Identification of the inhibitory activity of carbazomycins B and C against 5-lipoxygenase, a new activity for these compounds.

Hook, Derek J.; Yacobucci, Joseph J.; O'Connor, S. E.; Lee, Mike; Kerns, Ed; Krishnan, Bala; Matson, Jim; Hesler, Grace A.

doi:10.7164/antibiotics.43.1347

Cited by 54 publications

(30 citation statements)

References 3 publications

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“…A t this concentration LTC4 synthesis was significantly in hibited by 1 -3 (Table III). The influence of 2 and 3 on the 5-lipoxygenase (5-LOX) of RBL-1 cells was tested in a cell free extract (Hook et al, 1990). No inhibition could be observed at concentrations up to 50 (.ig/ml.…”

Section: Biological Propertiesmentioning

confidence: 99%

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(+)-10α-Hydroxy-4-muurolen-3-one, a New Inhibitor of Leukotriene Biosynthesis from a Favolaschia Species. Comparison with Other Sesquiterpenes

Zapf¹,

Wunder²,

Anke³

et al. 1996

Zeitschrift Für Naturforschung C

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A new inhibitor of leukotriene biosynthesis, (+)-10a-hydroxy-4-muurolen-3-one (1), was isolated from fermentations of Favolaschia sp. 87129. Its structure was established by spectro scopic methods. The compound exhibited no antifungal or antibacterial activities.The effects of 1 on leukotriene biosynthesis were compared with (+)-T-cadinol, (-)-3-oxo-T-cadinol, and (+)-3a-hydroxy-T-cadinol, three related sesquiterpenes.

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Section: Biological Propertiesmentioning

confidence: 99%

“…5-Lipoxygenase-assay: The 5-lipoxygenase activ ity was determ ined in the cytosolic 13000 x g frac tion of broken RBL-1 cells according to Hook et al (1990) with modifications: The content of 5-hydroxyeicosatetraenoic acid was quantified by re versed phase HPLC using a 0.1% aqueous H 3P 0 4/ acetonitrile gradient.…”

Section: Tests Fo R Biological Activitiesmentioning

confidence: 99%

(+)-10α-Hydroxy-4-muurolen-3-one, a New Inhibitor of Leukotriene Biosynthesis from a Favolaschia Species. Comparison with Other Sesquiterpenes

Zapf¹,

Wunder²,

Anke³

et al. 1996

Zeitschrift Für Naturforschung C

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“…BU-4601 A, B and C exhibited essentially the same UVabsorption maxima at 220, 246 (sh) and Table 1 UV Amax nm (8) 360 nm, indicating that three components possessed the same chromophore moiety. The IR spectrum of BU-4601 C (Fig.…”

Section: Structural Determinationmentioning

confidence: 89%

“…The «-propyl derivative (5) was prepared from the acid by reaction with w-propanol in the presence of SOC12. «-Hexyl (6), «-nonyl (7) and w-lauryl 5-hydroxyanthranilates (8) were synthesized by condensation of diCbz-5-hydroxyanthranilic acid with H-hexyl, «-nonyl and w-lauryl alcohols, respectively, in dried DMFusing dicyclohexylcarbodiimide and pyridine followed by hydrogenolysis in the presence of palladium black. Physico-chemical data of these synthetic derivatives are described in the Experimental section.…”

Section: Structural Determinationmentioning

confidence: 99%

“…Purification was performed by preparative TLC («-hexane -acetone, 10 : 1) followed by Sephadex LH-20 chromatography with CH2Cl2 -MeOH(4 : 6) to afford 6 (15mg) as a white amorphous powder. TLC Rf «-Nonyl 5-Hydroxyanthranilate (7) Except that the w-hexyl alcohol was replaced by w-nonyl alcohol (2 ml), the same procedure as employed for synthesis of 6 was repeated yielding a white amorphous powder of 7 (14mg H-Lauryl 5-Hydroxyanthranilate (8) w-Lauryl alcohol (1 ml) was reacted following to the same procedure as employed for the synthesis of 6 yielding a white amorphous powder of 8 (5mg). TLC Rf 0.53 (w-hexane-acetone, …”

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confidence: 99%

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5-Hydroxyanthranilic acid derivatives as potent 5-lipoxygenase inhibitors.

et al. 1993

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Three new 5-lipoxygenase inhibitors, designated as BU-4601 A, B and C, were found in the fermentation broth of Streptomyces sp. strain No. AA2807.Their structures were identified as isodecyl, isoundecyl and isolauryl esters of 5-hydroxyanthranilic acid, respectively. Based on their structures, five related esters were synthesized and evaluated for biological activity as inhibitors of 5-lipoxygenase. Both naturally-occurring and chemically-synthesized compoundsexhibited almost equal levels of 5-lipoxygenase inhibibory activities in vitro.5-Lipoxygenase catalyzes the first step in the metabolic conversion of arachidonic acid into the leukotrienes which are powerful mediators of a broad range of physiological responses. Novel inhibitors of 5-lipoxygenase offer potentially useful therapeutic agents for the treatment of various diseases such as rheumatoid arthritis, ulcerative colitis, psoriasis, and asthma1>2). In the course of a screening program for 5-lipoxygenase inhibitors, a streptomycete (strain No. AA2807), isolated from a soil sample collected in Nagatoro, Saitama Prefecture, Japan, was found to produce three active compounds designated as BU-460 1 A, B and C. Each component was isolated in a pure form by conventional column chromatography followed by preparative HPLC. The structures of BU-4601 A, B and C were determined by spectral analyses to be isodecyl, isoundecyl and isolauryl-5-hydroxyanthranilates, respectively. Based on these active lead compounds, five esters of 5-hydroxyanthranilic acid were synthesized. This paper deals with the production, isolation and structure determination of BU-4601 A, B and C, and 5-lipoxygenase inhibitory activities of three naturally-occurring and five chemically-synthesized derivatives of 5-hydroxyanthranilic acid.

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Carbazoles and Acridines

Gruner

Knölker

2011

Heterocycles in Natural Product Synthesis

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Identification of the inhibitory activity of carbazomycins B and C against 5-lipoxygenase, a new activity for these compounds.

Cited by 54 publications

References 3 publications

(+)-10α-Hydroxy-4-muurolen-3-one, a New Inhibitor of Leukotriene Biosynthesis from a Favolaschia Species. Comparison with Other Sesquiterpenes

(+)-10α-Hydroxy-4-muurolen-3-one, a New Inhibitor of Leukotriene Biosynthesis from a Favolaschia Species. Comparison with Other Sesquiterpenes

5-Hydroxyanthranilic acid derivatives as potent 5-lipoxygenase inhibitors.

Carbazoles and Acridines

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