The Epoxy Group of Pramanicin Is Required for the Optimal Endothelium-Dependent Relaxation of Rat Aorta

Kwan, Chiu‐Yin; Zhang, Wenbo; Miller, J.D.; Harrison, Paul; Kassan, Salina; Liscombe, David K.

doi:10.1254/jphs.92.203

Cited by 6 publications

(8 citation statements)

References 13 publications

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“…In this case, the chemical shift difference between 3a-e and 10a (ca. 2ppm) was larger than for the difference between 6b-e, 8 and 12 (ca.…”

Section: Introductionmentioning

confidence: 73%

“…[10][11][12][13][14] There is no data related to its toxicity or mode of action. Other analogues of pramanicin (pramanicin A, TMC-260) are known, 8,15 and the isolation of the related virgaricin has been reported. 16 It has recently been recognised that existing strategies for the discovery of new antibacterials have not been effective, 17 probably as a result on over-reliance of combinatorial approaches leading to structurally narrow libraries, 18,19 and as a result there is an urgent need for the identification of novel leads for expanding the antibacterial drug development pipeline.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Mimics of Pramanicin from Pyroglutamic Acid and Their Antibacterial Activity

et al. 2015

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Epoxypyrrolidinones are available by epoxidation of carboxamide-activated bicyclic lactam substrates derived from pyroglutamate using aqueous hydrogen peroxide and tertiary amine catalysis. In the case of an activating Weinreb carboxamide, further chemoselective elaboration leads to the efficient formation of libraries of epoxyketones. Deprotection may be achieved under acidic conditions to give epoxypyroglutaminols, although the ease of this process can be ameliorated by the presence of internal hydrogen bonding. Bioassay against S. aureus and E. coli indicated that some compounds exhibit antibacterial activity. These libraries may be considered to be structural mimics of the natural products pramanicin and epolactaene. More generally, this outcome suggests that interrogation of bioactive natural products is likely to permit the identification of "privileged" structural scaffolds, providing frameworks suitable for optimization in a short series of chemical steps that may accelerate the discovery of new antibiotic chemotypes. Further optimization of such systems may permit the rapid identification of novel systems suitable for antibacterial drug development.

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“…In this case, the chemical shift difference between 3a-e and 10a (ca. 2ppm) was larger than for the difference between 6b-e, 8 and 12 (ca.…”

Section: Introductionmentioning

confidence: 73%

Section: Introductionmentioning

confidence: 99%

Synthesis of Mimics of Pramanicin from Pyroglutamic Acid and Their Antibacterial Activity

et al. 2015

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“…This compound is active against a number of fungi, including Cryptococcus neoformans . Pramanicin has also been found to disturb the vasorelaxation of dog carotid artery by selectively acting on the endothelial cells, causing relaxation through the endothelium-dependent nitric oxide pathway to activate endothelial nitric oxide synthase (169), and the epoxide is required for the optimal effects (170). It also activates caspases and induces apoptosis in Jurkat leukemia cells (171).…”

Section: αω-Sphingoids: “Two-headed” Sphingoid Base-like Compoundsmentioning

confidence: 99%

Thematic Review Series: Sphingolipids. Biodiversity of sphingoid bases (“sphingosines”) and related amino alcohols

Pruett

Bushnev

Hagedorn

et al. 2008

Journal of Lipid Research

415

341

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“Sphingosin” was first described by J. L. W. Thudichum in 1884 and structurally characterized as 2S,3R,4E-2-aminooctadec-4-ene-1,3-diol in 1947 by Herb Carter, who also proposed the designation of “lipides derived from sphingosine as sphingolipides.” This category of amino alcohols is now known to encompass hundreds of compounds that are referred to as sphingoid bases and sphingoid base-like compounds, which vary in chain length, number, position, and stereochemistry of double bonds, hydroxyl groups, and other functionalities. Some have especially intriguing features, such as the tail-to-tail combination of two sphingoid bases in the α,ω-sphingoids produced by sponges. Most of these compounds participate in cell structure and regulation, and some (such as the fumonisins) disrupt normal sphingolipid metabolism and cause plant and animal disease. Many of the naturally occurring and synthetic sphingoid bases are cytotoxic for cancer cells and pathogenic microorganisms or have other potentially useful bioactivities; hence, they offer promise as pharmaceutical leads. This thematic review gives an overview of the biodiversity of the backbones of sphingolipids and the broader field of naturally occurring and synthetic sphingoid base-like compounds.

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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: 56%

“…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. Virgaricin produced by Virgaria sp.…”

mentioning

confidence: 99%

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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The Epoxy Group of Pramanicin Is Required for the Optimal Endothelium-Dependent Relaxation of Rat Aorta

Cited by 6 publications

References 13 publications

Synthesis of Mimics of Pramanicin from Pyroglutamic Acid and Their Antibacterial Activity

Synthesis of Mimics of Pramanicin from Pyroglutamic Acid and Their Antibacterial Activity

Thematic Review Series: Sphingolipids. Biodiversity of sphingoid bases (“sphingosines”) and related amino alcohols

Virgaricin produced by Virgaria sp. FKI-4860

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