Metabolomics Reveals Minor Tambjamines in a Marine Invertebrate Food Chain

Author(s)

Takaki, Mirelle ; Freire, Vitor F. ; Nicacio, Karen J. ; Bertonha, Ariane F. ; Nagashima, Nozomu ; Sarpong, Richmond ; Padula, Vinicius ; Ferreira, Antonio G. ; Berlinck, Roberto G. S.

• Document type: Journal article
• Source: Journal of Natural Products; v. 84, n. 3, p. 7-pg., 2021-03-26.

Abstract

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. (AU)

• FAPESP's process: 19/17721-9 - The role of Chemistry in holobiont adaptation
• Grantee: Roberto Gomes de Souza Berlinck
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 15/01017-0 - Multi-use instrument approved and awarded in the project 2013/50228-8, name of instrument: ultra-performance liquid chromatograph coupled with a high resolution mass spectrometer
• Grantee: Roberto Gomes de Souza Berlinck
• Support Opportunities: Multi-user Equipment Program
• FAPESP's process: 15/14114-3 - Which metabolomics components influence the phytopathogenicity of Colletotrichum spp.?
• Grantee: Mirelle Takaki
• Support Opportunities: Scholarships in Brazil - Doctorate