Cyclization of all-E- and 2Z-geranylfarnesols by a bacterial triterpene synthase: Insight into sesterterpene biosynthesis in aleuritopteris ferns

Bioscience, Biotechnology and Biochemistry

Volumn 77, Issue 11, 2013, Pages 2278-2282

  Shinozaki, Junichi ^a   Shibuya, Masaaki ^b   Ebizuka, Yutaka ^c   Masuda, Kazuo ^a  

^a SHOWA PHARMACEUTICAL UNIVERSITY   (Japan)

^b NIIGATA UNIVERSITY OF PHARMACY AND APPLIED LIFE SCIENCES   (Japan)

^c UNIVERSITY OF TOKYO   (Japan)

Author keywords

Aleuritopteris spp; Fern; Sesterterpene; Triterpene synthase

Indexed keywords

ALEURITOPTERIS SPP; BIOSYNTHETIC ENZYMES; FERN; SESTERTERPENES; SYNTHASES; TRITERPENES;

BIOCHEMISTRY; MUSCULOSKELETAL SYSTEM;

BIOSYNTHESIS;

BACTERIAL PROTEIN; DRUG DERIVATIVE; GEFARNATE; GERANYLFARNESOL; LIGASE; RECOMBINANT PROTEIN; SESTERTERPENE; TRITERPENE;

ALICYCLOBACILLUS; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; ENZYME SPECIFICITY; ENZYMOLOGY; ESCHERICHIA COLI; FERN; GENETICS; METABOLISM; STEREOISOMERISM;

ALICYCLOBACILLUS; BACTERIAL PROTEINS; CYCLIZATION; ESCHERICHIA COLI; FERNS; GEFARNATE; LIGASES; MOLECULAR STRUCTURE; RECOMBINANT PROTEINS; SESTERTERPENES; STEREOISOMERISM; SUBSTRATE SPECIFICITY; TRITERPENES;

EID: 84888877969     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.130543     Document Type: Article

References (31)

1. Liu Y, Wang L, Jung JH, and Zhang S, Nat. Prod. Rep., 24, 1401-1429 (2007).
2. Chiba R, Minami A, Gomi K, and Oikawa H, Org. Lett., 15, 594-597 (2013).
3. Sato T, Yamaga H, Kashima S, Murata Y, Shinada T, Nakano C, and Hoshino T, ChemBioChem, 14, 822-825 (2013).
4. Kamaya R and Ageta H, Chem. Pharm. Bull., 38, 342-346 (1990).
5. Kamaya R, Masuda K, Suzuki K, Ageta H, and Hsü HY, Chem. Pharm. Bull., 44, 690-694 (1996).
6. Kamaya R, Masuda K, Ageta H, and Chang HC, Chem. Pharm. Bull., 44, 695-698 (1996).
7. Renoux JM and Rohmer M, Eur. J. Biochem., 155, 125-132 (1986).
8. Shinozaki J, Shibuya M, Masuda K, and Ebizuka Y, FEBS Lett., 582, 310-318 (2008).
9. Shinozaki J, Shibuya M, Masuda K, and Ebizuka Y, Phytochemistry, 69, 2559-2564 (2008).
10. Shinozaki J, Shibuya M, Takahata Y, Masuda K, and Ebizuka Y, ChemBioChem, 11, 426-433 (2010).
11. Sato T, Kanai Y, and Hoshino T, Biosci. Biotechnol. Biochem., 62, 407-411 (1998).
12. Hoshino T and Sato T, Chem. Commun., 291-301 (2002).
13. Abe I, Nat. Prod. Rep., 24, 1311-1331 (2007).
14. Ochs D, Kaletta C, Entian KD, Beck-Sickinger A, and Poralla K, J. Bacteriol., 174, 298-302 (1992).
15. Vig OP, Sharma SD, Bari SS, and Rana SS, Ind. J. Chem., 17B, 31-33 (1979).
16. Ungur MD, Nguyen VT, and Vlad PF, Chem. Nat. Compd., 26, 292-296 (1990).
17. Albizati KF, Holman T, Faulkner DJ, Glaser KB, and Jacobs RS, Experientia, 43, 949-950 (1987).
18. Herz W and Prasad JS, J. Org. Chem., 47, 4171-4173 (1982).
19. Nabeta K, Fujita M, Komuro K, Katayama K, and Takasawa T, J. Chem. Soc., Perkin Trans. 1, 2065-2070 (1997).
20. Sallaud C, Rontein D, Onillon S, Jabes F, Duffe P et al., Plant Cell, 21, 301-317 (2009).
21. Schilmiller AL, Schauvinhold I, Larson M, Xu R, Charbonneau AL, Schmidt A, Wilkerson C, Last RL, and Pichersky E, Proc. Natl. Acad. Sci. USA, 106, 10865-10870 (2009).
22. Bleeker PM, Mirabella R, Diergaarde PJ, VanDoorn A, Tissier A et al., Proc. Natl. Acad. Sci. USA, 109, 20124-20129 (2012).
23. Sato T, Takagi R, Orito Y, Ono E, and Hoshino T, Biosci. Biotechnol. Biochem., 74, 147-151 (2010).
24. Sato T, Takizawa K, Orito Y, Kudo H, and Hoshino T, ChemBioChem, 11, 1874-1881 (2010).
25. Sato T, Ono E, Nakajima M, Nakano C, and Hoshino T, Tetrahedron Lett., 53, 2522-2524 (2012).
26. Sato T, Hoshino H, Yoshida S, Nakajima M, and Hoshino T, J. Am. Chem. Soc., 133, 17540-17543 (2011).
27. Keeling CI, Weisshaar S, Ralph SG, Jancsik S, Hamberger B, Dullat HK, and Bohlmann J, BMC Plant Biol., 11, 43 (2011).
28. Davidovich-Rikanati R, Lewinsohn E, Bar E, Iijima Y, Pichersky E, and Sitrit Y, Plant J., 56, 228-238 (2008).
29. Lee S and Chappell J, Plant Physiol., 147, 1017-1033 (2008).
30. Green S, Friel EN, Matich A, Beuning LL, Cooney JM, Rowan DD, and MacRae E, Phytochemistry, 68, 176-188 (2007).
31. Landmann C, Fink B, Festner M, Dregus M, Engel K-H, and Schwab W, Arch. Biochem. Biophys., 465, 417-429 (2007).