Aranorosin, a novel antibiotic from Pseudoarachiniotus roseus. I. Taxonomy, fermentation, isolation, chemical and biological properties.

Roy, Kamalika; Mukhopadhyay, T.; Reddy, G. C. S.; Desikan, K. R.; Rupp, Richard H.; Ganguli, B. N.

doi:10.7164/antibiotics.41.1780

Cited by 24 publications

(11 citation statements)

References 15 publications

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“…Reduction of Aranorosin (3) to Aranorosinol A (1) To aranorosin (3) (lOOmg, 0.24mmol) in THF (5ml), sodium borohydride (9.4mg, 0.25mmol) was Aranorosinol B Diacetate (7)…”

Section: Methodsmentioning

confidence: 99%

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Aranorosinol A and aranorosinol B, two new metabolities from Pseudoarachniotus roseus: Production, isolation, structure elucidation and biological properties.

Mukhopadhyay¹,

Bhat²,

Roy³

et al. 1992

J. Antibiot.

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Two new secondary metabolites, aranorosinol A (1) and aranorosinol B (2), were isolated from a strain of Pseudoarachniotus roseus. Their structures were elucidated on the basis of their spectral properties and chemical transformations and were found to be similar to aranorosin (3) isolated from the samestrain.We have recently isolated two new metabolites, aranorosinol A (1) and aranorosinol B (2), from the fungal strain Y-30499 identified as Pseudoarachniotus roseus. Herein we report the isolation, structure elucidation and biological properties of these two metabolites. Compounds1 and 2 are structurally related to aranorosin (3) which was isolated earlier from the same fungal strain1~3). FermentationFermentation was carried out in shake flasks as well as in laboratory fermenters using the methods and conditions reported earlierX). The progress of the fermentation was monitored by the agar diffusion assay using Bacillus subtilis as the test strain. The antibiotics were present in both the culture filtrate and the mycelial cake. IsolationThe culture filtrate (40 liters) was extracted with ethyl acetate (2 x 15 liters). The mycelial cake (3.7 kg) Dedicated to Prof. Ch. Bheemasankara Rao of Andhra University on the occasion of his 60th birthday.

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“…Reduction of Aranorosin (3) to Aranorosinol A (1) To aranorosin (3) (lOOmg, 0.24mmol) in THF (5ml), sodium borohydride (9.4mg, 0.25mmol) was Aranorosinol B Diacetate (7)…”

Section: Methodsmentioning

confidence: 99%

“…Aranorosinol A (1) Aranorosinol A (1), C23H35NO6, differs from 3 in having two additional hydrogens in the molecule. Spectra were taken at 22.5 MHzusing 50mg/ml concentrations and the assignments of 1 and 2 were based on comparison with those reported for aranorosin (3).…”

Section: Isolationmentioning

confidence: 99%

Aranorosinol A and aranorosinol B, two new metabolities from Pseudoarachniotus roseus: Production, isolation, structure elucidation and biological properties.

Mukhopadhyay¹,

Bhat²,

Roy³

et al. 1992

J. Antibiot.

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“…Aranorosin has an alkyl chain similar to that of biverlactones. 7,8 This suggests that the alkyl chain has an important role in the inhibition activity against AAC(6 0 )/ APH(2 00 ). It was reported that ABK retained antimicrobial activity after enzymatic acetylation by AAC(3), AAC(2 0 ) and AAC(6 0 ).…”

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confidence: 99%

“…The structure of aranorosin was identified by comparison of its spectral data with those reported in literature. 8 Aranorosin showed no anti-MRSA activity at 0.3 mg per 6 mm disc on the MHA plate, but showed anti-MRSA activity (10 mm inhibition zone) on an MHA plate containing ABK (8 mg ml À1 ). The circumventing effect of aranorosin on the activity of ABK against MRSA was investigated by the agar dilution method (Table 1).…”

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Aranorosin circumvents arbekacin-resistance in MRSA by inhibiting the bifunctional enzyme AAC(6′)/APH(2″)

et al. 2012

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Oxidation of Phenolic Compounds with Organohypervalent Iodine Reagents

Moriarty

Prakash

2001

Organic Reactions

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The oxidation of phenols is a key biochemical process in oxidative phosphorylation, and it is also important in numerous biosynthetic pathways. Controlled oxidative transformations of substituted phenols are found in many synthetic organic sequences. Accordingly, a large number of oxidizing agents for phenols have been developed. Useful reagents include Fremy's salt (KSO 3 ) 2 NO,and a wide variety of other redox metal‐based oxidants such as Pb(IV), Mn(III), Tl(III), Cu(II), and Fe(III). Recently, organohypervalent iodine reagents have emerged as particularly useful agents for oxidizing phenols. In the area of natural product synthesis, organohypervalent iodine reagents have been used extensively to effect oxidative intramolecular bicyclization and spirocyclization. The focus of this chapter is on synthetic applications. The chapter also covers formation and applications of phenolic iodonium ylides. The processes that occur during the oxidation of phenols with organohypervalent iodine reagents can be divided into two categories. The first category involves ligand exchange of the phenolic proton with the hypervalent iodine reagent to generate the O‐I(III) intermediate, which is subsequently transformed to various products, depending upon the reaction conditions. These transformations include oxidation of phenols to quinones and related compounds, formation of spirocyclic and oxygen heterocyclic compounds via oxidative intramolecular participation reactions, and intramolecular carbon‐carbon bond formation via phenolic oxidative coupling. All of these reactions are driven by the reduction of iodine(III) [or iodine(V)] to iodine(I) (iodobenzene). A second class of reactions that is discussed in this chapter includes formation of stable iodonium salts and ylides, which are important intermediates in organic synthesis. These reactions occur via carbon‐I(III) bond formation without loss of iodobenzene.

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Aranorosin, a novel antibiotic from Pseudoarachiniotus roseus. I. Taxonomy, fermentation, isolation, chemical and biological properties.

Cited by 24 publications

References 15 publications

Aranorosinol A and aranorosinol B, two new metabolities from Pseudoarachniotus roseus: Production, isolation, structure elucidation and biological properties.

Aranorosinol A and aranorosinol B, two new metabolities from Pseudoarachniotus roseus: Production, isolation, structure elucidation and biological properties.

Aranorosin circumvents arbekacin-resistance in MRSA by inhibiting the bifunctional enzyme AAC(6′)/APH(2″)

Oxidation of Phenolic Compounds with Organohypervalent Iodine Reagents

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