Saponins from Allium minutiflorum with antifungal activity.
Three saponins, named minutoside A (1), minutoside B (2), minutoside C (3), and two known sapogenins, alliogenin and neoagigenin, were isolated from the bulbs of Allium minutiflorum Regel. Elucidation of their structure was carried out by comprehensive spectroscopic analyses, including 2D NMR spectroscopy and mass spectrometry. The structures of the new compounds were identified as (25R)-furost-2alpha,3beta,6beta,22alpha,26-pentaol 3-O-[beta-D-xylopyranosyl-(1-->3)-O-beta-D-glucopyranosyl-(1-->4)-O-beta-D-galactopyranosyl] 26-O-beta-D-glucopyranoside (1), (25S)-spirostan-2alpha,3beta,6beta-triol 3-O-beta-D-xylopyranosyl-(1-->3)-O-beta-D-glucopyranosyl-(1-->4)-O-beta-D-galactopyranoside (2), and (25R)-furost-2alpha,3beta,5alpha,6beta,22alpha,26-esaol 3-O-[beta-D-xylopyranosyl-(1-->3)-O-beta-D-glucopyranosyl-(1-->4)-O-beta-D-galactopyranosyl] 26-O-beta-D-glucopyranoside (3). The isolated compounds were evaluated for their antimicrobial activity. All the novel saponins showed a significant antifungal activity depending on their concentration and with the following rank: minutoside B>minutoside C>>minutoside A. No appreciable antibacterial activity was recorded. The possible role of these saponins in plant-microbe interactions is discussed.
Barile
Elisa
E
Dipartimento di Scienze e Tecnologie Agroalimentari, Ambientali e Microbiologiche, Università del Molise, Via F. De Sanctis, 86100 Campobasso, Italy.
Bonanomi
Giuliano
G
Antignani
Vincenzo
V
Zolfaghari
Behzad
B
Sajjadi
S Ebrahim
SE
Scala
Felice
F
Lanzotti
Virginia
V
D000490:Allium / Q000737:chemistry*; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D002240:Carbohydrate Sequence; D005658:Fungi / Q000187:drug effects; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D012503:Saponins / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D021241:Spectrometry, Mass, Electrospray Ionization; D013256:Steroids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology
D000935:Antifungal Agents; D006027:Glycosides; D012503:Saponins; D013256:Steroids; C504674:minutoside A; C504675:minutoside B