A New Sulfated Triterpene Glycoside from the Sea Cucumber Colochirus quadrangularis, and Evaluation of Its Antifungal, Antitumor and Immunomodulatory Activities

The unusual non-holostane triterpene glycoside, colochiroside E (1) was isolated from the sea cucumber Colochirus robustus (Cucumariidae, Dendrochirotida). The structure of 1 was established by analysis of ID, 2D NMR and HRESI MS data. Colochiroside E (1) belongs to a rare group of glycosylated 9β-H-lanosta-18(16)-lactones and has an unprecedented sulfated trisaccharide carbohydrate chain consisting of two glucose and one xylose units. In contrast with (9β-H)-7(8)-unsaturated holostane glycosides, the 7(8)-double bond in the having (9β-H)-configuration aglycone of colochiroside E is not capable of migration into the 8(9)- and then into the 9(11)-position on treatment with HC1. The formation of a chlorine derivative of 1 was observed under these conditions.

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Article

Canadian Journal of Chemistry ◽

10.1139/v97-218 ◽

1998 ◽

Vol 76 (2) ◽

pp. 137-141

Author(s):

Sergey A Avilov ◽

Olga A Drozdova ◽

Vladimir I Kalinin ◽

Anatoly I Kalinovsky ◽

Valentin A Stonik ◽

...

Keyword(s):

Antitumor Activity ◽

Spectral Data ◽

Triterpene Glycoside ◽

Sea Cucumber ◽

Sea Cucumbers ◽

Cucumaria Frondosa

Frondoside C (1) is a new sulfated nonholostane triterpene glycoside obtained (with the glycosides closed by aglycone structure as impurities) from the sea cucumber Cucumaria frondosa. Its structure has been elucidated on the basis of spectral data (NMR and MS) of compound 1 and of its desulfated derivative (2) obtained by solvolysis. Frondoside C (1) is just the seventh glycoside reported from sea cucumbers, having a lanostane-type aglycone devoid of the typical 18(20)- lactone ring.Key words: Cucumaria frondosa, sea cucumbers, frondosides, triterepene glycosides, antitumor activity.

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New Cytotoxic Triterpene Glycoside from the East China Sea Cucumber Holothuria nobilis

Natural Product Communications ◽

10.1177/1934578x1501000207 ◽

2015 ◽

Vol 10 (2) ◽

pp. 1934578X1501000

Author(s):

Jia-Jia Zhang ◽

Qi-Ke Zhu ◽

Jun Wu ◽

Hui-Wen Zhang

Keyword(s):

East China Sea ◽

Triterpene Glycoside ◽

Sea Cucumber ◽

Human Tumor ◽

East China ◽

The East China Sea ◽

Human Tumor Cell ◽

Human Tumor Cell Lines ◽

China Sea ◽

Chemical Evidence

A new cytotoxic triterpene glycoside named nobiliside E (1) has been obtained from the East China Sea cucumber Holothuria nobilis Selenka. Its structure was determined on the basis of NMR spectroscopic and MS analyses, together with chemical evidence. The new compound showed significant cytotoxicity to eight human tumor cell lines with IC50 values in the range of 0.53–4.06 μg/mL.

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Studies on antitumor activities of triterpene glycoside colochiroside A from sea cucumber Colochirus anceps

China Journal of Chinese Materia Medica ◽

10.4268/cjcmm20110429 ◽

2011 ◽

Cited By ~ 1

Author(s):

Yongjuan ZHANG

Keyword(s):

Triterpene Glycoside ◽

Sea Cucumber ◽

Antitumor Activities

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The structure of psoluthurin A, the major triterpene glycoside of the sea cucumber Psolusfabricii

Canadian Journal of Chemistry ◽

10.1139/v83-256 ◽

1983 ◽

Vol 61 (7) ◽

pp. 1465-1471 ◽

Cited By ~ 19

Author(s):

François-Xavier Garneau ◽

Jean-Luc Simard ◽

Odette Harvey ◽

John W. Apsimon ◽

Michel Girard

Keyword(s):

Triterpene Glycoside ◽

Sea Cucumber ◽

Chemical Data ◽

Lawrence Estuary ◽

North Shore ◽

The North ◽

Extraction And Purification ◽

Physico Chemical ◽

St Lawrence Estuary

The isolation of the major triterpene glycoside from the sea cucumber Psolusfabricii obtained from the north shore of the St. Lawrence estuary is described. Versatile extraction and purification procedures were used and physico-chemical data is presented in support of structure 1 for psoluthurin A.

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