Antifungal cyclopeptides from Halobacillus litoralis YS3106 of marine origin

Yang, Ling; Tan, Renxiang; Wang, Qin; Huang, Wei‐yi; Yin, Yong-xian

doi:10.1016/s0040-4039(02)01458-2

Cited by 83 publications

(46 citation statements)

References 35 publications

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“…Recently, cyclo(L-Phe-L-Pro) and cyclo(L-Phe-trans-4-OH-L-Pro) were isolated from Lactobacillus plantarum MiLAB 393 (30). Among the many cyclodipeptides isolated from nature, cyclo(L-Leu-L-Pro) has been isolated from many living organisms, including Streptomyces (28), Rosellinia necatrix (5), a marine sponge (Rhaphisia pallida) (31), and a marine bacterium (Halobacillus litoralis) (40). It has been reported that cyclo(Pro-Leu) retards the growth of rice seedlings and roots (7) and that it is effective against vancomycin-resistant enterococci and leukemic cells (28).…”

Section: Discussionmentioning

confidence: 99%

Cyclo(l-Leucyl-l-Prolyl) Produced byAchromobacter xylosoxidansInhibits Aflatoxin Production byAspergillus parasiticus

Yan

Song

Sakuno

et al. 2004

Appl Environ Microbiol

165

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Aflatoxins are potent carcinogenic and toxic substances that are produced primarily by Aspergillus flavus and Aspergillus parasiticus. We found that a bacterium remarkably inhibited production of norsolorinic acid, a precursor of aflatoxin, by A. parasiticus. This bacterium was identified as Achromobacter xylosoxidans based on its 16S ribosomal DNA sequence and was designated A. xylosoxidans NFRI-A1. A. xylosoxidans strains commonly showed similar inhibition. The inhibitory substance(s) was excreted into the medium and was stable after heat, acid, or alkaline treatment. Although the bacterium appeared to produce several inhibitory substances, we finally succeeded in purifying a major inhibitory substance from the culture medium using Diaion HP20 column chromatography, thin-layer chromatography, and high-performance liquid chromatography. The purified inhibitory substance was identified as cyclo(L-leucyl-L-prolyl) based on physicochemical methods. The 50% inhibitory concentration for aflatoxin production by A. parasiticus SYS-4 ‫؍(‬ NRRL2999) was 0.20 mg ml Aflatoxins are highly toxic, carcinogenic, and teratogenic secondary metabolites that are produced by certain strains of Aspergillus flavus and Aspergillus parasiticus (reviewed in reference 20). Recently, several strains of Aspergillus nomius, Aspergillus pseudotamarii, Aspergillus bombycis, and Aspergillus ochraceoroseus have also been reported to produce aflatoxin. These fungi are ubiquitous and grow on a variety of agricultural products under appropriate temperature and moisture conditions. Aflatoxins have been detected in numerous agricultural commodities, such as cereal grains, whole wheat, rye breads, oil seeds, cottonseed, etc. (25). The toxicity and carcinogenicity of aflatoxins have made contaminated commodities a significant health hazard all over the world. In fact, the incidence of liver cancer is high in regions with high endemic aflatoxin concentrations. Furthermore, the annual costs resulting from crop losses due to aflatoxin contamination and the costs involved in monitoring and disposal of contaminated commodities affect the agricultural economy (34).Many studies have focused on developing aflatoxin control strategies, including genetic engineering for crop resistance, biological control with competitive, nonaflatoxigenic strains of the fungus A. flavus (6, 9), and regulation of aflatoxin biosynthesis by fungicides, pesticides, inhibitory substances originating from plants, and microbial substances (15,24,27). However, most of these strategies have been shown to be limited in effectiveness. Many microorganisms have been studied to control aflatoxin production. Sweedy and Dobson (32) have reported that bacteria, yeast, molds, actinomycetes, and algae can be used to lower aflatoxin levels in foods and feeds. Ono et al. have reported that aflastatin A, which has been isolated from mycelial extracts of Streptomyces sp., effectively inhibits aflatoxin production (17, 23). Saprophytic yeasts, such as Pichia anomala, Candida krusei, and others, have...

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Section: Discussionmentioning

confidence: 99%

Cyclo(l-Leucyl-l-Prolyl) Produced byAchromobacter xylosoxidansInhibits Aflatoxin Production byAspergillus parasiticus

Yan

Song

Sakuno

et al. 2004

Appl Environ Microbiol

165

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“…[5] In our continuous characterization of biologically active new metabolites from plants, [6] endophytes [7] and marine microbes, [8] we have found that one of the most substantially cytotoxic extracts was derived from the bark of Hopea exalata Lin. Yang et Hsue, collected from Hainan Province of China.…”

Section: Introductionmentioning

confidence: 99%

Hopeanol: A Potent Cytotoxin with A Novel Skeleton from Hopea exalata

Wang

et al. 2006

Eur J Org Chem

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“…For example, five diketopiperazines have been isolated from a cyanobacterium isolated from the sponge Calyx cf. podatypa [32], while other diketopiperazines were reported in the marine bacteria Pseudomonas aeruginosa [35], Halobacillus litoralis Ys3106 [38], and Streptomyces sp. [39] [40], and in the bacterial strains CF-20 and C-148 [36].…”

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confidence: 99%

Proline‐Containing Dipeptides from a Marine Sponge of a Callyspongia Species

Yang

Dong

Zhou

et al. 2009

Helvetica Chimica Acta

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A detailed analysis of the chemical constituents of a marine sponge of Callyspongia sp. was performed. A new proline-containing dipeptide, callyspongidipeptide A (cyclo-((S)-Pro-8-hydroxy-(R)-Ile); 1) along with cyclo-((S)-Pro-(R)-Leu) (3) and seco-((S)-Pro-(R)-Val) (2) were isolated. The structures were determined on the basis of NMR and MS analysis, and the absolute configuration was determined by comparison of the optical rotation with known compounds.Introduction. -Marine sponges produce numerous bioactive compounds with promising pharmaceutical properties. The genus Callyspongia (order Haplosclerida, family Callyspongiidae) is widely distributed and contains various bioactive constituents such as polyacetylenes [1 -11] properties. In the course of our search for cytotoxic metabolites from marine sponges, we have discovered a new proline-containing dipeptide named callyspongidipeptide A (1) from Callyspongia sp., together with the new natural product seco-((S)-Pro-(R)-Val) (2) and the known compound cyclo-((S)-Pro-(R)-Leu) (3). The gross structures of these compounds were elucidated by the aid of COSY, HMQC, and HMBC experiments, while the absolute configuration was determined from the optical rotation. Here, we present the isolation and structure elucidation of these metabolites.

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Antifungal cyclopeptides from Halobacillus litoralis YS3106 of marine origin

Cited by 83 publications

References 35 publications

Cyclo(l-Leucyl-l-Prolyl) Produced byAchromobacter xylosoxidansInhibits Aflatoxin Production byAspergillus parasiticus

Cyclo(l-Leucyl-l-Prolyl) Produced byAchromobacter xylosoxidansInhibits Aflatoxin Production byAspergillus parasiticus

Hopeanol: A Potent Cytotoxin with A Novel Skeleton from Hopea exalata

Proline‐Containing Dipeptides from a Marine Sponge of a Callyspongia Species

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