Isolation and structures of erylosides from the Caribbean sponge Erylus formosus

J Nat Prod. 2007 Feb;70(2):169-78. doi: 10.1021/np060364q.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Apoptosis / drug effects
  • Carcinoma, Ehrlich Tumor / metabolism
  • Caribbean Region
  • Drug Screening Assays, Antitumor
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology
  • Mice
  • Molecular Structure
  • Porifera / chemistry*
  • Saponins / chemistry
  • Saponins / isolation & purification*
  • Saponins / pharmacology
  • Spleen / cytology
  • Spleen / drug effects
  • Triterpenes / chemistry*
  • Triterpenes / isolation & purification*
  • Triterpenes / pharmacology

Substances

  • Antineoplastic Agents
  • Glycosides
  • Saponins
  • Triterpenes
  • eryloside F