title: Structure of cucumarioside I2 from the sea cucumber Eupentacta fraudatrix (Djakonov et Baranova) and cytotoxic and immunostimulatory activities of this saponin and relative compounds.
abstract: A new triterpene glycoside cucumarioside I2 (1) has been isolated from holothurian Eupentacta fraudatrix. The structure of 1 was elucidated using extensive NMR spectroscopy ((1)H and (13)C NMR, (1)H-(1)H COSY, 1D TOCSY, HSQC, H2BC, HMBC and NOESY) and MALDI-TOF-MS. Glycoside 1 is a disulfated branched pentaoside having rare 3-O-methyl-D-xylose. Cytotoxic activity of the glycoside 1 and known cucumariosides H (2), A5 (3), A6 (4), B2 (5) and B1 (6) against mouse Ehrlich carcinoma cells and their influence on lysosomal activity of mouse peritoneal macrophages have been studied. Glycosides 1 and 5 possessed low cytotoxicities, glycoside 6 was not cytotoxic while compounds 2, 3 and 4 possessed moderate cytotoxicities. Glycosides 1, 3 and 5 increased the lysosomal activity of macrophages on 15-17% at doses of 1-5 μg/mL. Hence lysosomal activity depends on structures of both aglycone and carbohydrate chain and does not have a direct correlation with cytotoxicities of the glycosides.
authors.affiliation: a G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Division of the Russian Academy of Sciences , Pr. 100-letya Vladivostoka 159, 690022 , Vladivostok , Russian Federation.
authors.forename: Alexandra S
authors.initials: AS
authors.lastname: Silchenko
authors.forename: Anatoly I
authors.initials: AI
authors.lastname: Kalinovsky
authors.forename: Sergey A
authors.initials: SA
authors.lastname: Avilov
authors.forename: Pelageya V
authors.initials: PV
authors.lastname: Andryjaschenko
authors.forename: Pavel S
authors.initials: PS
authors.lastname: Dmitrenok
authors.forename: Ekaterina S
authors.initials: ES
authors.lastname: Menchinskaya
authors.forename: Dmitry L
authors.initials: DL
authors.lastname: Aminin
authors.forename: Vladimir I
authors.initials: VI
authors.lastname: Kalinin
mesh_terms: D000276:Adjuvants, Immunologic / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D006027:Glycosides / Q000737:chemistry / Q000494:pharmacology / Q000633:toxicity; D017737:Macrophages, Peritoneal / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D015394:Molecular Structure; D012503:Saponins / Q000737:chemistry / Q000494:pharmacology / Q000633:toxicity; D012616:Sea Cucumbers / Q000737:chemistry*; D014315:Triterpenes / Q000737:chemistry / Q000494:pharmacology / Q000633:toxicity
chemical_list: D000276:Adjuvants, Immunologic; D006027:Glycosides; D012503:Saponins; D014315:Triterpenes; C033504:cucumarioside