Genetic localization of the orevactaene/epipyrone biosynthetic gene cluster in Epicoccum nigrum

Bioorganic and Medicinal Chemistry Letters

Volumn 30, Issue 14, 2020, Pages

  Lim, Yoon Ji ^a   Choi, Eunha ^a   Park, Si Hyung ^b   Kwon, Hyung Jin ^a  

^a Myong Ji University   (South Korea)

^b Mokpo National University   (South Korea)

Author keywords

Biosynthetic gene cluster; Epicoccum nigrum; Epipyrone A; Highly reducing fungal polyketide synthase; Orevactaene

Indexed keywords

2 PYRONE POLYKETIDE; CELL PROTEIN; CYTOCHROME P450; EPIPYRONE PROTEIN; FUNGAL PROTEIN; GLYCOSYLTRANSFERASE; POLYKETIDE; POLYKETIDE SYNTHASE; TRANSPORTER PROTEIN; UNCLASSIFIED DRUG; OREVACTAENE; PYRAN DERIVATIVE;

ARTICLE; EPICOCCUM NIGRUM; EPN GENE; EPNA GENE; EPNB GENE; EPNC GENE; EPND GENE; FUNGAL GENE; FUNGAL GENETIC PHENOMENA AND FUNCTIONS; FUNGAL GENOME; GENE CLUSTER; GENE EXPRESSION; GENE INACTIVATION; GENE SEQUENCE; GENETIC LOCALIZATION; GENETIC TRANSCRIPTION; GENOME ANALYSIS; GENOME SEQUENCE; NONHUMAN; OXIDATION; PROTEIN DEPLETION; PROTEIN SYNTHESIS; ASCOMYCETES; CHEMISTRY; CONFORMATION; GENETICS; METABOLISM; MULTIGENE FAMILY;

ASCOMYCOTA; MOLECULAR CONFORMATION; MULTIGENE FAMILY; PYRANS;

EID: 85084611896     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2020.127242     Document Type: Article

References (26)

1. Shu, Y.Z., Ye, Q., Li, H., et al. Orevactaene, a novel binding inhibitor of HIV-1 rev protein to Rev response element (RRE) from Epicoccum nigrum WC47880. Bioorg Med Chem Lett 7 (1997), 2295–2298.
2. Kimura J, Furui M, Kanda M, Sugiyama M. Telomerase inhibitor. 2002; Japan Patent 2002047281A.
3. Preindl, J., Schulthoff, S., Wirtz, C., Lingnau, J., Fürstner, A., Polyunsaturated C-glycosidic 4-hydroxy-2-pyrone derivatives: Total synthesis shows that putative orevactaene is likely identical with epipyrone A. Angew Chem Int Ed Engl 56 (2017), 7525–7530.
4. van Ginkel R, Selwood AI, Wilkins AL, Ford S, Calder C. Anti-microbial compositions. 2012; US Patent 20120108526A1.
5. Peng, J., Jiao, J., Li, J., et al. Pyronepolyene C-glucosides with NF-κB inhibitory and anti-influenza A viral (H1N1) activities from the sponge-associated fungus Epicoccum sp. JJY40. Bioorg Med Chem Lett 22 (2012), 3188–3190.
6. Hufendiek P. Enzyme-inhibitory secondary metabolites and their exudation in the marine-derived fungus Epicoccum nigrum link. 2017.
7. Burge, W.R., Buckley, L.J., Sullivan, J.D. Jr, McGrattan, C.J., Ikawa, M., Isolation and biological activity of the pigments of the mold Epicoccum nigrum. J Agri Food Chem 24 (1976), 555–559.
8. Ikawa, M., Mcgrattan, C.J., Burgea, W.R., Iannitelli, R.C., Uebel, J.J., Noguchi, T., Epirodin, a polyene antibiotic from the mold Epicoccum nigrum. J Antibiot 31 (1978), 159–161.
9. Hopwood, D.A., Sherman, D.H., Molecular genetics of polyketides and its comparison to fatty acid biosynthesis. Ann Rev Genet 24 (1990), 37–62.
10. Staunton, J., Weissman, K.J., Polyketide biosynthesis: a millennium review. Nat Prod Rep 18 (2001), 380–416.
11. Chooi, Y.H., Tang, Y., Navigating the fungal polyketide chemical space: from genes to molecules. J Org Chem 77 (2012), 9933–9953.
12. Cox, R.J., Polyketides, proteins and genes in fungi: programmed nano-machines begin to reveal their secrets. Org Biomol Chem 5 (2007), 2010–2026.
13. Hertweck, C., The biosynthetic logic of polyketide diversity. Angew Chem Int Ed Engl 48 (2009), 4688–4716.
14. Kennedy, J., Auclair, K., Kendrew, S.G., Park, C., Vederas, J.C., Hutchinson, C.R., Modulation of polyketide synthase activity by accessory proteins during lovastatin biosynthesis. Science 284 (1999), 1368–1372.
15. Fokin, M., Fleetwood, D., Weir, B.S., Villas-Boas, S., Genome sequence of the saprophytic ascomycete Epicoccum nigrum strain ICMP 19927, isolated from New Zealand. Genome Announc 5 (2017), e00557–17.
16. Carmody, M., Murphy, B., Byrne, B., et al. Biosynthesis of amphotericin derivatives lacking exocyclic carboxyl groups. J Bio Chem 280 (2005), 34420–34426.
17. Balakrishnan, B., Chandran, R., Park, S.H., Kwon, H.J., Delineating citrinin biosynthesis: Ctn-ORF3 dioxygenase-mediated multi-step methyl oxidation precedes a reduction-mediated pyran ring cyclization. Bioorg Med Chem Lett 26 (2016), 392–396.
18. He, Y., Cox, R.J., The molecular steps of citrinin biosynthesis in fungi. Chem Sci 7 (2016), 2119–2127.
19. Blin, K., Shaw, S., Steinke, K., et al. antiSMASH 5.0: updates to the secondary metabolite genome mining pipeline. Nucleic Acids Res 47 (2019), W81–W87.
20. Medema, M.H., Kottmann, R., Yilmaz, P., et al. Minimum information about a biosynthetic gene cluster. Nat Chem Biol 11 (2015), 625–631.
21. Medema, M.H., Takano, E., Breitling, R., Detecting sequence homology at the gene cluster level with MultiGeneBlast. Mol Biol Evol 30 (2013), 1218–1223.
22. Hashimoto, M., Nonaka, T., Fujii, I., Fungal type III polyketide synthases. Nat Prod Rep 31 (2014), 1306–1317.
23. Kasahara, K., Fujii, I., Oikawa, H., Ebizuka, Y., Expression of Alternaria solani PKSF generates a set of complex reduced-type polyketides with different carbon-lengths and cyclization. ChemBioChem 7 (2006), 920–924.
24. Fujii, I., Yoshida, N., Shimomaki, S., Oikawa, H., Ebizuka, Y., An iterative type I polyketide synthase PKSN catalyzes synthesis of the decaketide alternapyrone with regio-specific octa-methylation. Chem Biol 12 (2005), 1301–1309.
25. Gordon, S.P., Tseng, E., Salamov, A., et al. Widespread polycistronic transcripts in fungi revealed by single-molecule mRNA sequencing. PLoS One, 10, 2015, e0132628.
26. Yue, Q., Chen, L., Li, Y., et al. Functional operons in secondary metabolic gene clusters in Glarea lozoyensis (Fungi, Ascomycota, Leotiomycetes). MBio 6 (2015), e00703–15.