title: Solanum incanum and S. heteracanthum as sources of biologically active steroid glycosides: confirmation of their synonymy.
abstract: A new spirostanol saponin (1), along with four known saponins, dioscin (2), protodioscin (3), methyl-protodioscin (4), and indioside D (5), and one known steroid glycoalkaloid solamargine (6) were isolated from the two synonymous species, Solanum incanum and S. heteracanthum. The structure of the new saponin was established as (23S,25R)-spirost-5-en-3β,23-diol 3-O-{β-D-xylopyranosyl-(1→2)-O-α-L-rhamnopyranosyl-(1→4)-[O-α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside}, by using a combination of 1D and 2D NMR techniques including (1)H, (13)C, COSY, TOCSY, NOESY, HSQC and HMBC experiments and by mass spectrometry. The compounds 1, 3, 4 and 5 were evaluated for cytotoxicity against five cancer cell lines and for antioxidant and cytoprotective activity.
authors.affiliation: EA 4267 (FDE/UFC), Laboratoire de Pharmacognosie, Faculté de Pharmacie, Université de Bourgogne, Dijon, France.
authors.forename: Mahenina Jaovita
authors.initials: MJ
authors.lastname: Manase
authors.forename: Anne-Claire
authors.initials: AC
authors.lastname: Mitaine-Offer
authors.forename: David
authors.initials: D
authors.lastname: Pertuit
authors.forename: Tomofumi
authors.initials: T
authors.lastname: Miyamoto
authors.forename: Chiaki
authors.initials: C
authors.lastname: Tanaka
authors.forename: Stéphanie
authors.initials: S
authors.lastname: Delemasure
authors.forename: Patrick
authors.initials: P
authors.lastname: Dutartre
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Mirjolet
authors.forename: Olivier
authors.initials: O
authors.lastname: Duchamp
authors.forename: Marie-Aleth
authors.initials: MA
authors.lastname: Lacaille-Dubois
mesh_terms: D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use; D000975:Antioxidants / Q000302:isolation & purification / Q000494:pharmacology* / Q000627:therapeutic use; D045744:Cell Line, Tumor; D004144:Diosgenin / Q000031:analogs & derivatives* / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use; D006027:Glycosides / Q000302:isolation & purification / Q000494:pharmacology* / Q000627:therapeutic use; D006801:Humans; D051379:Mice; D015394:Molecular Structure; D009369:Neoplasms / Q000188:drug therapy*; D008517:Phytotherapy; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology* / Q000627:therapeutic use; D012503:Saponins / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology* / Q000627:therapeutic use; D012991:Solanaceous Alkaloids / Q000737:chemistry / Q000302:isolation & purification; D032322:Solanum / Q000737:chemistry* / Q000145:classification; D013045:Species Specificity; D013150:Spirostans / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D013256:Steroids / Q000302:isolation & purification / Q000494:pharmacology* / Q000627:therapeutic use
chemical_list: C576440:(23S,25R)-spirost-5-en-3beta,23-diol 3-O-(beta-D-xylopyranosyl-(1-2)-O-alpha-L-rhamnopyranosyl-(1-4)-(O-alpha-L-rhamnopyranosyl-(1-2))-beta-D-glucopyranoside); D000972:Antineoplastic Agents, Phytogenic; D000975:Antioxidants; D006027:Glycosides; D010936:Plant Extracts; D012503:Saponins; D012991:Solanaceous Alkaloids; D013150:Spirostans; D013256:Steroids; C428264:indioside D; C026609:beta-solamarine; C459619:protodioscin; D004144:Diosgenin