Feeding of [5,5-2H2]-1-desoxy-D-xylulose and [4,4,6,6,6-2H5]-mevalolactone to a geosmin-producing Streptomyces sp. and Fossombronia pusilla

Phytochemistry

Volumn 61, Issue 7, 2002, Pages 827-834

  Spiteller, Dieter ^a   Jux, Andreas ^a   Piel, Jörn ^a   Boland, Wilhelm ^a  

^a MAX PLANCK INSTITUTE FOR CHEMICAL ECOLOGY   (Germany)

Author keywords

Biosynthesis; Desoxy D xylulose; Fossombronia pusilla; Geosmin; Liverwort; Mevalolactone; Streptomyces sp. JP95

Indexed keywords

(4,4,6,6,6 2H(5)) MEVALOLACTONE; (4,4,6,6,6-2H(5))-MEVALOLACTONE; 1 DEOXYXYLULOSE; DEHYDROGEOSMIN; DEUTERIUM; FARNESYL DIPHOSPHATE; GEOSMIN; ISOPRENOID PHOSPHATE; LACTONE; LACTONE DERIVATIVE; MEVALOLACTONE; NAPHTHOL DERIVATIVE; SESQUITERPENE; UNCLASSIFIED DRUG; XYLULOSE;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CHEMISTRY; CLASSIFICATION; CULTURE MEDIUM; CYCLIZATION; FOSSOMBRONIA PUSILLA; ISOTOPE LABELING; LIVERWORT; MASS SPECTROMETRY; METABOLISM; OXIDATION REDUCTION REACTION; STEREOCHEMISTRY; STEREOISOMERISM; STREPTOMYCES;

ALKYLATION; CYCLIZATION; DEUTERIUM; HEPATOPHYTA; LACTONES; NAPHTHOLS; OXIDATION-REDUCTION; POLYISOPRENYL PHOSPHATES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEREOISOMERISM; STREPTOMYCES; XYLULOSE;

FOSSOMBRONIA; FOSSOMBRONIA PUSILLA; STREPTOMYCES; STREPTOMYCES SP.;

EID: 0036900003     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0031-9422(02)00282-0     Document Type: Article

References (31)

1. Adam, K.P., Thiel, R., Zapp, J., Becker, H., 1998. Involvement of the mevalonic acid pathway and the glyceraldehydes-pyruvate pathway in terpenoid biosynthesis of the liverworts Ricciocarpos natans and Conocephalum conicum. Arch. Biochem. Biophys. 354, 181-187.
2. Ayer, W.A., Browne, L.M., Fung, S., 1976. Metabolites of bird's nest fungi. Part 6. The synthesis of (+/-)-cybullol and a new synthesis of (+/-)-geosmin. Can. J. Chem. 54, 3276-3282.
3. Bentley, R., Meganathan, R., 1981. Geosmin and methylisoborneol biosynthesis in streptomycetes - evidence for an isoprenoid pathway and its absence in non-differentiating isolates. FEBS Lett. 125, 220-222.
4. Bjurman, J., Kristensson, J., 1992. Production of volatile metabolites by the soft rot fungus Chaetomium globosum on building-materials and defined media. Microbios 72, 47-54.
5. Darriet, P., Pons, M., Lamy, S., Dubourdieu, D., 2000. Identification and quantification of geosmin, an earthy odorant contaminating wines. J. Agric. Food Chem. 48, 4835-4838.
6. Donath, J., Boland, W., 1995. Biosynthesis of acyclic homoterpenes - Enzyme selectivity and absolute configuration of the nerolidol precursor. Phytochemistry 39, 785-790.
7. Dupuy, H.P., Flick, G.J., Stangelo, A.J., Sumrell, G., 1986. Analysis for trace amounts of geosmin in water and fish. J. Am. Oil Chem. Soc. 63, 905-908.
8. Eisenreich, W,. Rohdich, F., Bacher A., 2001. Deoxyxylulose phosphate pathway to terpenoids. Trends Plant Sci. 268, 6302-6310, and references cited therein.
9. 12-terpenoid dehydrogeosmin in flower heads of Rebutia marsoneri Werd. (Cactaceae). Helv. Chim. Acta 76, 2547-2552.
10. Gerber, N.N., 1967. Geosmin an earthy-smelling substance isolated from actinomycetes. Biotechnol. Bioeng. 9, 321-327.
11. Gerber, N.N., 1968. Geosmin from microorganisms is trans-1,10-dimethyl-trans-9-decalol. Tetrahedron Lett. 25, 2971-2974.
12. Gerber, N.N., Lecheval, H.A., 1965. Geosmin an earthy-smelling substance isolated from actinomycetes. Appl. Microbiol. 13, 935-937.
13. Hamano, Y., Dairi, T., Yamamoto, M., Kuzuyama, T., Itoh, N., Seto, H., 2002. Growth-phase dependent expression of the mevalonate pathway in a terpenoid antibiotic-producing Streptomyces strain. Biosci. Biotechnol. Biochem. 66, 808-819.
14. Huber, U., Boland, W., 1995. Alkylation of angular cis-decalin epoxides with carbon-nucleophiles; mechanism, scope and limitations of a novel bridgehead-functionalization. Helv. Chim. Acta 78, 87-93.
15. Izaguirre, G., Hwang, C.J., Krasner, S.W., McGuire, M.J., 1982. Geosmin and 2-methylisoborneol from cyanobacteria in three water-supply systems. Appl. Environ. Microbiol. 43, 708-714.
16. Kaiser, R., Nussbaumer, C., 1990. 1,2,3,4,4a,5,8,8a-Octahydro-4-β,8a-α-dimethylnaphthalen-4a- β-ol (=dehydrogeosmin), a novel compound occurring in the flower scent of various species of Cactaceae. Helv. Chim. Acta 73, 133-139.
17. Kikuchi, T., Mimura, T., Harimaya, K., Yano, H., Arimoto, T., Masada, Y., Inoue, T., 1973. Odorous metabolite of blue-green algae Schizothrix muelleri Nageli collected in southern basin of Lake Biwa identification of geosmin. Chem. Pharm. Bull. 21, 2342-2343.
18. König, W.A., Gehrcke, B., Icheln, D., Evers, P., Donnecke, J., Wang, W.C., 1992. New, selectively substituted cyclodextrins as stationary phases for the analysis of chiral constituents of essential oils. HRC J. High Resol. Chromatogr. 15, 367-372.
19. Mattheis, J.P., Roberts, R.G., 1992. Identification of geosmin as a volatile metabolite of Penicillium expansum. Appl. Environ. Microbiol. 58, 3170-3172.
20. 7-sterol reductase. Proc. Natl. Acad. Sci. USA 95, 1899-1902.
21. Murray, K.E., Bannister, P.A., Buttery, R.G., 1975. Geosmin- important volatile constituent of beetroot (Beta vulgaris). Chem. Indust. 973-974.
22. Nilsson, T., Larsen, T.O., Montanarella, L., Madsen, J.O., 1996. Application of head-space solid-phase micro-extraction for the analysis of volatile metabolites emitted by Penicillium species. J. Microbiol. Methods 25, 245-255.
23. Piel, J., Boland, W., 1997. Highly efficient and versatile synthesis of isotopically labelled 1-deoxy-D-xylulose. Tetrahedron Lett. 38, 6387-6390.
24. Schwarz, M.K., 1994. Terpen-Biosynthese in Ginkgo Biloba. PhD Thesis, ETH Zürich.
25. Seto, H., Watanabe, H., Furihata, K., 1996. Simultaneous operation of the mevalonate and non-mevalonate pathways in the biosynthesis of isopentenyl diphosphate in Streptomyces aeriouvifer. Tetrahedron Lett. 37, 7979-7982.
26. Seto, H., Orihara, N., Furihata, K., 1998. Studies on the biosynthesis of terpenoids produced by actinomycetes. Part 4. Formation of BE-40644 by the mevalonate and nonmevalonate pathways. Tetrahedron Lett. 39, 9497-9500.
27. Spörle, J., Becker, H., Allen, N.S., Gupta, M.P., 1991. Occurrence of (-)-geosmin and other terpenoids in an axenic culture of the liverwort Symphyogyna brongniartii. Z. für Naturfors. C 46, 183-188.
28. Stanjek, V., Miksch, M., Lueer, P., Matern, U., Boland, W., 1999. Biosynthesis of psoralene: Mechanism of a cytochrome P450 catalyzed oxidative bond cleavage. Angew. Chem., Int. Ed. 38, 400-402.
29. Thiel, R., Adam, K.P., 2002. Incorporation of [1-C-13]1-deoxy-D-xylulose into isoprenoids of the liverwort Conocephalum conicum. Phytochemistry 9, 269-274.
30. Warmers, U., König, W.A., 2000. Biosynthesis of the gymnomitranetype sesquiterpenes in liverworts. Phytochemistry 53, 645-650.
31. Watson, S.B., Brownlee, B., Satchwill, T., McCauley, E., 1999. The use of solid phase microextraction (SPME) to monitor for major organoleptic compounds produced by chrysophytes in surface waters. Water Sci. Technol. 40, 251-256.