Antimicrobial furostanol saponins from the seeds of Capsicum annuum L. var. acuminatum.
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-beta-D-glucopyranosyl-22-O-methyl-5alpha-furost-25(27)-en-2alpha,3beta,22xi,26-tetraol-3-O-beta-D-glucopyranosyl(1-->3)-beta-D-glucopyranosyl(1-->2)-[beta-D-glucopyranosyl(1-->3)]-beta-D-glucopyranosyl(1-->4)-beta-D-galactopyranoside (1), 26-O-beta-D-glucopyranosyl-(25R)-5alpha-furost-20(22)-en-2alpha,3beta,26-triol-3-O-beta-D-glucopyranosyl (1-->3)-beta-D-glucopyranosyl(1-->2)-[beta-D-glucopyranosyl(1-->3)]-beta-D-glucopyranosyl(1-->4)-beta-D-galactopyranoside (2), and 26-O-beta-D-gluco-pyranosyl-(25R)-5alpha-furosta-3beta,22xi,26-triol-3-O-beta-D-glucopyranosyl(1-->3)-beta-D-glucopyranosyl(1-->2)-[beta-D-glucopyranosyl(1-->3)]-beta-D-glucopyranosyl(1-->4)-beta-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 R(3) and the presence of a hydroxyl group at the C-2 position.
Iorizzi
Maria
M
Dipartimento di Scienze e Tecnologie Agro-Alimentari, Ambientali e Microbiologiche, Università degli Studi del Molise, Via F. De Sanctis, I-86100 Campobasso, Italy. iorizzi@unimol.it
Lanzotti
Virginia
V
Ranalli
Giancarlo
G
De Marino
Simona
S
Zollo
Franco
F
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000302:isolation & purification / Q000494:pharmacology*; D002212:Capsicum / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D004926:Escherichia coli / Q000187:drug effects; D005658:Fungi / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D011549:Pseudomonas / Q000187:drug effects; D012503:Saponins / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D012639:Seeds / Q000737:chemistry*; D015003:Yeasts / Q000187:drug effects
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D012503:Saponins