The structure op beauvericin, a new depsipeptide antibiotic toxic to

Hamill, Robert L.; Higgens, C. E.; Boaz, Harold E.; Gorman, Marvin

doi:10.1016/s0040-4039(01)88668-8

Cited by 360 publications

(225 citation statements)

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“…The active fractions were collected and the solvent was evaporated. The further purification for decolorization was carried out by silica gel column chromatography (3ϫ5 cm) eluted with the mixed solvent of CHCl 3 and MeOH (10 : 1). The labeled anthranilic acid was obtained by the yield of 1.53 g (80% from Cu 13 CN).…”

Section: Copper (I) [ 13 C]cyanidementioning

confidence: 99%

“…In the conversion process to isoleucine, the bond derived from the C 2 unit is not cleaved and subsequently constitutes the C b and C g -CH 3 in isoleucine molecule. Because a pyruvate molecule is synthesized from a glucose molecule, the block of C b and C g -CH 3 should be labeled by 13 C simultaneously or not labeled at all in an isoleucine molecule. In the same manner, the simultaneously labeled blocks derived from a single glucose molecule should be found at C a -C co and C g -CH 2 -C d .…”

Section: Incorporation Of D-[u-13 C]glucose To Quinolactacin Amentioning

confidence: 99%

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Biosynthesis of Quinolactacin A, a TNF Production Inhibitor

et al. 2006

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Quinolactacins, which inhibit tumor necrosis factor production, contain a quinolone skeleton conjugated with a g -lactam. The biosynthesis of quinolactacin was investigated by feeding experiments using 13 Keywords quinolactacin, quinolone, biosynthesis, 13 C labeled precursor, Penicillium sp. IntroductionSince entomopathogenic fungi possess a parasitic function, it was expected that novel biologically active compounds such as insecticides and immunosuppressants would be isolated from them [1ϳ7]. In the course of an HPLC-based, chemical screening program of the metabolites of entomopathogenic fungi, the novel pyridone alkaloids, pyridovericin and pyridomacrolidin, possessing protein kinase inhibitory activity, were isolated from the cultured broth of Beauveria bassiana 9]. In addition, novel quinolone alkaloids, quinolactacins A (1), B (2), and C (3) were obtained from the cultured broth of Penicillium sp. EPF-6, which was isolated from the larvae of the mulberry pyralid (Margaronia pyloalis Welker) [10]. Alkaloid 1, the major constituent, exhibited inhibitory activity against tumor necrosis factor (TNF) production by murine macrophages and macrophage-like J774.1 cells stimulated with lipopolysaccharide (LPS).Quinolactacins have a unique quinolone skeleton conjugated with a g-lactam ring [11], as shown in Figure 1. Subsequently, Kim et al., reported the characterization of stereoisomers of 1 through a screening program for inhibitors of acetylcholinesterase [12], and Tatsuta's group reported the biomimetic synthesis of quinolactacin B (2) using acetic acid, valine, and anthranilic acid [13]. In this paper, the biosynthesis of 1 was studied by feeding experiments using several 13 C single-labeled precursors and D-[U-

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Section: Copper (I) [ 13 C]cyanidementioning

confidence: 99%

Section: Incorporation Of D-[u-13 C]glucose To Quinolactacin Amentioning

confidence: 99%

Biosynthesis of Quinolactacin A, a TNF Production Inhibitor

et al. 2006

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“…Beauvericin is toxic to brine shrimp and to the larvae of insects, 16,21 and acts as an important virulence factor during insect pathogenesis by B. bassiana. 22 It also displays moderate antifungal activity, and antibiotic activity against Gram-positive bacteria.…”

Section: Cyclohexadepsipeptides: Beauvericinmentioning

confidence: 99%

“…22 It also displays moderate antifungal activity, and antibiotic activity against Gram-positive bacteria. 21 Beauvericin is a low-micromolar inhibitor of acyl CoA:cholesterol acyltransferase (ACAT, EC 2.3.1.26): inhibition of this enzyme leads to decreased plasma cholesterol levels. 23,24 ACAT inhibition also suppresses proteolytic processing of the b-amyloid precursor protein, thereby reducing amyloid plaque density in animal models of Alzheimer's disease.…”

Section: Cyclohexadepsipeptides: Beauvericinmentioning

confidence: 99%

Fungal cyclooligomerdepsipeptides: From classical biochemistry to combinatorial biosynthesis

et al. 2011

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“…They are composed of an alternating sequence of three N-methyl-L-amino acids and three D-a-hydroxyisovaleric acids. 6,16,17 Mixtures of ENs B, EN B 1 and A previously showed anti-HIV-1 activity by protecting human lymphoblastoid cells against HIV-1-induced cell death with an in vitro therapeutic index of approximately 200. 5 Our group has copurified BEA, and ENs H, I and MK1688 from culture broth of F. oxysporum, and the production of these cyclic hexadepsipeptides were further characterized during fermentation (Figure 2).…”

Section: Production Of Cyclic Hexadepsipeptides and Their Identificationmentioning

confidence: 99%

Beauvericin and enniatins H, I and MK1688 are new potent inhibitors of human immunodeficiency virus type-1 integrase

Shin

Song

et al. 2009

J Antibiot

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Some enniatins (ENs) reportedly exhibit antiretroviral activities in vivo. The potential inhibitory activities of cyclic hexadepsipeptides such as beauvericin (BEA) and ENs H, I and MK1688 were investigated in vitro against human immunodeficiency virus type-1 (HIV-1) integrase and Moloney murine leukemia virus reverse transcriptase. BEA, EN I and EN MK1688 exhibited strong inhibitory activities against HIV-1 integrase, whereas EN H showed relatively weak activity. None of the examined compounds showed anti-reverse transcriptase activity. BEA was the most effective inhibitor of the tested cyclic hexadepsipeptides in inhibiting HIV-1 integrase. These results indicate the potential of cyclic hexadepsipeptides as a new class of potent inhibitors of HIV-1 integrase.

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The structure op beauvericin, a new depsipeptide antibiotic toxic to

Cited by 360 publications

References 1 publication

Biosynthesis of Quinolactacin A, a TNF Production Inhibitor

Biosynthesis of Quinolactacin A, a TNF Production Inhibitor

Fungal cyclooligomerdepsipeptides: From classical biochemistry to combinatorial biosynthesis

Beauvericin and enniatins H, I and MK1688 are new potent inhibitors of human immunodeficiency virus type-1 integrase

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