Derivados citotóxicos de vitanolidos isolados das folhas de Acnistus arborescens

Minguzzi, Sandro; Barata, Lauro Euclides Soares; Cordell, Geoffrey A.

doi:10.1590/s0100-40422011000200013

Cited by 8 publications

(4 citation statements)

References 15 publications

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“…16-OAc group: 7β,16α-Diacetoxywithanolide D 40 is slightly less potent than 7β-acetoxywithanolide D 41 [32,37].…”

Section: -Oac Groupmentioning

confidence: 97%

Antiproliferative withanolides from the solanaceae: A structure-activity study

Zhang¹,

Samadi²,

Gallagher³

et al. 2012

Planta Med

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As part of our search for bioactive compounds from plant biodiversity, 29 withanolides were recently isolated from three members of the Solanaceae: Physalis longifolia, Vassobia breviflora, and Withania somnifera. Six derivatives were prepared from these naturally occurring withanolides. All compounds were evaluated for in vitro antiproliferative 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 IC 50 values in the range of 0.067−17.4 μM, including withaferin A, withaferin A 4,27-diacetate, 27-O-glucopyranosylwithaferin A, withalongolide H, withalongolide C, withalongolide A, withalongolide A 4,27-diacetate, withalongolide A 4,19,27-triacetate, withalongolide B, withalongolide B 4-acetate, withalongolide B 4,19-diacetate, withalongolide D, withalongolide E, withalongolide G, and 2,3-dihydrowithaferin A 3-O-sulfate. In order to update the growing literature on withanolides and their activities, we summarized the distribution, structural types, and antiproliferative activities for all published withanolides to date. The structure-activity relationship analysis (SARA) confirmed the importance of the presence of a Δ 2 -1-oxo-functionality in ring A, a 5β,6β-epoxy or 5α-chloro-6β-hydroxy grouping 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, and 28 were not contributors to the observed antiproliferative activity within the systems analyzed.

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“…16-OAc group: 7β,16α-Diacetoxywithanolide D 40 is slightly less potent than 7β-acetoxywithanolide D 41 [32,37].…”

Section: -Oac Groupmentioning

confidence: 97%

Antiproliferative withanolides from the solanaceae: A structure-activity study

Zhang¹,

Samadi²,

Gallagher³

et al. 2012

Planta Med

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“…The biological effects of 7 β-acetoxywithanolide D include anticancer and cytotoxic activities (MINGUZZI et al, 2002(MINGUZZI et al, , 2011, with ED 50 values ranging from 0.03 and 1.3 mg ml -1 for human breast cancer, human lung cancer, human colon cancer, human oral epidermoid carcinoma, vinblastine-resistant KB cell line and hormone-dependent human prostate cancer.…”

mentioning

confidence: 99%

Biological activity of 7beta-acetoxywithanolide D isolated from Acnistus arborescens

Corrêa

Fortkamp

Silva

et al. 2018

SCA

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Many oomycete species are plant pathogens and are responsible for causing significant losses in agriculture. Currently, plant pathogen control is carried out by chemical, biological and physical methods. However, due to the development of resistance to these methods by some pathogens, it is imperative that alternative methods are developed. Brazilian biodiversity is well-known for its species richness and is considered a promising source of natural products. Among the vascular plants, the family Solanaceae A. Juss. (Solanaceae) is considered one of the largest, with distributions across all tropical and temperate regions of the world. The Solanaceae family presents a high diversity of species of economic importance as sources of food, medicinal and ornamental properties. Plants of this family are sources of secondary metabolites of various chemical classes that possess potential diverse applications. Therefore, chemical and biological investigations of these compounds are extremely important as they present alternatives for their potential use in the control of plant pathogens. Here, we report for the first time, the biological activity of 7beta-acetoxywithanolide D, a compound isolated from Acnistus arborescens, against the oomycete Phytophthora cinnamomi. With these results, we emphasize the importance of such studies on plant secondary metabolites, which may present coadjuvant options in the control of plant pathogens.

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“…Estes foram avaliados quanto à citotoxicidade nas células de adenocarcinoma de colon (DLD-1). Os As maiorias das pesquisas realizadas com os compostos pertencentes à classe dos vitanolidos avaliam a atividades anticancerígenas (MISICO et al, 2002;VERAS et al, 2004;MORANTES et al, 2006;CORDELL, 2011;ZHANG, et al, 2012;ALALI et al, 2014…”

Section: Resultados E Discussõesunclassified

Estudo químico de extratos de plantas da família Solanaceae com atividade a fungos fitopatogênicos

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Derivados citotóxicos de vitanolidos isolados das folhas de Acnistus arborescens

Cited by 8 publications

References 15 publications

Antiproliferative withanolides from the solanaceae: A structure-activity study

Antiproliferative withanolides from the solanaceae: A structure-activity study

Biological activity of 7beta-acetoxywithanolide D isolated from Acnistus arborescens

Estudo químico de extratos de plantas da família Solanaceae com atividade a fungos fitopatogênicos

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