Pramanicin, a novel antimicrobial agent from a fungal fermentation

Schwartz, Robert E.; Helms, Gregory L.; Bolessa, E. A.; Wilson, Kenneth E.; Giacobbe, Robert A.; Tkacz, Jan S.; Bills, Gerald F.; Liesch, Jerrold M.; Zink, Deborah L.; Curotto, James E.; Pramanik, Barnali; Onishi, Janet C.

doi:10.1016/s0040-4020(01)80843-7

Tetrahedron

1994

DOI: 10.1016/s0040-4020(01)80843-7

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Pramanicin, a novel antimicrobial agent from a fungal fermentation

Robert E. Schwartz

Gregory L. Helms

E. A. Bolessa

et al.

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1994

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Cited by 77 publications

(73 citation statements)

References 14 publications

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“…The ROESY correlations between OH-4/H-8 and H-5/H-8 indicated that OH-4 and H-5 were located on the same face of the molecule. This was supported by the similarities of 13 C NMR data in CD 3 OD (Table 1) between 1 and pramanicins, 7,8 indicating the same relative configurations at C-3, C-4 and C-5. In consequence, the relative stereochemistry of 1 in the g-lactam moiety was assigned to be the same as for pramanicins.…”

mentioning

confidence: 59%

“…This compound was found to be an analog of pramanicins and TMC-260. [7][8][9] In this study, we describe the isolation, structure elucidation and antimicrobial activity of 1.Fungal strain FKI-4860 was isolated from a soil sample collected in the Bonin Islands, Tokyo, Japan. It is characterized by olive gray colonies, and solitary, mainly reniform and light brown sympodial conidia.…”

mentioning

confidence: 99%

“…This compound was found to be an analog of pramanicins and TMC-260. [7][8][9] In this study, we describe the isolation, structure elucidation and antimicrobial activity of 1.…”

mentioning

confidence: 99%

“…However, pramanicin exhibits potent antifungal activity against a variety of fungal pathogens, including C. albicans and Cryptococcus neoformans, as well as antibacterial activity against B. subtilis. 7,12 Pramanicin has also been reported to cause endothelialdependent relaxation of rat aorta, although the activity of pramanicin A (in which the causative epoxide group was changed to a double bond) was weak. 13 While pramanicin's side-chains have two more carbons than 1, the side-chain carbon number of TMC-260, an IL-4 signal transduction inhibitor produced by Acremonium kiliense, 9 was the same as that of 1.…”

mentioning

confidence: 99%

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Virgaricin produced by Virgaria sp. FKI-4860

et al. 2012

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The genus Virgaria was first proposed in 1817 1 and classified in the family Xylariaceae. 2 Virgaria nigra, a type species of Virgaria, is a commonly encountered hyphomycetes and has been illustrated in numerous publications. [3][4][5] However, little work has been done on the chemical constituents of Virgaria species, and only one compound, vinigrol, has previously been isolated from V. nigra. 6 As part of our interest in the presence of novel metabolites in Virgaria sp., we investigated the chemical constituents of a culture broth of a newly discovered Virgaria sp. FKI-4860 that resulted in the isolation of a new compound, virgaricin (1). This compound was found to be an analog of pramanicins and TMC-260. [7][8][9] In this study, we describe the isolation, structure elucidation and antimicrobial activity of 1.Fungal strain FKI-4860 was isolated from a soil sample collected in the Bonin Islands, Tokyo, Japan. It is characterized by olive gray colonies, and solitary, mainly reniform and light brown sympodial conidia. The rDNA internal transcribed spacer (ITS) sequence of strain FKI-4860 was elucidated and deposited at the DNA Data Bank of Japan, with the accession number AB670709. With respect to sequence distances elucidated by the MegAlign programs from the Lasergene 9 package (DNAStar Inc., Madison, WI, USA), FKI-4860 had 90% similarity with the ITS sequences of V. nigra CBS 525.69 (AB670712). From the results of morphological characteristics and sequence analysis, strain FKI-4860 was identified as a novel species of Virgaria. 10 Strain FKI-4860 was grown and maintained on a LcA slant consisting of 0.1% glycerol, 0.08% KH 2 PO 4 , 0.02% K 2 HPO 4 , 0.02% MgSO 4 Á7H 2 O, 0.02% KCl, 0.2% NaNO 3 , 0.02% yeast extract and 1.5% agar (adjusted to pH 6.0 before sterilization). A loop of spores of Virgaria sp. FKI-4860 was inoculated into 10 ml of seed medium, which consisted of 2.0% glucose, 0.2% yeast extract, 0.5% Polypepton (Wako Pure Chemical Industries, Osaka, Japan), 0.05% MgSO 4 Á7H 2 O, 0.1% KH 2 PO 4 and 0.1% agar (adjusted to pH 6.0 before sterilization), in a test tube. The inoculated tube was incubated on a rotary shaker (300 r.p.m.) at 27 1C for 3 days.

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mentioning

confidence: 59%

mentioning

confidence: 99%

“…This compound was found to be an analog of pramanicins and TMC-260. [7][8][9] In this study, we describe the isolation, structure elucidation and antimicrobial activity of 1.…”

mentioning

confidence: 99%

mentioning

confidence: 99%

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Virgaricin produced by Virgaria sp. FKI-4860

et al. 2012

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“…Since they have specific and potent inhibitory actions on sarcoplasmic recticulum Ca 2+ -ATPase, they are now widely used as pharmacological tools for studying the regulation of cell Ca 2+ (6 -9) Recently, a potent antifungal agent, pramanicin (see Fig. 1 for chemical structure), with a highly functionalized polar head group and a simple, long aliphatic side chain was isolated from a fungal fermentation (10) and biosynthesized (11). Pramanicin exerts a potent anti-growth effect on a wide range of fungal organisms with minimal inhibitory concentrations (MIC) of 20 -100 mM (10).…”

mentioning

confidence: 99%

Vasorelaxant Effects of Pramanicin, an Anti-fungal Agent: Selective Action on Endothelial Cells

Kwan¹,

Harrison

Duspara

et al. 2001

Japanese Journal of Pharmacology

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ABSTRACT-A newly discovered antifungal agent, pramanicin, within the therapeutically effective concentration range (4 -100 mM), inhibits the tone of phenylephrine (PE)-precontracted dog carotid arterial rings in a concentration-dependent manner and leads to gradual development of relaxation. However, pramanicin had no effect on rings precontracted with 100 mM KCl or on endothelium-denuded rings. Thus, inhibition by pramanicin of PE-induced contraction was endothelium-dependent. Preincubation of 100 mM pramanicin with carotid arterial rings for 30 min did not significantly affect the concentration-contraction response to PE, but almost completely inhibited the endothelium-dependent relaxation response to subsequent addition of 3 m M carbachol or 100 m M pramanicin. This irreversible inhibition of endotheliumdependent relaxation, which is independent of extracellular Ca 2+, suggests possible endothelial cell damage by pramanicin. Pretreatment of the endothelium-intact vascular rings with L-N G -nitro-arginine (100 mM) inhibited the relaxation of PE-precontracted rings induced by 3 mM carbachol or 100 mM pramanicin, suggesting that the generation of nitric oxide (NO) in endothelial cells mediates the slow vascular relaxation induced by pramanicin. We conclude that pramanicin has little direct effect on the contractility of smooth muscle cells, but causes an initial slow endothelium-dependent, NO-mediated vascular relaxation. This is followed by a cytotoxic effect on vascular endothelial cells, eventually resulting in the loss of vasorelaxant function.Keywords: Antifungal agent, Pramanicin, Endothelial cell, Nitric oxide, Vascular smooth muscle Antifungal agents are widely used not only in human and veterinary medicine, but are also applied as disinfectants or preservatives in industrial environments where control of fungal growth is desirable. One class of antifungal compounds, having the general structure of a polar, highly functionalized head group and a simple fatty acid side chain (1 -5), act through a variety of mechanisms including the inhibition of sterol biosynthesis, sphingofungin formation and cell wall generation. However, the actions and toxicities of such agents in mammals have not been systematically studied. Indeed, some potent antimicrobial agents exhibit high levels of toxicity and have limited therapeutic value when used systemically, such as cyclopiazonic acid and thapsigargin. Since they have specific and potent inhibitory actions on sarcoplasmic recticulum Ca 2+ -ATPase, they are now widely used as pharmacological tools for studying the regulation of cell Ca 2+ (6 -9) Recently, a potent antifungal agent, pramanicin (see Fig. 1 for chemical structure), with a highly functionalized polar head group and a simple, long aliphatic side chain was isolated from a fungal fermentation (10) and biosynthesized (11). Pramanicin exerts a potent anti-growth effect on a wide range of fungal organisms with minimal inhibitory concentrations (MIC) of 20 -100 mM (10). Despite the suggestion of various clinical app...

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Asymmetric α‐Hydroxylation of β‐Indanone Esters and β‐Indanone Amides Catalyzed by C‐2′ Substituted Cinchona Alkaloid Derivatives

et al. 2016

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Theh ighly catalytic asymmetric a-hydroxylation of b-indanone esters and b-indanone amides using peroxide as the oxidant was realized with an ew C-2' substituted Cinchona alkaloid derivatives. Thet wo enantiomers of a-hydroxy-b-indanone esters could be obtained by simply changing the oxidant. This protocola llows ac onvenient access to the corresponding a-hydroxy-b-indanone esters and a-hydroxy-b-indanone amides with up to 99% yield and 98% ee.

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Pramanicin, a novel antimicrobial agent from a fungal fermentation

Cited by 77 publications

References 14 publications

Virgaricin produced by Virgaria sp. FKI-4860

Virgaricin produced by Virgaria sp. FKI-4860

Vasorelaxant Effects of Pramanicin, an Anti-fungal Agent: Selective Action on Endothelial Cells

Asymmetric α‐Hydroxylation of β‐Indanone Esters and β‐Indanone Amides Catalyzed by C‐2′ Substituted Cinchona Alkaloid Derivatives

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