Ascochlorin: A terpenoid metabolite from Acremonium luzulae

Cagnoli-Bellavita, Nera; Ceccherelli, Paolo; Fringuelli, Renata; Ribaldi, M.

doi:10.1016/0031-9422(75)83041-x

Cited by 18 publications

(14 citation statements)

References 4 publications

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“…However, the ascofuranone-producing fungal isolate was recently reexamined and identified as Acremonium sclerotigenum [58]. This species identification is consistent with previous reports on the occurrence of natural analogs of ascofuranone in several fungal taxa related to Acremonium , such as Colletotrichum , Cylindrocladium , Fusarium and Verticillium in Sordariomycetes [59,60,61,62,63]. Thus, the production of ascofuranone and ascochlorin by A. viciae has to be carefully re-examined.…”

Section: Biological Activities and The Modes Of Actionsupporting

confidence: 82%

Phytotoxic Metabolites Produced by Legume-Associated Ascochyta and Its Related Genera in the Dothideomycetes

Kim

Chen

2019

Toxins

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Phytotoxins, secondary metabolites toxic to plants and produced by fungi, are believed to play an important role in disease development by targeting host cellular machineries and/or interfering with host immune responses. The Ascochyta blight diseases on different legume plants are caused by Ascochyta and related taxa, such as Phoma. The causal agents of the Ascochyta blight are often associated with specific legume plants, showing a relatively narrow host range. The legume-associated Ascochyta and Phoma are known to produce a diverse array of polyketide-derived secondary metabolites, many of which exhibited significant phytotoxicity and have been claimed as virulence or pathogenicity factors. In this article, we reviewed the current state of knowledge on the diversity and biological activities of the phytotoxic compounds produced by Ascochyta and Phoma species. Also, we touched on the secondary metabolite biosynthesis gene clusters identified thus far and discussed the role of metabolites in the fungal biology.

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Section: Biological Activities and The Modes Of Actionsupporting

confidence: 82%

Phytotoxic Metabolites Produced by Legume-Associated Ascochyta and Its Related Genera in the Dothideomycetes

Kim

Chen

2019

Toxins

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“…[10], Cylindrocladium sp. [11], Cylindrocladium ilicicola MFC-870 [12, 13], Acremonium luzulae [14], and Verticillium sp. [15].…”

Section: Introductionmentioning

confidence: 99%

Ascochlorin is a novel, specific inhibitor of the mitochondrial cytochrome bc1 complex

Berry

Huang

Lee

et al. 2010

Biochimica et Biophysica Acta (BBA) - Bioenergetics

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Ascochlorin is an isoprenoid antibiotic that is produced by the phytopathogenic fungus Ascochyta viciae. Similar to ascofuranone, which specifically inhibits trypanosome alternative oxidase by acting at the ubiquinol binding domain, ascochlorin is also structurally related to ubiquinol. When added to the mitochondrial preparations isolated from rat liver, or the yeast Pichia (Hansenula) anomala, ascochlorin inhibited the electron transport via CoQ in a fashion comparable to antimycin A and stigmatellin, indicating that this antibiotic acted on the cytochrome bc1 complex. In contrast to ascochlorin, ascofuranone had much less inhibition on the same activities. On the one hand, like the Qi site inhibitors antimycin A and funiculosin, ascochlorin induced in H. anomala the expression of nuclear-encoded alternative oxidase gene much more strongly than the Qo site inhibitors tested. On the other hand, it suppressed the reduction of cytochrome b and the generation of superoxide anion in the presence of antimycin A3 in a fashion similar to the Qo site inhibitor myxothiazol. These results suggested that ascochlorin might act at both the Qi and the Qo sites of the fungal cytochrome bc1 complex. Indeed, the altered electron paramagnetic resonance (EPR) line shape of the Rieske iron-sulfur protein, and the light-induced time resolved cytochrome b and c reduction kinetics of Rhodobacter capsulatus cytochrome bc1 complex in the presence of ascochlorin demonstrated that this inhibitor can bind to both the Qo and Qi sites of the bacterial enzyme. Additional experiments using purified bovine cytochrome bc1 complex showed that ascochlorin inhibits reduction of cytochrome b by ubiquinone through both Qi and Qo sites. Moreover, crystal structure of chicken cytochrome bc1 complex treated with excess ascochlorin revealed clear electron densities that could be attributed to ascochlorin bound at both the Qi and Qo sites. Overall findings clearly show that ascochlorin is an unusual cytochrome bc1 inhibitor that acts at both of the active sites of this enzyme.

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“…2 Subsequently, many structurally related compounds have been isolated from various fungi such as an unclassified Fusarium species LL-Z1272, 3 Cylindrocladium sp., 4 Cylindrocladium ilicicola MFC-870, 5 Nectria coccinea, 6 Colletotrichum nicotianae, 7 Acremonium luzulae, 8 Cephalosporium diospyri, 9 Verticillium sp. FO-2787, 10 Cylindrocarpon lucidum, 11 Nigrosabulum globosum 12 and the insect pathogenic fungus Verticillium hemipterigenum BCC 2370.…”

Section: Introductionmentioning

confidence: 99%

LL-Z1272α epoxide, a precursor of ascochlorin produced by a mutant of Ascochyta viciae

et al. 2009

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A novel metabolite, LL-Z1272a epoxide, structurally related to ascochlorin, was isolated from the cultured mycelium of Ascochyta viciae J-29, a mutant derived from A. viciae Libert. The structure was elucidated on the basis of spectroscopic data. The epoxide is proposed to be enzymatically formed from LL-Z1272a and is a precursor of ascochlorin, an antiviral and antitumor antibiotic. The conversion of the epoxide to ascochlorin by cyclization of its farnesyl chain to a cyclohexanone ring is similar to that of squalene 2, 3-oxide to sterols. Unlike ascochlorin, the new metabolite had no growth inhibitory activity against Candida albicans in the paper-disc agar diffusion assay.

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Ascochlorin: A terpenoid metabolite from Acremonium luzulae

Cited by 18 publications

References 4 publications

Phytotoxic Metabolites Produced by Legume-Associated Ascochyta and Its Related Genera in the Dothideomycetes

Phytotoxic Metabolites Produced by Legume-Associated Ascochyta and Its Related Genera in the Dothideomycetes

Ascochlorin is a novel, specific inhibitor of the mitochondrial cytochrome bc1 complex

LL-Z1272α epoxide, a precursor of ascochlorin produced by a mutant of Ascochyta viciae

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