ABSTRACT
Four new triterpene glycosides, variegatusides C-F (1-4), together with three structurally known triterpene glycosides, variegatusides A and B (5, 6), and holothurin B (7), were isolated from the sea cucumber Stichopus variegates Semper (Holothuriidae), collected from the South China Sea. Their structures were elucidated on the basis of extensive spectral analysis (nuclear magnetic resonance (NMR) and electrospray ionization mass spectrometry (ESIMS)) and chemical evidence. Variegatusides C-F exhibit the same structural feature consisting of the presence of a 23-hydroxyl group at the holostane-type triterpene aglycone side chain. Variegatuside C (1) has a double bond (24, 25) in this same chain, while variegatuside D (2) exhibits a 8(9)-ene bond in the holostane-type triterpene aglycone, which has not been extracted from other sea cucumber species. Compound 4 is a native compound from the sea cucumber S. variegates Semper, which has been reported to be desacetylstichloroside B1. Except for holothurin B, these glycosides have no sulfate group in their sugar chain and show potent antifungal activities in vitro biotests.
Subject(s)
Antifungal Agents/pharmacology , Glycosides/pharmacology , Stichopus/metabolism , Triterpenes/pharmacology , Animals , Antifungal Agents/chemistry , Antifungal Agents/isolation & purification , China , Glycosides/chemistry , Glycosides/isolation & purification , Magnetic Resonance Spectroscopy , Spectrometry, Mass, Electrospray Ionization , Triterpenes/chemistry , Triterpenes/isolation & purificationABSTRACT
A new sulfated holostane glycoside, leucospilotaside B (1), together with the two related structurally known compounds holothurin B(2) (2) and holothurin B (3), was isolated from sea cucumber Holothuria leucospilota collected from the South China Sea. The structure of 1 was elucidated by spectral analysis (1H-, 13C-, and 2D-NMR, ESI-MS, and HR-ESI-MS) and chemical methods. The compounds 1-3 possess the same disaccharide moiety, but were different in the side chains of the triterpene aglycone. Compound 1 showed significant cytotoxicities against four human tumor cell lines, HL-60, MOLT-4, A-549, and BEL-7402.
Subject(s)
Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Glycosides/chemistry , Glycosides/pharmacology , Holothuria/chemistry , Animals , Antineoplastic Agents/isolation & purification , Cell Line, Tumor , Drug Screening Assays, Antitumor , Glycosides/isolation & purification , Humans , Sulfates/chemistry , Sulfates/isolation & purification , Sulfates/pharmacology , Triterpenes/chemistry , Triterpenes/isolation & purification , Triterpenes/pharmacologyABSTRACT
A new holostane-based triterpene glycoside, arguside A (1), was isolated from the sea cucumber Bohadschia argus, collected in the South China Sea. The structure of the new compound was elucidated by spectroscopic and mass-spectrometric analyses, in combination with chemical transformations. Compound 1 exhibited significant cytotoxicity against different human tumor cell lines, being more active towards HCT-116 cells (IC50 = 0.14 microM) than 10-hydroxycamptothecin (HCP) used as positive control.
