Molecular breeding of a fungus producing a precursor diterpene suitable for semi-synthesis by dissection of the biosynthetic machinery

PLoS ONE

Volumn 7, Issue 8, 2012, Pages

  Noike, Motoyoshi ^a   Ono, Yusuke ^a   Araki, Yuji ^a   Tanio, Ryo ^a   Higuchi, Yusuke ^b   Nitta, Hajime ^b   Hamano, Yoshimitsu ^c   Toyomasu, Tomonobu ^d   Sassa, Takeshi ^d   Kato, Nobuo ^b   Dairi, Tohru ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

^c FUKUI PREFECTURAL UNIVERSITY   (Japan)

^d YAMAGATA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COTYLENIN A; DITERPENE; FUSICOCCIN; HYDROXYL GROUP; PHYTOHORMONE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BIOSYNTHESIS; BREEDING; CHEMICAL REACTION; DRUG STRUCTURE; FUNGAL METABOLISM; FUNGAL STRAIN; FUNGAL VIABILITY; FUNGUS; GENE DISRUPTION; HORMONE ACTION; MASS SCREENING; METABOLITE; MUTAGENESIS; NONHUMAN; NUCLEOTIDE SEQUENCE; PHENOTYPE; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; ASCOMYCOTA; DIRECTED MOLECULAR EVOLUTION; DITERPENES; GLYCOSIDES; MUTAGENESIS;

ACTINOBACTERIA; FUNGI; PHOMOPSIS AMYGDALI;

EID: 84864749534     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0042090     Document Type: Article

References (30)

1. Ballio A, Brufani M, Casinovi CG, Cerrini S, Fedeli W, et al. (1968) The structure of fusicoccin A. Experientia. 24: 631-635.
2. Sassa T, (1971) Cotylenins, leaf growth substances produced by a fungus. I. Isolation and characterization of cotylenins A and B. Agric Biol Chem 35: 1415-1418.
3. Sassa T, Ooi T, Nukina M, Kato N, (1998) Structural Confirmation of Cotylenin A, a Novel Fusicoccane-diterpene Glycoside with Potent Plant Growth-regulating Activity from Cladosporium Fungus sp. 501-7W. Biosci Biotechnol Biochem 62: 1815-1818.
4. Marre E, (1979) Fusicoccin: A Tool in Plant Physiology. Ann Rev Plant Physiol 30: 273-288.
5. Asahi K, Honma Y, Hazeki K, Sassa T, Kubohara Y, et al. (1997) Cotylenin A, a plant-growth regulator, induces the differentiation in murine and human myeloid leukemia cells. Biochem Biophys Res Commun 238: 758-763.
6. Honma Y, (2002) Cotylenin A-a plant growth regulator as a differentiation-inducing agent against myeloid leukemia. Leuk Lymphoma 43: 1169-1178.
7. Honma Y, Ishii Y, Yamamoto-Yamaguchi Y, Sassa T, Asahi K, (2003) Cotylenin A, a differentiation-inducing agent, and IFN-alpha cooperatively induce apoptosis and have an antitumor effect on human non-small cell lung carcinoma cells in nude mice. Cancer Res 63: 3659-3666.
8. Honma Y, Kasukabe T, Yamori T, Kato N, Sassa T, (2005) Antitumor effect of cotylenin A plus interferon-alpha: possible therapeutic agents against ovary carcinoma. Gynecol Oncol 99: 680-688.
9. Matsunawa M, Ishii Y, Kasukabe T, Tomoyasu S, Ota H, et al. (2006) Cotylenin A-induced differentiation is independent of the transforming growth factor-beta signaling system in human myeloid leukemia HL-60 cells. Leuk Lymphoma 47: 733-740.
10. Kawakami K, Hattori M, Inoue T, Maruyama Y, Ohkanda J, et al. (2012) A novel fusicoccin derivative preferentially targets hypoxic tumor cells and inhibits tumor growth in xenografts. Anticancer Agents Med Chem in press. (PMID:22263802).
11. Mackinnon SL, Keifer P, Ayer WA, (1999) Components from the phytotoxic extract of Alternaria brassicicola, a black spot pathogen of canola. Phytochemistry 51: 215-221.
12. Barrow KD, Barton DHR, Chain EB, Bageenda-Kasujja D, Mellows G, (1975) Fusicoccin. Part IV. The structure of fusicoccin J. J Chem Soc Perkin Trans 1 877-883.
13. Barrow KD, Barton DHR, Chain EB, Ohnsorge UF, Sharma RP, (1973) Fusicoccin. Part III. The structure of fusicoccin H. J Chem Soc Perkin Trans 1 1590-1599.
14. Toyomasu T, Tsukahara M, Kaneko A, Niida R, Mitsuhashi W, et al. (2007) Fusicoccins are biosynthesized by an unusual chimera diterpene synthase in fungi. Proc Natl Acad Sci U S A 104: 3084-3088.
15. Ono Y, Minami A, Noike M, Higuchi Y, Toyomasu T, et al. (2011) Dioxygenases, key enzymes to determine the aglycon structures of fusicoccin and brassicicene, diterpene compounds produced by fungi. J Am Chem Soc 133: 2548-2555.
16. Sassa T, Tajima N, Sato M, Takahashi A, Kato N, (2002) Fusicoccins P and Q, and 3-epifusicoccins H and Q, new polar fusicoccins from isolate Niigata 2-A of a peach Fusicoccum canker fungus. Biosci Biotechnol Biochem 66: 2356-2361.
17. Noike M, Liu C, Ono Y, Hamano Y, Toyomasu T, et al. (2012) An enzyme catalyzing O-prenylation of the glucose moiety of fusicoccin A, a diterpene glucoside produced by the fungus Phomopsis amygdali. Chembiochem 13: 66-573.
18. Barrow KD, Barton DHR, Chain E, Conlay C, Smale TC, et al. (1971) Fusicoccin. Part I. The nature of the substituent groups. J Chem Soc C 1259-1264.
19. Tajima N, Kume H, Kanematsu S, Kato N, Sassa T, (2001) Chemical identification of fusicoccins from a Japanese isolate Niigata 2 of peach Fusicoccum canker fungus (Phomopsis amygdali) and production of 3'-deacetylfusicoccin A by the fungus. J Pestcide Sci 27: 64-67.
20. Minami A, Tajima N, Higuchi Y, Toyomasu T, Sassa T, et al. (2009) Identification and functional analysis of brassicicene C biosynthetic gene cluster in Alternaria brassicicola. Bioorg Med Chem Lett 19: 870-874.
21. Hashimoto M, Higuchi Y, Takahashi S, Osada H, Sakaki T, et al. (2009) Functional analyses of cytochrome P450 genes responsible for the early steps of brassicicene C biosynthesis. Bioorg Med Chem Lett 19: 5640-5643.
22. Tyo KE, Alper HS, Stephanopoulos GN, (2007) Expanding the metabolic engineering toolbox: more options to engineer cells. Trends Biotechnol 25: 132-137.
23. Ajikumar PK, Xiao WH, Tyo KE, Wang Y, Simeon F, et al. (2010) Isoprenoid pathway optimization for Taxol precursor overproduction in Escherichia coli. Science 330: 70-74.
24. Tudzynski B, (2005) Gibberellin biosynthesis in fungi: genes, enzymes, evolution, and impact on biotechnology. Appl Microbiol Biotechnol 66: 597-611.
25. Hamano Y, Kuzuyama T, Itoh N, Furihata K, Seto H, et al. (2002) Functional analysis of eubacterial diterpene cyclases responsible for biosynthesis of a diterpene antibiotic, terpentecin. J Biol Chem 277: 37098-37104.
26. Kawasaki T, Hayashi Y, Kuzuyama T, Furihata K, Itoh N, et al. (2006) Biosynthesis of a natural polyketide-isoprenoid hybrid compound, furaquinocin A: identification and heterologous expression of the gene cluster. J Bacteriol 188: 1236-1244.
27. Hayashi Y, Onaka H, Itoh N, Seto H, Dairi T, (2007) Cloning of the gene cluster responsible for biosynthesis of KS-505a (longestin), a unique tetraterpenoid. Biosci Biotechnol Biochem 71: 3072-3081.
28. Hayashi Y, Matsuura N, Toshima H, Itoh N, Ishikawa J, et al. (2008) Cloning of the gene cluster responsible for the biosynthesis of brasilicardin A, a unique diterpenoid. J Antibiot (Tokyo) 61: 164-174.
29. Dairi T, (2005) Studies on biosynthetic genes and enzymes of isoprenoids produced by actinomycetes. J Antibiot (Tokyo) 58: 227-243.
30. Kimura N, Tsuge T, (1993) Gene cluster involved in melanin biosynthesis of the filamentous fungus Alternaria alternata. J Bacteriol 175: 4427-4435.