Terpene synthases are widely distributed in bacteria

Proceedings of the National Academy of Sciences of the United States of America

Volumn 112, Issue 3, 2015, Pages 857-862

  Yamada, Yuuki ^a   Kuzuyama, Tomohisa ^b   Komatsu, Mamoru ^a   Shin ya, Kazuo ^c   Omura, Satoshi ^a   Cane, David E ^d   Ikeda, Haruo ^a  

^a KITASATO UNIVERSITY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

^c NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^d BROWN UNIVERSITY   (United States)

Author keywords

Bacteria; Heterologous expression; Terpene synthase

Indexed keywords

ALCOHOL; DITERPENE; GEOSMIN; SESQUITERPENE; SYNTHETASE; TERPENE; TERPENE DERIVATIVE; TERPENE SYNTHASE; TERPENOID; UNCLASSIFIED DRUG; TRANSFERASE;

ARTICLE; BACTERIA; DATA BASE; GENE; GENE SEQUENCE; GENOME; METABOLITE; NONHUMAN; PRIORITY JOURNAL; PROTEIN FAMILY; STREPTOMYCES; STREPTOMYCETACEAE; BACTERIUM; ENZYMOLOGY; MARKOV CHAIN; METABOLISM;

BACTERIA (MICROORGANISMS); STREPTOMYCES; STREPTOMYCETACEAE;

ALKYL AND ARYL TRANSFERASES; BACTERIA; MARKOV CHAINS;

EID: 84921327913     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.1422108112     Document Type: Article

References (54)

1. Berthelot M, André G (1891) Sur l'odeur proper de la terre. C R Acad Sci 112(1):598-599.
2. Gerber NN, Lechevalier HA (1965) Geosmin, an earthly-smelling substance isolated from actinomycetes. Appl Microbiol 13(6):935-938.
3. Gerber NN (1967) Geosmin, an earthy-smelling substance isolated from actinomycetes. Biotechnol Bioeng 9(3):321-327.
4. Gerber NN (1969) A volatile metabolite of actinomycetes, 2-methylisoborneol. J Antibiot (Tokyo) 22(10):508-509.
5. Gerber NN (1971) Sesquiterpenoids from Actinomycetes: Cadin-4en-1-ol. Phytochemistry 10(1):185-189.
6. Gerber NN (1972) Sesquiterpenoids from actinomycetes. Phytochemistry 11(1):385-388.
7. Gerber NN (1973) Volatile lactones from Streptomyces. Tetrahedron Lett 14(10):771-774.
8. Pollak FC, Berger RG (1996) Geosmin and related volatiles in bioreactor-cultured Streptomyces citreus CBS 109.60. Appl Environ Microbiol 62(4):1295-1299.
9. Jáchymová J, Votruba J, Víden I, Rezanka T (2002) Identification of Streptomyces odor spectrum. Folia Microbiol (Praha) 47(1):37-41.
10. Wilkins K, Schöller C (2009) Volatile organic metabolites from selected Streptomyces strains. Actinomycetologica 23(2):27-33.
11. Schöller CE, Gürtler H, Pedersen R, Molin S, Wilkins K (2002) Volatile metabolites from actinomycetes. J Agric Food Chem 50(9):2615-2621.
12. Dickschat JS, Wenzel SC, Bode HB, Müller R, Schulz S (2004) Biosynthesis of volatiles by the myxobacterium Myxococcus xanthus. ChemBioChem 5(6):778-787.
13. Dickschat JS, Bode HB, Wenzel SC, Müller R, Schulz S (2005) Biosynthesis and identification of volatiles released by the myxobacterium Stigmatella aurantiaca. Chem-BioChem 6(11):2023-2033.
14. Dickschat JS, Martens T, Brinkhoff T, Simon M, Schulz S (2005) Volatiles released by a Streptomyces species isolated from the North Sea. Chem Biodivers 2(7):837-865.
15. Schulz S, Dickschat JS (2007) Bacterial volatiles: The smell of small organisms. Nat Prod Rep 24(4):814-842.
16. Rabe P, Citron CA, Dickschat JS (2013) Volatile terpenes from actinomycetes: A biosynthetic study correlating chemical analyses to genome data. ChemBioChem 14(17):2345-2354.
17. Gerber NN (1979) Volatile substances from actinomycetes: Their role in the odor pollution of water. CRC Crit Rev Microbiol 7(3):191-214.
18. Izaguirre G, Hwang CJ, Krasner SW, McGuire MJ (1982) Geosmin and 2-methylisoborneol from cyanobacteria in three water supply systems. Appl Environ Microbiol 43(3):708-714.
19. Jüttner F (1987) Volatile organic substances. The Cyanobacteria, eds Fay B, Baalen CV (Elsevier, Amsterdam), pp 453-469.
20. Wu J-T, Jüttner F (1988) Differential partitioning of geosmin and 2-methylisoborneol between cellular constituents in Oscillatoria tenuis. Arch Microbiol 150(6):580-583.
21. Dickschat JS, et al. (2007) Biosynthesis of the off-flavor 2-methylisoborneol by the myxobacterium Nannocystis exedens. Angew Chem Int Ed Engl 46(43):8287-8290.
22. Mattheis JP, Roberts RG (1992) Identification of geosmin as a volatile metabolite of Penicillium expansum. Appl Environ Microbiol 58(9):3170-3172.
23. Börjesson T, Stöllman U, Schnürer J (1993) Off odors compounds produced by molds on oatmeal agar: Identification and relation to other growth characteristics. J Agric Food Chem 41(11):2104-2111.
24. Larsen TO, Frisvad JC (1995) Characterization of volatile metabolites from 47 Penicillium taxa. Mycol Res 99(10):1153-1166.
25. Gürtler H, et al. (1994) Albaflavenone, a sesquiterpene ketone with a zizaene skeleton produced by a streptomycete with a new rope morphology. J Antibiot (Tokyo) 47(4):434-439.
26. Finn RD, et al. (2010) The Pfam protein families database. Nucleic Acids Res 38(Database issue):D211-D222.
27. Komatsu M, Tsuda M, Omura S, Oikawa H, Ikeda H (2008) Identification and functional analysis of genes controlling biosynthesis of 2-methylisoborneol. Proc Natl Acad Sci USA 105(21):7422-7427.
28. Giglio S, Chou WKW, Ikeda H, Cane DE, Monis PT (2011) Biosynthesis of 2-methylisoborneol in cyanobacteria. Environ Sci Technol 45(3):992-998.
29. Whittington DA, et al. (2002) Bornyl diphosphate synthase: Structure and strategy for carbocation manipulation by a terpenoid cyclase. Proc Natl Acad Sci USA 99(24): 15375-15380.
30. Yamada Y, Cane DE, Ikeda H (2012) Diversity and analysis of bacterial terpene synthases. Natural Product Biosynthesis by Microorganisms and Plants, Part A. Methods in Enzymology, ed Hopwood DA (Elsevier Inc/Academic Press, New York), Vol 515, pp 123-166.
31. Koe BK, Sobin BA, Celmer WD (1956-1957) PA 132, a new antibiotic. I. Isolation and chemical properties. Antibiot Annu 1956-1957(1956-1957):672-675.
32. Takahashi S, Takeuchi M, Arai M, Seto H, Otake N (1983) Studies on biosynthesis of pentalenolactone. V isolation of deoxypentalenylglucuron. J Antibiot (Tokyo) 36(3):226-228.
33. Cane DE, Abell C, Tillman AM (1984) Pentalenene biosynthesis and the enzymatic cyclization of farnesyl pyrophosphate. Proof that the cyclization is catalyzed by a single enzyme. Bioorg Chem 12(4):312-328.
34. Lesburg CA, Zhai G, Cane DE, Christianson DW (1997) Crystal structure of pentalenene synthase: Mechanistic insights on terpenoid cyclization reactions in biology. Science 277(5333):1820-1824.
35. Tetzlaff CN, et al. (2006) A gene cluster for biosynthesis of the sesquiterpenoid antibiotic pentalenolactone in Streptomyces avermitilis. Biochemistry 45(19):6179-6186.
36. Jiang J, et al. (2009) Genome mining in Streptomyces avermitilis: A biochemical Baeyer-Villiger reaction and discovery of a new branch of the pentalenolactone family tree. Biochemistry 48(27):6431-6440.
37. Seo M-J, Zhu D, Endo S, Ikeda H, Cane DE (2011) Genome mining in Streptomyces. Elucidation of the role of Baeyer-Villiger monooxygenases and non-heme irondependent dehydrogenase/oxygenases in the final steps of the biosynthesis of pentalenolactone and neopentalenolactone. Biochemistry 50(10):1739-1754.
38. Ikeda H, Shin-ya K, Omura S (2014) Genome mining of the Streptomyces avermitilis genome and development of genome-minimized hosts for heterologous expression of biosynthetic gene clusters. J Ind Microbiol Biotechnol 41(2):233-250.
39. Zhu D, Seo M-J, Ikeda H, Cane DE (2011) Genome mining in streptomyces. Discovery of an unprecedented P450-catalyzed oxidative rearrangement that is the final step in the biosynthesis of pentalenolactone. J Am Chem Soc 133(7):2128-2131.
40. Nakano C, Horinouchi S, Ohnishi Y (2011) Characterization of a novel sesquiterpene cyclase involved in (+)-caryolan-1-ol biosynthesis in Streptomyces griseus. J Biol Chem 286(32):27980-27987.
41. Nakano C, Tezuka T, Horinouchi S, Ohnishi Y (2012) Identification of the SGR6065 gene product as a sesquiterpene cyclase involved in (+)-epicubenol biosynthesis in Streptomyces griseus. J Antibiot (Tokyo) 65(11):551-558.
42. Cane DE, He X, Kobayashi S, Omura S, Ikeda H (2006) Geosmin biosynthesis in Streptomyces avermitilis. Molecular cloning, expression, and mechanistic study of the germacradienol/geosmin synthase. J Antibiot (Tokyo) 59(8):471-479.
43. Takamatsu S, et al. (2011) Characterization of a silent sesquiterpenoid biosynthetic pathway in Streptomyces avermitilis controlling epi-isozizaene albaflavenone biosynthesis and isolation of a new oxidized epi-isozizaene metabolite. Microb Biotechnol 4(2):184-191.
44. Chou WKW, et al. (2010) Genome mining in Streptomyces avermitilis: Cloning and characterization of SAV-76, the synthase for a new sesquiterpene, avermitilol. J Am Chem Soc 132(26):8850-8851.
45. Komatsu M, Uchiyama T, Omura S, Cane DE, Ikeda H (2010) Genome-minimized Streptomyces host for the heterologous expression of secondary metabolism. Proc Natl Acad Sci USA 107(6):2646-2651.
46. Komatsu M, et al. (2013) Engineered Streptomyces avermitilis host for heterologous expression of biosynthetic gene cluster for secondary metabolites. ACS Synth Biol 2(7):384-396.
47. Nakano C, Kim H-K, Ohnishi Y (2011) Identification of the first bacterial monoterpene cyclase, a 1,8-cineole synthase, that catalyzes the direct conversion of geranyl diphosphate. ChemBioChem 12(13):1988-1991.
48. Hu Y, Chou WKW, Hopson R, Cane DE (2011) Genome mining in Streptomyces clavuligerus : Expression and biochemical characterization of two new cryptic sesquiterpene synthases. Chem Biol 18(1):32-37.
49. Agger SA, Lopez-Gallego F, Hoye TR, Schmidt-Dannert C (2008) Identification of sesquiterpene synthases from Nostoc punctiforme PCC 73102 and Nostoc sp. strain PCC 7120. J Bacteriol 190(18):6084-6096.
50. Kohl AC, Kerr RG (2003) Pseudopterosin biosynthesis: Aromatization of the diterpene cyclase product, elisabethatriene. Mar Drugs 1(1):54-65.
51. Li L, et al. (2011) Diterpenes from the Hainan soft coral Lobophytum cristatum Tixier-Durivault. J Nat Prod 74(10):2089-2094.
52. Hellwig V, et al. (1998) New triquinane-type sesquiterpenoids from Macrocystidia cucumis (Basidiomycetes). Eur J Org Chem 1998(1):73-79.
53. Kim S-Y, et al. (2009) Cloning and heterologous expression of the cyclooctatin biosynthetic gene cluster afford a diterpene cyclase and two p450 hydroxylases. Chem Biol 16(7):736-743.
54. Yamada Y, et al. (2014) Novel terpenes generated by heterologous expression of bacterial terpene synthase genes in an engineered Streptomyces host. J Antibiot (Tokyo), in press.