Cytotoxic and Antifungal Triterpene Glycosides from the Patagonian Sea Cucumber Hemoiedema spectabilis

Abstract

Two new sulfated triterpene glycosides, hemoiedemosides A (1) and B (2), have been isolated from the Patagonian sea cucumber Hemoiedema spectabilis. Their structures have been established by a combination of spectroscopic analysis (NMR and FABMS) and chemical transformations. Both glycosides present the same aglycon and differ in the degree of sulfation of the tetrasaccharide chain. Hemoiedemoside B (2) is a new example of a small number of trisulfated triterpene glycosides from sea cucumbers belonging to the family Cucumariidae. Glycosides 1 and 2 exhibit considerable antifungal activity against the phytopathogenic fungus Cladosporium cucumerinum, while the semisynthetic desulfated derivative 1a is less active.

A New Triterpene Glycoside from the Sea Cucumber Holothuria Scabra Collected in Vietnam

“…To date, dozens of triterpene glycosides of holostane type have been identified from the holothurians [2,3]. They expressed a broad spectrum of antifungal, antibacterial and cytotoxic activity [4,5]. As a part of our on going study on bioactive substances from marine invertebrates, we have isolated several triterpene glycosides from the polar fractions of methanol extracts of the sea cucumber Holothuria scabra collected in Vietnam whose structures were elucidated by spectral data ( 1 H-NMR, 13 C-NMR, DEPT, 2D-NMR and ESI MS).…”

Determination of the triterpene glycosides in sea cucumbers by liquid chromatography with evaporative light scattering and mass spectrometry detection

“…Holotoxin A 1 The triterpene glycoside of Holotoxin A 1 , as an external standard, was obtained following the previously described protocol as in Sections 2.2 and 2.3. The peak of Holotoxin A 1 was collected after the separation performed on the HPLC column, pooled and lyophilized.…”

Scabraside D Extracted from Holothuria scabra Induces Apoptosis and Inhibits Growth of Human Cholangiocarcinoma Xenografts in Mice

“…Many species of sea cucumber produce triterpene glycosides, a group of saponin, which are poisonous for other organisms and presumably function as a chemical defense against predation (Caulier et al, 2011;Bahrami et al, 2014). This group of substances shows various biological activities, including antifungal, cytotoxic, hemolytic, cytostatic and immunomodulatory effects (Kitagaw et al, 1989;Stonix et al, 1999;Chludil et al, 2002). The sea cucumber H. scabra produces a type of sulfated triterpene glycosides called scabraside D, which inhibits the proliferation of…”