Frondoside A. A novel triterpene glycoside from the holothurian Cucumariafrondosa

The isolation and characterization of a novel triterpene glycoside from the sea cucumber Cucumariafrondosa, collected from the Gulf of St. Lawrence, are described. Physico-chemical data obtained on the underivatized saponin are presented in support of structure 1 for frondoside A. The structure is characterized by the presence of a branched oligosaccharidic chain composed of five units. The holostane-type aglycone features an endocyclic double bond at position C-7,8 and a β-acetoxy group at C-16. Keywords: triterpene glycoside; Cucumariafrondosa saponins; saponins, triterpene from holothurians; holothurian saponins; echinoderm triterpene saponins.

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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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Isolation and characterization of bioactive peptides from the sea cucumber, Stichopus japonicus

Peptide Science — Present and Future ◽

10.1007/0-306-46864-6_137 ◽

2006 ◽

pp. 419-420 ◽

Cited By ~ 1

Author(s):

M. Ohtani ◽

E. Iwakoshi ◽

Y. Muneoka ◽

H. Minakata ◽

K. Nomoto

Keyword(s):

Sea Cucumber ◽

Bioactive Peptides ◽

Stichopus Japonicus ◽

Isolation And Characterization

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Colochiroside E, an Unusual Non-holostane Triterpene Sulfated Trioside from the Sea Cucumber Colochirus Robustus and Evidence of the Impossibility of a 7(8)-Double Bond Migration in Lanostane Derivatives having an 18(16)-Lactone

Natural Product Communications ◽

10.1177/1934578x1601100611 ◽

2016 ◽

Vol 11 (6) ◽

pp. 1934578X1601100 ◽

Cited By ~ 1

Author(s):

Alexandra S. Silchenko ◽

Anatoly L Kalinovsky ◽

Sergey A. Avilov ◽

Pelageya V. Andryjaschenko ◽

Pavel S. Dmitrenok ◽

...

Keyword(s):

Double Bond ◽

Triterpene Glycoside ◽

Sea Cucumber ◽

Carbohydrate Chain ◽

2D Nmr ◽

Double Bond Migration ◽

Chlorine Derivative ◽

Rare Group

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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