- A new sulfated triterpene glycoside from the sea cucumber Colochirus quadrangularis, and evaluation of its antifungal, antitumor and immunomodulatory activities
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Our continuing search for marine bioactive secondary metabolites led to the screening of crude extracts of sea cucumbers by the model of Pyricularia oryzae. A new sulfated triterpene glycoside, coloquadranoside A (1), together with four known triterpene glycosides, philinopside A, B, E and pentactaside B (2–5) were isolated from the sea cucumber Colochirus quadrangularis, and their structures were elucidated using extensive spectroscope analysis (ESI-MS, 1D and 2D NMR) and chemical methods. Coloquadranoside A possesses a 16-acetyloxy group in the holostane-type triterpene aglycone with a 7(8)–double bond, a double bond (25,26) at its side chain, and two β-D-xylose in the carbohydrate chain. Coloquadranoside A exhibits in vitro some antifungus, considerable cytotoxicity (IC50 of 0.46–2.03 μM) against eight human tumor cell lines, in vivo antitumor, and immunomodulatory activity.
- Han, Hua,Qi, Xin-Rui,Shen, Li,Tang, Hai-Feng,Xu, Qiang-Zhi,Yang, Wen-Sheng,Yi, Yang-Hua,Yuan, Chun-Hong
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- Pseudocnoside A, a new cytotoxic and antiproliferative triterpene glycoside from the sea cucumber Pseudocnus dubiosus leoninus
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A new triterpene glycoside, pseudocnoside A (1), was isolated from the sea cucumber Pseudocnus dubiosus leoninus. The structure of the new compound was established on the basis of extensive NMR spectroscopic analysis (1H and 13C NMR, 1H,1H-COSY, HMBC, HSQC, TOCSY and NOESY), HR-ESI-MS data and chemical transformations. In addition, the cytotoxicity and antiproliferative activities of 1 and structurally related triterpene glycosides isolated from the sea cucumbers Psolus patagonicus and Hemioedema spectabilis were evaluated against cancer cell lines A-549 and HeLa.
- Careaga, Valeria P.,Bueno, Carlos,Muniain, Claudia,Alche, Laura,Maier, Marta S.
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p. 213 - 220
(2014/04/03)
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- Antifungal nortriterpene and triterpene glycosides from the sea cucumber Apostichopus japonicus Selenka
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A nortriterpene glycoside, 26-nor-25-oxo-holotoxin A1 (1), four triterpene glycosides, including both holostane and non-holostane types analogues, holotoxins D-G (2-5), together with three known triterpene glycosides, holotoxins A1 and B (6, 7), and cladoloside B (8), were isolated from the warty sea cucumber Apostichopus japonicus Selenka, a traditional tonic with high economic value in China. The structures of the new compounds were elucidated by a combination of detailed spectroscopic analysis and chemical methods. This is the first report of a nortriterpene glycoside isolated from sea cucumbers. These compounds showed potent antifungal activities in the in vitro biotest. A preliminary structure-activity analysis suggests that the 18(20) lactone group and the Δ25 terminal double bond may increase the activity. The component of the carbohydrate chain seems play an important role whereas the double bond transformation from Δ 9(11) to Δ7 in the aglycone moiety contributes little to the bioactivity.
- Wang, Zenglei,Zhang, Hongwei,Yuan, Weihua,Gong, Wei,Tang, Hua,Liu, Baoshu,Krohn, Karsten,Li, Ling,Yi, Yanghua,Zhang, Wen
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experimental part
p. 295 - 300
(2012/06/01)
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- Two new cytotoxic disulfated holostane glycosides from the sea cucumber Pentacta quadrangularis
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Two new disulfated triterpene glycosides, pentactasides B and C (1 and 2, resp.), were isolated from the sea cucumber Pentacta quadrangularis collected from the South China Sea. Their structures were elucidated by extensive spectral analysis (2D-NMR and M
- Han, Hua,Xu, Qiang-Zhi,Yi, Yang-Hua,Gong, Wei,Jiao, Bing-Hua
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experimental part
p. 158 - 167
(2010/04/23)
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- Triterpene glycosides from Antarctic sea cucumbers. 1. Structure of liouvillosides A1, A2, A3, B1, and B2 from the sea cucumber Staurocucumis liouvillei: New procedure for separation of highly polar glycoside fractions and taxonomic revision
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Five new triterpene glycosides, liouvillosides A1 (1), A 2 (2), A3 (3), B1 (4), and B2 (5), have been isolated from the Antarctic sea cucumber Staurocucumis liouviellei along with the known liouvilloside A (6), isolated earlier from the same species, and hemoiedemosides A (7) and B (8), isolated earlier from the Patagonian sea cucumber Hemioedema spectabilis. The isolation was carried out using a new chromatographic procedure including application of ion-pair reversed-phase chromatography followed by chiral chromatography on a cyclodextrin ChiraDex column. The structures of the new glycosides were elucidated using extensive NMR spectroscopy (1H and 13C NMR spectrometry, DEPT, 1H-1H COSY, HMBC, HMQC, and NOESY), ESI-FTMS, and CID MS/MS, and chemical transformations. Glycosides 1-3 are disulfated tetraosides and glycosides 4 and 5 are trisulfated tetraosides. Glycosides 2 and 3 contain 3-O-methylquinovose, found for the first time as a natural monosaccharide in sea cucumber glycosides. On the basis of analyses of glycoside structures a taxonomic revision is proposed.
- Antonov, Alexandr S.,Avilov, Sergey A.,Kalinovsky, Anatoly I.,Anastyuk, Stanislav D.,Dmitrenok, Pavel S.,Evtushenko, Evgeny V.,Kalinin, Vladimir I.,Smirnov, Alexey V.,Taboada, Sergi,Ballesteros, Manuel,Avila, Conxita,Stonik, Valentin A.
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experimental part
p. 1677 - 1685
(2009/07/18)
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