Anthocyanins and anthocyanidins in the flowers of Aconitum (Ranunculaceae)
Graphical abstract
Section snippets
Subject and source
The genus Aconitum L. includes about 340 species (The Plant List: http://www.theplantlist.org/) of annual, biennial, or perennial harbs that are native to temperate regions of the Northern Hemisphere (Huxley et al., 1992). Some Aconitum species are used in traditional Chinese medicine (Liu et al., 2017), whereas other species, such as A. napellus and A. carmichaelii, are used as ornamental flowers (Geneve, 2000).
Little has been published about the floral anthocyanins of Aconitum; however,
Previous work
A search only one revealed published report on acylated anthocyanin from the genus Aconitum. Delphinidin 3-O-(6-O-(α-rhamnopyranosyl)-β-glucopyranoside)-7-O-(6-O-(4-O-(6-O-(p-hydroxybenzoyl)-β-glucopyranosyl)-p-hydroxybenzoyl)-β-glucopyranoside) (Violdelphin) was identified from the purplish blue flowers of A. chinense by means of chromatography, FAB-MS, and 1H and 13C NMR (Takeda et al., 1994). Delphinidin and cyanidin have been identified as anthocyanidins from the flowers of A. napellus by
HPLC analysis and thin layer chromatography (TLC)
HPLC analysis was performed on an LC 10A system (Shimadzu Corporation, Kyoto, Japan) using a Waters C18 (4.6 × 250 mm) column with a flow rate of 1 ml/min at 40 °C, and the eluate was monitored at 260 nm for p-hydroxybenzoic acid and at 530 nm for anthocyanidins and anthocyanins. The eluant was applied to a linear gradient elution for 40 min from 20 to 85% solvent B (1.5% H3PO4, 20% HOAc, 25% MeCN in H2O) in solvent A (1.5% H3PO4 in H2O) (Tatsuzawa, 2013).
TLC was carried out on plastic coated
Chemotaxonomic significance
Comparative identification of anthocyanidins by HPLC analysis showed delphinidin was a major anthocyanidin in 29 of 30 taxa of Aconitum. Only A. napellus f. flore albo did not show existence of delphinidin as a major anthocyanidin in this study (Table 1). Trace cyanidin from all Aconitum taxa was detected by HPLC analysis. In addition, pelargonidin was detected as a major anthocyanidin from A. napellus f. flore albo, and was also detected as a trace anthocyanidin from ten other taxa (Table 1).
Acknowledgement
This work was supported in part by JSPS KAKENHI [grant number JP17K07655 and JP19K06011].
References (27)
- et al.
Phytochemistry
(1993) - et al.
Mol. Phylogenetics Evol.
(2012) - et al.
Tetrahedron Lett.
(1991) - et al.
J. Ethnopharmacol.
(2017) - et al.
Phytochemistry
(2002) - et al.
Phytochemistry
(1996) - et al.
Phytochemistry
(1998) - et al.
J. Plant Physiol.
(2013) - et al.
Phytochemistry
(1994) Phytochemistry
(2019)
Phytochemistry
Phytochemistry
Phytochemistry
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