Comparative analysis of CYP93E proteins for improved microbial synthesis of plant triterpenoids

Phytochemistry

Volumn 108, Issue , 2014, Pages 47-56

  Moses, Tessa ^a,b,c,d   Thevelein, Johan M ^b,c   Goossens, Alain ^a   Pollier, Jacob ^a  

^a GHENT UNIVERSITY   (Belgium)

^b DEPARTMENT OF PLANT SYSTEMS BIOLOGY   (Belgium)

^c UNIVERSITY OF LEUVEN   (Belgium)

^d JOHN INNES CENTRE   (United Kingdom)

Author keywords

3 Hydroxy olean 12 en 24 oic acid; Fabaceae; Olean 12 ene 3 24 diol; Saccharomyces cerevisiae; Saponins; Synthetic biology

Indexed keywords

FABACEAE; SACCHAROMYCES CEREVISIAE;

AMYRIN; CYTOCHROME P450; OLEANOLIC ACID; SAPONIN; TRITERPENE;

ANALOGS AND DERIVATIVES; BARREL MEDIC; CHEMISTRY; ENZYMOLOGY; METABOLISM; SACCHAROMYCES CEREVISIAE;

CYTOCHROME P-450 ENZYME SYSTEM; MEDICAGO TRUNCATULA; OLEANOLIC ACID; SACCHAROMYCES CEREVISIAE; SAPONINS; TRITERPENES;

EID: 84911462444     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2014.10.002     Document Type: Article

References (31)

1. S. Alberti, A.D. Gitler, and S. Lindquist A suite of gateway cloning vectors for high-throughput genetic analysis in Saccharomyces cerevisiae Yeast 24 2007 913 919
2. J.M. Augustin, V. Kuzina, S.B. Andersen, and S. Bak Molecular activities, biosynthesis and evolution of triterpenoid saponins Phytochemistry 72 2011 435 457
3. S. Bak, F. Beisson, G. Bishop, B. Hamberger, R. Höfer, S. Paquette, and D. Werck-Reichhart Cytochromes P450 Arabidopsis Book 9 2011 2011 e0144 10.1199/tab.0144
4. M. Carelli, E. Biazzi, F. Panara, A. Tava, L. Scaramelli, A. Porceddu, N. Graham, M. Odoardi, E. Piano, S. Arcioni, S. May, C. Scotti, and O. Calderini Medicago truncatula CYP716A12 is a multifunctional oxidase involved in the biosynthesis of hemolytic saponins Plant Cell 23 2011 3070 3081
5. Z. Dai, B. Wang, Y. Liu, M. Shi, D. Wang, X. Zhang, T. Liu, L. Huang, and X. Zhang Producing aglycons of ginsenosides in bakers' yeast Sci. Rep. 4 2014 3698
6. B. Dinda, S. Debnath, B.C. Mohanta, and Y. Harigaya Naturally occurring triterpenoid saponins Chem. Biodivers. 7 2010 2327 2580
7. E.O. Fukushima, H. Seki, K. Ohyama, E. Ono, N. Umemoto, M. Mizutani, K. Saito, and T. Muranaka CYP716A subfamily members are multifunctional oxidases in triterpenoid biosynthesis Plant Cell Physiol. 52 2011 2050 2061
8. E.O. Fukushima, H. Seki, S. Sawai, M. Suzuki, K. Ohyama, K. Saito, and T. Muranaka Combinatorial biosynthesis of legume natural and rare triterpenoids in engineered yeast Plant Cell Physiol. 54 2013 740 749
9. A. Gholami, N. De Geyter, J. Pollier, S. Goormachtig, and A. Goossens Natural product biosynthesis in Medicago species Nat. Prod. Rep. 31 2014 356 380
10. K. Haralampidis, M. Trojanowska, and A.E. Osbourn Biosynthesis of triterpenoid saponins in plants Adv. Biochem. Eng./Biotechnol. 75 2002 31 49
11. J. Kinjo, M. Hatakeyama, M. Udayama, Y. Tsutanaga, M. Yamashita, T. Nohara, Y. Yoshiki, and K. Okubo HPLC profile analysis of oleanene-glucuronides in several edible beans Biosci. Biotechnol. Biochem. 62 1998 429 433
12. K.T. Moe, J.W. Chung, Y.I. Cho, J.K. Moon, J.H. Ku, J.K. Jung, J. Lee, and Y.J. Park Sequence information on simple sequence repeats and single nucleotide polymorphisms through transcriptome analysis of mungbean J. Integr. Plant Biol. 53 2011 63 73
13. M. Morita, M. Shibuya, T. Kushiro, K. Masuda, and Y. Ebizuka Molecular cloning and functional expression of triterpene synthases from pea (Pisum sativum) new alpha-amyrin-producing enzyme is a multifunctional triterpene synthase Eur. J. Biochem. 267 2000 3453 3460
14. T. Moses, J. Pollier, J.M. Thevelein, and A. Goossens Bioengineering of plant (tri)terpenoids: from metabolic engineering of plants to synthetic biology in vivo and in vitro New Phytol. 200 2013 27 43
15. T. Moses, J. Pollier, L. Almagro, D. Buyst, M. Van Montagu, M.A. Pedreño, J.C. Martins, J.M. Thevelein, and A. Goossens Combinatorial biosynthesis of sapogenins and saponins in Saccharomyces cerevisiae using a C-16α hydroxylase from Bupleurum falcatum Proc. Natl. Acad. Sci. U.S.A. 111 2014 1634 1639
16. D. Nelson, and D. Werck-Reichhart A P450-centric view of plant evolution Plant J. 66 2011 194 211
17. D.R. Nelson, R. Ming, M. Alam, and M.A. Schuler Comparison of cytochrome P450 genes from six plant genomes Trop. Plant Biol. 1 2008 216 235
18. A. Osbourn, R.J. Goss, and R.A. Field The saponins: polar isoprenoids with important and diverse biological activities Nat. Prod. Rep. 28 2011 1261 1268
19. Pedersen, A.G., Nielsen, H., 1997. Neural network prediction of translation initiation sites in eukaryotes: perspectives for EST and genome analysis. In: Proceedings/International Conference on Intelligent Systems for Molecular Biology; ISMB. International Conference on Intelligent Systems for Molecular Biology, vol. 5, pp. 226-233.
20. D.R. Phillips, J.M. Rasbery, B. Bartel, and S.P. Matsuda Biosynthetic diversity in plant triterpene cyclization Curr. Opin. Plant Biol. 9 2006 305 314
21. R.G. Ruiz, K.R. Price, A.E. Arthur, M.E. Rose, M.J.C. Rhodes, and R.G. Fenwick Effect of soaking and cooking on the saponin content and composition of chickpeas (Cicer arietinum) and lentils (Lens culinaris) J. Agric. Food Chem. 44 1996 1526 1530
22. H. Seki, K. Ohyama, S. Sawai, M. Mizutani, T. Ohnishi, H. Sudo, T. Akashi, T. Aoki, K. Saito, and T. Muranaka Licorice beta-amyrin 11-oxidase, a cytochrome P450 with a key role in the biosynthesis of the triterpene sweetener glycyrrhizin Proc. Natl. Acad. Sci. U.S.A. 105 2008 14204 14209
23. M. Shibuya, M. Hoshino, Y. Katsube, H. Hayashi, T. Kushiro, and Y. Ebizuka Identification of beta-amyrin and sophoradiol 24-hydroxylase by expressed sequence tag mining and functional expression assay FEBS J. 273 2006 948 959
24. S.G. Sparg, M.E. Light, and J. van Staden Biological activities and distribution of plant saponins J. Ethnopharmacol. 94 2004 219 243
25. K. Tamura, D. Peterson, N. Peterson, G. Stecher, M. Nei, and S. Kumar MEGA5: molecular evolutionary genetics analysis using maximum likelihood, evolutionary distance, and maximum parsimony methods Mol. Biol. Evol. 28 2011 2731 2739
26. A. Tava, C. Scotti, and P. Avato Biosynthesis of saponins in the genus Medicago Phytochem. Rev. 10 2010 459 469
27. R.K. Varshney, C. Song, R.K. Saxena, S. Azam, S. Yu, A.G. Sharpe, S. Cannon, J. Baek, B.D. Rosen, B. Tar'an, T. Millan, X. Zhang, L.D. Ramsay, A. Iwata, Y. Wang, W. Nelson, A.D. Farmer, P.M. Gaur, C. Soderlund, R.V. Penmetsa, C. Xu, A.K. Bharti, W. He, P. Winter, S. Zhao, J.K. Hane, N. Carrasquilla-Garcia, J.A. Condie, H.D. Upadhyaya, M.C. Luo, M. Thudi, C.L. Gowda, N.P. Singh, J. Lichtenzveig, K.K. Gali, J. Rubio, N. Nadarajan, J. Dolezel, K.C. Bansal, X. Xu, D. Edwards, G. Zhang, G. Kahl, J. Gil, K.B. Singh, S.K. Datta, S.A. Jackson, J. Wang, and D.R. Cook Draft genome sequence of chickpea (Cicer arietinum) provides a resource for trait improvement Nat. Biotechnol. 31 2013 240 246
28. J.P. Vincken, L. Heng, A. de Groot, and H. Gruppen Saponins, classification and occurrence in the plant kingdom Phytochemistry 68 2007 275 297
29. D. Werck-Reichhart, and R. Feyereisen Cytochromes P450: a success story Genome Biol. 1 2000 Reviews3003
30. B.S. Winkel Metabolic channeling in plants Annu. Rev. Plant Biol. 55 2004 85 107
31. Z. Xue, L. Duan, D. Liu, J. Guo, S. Ge, J. Dicks, P. ÓMáille, A. Osbourn, and X. Qi Divergent evolution of oxidosqualene cyclases in plants New Phytol. 193 2012 1022 1038