Antimicrobial Furostanol Saponins from the Seeds of Capsicum annuum L. Var. acuminatum

Abstract

Three new furostanol saponins named capsicoside E (1), capsicoside F (2), and capsicoside G (5) were obtained from the seeds of Capsicum annuum L. var. acuminatum along with known oligoglycosides (3, 4, and 6−10). On the basis of chemical and spectroscopic analyses, the structures of these new furostanol oligoglycosides were elucidated as 26-O-β-d-glucopyranosyl-22-O-methyl-5α-furost-25(27)-en-2α,3β,22ξ,26-tetraol-3-O-β-d-glucopyranosyl(1→3)-β-d-glucopyranosyl(1→2)-[β-d-glucopyranosyl(1→3)]-β-d-glucopyranosyl(1→4)-β-d-galactopyranoside (1), 26-O-β-d-glucopyranosyl-(25R)-5α-furost-20(22)-en-2α,3β,26-triol-3-O-β-d-glucopyranosyl (1→3)-β-d-glucopyranosyl(1→2)-[β-d-glucopyranosyl(1→3)]-β-d-glucopyranosyl(1→4)-β-d-galactopyranoside (2), and 26-O-β-d-gluco-pyranosyl-(25R)-5α-furosta-3β,22ξ,26-triol-3-O-β-d-glucopyranosyl(1→3)-β-d-glucopyranosyl(1→2)-[β-d-glucopyranosyl(1→3)]-β-d-glucopyranosyl(1→4)-β-d-galactopyranoside (5). The isolated saponins showed higher antimicrobial activity against yeasts than against common fungi. Data indicated that the antiyeast activity was related to the combination of the oligosaccharide chain (S1, S2, or S3) with an O-methyl group at R₃ and the presence of a hydroxyl group at the C-2 position. Keywords: Capsicum annuum L.; Solanaceae; red pepper; seeds; furostanol saponins; antiyeast activity