Cladolosides C4, D1, D2, M, M1, M2, N and Q, new triterpene glycosides with diverse carbohydrate chains from sea cucumber Cladolabes schmeltzii. An uncommon 20,21,22,23,24,25,26,27-okta-nor-lanostane aglycone. The synergism of inhibitory action of non-toxic dose of the glycosides and radioactive irradiation on colony formation of HT-29 cancer cells

被引：11

作者：

Silchenko, Alexandra S. ^{[1
]}

Kalinovsky, Anatoly, I ^{[1
]}

Avilov, Sergey A. ^{[1
]}

Andryjaschenko, Pelageya, V ^{[1
]}

Dmitrenok, Pavel S. ^{[1
]}

Yurchenko, Ekaterina A. ^{[1
]}

Ermakova, Svetlana P. ^{[1
]}

Malyarenko, Olesya S. ^{[1
]}

Dolmatov, Igor Yu ^{[2
,3
]}

Kalinin, Vladimir, I ^{[1
]}

机构：

[1] Russian Acad Sci, Far Eastern Branch, GB Elyakov Pacific Inst Bioorgan Chem, Pr 100 Letya Vladivostoka 159, Vladivostok 690022, Russia

[2] Russian Acad Sci, Far Eastern Branch, Sci Ctr Marine Biol, AV Zhirmunsky Inst Marine Biol, Palchevsky St 17, Vladivostok 690041, Russia

[3] Far Eastern Fed Univ, Sukhanova St 8, Vladivostok 690950, Russia

来源：

CARBOHYDRATE RESEARCH | 2018年 / 468卷

基金：

俄罗斯基础研究基金会; 俄罗斯科学基金会;

关键词：

Cladolabes schmeltzii; Triterpene glycosides; Carbohydrate chains; NMR; Cytotoxic activity; Biosynthetic pathways; Radioactive irradiation; ABSOLUTE-CONFIGURATION; BIOLOGICAL ACTION; OLIGOGLYCOSIDES; ASSIGNMENT;

D O I：

10.1016/j.carres.2018.08.003

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Eight new triterpene olygoglycosides, cladolosides C4 (1), D-1(2), D-2(3), M (4), M-1(5), M-2(6), N (7) and Q (8), were isolated from the tropical Indo-West Pacific sea cucumber Cladolabes schmeltzii (Sclerodactylidae, Dendrochirotida). Structures of these glycosides were elucidated by 2D NMR spectroscopy and HR ESI mass spectrometry. A novel hexasaccharide carbohydrate chain having xylose residues as the first, second and third sugars was found in the glycoside 7. Cladoloside C-4 (1) contains an uncommon 20,21,22,23,24,25,26,27-octanorlanostane aglycone. Cladolosides D-1 (2), D-2 (3) and Q (8) were new representatives of the hexaosides with a non-methylated terminal sugar unit in the "upper" half-chain. Cytotoxic activities of the isolated compounds against ascite form of mouse Ehrlich carcinoma cells, mouse erythrocytes and human colorectal adenocarcinoma HT-29 cells were examined and their structure-activity relationships were analyzed. In addition, the majority of tested compounds, except for cladoloside D-2 (3), inhibited the colony formation and growth of HT-29 cells at non-cytotoxic concentrations. The highest inhibitory activity was demonstrated by cladoloside M-1 (5). Moreover, synergism of effects of radioactive irradiation and non-toxic dose of compounds 1-8 decreasing the number of colonies of HT-29 cells was observed. Cladoloside N (7) was the most active and increased the inhibitory effect from radiation by 75%. The biosynthetic transformations of the aglycones are discussed.

引用

页码：36 / 44

页数：9