Open AccessMetabolomics Reveals Minor Tambjamines in a Marine Invertebrate Food Chain
Author(s) -
Mirelle Takaki,
Vítor F. Freire,
Karen de Jesus Nicácio,
Ariane F. Bertonha,
Nozomu Nagashima,
Richmond Sarpong,
Vinícius Padula,
Antônio G. Ferreira,
Roberto G. S. Berlinck
Publication year - 2020
Publication title -
journal of natural products
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.976
H-Index - 139
eISSN - 1520-6025
pISSN - 0163-3864
DOI - 10.1021/acs.jnatprod.0c01043
Subject(s) - nudibranch , trophic level , biology , invertebrate , marine invertebrates , metabolomics , biomagnification , botany , zoology , ecology , gastropoda , bioinformatics
Metabolomics analysis detected tambjamine alkaloids in aqueous and EtOAc extracts of the marine invertebrates Virididentula dentata , Tambja stegosauriformis , Tambja brasiliensis , and Roboastra ernsti . Among several tambjamines, the new amino acid derivatives tambjamines M-O ( 17 - 19 ) were identified by Marfey's advanced analysis, UPLC-MS/MS analyses, and total synthesis. The tambjamine diversity increased from the bryozoan V. dentata to its nudibranch predators T. stegosauriformis and T. brasiliensis and attained a higher diversity in R. ernsti , the nudibranch that preys upon T. stegosauriformis and T. brasiliensis . The total tambjamine content also increases among the trophic levels, probably due to biomagnification. Tambjamines A ( 1 ), C ( 3 ), and D ( 4 ) are the major metabolites in the tissues of V. dentata , T. stegosauriformis , T. brasiliensis , and R. ernsti and are likely the main chemical defenses of these marine invertebrates.