Abstract
The possible involvement of the amino acid leucine in the biosynthesis of isoprenoids has long been the subject of conjecture. The catabolic pathway for leucine in mammals was established in the early 1950’s, largely by the work of M.J. Coon et al. [15, 24, 36], as outlined in Scheme 1. It was subsequently shown that the same (3S)-antipode of 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA) (5) lies on the catabolic pathway of leucine [20, 37] (Scheme 1, a) and on the anabolic pathway from acetate to (3R)-me-valonic acid (MVA) (6) [16, 17] (Scheme 1, b). The latter is, of course, the well-established biosynthetic route to terpenoids and steroids, but the interesting question arises whether an alternative, if less important route to (3R)-MVA (6) might start from leucine, rather than acetate and proceed via HMG-CoA, incorporating the carbon skeleton of leucine intact [but for loss of C—1 in the conversion of (1) to (2)].
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
Similar content being viewed by others
References
Aberhart DJ, Tann C-H (1981) Substrate stereochemistry of isovaleryl-CoA dehydrogenase. Elimination of the 2-pro-R hydrogen in biotin-deficient rats. Bioorg Chem:200–205
Allison AJ, Butcher DN, Connolly JD, Overton KH (1968) Paniculides A, B, C. Bisabolenoid lactones from tissue cultures of Andrographispaniculata. Chem Commun: 1493–1494
Anastasis P, Freer I, Gilmore C, Mackie H, Overton K, Swanson S (1982) Cyclisation of far-nesylpyrophosphate to 7-bisabolene in tissue cultures of Andrographis paniculata. Chem Com-mun:268–270
Anastasis P, Overton K, Singh SB (1984) Synthesis of (2RS)-[3–13C]- and (2RS)-[3–14C]-leu-cine. J Lab Compds Radiopharm:393–400
Benveniste P, Heintz R (1974) Plant sterol metabolism. Enzymatic cleavage of the 9 β, 19 β cyclopropane ring of cyclopropyl sterols in bramble tissue cultures. J Biol Chem 249:4267–4274
Benveniste P, Hirth L, Ourisson G (1966) Biosynthesis of sterols in tobacco tissue culture II. Details of biosynthesis of phytosterols. Phytochemistry 5:45–58
Benveniste P, Hewlins MJT, Fritig B (1969) Biosynthesis of sterols in cultured tobacco tissues. Kinetics of formation of sterols and their precursors. Eur J Biochem 9:526–533
Bloch K (1944) Some aspects of the metabolism of leucine and valine. J Biol Chem:255–263
Bloch K, Clark LC, Harary I (1954) Utilization of branched chain acids in cholesterol synthesis. J Biol Chem:687–699
Blunt JW, Stothers JB (1977) 13C Nmr spectra of steroids — a survey and commentary. Org Mag Res 9:439–464
Brady RO, Gurin S (1951) The synthesis of radioactive cholesterol and fatty acids in vitro. J Biol Chem 189:371–377
Cardillo R, Fuganti C, Ghiringhelli D, Grasselli P (1977) Pattern of incorporation of leucine samples asymmetrically labelled with 13C in the isopropyl unit into the C5 -isoprenoid units of echinuline and flavoglaucine. Chem Commun:474–476
Chadwick DJ, Williams DH (1974) The full assignment of the carbon-13 nuclear magnetic resonance spectrum of 5 α-cholestan-3 β-ol with the aid of the lanthanide shift reagent Yb(dpm)3. J Chem Soc Perkin 11:1903–1908
Chichester CO, Yokoyama H, Nakayama TOM, Lukton A, Mackinney G (1959) Leucine metabolism and carotene biosynthesis. J Biol Chem 234:598–602
Coon MJ, Kupiecki FP, Decker EE, Schlesinger MJ, Del Campillo A (1959) The enzymic synthesis of branchedchain acids. In: Wolstenholme GEW, O’Connor M (eds) Ciba Foundation Symposium biosynthesis of terpenes and sterols. Churchill, London, pp 62–74
Cornforth JW (1968) Terpenoid biosynthesis. Chem Br 4:102–106
Cornforth JW (1974) Enzymes and stereochemistry. Tetrahedron 30:1515–1524
Fuganti C, Grasselli P, Pedrocchi-Fantoni G (1979) On the mode of incorporation of leucine samples labelled at positions 5 and 2 with 3H and 14C into the isoprenylated tryptophan derivative echinuline horn Aspergillus amstelodami. Tetrahedron Lett:245 3–2454
Goodwin TW, Lijinski W (1952) Carotene production by Phycornyces blakesleeanus. The effect of different amino acids when used in media containing low concentrations of glucose. Biochem J 50:268–273
Higgins MJP, Kornblatt JA, Rudney H (1972) Acyl-CoA ligases. In: Boyer PD (ed) The enzymes, vol VII, 3rd edn. Academic Press, London New York, pp 407–434
Lowry LK, Chichester CO (1971) The role of thiamine, leucine and C02 in the biosynthesis of carotenes by the mould Phycomyces blakesleeanus. Phytochemistry 10:323–333
Mackie H, Overton KH (1977) Hydrolysis and isomerization of trans,trans-farnesyl diphosphate by Andrographis tissue-culture enzymes. Eur J Biochem: 101–106
Mackinney G, Nakayama TOM, Buss CD, Chichester CO (1952) Carotenoid production in Phycomyces. J Am Chem Soc:3456–3457
Meister A (1965) Intermediary metabolism of amino acids. Biochemistry of the amino acids, vol II, 2nd edn. Academic Press, London New York, pp 742–747
Mertz D (1970) Light-stimulated incorporation of L-leucine into the gibberellin of Gibberella fujikuroi. Plant Cell Physiol 11:273–279
Mori Y (1961) Incorporation of leucine into hop resins. Bull Brew Sci 6:28–31 (see Chem Abstr (1964) 60:7150 b)
Oshima-Oba K, Sugiura I, Uritani I (1969) The incorporation of leucine [U-14C] into ipomea-marone. Agric Biol Chem 33:586–591
Overton KH, Picken DJ (1976) Biosynthesis of bisabolene by callus cultures of Andrographis paniculata. Chem Commun: 105–106
Overton KH, Roberts FM (1973) Biosynthesis of 2-trans, 6-trans- and 2-cis, 6-trans-farnesols by soluble enzymes from tissue cultures of Andrographis paniculata. Chem Commun: 378–379
Overton KH, Roberts FM (1974) Stereochemistry of C-1 hydrogen exchange in the interconversion of trans, trans- and cis, trans-farnesols by soluble enzymes from tissue cultures of An-drographis paniculata. Chem Commun:385–386
Overton KH, Roberts FM (1974) Biosynthesis of trans,trans- and cis, trans-farnesols by soluble enzymes from tissue cultures of Andrographis paniculata. Biochem J:585–592
Overton KH, Roberts FM (1974) Interconversion of trans,trans- and cis, trans-farnesol by enzymes horn Andrographis. Phytochemistry:2741–2743
Overton KH, Singh SB (1984) Synthesis of (4R)- and (4S)-[5–13C]leucine. Unpublished results
Peter HG, Woggon W-D, Schlatter C, Schmid H (1977) Einbauversuche mit Geraniol und Far-nesol in Cantharidin. Helv Chim ACta 60:844–866
Picken DJ (1977) Biosynthesic studies in plant tissue culture. PhD Thesis, Glasgow, pp 71, 79–82
Rodwell VW (1969) Carbon catabolism of amino acids. In: Greenberg DM (ed) Metabolic pathways, part II, vol HI, 3rd edn. Academic Press, London New York, pp 191–235
Stegink LD, Coon MJ (1968) Stereospecificity and other properties of highly purified β-hy-droxy-β-methylglutaryl coenzyme A. Cleavage enyzme from bovine liver. J Biol Chem 243: 5272–5279
Suga T, Hirata T, Shishibori F, Tange K (1974) First proof of the biosynthesis of isoprenoid from amino acid in higher plant. The incorporation of leucine into linalool. Chem Lett: 189–192
Suga T, Hirata T, Tange K (1975) Biosynthesis of isoprenoid from amino acid in higher plant Incorporation of L-leucine and L-valine into geraniol and citonellol. Chem Lett:243–246
Suga T, Tange K, Lecho K, Hirata F (1980) Biosynthesis of triterpenoids from amino acids in Pisum sativum. The distribution of the radioactivity in squalene biosynthesised from radioiso-topically labelled L-leucine and L-valine. Phytochemistry 19:67–70
Tavormina PA, Gibbs MH (1956) The metabolism of β,7-dihydroxy-β-methylvaleric acid by liver hornogenates. J Am Chem Soc 78:6210
Wigfield DC, Wren BP (1977) Indole alkaloid biosynthesis. An investigation into leucine as a possible precursor of the monoterpene portion of vindoline. Bioorg Chem 6:511–519
Wolf DE, Hoffman CH, Aldrich PE, Skeggs HR, Wright LD, Folkers K (1957) Determination of structure of β, δ-dihydroxy-β-methylvaleric acid. J Am Chem Soc 79:1486–1487
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1985 Springer-Verlag Berlin Heidelberg
About this paper
Cite this paper
Overton, K.H. (1985). The Role of Leucine in Terpenoid Metabolism: Incorporation of Leucine into Sesquiterpenoids and Phytosterols by Andrographis Tissue Cultures. In: Neumann, KH., Barz, W., Reinhard, E. (eds) Primary and Secondary Metabolism of Plant Cell Cultures. Proceedings in Life Sciences. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-70717-9_22
Download citation
DOI: https://doi.org/10.1007/978-3-642-70717-9_22
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-70719-3
Online ISBN: 978-3-642-70717-9
eBook Packages: Springer Book Archive