@article{zhang_anti-proliferative_2012,
	title = {Anti-proliferative withanolides from the {Solanaceae}: a structure-activity study},
	volume = {84},
	issn = {0033-4545},
	shorttitle = {Anti-proliferative withanolides from the {Solanaceae}},
	doi = {10.1351/PAC-CON-11-10-08},
	abstract = {As part of our search for bioactive compounds from plant biodiversity, 29 withanolides (1, 3-6, 9, 12-18, and 20-35) were recently isolated from three members of the Solanaceae: Physalis longifolia, Vassobia breviflora, and Withania somnifera. Six derivatives (2, 7, 8, 10, 11, and 19) were prepared from these naturally occurring withanolides. All compounds (1-35) were evaluated for in vitro anti-proliferative activity against an array of cell lines [melanoma cell lines (B16F10, SKMEL28); human head and neck squamous cell carcinomas (HNSCC) cell lines (JMAR, MDA1986, DR081-1); breast cancer cell line (Hs578T), and non-malignant human cell line (MRC5)]. This led to the discovery of 15 withanolides, with IC50 values in the range of 0.067-17.4 µM, including withaferin A 1, withaferin A 4,27-diacetate 2, 27-O-glucopyranosylwithaferin A 3, withalongolide H 4, withalongolide C 5, withalongolide A 6, withalongolide A 4,27-diacetate 7, withalongolide A 4,19,27-triacetate 8, withalongolide B 9, withalongolide B 4-acetate 10, withalongolide B 4,19-diacetate 11, withalongolide D 16, withalongolide E 17, withalongolide G 21, and 2,3-dihydrowithaferin A 3-O-sulfate 22). In order to update the growing literature on withanolides and their activities, we summarized the distribution, structural types and anti-proliferative activities for all published withanolides to date. The structure-activity relationship analysis (SARA) confirmed the importance of the presence of a Δ2-1-oxo- functionality in ring A, a 5β,6β-epoxy or 5α-chloro-6β-hydroxy groupings in ring B, and nine carbon side chain with a lactone moiety for cytotoxic activity. Conversely, the SARA indicated that the -OH or -OR groups at C-4, 7, 11, 12, 14, 15, 16, 17, 18, 19, 20, 23, 24, 27, 28 were not contributors to the observed anti-proliferative activity within the systems analyzed.},
	language = {eng},
	number = {6},
	journal = {Pure and Applied Chemistry. Chimie Pure Et Appliquee},
	author = {Zhang, Huaping and Samadi, Abbas K. and Cohen, Mark S. and Timmermann, Barbara N.},
	year = {2012},
	pmid = {24098060},
	pmcid = {PMC3789375},
	keywords = {Physalis longifolia, Solanaceae, Vassobia breviflora, Withania somnifera, anti-proliferative, structure classifcation, structure-activity relationship, withanolide},
	pages = {1353--1367},
}

{"_id":"F5p3k2grWDW4rGQcm","bibbaseid":"zhang-samadi-cohen-timmermann-antiproliferativewithanolidesfromthesolanaceaeastructureactivitystudy-2012","author_short":["Zhang, H.","Samadi, A. K.","Cohen, M. S.","Timmermann, B. N."],"bibdata":{"bibtype":"article","type":"article","title":"Anti-proliferative withanolides from the Solanaceae: a structure-activity study","volume":"84","issn":"0033-4545","shorttitle":"Anti-proliferative withanolides from the Solanaceae","doi":"10.1351/PAC-CON-11-10-08","abstract":"As part of our search for bioactive compounds from plant biodiversity, 29 withanolides (1, 3-6, 9, 12-18, and 20-35) were recently isolated from three members of the Solanaceae: Physalis longifolia, Vassobia breviflora, and Withania somnifera. Six derivatives (2, 7, 8, 10, 11, and 19) were prepared from these naturally occurring withanolides. All compounds (1-35) were evaluated for in vitro anti-proliferative activity against an array of cell lines [melanoma cell lines (B16F10, SKMEL28); human head and neck squamous cell carcinomas (HNSCC) cell lines (JMAR, MDA1986, DR081-1); breast cancer cell line (Hs578T), and non-malignant human cell line (MRC5)]. This led to the discovery of 15 withanolides, with IC50 values in the range of 0.067-17.4 µM, including withaferin A 1, withaferin A 4,27-diacetate 2, 27-O-glucopyranosylwithaferin A 3, withalongolide H 4, withalongolide C 5, withalongolide A 6, withalongolide A 4,27-diacetate 7, withalongolide A 4,19,27-triacetate 8, withalongolide B 9, withalongolide B 4-acetate 10, withalongolide B 4,19-diacetate 11, withalongolide D 16, withalongolide E 17, withalongolide G 21, and 2,3-dihydrowithaferin A 3-O-sulfate 22). In order to update the growing literature on withanolides and their activities, we summarized the distribution, structural types and anti-proliferative activities for all published withanolides to date. The structure-activity relationship analysis (SARA) confirmed the importance of the presence of a Δ2-1-oxo- functionality in ring A, a 5β,6β-epoxy or 5α-chloro-6β-hydroxy groupings in ring B, and nine carbon side chain with a lactone moiety for cytotoxic activity. Conversely, the SARA indicated that the -OH or -OR groups at C-4, 7, 11, 12, 14, 15, 16, 17, 18, 19, 20, 23, 24, 27, 28 were not contributors to the observed anti-proliferative activity within the systems analyzed.","language":"eng","number":"6","journal":"Pure and Applied Chemistry. Chimie Pure Et Appliquee","author":[{"propositions":[],"lastnames":["Zhang"],"firstnames":["Huaping"],"suffixes":[]},{"propositions":[],"lastnames":["Samadi"],"firstnames":["Abbas","K."],"suffixes":[]},{"propositions":[],"lastnames":["Cohen"],"firstnames":["Mark","S."],"suffixes":[]},{"propositions":[],"lastnames":["Timmermann"],"firstnames":["Barbara","N."],"suffixes":[]}],"year":"2012","pmid":"24098060","pmcid":"PMC3789375","keywords":"Physalis longifolia, Solanaceae, Vassobia breviflora, Withania somnifera, anti-proliferative, structure classifcation, structure-activity relationship, withanolide","pages":"1353–1367","bibtex":"@article{zhang_anti-proliferative_2012,\n\ttitle = {Anti-proliferative withanolides from the {Solanaceae}: a structure-activity study},\n\tvolume = {84},\n\tissn = {0033-4545},\n\tshorttitle = {Anti-proliferative withanolides from the {Solanaceae}},\n\tdoi = {10.1351/PAC-CON-11-10-08},\n\tabstract = {As part of our search for bioactive compounds from plant biodiversity, 29 withanolides (1, 3-6, 9, 12-18, and 20-35) were recently isolated from three members of the Solanaceae: Physalis longifolia, Vassobia breviflora, and Withania somnifera. Six derivatives (2, 7, 8, 10, 11, and 19) were prepared from these naturally occurring withanolides. All compounds (1-35) were evaluated for in vitro anti-proliferative activity against an array of cell lines [melanoma cell lines (B16F10, SKMEL28); human head and neck squamous cell carcinomas (HNSCC) cell lines (JMAR, MDA1986, DR081-1); breast cancer cell line (Hs578T), and non-malignant human cell line (MRC5)]. This led to the discovery of 15 withanolides, with IC50 values in the range of 0.067-17.4 µM, including withaferin A 1, withaferin A 4,27-diacetate 2, 27-O-glucopyranosylwithaferin A 3, withalongolide H 4, withalongolide C 5, withalongolide A 6, withalongolide A 4,27-diacetate 7, withalongolide A 4,19,27-triacetate 8, withalongolide B 9, withalongolide B 4-acetate 10, withalongolide B 4,19-diacetate 11, withalongolide D 16, withalongolide E 17, withalongolide G 21, and 2,3-dihydrowithaferin A 3-O-sulfate 22). In order to update the growing literature on withanolides and their activities, we summarized the distribution, structural types and anti-proliferative activities for all published withanolides to date. The structure-activity relationship analysis (SARA) confirmed the importance of the presence of a Δ2-1-oxo- functionality in ring A, a 5β,6β-epoxy or 5α-chloro-6β-hydroxy groupings in ring B, and nine carbon side chain with a lactone moiety for cytotoxic activity. Conversely, the SARA indicated that the -OH or -OR groups at C-4, 7, 11, 12, 14, 15, 16, 17, 18, 19, 20, 23, 24, 27, 28 were not contributors to the observed anti-proliferative activity within the systems analyzed.},\n\tlanguage = {eng},\n\tnumber = {6},\n\tjournal = {Pure and Applied Chemistry. 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N."],"key":"zhang_anti-proliferative_2012","id":"zhang_anti-proliferative_2012","bibbaseid":"zhang-samadi-cohen-timmermann-antiproliferativewithanolidesfromthesolanaceaeastructureactivitystudy-2012","role":"author","urls":{},"keyword":["Physalis longifolia","Solanaceae","Vassobia breviflora","Withania somnifera","anti-proliferative","structure classifcation","structure-activity relationship","withanolide"],"metadata":{"authorlinks":{}}},"bibtype":"article","biburl":"https://api.zotero.org/users/585595/collections/AHTPD767/items?key=KhA4GoMeOvxPn5tlpemkMrP3&format=bibtex&limit=100","dataSources":["DfcenonoS4CcJtLNQ","mLRCv4BM3hCZt8ZRw"],"keywords":["physalis longifolia","solanaceae","vassobia breviflora","withania somnifera","anti-proliferative","structure classifcation","structure-activity relationship","withanolide"],"search_terms":["anti","proliferative","withanolides","solanaceae","structure","activity","study","zhang","samadi","cohen","timmermann"],"title":"Anti-proliferative withanolides from the Solanaceae: a structure-activity study","year":2012}