Formation of benzoquinol moiety in cornoside by salidroside mono-oxygenase, a cytochrome P450 enzyme, from Abeliophyllum distichum cell suspension cultures

Planta

Volumn 216, Issue 3, 2003, Pages 432-436

  Yamamoto, Hirobumi ^a   Hori, Mitsuko ^b   Kuwajima, Hiroshi ^c   Inoue, Kenichiro ^b  

^a NAGASAKI UNIVERSITY   (Japan)

^b GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

^c KINKI UNIVERSITY   (Japan)

Author keywords

Abeliophyllum; Cornoside; Cytochrome P450; Quinol; Quinone biosynthesis; Salidroside mono oxygenase

Indexed keywords

ALCOHOLS; ENZYMES; OXIDATION; OXYGEN; PH EFFECTS; PLANT CELL CULTURE;

MOLECULAR OXYGEN;

PLANTS (BOTANY);

ABELIOPHYLLUM; ABELIOPHYLLUM DISTICHUM; OLEACEAE;

BENZOQUINONE DERIVATIVE; CARBON MONOXIDE; CORNOSIDE; CYCLOHEXANONE DERIVATIVE; CYTOCHROME C; CYTOCHROME P450; GLUCOSIDE; MICONAZOLE; MIXED FUNCTION OXIDASE; NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; OXYGEN; PHENOL DERIVATIVE; REACTIVE OXYGEN METABOLITE; RHODIOLOSIDE;

ARTICLE; CELL CULTURE; CHEMISTRY; DRUG ANTAGONISM; METABOLISM; OLEACEAE; PH;

BENZOQUINONES; CARBON MONOXIDE; CELLS, CULTURED; CYCLOHEXANONES; CYTOCHROME C GROUP; CYTOCHROME P-450 ENZYME SYSTEM; GLUCOSIDES; HYDROGEN-ION CONCENTRATION; MICONAZOLE; MIXED FUNCTION OXYGENASES; NADP; OLEACEAE; OXYGEN; PHENOLS; REACTIVE OXYGEN SPECIES;

EID: 0038513924     PISSN: 00320935     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00425-002-0896-0     Document Type: Article

References (33)

1. Bao W, O'Malley DM, Whetten R, Sederoff RR (1993) A laccase associated with lignification in loblolly pine xylem. Science 260:672-674
2. Bentley R, Campbell IM (1974) Biological reactions of quinones. In: Patai S (ed) The chemistry of the quinonoid compounds, part 2. Wiley, London, pp 683-736
3. Berlin J, Barz W (1975) Oxidative decarboxylation of para-hydroxybenzoic acids by peroxidases under in vivo and in vitro conditions. Z Naturforsch 30c:650-658
4. Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248-254
5. Eigtved P, Jensen OS, Kjaer A, Wieczorkowska E (1976) Biosynthesis of a quinol glucoside in Cornus. Acta Chem Scand Ser B 30:182-184
6. Eppink MHM, Boeren SA, Verpoorte J, van Berkel WJH (1997) Purification and properties of 4-hydroxybenzoate 1-hydroxylase (decarboxylating), a novel flavin adenine dinucleotide-dependent monooxygenase from Candida parapsilosis CBS604. J Bacteriol 179:6680-6687
7. Friederich S, Rueffer M, Asakawa Y, Zenk MH (1999) Cytochromes P-450 catalyze the formation of marchantines A and C in Marchantia polymorpha. Phytochemistry 52:1195-1202
8. Fujita M, Oba K, Uritani I (1982) Properties of a mixed function oxygenase catalyzing ipomeamarone 15-hydroxylation in microsomes from cut-injured and Ceratocystis fimbriata-infected sweet potato root tissues. Plant Physiol 70:573-578
9. Graebe JE (1987) Gibberellin biosynthesis and control. Annu Rev Plant Physiol 38:419-465
10. Guntern A, Ioset J-R, Queiroz EF, Foggin CM, Hostettmann K (2001) Quinones from Heliotropium ovalifolium. Phytochemistry 58:631-635
11. Iijima F, Tsukita H, Ebizuka Y, Sankawa U (1987) Purification and properties of dihydrogeodin oxidase from Aspergillus terreus. J Biochem 101:11-18
12. Jensen SR (1992) Systematic implications of the distribution of iridoids and other chemical compounds in the Loganiaceae and other families of the Asteridae. Ann Mo Bot Gard 79:284-302
13. Kawamukai M (1998) Recent advance of the biosynthesis and the function of ubiquinone. Seikagaku 70:1344-1349
14. Kochs G, Grisebach H (1987) Induction and characterization of a NADPH-dependent flavone synthase from cell cultures of soybean. Z Naturforsch 42c:343-348
15. Kraus PF, Kutchan TM (1995) Molecular cloning and heterologous expression of a cDNA encoding berbamunine synthase, a C-O phenol-coupling cytochrome P450 from the higher plant Berberis stolonifera. Proc Natl Acad Sci USA. 9:2071-2075
16. Luetke-Brinkhaus F, Kleinig H (1987) Ubiquinone biosynthesis in plant mitochondria. Methods Enzymol 148:486-490
17. Marbois BN, Clarke CF (1996) The COQ7 gene encodes a protein in Saccharomyces cerevisiae necessary for ubiquinone biosynthesis. J Biol Chem 271:2995-3004
18. Moir M, Thomson RH (1973) Naturally occurring quinines. Part XXII. Terpenoid quinines in Cordia spp. J Chem Soc Perkin I:1352-1356
19. Murashige T, Skoog F (1962) Revised medium for rapid growth and bioassays with tobacco tissue cultures. Physiol Plant 15:473-497
20. Norris SR, Shen X, DellaPenna D (1998) Complementation of the Arabidopsis pds1 mutation with the gene encoding p-hydroxyphenylpyruvate dioxygenase. Plant Physiol 117:1317-1323
21. Ohe T, Mashino T, Hirobe M (1997) Substituent elimination from p-substituted phenols by cytochrome P450. ipso-Substitution by the oxygen atom of the active species. Drug Metab Dispos 25:116-122
22. Ortiz de Montellano PR, Correia MA (1995) Inhibition of cytochrome P450 enzymes. In: Ortiz de Montellano PR (eds) Cytochrome P450: structure, mechanism, and biochemistry, 2nd edn. Plenum, New York, pp 305-364
23. Papageorgiou VP, Assimopoulou AN, Couladouros EA, Hepworth D, Nicolaou KC (1999) The chemistry and biology of alkanin, shikonin, and related naphthazarin natural products. Angew Chem Int Edn 38:270-300
24. Peters S, Schmidt W, Beerhues L (1998) Regioselective oxidative phenol couplings of 2, 3′, 4, 6-tetrahydroxybenzophenone in cell cultures of Centaurium erythraea RAFN and Hypericum androsaemum L. Planta 204:64-69
25. Ros Barceló A (1995) Peroxidase and not laccase is the enzyme responsible for cell wall lignification in the secondary thickening of xylem vessels in Lupinus. Protoplasma 186:41-44
26. Rueffer M, Zenk MH (1994) Canadine synthase from Thalictrum tuberosum cell cultures catalyses the formation of the methylenedioxy bridge in berberine synthesis. Phytochemistry 36:1219-1223
27. Seya K, Endo K, Hikino H (1989) Structures of rengyosides A, B, and C, three glucosides of Forsythia suspensa fruits. Phytochemistry 28:1495-1498
28. Stadler R, Zenk MH (1993) The purification and characterization of a unique cytochrome P-450 enzyme from Berberis stolonifera plant cell cultures. J Biol Chem 268:823-831
29. Sterjiades R, Dean JFD, Gamble G, Himmelsbach DS, Eriksson KEL (1993) Extracellular laccases and peroxidases from sycamore maple (Acer pseudoplatanus) cell-suspension cultures. Planta 190:75-87
30. Tabata M (1988) Naphthoquinones. In: Constabel F, Vasil IK (eds) Cell culture and somatic cell genetics of plants, vol 5. Academic Press, San Diego, pp 99-111
31. Torssell KBG (1997) Natural product chemistry: a mechanistic, biosynthetic and ecological approach. Swedish Pharmaceutical Press, Stockholm, pp 146-148
32. Wallace G, Fry SC (1999) Action of diverse peroxidases and laccases on six cell wall-related phenolic compounds. Phytochemistry 52:769-773
33. Yamamoto H, Yoshida K, Kondo Y. Inoue K (1998) Production of cornoside in Abeliophyllum distichum cell suspension cultures. Phytochemistry 48:273-277