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Two new natural compounds, sulfated polyhydroxysteroid, microdiscusol G ( 1 ), and polyhydroxysteroid bioside, microdiscusoside A ( 2 ), along with eight previously known polar steroid substances 3-10 , were isolated from the Arctic starfish Asterias microdiscus . The structures of 1 and 2 have been elucidated by extensive 1D and 2D NMR spectroscopy and HRESIMS techniques. The 28-sulfooxy-24-methylcholestane side chain in 1 has been found among starfish steroid metabolites for the first time. Steroid saponins 9 and 10 exhibited cytotoxic effects against normal cells JB6 Cl41 and cancer cells HT-29, MDA-MB-231, THP-1, and Raji and effectively suppressed cell proliferation and colony formation of cancer cells HT-29 and MDA-MB-231 in non-toxic concentrations. Compounds 5 , 7 , and 8 were inactive or less active in the same experiments.

New asterosaponin, acanthaglycoside G ( 1 ), along with three previously known steroidal oligoglycosides ( 2‒4 ), were isolated from the ethanolic extract of the starfish Acanthaster planci , collected off the coast of Vietnam. The structure of 1 was mainly elucidated by extensive NMR and ESIMS techniques as sodium 6- O -{ β -D-fucopyranosyl-(1→2)- β -D-quinovopyranosyl-(1→4)-[ β -D-quinovopyranosyl-(1→2)]- β -D-quinovopyranosyl-(1→3)- β -D-quinovopyranosyl}-6 α -hydroxy-5 α -pregn-9(11)-en-20-one-3 β -yl sulfate. Compounds 3 and 4 showed slight cytotoxic activities against cancer RPMI-7951, HT-29, and MDA-MB-231 cell lines, but effectively inhibited in non-toxic concentrations colony formation of HT-29 and MDA-MB-231 cells and cell migration of MDA-MB-231 cells. Compounds 1 and 2 were inactive or less active, respectively.

A new triterpene glycoside cucumarioside I2 (1) has been isolated from holothurian Eupentacta fraudatrix. The structure of 1 was elucidated using extensive NMR spectroscopy ((1)H and (13)C NMR, (1)H-(1)H COSY, 1D TOCSY, HSQC, H2BC, HMBC and NOESY) and MALDI-TOF-MS. Glycoside 1 is a disulfated branched pentaoside having rare 3-O-methyl-D-xylose. Cytotoxic activity of the glycoside 1 and known cucumariosides H (2), A5 (3), A6 (4), B2 (5) and B1 (6) against mouse Ehrlich carcinoma cells and their influence on lysosomal activity of mouse peritoneal macrophages have been studied. Glycosides 1 and 5 possessed low cytotoxicities, glycoside 6 was not cytotoxic while compounds 2, 3 and 4 possessed moderate cytotoxicities. Glycosides 1, 3 and 5 increased the lysosomal activity of macrophages on 15-17% at doses of 1-5 μg/mL. Hence lysosomal activity depends on structures of both aglycone and carbohydrate chain and does not have a direct correlation with cytotoxicities of the glycosides.

New triterpene glycosides, cucumariosides H₂ (1), H₃ (2) and H₄ (3), have been isolated from the Far Eastern sea cucumber Eupentacta fraudatrix. The structures of 1-3 were elucidated using extensive NMR spectroscopy (¹H- and ¹³C-NMR, DEPT, ¹H-¹H COSY, 1D TOCSY, H2BC, HMBC, heteronuclear single-quantum coherence, and NOESY) and ESI-MS. Glycosides 1-3 are monosulphated branched pentaosides having rare 3-O-methyl-D-xylose as a terminal monosaccharide. Glycosides 1 and 3 contain holostane aglycones, whereas 2 has a 23,24,25,26,27-pentanorlanostane aglycone with an 18(16)-lactone, which is also uncommon for the sea cucumbers. Glycoside 3 contains a very rare ethoxyl radical at C-25 of the aglycone side chain, and it is most probably an artefact that was formed during long storage of the ethanolic extract. Cytotoxic activities of 1-3 against mouse spleen lymphocytes, haemolytic activity against mouse erythrocytes and Ehrlich carcinoma cells have been studied. The presence of 25-hydroxy group in aglycone moiety significantly decreased the activities.

Two new minor triterpene glycosides, liouvillosides A(4) (1) and A(5) (2) have been isolated from the sea cucumber Staurocucumis liouvillei living in Antarctic and Sub-Antarctic waters. The structures of the new glycosides were elucidated using extensive nuclear magnetic resonance (NMR) spectroscopy ((1)H- and (13)C-NMR spectroscopy, (1)H-(1)H COSY, 1D-TOCSY, HMBC, HSQC and NOESY), ESI-MS and MALDI TOF MS. The glycosides 1 and 2 are disulphated tetraosides having very rare 3-O-methylquinovose as terminal monosaccharide.

Three new diterpene glycosides, virescenosides V (1), W (2), and X (3) have been isolated from a marine strain of Acremonium striatisporum KMM 4401 associated with the holothurian Eupentacta fraudatrix. Their structures have been elucidated on the basis of high resolution mass spectrometry, 1D and 2D NMR (1H, 13C, DEPT, COSY 45, COSY RCT, HSQC, HMBC, and NOESY spectra) as 19-O-beta-D-altropyranosyl-7-oxo-isopimara-8(14),15-diene-2alpha,3beta-diol (1), 19-O-beta-D-altropyranosyl-isopimara-7,15-diene-2 alpha,3 beta,6 alpha-triol (2), and 19-O-beta-D-altropyranosyl-isopimara-8,15-diene-2 alpha,3 beta,7 alpha-triol (3).

New triterpene disulfated tetraoside, pseudostichoposide B (1) has been isolated from the sea cucumber Pseudostichopus trachus. The structure of this glycoside has been deduced by the extensive analysis of NMR and mass-spectra and chemical evidence. Except for a common sulfate group at C-4 of the first xylose residue, pseudostichoposide B contains an additional sulfate group at C-3 of quinovose residue in the carbohydrate chain, not earlier found in sea cucumber glycosides.