Bireticulol, a bioactive isocoumarin dimer from Streptomyces sp. BCC24731

Boonlarppradab, Chollaratt; Suriyachadkun, Chanwit; Suphothina, Sumalee; Tobwor, Punsa

doi:10.1038/ja.2010.171

Cited by 22 publications

(11 citation statements)

References 25 publications

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“…These biaryl species can then be used as pigments and bioactive compounds with a variety of biological activities, such as antimicrobial, cytotoxic, and enzyme‐inhibitory activities. They have diverse structures, including homodimers coupled at the same position or different positions and heterodimers coupled at the same position or different positions . Furthermore, some of these compounds have axial chirality …”

Section: Methodsmentioning

confidence: 99%

Discovery of a Fungal Multicopper Oxidase That Catalyzes the Regioselective Coupling of a Tricyclic Naphthopyranone To Produce Atropisomers

et al. 2018

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Atropisomeric dinapinones A1 and A2 (DPA1 and DPA2) were isolated from a culture of Talaromyces pinophilus FKI-3864. Monapinone coupling enzyme (MCE), which dimerizes naphthopyranone monapinone A (MPA), was purified from a cell-free extract of T. pinophilus FKI-3864. MCE regioselectively dimerizes MPA at the 8,8'-positions to synthesize the atropisomers DPA1 and DPA2 in a ratio of approximately 1:2.5 without a cofactor. The optimal pH value and temperature for MCE were 4.0 and 50 °C, and the apparent K and V values for MPA were (72.7±23.2) μm and (1.21±0.170) μmol min mg protein. The MCE polypeptide is significantly homologous with multicopper oxidases. Heterologous expression of MCE and functional analysis confirmed that MCE catalyzes the regioselective coupling reaction of MPA to produce DPA. No fungal multicopper oxidase has previously been reported to catalyze regioselective intermolecular oxidative phenol coupling to produce naphthopyranone atropisomers.

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Section: Methodsmentioning

confidence: 99%

Discovery of a Fungal Multicopper Oxidase That Catalyzes the Regioselective Coupling of a Tricyclic Naphthopyranone To Produce Atropisomers

et al. 2018

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“…The cultures were grown at 28°C for 72 hours under constant shaking (120 rpm) using a rotatory shaker. The flasks containing the culture of Z26 were transferred to inoculate 10L fermentor and the large scale fermentation was performed at an aeration rate of 0.5 vvm and agitation of 1000 rpm for ten days (Boonlarppradab et al, 2011).…”

Section: Chemical Characterization Of Active Compounds Fermentation Amentioning

confidence: 99%

Novel Production of Two New Nonpolyenic Antifungal Macrolide Derivatives by Streptomyces Z26 Isolated from Moroccan Rhizospheric Soil

Nafis¹,

Oubaha²,

Elhidar³

et al. 2018

OnLine Journal of Biological Sciences

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The aim of our study was to screen Moroccan actinomycete isolates able to produce nonpolyenic antifungal metabolites in order to contribute to limiting the problem of fungal infections emergence in particular mycotic diseases and to discover known antifungal families, especially nonpolyenic drugs. 480 isolates were tested against 5clinically pathogenic Candida species. Several methods have been used to study the polyenic or non-polyenic nature of the antifungal molecules produced by Actinobacteria (i) The study of the antibacterial activity (the bacterial plasma membrane is devoid of sterols); (ii) The screening of the antimicrobial activity of resistant strains to polyenic antifungals essentially Candida tropicalis R2 and Pythium irregular; (iii) The inhibition of antifungal activity by exogenous ergosterol addition in the culture medium and (iv) The UV-Visible light spectrophotometric analysis of the crude extracts of the actinomycete isolates. Among all isolate tested, only 60 (29 %) showed an antifungal activity against all test microorganisms used. Six active isolates meet all the selection criteria and produced nonpolyenic antifungal metabolites. The taxonomic study of the promising isolate Z26, using morphological, physiological and molecular characters, showed that it has 99,43% of similarity with Streptomyces phytohabitans but there were some differences in morphological characteristics. In addition, the chemical study, using chromatographic and spectroscopic techniques, of the bioactive substances produced in the Z26 isolate fermentation broth in NL300 culture medium allowed the determination of two macrolide derivatives with chemical structures C 62 H 100 O 24 (m/z 1251.6504 [M+Na] +) and C 68 H 110 O 26 (m/z 1365.7174 [M+Na] +). NMR experiments revealed that the active compounds were Novonestmycin A and B. The Novonestmycins A and B are for the first time produced by an actinomycete strain purely isolated from the Moroccan ecosystems.

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“…A total of 18 compounds were isolated from these fractions by repeated silica gel, ODS-A and Sephadex LH-20 CC, as well as preparative HPLC. Among them, (R)-mellein (13, 9.1 mg) (Hirschmann et al, 2005), (R)-6-methoxymellein (14, 2 mg) (Govindachari et al, 1971), (R)-7-hydroxymellein (15, 12.1 mg) (Oliveira et al, 2011), 8-hydroxy-6,7-dimethoxy-3-methyl isocoumarin (16, 4 mg) (Boonlarppradab et al, 2011), stigmast-4-en-6b-ol-3-one (17, 21 mg) (Shao et al, 2013), and (þ)-medioresinol (18, 50 mg) (Yu et al, 2012), were isolated from fraction І. A new alkaloid, O-acetyl-7-methoxy-camptothecin (1, 8 mg), together with eleven known compounds, 10-hydroxy-9-methoxycamptothecin (2, 79 mg) (Aimi et al, 1992), 7-methoxycamptothecin (3, 10 mg) (Arbain et al, 1993), 10-hydroxycamptothecin (4, 17 mg) (Lin and Cordell 1990), 9-methoxycamptothecin (5, 8g) (Pirillo et al, 1995), camptothecin (6, 376 mg) (Ezell and Smith 1991), O-acetylcamptothecin (7, 8 mg) (Wu et al, 1995), 5-hydroxycamptothecin (8a/8b racemic mixture, 45 mg) (Wu et al, 2008), 5-hydroxy-9-methoxycamptothecin (9a/9b racemic mixture, 8 mg) (Wu et al, 2008), mappicine (10, 93 mg) (Govindachari et al, 1974), 9-methoxymappicine (11, 60 mg) (Das and Madhusudan, 1999), and dihydrocamptothecin (12, 38 mg) (Govindachari et al, 1974), were yielded from fraction II.…”

mentioning

confidence: 99%