Diterpene Synthases and Their Responsible Cyclic Natural Products

doi:10.1007/s13659-014-0012-8

应用天然产物 ›› 2014, Vol. 4 ›› Issue (2): 59-72.DOI: 10.1007/s13659-014-0012-8

• Review • 下一篇

Diterpene Synthases and Their Responsible Cyclic Natural Products

Hai-Yan Gong^1,2, 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

收稿日期:2014-01-20 修回日期:2014-03-23 出版日期:2014-04-24 发布日期:2018-02-11
通讯作者: Ying Zeng,e-mail:biochem@mail.kib.ac.cn
基金资助:
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.

Diterpene Synthases and Their Responsible Cyclic Natural Products

Hai-Yan Gong^1,2, 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

Received:2014-01-20 Revised:2014-03-23 Online:2014-04-24 Published:2018-02-11
Supported by:
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.

摘要/Abstract

摘要： This review provides an overview of diterpene synthases which were initially identified via genetic and/or biochemical means, traversing all organisms researched to date.

关键词: Biosynthesis, cDNA, Cyclase, Diterpenoid, Eriocalyxin B

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.

Key words: Biosynthesis, cDNA, Cyclase, Diterpenoid, Eriocalyxin B

Hai-Yan Gong, Ying Zeng, Xiao-Ya Chen. Diterpene Synthases and Their Responsible Cyclic Natural Products[J]. 应用天然产物, 2014, 4(2): 59-72.

Hai-Yan Gong, Ying Zeng, Xiao-Ya Chen. Diterpene Synthases and Their Responsible Cyclic Natural Products[J]. Natural Products and Bioprospecting, 2014, 4(2): 59-72.

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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Diterpene Synthases and Their Responsible Cyclic Natural Products

Diterpene Synthases and Their Responsible Cyclic Natural Products

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