Saikosaponin homologues from Verbascum spp. The structures of mulleinsaponins I-VII.
From the aerial parts of Verbascum (V.) sinaiticum, V. thapsiforme, V. fruticulosum and Celsia roripifolia, seven new saikosaponin homologues, called mulleinsaponins I-VII, having 13,28-epoxy-olean-11-ene skelton were isolated together with eight known saikosaponin homologues, 3-O-beta-D-fucopyranosyl saikogenin F, saikosaponin a, desrhamnosylverbascosaponin, songarosaponins C, D, mimengoside A and buddlejasaponins I, IV. The structures of mulleinsaponins I-VII were characterized as 3-O-beta-D-glucopyronosyl-(1-->3)-beta-D-fucopyranosyl-6-deoxy- saikogenin F, 3-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->3)-beta-D - fucopyranosyl-16-deoxysaikogenin F, 3-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->3)-beta-D - fucopyranosyl-saikogenin F, 3-O-alpha-L-rhamnopyranosyl- (1-->4)-beta-D-glucopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->2)]-be ta -D-fucopyranosyl-21 beta-hydroxysaikogenin F, 3-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->3)-[beta- D- glucopyranosyl-(1-->2)]-beta-D-fucopyranosyl-21 beta-acetoxysaikogenin F, 3-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D- glucopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->2)]-beta-D- fucopyranosyl-16 beta-acetoxysaikogenin F and 3-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl- (1-->3)-[beta-D-glucopyranosyl-(1-->2)]-beta-D-fucopyranosylsaikogeni n F 16-O-beta-D-glucopyranoside, respectively, from chemical and spectroscopic evidence.
Miyase
T
T
School of Pharmaceutical Sciences, University of Shizuoka, Japan.
Horikoshi
C
C
Yabe
S
S
Miyasaka
S
S
Melek
F R
FR
Kusano
G
G
D002240:Carbohydrate Sequence; D002241:Carbohydrates / Q000032:analysis; D002851:Chromatography, High Pressure Liquid; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009828:Oleanolic Acid / Q000031:analogs & derivatives*; D010936:Plant Extracts / Q000737:chemistry; D012502:Sapogenins / Q000737:chemistry* / Q000145:classification / Q000302:isolation & purification*; D012503:Saponins; D009626:Terminology as Topic
D002241:Carbohydrates; D010936:Plant Extracts; D012502:Sapogenins; D012503:Saponins; D009828:Oleanolic Acid; C025759:saikosaponin D