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

Archives of Biochemistry and Biophysics

Volumn 330, Issue 1, 1996, Pages 33-47

  Mohan, Ram S ^a   Yee, Nathan K N ^a   Coates, Robert M ^a   Ren, Yue Ying ^b   Stamenkovic, Predrag ^b   Mendez, Irena ^b   West, Charles A ^b  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Diterpene biosynthesis; Diterpene synthases; Elicitation; Isoprenoid biosynthesis; Phytoalexins; Rice (Oryza sativa L.) cell suspensions

Indexed keywords

ORYZA SATIVA;

9BETA PIMARA 7,15 DIENE; CHITIN; DITERPENE; HYDROCARBON; LABDA 8(17),13 DIENYL DIPHOSPHATE; STEMAR 13 ENE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; CELL SUSPENSION; CYCLIZATION; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME SUBSTRATE; GENE CONVERSION; NONHUMAN; PRIORITY JOURNAL; RICE;

BIOTRANSFORMATION; CHITIN; DITERPENES; KINETICS; MOLECULAR STRUCTURE; ORYZA SATIVA; PHOSPHORIC ACID ESTERS; PLANT EXTRACTS; RADIOISOTOPE DILUTION TECHNIQUE; SUBSTRATE SPECIFICITY; TERPENES; TRANSFERASES; TRITIUM;

EID: 0029951087     PISSN: 00039861     EISSN: None     Source Type: Journal    
DOI: 10.1006/abbi.1996.0223     Document Type: Article

References (53)

1. Cartwright, D. W., Langcake, P. W., Pryce, R. J., Leworthy, D. P., and Ride, J. P. (1981) Phytochemistry 20, 535-537.
2. Kato, T., Kabuto, C., Sasaki, N., Tsunagawa, M., Aizawa, H., Fujita, K., Kato, Y., Kitahara, Y., and Takahishi, N. (1973) Tetrahedron Lett. 3861-3864.
3. Akatsuka, T., Takahashi, N., Kodama, O., Sekido, H., Kono, Y., and Takeuchi, S. (1985) Agric. Biol. Chem. 49, 1689-1694.
4. Kono, Y., Takeuchi, S., Kodama, O., and Akatsuka, T. (1984) Agric. Biol. Chem. 48, 253-255.
5. Sekido, H., Endo, T., Suga, R., Kodama, O., Akatsuka, T., Kono, Y., and Takeuchi, S. (1986) J. Pest. Sci. 11, 369-372.
6. Kato, H., Kodama, O., and Akatsuka, T. (1993) Phytochemistry 33, 79-81.
7. Kato, H., Kodama, O., and Akatsuka, T. (1994) Phytochemistry 36, 299-301.
8. Tamogami, S., Mitani, M., Kodama, O., and Akatsuka, T. (1993) Tetrahedron 49, 2025-2032.
9. Manchand, P. S., and Blount, J. F. (1975) J. Chem. Soc. Chem. Commun. 894-895.
10. Koga, J., Shimura, M., Oshima, K., Ogawa, N., Yamauchi, T., and Ogasawara, N. (1995) Tetrahedron 51, 7907-7918.
11. West, C. A. (1981) in Biosynthesis of Isoprenoid Compounds (Porter, J. W., and Spurgeon, S. L., Eds.), Vol. 1, pp. 376-411, Wiley, New York.
12. Bartlett, P. A. (1984) in Asymmetric Synthesis (Morrison, J. D., Ed.), Vol. 3, Chap. 5, Academic Press, New York.
13. Smit, V. A., Semenovskii, A. V., Brunovlenskaya, I. I., Portnova, S. L., and Kucherov, V. F. (1965) Dokl. Akad. Nauk. SSSR Ser. Khim. 160, 849.
14. Muntyan, G. E., Kurbanov, M., Smit, V. A., Semenovskii, A. V., and Kucherov, V. F. (1973) Izv. Akad Nauk SSSR Ser. Khim., 633.
15. Van Tamelen, E. E., and Coates, R. M. (1982) Biorg. Chem. 11, 171-196.
16. Hemming, F. W. (1983) in Biosynthesis of Isoprenoid Compounds (Porter, J. W., and Spurgeon, S. L., Eds.), Vol. 2, pp. 305-354, Wiley, New York.
17. Suga, T., Shishibori, T., and Nakaya, K. (1980) Phytochemistry 19, 2327-2330.
18. Benedict, C. R. (1983) in The Biosynthesis of Isoprenoid Compounds (Porter, J. W., and Spurgeon, S. L., Eds.), Vol. 2, pp. 355-369, Wiley, New York.
19. Yee, N. K. N. (1991) Ph.D. thesis, University of Illinois, Urbana, IL.
20. Wickham, K. A., and West, C. A. (1992) Arch. Biochem. Biophys. 293, 320-332.
21. Chu, M., and Coates, R. M. (1992) J. Org. Chem. 57, 4590-4597.
22. Jansen, B. J. M., Schepers, G. C., and de Groot, A. (1989) Tetrahedron 45, 2773-2776.
23. Yee, N. K. N., and Coates, R. M. (1992) J. Org. Chem. 57, 4598-4608.
24. Ren, Y.-Y., and West, C. A. (1992) Plant Physiol. 99, 1169-1178.
25. Bielmann, J.-F., and Ducep, J.-B. (1982) Org. React. 27, Chap. 1.
26. Altman, L. J., Ash, L., and Marson, S. (1974) Synthesis 129-131.
27. Still, W. C., and Gennari, C. (1983) Tetrahedron Lett. 24, 4405-4408.
28. Nagaoka, H., and Kishi, Y. (1981) Tetrahedron 37, 3873-3888.
29. Marshall, J. A., DeHoff, B. S., and Cleary, D. G. (1986) J. Org. Chem. 51, 1735-1741.
30. Tanaka, Y., Sato, H., Kageyu, A., and Tomita, T. (1985) J. Chromatogr. 347, 275-283.
31. Tanaka, Y., Sato, H., and Kageyu, A. (1982) Polymers 23, 1087-1090.
32. Coates, R. M., Ley, D. A., and Cavender, P. L. (1978) J. Org. Chem. 43, 4915-4922.
33. Cavender, P. L. (1977) Ph.D. thesis, University of Illinois, Urbana, IL.
34. Nakano, T., and Djerassi, C. (1961) J. Org. Chem. 26, 167-173.
35. Cane, D. E., Iyengar, R., and Shiao, M.-S. (1981) J. Am. Chem. Soc. 103, 914-931.
36. Corey, E. J., Kim, C. U., and Takeda, M. (1972) Tetrahedron Lett. 13, 4339-4342.
37. Grdina, M. B., Orfanopoulos, M., and Stephenson, L. M. (1979) J. Org. Chem. 44, 2936-2938.
38. Woodside, A. B., Huang, Z., and Poulter, C. D. (1988) Org. Synth. 66, 211; (1993) Coll. Vol. VIII, 616-620.
39. Woodside, A. B., Huang, Z., and Poulter, C. D. (1988) Org. Synth. 66, 211; (1993) Coll. Vol. VIII, 616-620.
40. Davisson, V. J., Woodside, A. B., and Poulter, C. D. (1985) Methods Enzymol. 110, 130-144.
41. Coates, R. M., Denissen, J. F., Juvik, J. A., and Babka, B. A. (1988) J. Org. Chem. 53, 2186-2192.
42. Garbarino, J. A., and Molinari, A. (1990) Phytochemistry 29, 3037-3039.
43. Marshall, J. A., and Partridge, J. J. (1969) Tetrahedron 25, 2159-2192.
44. Berettoni, M., Bettolo, R. M., Montanari, V., Precipe, T., and Romeo, S. (1991) Helv. Chim. Acta. 74, 1671-1678.
45. Gamborg, O. L., Miller, R. A., and Ojima, K. (1968) Exp. Cell. Res. 50, 151-158.
46. Croteau, R. B., and Satterwhite, D. M. (1990) J. Chromatogr. 500, 349-354.
47. Audier, H. E., Bory, S., Fetizon, M., and Anh, N.-T. (1966) Bull. Soc. Chim. Fr. 4002-4010.
48. Dev, S., and Misra, R. (1986) CRC Handbook of Terpenoids. Diterpenoids (Dev, S., Ed.), Vol. III, pp. 177-182, CRC Press, Boca Raton, FL.
49. Dalziel, W., Hesp, B., Stevenson, K. M., and Jarvis, J. A. J. (1973) J. Chem. Soc., Perkin Trans. 1, 2841-2851.
50. Ackland, M. J., Hanson, J. R., and Ratcliffe, A. H. (1984) J. Chem. Soc., Perkin Trans. 1, 2751-2754.
51. Duncan, J. D., and West, C. A. (1981) Plant Physiol. 68, 1128-1134.
52. Dixon, R. A., Dey, P. M., and Lamb, C. J. (1983) Adv. Enzymol. Relat. Areas Mol. Biol. 55, 1-136.
53. Van Etten, H. D., Mathews, D. W., and Mathews, P. S. (1989) Annu. Rev. Phytopathol. 27, 143-164.