Diterpene Synthases and Their Responsible Cyclic Natural Products
Hai-Yan Gong1,2, Ying Zeng1, Xiao-Ya Chen3
1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, 132 Lanhei Road, Kunming 650201, China; 2. University of Chinese Academy of Sciences, Beijing 100049, China; 3. National Key Laboratory of Plant Molecular Genetics, Institute of Plant Physiology and Ecology, Shanghai Institutes for Biological Sciences, Shanghai 200032, China
Abstract This review provides an overview of diterpene synthases which were initially identified via genetic and/or biochemical means, traversing all organisms researched to date.
Fund:This study was supported by grants from the National Key Laboratory of Plant Molecular Genetics, and from the State Key Laboratory of Phytochemistry and Plant Resources in West China.
1. D.W. Christianson, Chem. Rev. 106, 3412-3442 (2006) 2. R.J. Peters, Nat. Prod. Rep. 27, 1521-1530 (2010) 3. T. Dairi, Y. Hamano, T. Kuzuyama, N. Itoh, K. Furihata, H. Seto, J. Bacteriol. 183, 6085-6094 (2001) 4. Y. Hamano, T. Kuzuyama, N. Itoh, K. Furihata, H. Seto, T. Dairi, J. Biol. Chem. 277, 37098-37104 (2002) 5. C. Nakano, T. Okamura, T. Sato, T. Dairi, T. Hoshino, Chem. Commun. 8, 1016-1018 (2005) 6. C. Nakano, T. Hoshino, ChemBioChem 10, 2060-2071 (2009) 7. C. Nakano, T. Ootsuka, K. Takayama, T. Mitsui, T. Sato, T. Hoshino, Biosci. Biotechnol. Biochem. 75, 75-81 (2011) 8. S. Mafu, M.L. Hillwig, R.J. Peters, ChemBioChem 12, 1984-1987 (2011) 9. P. Zerbe, A. Chiang, M. Yuen, B. Hamberger, B. Hamberger, J.A. Draper, R. Britton, J. Bohlmann, J. Biol. Chem. 287, 12121-12131 (2012) 10. C. Sallaud, C. Giacalone, R. Topfer, S. Goepfert, N. Bakaher, S. Rosti, A. Tissier, Plant J. 72, 1-17 (2012) 11. V. Falara, E. Pichersky, A.K. Kanellis, Plant Physiol. 154, 301-310 (2010) 12. A. Caniard, P. Zerbe, S. Legran, A. Cohade, N. Valot, J.L. Magnard, J. Bohlmann, L. Legendre, BMC Plant Biol. 12, 119 (2012) 13. T. Kawasaki, T. Kuzuyama, Y. Kuwamori, N. Matsuura, N. Itoh, K. Furihata, H. Seto, T. Dairi, J. Antibiot. 57, 739-747 (2004) 14. C. Ikeda, Y. Hayashi, N. Itoh, H. Seto, T. Dairi, J. Biochem. 141, 37-45 (2007) 15. F.M. Mann, M. Xu, X. Chen, D.B. Fulton, D.G. Russell, R.J. Peters, J. Am. Chem. Soc. 131, 17526-17527 (2009) 16. M.J. Smanski, Z. Yu, J. Casper, S. Lin, R.M. Peterson, Y. Chen, E. Wendt-Pienkowski, S.R. Rajski, B. Shen, Proc. Natl. Acad. Sci. U.S.A. 108, 13498-13503 (2011) 17. M.J. Smanski, R.M. Peterson, S.-X. Huang, B. Shen, Curr. Opin. Chem. Biol. 16, 132-141 (2012) 18. S.Y. Kim, P. Zhao, M. Igarashi, R. Sawa, T. Tomita, M. Nishiyama, T. Kuzuyama, Chem. Biol. 16, 736-743 (2009) 19. T. Toyomasu, M. Tsukahara, A. Kaneko, R. Niida, W. Mitsuhashi, T. Dairi, N. Kato, T. Sassa, Proc. Natl. Acad. Sci. U.S.A. 104, 3084-3088 (2007) 20. A. Minami, N. Tajima, Y. Higuchi, T. Toyomasu, T. Sassa, N. Kato, T. Dairi, Bioorg. Med. Chem. Lett. 19, 870-874 (2009) 21. B.S. Vogel, M.R. Wildung, G. Vogel, R. Croteau, J. Biol. Chem. 271, 23262-23268 (1996) 22. D.M. Martin, J. Faldt, Bohlmann, J. Plant Physiol. 135, 1908-1927 (2004) 23. C.I. Keeling, L.L. Madilao, P. Zerbe, H.K. Dullat, J. Bohlmann, J. Biol. Chem. 286, 21145-21153 (2011) 24. H.G. Schepmann, J. Pang, S.P. Matsuda, Arch. Biochem. Biophys. 392, 263-269 (2001) 25. M.R. Wildung, R. Croteau, J. Biol. Chem. 271, 9201-9204 (1996) 26. R. Croteau, R.E.B. Ketchum, R.M. Long, R. Kaspera, M.R. Wildung, Phytochem. Rev. 5, 75-97 (2006) 27. W. Gao, M.L. Hillwig, L. Huang, G. Cui, X. Wang, J. Kong, B. Yang, R.J. Peters, Org. Lett. 11, 5170-5173 (2009) 28. S. Prisic, M. Xu, P.R. Wilderman, R. Peters, J. Plant Physiol. 136, 4228-4236 (2004) 29. K. Otomo, H. Kenmoku, H. Oikawa, W.A. Konig, H. Toshima, W. Mitsuhashi, H. Yamane, T. Sassa, T. Toyomasu, Plant J. 39, 886-893 (2004) 30. M. Xu, M.L. Hillwig, S. Prisic, R.M. Coates, R.J. Peters, Plant J. 39, 309-318 (2004) 31. E.M. Cho, A. Okada, H. Kenmoku, K. Otomo, T. Toyomasu, W. Mitsuhashi, T. Sassa, A. Yajima, G. Yabuta, K. Mori, H. Oikawa, H. Toshima, N. Shibuya, H. Nojiri, T. Omori, M. Nishiyama, H. Yamane, Plant J. 37, 1-8 (2004) 32. M. Xu, P.R. Wilderman, D. Morrone, J. Xu, A. Roy, M. MargisPinheiro, N.M. Upadhyaya, R.M. Coates, R.J. Peters, Phytochemistry 68, 312-326 (2007) 33. K. Otomo, Y. Kanno, A. Motegi, H. Kenmoku, H. Yamane, W. Mitsuhashi, H. Oikawa, H. Toshima, H. Itoh, M. Matsuoka, T. Sassa, T. Toyomasu, Biosci. Biotechnol. Biochem. 68, 2001-2006 (2004) 34. Y. Kanno, K. Otomo, H. Kenmoku, W. Mitsuhashi, H. Yamane, H. Oikawa, H. Toshima, M. Matsuoka, T. Sassa, T. Toyomasu, Biosci. Biotechnol. Biochem. 70, 1702-1710 (2006) 35. M. Xu, P.R. Wilderman, R.J. Peters, Proc. Natl. Acad. Sci. U.S.A. 104, 7397-7401 (2007) 36. P.R. Wilderman, M. Xu, Y. Jin, R.M. Coates, R. Peters, J. Plant Physiol. 135, 2098-2105 (2004) 37. A.C. Kohl, R.G. Kerr, Arch. Biochem. Biophys. 424, 97-104 (2004) 38. T.B. Brück, R.G. Kerr, Comp. Biochem. Physiol. B-Biochem. Mol. Biol. 143, 269-278 (2006) 39. D. Morrone, J. Chambers, L. Lowry, G. Kimc, A. Anterola, K. Bender, R.J. Peters, FEBS Lett. 583, 475-480 (2009) 40. H. Kawaide, R. Imai, T. Sassa, Y. Kamiya, J. Biol. Chem. 272, 21706-21712 (1997) 41. H. Oikawa, T. Toyomasu, H. Toshima, S. Ohashi, H. Kawaide, Y. Kamiya, M. Ohtsuka, S. Shinoda, W. Mitsuhashi, T. Sassa, J. Am. Chem. Soc. 123, 5154-5155 (2001) 42. T. Toyomasu, R. Niida, H. Kenmoku, Y. Kanno, S. Miura, C. Nakano, Y. Shiono, W. Mitsuhashi, H. Toshima, H. Oikawa, T. Hoshino, T. Dairi, N. Kato, T. Sassa, Biosci. Biotechnol. Biochem. 72, 1038-1047 (2008) 43. T. Toyomasu, A. Kaneko, T. Tokiwano, Y. Kanno, Y. Kanno, R. Niida, S. Miura, T. Nishioka, C. Ikeda, W. Mitsuhashi, T. Dairi, T. Kawano, H. Oikawa, N. Kato, T. Sassa, J. Org. Chem. 74, 1541-1548 (2009) 44. K. Hayashi, H. Kawaide, M. Notomi, Y. Sakigi, A. Matsuo, H. Nozaki, FEBS Lett. 580, 6175-6181 (2006) 45. K. Hayashi, K. Horie, Y. Hiwatashi, H. Kawaide, S. Yamaguchi, A. Hanada, T. Nakashima, M. Nakajima, L.N. Mander, H. Yamane, M. Hasebe, H. Nozaki, Plant Physiol. 153, 1085-1097 (2010) 46. H. Kawaide, K. Hayashi, R. Kawanabe, Y. Sakigi, A. Matsuo, M. Natsume, H. Nozaki, FEBS J. 278, 123-133 (2011) 47. T.P. Sun, Y. Kamiya, Plant Cell 6, 1509-1518 (1994) 48. S. Yamaguchi, T. Saito, H. Abe, H. Yamane, N. Murofushi, Y. Kamiya, Plant J. 10, 203-213 (1996) 49. A.S. Richman, M. Gijzen, A.N. Starratt, Z.Y. Yang, J.E. Brandle, Plant J. 19, 411-421 (1999) 50. J.L. Li, Q.Q. Chen, Q.P. Jin, J. Gao, P.J. Zhao, S. Lu, Y. Zeng, Phytochemistry 76, 32-39 (2012) 51. L.J. Harris, A. Saparno, A. Johnston, S. Prisic, M. Xu, S. Allard, A. Kathiresan, T. Ouellet, R.J. Peters, Plant Mol. Biol. 59, 881-894 (2005) 52. E.A. Schmelz, F. Kaplan, A. Huffaker, N.J. Dafoe, M.M. Vaughan, X. Ni, J.R. Rocca, H.T. Alborn, P.E. Teal, Proc. Natl. Acad. Sci. U.S.A. 108, 5455-5460 (2011) 53. T. Nemoto, E.M. Cho, A. Okada, K. Okada, K. Otomo, Y. Kanno, T. Toyomasu, W. Mitsuhashi, T. Sassa, E. Minami, N. Shibuya, M. Nishiyama, H. Nojiri, H. Yamane, FEBS Lett. 571, 182-186 (2004) 54. D. Morrone, Y. Jin, M. Xu, S.Y. Choi, R.M. Coates, R.J. Peters, Arch. Biochem. Biophys. 448, 133-140 (2006) 55. J. Kirby, M. Nishimoto, J.G. Park, S.T. Withers, F. Nowroozi, D. Behrendt, E.J.G. Rutledge, J.L. Fortman, H.E. Johnson, J.V. Anderson, J.D. Keasling, Phytochemistry 71, 1466-1473 (2010) 56. A. Meguro, T. Tomita, M. Nishiyama, T. Kuzuyama, ChemBioChem 14, 316-321 (2013) 57. E. Wang, G.J. Wagner, Planta 216, 686-691 (2003) 58. D. Sitton, C. West, A. Phytochemistry 14, 1921-1925 (1975) 59. C.J. Mau, C.A. West, Proc. Natl. Acad. Sci. U.S.A. 91, 8497-8501 (1994)
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