Isolation and Structure Elucidation of a Novel Yellow Pigment from the Marine Bacterium Pseudoalteromonas tunicata

Abstract

The marine environment is a major source for many novel natural compounds. A new yellow pigment has been isolated from the marine bacterium P. tunicata and identified as a new member of the tambjamine class of compounds. The structural identification was achieved by a combination of 1D and 2D-NMR spectroscopy and high resolution mass spectrometry data.

Inhibition of Fungal Colonization by Pseudoalteromonas tunicata Provides a Competitive Advantage during Surface Colonization

“…Activated longchain fatty acids, in the form of fatty acyl CoAs, are bioactive compounds involved in a variety of processes, such as intracellular protein transport (27), cell signaling (4, 18, 37), translocation of long-chain fatty acids across the plasma membrane (51), and transcriptional control, as well as being the first step in beta oxidation and phospholipid biosynthesis (6). The yellow pigment YP1 produced by P. tunicata contains a 2,2Ј-bipyrrole ring system with an unsaturated 12-carbon alkyl chain (23). YP1 belongs to the tambjamine class of compounds, which have previously been reported to exhibit antimicrobial activities and have been isolated from eukaryotic sources in the marine environment (39).…”

“…Production of AlpP by P. tunicata has been demonstrated to provide a competitive advantage when colonizing a surface in competition with other bacteria (50). In addition, P. tunicata is green due to the production of a yellow pigment, belonging to the tambjamine class of compounds (23), and a purple pigment. Similar to bacterial biofilms, fungal biofilms are enclosed within an exopolysaccharide matrix and may occur on a wide variety of surfaces, including aquatic and terrestrial surfaces, metal, plastics, and plant and animal tissue (3,16).…”

Metabólitos secundários dos nudibrânquios Tambja stegosauriformis, Hypselodoris lajensis e Okenia zoobotryon e dos briozoários Zoobotryon verticillatum e Bugula dentata da costa do Brasil

“…A estereoquímica Z da ligação enamina das tambjaminas pode ser determinada em se observando efeito nOe entre o hidrogênio do carbono C-9 e o grupo metileno CH 2 -1' da cadeia ligada ao nitrogênio, mas não entre CH 2 -1' e os hidrogênios do grupo metoxila. 26 Desta forma, realizamos análises por NOESY, para o estabelecimento da estereoquí-mica do grupo enamina na tambjamina J1 (9), utilizando a tambjamina C (3) como "controle". Para ambos os casos, observamos correlação no espectro NOESY entre o dublete do hidrogênio H-9 (~ d 7,28, CDCl 3 ) e o triplete dos hidrogênios CH 2 -1' (~ d 3,29), mas não entre estes últimos e os hidrogênios da metoxila em d 3,94.…”

“…27 Este sesquiterpeno teve sua estrutura elucidada após a análise dos dados espectroscópicos (RMN 1 H, 13 C, COSY, HSQC e HMBC) e a comparação destes com dados da literatura. 26 Recentemente, a lactona da furodisinina foi isolada a partir do extrato hexânico da esponja marinha Dysidea sp. 20 (provavelmente D. etheria).…”

“…9,10 As tambjaminas parecem estar relacionadas com o mecanismo de defesa química de nudibrânquios do gênero Tambja. 11 Uma série de derivados sintéticos de tambjaminas foi avaliada quanto à sua atividade antimicrobiana e, também, sua citotoxicidade frente a linhagens de células tumorais humanas.…”