Marinone and debromomarinone: Antibiotic sesquiterpenoid naphthoquinones of a new structure class from a marine bacterium

Pathirana, Charles; Jensen, Paul R.; Fenical, William

doi:10.1016/0040-4039(93)88010-g

Cited by 105 publications

(65 citation statements)

References 12 publications

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“…To examine this possibility, additional experiments are necessary. To date, some actinomycete strains are known to produce polyketide-isoprenoid hybrid compounds, such as FQ A (23), naphterpin (38), napyradiomycin A (40), and marinone (33). Among them, naphterpin (37,42) and napyradiomycin A (39) producers have been shown to possess both the MEP and MV pathways.…”

Section: Discussionmentioning

confidence: 99%

“…These moieties are biosynthesized via pathways independent of isoprenoids to further give rise to the so-called isoprenoidhybrid compounds, such as novobiocin (27), clorobiocin (27), brasilicardin A (22), KS505a (31), and lavanducyanin (16). Moreover, several actinomycete strains are known to produce polyketide-isoprenoid hybrid compounds, such as furaquinocin (FQ) (23), naphterpin (38), napyradiomycin (40), and marinone (33), all of which were reported to show biological activities and could act as an antitumor drug, an antioxidative agent, a nonsteroidal estrogen receptor antagonist, and an anticancer drug, respectively. Considering that the structures of polyketide moieties, which are derived from 1,3,6,8-tetrahydroxynaphthalene (THN), are almost the same in these compounds, the prenyl moieties are suggested to play important roles in exhibiting diversity in the biological activities of these compounds.…”

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confidence: 99%

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Biosynthesis of a Natural Polyketide-Isoprenoid Hybrid Compound, Furaquinocin A: Identification and Heterologous Expression of the Gene Cluster

et al. 2006

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Furaquinocin (FQ) A, produced by Streptomyces sp. strain KO-3988, is a natural polyketide-isoprenoid hybrid compound that exhibits a potent antitumor activity. As a first step toward understanding the biosynthetic machinery of this unique and pharmaceutically useful compound, we have cloned an FQ A biosynthetic gene cluster by taking advantage of the fact that an isoprenoid biosynthetic gene cluster generally exists in flanking regions of the mevalonate (MV) pathway gene cluster in actinomycetes. Interestingly, Streptomyces sp. strain KO-3988 was the first example of a microorganism equipped with two distinct mevalonate pathway gene clusters. We were able to localize a 25-kb DNA region that harbored FQ A biosynthetic genes (fur genes) in both the upstream and downstream regions of one of the MV pathway gene clusters (MV2) by using heterologous expression in Streptomyces lividans TK23. This was the first example of a gene cluster responsible for the biosynthesis of a polyketide-isoprenoid hybrid compound. We have also confirmed that four genes responsible for viguiepinol [3-hydroxypimara-9(11),15-diene] biosynthesis exist in the upstream region of the other MV pathway gene cluster (MV1), which had previously been cloned from strain KO-3988. This was the first example of prokaryotic enzymes with these biosynthetic functions. By phylogenetic analysis, these two MV pathway clusters were identified as probably being independently distributed in strain KO-3988 (orthologs), rather than one cluster being generated by the duplication of the other cluster (paralogs).

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Section: Discussionmentioning

confidence: 99%

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confidence: 99%

Biosynthesis of a Natural Polyketide-Isoprenoid Hybrid Compound, Furaquinocin A: Identification and Heterologous Expression of the Gene Cluster

et al. 2006

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“…These biological activities have justified the large number of studies found in the literature aimed at the synthesis and evaluation of either natural quinones or their analogues as potential pharmacological agents [10]. In fact, some clinically antimicrobial drugs such as marinone debromomarinone [11], contain the quinone moiety as a relevant part of their structures.…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial Activities of the Henna Extract and Some Synthetic Naphthoquinones Derivatives

Rahmoun¹,

Boucherit-Atmani²,

Benabdallah³

et al. 2013

AJMBR

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Naphthoquinones are compounds widely distributed in the environment, both as natural products and as pharmaceutical agents. They have been the subject of much research due to their pharmacological activities. In this study, methanol extract of henna and a series of synthesized structural analogue of lawsone have been assessed for their antimicrobial activities. Methanol extract of henna and eight naphthoquinones derivatives were tested as potential antimicrobial agents against twelve bacteria and three Candida species using the agar disc diffusion and broth microdilution methods according to guidelines recommended by the Clinical and Laboratory Standards Institute. Besides 2b and 3b, methanol extract and all the synthesized compounds 1a, 2a, 1b and 1c, 2c and 3c showed weakto-strong activity against at least one tested strain. However, the compounds 1c and 1b were found to have the most effective activity against pathogenic bacteria and displayed an activity 8 to 64 fold higher than that othe structural analogue, lawsone. Their MICs ranged from 8-64 µg ml -1. Henna extract was found to have an interesting activity. Our results indicate an effective in vitro activity of 1,4-naphthoquinone derivatives and suggest the benefits of further studies for its application in antibiotherapy.

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“…However, in most cases, the biological activity of henna against ringworm and its etiological agents is related to the ability of quinones to accept one or two electrons from microorganisms to form highly reactive radical anion intermediates, which are responsible for the oxidative stress observed in the microbial cells [18]. In fact, some clinically active antimicrobial drugs, such as marinone debromomarinone, contain the quinone moiety as a relevant part of their structures [19]. Quinonoid compounds by virtue of their easy redox cycling capacity are known to possess wide-ranging antimicrobial as well as anti-cancer features.…”

Section: In Vivo Antidermatophytic Assaymentioning

confidence: 99%

In Vitro and in Vivo Anti Dermatophytes Activity of Lawsonia Inermis L. (Henna) Leaves against Ringworm and Its Etiological Agents

Wagini¹,

Abbas²,

Soliman³

et al. 2014

AJCEM

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Abstract:The study was carried out to identify the etiological agents causing ringworm, evaluate the in vitro and in vivo antifungal activity of Lawsonia inermis L. In vitro study was carried out using agar dilution method. In a total of 50 clinical samples, 4 different species were identified namely; Microsporum canis, Trichophyton tonsurans, Trichophyton rubrum, and Trichophyton mentagrophytes. However, the results showed that hexane extract exerted a strong antifungal activity against all the identified etiological agents, with a minimum inhibitory concentration of 625µg/ml except Microsporum canis which resisted the minimum concentration but susceptible to the higher concentrations. The in vivo study was carried out using 15 naturally infected goats. First, second and third group of animals were treated with henna paste, aqueous and ethanolic extract respectively, fourth group were treated with clotrimazole as a positive control while negative control (fifth) group were left untreated with neither henna nor clotrimazole. The treatments were compared and the results showed that henna paste had the highest efficacy against all the types of ringworm tested compared to the remaining treatments. Disappearance of lesion and complete repair of the hair was observed at 30 days after treatment. Significantly similar result was observed in the group of animals treated with aqueous extract, ethanol extract, and clotrimazole in all the parameters. Significant different was only observed between groups treated and negative control.

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Marinone and debromomarinone: Antibiotic sesquiterpenoid naphthoquinones of a new structure class from a marine bacterium

Cited by 105 publications

References 12 publications

Biosynthesis of a Natural Polyketide-Isoprenoid Hybrid Compound, Furaquinocin A: Identification and Heterologous Expression of the Gene Cluster

Biosynthesis of a Natural Polyketide-Isoprenoid Hybrid Compound, Furaquinocin A: Identification and Heterologous Expression of the Gene Cluster

Antimicrobial Activities of the Henna Extract and Some Synthetic Naphthoquinones Derivatives

In Vitro and in Vivo Anti Dermatophytes Activity of Lawsonia Inermis L. (Henna) Leaves against Ringworm and Its Etiological Agents

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