A chemical study on the steroidal glycosides from Atropa belladonna L. seeds.
Eight steroidal glycosides of the spirostane type tentatively named atroposides A, B, C, D, E, F, G, and H (according to their increase in polarity) have been isolated from the methanolic extract of Atropa belladonna L. seeds by Sephadex gel filtration and column chromatography on silica gel impregnated with AgNO3. The structure of atroposides A, C, E, G has been elucidated as 3-O-alpha-D-galactopyranoside; 3-O-beta-D-glucopyranosyl(1-->4)-beta-D-galactopyranoside; 3-O-beta-D-glucopyranosyl (1-->2) -beta-D-glucopyranosyl(1-->4)-beta-D-galactopyranoside; and 3-O-alpha-L-rhamnopyranosyl (1-->4)-beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->4)-beta-D-galactopyranoside, each of (25R)-5 alpha-spirostane-3 beta-ol, respectively. The structure of atroposides B, D, F, and H has been elucidated as 3-O-beta-D-galactopyranoside; 3-O-beta-D-glucopyranosyl (1-->4)beta-D-galactopyranoside; 3-O-beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->4)-beta-D-galactopyranoside; 3-O-alpha-L-rhamnopyranosyl (1-->4)-B-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->4)-beta-D-galactopyranoside, each of (25R)-spirost-5-en-3-b-0l, respectively.
Shvets
S A
SA
Institute of Genetics, Academy of Sciences, Chisinau, Moldova.
Latsterdis
N V
NV
Kintia
P K
PK
D001532:Atropa belladonna / Q000737:chemistry*; D002240:Carbohydrate Sequence; D002850:Chromatography, Gel; D006027:Glycosides / Q000737:chemistry; D006868:Hydrolysis; D008969:Molecular Sequence Data; D010936:Plant Extracts / Q000737:chemistry; D010946:Plants, Medicinal; D010947:Plants, Toxic; D012639:Seeds / Q000737:chemistry; D013256:Steroids / Q000737:chemistry*
D006027:Glycosides; D010936:Plant Extracts; D013256:Steroids