Purple anthocyanin colouration on lower (abaxial) leaf surface of Hemigraphis colorata (Acanthaceae)

Purple abaxial colouration of leaves of Hemigraphis colorata (Acanthaceae) is caused by two unusual anthocyanins. [Display omitted] •Hemigraphis colorata leaves with purple abaxial colouration contain two anthocyanins.•The anthocyanins are based on the anthocyanidin 5-O-methylcyanidin.•This anthocyanidin has reduced numbers of possible quinoidal forms.•The major anthocyanin contains the unusual disaccharide 3-glucuronosylglucoside. The functional significance of anthocyanin colouration of lower (abaxial) leaf surfaces is not clear. Two anthocyanins, 5-O-methylcyanidin 3-O-(3″-(β-glucuronopyranosyl)-β-glucopyranoside) (1) and 5-O-methylcyanidin 3-O-β-glucopyranoside (2), were isolated from Hemigraphis colorata (Blume) (Acanthaceae) leaves with strong purple abaxial colouration (2.2 and 0.6mg/gfr.wt., respectively). The glycosyl moiety of 1, the disaccharide 3″-(β-glucuronopyranosyl)-β-glucopyranoside), has previously been reported to occur only in a triterpenoid saponin, lindernioside A. The structural assignment of the aglycone of 1 and 2 is the first complete characterisation of a natural 7-hydroxy-5-methoxyanthocyanidin. Compared to nearly all naturally occurring anthocyanidins, the 5-O-methylation of this anthocyanidin limits the type of possible quinoidal forms of 1 and 2 to be those forms with keto-function in only their 7- and 4′-positions.