New Anthocyanidin and Anthocyanin Pigments from Blue Plumbago

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dc.contributor.authorSkaar, Irene
dc.contributor.authorJordheim, Monica
dc.contributor.authorByamukama, Robert
dc.contributor.authorMbabazi, Angella
dc.contributor.authorWubshet, Sileshi G.
dc.contributor.authorKiremire, Bernard
dc.contributor.authorAndersen, Øyvind M.
dc.date.accessioned2021-12-14T11:03:51Z
dc.date.available2021-12-14T11:03:51Z
dc.date.issued2012
dc.description.abstractPhytochemical investigations of blue plumbago (Plumbago auriculata Poir. syn. Plumbago capensis Thunb.) flowers have led to the isolation of six new anthocyanins based on three new anthocyanidins with 5,7-dimethoxylated A-rings. Their structures were identified by 2D nuclear magnetic resonance and high-resolution mass spectrometry as the 3-O-β- galactopyranosides (1,2,4) and 3-O-α-rhamnopyranosides (3,5,6) of 5,7-dimethyldelphinidin, 5,7-dimethylpetunidin, and 5,7- dimethylmalvidin. Identification of 1−6 implies new structures for the previously reported anthocyanidins pulchellidin, europinidin, and capensinidin to be 5,7-dimethoxy-3,3′,4′,5′-tetrahydroxyflavylium, 5,7,3′-trimethoxy-3,4′,5′-trihydroxyflavylium, and 5,7,3′,5′-tetramethoxy-3,4′-dihydroxyflavylium cations, respectively. The anthocyanins (0.4 mg/g flowers) were accompanied by the dihydroflavonol taxifolin 3′-O-β-glucopyranoside (1.4 mg/g) and the flavonols 5-methylquercetin 3-O-α-rhamnopyranoside (8.8 mg/g) and 5-methylquercetin (0.4 mg/g). The anthocyanins 1−6 are the first reported natural anthocyanins with no free hydroxyl groups in their 5- and 7-positions on their A-rings. They have thus no possibility of forming the tautomeric quinonoidal bases (anhydrobases), which are related to the free hydroxyl groups in the 5- and 7-positions of previously reported anthocyanins. The genes behind the 5,7-dimethoxylated anthocyanins might be useful for making anthocyanins with special properties (colors, etc.).en_US
dc.identifier.other10.1021/jf2048004
dc.identifier.urihttps://nru.uncst.go.ug/xmlui/handle/123456789/483
dc.language.isoenen_US
dc.publisherJournal of agricultural and food chemistryen_US
dc.subjectPlumbago auriculata synen_US
dc.subjectCapensisen_US
dc.subject7-dimethoxylated anthocyanidin A-ringsen_US
dc.subjectCapensinidinen_US
dc.subjectEuropinidinen_US
dc.subjectPulchellidinen_US
dc.titleNew Anthocyanidin and Anthocyanin Pigments from Blue Plumbagoen_US
dc.typeArticleen_US
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