Biochemically active substances from microorganisms. V. Pyrrothines, potent platelet aggregation inhibitors of microbial origin.

Ninomiya, Yasuyuki; Yamada, Yorinobu; Shirai, Haruyoshi; Onitsuka, Mitsuko; Suhara, Yasuji; Maruyama, Hiromi

doi:10.1248/cpb.28.3157

Cited by 13 publications

(4 citation statements)

References 2 publications

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“…luteus but were not tested against other organisms. Other pharmacological activities reported for the pyrrothines include antifungal activity, potent membrane stabilizing activity, and inhibition of platelet aggregation (20). Aureothricin has also been found to have antitrichomonal activity (21).…”

Section: Resultsmentioning

confidence: 99%

Biologically Active Metabolites from Xenorhabdus Spp., Part 1. Dithiolopyrrolone Derivatives with Antibiotic Activity

McInerney¹,

Gregson²,

Lacey³

et al. 1991

J. Nat. Prod.

138

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Five related antibiotic compounds, named xenorhabdins, were isolated from cultures of Xenorhabdus spp., bacteria symbiotically associated with insect-pathogenic nematodes. Their chemical structures were elucidated by X-ray crystallography, nmr, and mass spectral analyses to be N-acyl derivatives of either 6-amino-4,5-dihydro-5-oxo-1,2-dithiolo [4,3-b] pyrrole (compounds 1-3) or 6-amino-4,5-dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b] pyrrole (compounds 4 and 5). They are previously unreported members of the pyrrothine family of antibiotics. Antimicrobial and insectidical activities were found. These metabolites are specific to phase one Xenorhabdus.

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Section: Resultsmentioning

confidence: 99%

Biologically Active Metabolites from Xenorhabdus Spp., Part 1. Dithiolopyrrolone Derivatives with Antibiotic Activity

McInerney¹,

Gregson²,

Lacey³

et al. 1991

J. Nat. Prod.

138

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“…On the other hand, only a few compounds of microbial origin 5 -7) are inhibitors of platelet aggregation. Ninomiya et al 5 ) have reported that pyrothines, isolated from the culture fluid of Streptomyces, stabilized membranes and prevented platelet aggregation induced by collagen and ADP. Umehara et aI.…”

Section: Biological Properties Of Indole Derivatives and Alkaloidsmentioning

confidence: 99%

Staurosporine, a Potent Platelet Aggregation Inhibitor from aStreptomycesSpecies

Oka

Kodama²,

Takeda³

et al. 1986

Agricultural and Biological Chemistry

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“…Since then, 1 and 2 were repeatedly discovered from various actinomycete strains [ 22 , 23 ]. Isobutanoylpyrrothine(ISP) ( 3 ) ( Figure 1 ) was first isolated from Streptomyces pimprina along with 1 , 2 and a polyene (heptaene) [ 8 ].…”

Section: Isolation and Characterizationmentioning

confidence: 99%

Dithiolopyrrolone Natural Products: Isolation, Synthesis and Biosynthesis

Qin

Huang

et al. 2013

Marine Drugs

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Dithiolopyrrolones are a class of antibiotics that possess the unique pyrrolinonodithiole (4H-[1,2] dithiolo [4,3-b] pyrrol-5-one) skeleton linked to two variable acyl groups. To date, there are approximately 30 naturally occurring dithiolopyrrolone compounds, including holomycin, thiolutin, and aureothricin, and more recently thiomarinols, a unique class of hybrid marine bacterial natural products containing a dithiolopyrrolone framework linked by an amide bridge with an 8-hydroxyoctanoyl chain linked to a monic acid. Generally, dithiolopyrrolone antibiotics have broad-spectrum antibacterial activity against various microorganisms, including Gram-positive and Gram-negative bacteria, and even parasites. Holomycin appeared to be active against rifamycin-resistant bacteria and also inhibit the growth of the clinical pathogen methicillin-resistant Staphylococcus aureus N315. Its mode of action is believed to inhibit RNA synthesis although the exact mechanism has yet to be established in vitro. A recent work demonstrated that the fish pathogen Yersinia ruckeri employs an RNA methyltransferase for self-resistance during the holomycin production. Moreover, some dithiolopyrrolone derivatives have demonstrated promising antitumor activities. The biosynthetic gene clusters of holomycin have recently been identified in S. clavuligerus and characterized biochemically and genetically. The biosynthetic gene cluster of thiomarinol was also identified from the marine bacterium Pseudoalteromonas sp. SANK 73390, which was uniquely encoded by two independent pathways for pseudomonic acid and pyrrothine in a novel plasmid. The aim of this review is to give an overview about the isolations, characterizations, synthesis, biosynthesis, bioactivities and mode of action of this unique family of dithiolopyrrolone natural products, focusing on the period from 1940s until now.

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Biochemically active substances from microorganisms. V. Pyrrothines, potent platelet aggregation inhibitors of microbial origin.

Cited by 13 publications

References 2 publications

Biologically Active Metabolites from Xenorhabdus Spp., Part 1. Dithiolopyrrolone Derivatives with Antibiotic Activity

Biologically Active Metabolites from Xenorhabdus Spp., Part 1. Dithiolopyrrolone Derivatives with Antibiotic Activity

Staurosporine, a Potent Platelet Aggregation Inhibitor from aStreptomycesSpecies

Dithiolopyrrolone Natural Products: Isolation, Synthesis and Biosynthesis

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