Journal
NATURAL PRODUCT RESEARCH
Volume 27, Issue 19, Pages 1776-1783Publisher
TAYLOR & FRANCIS LTD
DOI: 10.1080/14786419.2013.778851
Keywords
Eupentacta fraudatrix; triterpene glycosides; cucumarioside I-2; macrophage lysosomal activity; cytotoxic activity; sea cucumbers
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Funding
- Presidium of the Russian Academy of Science Program Molecular and cell biology
- Russian Federation Program for Support of the Leading Scientific Schools Grant [SSh-546.2012.4]
- FEB RAS [13-III-B-05-069]
- RFBR [11-04-00480-a, 11-04-00052a]
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A new triterpene glycoside cucumarioside I-2 (1) has been isolated from holothurian Eupentacta fraudatrix. The structure of 1 was elucidated using extensive NMR spectroscopy (H-1 and C-13 NMR, H-1-H-1 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), A(5) (3), A(6) (4), B-2 (5) and B-1 (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 1-5g/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.
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