Diterpenes from Zuelania guidonia

n-hexane, chloroform and ethyl acetate respectively. Each concentrated fraction was subjected to TLC followed by isolation, purification and identification of the available constituents. Fourteen compounds were isolated and identified by different spectral tools (UV, IR, 1 H-NMR, 13 C-NMR, MS) and comparison with corresponding literature data. -amyrin (1), -amyrin (2), and a mixture of -sitosterol and stigmasterol (3) were isolated from nhexane fraction of both leaves and stem bark. 2-Oxo-18benzolyloxy-13(16), 14-tetrahydrocleroda-3-ene (4), 3--acetoxy-D:A friedo oleanan-27,16-lactone (5), 4,4'-dihydroxychalcone (6), apigenin (7) and kampferol (8) were isolated from chloroform fraction of the stem bark. -Sitosterol-3-O--D-glucoside (9), 5-Ocaffeoylquinic acid (10) were isolated from the ethyl acetate fraction of the leaves in addition to vanillin (11), benzoic acid (12), protocatechuic acid (13) and flacourtin (14) from the ethyl acetate fraction of the stem bark. The different leaf extracts were subjected to biological study which revealed that n-hexane, ethyl acetate and methanol fractions of Flacourtia cataphracta Roxb. are safe to be used as antidiarrheal, anti-inflammatory and antipyretic drug. leaves, stem and stem bark of the titled plant. 23 EXPERIMENTAL General experimental procedures 1-Melting points are uncorrected and measured by Koffler hot stage microscope type (ESP, Boctius M). 2-UV spectra were measured in methanol and different ionizing and complexing agents using UVidec-320 spectrophotometer (JAS CO, Japan). 3-Schimadzu infra red-470 spectrophotometer (Japan) was used for measuring IR spectra as KBr discs. 4-1 H-NMR and 13 C-NMR were recorded on JEOL TNM-LA 400 and 500 spectrophotometers using TMS as an internal standard. 5-Column chromatography was performed with silica gel 60 (E-Merck), Develosil Lop ODS (30-50 µ, Nomura Chemicals). 6-Silica gel 60 G F 254 and precoated aluminium sheets to silica gel 60 G F 254 (E-Merck) were used for TLC purposes. 7-The spots were visualized by UV lamp (254, 366 nm, VL, 6LC, Marinc Lavalec-Codex, France) and sprayed with 10% H 2 SO 4 , 5% AlCl 3 or FeCl 3. 8-Authentic samples were obtained from Department of Pharmacognosy, Faculty of Pharmacy, Assiut University. 9-Solvent systems: In -Hexane-EtOAc (9 : 1). II-CHCl 3-MeOH (9.5 : 0.5).

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“…Column chromatographic fractionation of the EtOAc fraction of s.b, provided four compounds (11)(12)(13)(14).…”

mentioning

confidence: 99%

Phytochemical and Biological Investigations of Flacourtia Cataphracta Roxb. Cultivated in Egypt

Sayed

Mohamed

Darwish

et al. 2006

Bulletin of Pharmaceutical Sciences. Assiut

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“…Além disso, os valores de J = 3,0 e 14,0 Hz para  Outras 4 substâncias foram identificadas como diterpenos clerodânicos. As substâncias 5 e 6, obtidas em mistura, e 7 já haviam sido isoladas de Zuelania guidonia (KHAN et al, 1990b;KHAN, GRAY e WATERMAN, 1990), e a substância 9 havia sido relatada como produto semi-sintético (KHAN, GRAY e WATERMAN, 1990 A identificação estrutural foi realizada de maneira muito semelhante ao discutido para a caseobliquina A, confirmando as sub-estruturas referentes ao anel decalínico (A e B, C-1 a C-10), à cadeia lateral em C-9 e ao anel diacetálico (C). A determinação da configuração relativa destas substâncias também foi realizada considerando-se os mesmos aspectos discutidos para a caseobliquina A. Hz; H-12) que pôde ser atribuído ao hidrogênio da outra ligação dupla do dieno conjugado, dos componentes minoritário e majoritário, respectivamente.…”

Section: Casearia Obliqua Sprengelunclassified

“…Este grupamento está ligado ao C-2 em 5 e ao C-6 em 6, fato este evidenciado pela comparação com dados da literatura (KHAN et al, 1990b) …”

Section: Casearia Obliqua Sprengelunclassified

“…anéis A e B do sistema decalínico foi deduzida a partir do valor de  26,4 observado para a metila em C-20, conforme descrito na literatura (KHAN et al, 1990b;194 VIJAYAKUMAR et al, 2002). O deslocamento químico de C-5 ( 54,3) foi semelhante aos descritos para diterpenos clerodânicos e compostos análogos (ITOKAWA et al, 1990;MORITA et al, 1991;SHEN et al, 2004a) A substância 14 foi submetida a reação de acetilação, resultando em um novo diterpeno clerodânico denominado casearupestrina E (14a …”

Section: Casearia Obliqua Sprengelunclassified

“…Diterpenos clerodânicos semelhantes aos encontrados em Casearia foram isolados de outras espécies de Salicaceae, incluindo Zuelania guidonia (KHAN et al, 1990a;KHAN et al, 1990b), Laetia procera (GIBBONS et al, 1996;JULLIAN et al, 2005) e L. corymbulosa (BEUTLER et al, 2000a (KHAN et al, 1990a). 19,20-cleroda-3,13(16) …”

Section: Introductionunclassified

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Contribuição ao estudo dos metabólitos secundários do gênero Casearia e de algumas de suas atividades biológicas

Júnior¹,

Magela²

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CONTRIBUIÇÃO AO ESTUDO DOS METABÓLITOS SECUNDÁRIOS DO GÊNERO Casearia E DE ALGUMAS DE SUAS ATIVIDADES BIOLÓGICAS Bolsista de Mestrado -CNPq (2005-CNPq ( -2007 Título do projeto: "Estudo químico e atividades citotóxica e antioxidante de Dipteryx lacunifera Ducke (Leguminosae-Papilionoideae)". -FAPESP (2007-FAPESP ( -2010 gossypiosperma resulting in the isolation of the (+)-taxifolin (1), isolated from both extracts, showed 76% of inhibition of the acetylcholinesterase enzyme. The Bolsista de Doutorado

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Casearin X, Its Degradation Product and Other Clerodane Diterpenes from Leaves of Casearia sylvestris: Evaluation of Cytotoxicity against Normal and Tumor Human Cells

Santos

Ferreira

Júnior

et al. 2010

Chemistry & Biodiversity

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An EtOH extract of the leaves of Casearia sylvestris afforded new clerodane diterpene, casearin X, together with the known compounds casearins B, D, L, and O, and caseargrewiin F. Casearin X degraded to the corresponding dialdehyde when stored in CDCl(3). The diterpenes isolated were cytotoxic to human cancer cell lines, with caseargrewiin F being the most active and the new clerodane, casearin X, the second active compound with IC(50) values comparable to the positive control doxorubicin. All isolated diterpenes showed lower activities against normal human cells than against cancer cell lines, which might indicate a possible selective action on cancer cells. Casearin X dialdehyde was not cytotoxic to cancer cells indicating that the occurrence of these CO groups at C(18) and C(19) is incompatible with the cytotoxic activity.

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Diterpenes from Zuelania guidonia

Cited by 25 publications

References 3 publications

Phytochemical and Biological Investigations of Flacourtia Cataphracta Roxb. Cultivated in Egypt

Phytochemical and Biological Investigations of Flacourtia Cataphracta Roxb. Cultivated in Egypt

Contribuição ao estudo dos metabólitos secundários do gênero Casearia e de algumas de suas atividades biológicas

Casearin X, Its Degradation Product and Other Clerodane Diterpenes from Leaves of Casearia sylvestris: Evaluation of Cytotoxicity against Normal and Tumor Human Cells

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