Some new terpenoid metabolites from an unidentified fusarium species

Ellestad, George A.; Evans, Ralph H.; Kunstmann, M. P.

doi:10.1016/s0040-4020(01)82703-4

Cited by 66 publications

(49 citation statements)

References 12 publications

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“…Mutant J-15 produced LL-Z1272a only (unpublished data), whereas mutant J-29 produced LL-Z1272a epoxide, together with ascofuranone (in this report). Both ascochlorin and LL-Z1272a have been isolated together from Fusarium species, 3 Nectria coccinea 6 and Verticillium sp. 10 Ellestad et al 3 proposed that the farnesyl chain of LL-Z1272a was epoxidized, cyclized to a cyclohexanone ring and converted to ascochlorin LL-Z1272a epoxide K Hosono et al (Figure 3), just as in the case of the enzymatic conversion of squalene 2, 3-oxide to lanosterol and cholesterol.…”

Section: Discussionmentioning

confidence: 99%

“…Both ascochlorin and LL-Z1272a have been isolated together from Fusarium species, 3 Nectria coccinea 6 and Verticillium sp. 10 Ellestad et al 3 proposed that the farnesyl chain of LL-Z1272a was epoxidized, cyclized to a cyclohexanone ring and converted to ascochlorin LL-Z1272a epoxide K Hosono et al (Figure 3), just as in the case of the enzymatic conversion of squalene 2, 3-oxide to lanosterol and cholesterol. 19 However, the epoxide, the expected intermediate to which the farnesyl chain with a terminal double bond was converted, had not been previously isolated.…”

Section: Discussionmentioning

confidence: 99%

“…It has been proposed that the farnesyl chain of LL-Z1272a (Figure 1) is epoxidized, cyclized to a cyclohexanone ring and converted to ascochlorin just as in the case of the enzymatic conversion of squalene 2, 3-oxide to lanosterol and cholesterol. 3 However, this epoxide, the expected intermediate to which the farnesyl chain with a terminal double bond is converted, has not been isolated hitherto.…”

Section: Introductionmentioning

confidence: 99%

“…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%

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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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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

et al. 2009

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“…LL-Z 1272b is a terpenoid antibiotic and is reported to have anti-T. pyriformis (anti-protozoal) and antitumor activity [29,30], and we reported that it showed inhibition of testosterone 5a -reductase from rat prostate [31]. A related antibiotic, ascofuranone, is reported to have in vitro and in vivo anti-trypanosomal activities [32,33].…”

Section: Discussionmentioning

confidence: 94%

Selective and Potent in Vitro Antitrypanosomal Activities of Ten Microbial Metabolites

et al. 2008

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More than 400 compounds isolated from soil microorganisms, and catalogued in the antibiotic library of the Kitasato Institute for Life Sciences, were screened against African trypanosomes. Ten compounds were found to have selective and potent antitrypanosomal activity in vitro: aureothin, cellocidin, destomycin A, echinomycin, hedamycin, irumamycin, LL-Z 1272b , Omethylnanaomycin A, venturicidin A and virustomycin A. Results of the in vitro assays using the GUTat 3.1 strain of Trypanosomal brucei brucei and the STIB900 strain of T. b. rhodesiense are presented. Cytotoxicity was determined using a human MRC-5 cell line. This is the first report of antitrypanosomal activities of the 10 microbial metabolites listed above.

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