Molecular cloning and characterization of a cDNA encoding ent-cassa-12,15-diene synthase, a putative diterpenoid phytoalexin biosynthetic enzyme, from suspension-cultured rice cells treated with a chitin elicitor

Plant Journal

Volumn 37, Issue 1, 2004, Pages 1-8

  Cho, Eun Min ^a   Okada, Atsushi ^a   Kenmoku, Hiromichi ^b   Otomo, Kazuko ^b   Toyomasu, Tomonobu ^b,c   Mitsuhashi, Wataru ^b,c   Sassa, Takeshi ^b,c   Yajima, Arata ^d   Yabuta, Goro ^d   Mori, Kenji ^e   Oikawa, Hideaki ^f   Toshima, Hiroaki ^g   Shibuya, Naoto ^h   Nojiri, Hideaki ^a   Omori, Toshio ^a   Nishiyama, Makoto ^a   Yamane, Hisakazu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b IWATE UNIVERSITY   (Japan)

^c YAMAGATA UNIVERSITY   (Japan)

^d TOKYO UNIVERSITY OF AGRICULTURE   (Japan)

^e Fuji Flavor Co Ltd   (Japan)

^f HOKKAIDO UNIVERSITY   (Japan)

^g IBARAKI UNIVERSITY   (Japan)

^h MEIJI UNIVERSITY   (Japan)

Author keywords

( ) phytocassane; Chitin elicitor; Diterpene cyclase; Phytoalexin; Rice; Suspension cultured cell

Indexed keywords

BIOSYNTHESIS; CELLS; CLONING; CROPS; DNA; RNA; SUSPENSIONS (FLUIDS);

PRECURSORS;

PLANTS (BOTANY);

CHITIN; COMPLEMENTARY DNA; DITERPENE; DRUG DERIVATIVE; DTC1 PROTEIN, ORYZA SATIVA; ISOMERASE; MESSENGER RNA; OLIGOSACCHARIDE; PHYTOALEXINS; PLANT EXTRACT; TERPENE; VEGETABLE PROTEIN;

AMINO ACID SEQUENCE; ARTICLE; BIOSYNTHESIS; CELL CULTURE; CHEMISTRY; DNA SEQUENCE; ENZYMOLOGY; ESCHERICHIA COLI; GENE EXPRESSION REGULATION; GENETICS; METABOLISM; MOLECULAR CLONING; MOLECULAR GENETICS; NUCLEOTIDE SEQUENCE; PLANT LEAF; RADIATION EXPOSURE; RICE; SEQUENCE HOMOLOGY; ULTRAVIOLET RADIATION;

AMINO ACID SEQUENCE; CELLS, CULTURED; CHITIN; CLONING, MOLECULAR; DITERPENES; DNA, COMPLEMENTARY; ESCHERICHIA COLI; GENE EXPRESSION REGULATION, ENZYMOLOGIC; GENE EXPRESSION REGULATION, PLANT; ISOMERASES; MOLECULAR SEQUENCE DATA; OLIGOSACCHARIDES; ORYZA SATIVA; PLANT EXTRACTS; PLANT LEAVES; PLANT PROTEINS; RNA, MESSENGER; SEQUENCE ANALYSIS, DNA; SEQUENCE HOMOLOGY, AMINO ACID; TERPENES; ULTRAVIOLET RAYS;

EMBRYOPHYTA; ESCHERICHIA COLI; ORYZA SATIVA;

EID: 9144226974     PISSN: 09607412     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1365-313X.2003.01926.x     Document Type: Article

References (36)

1. Aach, H., Böse, G. and Graebe, J.E. (1995) ent-Kaurene biosynthesis in a cell-free system from wheat (Triticum aestivum L.) seedlings and the localisation of ent-kaurene synthetase in plastids of three species. Planta, 197, 333-342.
2. Ait-Ali, T., Swain, S.M., Rei, J.B., Sun, T.-P. and Kamiya, Y. (1997) The LS locus of pea encodes the gibberellin biosynthesis enzyme ent-kaurene synthase A. Plant J. 11, 443-454.
3. Akatsuka, T., Takahashi, N., Kodama, O., Sekido, H., Kono, Y. and Takeuchi, S. (1985) Novel phytoalexins (Oryzalexins A, B and C) isolated from rice blast leaves infected with Pricularia oryzae. Part 1. Isolation, characterization and biological activities of oryzalexins. Agric. Biol. Chem. 49, 1689-1694.
4. Ausubel, P.M., Brendt, R., Kingston, R.E., Moore, D.D., Seidman, J.G., Smith, J.A. and Struhl, K. (1999) Current Protocols in Molecular Biology, unit 4.3. New York: Green Publishing Associates/Wiley-Interscience.
5. Bensen, R.J., Johal, G.S., Crane, V.C., Tossberg, J.T., Schnable, P.S., Meeley, R.B. and Briggs, S.P. (1995) Cloning and characterization of the maize An1 gene. Plant Cell, 7, 75-84.
6. Cartwright, D.W., Langcake, P.W., Pryce, R.J., Leworthy, D.P. and Ride, J.P. (1981) Isolation and characterization of two phytoalexins from rice as momilactones A and B. Phytochemistry, 20, 535-537.
7. Hedden, P. and Kamiya, Y. (1997) Gibberellin biosynthesis: enzymes, genes and their regulation. Annu. Rev. Plant Physiol. Plant Mol. Biol. 48, 431-460.
8. Kato, T., Kabuto, C., Sasaki, N., Tsunagawa, M., Aizawa, H., Fujita, K., Kato, Y., Kitahara, Y. and Takahashi, N. (1973) Momilactones, growth inhibitors from rice, Oryza sativa L. Tetrahedron Lett. 3861-3864.
9. Kato, H., Kodama, O. and Akatsuka, T. (1993) Oryzalexin E, a diterpene phytoalexin from UV-irradiated rice leaves. Phytochemistry, 33, 79-81.
10. Kato, H., Kodama, O. and Akatsuka, T. (1994) Oryzalexin F, a diterpene phytoalexin from UV-irradiated rice leaves. Phytochemistry, 36, 299-301.
11. Kawaide, H., Imai, R., Sassa, T. and Kamiya, Y. (1997) ent-Kaurene synthase from the fungus Phaeosphaeria sp. L487. cDNA isolation, characterization, and bacterial expression of a bifunctional diterpene cyclase in fungal gibberellin biosynthesis. J. Biol. Chem. 272, 21706-21712.
12. Kawaide, H., Sassa, T. and Kamiya, Y. (2000) Functional analysis of the two interacting cyclase domains in ent-kaurene synthase from the fungus Phaeosphaeria sp. L487 and a comparison with cyclases from higher plants. J. Biol. Chem. 275, 2276-2280.
13. Keegstra, K., Olsen, L.J. and Theg, S.M. (1989) Chloroplastic precursors and their transport across the envelope membranes. Annu. Rev. Plant Physiol. Plant Mol. Biol. 40, 471-501.
14. Koga, J., Shimura, M., Oshima, K., Ogawa, N., Yamauchi, T. and Ogawasawara, N. (1995) Phytocassanes A, B, C and D, novel diterpene phytoalexins from rice, Oryza sativa L. Tetrahedron, 51, 7907-7918.
15. Koga, J., Ogawa, N., Yamauchi, T., Kikuchi, N., Ogasawara, N. and Shimura, M. (1997) Functional moiety for the antifungal activity of phytocassane E, a diterpene phytoalexin from rice. Phytochemistry, 44, 249-253.
16. Laemmli, U.K. (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature, 227, 680-685.
17. Lesburg, C.A., Zhai, G., Cane, D.E. and Christianson, D.W. (1997) Crystal structure of pentalene synthase: mechanistic insights on terpenoid cyclization reactions in biology. Science, 277, 1820-1824.
18. Li, Y., Nakazono, M., Tsutsumi, N. and Hirai, A. (2000) Molecular and cellular characterizations of a cDNA clonE encoding a novel isozyme of aldehyde dehydrogenase from rice. Gene, 249, 67-74.
19. McGarvey, D.J. and Croteau, R. (1995) Terpenoid metabolism. Plant Cell, 7, 1015-1026.
20. Mohan, R.S., Yee, N.K.N., Coates, R.M., Ren, Y.-Y., Stamenkovic, P., Mendez, I. and West, C.A. (1996) Biosynthesis of cyclic diterpene hydrocarbons in rice cell suspensions: Conversion of 9,10-syn-labda-8 (17),13-dienyl diphosphate to 9β-pimara-7,15-diene and stemar-13-ene. Arch. Biochem. Biophys. 330, 33-47.
21. Nojiri, H., Sugimori, M., Yamane, H., Nishimura, Y., Yamada, A., Shibuya, N., Kodama, O., Murofushi, N. and Omori, T. (1996) Involvement of jasmonic acid in elicitor-induced phytoalexin production in suspension-cultured rice cells. Plant Physiol. 110, 387-392.
22. Ogawa, S., Toyomasu, T., Yamane, H., Murofushi, N., Ikeda, R., Morimoto, Y., Nishimura, Y. and Omori, T. (1996) A step in the biosynthesis of gibberellins that is controlled by the mutaion in the semi-dwarf rice cultivar Tan-ginbozu. Plant Cell Physiol. 37, 363-368.
23. Ono, E., Wong, H.L., Kawasaki, T., Hasegawa, M., Kodama, O. and Shimamoto, K. (2001) Essential role of the small GTPase Rac in disease resistance of rice. Proc. Natl. Acad. Sci. USA, 98, 759-764.
24. Railton, I.D., Fellows, B. and West, C.A. (1984) ent-Kaurene synthesis in chloroplasts from higher plants. Phytochemistry, 23, 1261-1267.
25. Richman, A.S., Gijzen, M., Starratt, A.N., Yang, Z. and Brandle, J.E. (1999) Diterpene synthesis in Stevia rebaudiana: recruitment and up-regulation of key enzymes from the gibberellin biosynthetic pathway. Plant J. 19, 411-421.
26. Sambrook, J., Fritsch, E.F. and Maniatis, T. (1989) Molecular Cloning: a Laboratory Manual, 2nd edn. Cold Spring Harbor, New York: Cold Spring Harbor Laboratory.
27. Smith, D.B. and Johnson, K.S. (1988) Single-step purification of polypeptides expressed in Escherichia coli as functions with glutathion S-transferase. Gene, 67, 31-40.
28. Tamogami, S., Mitani, M., Kodama, O. and Akatsuka, T. (1993) Oryzalexin S structure: a new stemarane-type rice plant phytoalexin and its biogenesis. Tetrahedron, 49, 2025-2032.
29. Toshima, H., Oikawa, H., Toyomasu, T. and Sassa, T. (2000) Total synthesis of both enantiomers of copalol via optical resolution of a general synthetic intermediate for drimarene sesquiterpenes and labdane diterpenes. Tetrahedron, 56, 8443-8450.
30. Toshima, H., Oikawa, H., Yada, H., Ono, H., Toyomasu, T. and Sassa, T. (2002) Total synthesis of (±)-syn-copalol. Biosci. Biotechnol. Biochem. 66, 2504-2510.
31. VanEtten, H.D., Mansfield, J.W., Bailey, J.A. and Farmer, E.E. (1994) Two classes of plant antibiotics: phytoalexins versus 'phytoanticipins'. Plant Cell, 6, 1191-1192.
32. Vogel, B.S., Wildung, M.R., Vogel, G. and Croteau, R. (1996) Abietadiene synthase from grand fir (Abies grandis). J. Biol. Chem. 271, 23262-23268.
33. Wendt, K.U., Poralla, K. and Schulz, G.E. (1997) Structure and function of a squalene cyclase. Science, 277, 1811-1815.
34. Yajima, A., Mori, K. and Yabuta, G. Total synthesis of ent-cassa-12, 15-diene, a putative precursor of rice phytoalexins, phytocassanes A-E. Tetrahedron Lett. in press.
35. Yamaguchi, S., Saito, T., Abe, H., Yamane, H., Murofushi, N. and Kamiya, Y. (1996) Molecular cloning and characterization of a cDNA encoding the gibberellin biosynthetic enzyme ent-kaurene synthase B from pumpkin (Cucurbita maxima L.). Plant J. 10, 203-213.
36. Yamaguchi, S., Sun, T.-P., Kawaide, H. and Kamiya, Y. (1998) The GA2 locus of Arabidopsis thaliana encodes ent-kaurene synthase of gibberellin biosynthesis. Plant Physiol. 116, 1271-1278.