Production of (+)-valencene in the mushroom-forming fungus S. commune

Applied Microbiology and Biotechnology

Volumn 98, Issue 11, 2014, Pages 5059-5068

  Scholtmeijer, Karin ^a   Cankar, Katarina ^b   Beekwilder, Jules ^b   Wösten, Han A B ^a   Lugones, Luis G ^a   Bosch, Dirk ^a,b,c  

^a UTRECHT UNIVERSITY   (Netherlands)

^b WAGENINGEN UNIVERSITY   (Netherlands)

^c DELFT UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

Basidiomycete; Mushroom; Schizophyllum commune; Sesquiterpene

Indexed keywords

ESCHERICHIA COLI; GENES; OLEFINS; YEAST;

BASIDIOMYCETE; MUSHROOM; SCHIZOPHYLLUM COMMUNE; SESQUITERPENES; VALENCENE;

SUBSTRATES;

FARNESYL DIPHOSPHATE; MEVALONIC ACID; REGULATOR PROTEIN; SCHIZOPHYLLAN; SESQUITERPENE; VALENCENE; ALKANE; CULTURE MEDIUM; FUNGAL DNA; N-DODECANE;

COLIFORM BACTERIUM; FRUITING; FUNGUS; GENE EXPRESSION; GENETIC ANALYSIS; GENOMICS; MUSHROOM; MUTATION; PROTEIN;

ARTICLE; FUNGAL GENE; FUNGAL GENOME; FUNGAL STRAIN; GENE DISRUPTION; GENE EXPRESSION; MASS FRAGMENTOGRAPHY; MYCELIUM; NONHUMAN; RNA SEQUENCE; SCHIZOPHYLLUM COMMUNE; SYNTHESIS; CHEMISTRY; CULTURE MEDIUM; DNA SEQUENCE; GENETICS; METABOLIC ENGINEERING; METABOLISM; MOLECULAR GENETICS; SCHIZOPHYLLUM;

BASIDIOMYCOTA; ESCHERICHIA COLI; FUNGI; SACCHAROMYCES CEREVISIAE; SCHIZOPHYLLUM COMMUNE;

ALKANES; CULTURE MEDIA; DNA, FUNGAL; METABOLIC ENGINEERING; METABOLIC NETWORKS AND PATHWAYS; MOLECULAR SEQUENCE DATA; SCHIZOPHYLLUM; SEQUENCE ANALYSIS, DNA; SESQUITERPENES;

EID: 84901654378     PISSN: 01757598     EISSN: 14320614     Source Type: Journal    
DOI: 10.1007/s00253-014-5581-2     Document Type: Article

References (48)

1. Abraham WR (2001) Bioactive sesquiterpenes produced by fungi: are they useful for humans as well? Curr Med Chem 8:583-606
2. Agger S, Lopez-Gallego F, Schmidt-Dannert C (2009) Diversity of sesquiterpene synthases in the basidiomycete Coprinus cinereus. Mol Microbiol 72:1181-1195
3. Ajikumar PK, Tyo K, Carlsen S, Mucha O, Phon TH, Stephanopoulos G (2008) Terpenoids: opportunities for biosynthesis of natural product drugs using engineered microorganisms. Mol Pharm 5:167-190 (Pubitemid 351579123)
4. Alves AMCR, Record E, Lomascolo A, Scholtmeijer K, Asther M, Wessels JGH, Wösten HAB (2004) Highly efficient production of laccase in the basidiomycete Pycnoporus cinnabarinus. Appl Environ Microbiol 70:6379-6384 (Pubitemid 39518540)
5. Asadollahi MA, Maury J, Møller K, Nielsen KF, Schalk M, Clark A, Nielsen J (2008) Production of plant sesquiterpenes in Saccharomyces cerevisiae: effect of ERG9 repression on sesquiterpene biosynthesis. Biotechnol Bioeng 99:666-677 (Pubitemid 351158264)
6. Beekwilder J, van Houwelingen A, Cankar K, van Dijk ADJ, de Jong RM, Stoopen G, Bouwmeester H, Achkar J, Sonke T, Bosch D (2013) Valencene synthase from the heartwood of Nootka cypress (Callitropsis nootkatensis) for biotechnological production of valencene. Plant Biotechnol J. doi:10.1111/pbi.12124
7. Calvo AM, Wilson RA, Bok JW, Keller NP (2002) Relationship between secondary metabolism and fungal development. Microbiol Mol Biol Rev 66:447-459 (Pubitemid 35001139)
8. Cankar K, Van Houwelingen A, Bosch D, Sonke T, Bouwmeester H, Beekwilder J (2011) A chicory cytochrome P450 mono-oxygenase CYP71AV8 for the oxidation of (+)-valencene. FEBS Lett 585:178-182
9. De Kraker J-W, Franssen MCR, Dalm MCF, De Groot A, Bouwmeester HJ (2001) Biosynthesis of germacrene A carboxylic acid in chicory roots. Demonstration of a cytochrome P450 (+)-germacrene A hydroxylase and NADP+ - dependent sesquiterpenoid dehydrogenase(s) involved in sesquiterpene lactone biosynthesis. Plant Physiol 125:1930-1940 (Pubitemid 32375775)
10. Demain AL (1986) Regulation of secondary metabolism in fungi. Pure Appl Chem 58:219-226
11. Dons JJM, De Vries OMH, Wessels JGH (1979) Characterisation of the genome of the basidiomycete Schizophyllum commune. Biochim Biophys Acta 563:100-112
12. Fahri M, Marhevka E, Masci T, Marcos E, Eyal Y, Ovadis M, Abeliovich H, Vainstein A (2011) Harnessing yeast subcellular compartments for the production of plant terpenoids. Metab Eng 13:474-481
13. Fowler TJ, Mitton FM (2000) Scooter, a new active transposon in Schizophyllum commune, has disrupted two genes regulating signal transduction. Genetics 156:1585-1594 (Pubitemid 32001227)
14. Fowler TJ, DeSimone SM, Mitton MF, Kurjan J, Raper CA (1999) Multiple sex pheromones and receptors of a mushroom-producing fungus elicit mating in yeast. Mol Biol Cell 10:2559-2572 (Pubitemid 29393510)
15. Fraatz MA, Riemera SJL, Stöber R, Kaspera R, Nimtz M, Berger RG, Zorn H (2009a) A novel oxygenase from Pleurotus sapidus transforms valencene to nootkatone. J Mol Catal B: Enzym 61:202-207
16. Fraatz MA, Berger RG, Zorn H (2009b) Nootkatone-a biotechnological challenge. Appl Microbiol Biotechnol 83:35-41
17. Gershenzon J, Dudareva N (2007) The function of terpene natural products in the natural world. Nat Chem Biol 3:408-414 (Pubitemid 46956324)
18. Kappers IF, Aharoni A, van Herpen TW, Luckerhoff LL, Dicke M, Bouwmeester HJ (2005) Genetic engineering of terpenoid metabolism attracts bodyguards to Arabidopsis. Science 309:2070 -2072
19. Kirby J, Keasling JD (2008) Metabolic engineering of microorganisms for isoprenoid production. Nat Prod Rep 25:656-661
20. Köhler RH, Zipfel WR, Webb WW, Hanson MR (1997) The green fluorescent protein as a marker to visualize plant mitochondria in vivo. Plant J 11:613-621 (Pubitemid 27158966)
21. Li L, Wright SJ, Krystofova S, Park G, Borkovich KA (2007) Heterotrimeric G protein signaling in filamentous fungi. Annu Rev Microbiol 61:423-452 (Pubitemid 350058216)
22. Liu Q, Majdi M, Cankar K, Goedbloed M, Charnikhova T, Verstappen FWA, de Vos RCH, Beekwilder J, van der Krol S, Bouwmeester HJ (2011) Reconstitution of the costunolide biosynthetic pathway in yeast and Nicotiana benthamiana. PLoS One 6:e23255
23. Lugones L, Scholtmeijer K, Klootwijk R, Wessels JGH(1999) Introns are necessary for mRNA accumulation in Schizophyllum commune. Mol Microbiol 32:681-689 (Pubitemid 29241510)
24. Martin D, Piulachs M-D, Cunillera N, Ferrer A, Bellés X (2007) Mitochondrial targeting of farnesyl diphosphate synthase is a widespread phenomenon in eukaryotes. Biochim Biophys Acta 1773:419-426 (Pubitemid 46275068)
25. Misawa N (2011) Pathway engineering for functional isoprenoids. Curr Opin Biotechnol 22:627-633
26. Ohm RA, De Jong JF, Lugones L, Aerts A, Kothe E, Stajich JE, De Vries RP, Record E, Levasseur A, Baker SE, Bartholomew KA, Coutinho PM, Erdmann S, Fowler TJ, Gathman AC, Lombard V, Henrissat B, Knabe N, Kües U, Lilly WW, Lindquist E, Lucas S, Magnuson JK, Piumi F, Raudaskoski M, Salamov A, Schmutz J, Schwarze FWMR, Van Kuyk PA, Horton JS, Grigoriev IV, Wösten HAB (2010a) Genome sequence of the model mushroom Schizophyllum commune. Nat Biotechnol 28:957-963
27. Ohm RA, De Jong JF, Berends E, Wang F, Wösten HAB, Lugones LG (2010b) An efficient gene deletion procedure for the mushroom-forming basidiomycete Schizophyllumcommune.World J Microbiol Biotechnol 10:1919-1923
28. Ohm RA, De Jong JF, De Bekker C, Wösten HAB, Lugones L (2011) Transcription factor genes of Schizophyllum commune involved in regulation of mushroom formation. Mol Microbiol 81:1433-1445
29. Raper JR, Miles PG (1958) The genetics of Schizophyllum commune. Genetics 43:530-546
30. Ro D-K, Paradise EM, Ouelle M, Fisher KJ, Newman KL, Ndungu JM, Ho KA, Eachus RA, Ham TS, Kirby J, Chang MCY, Withers ST, Shiba Y, Sarpong R, Keasling JD (2006) Production of the antimalarial drug precursor artemisinic acid in engineered yeast. Nature 440:940-943
31. Scholtmeijer K, Wösten HAB, Springer J, Wessels JGH (2001) Effect of introns and AT-rich sequences on expression of the bacterial hygromycin B resistance gene in the basidiomycete Schizophyllum commune. Appl Environ Microbiol 67:481-483 (Pubitemid 32044457)
32. Schuurs TA (1998) Regulation of hydrophobin genes in Schizophyllum commune. PhD Thesis, University of Groningen
33. Schwalb MN, Miles PG (1967) Morphogenesis of Schizophyllum commune. I. Morphological variation and mating behaviour of the thin mutation. Am J Bot 54:440-446
34. Seifert A, Vomund S, Grohmann K, Kriening S, Urlacher VB, Laschat S, Pleiss J (2009) Rational design of a minimal and highly enriched CYP102A1 mutant library with improved regio-, stereo-, and chemoselectivity. Chembiochem 10:853-861
35. Sowden RJ, Yasmin S, Rees NH, Bell SG, Wong LL (2005) Biotransformation of the sesquiterpene (+)-valencene by cytochrome P450cam and P450BM-3. Org Biomol Chem 3:57-64 (Pubitemid 40086162)
36. Spiteller P (2008) Chemical defense strategies of higher fungi. Chem Eur J 14:9100-9110
37. Tong P, Hong Y, Xiao Y, Zhang M, Tu X, Cui T (2007) High production of laccase by a new basidiomycete, Trametes sp. Biotechnol Lett 29:295-301 (Pubitemid 46089485)
38. Tsuruta H, Paddon CJ, Eng D, Lenihan JR, Horning T, Anthony LC, Regentin R, Keasling JD, Renninger NS, Newman JD (2009) High-level production of amorpha-4,11-diene, a precursor of the antimalarial agent artemisinin, in Escherichia coli. PLoS One 4:e4489
39. Van Herpen TWJM, Cankar K, Nogueira M, Bosch D, Bouwmeester HJ, Beekwilder J (2010) Nicotiana benthamiana as a production platform for artemisinin precursors. PLoS One 5:e14222
40. Van Peer AF, De Bekker C, Vinck A, Wösten HAB, Lugones LG (2009) Phleomycin increases transformation efficiency and promotes single integrations in Schizophyllum commune. Appl Environ Microbiol 75:1243-1247
41. Van Wetter M-A, Schuren FHJ, Schuurs TA, Wessels JGH (1996) Targeted mutation of the SC3 hydrophobin gene of Schizophyllum commune affects formation of aerial hyphae. FEMS Microbiol Lett 140:265-269 (Pubitemid 26228637)
42. Wessels JGH, de Vries OMH, Ásgeirsdóttir SA, Spinger J (1991) The THN mutation of Schizophyllum commune, which suppresses formation of aerial hyphae, affects expression of the SC3-hydrophobin gene. J Gen Microbiol 137:2439-2445
43. White S, McIntyre M, Berry DR, McNeil B (2002) The autolysis of industrial filamentous fungi. Crit Rev Biotechnol 22:1-14 (Pubitemid 34270980)
44. Wösten HAB, Schuren FHJ, Wessels JGH (1994) Interfacial self-assembly of a hydrophobin into an amphipathic membrane mediates fungal attachment to hydrophobic surfaces. EMBO J 13:5848-5854
45. Wu S, Schalk M, Clark A, Miles RB, Coates R, Chappel J (2006a) Redirection of cytosolic or plastidic isoprenoid precursors elevates terpene production in plants. Nat Biotechnol 24:1441-1447 (Pubitemid 44722109)
46. Wu G, Zheng Y, Qureshi I, Zin HT, Beck T, Bulka B, Freeland SJ (2006b) SGDB: a database of synthetic genes re-designed for optimizing protein over-expression. Nucleic Acids Res 35(database issue):D76-D79
47. Yu J-H, Keller N (2005) Regulation of secondary metabolism in filamentous fungi. Annu Rev Phytopathol 43:437-458 (Pubitemid 41318879)
48. Ziegenbein FC, Hanssen H-P, König WA (2006) Chemical constituents of the essential oils of threewood-rotting fungi. Flavour Frag J 21:813-816 (Pubitemid 44349545)