Prunin-6″-O-p-coumarate, a new acylated flavanone glycoside from Anacardium occidentale

Rahman, W.; Ishratullah, Khwaja; Wagner, Hildebert; Seligmann, Otto; Chari, V. M.; Österdahl, Bengt‐Göran

doi:10.1016/s0031-9422(00)94284-5

Cited by 30 publications

(10 citation statements)

References 4 publications

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“…HMBC correlation was found between the anomeric proton (d H 4.95) and the d C 165.8 (C-7). Compound 3 was identified as naringenin-7-O-glucopyranoside which was consistent with published data (Rahman et al 1978) ( Figure S3). …”

supporting

confidence: 90%

Two new dihydroamentoflavone glycosides fromCycas revoluta

Moawad

Hetta

Zjawiony

et al. 2013

Natural Product Research

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Phytochemical investigation of the ethyl acetate extract of Cycas revoluta Thunb. leaflets afforded five compounds including two new dihydroamentoflavone glucosides, (2S)-I-(2,3)-dihydro-I-7-O-β-D-glucopyranosylamentoflavone (1) and (2S)-I-(2,3)-dihydro-I-7,II-7-di-O-β-D-glucopyranosylamentoflavone (2), in addition to the known compounds prunin (3), vitexin-2″-rhamnoside (4) and protocatechuic acid (5). Compounds (3) and (4) being reported for the first time in this plant. The structures of these compounds were established by the detailed analysis of their spectroscopic data, mainly 1D NMR, 2D NMR, CD and HR-MSD-TOF. The ethyl acetate extract showed weak cytotoxicity against HepG2 (IC50 = 207.6 μg/mL) and RAW 264.2 cells (IC50 = 160.8 μg/mL). Compound 4 showed significant activity towards Leishmania donavani (IC50 = 13.8 μM, IC90 = 34.6 μM). The isolated compounds showed weak antimicrobial activity (IC50>10 μg/mL).

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supporting

confidence: 90%

Two new dihydroamentoflavone glycosides fromCycas revoluta

Moawad

Hetta

Zjawiony

et al. 2013

Natural Product Research

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“…The Et 2 O layer was partitioned between hexane and MeOH, and the MeOH layer was further chromatographed successively over Sephadex LH-20, silica gel, MCI-gel CHP 20P and Chromatorex ODS to afford 1 and 2, as well as 17 known compounds. The known ones were identified as naringenin, 6) eriodictyol, 6) kaempferol, 7) dihydrokaempferol, 8,9) quercetin, 7) naringenin 7-O-glucoside (prunin), 10) naringenin 7-O-(6Љ-O-galloyl)-glucoside, 10) naringenin 7-O-(6Љ-O-trans-p-coumaroyl)-glucoside, 11) kaempferol 3-O-rhamnoside, 7) quercetin 3-O-rhamnoside, 7) myricetin 3-O-rhamnoside, 7) 2-(2-methylbutyryl)-phloroglucinol 1-O-b-D-glucopyranoside (multifidol glucoside) (5), 12) (Ϫ)-epigallocatechin 3-O-gallate, 13) 1,2,3,6-tetra-O-, 14) 1,2,4,6-tetra-O-, 15) and 1,2,3,4,5-penta-O-galloyl-b-Dglucose, 16) and decarboxyellagic acid 17) by comparison of the physical and spectral data with literature values.…”

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confidence: 99%

Two New Acylated Flavanone Glycosides from the Leaves and Branches of Phyllanthus emblica.

et al. 2002

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Phyllanthus emblica L. (Euphorbiaceae) is a shrub or tree native to subtropical and tropical areas of China, India, Indonesia and the Malay Peninsula. The fruit has been widely used for antiinflammatory and antipyretic treatment. The root, leaves and bark are also used for the treatment of indigestion, diarrhea or dysentery, eczema and wart. As a continuation of investigation on the constituents of this plant,

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“…Além dos lipídios fenólicos destacam-se outros constituintes químicos isolados e identificados nas diversas partes do cajueiro como os flavonóides apigenina, kanferol, quercetina, quercetina-3-O-glicopiranosila, quercetina-3-O-ranminopiranosila, miricetina, agatisflavona, robustoflavona e amentoflavona nas folhas (Arya et al, 1989); naringenina, naringenina-7-O-(6''-O-p-cumaroil)-β-D-glicosila (Rahman et al, 1978), naringenina-5β-glicosila (Murthy et al, 1982) occidentosideo, também conhecido como (-)-salipurposideo (Murthy et al, 1981;Murthy et al, 1982) nas cascas da castanha; (+)-catequina e (-)-epicatequina no tegumento (Subrahmanian & Nair, 1969). Além destes foram isolados galato de etila das flores (Subrahmanian et al, 1969); sitosterol das cascas da castanha (Murthy et al, 1982); ácido gálico, como produto de hidrólise de taninos, myoinositol, colesterol, campesterol, estigmasterol e sitosterol das cascas do caule (Mota, 1982;Dinda et al, 1987).…”

Section: Introductionunclassified

Fenóis totais, atividade antioxidante e constituintes químicos de extratos de Anacardium occidentale L., Anacardiaceae

Chaves¹,

Lopes²,

Lopes³

et al. 2010

Rev. bras. farmacogn.

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RESUMO:O presente artigo relata o isolamento e identificação do palmitato, oleato e linoleato de sitosterila, sitosterol, estigmasterol, 3-O-β-D-galactopiranosídeo do sitosterol, 3-O-β-Dgalactopiranosídeo do estigmasterol, 3-O-β-D-glicopiranosídeo do sitosterol e uma mistura de ácidos anacárdicos (monoeno e dieno) do extrato etanólico de cascas do caule de Anacardium occidentale L., Anacardiaceae, bem como do sitosterol, estigmasterol, lupeol, β-amirina, catequina e epicatequina do extrato etanólico do tegumento da castanha de caju in natura. Os extratos EtOH da casca e do tegumento foram avaliados quanto ao conteúdo de fenóis totais e atividade antioxidante. O extrato etanólico das cascas do caule apresentou maior conteúdo de compostos fenólicos e percentual de atividade antioxidante.Unitermos: Anacardium occidentale, catequinas, esteroides, fenóis totais, atividade antioxidante. ABSTRACT: "Total phenolics, antioxidant activity and chemical constituents from extracts ofAnacardium occidentale L., Anacardiaceae". This paper describes the isolation and identification of a mixture of sitosteryl ester derivatives of fatty acids (palmitic, oleic and linoleic), sitosterol, stigmasterol, sitosterol-3-O-β-galactopyranoside, stigmasterol-3-O-β-galactopyranoside, sitosterol-3-O-β-glucopyranoside and a mixture of anacardic acids (monoene and diene) from stem bark of Anacardium occidentale L., Anacardiaceae, as well as sitosterol, stigmasterol, lupeol, β-amyrin, catechin and epicatechin from in natura cashew nut testa. Ethanol extracts from stem bark and testa were analyzed for antioxidant activity and total phenol content. The ethanol extract from stem bark exhibited the maximum of antioxidant activity and phenol content.

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Prunin-6″-O-p-coumarate, a new acylated flavanone glycoside from Anacardium occidentale

Cited by 30 publications

References 4 publications

Two new dihydroamentoflavone glycosides fromCycas revoluta

Two new dihydroamentoflavone glycosides fromCycas revoluta

Two New Acylated Flavanone Glycosides from the Leaves and Branches of Phyllanthus emblica.

Fenóis totais, atividade antioxidante e constituintes químicos de extratos de Anacardium occidentale L., Anacardiaceae

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