Biotransformations comparées de benzylisoquinoléines par des suspensions cellulaires végétales non productrices d'alcaloïdes

BIBLIOGRAPHIE

• AGIER C., M. BURY, F. EL-ECII, S. COUSSON-FONFRAID, F. BISTER-MIEL, J.L. GUIGNARD et C. VIEL, 1988.—Ortho-diméthoxylation d'un noyau aromatique couplée à sa déchloration: nouvelle biotransformation par des suspensions cellulaires végétales, C. R. Acad. Sci., Paris, 306. série III, 265–269.
   Google Scholar
• AMBID C., M. MOISSEEFF et S. FALLOT, 1982.—Biogenesis of monoterpenes. Bioconversion of citral by a cell suspension culture of muscat grapes. Plant Cell Reports, 1 (3), 91–93.
   PubMedGoogle Scholar
• ARANDA G. J.C. TABET, J.J. LEGUAY et M. CABOCHE 1984.—Identification of NAA-aspartate amide as the major metabolic synthesized by tobacco mesophyll protoplasts incubated in the presence of the auxin analogue NAA. Phytochem., 23 (6), 1221–1223.
   Web of Science ®Google Scholar
• ARENS H. H. FISCHER, S. LEYCU, A. RÖMER et B. ULBRICH., 1985.—Antiinflammatory compounds from Plagiorhegma dubium cell culture. Planta Medica, 52–56.
   Google Scholar
• AVIV D., F. DANTES E KROCHMAL et E. GALUN, 1983.—Biotransformation of monoterpenes by Mentha cell lines. Conversion of pulegone-substituents and related unsatured α-β-ketones. Planta Medica, 47 (1), 7 10.
   Google Scholar
• AXELROD J., R. SHOFER. J.K. INSCOE W.M. KING et A. SJOERDSMA, 1958.—The fate of papaverine in man and other mammals. J. Pharmacol. Exp. Ther., 124, 9–15.
   PubMed Web of Science ®Google Scholar
• BALSEVICH J., 1985.—Biotransformation of 10-hydroxygerniol and related compounds by a cell suspension culture of Catharanthus roseus: the formation of reduced products. Planta Medica, 47 (1), 7–10.
   Google Scholar
• BALSEVICH J. et W.G.W. KURZ, 1983.—The role of 9- and/or 10-oxygenated derivates of geraniol, geranial, nerol and neral in the biosynthesis of loganin and ajmalicine. Planta Medica, 49 (2), 79–84.
   PubMed Web of Science ®Google Scholar
• BAUMERT A., M. HIEKE et D. GRÖGER, 1983.—N-methylation of anthranilic acid to N-methyl-anthranilic acid by cell-free extracta of Ruta graveolens tissue cultures. Planta Medica, 48, 258–262.
   PubMed Web of Science ®Google Scholar
• BELPAIRE F.M. et M.G. BOGAERT, 1975.—Metabolism of papaverine. II- Species differences. Xenobiotica, 5, 421–429.
   PubMed Web of Science ®Google Scholar
• BELPAIRE F.M., M.G. BOGAERT, J.F. ROSSEEL et M. ANTEUNIS, 1975.—Metabolism of papaverine. I—Identification of metabolites in Rat bile. Xenobiotica. 5, 413–420.
   Google Scholar
• BISTER-MIEL F., 1987.—Biotransformation de la papavérine, de l'isopapavérine et d'analogues par des suspensions cellulaires végétales non productrices d'alcaloïdes. Thèse Doct. Etat Pharmacie, Paris Sud, 1–153.
   Google Scholar
• BISTER-MIEL F., C. AGIER, M. BURY, E. POSTAIRE J.L. GUIGNARD et C. VIEL, 1986a.—Biotransformation de la papavérine en papavéraldine par les cellules de Silene alba. Incidences des techniques d'extraction. Plantes méd. Phytothér., 20. 3–7.
   Google Scholar
• BISTER-MIEL F., H. CHRISTINAKI, A. HAMMOUMI, C. AGIER, M. BURY, J.L. GUIGNARD et C. VIEL, 1986b.—Biotransformation of papaverine and an analogue, isopapaverine by non-alkaloid producing cell suspension. In: Abstr. 6th Int. Congr. Plant and Cell Culture. Somers D.A., Gengenbach B.G., Biesboer D.D., Hackett W.P., Green C.E., Eds. Minneapolis, 202.
   Google Scholar
• BOUVIER P., D. BRANCENI M. PROUTEAU, E. PRUDHOMMEAUX et C. VIEL, 1976.—Synthèse, étude pharmacologique et conformationnelle de benzyl-4-isoquinoléines, analogues de la papavérine. Eur. J. Med. Chem., 11, 271–278.
   Google Scholar
• BRAEMER R., 1985.—Analyst's des capacités de biotransformation de cannabinoïdes par des souches cellulaires de Cannabis sativa L. (Cannabinacées) cultivées in vitro. Thèse Doct. Etat Pharmacie, Paris Sud, 1–192.
   Google Scholar
• CHRISTINAKI H., F. BISTER-MIEL, A. HAMMOUMI M. BURY, J.L. GUIGNARD et C. VIEL, 1987.—Identification of isopapaverine metabolites after biotransformation by Silene alba cell suspensions. Phytochem., 23, 2991–2994.
   Web of Science ®Google Scholar
• COLE D.J. et B.C. LOUGHMAN, 1984.—Transformation of phenoxyacetic acid herbicides by Phaseolus vulgaris L. callus cells. Plant Cell Reports, 3 (1), 5–7.
   PubMed Web of Science ®Google Scholar
• CORBIER B. et c. EHRET, 1986.—Biotransformation of monoterpenoids by cultured cells of Rosa centifolia. Xth Int. Cong, of Essential Oils, Flavors and Fragances. Washington DC, (nov. 1986), sous presse.
   Google Scholar
• DATTA K., B. DATTA, N. BASU et P.C. DATTA, 1983.—Biotransformation of cholesterol to diosgenin by cultured callus of Dioscorea. Indian Biol., 15 (1–2), 22–23.
   Google Scholar
• DORISSE P., J. GLEYE, p. LOISEAU, P. PUIG, A.M. EDY et M. HENRY, 1988.—Comparison between two plant cell suspensions towards papaverine biotransformation. J. Nat. Prod. (Lloydia) (sous presse).
   Google Scholar
• FURUYA T., Y. ORIHARA et H. MIYATAKE, 1986.—Biotransformation of I-menthol in Eucalyptus cell suspension culture, in: Abstr. 6th Int. Congr. Plant and Cell Culture. Somers D. A., Gengenbach B.C., Biesboer D.D., Hackett W.P. Green C.E., Eds, Minneapolis, 140.
   Google Scholar
• GARNER R.C., 1984—The role of epoxides in bioactivation and carcinogenesis, in: Bridges et Chasseaud, Progress in drug metabolism, Wiley, London, 1, 83–87.
   Google Scholar
• GOSH G., S. TIKADAR, N. MAZUMDAR et P.C. DATTA, 1983.—Biotransformation of cholesterol to thevetin in early callus of Thevetia peruviana. Indian Drugs, 21 (3), 88–89.
   Google Scholar
• HIRAOKA N. et D.P. CAREW, 1981.—Biotransformation of 2-(p-methoxyphenyl)ethylamine by Catharanthus roseus and Strobilanthes dyarianus cell cultures. J. Nat. Prod., 4(3), 285–288.
   Google Scholar
• HU Z., A.W. ALFERMANN et E. REINHARD, 1986.—Biotransfonnation of cardenolides by special cell strains of Digitalis lanata, in: Abstr. 6th Int. Congr. of Plant and Cell Culture, Somers D.A., Gengenbach B.G., Biesboer D.D., Hackett W.P., Green C.E., Eds, Minneapolis, 350.
   Google Scholar
• HUTIN M., J.P. FOUCHER, D. COURTOIS et V. PÉTIARD, 1983.—Mise en évidence de formes d'accumulation inhabituelles de morphine et de codéine dans une culture de tissus de Papaver somniferum. C. R. Acad. Sci., 297, III, 47–50.
   Google Scholar
• IWASA K., A. TOMII et N. TAKAO, 1984.—Biotransformation of the 13-hydroxytetrahydroprotoberberine N-methyl salts by callus cultures of Corydalis species. Heterocycles, 22 (1), 33–38.
   Web of Science ®Google Scholar
• JIANG Y. et J. LI, 1985.—Induced conversion in hydrocortisone biosynthesis. Yiyao Gongye, 16 (2), 49–52
   Google Scholar
• KOUADIO K., M. RIDEAU, C. GANSSER, J.C. CHENIEUX et C. VIEL, 1984.—Biotransformation of ellipticine into 5-formyl ellipticine by Choisya ternata strains. Plant Cell Reports, 3 (5), 203–205.
   PubMed Web of Science ®Google Scholar
• LEE Y.S., 1983.—Stereospecificity and enantioselectivity in the biotransformation of terpineols with the cultured cells of Nicotina tabacum. J. Sci. Hiroshima Univ., ser. A, Phys. Chem.,47 (1), 21–39.
   Google Scholar
• MIURA H., K. KAWASHIMA Y. KITAMURA et M. SUGH, 1986.—Studies of the tissue culture of Swertia japonica Makino. III—Glycosylation of naringenin in cultured cells. Shoyakugaku Zasshi, 40 (1) 40–43.
   Google Scholar
• MIZUKAMI H., A. HIRANO, T. TERAO et H. OHASHI, 1986.—Glucosyl conjugation of xeno- biotic phenols by cultured cells of Gardenia jasminoides, in: Aspects ind. cult. cell. d'origine animale et vegétale, Xe Coll. Microbiol. Ind. et Biotechn. S.F.M., Lyon, 273.
   Google Scholar
• MIZUKAMI H., T. TERAO, A. AMANO et H. OHASHI, 1986.—Glucosylation of salicyl alcohol by Gardenia jasminoides cell cultures. Plant Cell Physiol., 27 (4), 645–650.
   Web of Science ®Google Scholar
• MIZUKAMI H., T. TERAO, H. MIURA et H OHASHI, 1983.—Glucosylation of salicyl alcohol in cultured plant cells. Phytochem., 22, 679–681.
   Web of Science ®Google Scholar
• MORARD P., 1984.—Evaluation des capacités de bioconversion de cellules végétales cultivées in vitro vis-à-vis de la papavérine, de la β-phényléthylamine et du diméthyl-1,4 carbazole. DEA, Tours, 22 octobre.
   Google Scholar
• MORARD P., K. KOUADIO, C. VIEL, J.C. CHENIEUX et M. RIDEAU, 1985.—Bioconversion d'ellipticines et de structures apparentées par des cellules végétales in vitro, in: Aspects ind. cult. cell. d'origine animale et végétale, Xe Colloque Microbiol. Ind. et Biotechn. S.F.M., Lyon, 397–400.
   Google Scholar
• NARZ, KÖSTER, 1981.—cité par Braemer R.
   Google Scholar
• OKAMURA S., 1982.—In: Programma and abstracts of 5th Intl. Cong. Plant Tissue and Cell Cultu re, Tokyo, 160.
   Google Scholar
• PAISARNRAT S. et C. AMBID, 1985.—Bioconversion of geraniol by a cell suspension culture of Muscat grapes: development and metabiotic pathway. Top. Flavour Res', Proc. Int. Conf., Berger R.G. Nitz S., Schreier P., Eds 321–333.
   Google Scholar
• PODVIN L., 1985.—Analyse des capacités de biotransformation de deux suspensions cellulaires de Vinca minor sur la papavérine. DEA, Univ. Paris VI, 1–45.
   Google Scholar
• REINHARD E. et A.W. ALFERMANN, 1980.—Biotransformation by plant cell cultures, in: Advances in biochemical engineering, Fiechter A., Ed., Springer-Verlag, Berlin, Heidelberg, New York, 49–83.
   Google Scholar
• RIDEAU M., P. MORARD, C. GANSSER J C. CHENIEUX et C. VIEL, 1987.—Biotransformation et comportement inducteur de la papavérine sur diverses souches végétales. Structure des composés obtenus. Die Pharmazie (sous presse).
   Google Scholar
• ROSAZZA J.P., M. KAMMER, L. YOUEL, R.W. SMITH, P.W. ERHARDT, D.H. TRUONG et S.W. LESLIE, 1977.—Microbial models of mammalian metabolism O-demethylation of papaverine. Xenobiotica, 7, 133–134.
   PubMed Web of Science ®Google Scholar
• ROSSEEL M.T. et F.M. BELPAIRE, 1977.—Identification of papaverine metabolites in human urine by mass spectrometry, in: Quantitative mass spectrometry in Life sciences, De Leenheer et Roncucci. Elsevier Seien. Publish., Amsterdam, 133–135.
   Google Scholar
• SANDERMANN H. Jr., D. SCHEEL et T. VON DER TRENCK, 1984.—Use of plant cell cultures to study the metabolism environmental chemicals. Ecotoxicol. Environ. Saf., 8 (2), 167–182.
   PubMed Web of Science ®Google Scholar
• SCHEEL D. et H. SANDERMANN, 1981.—Metabolism of 2,4-dichlorophenoxyacetic acid in cell suspension of soybean (Glycine max L.) and wheat (Triticum aestivum L.). Planta, 152 (3) 248–252.
   Google Scholar
• SPIELER H., A.W. ALFERMANN et E. REINHARD, 1985.—Biotransformation of β-methyl- digitoxin by cell cultures of Digitalis lanata in airlift and stirred tank reactors. Appl. Microbiol. Biotechnol., 23 (1), 14.
   Web of Science ®Google Scholar
• STABA E.J., 1980.—Plant tissue culture as a source of biochemicals, Staba E.J., Ed., C. R. C. Press, Boca Raton USA, 76–83.
   Google Scholar
• SUGA T., T. HIRATA, T. AOKI, Y.S. LEE, H. HAMADA et M. FUTATSUGI, 1982.—In: Proc. 5th Int. Congr. Plant Tissue and Cell Culture, Fujiwara A., Ed., Tokyo, 381.
   Google Scholar
• SUGA T., T. HIRATA et M. FUTATSUGI, 1984.—The biotransformation of carvoxime and dihy- drocarvoxime with cell suspension cultures of Nicotiana tabacum. Phytochem., 23, 1327–1328
   Web of Science ®Google Scholar
• TABATA M., Y. UMETANI, K. SHIMA et S. TANAKA, 1984.—Glucosylation of esculetin by plant cell suspension cultures. Plant Cell, Tissue Organ. Cult., 3 (1), 3–9.
   Web of Science ®Google Scholar
• TAM W.H.J., W.G.W. KURZ, F. CONSTABEL et K.B. CHATSON, 1982.—Biotransformation of thebaine by cell suspension cultures of Papaver somniferum C.V. Marianne. Phytochem., 21, 253–255.
   Google Scholar
• TISSUT M. et F. SEVERIN, 1984.—Plantes, herbicides et désherbage—Bases scientifiques et techniques. Association de coordination technique agricole, Paris, 117.
   Google Scholar
• TSUCHIYA T., 1984a.—Production of codeine by immobilized Papaver cells. Jpn. Kokai Tokkyo Koho J.P., 59, 159, 790.
   Google Scholar
• TSUCHIYA T., 1984b.—Steroid modification by immobilized plant cells. Jpn. Kokai Tokkyo Koho J.P., 59, 159, 794.
   Google Scholar
• UMETANI Y., S. TANAKA et M. TABATA, 1982.—In: Proc. 5th Int. Congr. Plant Tissue and Cell Culture, Fujiwata A., Ed., Tokyo, 383–384.
   Google Scholar
• VARGAY Z., G. SIMON, H. WINTER et T. SZUTZ, 1980.—Qualitative and quantitative determination of drotaverine metabolites in Rat bile. Eur. J. Drug Metab. Pharmacokin., 5, 69–71.
   PubMedGoogle Scholar
• VERDEIL J.L., F. BISTER-MIEL, C. AGIER, M. PLAT, J.L. GUIGNARD et C. VIEL, 1985.—Différence de comportement de deux suspensions cellulaires végétales vis-à-vis de la bio-transformation de la papavérine. C.R. Acad. Sci., Paris 300, sér. III, 305–308.
   Google Scholar
• VERDEIL J.L., F. BISTER-MIEL, J.L. GUIGNARD et c. VIEL, 1986.—Papaverine biotransformation by Silene alba cell suspension. Planta Medica, 1–3.
   Google Scholar
• WEBER N., H. BENNING et H.K. MANGOLD, 1984.—Production of complex ether glycerolipids from exogenous alkyl glycerols by cell suspension cultures of rape. Appl. Microbiol. Biotechnol., 20 (4), 238–244.
   Web of Science ®Google Scholar
• WINK M., T. HARTMANN et L. WITTE, 1980.—Biotransformation of cadaverine and potential biogenetic intermediates of lupanine biosynthesis by plant cell suspension cultures. Planta Medica, 40 (1), 31–39.
   Web of Science ®Google Scholar