Tropane alkaloid profiling of hydroponic Datura innoxia Mill. plants inoculated with Agrobacterium rhizogenes

Phytochemical Analysis

Volumn 21, Issue 1, 2010, Pages 118-127

  Jousse, Cyril ^a   Vu, Thi Dao ^a,b   Minh Tran, Thi Le ^b   Al Balkhi, Mohamad Houssam ^a   Molinié, Roland ^a   Boitel Conti, Michèle ^a   Pilard, Serge ^a   Mathiron, David ^a   Hehn, Alain ^b   Bourgaud, Frédéric ^b,c   Gontier, Eric ^a,c  

^a UNIVERSITÉ DE PICARDIE JULES VERNE   (France)

^b UNIVERSITÉ DE LORRAINE   (France)

^c Plant Advanced Technologies SA   (France)

Author keywords

Agrobacterium; Alkaloids; Datura; HRMS; Hydroponics; Hyoscyamine; Metabolomics; Plant microbes interaction; Scopolamine; Tropane

Indexed keywords

ALKALOIDS; ANTENNAS; BACTERIA; DISCRIMINANT ANALYSIS; METABOLITES; NUTRIENTS; PLANTS (BOTANY);

AGROBACTERIA; DATURA; DATURA INNOXIA; HRMS; HYOSCYAMINE; METABOLOMICS; PLANT-MICROBE INTERACTIONS; SCOPOLAMINE; TROPANE; TROPANE ALKALOIDS;

HYDROPONICS;

3 (2 HYDROXYTROPOYLOXY)TROPANE; 3 ACETOXY 6 HYDROXYTROPANE; 3 ACETOXYTROPANE; 3 TIGLOYLOXY 6 HYDROXYTROPANE; 3 TIGLOYLOXY 6,7 DIHYDROXYTROPANE; 3' HYDROXYLITTORINE; 3(HYDROXYACETOXY)TROPANE; 3,6 DITIGLOYLOXY 7 HYDROXYTROPANE; 3,6 SUBSTITUTED OXYTROPANE; 3,7 DIHYDROXY 6 TIGLOYLOXYTROPANE; ANISODAMINE; HYDROXYNORHYOSCYAMINE; HYDROXYNORLITTORINE; HYOSCYAMINE; LITTORINE; NORHYOSCYAMINE; NORLITTORINE; SCOPOLAMINE; TIGLOIDINE; TROPANE ALKALOID; TROPANONE; TROPINE; UNCLASSIFIED DRUG;

ARTICLE; COCULTURE; CONTROLLED STUDY; DATURA; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROPONICS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; PHYTOCHEMISTRY; PLANT LEAF; PLANT ROOT; RHIZOBIUM RHIZOGENES; SPECIES CULTIVATION;

AGROBACTERIUM; AGROBACTERIUM RHIZOGENES; DATURA; DATURA INNOXIA;

EID: 73349088123     PISSN: 09580344     EISSN: 10991565     Source Type: Journal    
DOI: 10.1002/pca.1180     Document Type: Article

References (31)

1. Aggarwal VK, Astle CJ, Rogers-Evans M. 2004. A concise asymmetric route to the bridged bicyclic tropane alkaloid ferruginine using enyne ring-closing metathesis. Org Lett 6: 1469-1471.
2. Berkov S, Zayed R. 2003. Comparison of tropane alkaloid spectra between Datura innoxia grown in Egypt and Bulgaria. Z Naturforsch C 59c: 184-186.
3. Berkov S, Doncheva T, Philipov S, Alexandrov K. 2005. Ontogenetic variation of the tropane alkaloids in Datura stramonium. Biochem Syst Ecol 33: 1017-1029.
4. Berkov S, Zayed R, Doncheva T. 2006. Alkaloid patterns in some varieties of Datura stramonium. Fitoterapia 77: 179-182.
5. Bieri S, Varesio E, Veuthey J-L, Muñoz O, Tseng L-H, Braumann U, Spraul M, Christen P. 2006. Identification of isomeric tropane alkaloids from Schizanthus grahamii by HPLC-NMR with loop storage and HPLC-UV-MS/SPE-NMR using a cryogenic flow probe. Phytochem Anal 17: 78-86.
6. Boitel-Conti M, Gontier E, Laberche JC, Ducrocq C, Sangwan-Norreel BS. 1995. Permeabilization of Datura innoxia hairy roots for release of stored tropane alkaloids. Planta Med 61: 287-290.
7. Borisjuk NV, Borisjuk LG, Logendra S, Petersen F, Gleba Y, Raskin I. 1999. Production of recombinant proteins in plant root exudates. Nat Biotechnol 17: 466-469.
8. Boswell HD, Dräger B, McLauchlan WR, Portsteffen A, Robins DJ, Robins RJ, Walton NJ. 1999. Specificities of the enzymes of N-alkyltropane biosynthesis in Brugmansia and Datura. Phytochemistry 52: 871-878.
9. Bulgarov VP. 2008. Functions of rol genes in plant secondary metabolism. Biotech Adv 26: 318-324.
10. Dechaux C, Boitel-Conti M. 2005. A strategy for an overaccumulation of scopolamine in Datura innoxia hairy roots cultures. Acta Biologica Cracoviensia Series Botanica 47: 101-107.
11. Dräger B. 2002. Analysis of tropane and related alkaloids. J Chromatogr A 978: 1-35.
12. Gontier E, Clément A, Bourgaud A, Guckert A. 2001. Method for producing metabolites from plants cultivated in soil-less medium. PCT patent WO 01/33942 A1.
13. Gontier E, Clément A, Tran TLM, Gravot A, Lièvre K, Guckert A, Bourgaud F. 2002. Hydroponic combined with natural or forced root permeabilization: a promising technique for plant secondary metabolite production. Plant Sci 163: 723-732.
14. Gontier E, Piutti S, Gravot A, Milesi S, Grabner A, Massot B, Lièvre K, Tran TLM, Goergen JL, Bourgaud F. 2004. Development and validation of an efficient low cost bioreactor for furanocoumarin production with Ruta graveolens shoot cultures. In Liquid Culture Systems for in Vitro Plant Propagation, Hvoslef-Eide AK, Preil W (eds). Springer: Berlin; 509-524.
15. Grynkiewicz G, Gadzikowska M. 2008.Tropane alkaloids as medicinally useful natural products and their synthetic derivatives as new drugs. Pharm Rep 60: 439-463.
16. Hashimoto T, Yamada Y. 1987. Purification and characterization of hyoscyamine 6β-hydroxylase from root cultures of Hyoscyamus niger L. Hydroxylase and epoxidase activities in the enzyme preparation. Eur J Biochem 164: 277-285.
17. Jordan M, Humam M, Bieri S, Christen P, Poblete E, Muñoz O. 2006. In vitro shoot and root organogenesis, plant regeneration and production of tropane alkaloids in some species of Schizanthus. Phytochemistry 67: 570-578.
18. Lanoue A, Shakourzadeh K, Ian Marison I, Laberche J-C, Christen P, Sangwan-Norreel B, Boitel-Conti M. 2004. Occurrence of circadian rhythms in hairy root cultures under controlled conditions. Biotechnol Bioeng 88: 722-729.
19. Majewski M, Lazny R. 1995. Synthesis of tropane alkaloids via enantioselective deprotonation of tropinone. J Org Chem 60: 5825-5830.
20. Murashige T, Skoog F, 1962. A revised medium for rapid growth and bioassays with tobacco tissue cultures. Physiol Plant 15: 473-497.
21. Nachum Z, Shupak A, Gordon CR. 2006. Transdermal scopolamine for prevention of motion sickness: clinical pharmacokinetics and therapeutic applications. Clin Pharmacokinet 45: 543-66.
22. O'Hagan D. 2000. Pyrrole, pyrrolidine, pyridine, piperidine and tropane alkaloids. Nat Prod Rep 17: 435-46.
23. Rabot S, Peerless ACJ, Robins RJ. 1995. Tigloyl-CoA:pseudotropine acyl transferase - an enzyme of tropane alkaloid biosynthesis. Phytochemistry 39: 315-322.
24. Raskin I. 1998. Recovery of products from plant roots. PCT patent WO 98/49267 A1.
25. Renner UD, Oertel R, Kirch W. 2005. Pharmacokinetics and pharmacodynamics in clinical use of scopolamine. Ther Drug Monit 27: 655-665.
26. Robinson T. 1981. Tropane alkaloids. In The Biochemistry of Alkaloids, 2nd edn, Robinson T (ed.). Springer: Berlin; 58-66.
27. Subba Rao NS. 1977. Soil Microorganism and Plant Growth. Mohan Primlani for Oxford and IBH: New Delhi.
28. Veena V, Taylor CG. 2007. Agrobacterium rhizogenes: recent developments and promising applications. In Vitro Cell Dev Biol Plant 43: 383-403.
29. Vitale AA, Acher A, Pomilio AB. 1995. Alkaloids of Datura ferox from Argentina. J Ethnopharmacol 49: 81-89.
30. Waller GR, Nowacki EK. 1978. Alkaloid Biology and Metabolism in Plants. Plenum Press: New York.
31. Zanolari B, Wolfender J-L, Guilet D, Marston A, Queiroz EF, Paulo MQ, Hostettmann K. 2003. On-line identification of tropane alkaloids from Erythroxylum vacciniifolium by liquid chromatography-UV detection-multiple mass spectrometry and liquid chromatography-nuclear magnetic resonance spectrometry. J Chromatogr A 1020: 75-89.