Diterpene Synthases and Their Responsible Cyclic Natural Products

doi:10.1007/s13659-014-0012-8

Natural Products and Bioprospecting

2014, Vol. 4

Issue (2) : 59-72 DOI: 10.1007/s13659-014-0012-8

Review

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

Abstract
References
Related Articles
Metrics

Download: PDF(4647 KB) HTML (171)
Export: BibTeX | EndNote | Reference Manager | ProCite | RefWorks

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.

Keywords Biosynthesis cDNA Cyclase Diterpenoid Eriocalyxin B

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.

Issue Date: 11 February 2018

	Service

	E-mail this article
	E-mail Alert
	RSS
	Articles by authors

	Hai-Yan Gong
	Ying Zeng
	Xiao-Ya Chen

Trendmd:

Cite this article:

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.

URL:

http://npb.kib.ac.cn/EN/10.1007/s13659-014-0012-8 OR http://npb.kib.ac.cn/EN/Y2014/V4/I2/59

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)

[1]	Xing Yu, Kai-Ting Duan, Zhen-Xiong Wang, He-Ping Chen, Xiao-Qing Gan, Rong Huang, Zheng-Hui Li, Tao Feng, Ji-Kai Liu. Anemhupehins A-C, Podocarpane Diterpenoids from Anemone hupehensis[J]. Natural Products and Bioprospecting, 2018, 8(1): 31-35.
[2]	Ya-Mei Li, Bing Xiang, Xiao-Zheng Li, Yong-Ming Yan, Yong-Xian Cheng. New Diterpenoids from Clerodendranthus spicatus[J]. Natural Products and Bioprospecting, 2017, 7(3): 263-267.
[3]	Rui Chu, Luo-Sheng Wan, Xing-Rong Peng, Mu-Yuan Yu, Zhi-Run Zhang, Lin Zhou, Zhong-Rong Li, Ming-Hua Qiu. *Characterization of New Ent-kaurane Diterpenoids of Yunnan Arabica Coffee Beans*[J]. Natural Products and Bioprospecting, 2016, 6(4): 217-223.
[4]	Hui Zhou, Yan-Long Yang, Jun Zeng, Ling Zhang, Zhi-Hui Ding, Ying Zeng. *Identification and Characterization of a d-Cadinol Synthase Potentially Involved in the Formation of Boreovibrins in Boreostereum vibrans* of Basidiomycota**[J]. Natural Products and Bioprospecting, 2016, 6(3): 167-171.
[5]	Bing-Dong Lin, Bin Zhou, Lei Dong, Yan Wu, Jian-Min Yue. Formosins A-F: Diterpenoids with Anti-microbial Activities from Excoecaria formosana[J]. Natural Products and Bioprospecting, 2016, 6(1): 57-61.
[6]	Tian-Peng Yin,Le Cai,Ying Li,Yun-Shan Fang, Li Peng,Zhong-Tao Ding. New Alkaloids from Aconitum stapfianum[J]. Natural Products and Bioprospecting, 2015, 5(6): 271-275.
[7]	Fan Xia,Chun-Yan Wu,Xing-Wei Yang, Xian Li,Gang Xu. Diterpenoids from the Roots of Salvia yunnanensis[J]. Natural Products and Bioprospecting, 2015, 5(6): 307-312.
[8]	Qiu-Li Xiao, Fan Xia, Xing-Wei Yang, Yang Liao, Li-Xin Yang, Yu-Kun Wei, Xian Li, Gang Xu. New Dimeric and seco-Abietane Diterpenoids from Salvia wardii[J]. Natural Products and Bioprospecting, 2015, 5(2): 77-82.
[9]	Ya-Mei Pan, Yu Zhang, Xiao-Nan Wang, He-Ping Chen, Shun-Lin Li, Ying-Tong Di, Duo-Zhi Chen, Ling-Li Guo, Xiao-Jiang Hao, Hong-Ping He. Chemical Constituents from the Stems of Manihot esculenta[J]. Natural Products and Bioprospecting, 2015, 5(1): 55-59.
[10]	Chun-Shuai Huang, Shi-Hong Luo, Yao-Lan Li, Chun-Huan Li, Juan Hua, Yan Liu, Shu-Xi Jing, Ying Wang, Min-Jie Yang, Sheng-Hong Li. Antifeedant and Antiviral Diterpenoids from the Fresh Roots of Euphorbia jolkinii[J]. Natural Products and Bioprospecting, 2014, 4(2): 91-100.
[11]	Wei-Ming Zhang, Jie-Qing Liu, Yuan-Yuan Deng, Jian-Jun Xia, Zhi-Run Zhang, Zhong-Rong Li, Ming-Hua Qiu. Diterpenoids and Limonoids from the Leaves and Twigs of Swietenia mahagoni[J]. Natural Products and Bioprospecting, 2014, 4(1): 53-57.
[12]	Yuan GAO, Yin-Dong FANG, Ping HAI, Fei WANG, Ji-Kai LIU. Isoprenylated flavonoids and clerodane diterpenoids from Dodonaea viscosa[J]. Natural Products and Bioprospecting, 2013, 3(5): 250-255.
[13]	Wei-Guang WANG, Xue DU, Xiao-Nian LI, Bing-Chao YAN, Min ZHOU, Hai-Yan WU, Rui ZHAN, Ke DONG, Jian-Xin PU, Han-Dong SUN. Four new diterpenoids from Isodon eriocalyx var. laxiflora[J]. Natural Products and Bioprospecting, 2013, 3(4): 145-149.
[14]	Bing-Ji Ma, Chun-Nan Wen, Yuan Gao, Fu-Cai Ren, Fei Wang, Ji-Kai Liu. **ent-Kaurane diterpenoids from the plant Wedelia trilobata**[J]. Natural Products and Bioprospecting, 2013, 3(3): 107-111.
[15]	Ming-Ming LI, Kou WANG, Juan HE, Li-Yan PENG, Xuan-Qin CHEN, Xiao CHENG, Qin-Shi ZHAO. Four new labdane-type diterpenoid glycosides from Diplopterygium laevissimum[J]. Natural Products and Bioprospecting, 2013, 3(2): 38-42.

Viewed

Full text

Abstract

Cited

Shared

Discussed