Rodriguesic Acids, Modified Diketopiperazines from the Gastropod Mollusc Pleurobranchus areolatus

Author(s)

Pereira, Fabio R. ^[1] ; Santos, Mario F. C. ^[1] ; Williams, David E. ^{[2, 3]} ; Andersen, Raymond J. ^{[2, 3]} ; Padula, Vinicius ^{[4, 5, 6]} ; Ferreira, Antonio G. ^[7] ; Berlinck, Roberto G. S. ^[1]

Affiliation

^[1] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP - Brazil

^[2] Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z1 - Canada

^[3] Univ British Columbia, Dept Earth Ocean & Atmospher Sci, Vancouver, BC V6T 1Z1 - Canada

^[4] SNSB Zool Staatssammlung Munchen, D-81247 Munich - Germany

^[5] Univ Munich, Dept Biol 2, D-81377 Munich - Germany

^[6] Univ Munich, GeoBio Ctr, D-81377 Munich - Germany

^[7] Univ Fed Sao Carlos, Dept Quim, BR-13565905 Sao Carlos, SP - Brazil

• Document type: Journal article
• Source: Journal of the Brazilian Chemical Society; v. 25, n. 4, p. 788-794, Abr. 2014.
• Web of Science Citations: 4

Abstract

In the present investigation, two specimens of the nudipleuran mollusc Pleurobranchus areolatus have shown to accumulate oxidized rodriguesin A derivatives. Rodriguesic acid presents a carboxylic acid replacing the terminal methyl group of the alkyl chain of rodriguesin A. A hydroxamate group was also present on the diketopiperazine moiety of a rodriguesic acid derivative. The structures of both rodriguesic acid and of rodriguesic acid hydroxamate have been established by analysis of spectroscopic data, including their absolute configuration. Two methyl esters of the rodriguesic acids have been isolated as major compounds, but were considered to be isolation artifacts. (AU)

• FAPESP's process: 10/50190-2 - Investigation of metabolic and biotechnological potential of marine organisms in bioremediation processes and for the production of substances with anti-viral, anti-inflammatory and anti-Leishmania activities (Marine Biodiversity)
• Grantee: Roberto Gomes de Souza Berlinck
• Support type: BIOTA-FAPESP Program - Thematic Grants