Isolation and structures of erylosides from the Caribbean sponge Erylus formosus.
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.
Antonov
Alexandr S
AS
Laboratory of the MaNaPro Chemistry, Pacific Institute of Bioorganic Chemistry, Vladivostok-22, Russian Federation.
Kalinovsky
Anatoly I
AI
Stonik
Valentin A
VA
Afiyatullov
Shamil S
SS
Aminin
Dmitry L
DL
Dmitrenok
Pavel S
PS
Mollo
Ernesto
E
Cimino
Guido
G
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D017209:Apoptosis / Q000187:drug effects; D002286:Carcinoma, Ehrlich Tumor / Q000378:metabolism; D017691:Caribbean Region; D004354:Drug Screening Assays, Antitumor; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D051379:Mice; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry*; D012503:Saponins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013154:Spleen / Q000166:cytology / Q000187:drug effects; D014315:Triterpenes / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology
D000970:Antineoplastic Agents; D006027:Glycosides; D012503:Saponins; D014315:Triterpenes; C412031:eryloside F