Enzymatic Formation of the Bisfuran Structure in Aflatoxin Biosynthesis

Overview

Journal Appl Environ Microbiol

Specialties Environmental Health
Microbiology

Date 1980 Jan 1

PMID 7356313

Citations 17

Authors

N C Wan

D P Hsieh

Affiliations

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Abstract

A relatively stable enzyme system that converts versiconal hemiacetal acetate to versicolorin A was isolated from the soluble fraction of the homogenized cells of Aspergillus parasiticus ATCC 15517. The cell-free preparation did not require oxygen or oxidized nicotinamide adenine dinucleotide phosphate for activity, nor did it require dithiothreitol, polyclar (polyvinyl pyrrolidone), or glycerol for stabilization of activity. It was susceptible to inhibition by dichlorvos and cysteine. Isotope tracer studies revealed involvement of several intermediates in the conversion of versiconal hemiacetal acetate to versicolorin A. These findings confirm the biogenetic relationship of versiconal hemiacetal acetate and versicolorin A, and they confirm that the bisfuran ring structure in aflatoxins and related fungal metabolites is derived from the hemiacetal structure of versiconal hemiacetal acetate.

Citing Articles

Exploration, antifungal and antiaflatoxigenic activity of halophilic bacteria communities from saline soils of Howze-Soltan playa in Iran.

Jafari S, Aghaei S, Afifi-Sabet H, Shams-Ghahfarokhi M, Jahanshiri Z, Gholami-Shabani M Extremophiles. 2017; 22(1):87-98.

PMID: 29134389 DOI: 10.1007/s00792-017-0979-2.

Biosynthesis of versicolorin A.

Anderson M, Dutton M Appl Environ Microbiol. 1980; 40(4):706-9.

PMID: 7425622 PMC: 291648. DOI: 10.1128/aem.40.4.706-709.1980.

Role of versicolorin A and its derivatives in aflatoxin biosynthesis.

Dutton M, Anderson M Appl Environ Microbiol. 1982; 43(3):548-51.

PMID: 6803669 PMC: 241872. DOI: 10.1128/aem.43.3.548-551.1982.

Biogenesis of the C20 polyketide, aflatoxin. A review.

Applebaum R, Marth E Mycopathologia. 1981; 76(2):103-14.

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Precursor recognition by kinetic pulse-labeling in a toxigenic aflatoxin B1-producing strain of Aspergillus.

Zamir L, Hufford K Appl Environ Microbiol. 1981; 42(1):168-73.

PMID: 6789767 PMC: 243979. DOI: 10.1128/aem.42.1.168-173.1981.

References

Raj H, Viswanathan L, Murthy H, Venkitasubramanian T . Biosynthesis of aflatoxins by cell-free preparations from Aspergillus flavus. Experientia. 1969; 25(11):1141-2. DOI: 10.1007/BF01900235. View

Hsieh D . Inhibition of aflatoxin biosynthesis of dichlorvos. J Agric Food Chem. 1973; 21(3):468-70. DOI: 10.1021/jf60187a035. View

Yao R, Hsieh D . Step of dichlorvos inhibition in the pathway of aflatoxin biosynthesis. Appl Microbiol. 1974; 28(1):52-7. PMC: 186587. DOI: 10.1128/am.28.1.52-57.1974. View

Lee L, Bennett J, CUCULLU A, Stanley J . Synthesis of versicolorin A by a mutant strain of Aspergillus parasiticus deficient in aflatoxin production. J Agric Food Chem. 1975; 23(6):1132-4. DOI: 10.1021/jf60202a011. View

Singh R, Hsieh D . Enzymatic conversion of sterigmatocystin into aflatoxin B1 by cell-free extracts of Aspergillus parasiticus. Appl Environ Microbiol. 1976; 31(5):743-5. PMC: 291187. DOI: 10.1128/aem.31.5.743-745.1976. View

Wong J, Hsieh D . Mutagenicity of aflatoxins related to their metabolism and carcinogenic potential. Proc Natl Acad Sci U S A. 1976; 73(7):2241-4. PMC: 430512. DOI: 10.1073/pnas.73.7.2241. View

Singh R, Hsieh D . Aflatoxin biosynthetic pathway: elucidation by using blocked mutants of Aspergillus parasiticus. Arch Biochem Biophys. 1977; 178(1):285-92. DOI: 10.1016/0003-9861(77)90193-x. View

Cox R, Churchill F, Cole R, Dormer J . Carbon-13 nuclear magnetic resonance studies of the structure and biosynthesis of versiconal acetate. J Am Chem Soc. 1977; 99(9):3159-61. DOI: 10.1021/ja00451a049. View

Fitzell D, Singh R, Hsieh D, Motell E . Nuclear magnetic resonance identification of versiconal hemiacetal acetate as an intermediate in aflatoxin biosynthesis. J Agric Food Chem. 1977; 25(5):1193-7. DOI: 10.1021/jf60213a024. View

10.

Wong J, Singh R, Hsieh D . Mutagenicity of fungal metabolites related to aflatoxin biosynthesis. Mutat Res. 1977; 44(3):447-50. DOI: 10.1016/0027-5107(77)90102-6. View

11.

Maggon K, Gupta S, Venkitasubramanian T . Biosynthesis of aflatoxins. Bacteriol Rev. 1977; 41(4):822-55. PMC: 414029. DOI: 10.1128/br.41.4.822-855.1977. View

12.

Anderson M, Dutton M . The use of cell free extracts derived from fungal protoplasts in the study of aflatoxin biosynthesis. Experientia. 1979; 35(1):21-2. DOI: 10.1007/BF01917850. View