title: Structures and cytotoxic properties of cucumariosides H₂, H₃ and H₄ from the sea cucumber Eupentacta fraudatrix.
abstract: New triterpene glycosides, cucumariosides H₂ (1), H₃ (2) and H₄ (3), have been isolated from the Far Eastern sea cucumber Eupentacta fraudatrix. The structures of 1-3 were elucidated using extensive NMR spectroscopy (¹H- and ¹³C-NMR, DEPT, ¹H-¹H COSY, 1D TOCSY, H2BC, HMBC, heteronuclear single-quantum coherence, and NOESY) and ESI-MS. Glycosides 1-3 are monosulphated branched pentaosides having rare 3-O-methyl-D-xylose as a terminal monosaccharide. Glycosides 1 and 3 contain holostane aglycones, whereas 2 has a 23,24,25,26,27-pentanorlanostane aglycone with an 18(16)-lactone, which is also uncommon for the sea cucumbers. Glycoside 3 contains a very rare ethoxyl radical at C-25 of the aglycone side chain, and it is most probably an artefact that was formed during long storage of the ethanolic extract. Cytotoxic activities of 1-3 against mouse spleen lymphocytes, haemolytic activity against mouse erythrocytes and Ehrlich carcinoma cells have been studied. The presence of 25-hydroxy group in aglycone moiety significantly decreased the activities.
authors: Laboratory of Chemistry of Marine Natural Products, Pacific Institute of Bioorganic Chemistry of the Far East Division of the Russian Academy of Sciences, 690022 Vladivostok, Russia.
authors: Alexandra S
authors: AS
authors: Silchenko
authors: Anatoly I
authors: AI
authors: Kalinovsky
authors: Sergey A
authors: SA
authors: Avilov
authors: Pelageya V
authors: PV
authors: Andryjaschenko
authors: Pavel S
authors: PS
authors: Dmitrenok
authors: Ekaterina A
authors: EA
authors: Yurchenko
authors: Vladimir I
authors: VI
authors: Kalinin
mesh_terms: D000818:Animals; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002286:Carcinoma, Ehrlich Tumor / Q000188:drug therapy; D004305:Dose-Response Relationship, Drug; D004353:Drug Evaluation, Preclinical; D004912:Erythrocytes / Q000187:drug effects; D006027:Glycosides / Q000737:chemistry* / Q000494:pharmacology*; D053878:Hemolytic Agents / Q000494:pharmacology; D008214:Lymphocytes / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D015394:Molecular Structure; D012616:Sea Cucumbers / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013154:Spleen / Q000166:cytology; D014315:Triterpenes / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D006027:Glycosides; D053878:Hemolytic Agents; D014315:Triterpenes; C577994:cucumarioside H2; C577992:cucumarioside H3; C577993:cucumarioside H4