title: Isolation and structures of erylosides from the Caribbean sponge Erylus formosus.
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.
authors.affiliation: Laboratory of the MaNaPro Chemistry, Pacific Institute of Bioorganic Chemistry, Vladivostok-22, Russian Federation.
authors.forename: Alexandr S
authors.initials: AS
authors.lastname: Antonov
authors.forename: Anatoly I
authors.initials: AI
authors.lastname: Kalinovsky
authors.forename: Valentin A
authors.initials: VA
authors.lastname: Stonik
authors.forename: Shamil S
authors.initials: SS
authors.lastname: Afiyatullov
authors.forename: Dmitry L
authors.initials: DL
authors.lastname: Aminin
authors.forename: Pavel S
authors.initials: PS
authors.lastname: Dmitrenok
authors.forename: Ernesto
authors.initials: E
authors.lastname: Mollo
authors.forename: Guido
authors.initials: G
authors.lastname: Cimino
mesh_terms: 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
chemical_list: D000970:Antineoplastic Agents; D006027:Glycosides; D012503:Saponins; D014315:Triterpenes; C412031:eryloside F