Isolation and structures of erylosides from the Caribbean sponge Erylus formosus |
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Authors: | Antonov Alexandr S Kalinovsky Anatoly I Stonik Valentin A Afiyatullov Shamil S Aminin Dmitry L Dmitrenok Pavel S Mollo Ernesto Cimino Guido |
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Institution: | Laboratory of the MaNaPro Chemistry, Pacific Institute of Bioorganic Chemistry, Vladivostok-22, Russian Federation. |
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Abstract: | Nine new triterpene glycosides, erylosides F1-F4 (1-4), M (5), N (6), O (7), P (8), and Q (9), along with previously known erylosides F (10) and H (11) were isolated from the sponge Erylus formosus collected from the Mexican Gulf (Puerto Morelos, Mexico). Structures of 1-4 were determined as the corresponding biosides having aglycons related to penasterol with additional oxidation patterns in their side chains. Erylosides 5-9 contain new variants of carbohydrate chains with three (5, 6), four (7), and six (8, 9) sugar units, respectively. Erylosides 5, 7, 8, and 6, 9 contain 14-carboxy-24-methylenelanost-8(9)-en-3beta-ol and penasterol as aglycons, respectively. In contrast with its epimer 2, the compound 3 induced the early apoptosis of Ehrlich carcinoma cells at a concentration of 100 microg/mL, while 1 and 10 activated the Ca2+ influx into mouse spleenocytes (130% of the control) at the same doses. |
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