Isolation of an Anabolic, Uterotrophic Compound from Corn infected with Gibberella zeae

Stob, Martin; Baldwin, Robert S.; Tuite, J.; Andrews, F. N.; Gillette, K. G.

doi:10.1038/1961318a0

Cited by 349 publications

(138 citation statements)

References 1 publication

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“…1A) represent a unique family of fungal polyketides (8). These mycotoxins possess a wide array of potent biological activities, including radicicol (Hsp90 inhibitor) (9), LL-Z1640-2 (TAK1 inhibitor) (10), hypothemycin (MAP kinase inhibitor) (11), and zearalenone 1 (estrogen receptor agonist) (12). Compounds in this family are macrolactones and exhibit structural features characteristic of both reducing and nonreducing fungal polyketides.…”

mentioning

confidence: 99%

A polyketide macrolactone synthase from the filamentous fungus Gibberella zeae

Zhou

Zhan

Watanabe

et al. 2008

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

103

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Resorcylic acid lactones represent a unique class of fungal polyketides and display a wide range of biological activities, such as nanomolar inhibitors of Hsp90 and MAP kinase. The biosynthesis of these compounds is proposed to involve two fungal polyketide synthases (PKS) that function collaboratively to yield a 14-membered macrolactone with a resorcylate core. We report here the reconstitution of Gibberella zeae PKS13, which is the nonreducing PKS associated with zearalenone biosynthesis. Using a small molecule mimic of the natural hexaketide starter unit, we reconstituted the entire repertoire of PKS13 activities in vitro, including starter-unit selection, iterative condensation, regioselective C2-C7 cyclization, and macrolactone formation. PKS13 synthesized both natural 14-membered and previously uncharacterized 16-membered resorcylic acid lactones, indicating relaxed control in both iterative elongation and macrocyclization. PKS13 exhibited broad starter-unit specificities toward fatty acyl-CoAs ranging in sizes between C6 and C16 and displayed the highest activity toward decanoyl-CoA. PKS13 was shown to be active in Escherichia coli and synthesized numerous alkyl pyrones and alkyl resorcylic esters without exogenously supplied precursors. We demonstrated that PKS13 can interact with E. coli fatty acid biosynthetic machinery and can be primed with fatty-acyl ACPp at low-micromolar concentrations. PKS13 synthesized new polyketides in E. coli when the culture was supplemented with synthetic precursors, showcasing its utility in precursor-directed biosynthesis. PKS13 is therefore a highly versatile polyketide macrolactone synthase that is useful in the engineered biosynthesis of polyketides, including resorcylic acid lactones that are not found in nature.ketosynthase ͉ resorcylic acid ͉ starter unit ͉ Hsp90 ͉ thioesterase

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mentioning

confidence: 99%

A polyketide macrolactone synthase from the filamentous fungus Gibberella zeae

Zhou

Zhan

Watanabe

et al. 2008

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

103

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“…Zearalenone has oestrogenic effects in various animal species that include infertility, vulvae oedema, and mammary hypertrophy in females (Peraica et al 1999). Stob et al (1962) were the first to isolate an uterotrophic compound from mouldy corn, while in 1965Christensen et al (1965 isolated a compound (preliminarily called F-2) from corn inoculated with Fusarium. In 1966 Urry et al (1966) isolated the same compound from contaminated corn and they called it zearalenone.…”

Section: Zearalenonementioning

confidence: 99%

Ecological conditions affecting mycotoxin production in cereals: a review

Milani¹

2013

Vet. Med.

146

105

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Spoilage fungi are ubiquitous contaminants of cereals, pre-and post-harvest. These fungi can produce a wide range of secondary metabolites under ecological conditions which are conducive for growth. However, some of these secondary metabolites are toxic and have a significant impact if they enter the production and animal food chains. Prevention of mycotoxin contamination of feed and food raw materials is now considered more important than subsequent cure. The key ecological determinants pre-and post-harvest are water availability and temperature (climate). Accurate information is therefore needed on the impact of an association between these key factors, and it is necessary to understand which are marginal and which critical for germination and toxin production. There have only been a few studies where attempts have been made to integrate the available information on these factors in relation to different raw materials for feed and food processing, especially cereals. This review will examine the available information on the main climatic factors, i.e., water availability and temperature affecting mycotoxin production such as, aflatoxins, ochratoxins, fumonisins, zearalenone, deoxynivalenol and citrinin. This information is crucial for accurately focusing and monitoring key critical control points in the feed and food chain to optimise prevention strategies.

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“…13,15 Besides its geranyl bibenzyl scaffold, the molecule contains a 6-alkyl-2,4-dihydroxybenzoic acid (resorcylic acid) motif, which occurs in numerous natural products. [19][20][21][22] Reported syntheses invariably require the use of protective groups and strong bases, subsequent alkylations giving low yields and poor regioselectivity.…”

Section: Introductionmentioning

confidence: 99%

“…The combined organic layers were dried with anhydrous MgSO 4 , rotary evaporated, and chromatographed on silica gel to obtain β-keto ester 6 (0.59 g, 53% over two steps from acid 3) as a yellow oil: R f 0. 22 3-Phenylpropanoyl chloride (8). SOCl 2 (0.7 mL, 7.5 mmol) was added dropwise into a 25 mL round-bottle-flask containing 3-phenylpropanoic acid (1.0 g, 6.8 mmol) in CHCl 3 (10 mL).…”

mentioning

confidence: 99%

Total synthesis of amorfrutin B via a Pd-catalyzed regioselective geranyl migration-decarboxylation-cycloaromatization cascade

Wang¹,

Kong²,

Qiao³

2015

Arkivoc

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A biomimetic total synthesis of amorfrutin B, a resorcylate with geranyl bibenzyl scaffold, has been completed in eight steps from 2,2,6-trimethyl-4H-1,3-dioxin-4-one. The key step utilized a highly regioselective Pd-catalyzed geranyl migration-decarboxylation-cycloaromatization cascade. The methodology should be of practical utility in the construction of geranyl bibenzyl scaffolds manifested in many natural products.

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Isolation of an Anabolic, Uterotrophic Compound from Corn infected with Gibberella zeae

Cited by 349 publications

References 1 publication

A polyketide macrolactone synthase from the filamentous fungus Gibberella zeae

A polyketide macrolactone synthase from the filamentous fungus Gibberella zeae

Ecological conditions affecting mycotoxin production in cereals: a review

Total synthesis of amorfrutin B via a Pd-catalyzed regioselective geranyl migration-decarboxylation-cycloaromatization cascade

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