Phenylalanine-independent biosynthesis of 1,3,5,8-tetrahydroxyxanthone: A retrobiosynthetic NMR study with root cultures of Swertia chirata

European Journal of Biochemistry

Volumn 270, Issue 14, 2003, Pages 2950-2958

  Wang, Chang Zeng ^a   Maier, Ulrich H ^a   Keil, Michael ^b   Zenk, Meinhart H ^a   Bacher, Adelbert ^c   Rohdich, Felix ^c   Eisenreich, Wolfgang ^c  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

^b BOEHRINGER INGELHEIM PHARMA GMBH AND CO KG   (Germany)

^c TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Hydroxybenzoate; Isotope labelling; NMR spectroscopy; Retrobiosynthesis; Xanthone

Indexed keywords

1,3,5,8 TETRAHYDROXYXANTHONE; 3 HYDROXYBENZOYL COENZYME A; BENZOIC ACID; CARBON 13; CINNAMIC ACID; COENZYME A; GLUCOSE; PHENYLALANINE; SHIKIMIC ACID; UNCLASSIFIED DRUG; XANTHONE DERIVATIVE;

ARTICLE; CHIRATA; CULTURE MEDIUM; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PLANT ROOT; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; REACTION ANALYSIS; STRUCTURE ANALYSIS; SWERTIA;

ACYL COENZYME A; BENZOIC ACID; CARBON ISOTOPES; CINNAMATES; GENTIANACEAE; GLUCOSE; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PHENYLALANINE; PHOSPHOENOLPYRUVATE; PLANT ROOTS; SHIKIMIC ACID; SUGAR PHOSPHATES; XANTHENES; XANTHONES;

GENTIANACEAE; SWERTIA;

EID: 0038037107     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1432-1033.2003.03669.x     Document Type: Article

References (25)

1. Bacher, A., Rieder, C., Eichinger, D., Fuchs, G., Arigoni, D. & Eisenreich, W. (1999) Elucidation of biosynthetic pathways and metabolic flux patterns via retrobiosynthetic NMR analysis. FEMS Microbiol. Rev. 22, 567-598.
2. 13C-labelled glucose. J. Biol. Chem. 272, 25474-25482.
3. 13C NMR study. Eur. J. Org. Chem. 1459-1465.
4. Hostettmann, K. & Hostettmann, M. (1989) Xanthones. In Methods in Plant Biochemistry, Vol. 1. Plant Phenolics (Harborne, J.B., ed.), pp. 493-508. Academic Press, London.
5. Hegnauer, R. & Hegnauer, M. (1992) Chemotaxonomie der Pflanze, Vol. X, pp. 463. Birhäuser-Verlag, Basel.
6. Floss, H.G. & Rettig, A. (1964) Biosynthesis with Gentianaceae. I. Biosynthesis of gentisin. Z. Naturforsch. 19b, 1103-1105.
7. Zenk, M.H. (1979) Recent work on cinnamoyl CoA derivatives. In Recent Advances in Phytochemistry, Vol. 12 Biochemistry of Plant Phenolics. (Swain, T., Harborne, J.B. & van Sumre, C.F., eds), pp. 139-176. Plenum Publishing Corporation, New York.
8. Beerhues, L. (1996) Benzophenone synthase from cultured cells of Centaurium erythraea. FEBS Lett. 383, 264-266.
9. Schmidt, W. & Beerhues, L. (1997) Alternative pathways of xanthone biosynthesis in cell cultures of Hypericum androsaemum L. FEBS Lett. 420, 143-146.
10. Lewis, J.R. & Gupta, P. (1971) Biosynthesis of xanthones in Gentiana lutea. J. Chem. Soc. C, 629-631.
11. Bennet, G.J. & Lee, H.-H. (1988) The biosynthesis of mangostin: the origin of the xanthone skeleton. J. Chem. Soc. Chem. Commun., 619-620.
12. Bennet, G.J., Lee, H.-H. & Das, N.P. (1990) Biosynthesis of mangostin. Part 1: the origin of the xanthone skeleton. J. Chem. Soc. Perkin. Trans. I, 2671-2676.
13. Abd El-Mawla, A.M.A., Schmidt, W. & Beerhues, L. (2001) Cinnamic acid is a precursor of benzoic acids in cell cultures of Hypericum androsaemum L. but not in cell cultures of Centaurium erythraea RAFN. Planta 212, 288-293.
14. Abd El-Mawla, A.M.A. & Beerhues, L. (2002) Benzoic acid biosynthesis in cell cultures of Hypericum androsaemum. Planta 214, 727-733.
15. Zenk, M.H. & Müller, G. (1964) Biosynthese von p-Hydroxybenzosäure und anderer Benzoesäuren in höheren Pflanzen. Z. Naturforsch. 19b, 398-405.
16. Zenk, M.H. (1965) Biosynthesis von Vanillin in Vanilla planifolia Andr. Z. Pflanzenphysiol. 53, 404-414.
17. Zenk, M.H. (1967) Pathways of salicyl alcohol and salicin formation in Salix purpurea. Phytochemistry 6, 245-252.
18. Fleet, G.W.J., Shing, T.K.M. & Warr, S.M. (1984) Enantio-specific synthesis of shikimic acid from D-mannose: formation of a chiral cyclohexene by intramolecular olefination of a carbohydrate-derived intermediate. J. Chem. Soc. Perkin Trans. 1, 905-908.
19. 2]shikimic acid. J. Labelled Compounds Radiopharm. 31, 589-594.
20. Eisenreich, W., Schwarzkopf, B. & Bacher, A. (1991) Biosynthesis of nucleotides, flavins, and deazaflavins in Methanobacterium thermoautotrophicum. J. Biol. Chem. 266, 9622-9631.
21. Bax, A., Freeman, R. & Frenkiel, T.A. (1981) An NMR technique for tracing out the carbon skeleton of an organic molecule. J. Am. Chem. Soc. 103, 2102-2104.
22. Eisenreich, W. & Bacher, A. (2000) Elucidation of biosynthetic pathways by retrodictive/predictive comparison of isotopomer patterns determined by NMR spectroscopy. Genetic Engineering, Principles and Methods (Setlow, J. K., ed.), Vol. 22, pp. 121-153. Kluwer Academic/Plenum Publisher, New York.
23. Zhou, H.-M., Liu, Y.-L., Blasko, G. & Cordell, G.A. (1989) Swertiabisxanthone-I from Swertia macrosperma. Phytochemistry 28, 3569-3571.
24. Eisenreich, W., Rohdich, F. & Bacher, A. (2001) The deoxyxylulose phosphate pathway to terpenoids. Trends Plant Sci. 6, 78-84.
25. Schuhr, C.A., Radykewicz, T., Sagner, S., Latzel, C., Zenk, M.H., Arigoni, D., Bacher, A., Rohdich, F. & Eisenreich, W. (2003) Quantitative assessment of crosstalk between the two isoprenoid biosynthesis pathways in plants by NMR spectroscopy. Phytochem. Rev. in press.