Inhibitor and substrate activities of sesquiterpene olefins toward (+)-δ-cadinene-8-hydroxylase, a cytochrome P450 monooxygenase (CYP706B1)

Phytochemistry

Volumn 71, Issue 16, 2010, Pages 1825-1831

  Wang, Yan Hong ^a,b   Essenberg, Margaret ^a  

^a OKLAHOMA STATE UNIVERSITY   (United States)

^b UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

Copaene; Cubebene; Humulene; Muurolene; Cadinene; Clotrimazole; Cotton; Cytochrome P450 monooxygenase; Enzyme inhibition; Gossypium arboreum; Malvaceae; Miconazole; Sesquiterpene; Substrate specificity

Indexed keywords

ALKENE; CYTOCHROME P450; DELTA CADINENE 8 HYDROXYLASE, GOSSYPIUM ARBOREUM; DELTA-CADINENE-8-HYDROXYLASE, GOSSYPIUM ARBOREUM; SESQUITERPENE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COTTON; DRUG ANTAGONISM; ENZYMOLOGY; ISOLATION AND PURIFICATION; METABOLISM; STEREOISOMERISM;

ALKENES; CATALYSIS; CYTOCHROME P-450 ENZYME SYSTEM; GOSSYPIUM; MOLECULAR STRUCTURE; SESQUITERPENES; STEREOISOMERISM;

GOSSYPIUM ARBOREUM; GOSSYPIUM HIRSUTUM; MAGNOLIOPHYTA; MALVACEAE;

EID: 77957832220     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2010.07.014     Document Type: Article

References (33)

1. I. Alchanati, J.A.A. Patel, J. Liu, C.R. Benedict, R.D. Stipanovic, A.A. Bell, Y. Cui, and C.W. Magill The enzymatic cyclization of nerolidyl diphosphate by δ-cadinene synthase from cotton stele tissue infected with Verticillium dahliae Phytochemistry 47 1998 961 967 (Pubitemid 28173282)
2. A.A. Bell, R.D. Stipanovic, D.H. O'Brien, and P.A. Fryxell Sesquiterpenoid aldehyde quinones and derivatives in pigment glands of Gossypium Phytochemistry 17 1978 1297 1305
3. G.P. Bolwell, K. Bozak, and A. Zimmerlin Plant cytochrome P450 Phytochemistry 37 1994 1491 1506
4. X.-Y. Chen, Y. Chen, P. Heinstein, and V.J. Davisson Cloning, expression, and characterization of (+)-δ-cadinene synthase: a catalyst for cotton phytoalexin biosynthesis Arch. Biochem. Biophys. 324 1995 255 266 (Pubitemid 26006408)
5. X.-Y. Chen, M. Wang, V.J. Davisson, and P. Heinstein Cloning and heterologous expression of a second cotton (+)-δ-cadinene synthase J. Nat. Prod. 59 1996 944 951 (Pubitemid 26365486)
6. A. Cortés, M. Cascante, M.L. Cardenas, and A. Cornish-Bowden Relationships between inhibition constants, inhibitor concentrations for 50% inhibition and types of inhibition: new ways of analysing data Biochem. J. 357 2001 263 268 (Pubitemid 32642925)
7. E.M. Davis, J. Tsuji, G.D. Davis, M.L. Pierce, and M. Essenberg Purification of (+)-δ-cadinene synthase, a sesquiterpene cyclase from bacteria-inoculated cotton foliar tissue Phytochemistry 41 1996 1047 1055 (Pubitemid 2619334)
8. G.D. Davis, and M. Essenberg (+)-δ-Cadinene is a product of sesquiterpene cyclase activity in cotton Phytochemistry 39 1995 553 567
9. W.L. Dean, and R.D. Gray Relationship between state of aggregation and catalytic activity for cytochrome P-450 LM2 and NADPH-cytochrome P-450 reductase J. Biol. Chem. 257 1982 14679 14685
10. G.W. Elzen, H.J. Williams, A.A. Bell, R.D. Stipanovic, and S.B. Vinson Quantification of volatile terpenes of glanded and glandless Gossypium hirsutum L. cultivars and lines by gas chromatography J. Agri. Food Chem. 33 1985 1079 1082
11. B.T. Greenhagen, P. Griggs, S. Takahashi, L. Ralston, and J. Chappell Probing sesquiterpene hydroxylase activities in a coupled assay with terpene synthases Arch. Biochem. Biophys. 409 2003 385 394 (Pubitemid 36259607)
12. D.L. Hallahan, G.W. Dawson, J.M. West, and R.M. Wallsgrove Cytochrome P-450 catalyzed monoterpene hydroxylation in Nepeta mussinii Plant Physiol. Biochem. (Paris) 30 1992 435 443
13. S. Jennewein, C.D. Rithnert, R.M. Williams, and R.B. Croteau Taxol biosynthesis: taxane 13α-hydroxylase is a cytochrome P450-dependent monooxygenase Proc. Natl. Acad. Sci. USA 98 2001 13595 13600 (Pubitemid 33115943)
14. F. Karp, J.L. Harris, and R. Croteau Metabolism of monoterpenes: demonstration of the hydroxylation of (+)-sabinene to (+)-cis-sabinol by an enzyme preparation from sage (Salvia officinalis) leaves Arch. Biochem. Biophys. 256 1987 179 193
15. F. Karp, C.A. Mihaliak, J.L. Harris, and R. Croteau Monoterpene biosynthesis: specificity of the hydroxylations of (-)-limonene by enzyme preparations from peppermint (Mentha piperita), spearmint (Mentha spicata), and perilla (Perilla frutescens) leaves Arch. Biochem. Biophys. 276 1990 219 226 (Pubitemid 20041836)
16. W.-Q. Liang, X.-P. Tan, X.-Y. Chen, T. Hashimoto, Y. Yamada, and P. Heinstein Isolation of a (+)-δ-cadinene synthase gene CAD1-A and analysis of its expression pattern in seedlings of Gossypium arboreum L. Sci. China Ser. C Life Sci. 43 2000 145 152
17. C.-J. Liu, P. Heinstein, and X.-Y. Chen Expression pattern of genes encoding farnesyl diphosphate synthase and sesquiterpene cyclase in cotton suspension-cultured cells treated with fungal elicitors Mol. Plant-Microbe Interact. 12 1999 1095 1104
18. P. Luo, Y.-H. Wang, G.-D. Wang, M. Essenberg, and X.-Y. Chen Molecular cloning and functional identification of (+)-δ-cadinene-8-hydroxylase, a cytochrome P450 mono-oxygenase (CYP706B1) of cotton sesquiterpene biosynthesis Plant J. 28 2001 95 104 (Pubitemid 33011512)
19. M.E. Mace, A.A. Bell, and C.H. Beckman Histochemistry and identification of disease-induced terpenoid aldehydes in verticillium wilt-resistant and susceptible cottons Can. J. Bot. 54 1976 2095 2099
20. K.M. Madyastha, T.D. Meehan, and C.J. Coscia Characterization of a cytochrome P-450 dependent monoterpene hydroxylase from the higher plant Vinca rosea Biochemistry 15 1976 1097 1102
21. Y.-L. Meng, J.-W. Jia, C.-J. Liu, W.-Q. Liang, P. Heinstein, and X.-Y. Chen Coordinated accumulation of (+)-δ-cadinene synthase mRNAs and gossypol in developing seeds of Gossypium hirsutum and a new member of the cad1 family from G. arboreum J. Nat. Prod. 62 1999 248 252 (Pubitemid 29137899)
22. D.R. Nelson Plant cytochrome P450s from moss to poplar Phytochem. Rev. 5 2006 193 204 (Pubitemid 44900345)
23. P.R. Ortiz De Montellano, and M.A. Correia Inhibition of cytochrome P450 enzymes P.R. Ortiz De Montellano, Cytochrome P450 Structure, Mechanism, and Biochemistry second ed. 1995 Plenum Press New York 305 364
24. D. Pompon, B. Louerat, A. Bronine, and P. Urban Yeast expression of animal and plant P450s in optimized redox environments Meth. Enzymol. 272 1996 51 64 (Pubitemid 26299867)
25. L. Ralston, S.T. Kwon, M. Schoenbeck, J. Ralston, D.J. Schenk, R.M. Coates, and J. Chappell Cloning, heterologous expression, and functional characterization of 5-epi-aristolochene-1,3-dihydroxylase from tobacco (Nicotiana tabacum) Arch. Biochem. Biophys. 393 2001 222 235 (Pubitemid 32907179)
26. M. Schalk, Y. Batard, A. Seyer, S. Nedelkina, F. Durst, and D. Werck-Reichhart Design of fluorescent substrates and potent inhibitors of CYP73As, P450s that catalyze 4-hydroxylation of cinnamic acid in higher plants Biochemistry 36 1997 15253 15261 (Pubitemid 27527990)
27. M.A. Schuler Plant cytochrome P450 monoxygenases Crit. Rev. Plant Sci. 15 1996 235 284
28. S. Takahashi, Y. Zhao, P.E. O'Maille, B.T. Greenhagen, J.P. Noel, R.M. Coates, and J. Chappell Kinetic and molecular analysis of 5-epiaristolochene 1,3-dihydroxylase, a cytochrome P450 enzyme catalyzing successive hydroxylations of sesquiterpenes J. Biol. Chem. 280 2005 3686 3696 (Pubitemid 40223836)
29. X.-P. Tan, W.-Q. Liang, C.-J. Liu, P. Luo, P. Heinstein, and X.-Y. Chen Expression pattern of (+)-δ-cadinene synthase genes and biosynthesis of sesquiterpene aldehydes in plants of Gossypium arboreum L. Planta 210 2000 644 651 (Pubitemid 30192178)
30. Y.-H. Wang, G. Davila-Huerta, and M. Essenberg 8-Hydroxy-(+)-δ- cadinene is a precursor to hemigossypol in Gossypium hirsutum Phytochemistry 63 2003 219 225 (Pubitemid 37101807)
31. A.L. Wheeler, R.M. Long, R.E.B. Ketchum, C.D. Rithner, R.M. Williams, and R. Croteau Taxol biosynthesis: differential transformations of taxadien-5α-ol and its acetate ester by cytochrome P450 hydroxylases from Taxus suspension cells Arch. Biochem. Biophys. 390 2001 265 278 (Pubitemid 32568488)
32. M. Wüst, and R. Croteau Hydroxylation of specifically deuterated limonene enantiomers by cytochrome P450 limonene-6-hydroxylase reveals the mechanism of multiple product formation Biochemistry 41 2002 1820 1827 (Pubitemid 34132256)
33. M. Wüst, D.B. Little, M. Schalk, and R. Croteau Hydroxylation of limonene enantiomers and analogs by recombinant (-)-limonene 3- and 6-hydroxylases from mint (Mentha) species: evidence for catalysis within sterically constrained active sites Arch. Biochem. Biophys. 387 2001 125 136 (Pubitemid 32989032)