Composition and stereochemistry of ephedrine alkaloids accumulation in Ephedra sinica Stapf

Phytochemistry

Volumn 71, Issue 8-9, 2010, Pages 895-903

  Krizevski, Raz ^a,b   Bar, Einat ^a   Shalit, Or ^c   Sitrit, Yaron ^b   Ben Shabat, Shimon ^b   Lewinsohn, Efraim ^a  

^a VOLCANI CENTER   (Israel)

^b BEN GURION UNIVERSITY OF THE NEGEV   (Israel)

^c UNIVERSITY OF HAIFA   (Israel)

Author keywords

(1R,2S) norephedrine N methyltransferase; (S) cathinone reductase; Ephedra sinica Stapf; Ephedraceae; Ephedrine alkaloids; Metabolic pathway elucidation; Stereochemistry

Indexed keywords

ALKALOID; DISACCHARIDE; DRUG DERIVATIVE; EPHEDRINE; GLUCURONIC ACID; HERBACEOUS AGENT; METHYLTRANSFERASE; O (GLUCURONIC ACID 2 SULFATE) (1 4) O (2,5) ANHYDROMANNITOL 6 SULFATE; O-(GLUCURONIC ACID 2-SULFATE)-(1--4)-O-(2,5)-ANHYDROMANNITOL 6-SULFATE; OXIDOREDUCTASE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ENZYMOLOGY; EPHEDRA SINICA; ISOLATION AND PURIFICATION; METABOLISM; STEREOISOMERISM;

ALKALOIDS; DISACCHARIDES; DRUGS, CHINESE HERBAL; EPHEDRA SINICA; EPHEDRINE; GLUCURONATES; METHYLTRANSFERASES; MOLECULAR STRUCTURE; OXIDOREDUCTASES; STEREOISOMERISM;

EPHEDRA; EPHEDRA FOLIATA; EPHEDRA SINICA; EPHEDRACEAE;

EID: 77954214209     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2010.03.019     Document Type: Article

References (41)

1. A.H. Beckett, and G.R. Jones Identification and stereochemistry of (2S, 4S, 5R) and (2R, 4S, 5R) 2,3,4-trimethyl-5-phenyloxazolidine, degradation products of ephedrine Tetrahedron 33 1977 3313 3316
2. D. Bensky, A. Gamble, and T. Kaptchuk Chinese Herbal Medicine 1986 Materia Medica Eastland, Seattle, Washington p. 562
3. M.M. Bradford A dye binding assay for protein Anal. Biochem. 72 1976 248 254
4. J. Bruneton Pharmacognosy, Phytochemistry, Medicinal Plants 1995 Intercept Ltd. Hampshire pp. 711-715
5. S. Caveney, D.A. Charlet, H. Freitag, M. Maier-Stolte, and A.N. Starratt New observations on the secondary chemistry of world Ephedra (Ephedraceae) Am. J. Bot. 88 2001 1199 1208
6. K. Choi, T. Morishige, and F. Sato Purification and characterization of coclaurine N-methyltransferase from cultured Coptis japonica cells Phytochemistry 56 2001 649 655
7. K. Choi, T. Morishige, N. Shitan, K. Yazaki, and F. Sato Molecular cloning and characterization of coclaurine N-methyltransferase from cultured cells of Coptis japonica J. Biol. Chem. 277 2002 830 835 (Pubitemid 34952124)
8. J.F. Cui, T.H. Zhou, J.S. Zhang, and Z.C. Lou Analysis of alkaloids in Chinese Ephedra species by gas chromatographic methods Phytochem. Anal. 2 1991 116 119
9. E.M. Davis, K.L. Ringer, M.E. McConkey, and R. Croteau Monoterpene metabolism. Cloning, expression, and characterization of menthone reductases from peppermint Plant Physiol. 137 2005 873 881
10. B. Drager Biotechnology of Solanaceae alkaloids: a model or an industrial perspective? O. Kayser, W. Quax, Medicinal Plants Biotechnology: From Basic Research to Industrial Applications 2007 Wiley-VCH Weinheim, Germany 239
11. M. Gross, J. Friedman, N. Dudai, O. Larkov, Y. Cohen, E. Bar, U. Ravid, E. Putievsky, and E. Lewinsohn Biosynthesis of estragole and t-anethole in bitter fennel (Foeniculum vulgare Mill. Var. vulgare) chemotypes. Changes in SAM:phenylpropene O-methyltransferase activities during development Plant Sci. 163 2002 1047 1053
12. G. Grue-Sorensen, and I.D. Spenser Biosynthetic route to the Ephedra alkaloids Am. Chem. Soc. 116 1994 6195 6200
13. J. Hou, J. Zheng, and S.A. Shamsi Simultaneous chiral separation of ephedrine alkaloids by MEKC-ESI-MS using polymeric surfactant II: application in dietary supplements Electrophoresis 28 2007 1426 1434 (Pubitemid 46729096)
14. T.F. Jiang, Z.H. Lv, and Y.H. Wang Chiral separation of ephedrine alkaloids from Ephedra sinica extract and its medicinal preparation using cyclodextrin-modified capillary zone electrophoresis J. Anal. Chem. 62 2007 85 89
15. M. Johansen, and H. Bundgaard Prodrugs as drug delivery systems XXV: hydrolysis of oxazolidines-a potential new prodrug type J. Pharm. Sci. 72 1982 1294 1298
16. Y. Kaminaga, J. Schnepp, G. Peel, C.M. Kish, G.B. Nissan, D. Weiss, I. Orlova, O. Lavie, D. Rhodes, K. Wood, D.M. Porterfield, A.J.L. Cooper, J.V. Schloss, E. Pichersky, A. Vainstein, and N. Dudareva Plant phenylacetaldehyde synthase is a bifunctional homotetrameric enzyme that catalyzes phenylalanine decarboxylation and oxidation J. Biol. Chem. 281 2006 23357 23366
17. T. Karl, A.J. Curtis, T.N. Rosenstiel, R.K. Monson, and R. Fall Transient releases of acetaldehyde from tree leaves - products of a pyruvate overflow mechanism? Plant Cell Environ. 25 2002 1121 1131
18. M. Kataoka, Y. Nakamura, N. Urano, T. Ishige, G. Shi, S. Kita, K. Sakamoto, and S. Shimizu A novel NADP+ dependent L-1-amino-2-propanol dehydrogenase from Rhodococcus erythropolis MAK154: a promising enzyme for the production of double chiral amino alcohols Lett. Appl. Microbiol. 43 2006 430 435
19. M. Kataoka, T. Ishige, N. Urano, Y. Nakamura, E. Sakuradani, S. Fukui, S. Kita, K. Sakamoto, and S. Shimizu Cloning and expression of the L-1-amino-2-propanol dehydrogenase gene from Rhodococcus erythropolis, and its application to double chiral compound production Appl. Microbiol. Biotechnol. 80 2008 597 604
20. N.S. Khruscheva, N.M. Loim, V.I. Sokolov, and V.D. Makhaev The solid-state diastereoselective formation of oxazolidines J. Chem. Soc. Perkin Trans. 46 1997 2425 2427
21. Y. Kitani, S. Zhu, T. Omote, K. Tanaka, J. Batkhuu, C. Sanchir, H. Fushimi, M. Mikage, and K. Komatsu Molecular analysis and chemical evaluation of Ephedra plants in Mongolia Biol. Pharm. Bull. 32 2009 1235 1243
22. R. Krizevski, N. Dudai, E. Bar, and E. Lewinsohn Developmental patterns of ephedrine alkaloids accumulation in khat (Catha edulis Forsk., Celastraceae) J. Ethnopharmacol. 114 2007 432 438
23. R. Krizevski, N. Dudai, E. Bar, I. Dessow, U. Ravid, and E. Lewinsohn Quantitative stereoisomeric determination of phenylpropylamino alkaloids in khat (Catha edulis Forsk.) Isr. J. Plant Sci. 56 2008 207 213
24. Leete, E., 1958. Biogenesis of d-norpseudoephedrine in Catha edulis. Chem. Ind. 1088-1089.
25. E. Lewinsohn, I. Ziv-Raz, N. Dudai, Y. Tadmor, E. Lastochkin, O. Larkov, D. Chaimovitsh, U. Ravid, E. Putievsky, E. Pichersky, and Y. Shoham Biosynthesis of estragole and methyl-eugenol in sweet basil (Ocimum basilicum L). Developmental and chemotypic association of allylphenol O-methyltransferase activities Plant Sci. 160 2000 27 35
26. W.H. Lewis, and M.P.F. Elvin-Lewis Medical Botany, Plants Affecting Man's Health 1977 Wiley Interscience USA pp. 189-190
27. S. Loeffler, B. Deus-Neumann, and M.H. Zenk S-adenosyl-l-methionine: (S)- coclaurine-N-methyltransferase from Tinospora cordifolia Phytochemistry 38 1994 1387 1395
28. 1H NMR spectroscopic studies of the stability of an oxazolidine condensation product Magn. Reson. Chem. 35 1997 337 341
29. K. Nakajima, T. Hashimoto, and Y. Yamada Two tropinone reductases with different stereospecificity are short chain dehydrogenase/reductases evolved from a common ancestor Proc. Natl. Acad. Sci. USA 90 1993 9591 9595
30. N.A. O'Dowd, P.G. McCauley, G. Wilson, J.A.N. Parnell, T.A.K. Kavanaugh, and D.J. McConnell Ephedra species: in vitro culture, micropropagation and the production of ephedrine and other alkaloids Y.P.S. Bajaj, Biotechnology in Agriculture and Forestry 41. Medicinal and Aromatic Plants X 1998 Springer-Verlag Berlin, Germany 154 193
31. T. Okada, M. Mikage, and S. Sekita Molecular characterization of the phenylalanine ammonia lyase from Ephedra sinica Biol. Pharm. Bull. 31 2008 2194 2199
32. T. Okada, Y. Nakamura, S. Kanaya, A. Takano, K.J. Malla, T. Nakane, M. Kitayama, and S. Sekita Metabolome analysis of ephedra plants with different contents of ephedrine alkaloids by using UPLC-Q-TOF-MS Planta Med. 75 2009 1356 1362
33. R.B. Rothman, N. Vu, J.S. Partilla, B.L. Roth, S.J. Hufeisen, B.A. Compton-Toth, J. Birkes, R. Young, and R.A. Glennon In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates J. Pharmacol. Exp. Ther. 307 2003 138 145
34. A.I. Saeed, V. Sharov, J. White, J. Li, W. Liang, N. Bhagabati, J. Braisted, M. Klapa, T. Currier, M. Thiagarajan, A. Sturn, M. Snuffin, A. Rezantsev, D. Popov, A. Ryltsov, E. Kostukovich, I. Borisovsky, Z. Liu, A. Vinsavich, V. Trush, and J. Quackenbush A free, opensource system for microarray data management and analysis Biotechniques 34 2003 374 378
35. G. Scalliet, F. Piola, C.J. Douady, S. Rety, O. Raymond, S. Baudino, K. Bordji, M. Bendahmane, C. Dumas, J.M. Cock, and P. Hugueney Scent evolution in Chinese roses Proc. Natl. Acad. Sci. USA 105 2008 5927 5932
36. H. Tsuji, N. Meguro, Y. Suzuki, N. Tsutsumi, A. Hirai, and M. Nakazono Induction of mitochondrial aldehyde dehydrogenase by submergence facilitates oxidation of acetaldehyde during re-aeration in rice FEBS Lett. 546 2003 369 373
37. R.B. Walker, L.D. Fitz, L.M. Willams, and Y.M. McDaniel The effect of ephedrine prodrugs on locomotor activity in rats Gen. Pharmacol. 27 1996 109 111
38. R.B. Walker, V.N. Dholakia, K.L. Brasfield, and R. Bakhtiar Effect of hydroxypropyl-β-cyclodextrin on the central stimulant activity of (-)-ephedrine and an oxazolidine prodrug in rats Gen. Pharmacol. 30 1998 725 731 (Pubitemid 28167776)
39. L.L. Wang, N. Kakiuchi, and M. Mikage Studies of Ephedra plants in Asia. Part 6: geographical changes of anatomical features and alkaloids content of Ephedra sinica J. Nat. Med. 64 2010 63 69
40. Z. Yaniv, and D. Palevitch Effect of drought on the secondary metabolites of medicinal and aromatic plants, a review C.K. Atal, B.M. Kapur, Cultivation and Utilization of Medicinal Plants 1982 Regional Research Laboratory, Council of Scientific and Industrial Research Jammu-Tawi, India 1 12
41. J. Ziegler, S. Voigtlander, J. Schmidt, R. Kramell, O. Miersch, C. Ammer, A. Gesell, and T.M. Kutchan Comparative transcript and alkaloid profiling in Papaver species identifies a short chain dehydrogenase/reductase involved in morphine biosynthesis Plant J. 48 2006 177 192