3-Methoxy-2,5-toluquinone from Aspergillus sp. HPL Y-30,212. Fermentation, isolation, characterization and biological properties.

Sood, Rattan; Roy, Karine; Reddy, G. C. S.; Reden, J.; Ganguli, B. N.

doi:10.7164/antibiotics.35.985

Cited by 4 publications

(5 citation statements)

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“…Some insights into the structure-activity-relations of this class of compounds are gained by comparing literature data of related compounds. Both 4-methoxy-2,5-toluquinone 4 [35] and 3-methoxy-2,5-toluquinone 5 [36] are more active, especially against S. aureus and B. subtilis than aurantiogliocladin. A study assessing a large number of 1,4-benzoquinones and 2,5-toluquinones demonstrated a low sensitivity of E. coli against almost all compounds while the sensitivity of S. aureus varied across the different compounds.…”

Section: Discussionmentioning

confidence: 97%

Aurantiogliocladin inhibits biofilm formation at subtoxic concentrations

Yuyama¹,

Neves²,

Memoria³

et al. 2017

AIMS Microbiology

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Infections where pathogens are organized in biofilms are difficult to treat due to increased antibiotic resistances in biofilms. To overcome this limitation new approaches are needed to control biofilms. One way is to screen natural products from organisms living in a wet environment. The rational is that these organisms are preferentially threatened by biofilm formation and may have developed strategies to control pathogens in these biofilms. In a screen of fungal isolates obtained from the Harz mountains in Germany several strains have been found producing compounds for the inhibition of biofilms. One of these strains has been identified as Clonostachys candelabrum producing aurantiogliocladin. Biological tests showed aurantiogliocladin as a weak antibiotic which was active against Staphylococcus epidermidis but not S. aureus . Aurantiogliocladin could also inhibit biofilm formation of several of the tested bacterial strains. This inhibition, however, was never complete but biofilm inhibition activity was also found at concentrations below the minimal inhibitory concentrations, e. g. Bacillus cereus with a MIC of 128 µg mL −1 showed at 32 µg mL −1 still 37% biofilm inhibition. In agreement with this finding was the observation that aurantiogliocladin was bacteriostatic for the tested bacteria but not bactericidal. Because several closely related toluquinones with different antibiotic activities have been reported from various fungi screening of a chemical library of toluquinones is suggested for the improvement of biofilm inhibition activities.

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Section: Discussionmentioning

confidence: 97%

Aurantiogliocladin inhibits biofilm formation at subtoxic concentrations

Yuyama¹,

Neves²,

Memoria³

et al. 2017

AIMS Microbiology

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“…s, 5.48s,6.55 s 2e ... . »-C6Hb 96 0.881(7.5), 1.08-1.75 m, 2.561 (7.5), 3.78s, 5.41 s,6.55 s 2f ... .…”

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confidence: 97%

“…s, 5.48s,6.55 s 2e ... . »-C6Hb 96 0.881(7.5), 1.08-1.75 m, 2.561 (7.5), 3.78s, 5.41 s,6.55 s 2f ... . Me2C=CHCH2 84 1.63 s, 1.71s, 3.23d(7.5), 3.76s, 5.221(7.5),5.48 s,6.53 s 2g .…”

mentioning

confidence: 97%

“…»-C6Hb 96 0.881(7.5), 1.08-1.75 m, 2.561 (7.5), 3.78s, 5.41 s,6.55 s 2f ... . Me2C=CHCH2 84 1.63 s, 1.71s, 3.23d(7.5), 3.76s, 5.221(7.5),5.48 s,6.53 s 2g . s, 3.90s, 5.56s, 6.53 s,7.15 s 'Values in CDC13 at 60 MHz; coupling constants (Hz) in parentheses.…”

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confidence: 99%

“…After clinical trial it was marketed in Brazil for the treatment of basal cell car-cinoma with excellent results (5). Two other antibiotics of the same structural type, la (6) and lb (7), have been isolated from fungi. In order to provide an easier access to those rather simple quiñones and to establish structure/activity relationships, we looked for a general, direct, and inexpensive synthesis for 6-alkyl-2-methoxy-1,4-benzoquinones la-lg.…”

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confidence: 99%

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Simple Synthesis of Primin and its Analogues via Lithiation of Protected Guaiacol

Bieber¹,

Chiappeta²,

Souza³

et al. 1990

J. Nat. Prod.

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and PEDRO ROLIM NETO Cuno dc Mettrado em C i e Fannaciutiu, Uniwsidad Federal& P e m a m h , 50.739 Raife, Pemambuco, BrazilABSTRACT.-A simple two-step synthesis of primin [Id] and related &substituted 2-methoxy-1,4-benzoquinones has been developed. Tetrahydropyranylated guaiacol [5] was treated with n-butyllithium followed by alkylation with alkyl, allyl, or benzyl bromides. Hydrolysis to the corresponding 6-substituted 2-methoxyphenols 2~2 g and subsequent oxidation catalyzed by salcomine afforded high yields of the quinones la-lg.Primin was identified in 1927 as the allergenic principle of Primula obconica (l), but its structure of 2-methoxy-6-npentyl-1,4-benzoquinone [la) was established only in 1967 by spectroscopic methods (2) and confirmed by synthesis (3). The same product was also found in the roots of a Brazilian tree, called "pau mondC" and now identified as Miconia eriodonta DC.; it revealed significant antimicrobial and antitumor activity (4). After clinical trial it was marketed in Brazil for the treatment of basal cell carcinoma with excellent results (5). Two other antibiotics of the same structural type, la (6) and l b (7), have been isolated from fungi. In order to provide an easier access to those rather simple quinones and to establish structurelactivity relationships, we looked for ageneral, direct, and inexpensive synthesis for 6-alkyl-2-methoxy-1,4-benzoquinones la-lg.Alkyl-substituted methoxyphenols 2-2g, 3a, and 3d seemed to be suitable precursors for our purposes (Scheme 1). 2a-2g t a: b: d: e: E C: I 0 la-lg OH 3a, 3d t

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Fungi a Potential Source of Bioactive Metabolites an Indian Prospective

Deshmukh

Kharwar

2021

Progress in Mycology

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3-Methoxy-2,5-toluquinone from Aspergillus sp. HPL Y-30,212. Fermentation, isolation, characterization and biological properties.

Cited by 4 publications

References 5 publications

Aurantiogliocladin inhibits biofilm formation at subtoxic concentrations

Aurantiogliocladin inhibits biofilm formation at subtoxic concentrations

Simple Synthesis of Primin and its Analogues via Lithiation of Protected Guaiacol

Fungi a Potential Source of Bioactive Metabolites an Indian Prospective

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