Evaluation of the Seasonality and Extraction Method on the Polar Extracts of Croton grewioides Baill. by Chromatogram Fingerprinting and Isolation of a New Triglycosylated Flavonoid

Croton grewioides Baill. popularly known as “canelinha” or “canelinha-de-cheiro” has been used for the treatment of influenza, antitussive, febrifuge and headache; however, the study of its phytochemical composition is limited. The aim of this study was to investigate the effect of the extraction method and seasonality through leaf extracts of four accessions of Croton grewioides by fingerprint chromatograms aided by principal component analysis to analyze the differences and similarities among the samples. We aimed also to provide chemical characterization of isolated secondary metabolites using semi-preparative liquid chromatography. The results showed that only the chemical profile of the methanolic extracts of accessions 101 and 113 were influenced by the seasonality. For the first time, four flavonoids were isolated through semi-preparative chromatography in this species, characterized as quercetin 3-O-β-D-galactopyranosyl-(1→2)-α-L-rhamnopyranoside-(1→6)-α-L-rhamnopyranoside (1), quercetin 3-O-β-D-galactopyranosyl-(1→2)-α-apiopyranoside-(1→6)-α-L-rhamnopyranoside (2), quercetin 3-O-glucopyranoside (3) and 3-O-methyl-quercetin (4), the flavonoid (2) has been recognized as a new triglycosylated derivative.