Biosynthesis of antibiotic prodiginines in the marine bacterium Hahella chejuensis KCTC 2396

Abstract

Aims: Hahella chejuensis KCTC 2396 produces red pigments, showing antibacterial and algicidal activities. The main red‐coloured metabolite of the pigments was identified as antibiotic prodigiosin. With the expectation that the red pigments are a mixture of a series of close relatives, the aim of the present study is to detect new antibiotic prodigiosin analogues and to analyse the biosynthetic pattern for prodiginines in KCTC 2396. Methods and Results: Except prodigiosin, the other constituents in the red pigments were confirmed as well‐known dipyrrolyldipyrromethene prodigiosin, norprodigiosin, and undecylprodiginine. Additionally, four new prodigiosin analogues, each of which was distinguished from prodigiosin (C5), according to differences in alkyl chain length (C3–C7), were detected in small quantities by liquid chromatography mass spectrometry/mass spectrometry spectroscopy. Owing to the presence of a cytotoxic methoxy group, it is expected that all the new prodigiosin analogues are bioactive. Conclusions: Four characterized prodiginines, including prodigiosin and four new prodigiosin analogues are produced in different ratio in KCTC 2396. All of the prodiginines possess a common linear tripyrrolyl structure and a cytotoxic methoxy group. Significance and Impact of the Study: This study shows for the first time that KCTC 2396 is able to produce antibiotic prodigiosin, undecylprodiginine and new prodigiosin analogues in a mixture of pigments. It is also shown that KCTC 2396 possesses a novel system for the simultaneous production of multiple prodiginines in a single micro‐organism.

Antibacterial Colorants: Characterization of Prodiginines and Their Applications on Textile Materials

“…Antibacterial Result. It was reported that prodigiosin has antimicrobial activities (15,17). However, the antibacterial properties could be reduced or lost when the colorants are bound to the fabrics.…”

Exceptional Production of both Prodigiosin and Cycloprodigiosin as Major Metabolic Constituents by a Novel Marine Bacterium, Zooshikella rubidus S1-1

“…The dried crude extract was dissolved in 50% methanol, and 10 l was analyzed by liquid chromatography followed by tandem mass spectrometry (LC-MS/MS) in parallel with reference compounds from Hahella chejuensis KCTC 2396 T . For identification of prodigiosin, cycloprodigiosin, and prodigiosin analogues, the data obtained from the tandem mass spectrometry (MS/MS) analysis were compared with those from literature sources (1,21). Mass Frontier 5.0 (HighChem, Ltd.) software was used to confirm the identity and structure of each compound based on observed fragmentation patterns.…”

Isolation and characterization of pigmented bacteria showing antimicrobial activity from Malaysian marine environment

“…Pigmentation is widespread among bacteria and pigments found in marine heterotrophic bacteria consist of carotenoid, flexirubin, xanthomonadine, and prodigiosin (Kim et al, 2007) plentiful pigment groups, which appear orange, yellow or red (Marit et al, 2010). Antimicrobial activity of marine bacteria is a renowned phenomenon and indicated in a number of studies (Lemos et al, 1985;Dopazo et al, 1988;McCarthy et al, 1994).…”