Two triterpene glycosides from the sea cucumber Bohadschia marmorata Jaeger
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Three new triterpene glycosides, named nobilisides A (1), B (2) and C (3), were isolated from the sea cucumber Holothuria nobilis Selenka. Their structures were deduced by extensive spectral analysis and chemical evidence. Compounds 1 and 3 are non-sulfated monoglycosides while 2 is a sulfated diglycoside. The presence of two conjugated double bonds [22E,24-diene and 7,9(11)-diene] in the aglycone of 1 is a rare structural feature among sea cucumber glycosides, while 2 and 3 possess the same 22,25-epoxy moiety as their side chains. All three glycosides exhibited significant cytotoxicity against human tumor cell lines.
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Three new monosulfated triterpene glycosides, mollisosides A (2), B1 (3), and B2 (4), have been isolated from the sea cucumber Australostichopus mollis. Their structures were determined by NMR and mass spectra. The presence of sulfated glycosides in sea cucumbers belonging to the family Stichopodidae is uncommon.
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Apostichopus japonicus
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Two new triterpene glycosides, scabraside A (1) and B (2), and a structurally known compound (3), were isolated from the sea cucumber Holothuria scabra (Holothuriidae) collected from the South China Sea. Structure of these compounds was elucidated by spectroscopic and chemical methods. The glycosides 1 and 2 exhibit the same common structural features, i. e., the presence of 12- and 17-hydroxy groups in the holostane-type triterpene aglycone with a 9(11)-ene bond, but are different in the side chains of the triterpene aglycone. The glycosides 1 and 2 had significant in vitro cytotoxicity against four human tumor cell lines in comparison to 10-hydroxycamptothecin.
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Three new holostan-type triterpene glycosides, arguside F (1), impatienside B (2), and pervicoside D (3), together with a known saponin, holothurin B (4) were isolated from the sea cucumber Holothuria (Microthele) axiloga H. L. Clark. On the basis of spectroscopic data and chemical reactions, the structures of the new compounds were elucidated. Compound 2 showed significant antifungal activities against six strains (1 ≤ MIC80 ≤ 4 µg/mL). The stereochemistry of holothurin B (4) isolated from the title sea cucumber was also solved through X‐ray diffraction analysis.
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To study the constituents and proportion of triterpene glycosides from sea cucumber S.japonicus of Qingdao,Triterpene glycosides were separated and purified by macroporous resin,Si-gel chromatography and semi-preparative HPLC.Three triterpene glycosides were found and were identified as cladoloside B(1),holotoxin A1(2) and holotoxin B1(3) with an approximate ratio of 1∶4.5∶1.7 based on the chemical evidence and spectral data.
Apostichopus japonicus
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To study the new antifungal active triterpene glycosides of sea cucumber Holothuria scabra. Triterpene glycosides from Holothuria scabra were separated and purified by silica gel chromatography, reversed-phase silica ge1 chromatography and RP-HPLC. Their structures were elucidated on the basis of spectral data and chemical evidence. Three triterpene glycosides were identified as scabraside A (1), echinoside A ( 2) and holothurin A 1 ( 3). Scabraside A ( 1) is a new triterpene glycoside, and compounds 2 and 3 were isolated from Holothuria scabra for the first time. They showed antifungal activities (1≤MIC80≤16 μg·mL −1 ).
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Aim To study the bioactive triterpene glycosides of sea cucumber Holothuria scabra Jaeger.Methods Triterpene glycosides in the sea cucumber were isolated and purified by column chromatography on DA-101,silica gel,reversed-phase silica and reversed HPLC.Their chemical structure were identified on the basis of chemical evidence and spectral data.The cytotoxicities of the compounds obtained were tested with HL-60 cells and MOLT-4 cancer cells.Results Five triterpene glycosides were obtained from the sea cucumber studied and their structures were identified as scabraside C(1),holothurin A1(2),echinoside A(3),24-dehydroechinoside A(4) and holothurin A(5).Their inhibition activities on HL-60,MOLT-4 and A-549 cells were significant.Conclusion Compounds 15 are obstained from Holothuria scabra Jaeger for the first time.All glycosides good show antitumor activity in vitro.
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