Justicidin B 7-hydroxylase, a cytochrome P450 monooxygenase from cell cultures of Linum perenne Himmelszelt involved in the biosynthesis of diphyllin

Phytochemistry

Volumn 68, Issue 22-24, 2007, Pages 2736-2743

  Hemmati, Shiva ^a   Schneider, Bernd ^b   Schmidt, Thomas J ^c   Federolf, Katja ^a   Alfermann, A Wilhelm ^a   Fuss, Elisabeth ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

^b MAX PLANCK INSTITUTE FOR CHEMICAL ECOLOGY   (Germany)

^c UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Cytochrome P450; Diphyllin; Justicidin B; Justicidin B 7 hydroxylase; Lignan; Linaceae; Linum perenne

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; CYTOCHROME P450; DIPROPHYLLINE; GLYCOSIDE; JUSTICIDIN A; LIGNAN; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; CELL CULTURE; CHEMICAL STRUCTURE; CHEMISTRY; CYTOLOGY; ENZYME SPECIFICITY; ENZYMOLOGY; FLAX; ISOMERISM; METABOLISM;

CELLS, CULTURED; CYTOCHROME P-450 ENZYME SYSTEM; DIOXOLANES; FLAX; GLYCOSIDES; ISOMERISM; LIGNANS; MOLECULAR STRUCTURE; SUBSTRATE SPECIFICITY;

LINACEAE; LINUM PERENNE; MAGNOLIOPHYTA;

EID: 36549061532     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2007.10.025     Document Type: Article

References (33)

1. Bradford M.M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72 (1976) 248-254
2. Chen C.C., Hsin W.C., Ko F.N., Huang Y.L., Ou J.C., and Teng C.M. Antiplatelet arylnaphthalide lignans from Justicia procumbens. J. Nat. Prod. 59 (1996) 1149-1150
3. Clemens S., Hinderer W., Wittkampf U., and Barz W. Characterization of cytochrome P450-dependent isoflavone hydroxylase from chickpea. Phytochemistry 32 (1993) 653-657
4. Davin L.B., Bedgar D.L., Katayama T., and Lewis N.G. On the stereoselective synthesis of (+)-pinoresinol in Forsythia suspensa from its achiral precursor, coniferyl alcohol. Phytochemistry 31 (1990) 3869-3874
5. 5 is required for full activity of flavonoid 3′, 5′-hydroxylase, a cytochrome P450 involved in the formation of blue flower colors. Proc. Natl. Acad. Sci. USA 96 (1999) 778-783
6. Dinkova-Kostova A.T., Gang D.R., Davin L.B., Bedgar D.L., Chu A., and Lewis N.G. (+)-Pinoresinol/(+)-lariciresinol reductase from Forsythia intermedia. J. Biol. Chem. 271 (1996) 29473-29482
7. Donaldson R.P., and Luster D.G. Multiple forms of plant cytochrome P-450. Plant Physiol. 96 (1991) 669-674
8. Federolf K., Alfermann A.W., and Fuss E. Aryltetralin-lignan formation in two different cell lines of Linum album: deoxypodophyllotoxin 6-hydroxylase, a key-enzyme for the formation of 6-methoxypodophyllotoxin. Phytochemistry 68 (2007) 1397-1406
9. Fujita M., Gang D.R., Davin L.B., and Lewis N.G. Recombinant pinoresinol-lariciresinol reductases from Western red cedar (Thuja plicata) catalyze opposite enantiospecific conversions. J. Biol. Chem. 274 (1999) 618-627
10. Fuss E. Lignans in plant cell and organ cultures: An overview. Phytochem. Rev. 2 (2003) 307-320
11. Gerardy R., and Zenk M.H. Formation of salutaridine from (R)-reticuline by a membrane bound cytochrome P-450 enzyme from Papaver somniferum. Phytochemistry 32 (1993) 79-86
12. Hemmati S., Schmidt T.J., and Fuss E. (+)-Pinoresinol/(-)-lariciresinol reductase from Linum perenne Himmelszelt involved in the biosynthesis of justicidin B. FEBS Lett. 581 (2007) 603-610
13. Kuhlmann, S., 2004. Untersuchungen zur Rolle von Cytochrom P450-Enzymen in der Biosynthese von Aryltetralin-Lignanen in Zellkulturen von Linum spec. PhD Thesis, Philipps-University Marburg.
14. Mohagheghzadeh A., Schmidt T.J., and Alfermann A.W. Arylnaphthalene lignans from in vitro cultures of Linum austriacum. J. Nat. Prod. 65 (2002) 69-71
15. Molog G.A., Empt U., Kuhlmann S., van Uden W., Pras N., Alfermann A.W., and Petersen M. Deoxypodophyllotoxin 6-hydroxylase, a cytochrome P450 monooxygenase from cell cultures of Linum flavum involved in the biosynthesis of cytotoxic lignans. Planta 214 (2001) 288-294
16. Moss G.P. Nomenclature of lignans and neolignans. Pure Appl. Chem. 72 (2000) 1493-1523
17. Ortiz de Montellano P.R., and Correia M.A. Inhibition of cytochrome P450 enzymes. In: Oritz de Montellano P.R. (Ed). Cytochrome P450: Structure, Mechanism, and Biochemistry. second ed. (1995), Plenum, New York 305-364
18. Petersen M. Cytochrome P450-dependent hydroxylation in the biosynthesis of rosmarinic acid in Coleus. Phytochemistry 45 (1997) 1165-1172
19. Petersen M. Cinnamic acid 4-hydroxylase from cell cultures of the hornwort Anthoceros agrestis. Planta 217 (2003) 96-101
20. Prieto J.M., Giner R.M., Recio M.C., Schinella G., Máñez S., and Rios J.L. Diphyllin acetylapioside, a 5-lipoxygenase inhibitor from Haplophyllum hispanicum. Planta Med. 68 (2002) 359-360
21. Puricelli L., Innocenti G., Piacente S., Caniato R., Filippini R., and Cappelletti E.M. Production of lignans by Haplophyllum patavinum in vivo and in vitro. Heterocycles 56 (2002) 607-612
22. Ro D.K., Mah N., Ellis B.E., and Douglas D.J. Functional characterization and subcellular localization of poplar (Populus trichocarpa × Populus deltoides) cinnamate 4-hydroxylase. Plant Physiol. 126 (2001) 317-329
23. Russell D.W. The metabolism of aromatic compounds in higher plants. X. Properties of the cinnamic acid 4-hydroxylase of pea seedlings and some aspects of its metabolic and developmental control. J. Biol. Chem. 246 (1971) 3870-3878
24. Russell D.W., and Conn E.E. The cinnamic acid 4-hydroxylase of pea seedlings. Arch. Biochem. Biophys. 122 (1967) 256-258
25. Saleem M., Kim H.J., Ali M.S., and Lee Y.S. An update on bioactive plant lignans. Nat. Prod. Rep. 22 (2005) 696-716
26. Sandermann Jr. H. Plant metabolism of xenobiotics. Trends Biochem. Sci. 17 (1992) 82-84
27. Schmidt T.J., and Vößing S. A novel aryldihydronaphthalene lignan from Linum perenne L. Planta Med. 72 (2006) 1006
28. Schmidt W., Peters S., and Beerhues L. Xanthone 6-hydroxylase from cell cultures of Centaurium erythraea RAFN and Hypericum androsaemum L. Phytochemistry 53 (2000) 427-431
29. St-Pierre B., and De Luca V. A cytochrome P-450 monooxygenase catalyzes the first step in the conversion of tabersonine to vindoline in Catharanthus roseus. Plant Physiol. 109 (1995) 131-139
30. von Heimendahl C.B.I., Schäfer K.M., Eklund P., Sjöholm R., Schmidt T.J., and Fuss E. Pinoresinol-lariciresinol reductases with different stereospecificity from Linum album and Linum usitatissimum. Phytochemistry 66 (2005) 1254-1263
31. Werck-Reichhardt D. Cytochrome P450 in phenylpropanoid metabolism. In: Kingsley N. (Ed). Drug metabolism and drug interactions vol. 12 (1995), Freund Publishing House, Tel Aviv 221-243
32. Xia Z.Q., Costa M.A., Péllisier H., Davin L.B., and Lewis N.G. Secoisolariciresinol dehydrogenase purification, cloning and functional expression. J. Biol. Chem. 276 (2001) 12614-12623
33. Yamamoto H., Inoue K., Li S.M., and Heide L. Geranylhydroquinone 3′′-hydroxylase, a cytochrome P-450 monooxygenase from Lithospermum erythrorhizon cell suspension cultures. Planta 210 (2000) 312-317