Biogenesis of Citrinin

Schwenk, Erwin; Alexander, George J.; Gold, Allen M.; Stevens, Dean F.

doi:10.1016/s0021-9258(19)77370-0

Cited by 49 publications

(22 citation statements)

References 4 publications

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“…Citrinin 1 is a well‐known mycotoxin that is closely related to the azaphilones, but citrinin 1 itself is resistant to amination [3] . Early investigations into citrinin 1 biosynthesis used radioisotopes, which confirmed its polyketide origin through the incorporation of 14 C‐labelled acetate [8,9] . Recent work has defined the molecular steps to citrinin 1 biosynthesis through a series of gene knockout and heterologous expression experiments (Scheme 1).…”

Section: Elucidation Of Azaphilone and Relevant Related Biosynthetic Pathwaysmentioning

confidence: 99%

“… [3] Early investigations into citrinin 1 biosynthesis used radioisotopes, which confirmed its polyketide origin through the incorporation of 14 C‐labelled acetate. [ 8 , 9 ] Recent work has defined the molecular steps to citrinin 1 biosynthesis through a series of gene knockout and heterologous expression experiments (Scheme 1 ). [3] Although citrinin 1 bears much structural similarity to azaphilones, consisting of a pyranoquinone bicyclic core, and is in fact often defined as an azaphilone, [1] the molecular steps to its structure differentiate at an early stage.…”

Section: Elucidation Of Azaphilone and Relevant Related Biosynthetic Pathwaysmentioning

confidence: 99%

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Core Steps to the Azaphilone Family of Fungal Natural Products

et al. 2021

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Azaphilones are a family of polyketide‐based fungal natural products that exhibit interesting and useful bioactivities. This minireview explores the literature on various characterised azaphilone biosynthetic pathways, which allows for a proposed consensus scheme for the production of the core azaphilone structure, as well as identifying early diversification steps during azaphilone biosynthesis. A consensus understanding of the core enzymatic steps towards a particular family of fungal natural products can aid in genome‐mining experiments. Genome mining for novel fungal natural products is a powerful technique for both exploring chemical space and providing new insights into fungal natural product pathways.

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Section: Elucidation Of Azaphilone and Relevant Related Biosynthetic Pathwaysmentioning

confidence: 99%

Section: Elucidation Of Azaphilone and Relevant Related Biosynthetic Pathwaysmentioning

confidence: 99%

Core Steps to the Azaphilone Family of Fungal Natural Products

et al. 2021

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“…Both in biogenetic and structural terms, pulvilloric acid closely resembles two other secondary metabolites. These are citrinin, whose biogenesis has been worked out by several groups (Birch et al, 1958;Schwenk et al, 1958;Rodig et al, 1966) and has been shown to involve the acetate-polymalonate single carbon-transfer pathways; and ascochitine, more recently characterized by Iwai and Mishima(1965).This paper reports strain and fermentation improvements which have lead to consistent, high yield production of pulvilloric acid; and describes a facile isolation method for obtaining the analytically pure antibiotic. As a preliminary to radioactive tracer experiments on the elucidation of the biosynthesis of pulvilloric acid, a carbon-by-carbon degradative procedure, with satisfactory yields of intermediates at each stage, has been developed.…”

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confidence: 96%

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confidence: 99%

Biosynthesis of pulvilloric acid. I. Production, isolation, and degradations

Tanenbaum¹,

Nakajima²

1969

Biochemistry

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A study of the environmental conditions needed for maximal laboratory yields of pulvilloric acid, an antibiotic substance produced by Penicillium pulvillorum, led to the estimated production in stationary cultures of quantities over 1.3 g/1. The requisite medium is 5% glycerol-Czapek-Dox supplemented with 0.1 ml of corn steep liquor/1. Improvements in isolation and purification steps were found which overcame the major difficulty involved in work with this metabolite, i.e., its instability. A complete stepwise degradation procedure, adaptable for radioactive tracer experiments, was developed. This process involved hydrolysis of pulvilloric acid into the known l-(3-dihydroxyphenyl)-2-heptanol, followed by methylation and dehydration which provided l-(3,5dimethoxyphenyl)-1 -heptene. The latter intermediate was p X. ulvilloric acid is a yellow antifungal and antibacterial substance produced by Penicillium pulvillorum (Brian et al., 1957). Its molecular structure (I) has been determined by degradative (McOmie et al., 1963(McOmie et al., , 1966 and synthetic (Bullimore et al., 1967) studies. Both in biogenetic and structural terms, pulvilloric acid closely resembles two other secondary metabolites. These are citrinin, whose biogenesis has been worked out by several groups (Birch et al., 1958;Schwenk et al., 1958;Rodig et al., 1966) and has been shown to involve the acetate-polymalonate single carbon-transfer pathways; and ascochitine, more recently characterized by Iwai and Mishima(1965).This paper reports strain and fermentation improvements which have lead to consistent, high yield production of pulvilloric acid; and describes a facile isolation method for obtaining the analytically pure antibiotic. As a preliminary to radioactive tracer experiments on the elucidation of the biosynthesis of pulvilloric acid, a carbon-by-carbon degradative procedure, with satisfactory yields of intermediates at each stage, has been developed. Experimental Procedures and ResultsFermentations. It was earlier reported (Nakajima and Tanenbaum, 1968) that strain selection by sectoring of P.pulvillorum (ACC 1124) as originally received, led to isolates

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“…Citrinin biogenisis has been studied extensively by several workers (1)(2)(3)(4), and has been shown to follow the polyacetate (or acetate-polymalonate) pathway 5-7. The two-carbon fragments from acetate are condensed in a linear chain which is cyclized, and the extraskeletal units are added from the Ci metabolic pool (4).…”

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confidence: 99%