Literature DB >> 33371682

Metabolomics Reveals Minor Tambjamines in a Marine Invertebrate Food Chain.

Mirelle Takaki1, Vítor F Freire1, Karen J Nicacio1, Ariane F Bertonha1, Nozomu Nagashima2, Richmond Sarpong2, Vinicius Padula3, Antonio G Ferreira4, Roberto G S Berlinck1.   

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.

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Year:  2020        PMID: 33371682      PMCID: PMC8627181          DOI: 10.1021/acs.jnatprod.0c01043

Source DB:  PubMed          Journal:  J Nat Prod        ISSN: 0163-3864            Impact factor:   4.050


  20 in total

Review 1.  Reconstructing eukaryotic NAD metabolism.

Authors:  Anthony Rongvaux; Fabienne Andris; Frédéric Van Gool; Oberdan Leo
Journal:  Bioessays       Date:  2003-07       Impact factor: 4.345

2.  Total synthesis and biological evaluation of tambjamine K and a library of unnatural analogs.

Authors:  Leslie N Aldrich; Sydney L Stoops; Brenda C Crews; Lawrence J Marnett; Craig W Lindsley
Journal:  Bioorg Med Chem Lett       Date:  2010-07-23       Impact factor: 2.823

3.  Role and substrate specificity of the Streptomyces coelicolor RedH enzyme in undecylprodiginine biosynthesis.

Authors:  Stuart W Haynes; Paulina K Sydor; Anna E Stanley; Lijiang Song; Gregory L Challis
Journal:  Chem Commun (Camb)       Date:  2008-03-14       Impact factor: 6.222

4.  A new cytotoxic tambjamine alkaloid from the Azorean nudibranch Tambja ceutae.

Authors:  Marianna Carbone; Carlo Irace; Francesca Costagliola; Francesco Castelluccio; Guido Villani; Gonçalo Calado; Vinicius Padula; Guido Cimino; J Lucas Cervera; Rita Santamaria; Margherita Gavagnin
Journal:  Bioorg Med Chem Lett       Date:  2010-02-13       Impact factor: 2.823

5.  Tambjamine alkaloids and related synthetic analogs: efficient transmembrane anion transporters.

Authors:  Paulina Iglesias Hernández; Daniel Moreno; Anatalia Araujo Javier; Tomás Torroba; Ricardo Pérez-Tomás; Roberto Quesada
Journal:  Chem Commun (Camb)       Date:  2011-04-28       Impact factor: 6.222

6.  Role of secondary metabolites in feeding associations between a predatory nudibranch, two grazing nudibranchs, and a bryozoan.

Authors:  B Carté; D J Faulkner
Journal:  J Chem Ecol       Date:  1986-03       Impact factor: 2.626

7.  A mechanism for slow release of biomagnified cyanobacterial neurotoxins and neurodegenerative disease in Guam.

Authors:  Susan J Murch; Paul Alan Cox; Sandra Anne Banack
Journal:  Proc Natl Acad Sci U S A       Date:  2004-08-04       Impact factor: 11.205

Review 8.  Biosynthesis and Bioactivity of Prodiginine Analogs in Marine Bacteria, Pseudoalteromonas: A Mini Review.

Authors:  Francis E Sakai-Kawada; Courtney G Ip; Kehau A Hagiwara; Jonathan D Awaya
Journal:  Front Microbiol       Date:  2019-07-24       Impact factor: 5.640

9.  Genome-wide analyses of the structural gene families involved in the legume-specific 5-deoxyisoflavonoid biosynthesis of Lotus japonicus.

Authors:  Norimoto Shimada; Shusei Sato; Tomoyoshi Akashi; Yasukazu Nakamura; Satoshi Tabata; Shin-Ichi Ayabe; Toshio Aoki
Journal:  DNA Res       Date:  2007-04-23       Impact factor: 4.458

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