Geranylhydroquinone 3-hydroxylase, a cytochrome P-450 monooxygenase from Lithospermum erythrorhizon cell suspension cultures

Planta

Volumn 210, Issue 2, 2000, Pages 312-317

  Yamamoto, Hirobumi ^a,b   Inoue, Kenichiro ^c   Li, Shu Ming ^a   Heide, Lutz ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

^b NAGASAKI UNIVERSITY   (Japan)

^c GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

3 Hydroxy geranylhydroquinone; Cytochrome P 450; Geranylhydroquinone 3 hydroxylase; Lithospermum; Naphthoquinone; Shi konin

Indexed keywords

3 GERANYL 4 HYDROXYBENZOIC ACID; CARBON MONOXIDE; CYCLIZATION; CYTOCHROME C; CYTOCHROME P450 OXYGENASE; ENZYME INHIBITOR; ENZYME KINETICS; ENZYME LOCALIZATION; GERANYLHYDROQUINONE; GERANYLHYDROQUINONE 3 HYDROXYLASE; HYDROXYLATION; MICROSOME; NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; PH; SHIKONIN; SPECTROSCOPY; SUSPENSION CELL CULTURE;

BORAGINACEAE; LITHOSPERMUM; LITHOSPERMUM ERYTHRORHIZON;

EID: 0033984410     PISSN: 00320935     EISSN: None     Source Type: Journal    
DOI: 10.1007/PL00008139     Document Type: Article

References (37)

1. Bauer W, Zenk MH (1991) Two methylenedioxy bridge forming cytochrome P-450 dependent enzymes are involved in (s)-Grossbuchstabe stylopine biosynthesis. Phytochemistry 30: 2953-2961
2. 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
3. Clemens S, Hinderer W, Wittkampf U, Barz W (1993) Characterization of cytochrome P450-dependent isoflavone hydroxylases from chickpea. Photochemistry 32: 653-657
4. Deno H, Suga C, Morimoto T, Fujita Y (1987) Production of shikonin derivatives by cell suspension cultures of Lithospermum erythrorhizon. VI. Production of shikonin derivatives by a two-layer culture containing an organic solvent. Plant Cell Rep 6: 197-199
5. Fujita Y, Hara Y, Suga C, Morimoto T (1981) Production of shikonin derivatives by cell suspension cultures of Lithospermum erythrorhizon. II. A new medium for the production of shikonin derivatives. Plant Cell Rep 1: 61-63
6. Fukui H, Tani M, Tabata M (1992) An unusual metabolite, dihydroechinofuran, released from cultured cells of Lithospermum erythrorhizon. Phytochemistry 31: 519-521
7. Gaisser S, Heide L (1996) Inhibition and regulation of shikonin biosynthesis in suspension cultures of Lithospermun. Phytochemistry 41: 1065-1072
8. Graebe JE (1987) Gibberellin biosynthesis and control. Annu Rev Plant Physiol 38: 419-465
9. Heide L, Leistner E (1981) 2-Methoxylcarbonyl-3-prenyl-1,4-naphthoquinone, a metabolite related to the biosynthesis of mollugin and anthraquinones in Galium mollugo L. J Chem Soc pp 334-336
10. Heide L, Leistner E (1983) Enzyme activities in extracts of anthraquinone-containing cells of Galium mollugo. Phytochemistry 22: 659-662
11. Heide L, Tabata M (1987) Enzyme activities in cell-free extracts of shikonin-producing Lithospermum erythrorhizon cell suspension cultures. Phytochemistry 26: 1645-1650
12. Heide L, Floss HG, Tabata M (1989a) Incorporation of shikimic acid into p-hydroxybenzoic acid in Lithospermum erythrorhizon cell cultures. Phytochemistry 28: 2643-2645
13. Heide L, Nishioka N, Fukui H, Tabata M (1989b) Enzymatic regulation of shikonin biosynthesis in Lithospermum erythrorhizon cell cultures. Phytochemistry 28: 1873-1877
14. Hutchinson CR (1998) Combinatorial biosynthesis for new drug discovery. Curr Opin Microbiol 1: 319-329
15. Inouye H, Ueda S, Inoue K, Matsumura H (1979) Biosynthesis of shikonin in callus cultures of Lithospermum erythrorhizon. Phytochemistry 18: 1301-1308
16. Koblitz H (1988) Anthraquinones. In: Constabel F, Vasil IK (eds) Cell culture and somatic cell genetics of plants, vol. 5. Academic Press, San Diego, pp 113-139
17. Kochs G, Grisebach H (1987) Induction and characterization of a NADPH-dependent flavone synthase from cell cultures of soybean. Z Naturforsch 42c: 343-348
18. Linsmaier EM, Skoog F (1965) Organic growth factor requirements of tobacco tissue cultures. Physiol Plant 18: 100-127
19. Ledüc C, Birgel I, Müller R, Leistner E (1997) Isochorismate hydroxymutase from a cell-suspension culture of Galium mollugo L. Planta 202: 206-210
20. Löscher R, Heide L (1994) Biosynthesis of p-hydroxybenzoate from p-coumarate and p-coumaroyl-coenzyme A in cell-free extracts of Lithospermum erythrorhizon cell cultures. Plant Physiol 106: 271-279
21. Luckner M (1990) Derivatives of dehydroquinic acid, dehydroshikimic acid, shikimic acid and chorismic acid. In: Secondary metabolism in microorganisms, plants, and animals (3rd edn). Gustav Fischer, Jena, pp 323-339
22. Melzer M, Heide L (1994) Characterization of polyprenyldiphosphate: 4-hydroxybenzoate polyprenyltransferase from Escherichia coli. Biochim Biophys Acta 1212: 93-102
23. Mühlenweg A, Melzer M, Li SM, Heide L (1998) 4-Hydroxybenzoate 3-geranyltransferase from Lithospermum erythrorhizon: purification of a plant membrane-bound prenyltransferase. Planta 205: 407-413
24. Okamoto T, Yazaki K, Tahata M (1995) Biosynthesis of shikonin derivatives from L-phenykilanine via deoxyshikonin in Lithospermum cell cultures and cell-free extracts. Phytochemistry 38: 83-88
25. Ortiz de Montellano PR, Correia MA (1995) Inhibition of cytochrome P450 enzymes. In: Ortiz de Montellano PR (ed) Cytochrome P450: structure, mechanism, and biochemistry (2nd edn). Plenum Press, New York, pp 305-364
26. Petersen M (1997) Cytochrome P450-dependent hydroxylation in the biosynthesis of rosmarinic acid in Coleus. Phytochemistry 45: 1165-1172
27. Rüffer 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
28. Sieweke HJ, Leistner E (1992) o-Succinylbenzoate: coenzyme A ligase from anthraquinone producing cell suspension cultures of Galium mollugo. Phytochemistry 31: 2329-2335
29. Sommer S, Severin K, Camara B, Heide L (1995) Intracellular localization of geranylpyrophosphate synthase from cell cultures of Lithospermum erythrorhizon. Phytochemistry 38: 623-627
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. Tabata M (1996) The mechanism of shikonin biosynthesis in Lithospermum cell cultures. Plant Tis Cult Lett 13: 117-125
32. Tabata M, Fujita Y (1985) Production of shikonin by plant cell cultures. In: Zaitlin M, Day PR, Hollaender A (eds) Biotechnology in plant science. Academic Press, Orlando, Fla, pp 207-218
33. Tang YX, Suga T (1994) Evidence for the involvement of cytochrome P-450-dependent monooxygenases in the allylic hydroxylation of terpineols by Nicotiana tabacum cell cultures. Phytochemistry 37: 731-735
34. Tsukada M, Tabata M (1984) Intracellular localization and secretion of naphthoquinone pigments in cell cultures of Lithospermum erythorhizon. Planta Med 50: 338-341
35. Weische A, Johanni M, Leistner E (1987) Biosynthesis of o-succinylbenzoic acid I: Cell free synthesis of o-succinylbenzoic acid from isochorismic acid in enzyme preparations from vitamin K producing bacteria. Arch Biochem Biophys 256: 212-222
36. Yamaga Y, Nakanishi K, Fukui H, Tabata M (1993) Intracellular localization of p-hydroxybenzoate geranyltransferase, a key enzyme involved in shikonin biosynthesis. Phytochemistry 32: 633-636
37. Zor T, Selinger Z (1996) Linearization of the Bradford protein assay increases its sensitivity: theoretical and experimental studies. Anal Biochem 236: 302-308