7-O-methylgossypetin 3-rhamnoside from Atraphaxis pyrifolia

Chumbalov, T. K.; Mukhamed'yarova, M. M.; Omurkamzinova, V. B.; Chanysheva, I. S.

doi:10.1007/bf00570656

Cited by 4 publications

(6 citation statements)

References 8 publications

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“…These were europetin 3- O -α- l -rhamnopyranoside ( 6 ), myricitrin ( 7 ), fisetinidol, gallocatechin ( 14 ), catechin, afzelechin ( 15 ), aromadendrin, epigallocatechin ( 16 ), epicatechin ( 17 ), nikoenoside ( 19 ), N - trans -feruloyldopamine ( 20 ), N - trans -feruloyltyramine ( 21 ), N - p - trans -coumaroyldopamine ( 22 ), N - p - trans -coumaroyltyramine ( 23 ), emodin 8- O -β- d -glucopyranoside, emodin 8- O -(6′- O -malonyl)glucoside, , torachrysone 8- O -β- d -(6′- O -malonyl)glucopyranoside, syringaresinol, dehydroconiferyl alcohol, 3,4,5-trimethoxyphenyl 1- O -β- d -glucopyranoside, and methyl syringate . Compounds 8 – 12 had been isolated previously by Russian research groups and were identified as 8- O -β- d -glucopyranosyl-7- O -methyl-3- O -α- l -rhamnopyranosylgossypetin ( 8 ), 8- O -acetyl-7- O -methyl-3- O -α- l -rhamnopyranosylgossypetin ( 9 ), 7- O -methyl-3- O -α- l -rhamnopyranosylgossypetin ( 10 ), 8- O -acetyl-7- O -methylgossypetin ( 11 ), , and 7- O -methylgossypetin ( 12 ) . These compounds were identified using NMR data based on a comparison with the data for compounds 1 – 5 .…”

Section: Resultsmentioning

confidence: 99%

“…40 Compounds 8−12 had been isolated previously by Russian research groups and were identified as 8-O-β-D-glucopyranosyl-7-O-methyl-3-O-α-L-rhamnopyranosylgossypetin (8), 13 8-O-acetyl-7-O-methyl-3-O-α-L-rhamnopyranosylgossypetin (9), 12 7-O-methyl-3-O-α-L-rhamnopyranosylgossypetin (10), 12 8-O-acetyl-7-O-methylgossypetin (11), 10,12 and 7-O-methylgossypetin (12). 11 These compounds were identified using NMR data based on a comparison with the data for compounds 1−5.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…laetevirens and A . pyrifolia , − and other flavonoids and phenolic compounds were extracted from A . muschketovii and A .…”

mentioning

confidence: 99%

“…From these data, the structure of 18 was assigned as 3,4,5-trimethoxybenzyl α-Lrhamnopyranosyl-(1→6)-β-D-glucopyranoside.The antioxidant activities of the isolated compounds were tested using the DPPH radical scavenging method and compared with a positive control, Trolox, which had an IC 50 value of 28.2 μM. Flavonoids with either pyrogallol or catechol B-ring moieties, including flavonol glycosides (1−3, 6−10), aglycones (4,5,11,12), and catechins (14, 16, 17), showed potent activity (IC 50 7.8−31.3 μM). The phenylpropanoid amides (20, IC 50 30.7 μM; 21, IC 50 41.2 μM) also had radical scavenging activity.…”

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confidence: 99%

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Antioxidant Flavonols and Phenolic Compounds from Atraphaxis frutescens and Their Inhibitory Activities against Insect Phenoloxidase and Mushroom Tyrosinase

et al. 2016

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Chemical investigation of the aerial parts of Atraphaxis frutescens resulted in the isolation of five 7-methoxyflavonols with pyrogallol B-ring moieties (1-5), a fisetinidol glucoside (13), and a benzyl glycoside (18), together with 26 known compounds including flavonoids, phenylpropanoid amides, anthraquinone glycosides, lignans, and a benzyl derivative. The principal chemical structural feature of the isolated compounds was either a pyrogallol or catechol B-ring moiety, and they showed potent 1,1-diphenyl-2-picrylhydrazyl radical scavenging activities. To assess the effects of these antioxidants on biological enzymes, their inhibitory effects against an insect phenoloxidase and a mushroom tyrosinase were evaluated. This study indicated that insect phenoloxidase was inhibited by phenylpropanoid amides and that mushroom tyrosinase was inhibited by the characteristic 7-methoxyflavonol 3-O-rhamnopyranosides.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

“…laetevirens and A . pyrifolia , − and other flavonoids and phenolic compounds were extracted from A . muschketovii and A .…”

mentioning

confidence: 99%

mentioning

confidence: 99%

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Antioxidant Flavonols and Phenolic Compounds from Atraphaxis frutescens and Their Inhibitory Activities against Insect Phenoloxidase and Mushroom Tyrosinase

et al. 2016

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“…Flavonoid glycosides have been found to be the major components of Atraphaxis species [ 10 ]. Few early studies on the phytochemistry of A. pyrifolia leaves reported the compounds: 7- O -methylgossypetin-3- O -α- l -rhamnopyranoside [ 11 ], 7- O -methylluteolin 4’- O - β - d -glucofuranosyl-(1→6)- d -glucopyranoside [ 12 ]; 8-acetylmethylgossypetin 3- O -α- l -rhamnopyranoside (pyrifolin), its aglycone 8-acetyl-7-methylgossypetin (pyrifolidin), and 7-methylgossipetin 3- O -α- l -rhamnopyranoside (pyrifolinin) [ 13 ]; 7-methylgossypetin 8- β - d -glucopyranoside 3- O -α- l -rhamnopyranoside and 7-methylgossipetin 8- β - d -glucopyranoside [ 14 ].…”

Section: Introductionmentioning

confidence: 99%

Phytochemical and Micro-Morphological Characterization of Atraphaxis pyrifolia Bunge Growing in the Republic of Kazakhstan

Abilkassymova,

Kozykeyeva,

Aldana-Mejía

et al. 2024

Molecules

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Atraphaxis pyrifolia is a native species of Central Asia, known for curing several disorders. The species has little knowledges about its chemical composition and any information about its morphological characteristics despite its importance in traditional Asian medicine. This is one of the first approaches to the phytochemical and morphological characterization of this species. Micro-morphology was performed on the stem, and leaf parts of this plant to profile the morpho-anatomical characters using brightfield, fluorescence, polarized and scanning electron microscopy. Leaves were extracted with hexane and methanol. The hexane extract was analyzed using GC-MS analysis revealing the major presence of γ-sitosterol and nonacosane. The methanolic extract was submitted to Vacuum Liquid Chromatography and Sephadex LH-20. HPTLC, HR-ESI-MS and NMR techniques were used to identify the main compounds. Four glycosylated flavonoids were isolated: 8-O-acetyl-7-O-methyl-3-O-α-l-rhamnopyranosylgossypetin (Compound 1), and 7-O-methyl-3-O-α-l-rhamnopyranosylgossypetin (Compound 3), and two other compounds reported for the first time in the literature (Compounds 2 and 4). The findings presented herein furnish pertinent information essential for the identification and authentication of this medicinal plant. Such insights are invaluable for facilitating robust quality control measures and serve as a foundational framework for subsequent endeavours in metabolic, pharmacological, and taxonomical analyses.

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