Natural Products and Bioprospecting    2016, Vol. 6 Issue (3) : 167-171     DOI: 10.1007/s13659-016-0096-4
Original article |
Identification and Characterization of a d-Cadinol Synthase Potentially Involved in the Formation of Boreovibrins in Boreostereum vibrans of Basidiomycota
Hui Zhou1,2, Yan-Long Yang1,2, Jun Zeng1,2, Ling Zhang1, Zhi-Hui Ding1, Ying Zeng1
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
Download: PDF(803 KB)   HTML ()  
Export: BibTeX | EndNote | Reference Manager | ProCite | RefWorks    
Abstract  Sesquiterpenoids are very common among natural products. A large number of sesquiterpene synthase genes have been cloned and functionally characterized. However, until now there is no report about the δ-cadinol synthase predominantly forming d-cadinol (syn. torreyol) from farnesyl diphosphate. Sesquiterpenoids boreovibrins structurally similar to δ-cadinol were previously isolated from culture broths of the basidiomycete fungus Boreostereum vibrans. This led us to expect a corresponding gene coding for a δ-cadinol synthase that may be involved in the biosynthesis of boreovibrins in B. vibrans. Here we report the cloning and heterologous expression of a new sesquiterpene synthase gene from B. vibrans. The crude and purified recombinant enzymes, when incubating with farnesyl diphosphate as substrate, gave δ-cadinol as its principal product and thereby identified as a δ-cadinol synthase.
Keywords Delta-cadinol      Sesquiterpene synthase      Biosynthesis      GC-MS      Fungi     
Fund:This work was supported by a grant from the National Natural Science Foundation of China (21572237);We are grateful to Professor Jian-Xin Pu (Kunming Institute of Botany) for his helpful suggestion
Issue Date: 08 February 2018
Service
E-mail this article
E-mail Alert
RSS
Articles by authors
Hui Zhou
Yan-Long Yang
Jun Zeng
Ling Zhang
Zhi-Hui Ding
Ying Zeng
Trendmd:   
Cite this article:   
Hui Zhou,Yan-Long Yang,Jun Zeng, et al. 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.
URL:  
http://npb.kib.ac.cn/EN/10.1007/s13659-016-0096-4     OR     http://npb.kib.ac.cn/EN/Y2016/V6/I3/167
1. J.K. Liu, Chem. Rev. 105, 2723-2744 (2005)
2. J.K. Liu, Chem. Rev. 106, 2209-2223 (2006)
3. R. Geris, T.J. Simpson, Nat. Prod. Rep. 26, 1063-1094 (2009)
4. A. Schüffler, T. Anke, Secondary metabolites of basidiomycetes, in The Mycota XV, Physiology and Genetics, vol. 15, ed. by T. Anke, D. Weber (Springer, Heidelberg, 2009), pp. 209-231
5. D.Z. Liu, F. Wang, T.G. Liao, J.G. Tang, W. Steglich, H.J. Zhu, J.K. Liu, Org. Lett. 8, 5749-5752 (2006)
6. M.Y. Jiang, F. Wang, X.L. Yang, L.Z. Fang, Z.J. Dong, H.J. Zhu, J.K. Liu, Chem. Pharm. Bull. 56, 1286-1288 (2008)
7. M.Y. Jiang, L. Zhang, Z.J. Dong, Z.L. Yang, Y. Leng, J.K. Liu, Chem. Pharm. Bull. 58, 113-116 (2010)
8. G.Q. Wang, K. Wei, T. Feng, Z.H. Li, L. Zhang, Q.A. Wang, J.K. Liu, J. Asian Nat. Prod. Res. 14, 115-120 (2012)
9. G.Q. Wang, K. Wei, Z.H. Li, T. Feng, J.H. Ding, Q.A. Wang, J.K. Liu, J. Asian Nat. Prod. Res. 15, 950-955 (2013)
10. P.J. Zhao, Y.L. Yang, L. Du, J.K. Liu, Y. Zeng, Angew. Chem. Int. Ed. 52, 2298-2302 (2013)
11. Y.L. Yang, H. Zhou, G. Du, K.N. Feng, T. Feng, X.L. Fu, J.K. Liu, Y. Zeng, Angew. Chem. Int. Ed. (2016). doi:10.1002/anie. 201510928
12. J.H. Ding, T. Feng, Z.H. Li, L. Li, J.K. Liu, Nat. Prod. Bioprospect. 2, 200-205 (2012)
13. A.M. Ainsworth, A.D.M. Rayner, S.J. Broxholme, J.R. Beeching, J.A. Pryke, P.R. Scard, J. Berriman, K.A. Powell, A.J. Floyd, S.K. Branch, Mycol. Res. 94, 799-809 (1990)
14. D.W. Christianson, Chem. Rev. 106, 3412-3442 (2006)
15. F. Jullien, S. Moja, A. Bony, S. Legrand, C. Petit, T. Benabdelkader, K. Poirot, S. Fiorucci, Y. Guitton, F. Nicolè, S. Baudino, J.-L. Magnard, Plant Mol. Biol. 84, 227-241 (2014)
16. Y. Hu, W.K.W. Chou, R. Hopson, D.E. Cane, Chem. Biol. 18, 32-37 (2011)
17. P. Rabe, J.S. Dickschat, Angew. Chem. Int. Ed. 52, 1810-1812 (2013)
18. Y. Yamada, T. Kuzuyama, M. Komatsu, K. Shin-ya, S. Omura, D.E. Cane, H. Ikeda, Proc. Natl. Acad. Sci. USA 112, 857-862 (2015)
19. S. Lee, J. Chappell, Plant Physiol. 147, 1017-1033 (2008)
20. B. Engels, U. Heinig, T. Grothe, M. Stadler, S. Jennewein, J. Biol. Chem. 286, 6871-6878 (2011)
21. S. Agger, F. Lopez-Gallego, C. Schmidt-Dannert, Mol. Microbiol. 72, 1181-1195 (2009)
22. F. Lopez-Gallego, S.A. Agger, D. Abate-Pella, M.D. Distefano, C. Schmidt-Dannert, ChemBioChem 11, 1093-1106 (2010)
23. G.T. Wawrzyn, M.B. Quin, S. Choudhary, F. López-Gallego, C. Schmidt-Dannert, Chem. Biol. 19, 772-783 (2012)
24. M.B. Quin, C.M. Flynn, G.T. Wawrzyn, S. Choudhary, C. Schmidt-Dannert, ChemBioChem 14, 2480-2491 (2013)
25. S. Garms, T.G. Kollner, W. Boland, J. Org. Chem. 75, 5590-5600 (2010)
26. B. Pickel, D.P. Drew, T. Manczak, C. Weitzel, H.T. Simonsen, D.K. Ro, Biochem. J. 448, 261-271 (2012)
[1] Valery M. Dembitsky, Tatyana A. Gloriozova, Vladimir V. Poroikov. Pharmacological and Predicted Activities of Natural Azo Compounds[J]. Natural Products and Bioprospecting, 2017, 7(1): 151-169.
[2] Caroline Alves Breda, Alessandra Marcon Gasperini, Vera Lucia Garcia, Karin Maia Monteiro, Giovana Anceski Bataglion, Marcos Nogueira Eberlin, Marta Cristina Teixeira Duarte. Phytochemical Analysis and Antifungal Activity of Extracts from Leaves and Fruit Residues of Brazilian Savanna Plants Aiming Its Use as Safe Fungicides[J]. Natural Products and Bioprospecting, 2016, 6(4): 195-204.
[3] Ce Kuang, Shu-Xi Jing, Yan Liu, Shi-Hong Luo, Sheng-Hong Li. Drimane Sesquiterpenoids and Isochromone Derivative from the Endophytic Fungus Pestalotiopsis sp. M-23[J]. Natural Products and Bioprospecting, 2016, 6(3): 155-160.
[4] 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.
[5] Han-Jing CHEN, Takayoshi AWAKAWA, Jie-Yin SUN, Toshiyuki WAKIMOTO, Ikuro ABE. Epigenetic modifier-induced biosynthesis of novel fusaric acid derivatives in endophytic fungi from Datura stramonium L.[J]. Natural Products and Bioprospecting, 2013, 3(1): 20-23.
Viewed
Full text


Abstract

Cited

  Shared   
  Discussed