIOORGANIC & MEDICINAL CHEMISTRY
ISSN0968-0896
EISSN1464-3391
出版年2009
卷号17期号:6页码:2210-2214
英文摘要

Preparations of the roots of the medicinal plant Withania somnifera (L.) Dunal commonly called ashwagandha have been used for millennia in the Ayurvedic medical tradition of India as a general tonic to relieve stress and enhance health, especially in the elderly. In modern times, ashwagandha has been shown to possess intriguing antiangiogenic and anticancer activity, largely attributable to the presence of the steroidal lactone withaferin A as the major constituent. When cultured using the aeroponic technique, however, this plant was found to produce a new natural product, 2,3-dihydrowithaferin A-3 beta-O-sulfate (1), as the predominant constituent of methanolic extracts prepared from aerial tissues. The characteristic bioactivities exhibited by 1 including inhibition of cancer cell proliferation/survival, disruption of cytoskeletal organization and induction of the cellular heat-shock response paralleled those displayed by withaferin A (2). The delayed onset of action and reduced potency of 1 in cell culture along with previous observations demonstrating the requirement of the 2(3)-double bond in withanolides for bioactivity suggested that 1 might be converted to 2 in cell culture media and this was confirmed by HPLC analysis. The abundant yield of 1 from aeroponically cultivated plants, its good aqueous solubility and spontaneous conversion to 2 under cell culture conditions, suggest that 1 could prove useful as a readily formulated prodrug of withaferin A that merits further evaluation in animal models. (C) 2008 Elsevier Ltd. All rights reserved.


英文关键词Aeroponic culture 2,3-Dihydrowithaferin A-3 beta-O-sulfate Prodrug Anticancer activity Cytoskeletal reorganization Heat-shock induction
类型Article
语种英语
国家USA
收录类别SCI-E
WOS记录号WOS:000264236700014
WOS关键词COMPOUND WITHAFERIN ; STEROIDAL LACTONES ; TUMOR INHIBITOR ; SONORAN-DESERT ; IN-VIVO ; ASHWAGANDHA ; CELLS ; APOPTOSIS ; WITHANOLIDES ; FACTOR-1
WOS类目Biochemistry & Molecular Biology ; Chemistry, Medicinal ; Chemistry, Organic
WOS研究方向Biochemistry & Molecular Biology ; Pharmacology & Pharmacy ; Chemistry
来源机构University of Arizona
资源类型期刊论文
条目标识符http://119.78.100.177/qdio/handle/2XILL650/160034
作者单位1.Univ Arizona, SW Ctr Nat Prod Res & Commercializat, Off Arid Lands Studies, Coll Agr & Life Sci, Tucson, AZ 85706 USA;
2.Univ Arizona, Dept Plant Sci, Coll Agr & Life Sci, Tucson, AZ 85721 USA;
3.Whitehead Inst, Cambridge, MA 02142 USA;
4.Univ Arizona, Inst BIO5, Tucson, AZ 85721 USA
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Xu, Ya-ming,Marron, Marilyn T.,Seddon, Emily,et al. 2,3-Dihydrowithaferin A-3 beta-O-sulfate, a new potential prodrug of withaferin A from aeroponically grown Withania somnifera[J]. University of Arizona,2009,17(6):2210-2214.
APA Xu, Ya-ming.,Marron, Marilyn T..,Seddon, Emily.,McLaughlin, Steven P..,Ray, Dennis T..,...&Gunatilaka, A. A. Leslie.(2009).2,3-Dihydrowithaferin A-3 beta-O-sulfate, a new potential prodrug of withaferin A from aeroponically grown Withania somnifera.BIOORGANIC & MEDICINAL CHEMISTRY,17(6),2210-2214.
MLA Xu, Ya-ming,et al."2,3-Dihydrowithaferin A-3 beta-O-sulfate, a new potential prodrug of withaferin A from aeroponically grown Withania somnifera".BIOORGANIC & MEDICINAL CHEMISTRY 17.6(2009):2210-2214.
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