Siamoside A: a new C-glycosylated flavone from Senna siamea (Lam.) H. S. Irwin & Barneby (Caesalpiniaceae)

Phytochemical investigation of the methanol extracts from the leaves and bark of Senna siamea resulted in the isolation of one new flavone C-glycoside: apigenin-8-C-[6''-(E)-feruloyl]-β- D -glucopyranoside] (1), together with sixteen known compounds including quercetin-3-O-α- L -rhamnoside...

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Published in:	Natural product research Vol. 37; no. 20; pp. 3461 - 3469
Main Authors:	Chedjou, Isaac Nde, Ngouafong, Francis Tatong, Tchuenguem, Roland Tchuenteu, Dzoyem, Jean Paul, Ponou, Beaudelaire Kemvoufo, Teponno, Rémy Bertrand, Barboni, Luciano, Tapondjou, Léon Azefack
Format:	Journal Article
Language:	English
Published:	England Taylor & Francis 18-10-2023 Taylor & Francis Ltd
Subjects:	Acetic acid Antifungal activity antimicrobial activity apigenin-8-C-[6''-(E)-feruloyl]-β Betulinic acid Caesalpiniaceae Catechin Epicatechin Ethyl acetate Fungicides glucopyranoside Inositol Inositols Kaempferol Methanol Microorganisms Minimum inhibitory concentration NMR Nuclear magnetic resonance Quercetin Senna siamea Spectrometry Sucrose Vanillic acid Caesalpiniaceae Senna siamea antimicrobial activity apigenin-8-C-[6''-(E)-feruloyl]-β-D-glucopyranoside
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Abstract	Phytochemical investigation of the methanol extracts from the leaves and bark of Senna siamea resulted in the isolation of one new flavone C-glycoside: apigenin-8-C-[6''-(E)-feruloyl]-β- D -glucopyranoside] (1), together with sixteen known compounds including quercetin-3-O-α- L -rhamnoside (2), vitexin (3), isovitexin (4), quercetin-3-O-β- D -glucopyranoside (5), quercetin-3-O-β- D -arabinopyranoside (6), quercetin (7), kaempferol (8), methyl inositol (9), sucrose (10), betulinic acid (11), vanillic acid (12), stigmastane-3β,6α-diol (13), aurantiamide acetate (14), robinetinidol (15), catechin (16) and epicatechin (17). The structures of these compounds were established on the basis of their spectroscopic (1 D and 2 D NMR) and mass spectrometric (ESI-TOF-MS) data. The methanol extracts, fractions and some of the isolated compounds were screened for their antimicrobial properties against five microbial strains. The methanol extract and the ethyl acetate fraction from the bark showed very weak antifungal activity against C. glabrata with the same MIC value of 128 μg/mL. Compound 7 was weakly active against C. albicans with MIC of 32 μg/mL.
AbstractList	Phytochemical investigation of the methanol extracts from the leaves and bark of resulted in the isolation of one new flavone -glycoside: apigenin-8- -[6''- feruloyl]- - -glucopyranoside] ( ), together with sixteen known compounds including quercetin-3- - - -rhamnoside ( ), vitexin ( ), isovitexin ( ), quercetin-3- - - -glucopyranoside ( ), quercetin-3- - - -arabinopyranoside ( ), quercetin ( ), kaempferol ( ), methyl inositol ( ), sucrose ( ), betulinic acid ( ), vanillic acid ( ), stigmastane-3 ,6 -diol ( ), aurantiamide acetate ( ), robinetinidol ( ), catechin ( ) and epicatechin ( ). The structures of these compounds were established on the basis of their spectroscopic (1 D and 2 D NMR) and mass spectrometric (ESI-TOF-MS) data. The methanol extracts, fractions and some of the isolated compounds were screened for their antimicrobial properties against five microbial strains. The methanol extract and the ethyl acetate fraction from the bark showed very weak antifungal activity against with the same MIC value of 128 μg/mL. Compound was weakly active against with MIC of 32 μg/mL. Phytochemical investigation of the methanol extracts from the leaves and bark of Senna siamea resulted in the isolation of one new flavone C-glycoside: apigenin-8-C-[6''-(E)-feruloyl]-β-D-glucopyranoside] (1), together with sixteen known compounds including quercetin-3-O-α-L-rhamnoside (2), vitexin (3), isovitexin (4), quercetin-3-O-β-D-glucopyranoside (5), quercetin-3-O-β-D-arabinopyranoside (6), quercetin (7), kaempferol (8), methyl inositol (9), sucrose (10), betulinic acid (11), vanillic acid (12), stigmastane-3β,6α-diol (13), aurantiamide acetate (14), robinetinidol (15), catechin (16) and epicatechin (17). The structures of these compounds were established on the basis of their spectroscopic (1 D and 2 D NMR) and mass spectrometric (ESI-TOF-MS) data. The methanol extracts, fractions and some of the isolated compounds were screened for their antimicrobial properties against five microbial strains. The methanol extract and the ethyl acetate fraction from the bark showed very weak antifungal activity against C. glabrata with the same MIC value of 128 μg/mL. Compound 7 was weakly active against C. albicans with MIC of 32 μg/mL. Phytochemical investigation of the methanol extracts from the leaves and bark of Senna siamea resulted in the isolation of one new flavone C-glycoside: apigenin-8-C-[6''-(E)-feruloyl]-β- D -glucopyranoside] (1), together with sixteen known compounds including quercetin-3-O-α- L -rhamnoside (2), vitexin (3), isovitexin (4), quercetin-3-O-β- D -glucopyranoside (5), quercetin-3-O-β- D -arabinopyranoside (6), quercetin (7), kaempferol (8), methyl inositol (9), sucrose (10), betulinic acid (11), vanillic acid (12), stigmastane-3β,6α-diol (13), aurantiamide acetate (14), robinetinidol (15), catechin (16) and epicatechin (17). The structures of these compounds were established on the basis of their spectroscopic (1 D and 2 D NMR) and mass spectrometric (ESI-TOF-MS) data. The methanol extracts, fractions and some of the isolated compounds were screened for their antimicrobial properties against five microbial strains. The methanol extract and the ethyl acetate fraction from the bark showed very weak antifungal activity against C. glabrata with the same MIC value of 128 μg/mL. Compound 7 was weakly active against C. albicans with MIC of 32 μg/mL.
Author	Dzoyem, Jean Paul Ponou, Beaudelaire Kemvoufo Teponno, Rémy Bertrand Barboni, Luciano Ngouafong, Francis Tatong Tapondjou, Léon Azefack Tchuenguem, Roland Tchuenteu Chedjou, Isaac Nde
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Snippet	Phytochemical investigation of the methanol extracts from the leaves and bark of Senna siamea resulted in the isolation of one new flavone C-glycoside:... Phytochemical investigation of the methanol extracts from the leaves and bark of resulted in the isolation of one new flavone -glycoside: apigenin-8- -[6''-...
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SubjectTerms	Acetic acid Antifungal activity antimicrobial activity apigenin-8-C-[6''-(E)-feruloyl]-β Betulinic acid Caesalpiniaceae Catechin Epicatechin Ethyl acetate Fungicides glucopyranoside Inositol Inositols Kaempferol Methanol Microorganisms Minimum inhibitory concentration NMR Nuclear magnetic resonance Quercetin Senna siamea Spectrometry Sucrose Vanillic acid
Title	Siamoside A: a new C-glycosylated flavone from Senna siamea (Lam.) H. S. Irwin & Barneby (Caesalpiniaceae)
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