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Minor Withanolides of Physalis longifolia: Structure and Cytotoxicity
dc.contributor.author | Zhang, Huaping | |
dc.contributor.author | Motiwala, Hashim F. | |
dc.contributor.author | Samadi, Abbas K. | |
dc.contributor.author | Day, Victor W. | |
dc.contributor.author | Aubé, Jeffrey | |
dc.contributor.author | Cohen, Mark S. | |
dc.contributor.author | Kindscher, Kelly | |
dc.contributor.author | Gollapudi, Rao | |
dc.contributor.author | Timmermann, Barbara N. | |
dc.date.accessioned | 2015-03-04T21:38:20Z | |
dc.date.available | 2015-03-04T21:38:20Z | |
dc.date.issued | 2012-01-01 | |
dc.identifier.citation | Zhang, Huaping et al. (2012). "Minor Withanolides of Physalis longifolia: Structure and Cytotoxicity." Chemical and Pharmaceutical Bulletin, 60(10):1234-39. http://dx.doi.org/10.1248/cpb.c12-00305. | en_US |
dc.identifier.issn | 0009-2363 | |
dc.identifier.uri | http://hdl.handle.net/1808/16968 | |
dc.description | This is the publisher's version, also available electronically from https://www.jstage.jst.go.jp/article/cpb/60/10/60_c12-00305/_article. | en_US |
dc.description.abstract | In our recent publication on bioactive guided isolation of compounds from Physalis longifolia (Solanaceae) novel anti-proliferative agents withalongolides A (4) and B (5), and their highly cytotoxic analogues, withalongolide A 4,19,27-triacetate (4a) and withalongolide B 4,19-diacetate (5a) were elucidated. In this study, the two lead compounds (4, 5) were re-isolated in gram quantities for the purpose of further analogue preparation and in vivo testing that would continue to probe structure–activity relationships. During this process, two additional withanolides, named withalongolides O (1) and P (2), were elucidated. Their structures were determined by spectroscopic techniques with 1 being subsequently confirmed by X-ray crystallographic analysis. Utilizing a MTS [3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium] viability assay, withalongolide O (1) and its 4,7-diaceatate (1a), both containing the functionalities of Δ2-1-oxo- in A ring, a 5β,6β-epoxy in B ring, and a lactone ring in the nine-carbon side chain, exhibited potent cytotoxicity against human head and neck squamous cell carcinoma (JMAR and MDA-1986), melanoma (B16F10 and SKMEL-28), and normal fetal lung fibroblast (MRC-5) cells with IC50 values in the range between 0.15 and 2.95 µM. In addition, the previously reported α orientation of 7-acetate group in acnistins C and D should be revised to the β orientation on the basis of NMR data comparison. | en_US |
dc.publisher | Pharmaceutical Society of Japan | en_US |
dc.title | Minor Withanolides of Physalis longifolia: Structure and Cytotoxicity | en_US |
dc.type | Article | |
kusw.kuauthor | Kindscher, Kelly | |
kusw.kudepartment | Environmental Studies Program | en_US |
dc.identifier.doi | 10.1248/cpb.c12-00305 | |
dc.identifier.orcid | https://orcid.org/0000-0003-1049-5767 | |
kusw.oaversion | Scholarly/refereed, publisher version | |
kusw.oapolicy | This item meets KU Open Access policy criteria. | |
dc.rights.accessrights | openAccess |