Circumdatin G, a New Alkaloid from the Fungus <i>Aspergillus ochraceus</i>

Dai, Jin-Rui; Carté, Brad; Sidebottom, Philip J.; Yew, Alex Lee Sek; Ng, Siewbee; Huang, Yunsong; Butler, Mark S.

doi:10.1021/np000381u

Cited by 111 publications

(75 citation statements)

References 11 publications

(23 reference statements)

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“…This suggests that the inhibitory effect of the fraction against S. hyicus is mediated by the combined activity of micromolide and (R)-(-)-mellein. Hence, our own results and previous reports (22,(36)(37)(38)(39) suggest that the specific combination of antimicrobials present in the larval secretion of A. compressa exert activity against a wide range of different microbes.…”

Section: Discussionsupporting

confidence: 72%

“…It has been shown to have antibacterial activity against standard and methicillin-resistant strains of Staphylococcus aureus (36). Moreover, it has antifungal activity (37,38) and is a potent inhibitor of hepatitis C virus protease NS3 (39). However, to our knowledge, (R)-(-)-mellein has never been reported before as an antimicrobial agent used by an insect.…”

Section: Discussionmentioning

confidence: 94%

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Larvae of the parasitoid wasp Ampulex compressa sanitize their host, the American cockroach, with a blend of antimicrobials

Herzner

Schlecht

Dollhofer

et al. 2013

Proc. Natl. Acad. Sci. U.S.A.

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Food resources contaminated with spoilage or pathogenic microorganisms pose severe problems to all higher organisms. Here, we describe a food-hygienic strategy of the emerald cockroach wasp Ampulex compressa . The wasp larvae develop on and inside the American cockroach Periplaneta americana , a host that can harbor various putrefactive microbes, as well as human and insect pathogens. From P. americana , we isolated the Gram-negative bacterium Serratia marcescens , which is a potent entomopathogen that can rapidly kill insect larvae. It is also known as a food contaminant and as an opportunistic human pathogen. Using behavioral observations and chemical analyses, we demonstrated that A. compressa larvae impregnate their cockroach hosts from inside with large amounts of an oral secretion containing a blend of γ-lactones and isocoumarins with ( R )-(-)-mellein [( R )-(-)-3,4-diydro-8-hydroxy-3-methylisocoumarin] and micromolide [(4 R ,9 Z )-octadec-9-en-4-olide] as dominant components. We fractionated hexane extracts of the secretion and investigated the antimicrobial properties of the fraction containing the lactones and isocoumarins, as well as of synthetic ( R )-(-)-mellein and micromolide, against S. marcescens and a Gram-positive bacterium, Staphylococcus hyicus , in broth microdilution assays. The test fraction inhibited growth of both tested bacteria. The activity of the fraction against S. marcescens was explained by ( R )-(-)-mellein alone, and the activity against S. hyicus was explained by the combined action of ( R )-(-)-mellein and micromolide. Our data suggest that the specific combination of antimicrobials in the larval secretion provides an effective frontline defense against the unpredictable spectrum of microbes that A. compressa larvae may encounter during their development inside their cockroach hosts.

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Section: Discussionsupporting

confidence: 72%

Section: Discussionmentioning

confidence: 94%

Larvae of the parasitoid wasp Ampulex compressa sanitize their host, the American cockroach, with a blend of antimicrobials

Herzner

Schlecht

Dollhofer

et al. 2013

Proc. Natl. Acad. Sci. U.S.A.

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“…While the carboxyterminal group of NS3 provides helicase function, its amino terminal group exhibits protease activity. Mellein, a compound isolated from the fungus Aspergillus ochraceus, exhibits anti-HCV protease activity with an IC50 value of 35 µmol/L [28] . Testing the effects of various pseudoguaianolides from Parthenium hispitum in an HCV subgenomic replicon system revealed anti-HCV activities of many compounds.…”

Section: -Arylbenzofuran Derivativesmentioning

confidence: 99%

Natural products as promising drug candidates for the treatment of hepatitis B and C

Wohlfarth

Efferth

2008

Acta Pharmacol Sin

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Hepatitis B virus (HBV) or hepatitis C virus (HCV) infections are a major threat worldwide. Combination therapy of interferon-α and ribavirin is currently the treatment of choice for HCV-infected patients. However, this regimen is only effective in approximately 50% of patients and provokes severe side-effects. Numerous natural alternatives for treating HCV have been suggested. Deoxynojirimycin and its derivatives are iminosugars which exert anti-HCV activity by inhibiting α-glucosidases. A non-immunosuppressive derivate of cyclosporine A, NIM811, exerts anti-HCV activity by binding to cyclophilin. Other natural products with promising anti-HCV activity are 2-arylbenzofuran derivatives, Mellein, and pseudoguaianolides. For HBV treatment, several drugs are available, specifically targeting the virus polymerase (lamivudine, entecavir, telbivudine, and adefovir dipivoxil). The efficacy of these drugs is hampered by the development of resistance due to point mutations in the HBV polymerase. Due to drug resistance and adverse side-effects, the search for novel drugs is mandatory. Wogonin, ellagic acid, artemisinin and artesunate, chrysophanol 8-O-β-D-glucoside, saikosaponin C, and protostane triterpenes are active against HBV. Natural products need to be investigated in more detail to explore their potential as novel adjuncts to established HBV or HCV therapy.

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“…The structure of 1 was determined by comparison of its 1 H NMR and 13 C NMR spectral data (Table 1) with those of other known circumdatins, especially 2, and was confirmed by 2D NMR experiments (COSY H-H, HSQC and HMBC) [7,9]. According to the spectral data of 1, this compound presented a benzodiapezine structure derived from proline and anthranilic acid joined to another anthranilic acid unit, as in 2 and circumdatin D (5).…”

Section: Resultsmentioning

confidence: 77%

Circumdatin H, a New Inhibitor of Mitochondrial NADH Oxidase, from Aspergillus ochraceus

et al. 2005

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Circumdatin H (1), a new alkaloid from the culture broth of Aspergillus ochraceus, has been isolated, together with a known circumdatin, circumdatin E (2) and other known compounds: flavacol (3) and stephacidin A (4). The structure of 1 was established on the basis of chemical and spectral evidence. All of these alkaloids showed biological activity as inhibitors of the mammalian mitochondrial respiratory chain.

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Circumdatin G, a New Alkaloid from the Fungus Aspergillus ochraceus

Cited by 111 publications

References 11 publications

Larvae of the parasitoid wasp Ampulex compressa sanitize their host, the American cockroach, with a blend of antimicrobials

Larvae of the parasitoid wasp Ampulex compressa sanitize their host, the American cockroach, with a blend of antimicrobials

Natural products as promising drug candidates for the treatment of hepatitis B and C

Circumdatin H, a New Inhibitor of Mitochondrial NADH Oxidase, from Aspergillus ochraceus

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