116524-58-4
Chemical Structure
Cucumarioside H
- CAS No.: 116524-58-4
- Formula:C60H92O29S
- Molecular Weight:1309.42
IUPAC Name: (3R,3aR,4R,5aS,7aS,9R,11aR,11bS,13aS)-9-(((2S,3S,4R,5R)-3-(((2R,3R,4R,5S,6S)-5-(((2S,3S,4S,5S,6R)-4-(((2S,3S,4S,5S)-3,5-dihydroxy-4-methoxytetrahydro-2H-pyran-2-yl)oxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4-hydroxy-6-methyl-3-(((2S,3S,4S,5S)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-4-hydroxy-5-(sulfooxy)tetrahydro-2H-pyran-2-yl)oxy)-3,5a,8,8,11a-pentamethyl-3-((E)-4-methylpenta-1,3-dien-1-yl)-1-oxo-3a,4,5,5a,7,7a,8,9,10,11,11a,11b,12,13-tetradecahydro-1H,3H-naphtho[2',1':4,5]indeno[1,7a-c]furan-4-yl acetate
InChIKey: XPXZTNUAIBRUOQ-IGJXXCHCSA-N
SMILES: O[C@H]1[C@H](O[C@H]([C@H]([C@H]1O[C@H]2[C@H]([C@H]([C@H](CO2)O)OC)O)O)O[C@@H]3[C@@H](O[C@@H]([C@@H]([C@@H]3O)O[C@@H]4OC[C@@H]([C@@H]([C@@H]4O)O)O)O[C@@H]5[C@@H](OC[C@@H](OS(O)(=O)=O)[C@@H]5O)O[C@@H]6CC[C@@]7([C@@H]8CC[C@@]9%10[C@@](C[C@@H](OC(C)=O)[C@@H]9[C@@](/C=C/C=C(C)/C)(OC%10=O)C)(C8=CC[C@@H]7C6(C)C)C)C)C)CO
Biological Activity: Cucumarioside H is a novel triterpene glycoside isolated from the Far Eastern sea cucumber Eupentacta fraudatrix, including H2, H3 and H4. These glycosides have a branched pentasyl structure with a rare 3-O-methyl-D-xylose as the terminal monosaccharide. H2 contains 23,24,25,26,27-pentanolone sterols and has an 18(16)-lactone, which is not common in sea cucumbers. The glycoside portion of H3 contains an extremely rare ethoxyl radical at the 25 position, which may be an artifact formed during the long ethanol extraction process. Studies have shown that H1-3 are cytotoxic to mouse spleen lymphocytes, hemolytic to mouse erythrocytes, and cytotoxic to Ehrlich carcinoma cells. The presence of a 25-hydroxyl group in the glycoside portion significantly reduces these activities.
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Cucumarioside H | Cucumarioside H is a novel triterpene glycoside isolated from the Far Eastern sea cucumber Eupentacta fraudatrix, including H2, H3 and H4. These glycosides have a branched pentasyl structure with a rare 3-O-methyl-D-xylose as the terminal monosaccharide. H2 contains 23,24,25,26,27-pentanolone sterols and has an 18(16)-lactone, which is not common in sea cucumbers. The glycoside portion of H3 contains an extremely rare ethoxyl radical at the 25 position, which may be an artifact formed during the long ethanol extraction process. Studies have shown that H1-3 are cytotoxic to mouse spleen lymphocytes, hemolytic to mouse erythrocytes, and cytotoxic to Ehrlich carcinoma cells. The presence of a 25-hydroxyl group in the glycoside portion significantly reduces these activities. | |||||||||||||||||||||
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Keywords
