THE BIOGENESIS OF TERPENOID ESSENTIAL OILS 243 T. B. Terpenoids in plants (1967) (Academic Press) Rickards, J. H. and Hendrickson, J. B. The biosynthesis of steroids, terpenes and acetogenins (1964) (Benjamin) Teisseire, P. Recherches 17 77 (1969). (2) Ruzicka, L. Isoprene rule and the biogcnesis of terpenic compounds. Experientia 9 357 (1953) Perspektiven der Biogenese und der Chemie der Terpene. Pure Appl. Cbem. 6 493 (1963). (3) Parker, W., Roberts, J. S. and Ramage, R. Sesquiterpene biogenesis. Quart. Rev. 21 331 (1967). (4) Popj•k, G. and Cornforth, J. W. Substrate stereochemistry in squalene biosynthesis. Biochem. J. 101 553 (1966). (5) Ruzicka, L. History of the isoprene rule. Proc. Chem. Soc. 341 (1959). (6) Tavormina, P. A., Gibbs, lX[. H. and Huff, J. W. The utilization of [t-hydroxy-ll-methyl- $-valerolactone in cholesterol biosynthesis. J. ,4 m. Chem. Soc. 7814498 (1956) Tavormina, P. A. and Gibbs, M. H. The metabolism of [t, ¾-dihydroxy-ll-methyl valeric acid by liver homogenates. J. Am. Chem. Soc. 78 6210 (1956). (7) Hanson, K. R. Applications of the sequence rule. I. Naming the paired ligands g,g at a tetrahedral atom Xggij. II. Naming the two faces of a trigonal atom Yghi. J. Am. Che•n. Soc. 88 2731 (1966). (8) PopjJtk, G. The biosynthesis of derivatives of allylic alcohols from [2-• 4C] mevalonate in liver enzyme preparations and their relation to synthesis of squalene. Tetrahedron Letters 19 (1959 No. 19) see atso Goodman, D. S. and Popj•k, G. Studies on the bio- synthesis of cholesterol, XII. Synthesis of allyl pyrophosphate from mevalonate and their conversion into squalene with liver enzymes. J. Lipid Res. 1 286 (1960). (9) Francis, M. J. O. and O'Connell, M. The incorporation of mevalonic acid into rose petal monoterpenes. Phytochem. 8 1705 (1969) see also Pasechnichenko, V. A. and Guseva, A. R. E sential oil biosynthesis by isolated rose p•tals. Bioche•n. U.S.S.R. 32 1020 (1967) Gaseva, A. R. and Pasechnicht. nko, V. A. Essential oil alcohols biosynthesis from a Rosa da•nascena x R. Gallira hybrid. Biocbem. U.S.S.R. 31 988 (1966). (10) Waller, G. R., Frost, G. M., Burieson, D., Brannon, D. and Zalkow, L. H. Biosynthesis of monoterpenoids by Santolina cha•naecyparissus L. Phytochem. 7 213 (1968). (11) B:,rch, A. J., B•ulter, D., Fryer, R. I., Thomson, P. J. and Willis, J. L. The biosynthesis of citrondial and of cineole in Eucalyptus. Tetrahedron Letters 1 (1959) No. 3 Neethling, L. P., Reiber, H. G. and Chichester, C. O. Biosynthesis of citral in Eucalyptus stai•eriana. Proc. Nat. Conf. Nucl. Energy, Pretoria, 451 (1963). (12) Happ, G. M. and Meinwald, J. Biosynthesis of arthropod secretions. I. Monoterpene synthesis in an ant (Acanthomyops claviger). J. Am. Chem. Soc. 87 2507 (1965). (13) Waldner, E. E., Schlatter, Ch. an3 Schm[d, H. Zur Btosynthese des Dendrolasins, eines Inhaltsstoffes der Am•ise Lasius fuliginosus LATR. Helv. Chim. Acta, 52 15 (1969). (14) Oguni, I., Oshima, K.. Imaseki, H. and Uritani, I. Biochemical studies on the terpene metabolism in sweet potato root tissue with blackrot. Agri. Biol. Che•n. 33 50 (1969) and refs. therein. (15) Birch, A. J., Ko•6r, M., Sheppard, N. and Winter, J. Studies in relation to biosynthesis. Part XXIX. The terpenoid chain of mycelianamide. J. Che•n. Soc. 1502 (1962). (16) Schiitte, H. R. and Leh•_eldt, J. Bi. osynthese von Nuphar luteurn alkaloids. Arch. Pharm. 298 461 (1965). (17) Bat•ersby, A. R., Barnett, A. R., Knowles, G. D. and Parsons, P. G. Seco-cyclopentane glucosides from Menyanthes trifoliata: foliamenthin, di-hydrofoliamenthin, and men- thiafolin. Chem. Comm. 1277 (1963) Loew, P., Szczepanski, Ch. V., Coscia, C. J. and Arigoni, D. The structure and biosynthesis of foliamenthin. Chem. Comm. 1276 (1968). (18) Attaway, J. A. and Buslig, B. S. The metabolism of linalool in Citrus plants. Phytoche•n. 8 1671 (1969) Potty, V. H., Moshonas, M. G. and Bruemmer, J. H. Cyclisation of linalool by enzyme preparation from orange. ,4 rch. Blochewn. 138 350 (1970) see however Cori, O. Terpene biosynthesis: utilisation of neryl pyrophosphate by an enzyme system from Pinus radiata seedlings. Arch. Blochewn. Biophys. 135 416 (1969) Escher, S., Loew, P. and Arigoni, D. The role of hydroxygeraniol and hydroxynerol in the bio- synthesis of loganin and indole alkaloids. Che•n. Comm. 823 (1970) Battersby, A. R., Brown, S. H. and Payne, T. G. Biosynthesis of loganin and the indole alkaloids from hydroxygeraniol-hydroxynerol. Che•n. Co•nm. 827 (1970). (19) Banthorpe, D. V. and Wirz-Justice, A. Terpene biosynthesis. Part I. Preliminary tracer
244 JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS studies on terpenoids and chlorophyll of Tanecetum vulgare L. J. Chem. Soc. C 541 (1969). (20) Beytia, E., Valenzuela, P. and Cori, O. Terpene biosynthesis: formation ofnerol, geraniol, and other prenols by an enzyme system from Pinus radiata seedlings. Arch. Biochem. Biophys. 129 346 (1969). (21) Sandermann, W. and Bruns, K. •rber die Biogenese des Limonens in Pinus pinea L. Naturwiss, 49 258 (1962). (22) Sandermann, W. and Bruns, K. Biogenese yon caryon in/Inethum graycoleus L. Planta _Med. 18 364 (1965). (23) Valenzuela, P., Cori, O. and Yudelevich, A. Occurrence of monoterpenes in Pinus radiata and utilization of labelled CO 2 and mevalonic acid. Phytochem. õ 1005 (1966). (24) Hefendehl, F. W. Beltrage zur Biogenese iitherischer •le, die Rolle der Kohlenwasser~ stoffe bei der Biogenese sauerstoffhaltiger Monoterpene. Planta Med. 15 121 (1967). (25) Stanley, R. G. Terpene formation in pine from mevalonic acid. Nature, 182j738 (1958). (26) Sandermann, W. and Schweers, W. •rber die Biogenese yon (l-pinen in Pimcs nigra austriaca. Tetrahedron Letters, 257 (1962). (27) Schweers, W. •rber die weirere umwandlung yon (l-pinen in Pinus ponderosa. Tetrahedron Letters, 4425 (1968). (28) Banthorpe, D. V. and Turnbull, K. W. The biosynthesis of thujane derivatives in higher plants. Chem. Comm. 177 (1966). (29) Achilladelis, B. and Hanson, J. R. Studi•s in terpenoid biosynthesis. III. The incorpora- tion of geranyl pyrophosphate into cineole. Phytochem. ? 1317 (1968) see also (11). (30) Arigoni, D. quoted by Loomis, W. D. in Pridham, J. B. Terpenoids in Plants 65 (1967). (Academic Press, London and New York). (31) Banthorpe, D. V. and Baxendale, D. The biosynthesis (-I-)- and (--)-camphor. Chem. Comm. 1553 (1968). (32) Sandermann, W. and Stockmann, H. Ober die Biogenese yon Pulegon. Chem. Ber. 91 930 (1958). (33) Sandermann, W. and Schweers, W. Ober die Biogenese yon Thujon in Thuja occidentalis. Tetrahedron Letters, 259 (1962). (34) Yamazaki, M., Usui, T. and Shibata, S. Biogenesis of plant products. II. Biogenesis of thymol. Chem. Pharm. Bull. 11 363 (1963). (35) Battu, R. G. and Youngken, H. W. Jr. Biogenesis of terpenoids in Mentha piperira. I. Monoterpenes. Lloydia 29 360 (1966) Burbott, A. J. and Loomis, W. D. Evidence for metabolic turnover of monoterpenes in peppermint. Plant Physiol. • 173 (1969) Hefendehl, F. W. Der Einbau yon Mevalonsaura in die Terpene des •.therischen yon Mentha piperira. Planta Med. 1• 66 (1966) I-Iafendehl, F. W., Underhill, E. \¾. and yon Rudloff, E. The biosynthesis of the oxygenated monoterpenes in mint. Phytochem. 6 823 (1967). (36) Reitsema, R. H., Cramer, F. J., Scully, N.J. and Chorney, W. Essential oil synthesis in mint. J. Pharm. Sci. 50 18 (1961). (37) Battaile, J. and Loomis, W. D. Biosynthesis of terpenes. II. The site and sequence of terpene formation in peppermint. Blochim. Biophys. Acta, 51 545 (1961). (38) Battaile, J., Burbott, A. J. and Loomis, XV. D. Monoterpene interconversions: metabolism of pulegone by a cell-free system from Mentha piperita. Phytochem. 7 1159 (1968). (39) B4gu4, J. P. Acquisitions r4centes en biosynth•se des alcoloides indoliques. Bull. Soc. Chim. France, 2545 (1969) Leete, E. Biosynthesis of quinine and related alkaloids. Acc. Chem. Res. 2 59 (1969). (40) Yeowell, D. A. and Schmid, H. Zur Biosynthese des Plumierids. Experientia 20 250 (1964) Hiini, J. E. S., Hittebrand, H., Schmid, H., Gr6ger, D., Johne, S. and Mothes, K. Zur Biosynthese des Verbenalins and Aucubins. Experientia 22 656 •t1966•' se Inouye, H., Ueda, S. and Nakemura, Y. Zur Biosynthese der bitter [ '•l•osi•e also der Gentianazeen, des Gentiopicrosids, des Swertiamarins and Swerosids. Tetrahedron Letters 3221 (1967) Coscia, C. J. and Guarnaccia, R. Biosynthesis of gentiopicroside, a novel monoterpene. J. Am. Chem. Soc. 89 1280 (1967) Gr6ger, D. and Simchen, P. Uber den Einbau yon Loganin in Gentiopikroside. Z. Natur. f. 24b 356 (1969) Coscia, C. J., Guarnaccia, R. and Botta, L. Monoterpene biosynthesis. I. Occurrence and mevalonoid origin of gentiopicroside and loganic acid in Swertia caroliniensis. Biochem. 8 5036 (1969).
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