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The Prenyllipids of the Membranes of Higher Plants

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Abstract

The prenyllipids found in higher plants are either completely terpenoid in origin (simple), e.g., the carotenoids, or consist of a terpenoid and a non-terpenoid part (mixed), as is the case with ubiquinone. Terpenoids are biosynthesized from a basic branched five carbon unit, If we formally designate this unit ip, then two units join head to tail to give a monoterpene, ipip; further sequential head-to-tail additions lead to sesquiterpenes (ipipip), diterpenes (ipipipip), and polyprenols (8 or more ip units). If, however two sesquiterpene units join tail-to-tail, the result is a triterpene (ipipippipipi) and if two diterpenes join in this way a tetraterpene is formed. Typical examples of simple prenyllipids are given in Table 1. The mixed terpenoids with which we are mainly concerned are listed in Table 2. A diterpene phytol, or a closely related compound, is a constituent of all these compounds except the ubiquinones and plastoquinones, which contain a polyprenol side chain. The ubiquinone (Q) isoprenologue usually present is Q-9 or Q-10; i.e., the quinone residue with a side chain of nine (45C) or ten (50C) isoprene residues [38].

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References

  1. Beale, S.I., Castelfranco, P.A.: Biosynthesis of δ-aminolevulinic acid in higher plants. II. Formation of 14C-δ-aminolevulinic acid from labelled precursors in greening plant tissues. Plant Physiol. 53, 297–303 (1974)

    Article  PubMed  CAS  Google Scholar 

  2. Britton, G.: Biosynthesis of carotenoids. In: Chemistry and Biochemistry of Plant Pigments. Goodwin, T.W. (ed.) London: Academic Press, 1976, 2nd ed., Vol. 1., pp. 262–327

    Google Scholar 

  3. Brooker, J.D., Russell, D.W.: Subcellular localization of 3-hydroxy-3-methyl glutaryl coenzyme A reductase in Pisum sativum seedlings. Arch. Biochem. Biophys. 167, 730–737 (1975)

    Article  PubMed  CAS  Google Scholar 

  4. Brooks, J.L., Stumpf, P.K.: Fat metabolism in higher plants XXXIX. Properties of a soluble fatty acid biosynthesizing system from lettuce chloroplasts. Arch. Biochem. Biophys. 116, 108–116 (1966)

    Article  PubMed  CAS  Google Scholar 

  5. Buggy, M.J., Britton, G., Goodwin, T.W.: Stereochemistry of phytoene biosynthesis by isolated chloroplasts. Biochem. J. 114, 641–643 (1969)

    PubMed  CAS  Google Scholar 

  6. Cohen, R.Z., Goodwin, T.W.: The effect of red and far-red light on carotenoid synthesis by etiolated maize seedlings. Phytochemistry 1, 67–72 (1962)

    Article  CAS  Google Scholar 

  7. Douce, R., Holtz, R.B., Benson, A.A.: Isolation and properties of the envelope of spinach chloroplasts. J. Biol. Chem. 248, 7215–7222 (1975)

    Google Scholar 

  8. Ellis, R.J., Blair, E.E., Hartley, M.R.: The nature and function of chloroplast protein synthesis. In: Nitrogen Metabolism in Plants. Goodwin, T.W., Smellie, R.M.S. (eds.) Biochem. Soc. Symp. 38, 137–162 (1973)

    Google Scholar 

  9. Goodwin, T.W.: Biosynthesis of Vitamins. London: Academic Press 1964

    Google Scholar 

  10. Goodwin, T.W.: Terpenoids and chloroplast development. In: Biochemistry of Chloroplasts. Goodwin, T.W. (ed.) London: Academic Press, 1967, Vol. 2, pp. 721–733

    Google Scholar 

  11. Goodwin, T.W.: Biosynthesis by chloroplasts. In: Structure and Function of Chloroplasts. Gibbs, M. (ed.) Berlin: Springer, 1971a, pp. 215–276

    Google Scholar 

  12. Goodwin, T.W.: Biosynthesis of carotenoids. In: Carotenoids. Isler, O. (ed.) Basel: Birkhäuser, 1971b, pp. 577–636

    Google Scholar 

  13. Goodwin, T.W.: Comparative Biochemistry of the Carotenoids. London: Chapman and Hall, in press, 1978, 2nd ed.

    Google Scholar 

  14. Goodwin, T.W., Mercer, E.I.: Introduction to Plant Biochemistry. London: Pergamon Press, 1972, 359 pp.

    Google Scholar 

  15. Grumbach, K.H., Lichtenthaler, H.K.: Photo-oxidation of the plastohydroquinone pool during onset of photosynthesis. Proc. 3rd Int. Cong. Photosynthesis, 1974, p. 516

    Google Scholar 

  16. Janiszowska, W., Michalski, W., Kasprzyk, S.: Polyprenol quinones and α-tocopherol in Calendula officinalis. Phytochemistry 15, 125–127 (1976)

    Article  CAS  Google Scholar 

  17. Kemp, R.J., Mercer, E.I.: The sterol esters of maize seedlings. Biochem. J. 110, 111–118 (1968)

    PubMed  CAS  Google Scholar 

  18. Kirk, J.T.O., Tilney-Bassett, R.A.E.: The Plastids. London: W.H. Freeman, 1967, 608 pp.

    Google Scholar 

  19. Kleudgen, H.K., Lichtenthaler, H.K.: Induction and reversion of prenyl-lipid synthesis in etiolated barley seedlings by red and far-red light. Proc. 3rd Int. Cong. Photosynthesis, 1974, pp. 2017–2020

    Google Scholar 

  20. Knapp, F.F., Aexel, R.T., Nicholas, H.J.: Sterol biosynthesis in subcellular particles of higher plants. Plant Physiol. 44, 442–446 (1969)

    Article  PubMed  CAS  Google Scholar 

  21. Lichtenthaler, H.K.: Plastoglobuli und Piastidenstruktur. Ber. Dtsch. Bot. Ges. 79, 82–88 (1966)

    CAS  Google Scholar 

  22. Lichtenthaler, H.K.: Localization and functional concentrations of lipoquinones in chloroplasts. In: Progress in Photosynthetic Research. Metzner, H. (ed.) 1969, Vol. 1, pp. 304–314

    Google Scholar 

  23. Lichtenthaler, H.K.: Control of light induced carotenoid synthesis in Raphanus seedlings by phytochrome. Physiol. Plantarum 34, 357–358 (1975)

    Article  CAS  Google Scholar 

  24. Lichtenthaler, H.K., Sprey, B.: Über die osmiophilen globularen Lipideinschlüsse der Chloro-plasten. Z. Naturforsch. 21, 690–697 (1966)

    Google Scholar 

  25. Lichtenthaler, H.K., Straub, V., Grumbach, K.H.: Unequal formation of prenyl-lipids in a plant tissue culture and in leaves of Nicotiana Tabacum L. Plant Sci. Lett. 4, 61–65 (1975)

    Article  CAS  Google Scholar 

  26. Liljenberg, C.: The effect of light on the phytolization of chlorophyllide a and the spectral dependence of the process. Physiol. Plantarum 19, 848–853 (1966)

    Article  CAS  Google Scholar 

  27. Mercer, E.I., Treharne, K.J.: Occurrence of sterols in chloroplasts. In: Biochemistry of Chloroplasts. Goodwin, T.W. (ed.) London: Academic Press 1966, Vol. 1, pp. 181–186

    Google Scholar 

  28. Ogawa, T., Obata, F., Shibata, K.: The pigment proteins in spinach chloroplasts. Biochim. Biophys. Acta 112, 223–234 (1966)

    Article  PubMed  CAS  Google Scholar 

  29. Pennock, J.F., Janiszowska, W.: Biochemistry of vitamin E in plants. Vitamins and Hormones (in press) (1976)

    Google Scholar 

  30. Radunz, A., Schmid, G.H.: Reactions of antisera to lutein and plastoquinone with chloroplast preparations and their effects on photosynthetic electron transport. Z. Naturforsch. 28C, 36–44 (1973)

    Google Scholar 

  31. Schnarrenberger, L., Mohr, H.: Carotenoid synthesis in mustard seedlings as controlled by phytochrome and inhibitors. Planta 94, 296–307 (1970)

    Article  CAS  Google Scholar 

  32. Sprey, B., Laetsch, W.M.: Chloroplast envelopes of Spinach oleracea L. II. Ultrastructure of chloroplast envelopes and lamellae. Z. Pflanzenphysiol. 78, 146–163 (1976a)

    Google Scholar 

  33. Sprey, B., Laetsch, W.M.: Chloroplast envelopes of Spinach oleracea L. III. Freeze-fracturing of chloroplast envelopes. Z. Pflanzenphysiol. 78, 360–371 (1976b)

    Google Scholar 

  34. Stumpf, P.K.: Lipid biosynthesis in higher plants. In: Biochemistry of Lipids. Goodwin, T.W. (ed.) London: Butterworth, 1976, in press

    Google Scholar 

  35. Subbarayan, C., Kushwaha, S.C., Suzu, G., Porter, J.W.: Enzymic conversion of isopentenyl pyrophosphate-4–14C and phytoene-14C to acyclic carotenes by an ammonium sulphate-precipitated spinach enzyme system. Arch. Biochem. Biophys. 137, 547–557 (1970)

    Article  PubMed  CAS  Google Scholar 

  36. Thomas, G., Threlfall, D.R.: Synthesis of polyprenyltoluquinols from homogentisate and poly-prenyl pyrophosphates in particulate fractions of Euglena and sugar beet. Biochem. J. 142, 437–440 (1974)

    PubMed  CAS  Google Scholar 

  37. Thornber, J. P.: Chlorophyll-proteins: light-harvesting and reaction center components of plants. Ann. Rev. Plant Physiol. 26, 127–158 (1975)

    Article  CAS  Google Scholar 

  38. Threlfall, D.R., Griffiths, W.T.: Biosynthesis of terpenoid quinones. In: Biochemistry of Chloroplasts. Goodwin, T.W. (ed.) London: Academic Press, 1966, Vol. 2, pp. 257–282

    Google Scholar 

  39. Threlfall, D.R., Whistance, G.R.: Biosynthesis of isoprenoid quinones and chromanols. In: Aspects of Terpenoid Chemistry and Biochemistry. Goodwin, T.W. (ed.) London: Academic Press, 1971, pp. 357–404

    Google Scholar 

  40. Treharne, K.J., Mercer, E.I., Goodwin, T.W.: Incorporation of [14C] carbon dioxide and [2–14C]mevalonic acid into terpenoids of higher plants during chloroplast development. Biochem. J. 99, 239–245 (1966)

    PubMed  CAS  Google Scholar 

  41. Vernon, L.P., Ke, B., Mollenhauser, H., Shaw, E.R.: Composition and structure of spinach sub-chloroplast fragments obtained by the action of Triton X-100. In: Progress in Photosynthesis Research. Metzner, H. (ed.) Tübingen: IUBS, 1969, Vol. 1, 137–148

    Google Scholar 

  42. Wallwork, J.C., Crane, F.L.: The nature, distribution, function and biosynthesis of prenyl phytoquinones and related compounds. In: Progress in Phytochemistry. Reinhold, L., Liwschitz, Y. (eds.), New York: John Wiley, 1970, Vol. 2, pp. 267–341

    Google Scholar 

  43. Wellburn, A.R., Hemming, F.W.: Long chain polyisoprenoid alcohols in chloroplasts. In: The Biochemistry of Chloroplasts. Goodwin, T.W. (ed.). London: Academic Press, 1966, Vol. 1, pp. 173–188

    Google Scholar 

  44. Wellburn, A.R., Hemming, F.W.: The subcellular distribution and biosynthesis of castaprenols and plastoquinone in the leaves of Aesculus hippocastanum. Biochem. J. 104, 173–177 (1967)

    PubMed  CAS  Google Scholar 

  45. Whittle, K.J., Dunphy, P.J., Pennock, J.F.: Plastochromanol in the leaves of Hevea brasiliensis. Biochem. J. 96, 17C-19C (1965)

    PubMed  CAS  Google Scholar 

  46. Wild, A., Conrad, G., Zickler, H.-O.: Der Gehalt an Plastidenchinonen und Pigmenten von Zea mays und Atriplex rosea in Abhängigkeit von Lichtintensität und dem Alter der Pflanzen. Planta 103, 181–187 (1972)

    Article  CAS  Google Scholar 

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Goodwin, T.W. (1977). The Prenyllipids of the Membranes of Higher Plants. In: Tevini, M., Lichtenthaler, H.K. (eds) Lipids and Lipid Polymers in Higher Plants. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-66632-2_2

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  • DOI: https://doi.org/10.1007/978-3-642-66632-2_2

  • Publisher Name: Springer, Berlin, Heidelberg

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