Xylodiol, a New Atisane Diterpenoid from Xylopia Langsdorffiana St.‐Hil. &amp; Tul. (Annonaceae)

Tavares, Josean Fechine; Silva, Marianna Vieira B.; Queiroga, Karine F.; Diniz, Margareth F. F. Melo; Barbosa-Filho, José Maria; Haun, Marcela; Melo, Patrícia S.; Silva, Marcelo Sobral da

doi:10.1002/chin.200737172

Cited by 3 publications

(5 citation statements)

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“…Xylodiol (1) was obtained from Xylopia langsdorfiana St.Hilaire & Tulasne, Annonaceae, leaves as previously described (Tavares et al, 2007).…”

Section: Drugmentioning

confidence: 99%

“…We have previously reported that xylodiol inhibits cell growth and induces differentiation in human leukemia cell lines (HL60, U937 and K562) (Castello-Branco et al, 2009). Moreover, xylodiol showed weak cytotoxicity against V79 cells and rat hepatocytes (Tavares et al, 2007).…”

Section: Introductionmentioning

confidence: 96%

“…Xylodiol (1), an atisane diterpene, was isolated from Xylopia langsdorfiana St.Hilaire & Tulasne, Annonaceae, leaves and characterized as ent-atisan-7α,16α-diol (Tavares et al, 2007). Atisane diterpenes are rare in the Annonaceae family, having been recorded only in Xylopia aromatica (Morais & Roque, 1988).…”

Section: Introductionmentioning

confidence: 99%

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Xylodiol from Xylopia langsdorfiana induces apoptosis in HL60 cells

Castello-Branco¹,

Tavares²,

Silva³

et al. 2011

Rev. bras. farmacogn.

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An atisane diterpene was isolated from Xylopia langsdorfi ana St. Hilaire & Tulasne, Annonaceae, leaves,. Preliminary study showed that xylodiol was cytotoxic and induced differentiation on human leukemia cell lines. However, the molecular mechanisms of xylodiol-mediated cytotoxicity have not been fully defined. Thus, we investigated the anti-tumor effect of xylodiol in human leukemia HL60 cell line. Xylodiol induced apoptosis and necrosis. HL60 cells treated with xylodiol showed biochemical changes characteristic of apoptosis, including caspases-8, -9 and -3 activation and loss of mitochondrial transmembrane potential (∆ψ m ). However, there was a condensation rather than swelling of mitochondria. Moreover, the formation of condensed mitochondria and the loss of ∆ψ m occurred downstream of caspase activation. Cyclosporine A did not protect HL60 cells from the cytotoxic effects of xylodiol, suggesting that the loss of ∆ψ m is a late event in xylodiol-induced apoptosis. Oxidative stress was involved in xylodiol-induced apoptosis. Thus, we conclude that activated caspases cleave cellular proteins resulting in mitochondrial damage leading to mitochondrial condensation, loss of ∆ψ m and ROS release from the mitochondria. ROS can further induce and maintain a collapse of ∆ψ m leading to cellular damage through oxidation of lipids and proteins resulting in apoptotic cell death.

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“…Xylodiol (1) was obtained from Xylopia langsdorfiana St.Hilaire & Tulasne, Annonaceae, leaves as previously described (Tavares et al, 2007).…”

Section: Drugmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 96%

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Xylodiol from Xylopia langsdorfiana induces apoptosis in HL60 cells

Castello-Branco¹,

Tavares²,

Silva³

et al. 2011

Rev. bras. farmacogn.

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“…& Tul. (Tavares et al, 2007), apresenta efeito relaxante em traquéia isolada de cobaia por um mecanismo aparentemente independente de fatores relaxantes derivados do epitélio, porém dependente da ativação de canais de K + . O tônus miogênico das vias aéreas é mantido devido ao infl uxo passivo de íons Ca 2+ através de vários canais de membrana, que proporciona uma quantidade sufi ciente para manter os níveis basais de Ca 2+ intracelulares e a quantidade desse íon armazenada no retículo sarcoplasmático, assim como esse infl uxo ajuda a manter o potencial de membrana dessas células (Montano;Bazan-Perkins, 2005).…”

Section: Discussionunclassified

“…A partir do extrato etanólico bruto, obtido das cascas do caule dessa espécie, também foi isolado um diterpeno tipo labdano, sendo este identifi cado por comparação de seus dados de ponto de fusão (139-141 °C), espectroscopia de ressonância nuclear magnética de hidrogênio e carbono (RMN de 1 H e 13 C) com dados previamente publicados por Bohlmann et al (1980), como sendo o ácido 8(17),12E,14-labdatrieno-18-óico (Figura 1), com fórmula molecular C 20 H 30 O 2 e massa molecular de 302,451 u.m.a. (Tavares et al, 2007), neste trabalho codifi cado por labdano302.…”

Section: Introductionunclassified

O Ácido (8)17,12E,14-labdatrieno-18-óico (labdano302), diterpeno tipo labdano isolado de Xylopia langsdorffiana St. Hil. & Tul. (Annonaceae) relaxa a traquéia isolada de cobaia

Ribeiro¹,

Tavares²,

Andrade³

et al. 2007

Rev. bras. farmacogn.

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Azaphenanthrene Alkaloids with Antitumoral Activity from Anaxagorea dolichocarpa Sprague & Sandwith (Annonaceae)

et al. 2011

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Phytochemical investigation of Anaxagorea dolichocarpa Sprague & Sandwith led to isolation of three azaphenanthrene alkaloids: eupolauramine, sampangine and imbiline 1. Their chemical structures were established on the basis of spectroscopic data from IR, HR-ESI-MS, NMR (including 2D experiments) and comparison with the literature. Sampangine and imbiline 1 are being described in the Anaxagorea genus for the first time. Eupolauramine and sampangine show concentration-dependent antitumoral activity in leukemic cells K562 with IC50 of 18.97 and 10.95 µg/mL, respectively.

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Xylodiol, a New Atisane Diterpenoid from Xylopia Langsdorffiana St.‐Hil. & Tul. (Annonaceae)

Cited by 3 publications

References 1 publication

Xylodiol from Xylopia langsdorfiana induces apoptosis in HL60 cells

Xylodiol from Xylopia langsdorfiana induces apoptosis in HL60 cells

O Ácido (8)17,12E,14-labdatrieno-18-óico (labdano302), diterpeno tipo labdano isolado de Xylopia langsdorffiana St. Hil. & Tul. (Annonaceae) relaxa a traquéia isolada de cobaia

Azaphenanthrene Alkaloids with Antitumoral Activity from Anaxagorea dolichocarpa Sprague & Sandwith (Annonaceae)

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