Abstract
Isolated chloroplasts from spinach leaf cells, chloroplast subfractions, and a cell-free system of the cyanobacterium Synechococcus CCAP 6312 incorporated [1-14C]isopentenyl pyrophosphate in high yields into prenyl lipids. Products were polyprenols (C20, C45) chlorophylls, quinoid compounds, and fatty acid prenyl esters; prenyl pyrophosphates occurred in trace amounts, and carotenes were only formed to a limited extent in the Synechococcus system. The formation of fatty acid prenyl esters, which is described here for the first time, was found to occur in two different ways in the chloroplast system; by an acyl-CoA: polyprenol acyltransferase reaction associated with the envelope membranes and by a transesterification reaction from chlorophyll associated with the thylakoids. Endogenous fatty acid prenyl esters made up about 3% by weight of total lipids in spinach chloroplasts and were also found to be natural constituents of the cyanobacterial cells.
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Abbreviations
- Chl:
-
chlorophyll
- ChlGG :
-
chlorophyll a containing a geranylgeranyl side chain
- IPP:
-
isopentenyl pyrophosphate
References
Aoki, M., Hirano, M., Takahashi, Y., Katoh, S. (1983) Contents of cytochromes, quinones and reaction centers of photosystem I and II in a cyanobacterium Synechococcus sp. Plant Cell Physiol. 24, 517–525
Beyer, P., Kleinig, H. (1984) In vitro synthesis of C15-C66 polyprenols in a cell-free system of Myxococcus fulvus and determination of chain length by HPLC. Methods Enzymol. (in press)
Beyer, P., Kreuz, K., Kleinig, H. (1980) β-Carotene synthesis in isolated chromoplasts from Narcissus pseudonarcissus. Planta 150, 435–438
Bligh, E.S., Dyer, W.J. (1959) A rapid method of total lipid extraction and purification. Can. J. Biochem. Physiol. 37, 911–917
Block, M.A., Joyard, J., Douce, R. (1980) Site of synthesis of geranylgeraniol derivatives in intact spinach chloroplasts. Biochim. Biophys. Acta 631, 210–219
Bötsch, F. (1960) Vorkommen und Bestimmung von Phytol. Dissertation, University Würzburg (ex Steffens et al. 1976)
Carr, N.G., Hallaway, M. (1966) Quinones of some blue-green algae. In: Biochemistry of chloroplasts, vol. I, pp. 159–163, Goodwin, T.W., ed. Academic Press, New York
Camara, B., Bardat, F., Monéger, R. (1982) Sites of biosynthesis of carotenoids in Capsicum chromoplasts. Eur. J. Biochem. 127, 255–258
Clarke, J.E., Sandmann, G., Bramley, P.M., Böger, P. (1982) Carotene biosynthesis with isolated photosynthetic membranes. FEBS Lett 140, 203–206
Csupor, L. (1970) Das Phytol in vergilbten Blättern. Planta Med. 19, 37–41
Douce, R. (1973) Site of biosynthesis of galactolipids in spinach chloroplasts. Science 183, 852–853
Douce, R., Holtz, R.B., Benson, A.A. (1973) Isolation and properties of the envelope of spinach chloroplasts. J. Biol. Chem. 248, 7215–7222
Douce, R., Joyard, J. (1981) Does the plastid envelope derive from the endoplasmatic reticulum. Trends Biochem. Sci. 6, 237–239
Duncombe, W.G. (1963) The colorimetric micro-determination of long-chain fatty acids. Biochem. J. 88, 7–10
Fiedler, E., Soll, J., Schultz, G. (1982) The formation of homogentisate in the biosynthesis of tocopherol and plastoquinone in spinach chloroplasts. Planta 155, 511–515
Frosch, S., Mohr, H. (1980) Analysis of light controlled accumulation of carotenoids in mustard (Sinapis alba L.) seedlings. Planta 148, 279–286
Joyard, J., Stumpf, P.K. (1980) Characterization of an acylcoenzyme A thioesterase associated with the envelope of spinach chloroplasts. Plant Physiol. 65, 1039–1043
Kenyon, C.N. (1972) Fatty acid composition of unicellular strains of blue-green algae. J. Bacteriol. 109, 827–834
Kleinig, H., Liedvogel, B. (1979) On the energy requirement of fatty acid synthesis in spinach chloroplasts in the light and in the dark. FEBS Lett. 101, 339–342
Kreuz, K., Kleinig, H. (1981) Chlorophyll synthetase in chlorophyll-free chromoplasts. Plant Cell Rep 1, 40–42
Kreuz, K., Kleinig, H. (1984) Prenyl lipid synthesis in spinach leaf cells. Compartmentation of enzymes for isopentenyl diphosphate formation. Eur. J. Biochem. 141, 531–535
Liljenberg, C. (1977a) The occurrence of phytyl pyrophosphate and acyl esters of phytol in irradiated dark-grown barley seedlings and their possible role in biosynthesis of chlorophyll. Physiol. Plant. 39, 101–105
Liljenberg, C. (1977b) Chlorophyll formation: the phytylation step. In: Lipids and lipid polymers in higher plants, pp. 259–270, Tevini, M., Lichtenthaler, H.K., eds. Springer, Berlin, Heidelberg, New York
Liljenberg, C., Karunen, P. (1978) Changes in the content of phytyl and geranylgeranyl esters of germinating Polytrichum commune spores. Physiol. Plant. 44, 369–372
Lütke-Brinkhaus, F., Liedvogel, B., Kreuz, K., Kleinig, H., (1982) Phytoene synthase and phytoene dehydrogenase associated with envelope membranes from spinach chloroplasts. Planta 156, 176–180
Malhotra, K., Oelze-Karow, H., Mohr, H. (1982) Action of light on accumulation of carotenoids and chlorophylls in the milo shoot (Sorghum vulgare Pers). Planta 154, 654–655
Margulis, L. (1970) Origin of eukaryotic cells. Yale University Press, New Haven, Connecticut
Omata, T., Murata, N. (1983) Isolation and characterization of the cytoplasmatic membranes from the blue-green alga (Cyanobacterium) Anacystis nidulans. Plant Cell Physiol. 24, 1101–1112
Rippka, R., Deruelles, J., Waterbury, J.B, Herdman, M., Stanier, R.Y. (1979) Generic assignments, strain histories and properties of pure cultures of cyanobacteria. J. Gen. Microbiol. 111, 1–61
Schacterle, G.R., Pollak, R.L. (1973) A simplified method for the quantitative assay of small amounts of protein in biologic material. Anal. Biochem. 51, 654–655
Schultz, G., Ellerbrock, B.H., Soll, J., (1981) Site of prenylation reaction in synthesis of phylloquinone (Vitamin K1) by spinach chloroplasts. Eur. J. Biochem. 117, 329–332
Soll, J., Douce, R., Schultz, G. (1980a) Site of biosynthesis of α-tocopherol in spinach chloroplasts. FEBS Lett 112, 243–246
Soll, J., Kemmerling, M., Schultz, G. (1980b) Tocopherol and plastoquinone synthesis in spinach chloroplast subfractions. Arch. Biochem. Biophys 204, 544–550
Soll, J., Schultz, G. (1981) Phytol synthesis from geranylgeraniol in spinach chloroplasts. Biochem. Biophys. Res. Commun. 99, 907–912
Soll, J., Schultz, G., Rüdiger, W., Benz, J. (1983) Hydrogenation of geranylgeraniol. Two pathways exist in spinach chloroplasts. Plant. Physiol. 71, 849–854
Steffens, D., Blos, I., Schoch, S., Rüdiger, W. (1976) Lichtabhängigkeit der Phytolakkumulation. Ein Beitrag zur Frage der Chlorophyll-Biosynthese. Planta 130, 151–158
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Lütke-Brinkhaus, F., Weiss, G. & Kleinig, H. Prenyl lipid formation in spinach chloroplasts and in a cell-free system of Synechococcus (Cyanobacteria): polyprenols, chlorophylls, and fatty acid prenyl esters. Planta 163, 68–74 (1985). https://doi.org/10.1007/BF00395899
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DOI: https://doi.org/10.1007/BF00395899