Six new nonsulfated triterpene glycosides, cladolosides B1(1), B2(2), C (3), C1(4), C2(5) and D (6) and known holotoxin A1(7) have been isolated from the tropical Indo-West Pacific sea cucumber Cladolabes schmeltzii (Cladolabinae, Sclerodactylidae, Dendrochirotida). Structures of the glycosides were elucidated by 2D NMR spectroscopy and mass-spectrometry. Glycosides 1 and 2 have pentasaccharide branched carbohydrate moieties and differ from each other by the aglycone structures. Compounds 3–6 are hexaosides; 3–5 contain identical carbohydrate moieties with two terminal 3-O-methylglucose residues and glucose as the fifth sugar unit and differ from each other in the structures of their aglycones. Cladoloside D (6) has a new variant of carbohydrate chain with xylose and glucose residues as fifth and sixth monosaccharides, correspondingly. All of the substances demonstrated rather strong cytotoxic and hemolytic effects.
AvilovS.A., StonikV.A. (1988) New triterpene glycosides from the sea cucumber Cladolabes sp. Khimiya Prirodnykh Soedinenii, 5, 764–765.
2.
MaltsevI.I., StonikV.A., KalinovskyA.I., ElyakovG.B. (1984) Triterpene glycosides from sea cucumber Stichopus japonicus Selenka. Comparative Biochemistry and Physiology, 78B, 421–426; (b) Silchenko AS, Avilov SA, Antonov AS, Kalinin VI, Kalinovsky AI, Smirnov AV, Riguera R, Jimenes C. (2002) Triterpene glycosides from the deep-water North-Pacific sea cucumber Synallactes nozawai Mitsukuri. Journal of Natural Products, 65, 1802–1808; (c) Miyamoto T, Togawa K, Higuchi R, Komori T, Sasaki T. (1992) Structures of four new triterpenoid oligoglycosides: Ds-penaustrosides A, B, C and D from the sea cucumber Pentacta australis. Journal of Natural Products, 55, 940–946.
3.
De Moncerrat Iniguez-MartinezA.M., Guerra-RivasG., RiosT., QuijanoL. (2005) Triterpenoid oligoglycosides from the sea cucumber Stichopus parvimensis. Journal of Natural Products, 68, 1689–1673; (b) Stonik VA, Maltsev II, Kalinovsky AI, Konde K, Elyakov GB. (1982) The glycosides of marine invertebrates. XI. Two new triterpene glycosides from the sea cucumbers of the family Stichopodidae. Khimiya Prirodnykh Soedinenii, 2, 194–199; (c) Stonik VA, Maltsev II, Elyakov GB. (1982) The structure of thelenotosides A and B from the sea cucumber Thelenota ananas. Khimiya Prirodnykh Soedinenii, 5, 624–627; (d) Levin VS, Kalinin VI, Fedorov SN, Smiley S. (1986) The structure of triterpene glycosides and systematic position of two species of sea cucumbers of the family Stichopodidae. Biologiya morya, 4, 72–77.
4.
WangZ., ZhangH., YuanW., GongW., TangH., LiuB., KrohnK., LiL., YiY., ZhangW. (2012) Antifungal nortriterpene and triterpene glycosides from the sea cucumber Apostichopus japonicus Selenka. Food Chemistry, 132, 295–300; (b) Carmichael J, DeGraff WG, Gazdar AF, Minna JD, Mitchel JB. (1987) Evaluation of a tetrazolium-based semiautomated colorimetrie assay: assessment of radiosensitivity. Cancer Research, 47, 936–942; (c) Prokofieva NG, Kalinovskaya NI, Chaikina EL, Kuznetsova TA. (1999) The hemolytic activity of the cyclic acyldepsipeptides from marine isolate of Bacillus pumilus In Biodiversity and allelopathy: from organisms to ecosystems in the Pacific.ChouC.H., WallerG.R., ReinhardtC. (Eds). Academia Sinica, Taipei, 199–203.