4.7 Article

Metabolomics Reveals Minor Tambjamines in a Marine Invertebrate Food Chain

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JOURNAL OF NATURAL PRODUCTS
卷 84, 期 3, 页码 790-796

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AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.0c01043

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资金

  1. FAPESP [2002/00943-2, 2006/59457-6, 2013/5022-8, 2015/01017-0, 2019/17721-9, 2015/14114-3]
  2. CNPq [141464/2017-8]
  3. US National Institute of General Medical Sciences [R35 GM130345]

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Metabolomics analysis revealed tambjamine alkaloids in marine invertebrates, with an increase in diversity from bryozoans to nudibranch predators, and higher diversity in nudibranch predators. Total tambjamine content also increases among trophic levels, likely due to biomagnification. Major metabolites include tambjamines A, C, and D.
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.

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