Proline Analogues

The discovery of substantial quantities of proline analogues (Figure 7) in the leaves of some Melaleuca species highlights a potentially commercial source of industrial chemical compounds. Coupled with the recent interest in biochemical changes in plants suffering water and salinity stress, is the ability of drought resistant species to accumulate proline and proline analogues including glycinebetaine. Investigations have shown that, when subject to water or salinity stress under glass house or laboratory conditions, proline (27) and trans-4-hydroxy-N-methyl-L-proline (29) in M. lanceolata and trans-4-hydroxy-N-methyl-L-proline (29) and N, N'-dimemyl-trans-4-hydroxy-L-proline (30) levels in M. uncinata increased (Naidu et al. 1987).

Further investigations are now translating these laboratory findings into field situations as trial plantings of M. bracteata, M. uncinata, M. lanceolata, M. populiflora and M. viridiflora are being established in eastern and north eastern Australia (Naidu 1997). The best species for the commercial production of proline analogues will be chosen for the production of natural agricultural chemicals which will alleviate stress and increase biomass yields in pastures and crops.


Association Française de Normalisation (1996) Huile essentielle de Melaleuca type terpinène-4-ol.

Huiles essentielles. Tome 2 (5e édition), AFNOR, Paris La Défense, pp. 529-536. Baker, R.T. and Smith, H.G. (1906) Essential oil of Melaleuca thymifolia. J. Proc. Roy. Soc. NSW, 40, 60.

Baker, R.T. and Smith, H.G. (1907) Essential oil of Melaleuca uncinata and M.nodosa. J. Proc. Roy. Soc. NSW, 41, 196.

Baker, R.T. and Smith, H.G. (1910) Essential oil of Melaleuca genistifolia Sm. (M.bracteata). J. Proc. Roy. Soc. NSW, 44, 592.

Baker, R.T. and Smith, H.G. (1911) Essential oil of Melaleuca genistifolia, M. gibbosa and M.

pauciflora. J. Proc. Roy. Soc. NSW, 45, 365. Baker, R.T. and Smith, H.G. (1913) Essential oil of Melaleuca leucadendron. J. Proc. Roy. Soc. NSW, 47, 196.

Birch, A.J., Grimshaw, J., Speake, R.N., Gascoigne, R.M. and Hellyer, R.O. (1959) Tetrahedron Lett., 3, 15-18.

Bishop, C.D. (1995) Antiviral Activity of the Essential Oil of Melaleuca alternifolia (Maiden & Betche)

Cheel (Tea Tree) Against Tobacco Mosaic Virus. J. Essent. Oil Res., 7, 641-644. Bishop, C.D. and Thornton, I.B. (1997) Evaluation of the Antifungal Activity of the Essential Oils of Monarda citriodora var. citriodora and Melaleuca alternifolia on Post-Harvest Pathogens. J. Essent. Oil Res., 9, 77-82.

British Pharmaceutical Codex (1949) Oleum Melaleucae, General Medical Council, London, pp. 597598.

Brophy, J.J., Boland, D.J. and Lassak, E.V. (1989a) Leaf Essential Oils of Melaleuca and Leptospermum species from tropical Australia. In D.J.Boland (ed.). Trees for the Tropics, ACIAR, Canberra, pp. 193-203.

Brophy, J.J., Davies, N.W., Southwell, I.A, Stiff, I.A. and Williams, L.R. (1989b) Gas Chromatographic Quality Control for Oil of Melaleuca Terpinen-4-ol Type (Australian Tea Tree). J. Agric. Food Chem. 37, 1330-1335.

Brophy, J.J. and Doran, J.C. (1996) Essential Oils of Tropical Asteromyrtus, Callistemon and Melaleuca

Species. ACIAR, Canberra pp. 76-77. Brophy, J.J, Lassak, E.V. and Boland, D.J. (1990) Steam volatile leaf oil of Melaleuca globifera R. Br,

M. lateriflora Benth, M. symphyocarpa F.Muell. and M. uncinata RFlav. Frag. J., 5, 43-48. Brophy, J.J. and Lassak, E.V. (1992) Steam volatile leaf oils of some Melaleuca species from Western

Australia. Flav. Frag. J. 7, 27-31. Buchi, G, Hofheinz, W. and Paukstelis, J.V. (1969) The synthesis of (-)-aromadendrene and related sesquiterpenes. J. Am. Chem. Soc., 91, 6473-6478. Butcher, P.A, Bell, J.C. and Moran, G.F. (1992) Patterns of genetic diversity and nature of the breeding system in Melaleuca alternifolia (Myrtaceae). Austral. J. Bot., 40, 365-375. Butcher, P.A, Doran, J.C. and Slee, M.U. (1994) Intraspecific variation in leaf oils of Melaleuca alternifolia (Myrtaceae). Biochemical Systematics and Ecology, 42, 419-430. Cheel, E. (1924) Notes on Melaleuca, with descriptions of two new species and a new variety. J. Proc.

Roy. Soc. NSW, 58, 89-197. Cocking, T.A. (1920) New method for the estimation of cineole in Eucalyptus oil. Pharm. J., 105, 8183.

Cornwell, C.P., Leach, D.N. and Wyllie, S.G. (1995) Incorporation of oxygen-18 into terpinen-4-ol from the H218O steam distillates of Melaleuca alternifolia (Tea Tree). J. Essent. Oil Res., 7, 613620. 2

Courtney, J.L., Lassak, E.V. and Speirs, G.B. (1983) Leaf wax constituents of some Myrtaceous species.

Phytochemistry, 22, 947-949. Croteau, R. (1987) Biosynthesis and catabolism of monoterpenoids. Chem. Rev., 87, 929-954. Davenport, J.B, Jones, T.G.H. and Sutherland, M.D. (1949) The essential oils of the Queensland flora. Part XXIII. A re-examination of the essential oil of Melaleuca linariifolia. Univ. Queensl. Pap., Dep. Chem., 1(36), 1-12. Deutscher Arzneimittel-Codex 1986 (1996) Teebaumol, Melaleucae aetheroleum, 8, Erganzung, T-

019, 1-3, Govi-Verlag Pharmazeutischer Verlag GMBH Frankfurt Am Main/Eschborn. Dung, N.X, Bao, P.Q. and Leclercq, P.A. (1994) Chemical composition of the leaf oil of Melaleuca parviflora Link from Vietnam. J. Essent. Oil Res. 6, 419-420. Dung, N.X. (1996) Center for Education and Development of Chromatography (EDC) of Vietnam. Personal communication.

Eisenreich, W., Sagner, S., Zenk, M.H. and Bacher, A. (1997) Monoterpenoid essential oils are not of mevalonoid origin. Tetrahedron Lett., 38, 3889-3892.

Erman, W.F. (1985) Chemistry of the Monoterpenes, Marcel Dekker, New York, pp. 826-827.

Faure, R., Ramanoelina, A.R.P., Rakotoniraing, O., Bianchini, J.P. and Gaydou, E.M. (1991) Two-dimensional nuclear magnetic resonance of sesquiterpenes. 4. Application to complete assignment of 1H and 13C NMR spectra of some aromadendrene derivatives. Magn. Resort. Chem., 29, 969971.

Fischer, N., Nitz, S. and Drawert, F. (1987) Original flavour compounds and the essential oil composition of majoram (Majorana hortensis Monech). Flav. Frag. J. 2, 55-61.

Fischer, N., Nitz, S. and Drawert, F. (1988) Original composition of majoram flavour and its changes during processing. J. Agric. Food Chem., 36, 996-1003.

Formacek, V. and Kubeczka, K.H. (1982) Essential Oils Analysis by Capillary Gas Chromatography and Carbon-13 NMR Spectroscopy, Wiley, Chichester.

Ghisalberti, E.L., Patalinghug, W.C., Skelton, B.W. and White, A.H. (1994) Structural studies of aromadendrane-1, 2-diols. Aust. J. Chem., 47, 943-949.

Guenther, E. (1948) The Essential Oils, Van Nostrand, New York.

Guenther, E. (1968) Australian tea tree oils. Report of a field survey. Perfum. Essent. Oil Rec., 59, 642-44.

Hallahan, T.W. and Croteau, R. (1988) Monoterpene biosynthesis: Demonstration of a geranyl pyrophosphate: sabinene hydrate cyclase in soluble enzyme preparations from sweet marjoram (Majorana hortensis). Arch. Biochem. Biophys., 264, 618-631.

Hallahan, T.W. and Croteau, R. (1989) Monoterpene biosynthesis: Mechanism and stereochemistry of the enzymic cyclisation of geranyl pyrophosphosate to (+)-cis- and (+)-trans-sabinene hydrate. Arch. Biochem. Biophys., 269, 313-326.

International Standards Organisation (1996) Oil of Melaleuca, Terpinen-4-ol Type, 4730, ISO, Geneva.

Johns, M.R., Johns, J.E. and Rudolph, V. (1992) Steam distillation of tea tree (Melaleuca alternifolia) oil. J. Sci. Food Agric. 58, 49-53.

Jones, G.P., Naidu, B.P., Paleg, L.G., Tiekink, E.R.T. and Snow, M.R. (1987) 4-Hydroxy-N methylproline analogues in Melaleuca spp. Phytochem., 26, 3343-3344.

Jones, T.G.H. (1936) Essential oils from the Queensland flora. Part X. Melaleuca linariifolia. Proc. Roy. Soc. Qld., 48, 48-50.

Jones, T.G.H. and Oakes, H.C. (1940) The crystalline solid formed in the oil of Melaleuca linariifolia. Univ. Queensl. Pap., Dep. Chem., 1(18), 1-3.

Kawakami, M., Sachs, R.M. and Shibamoto, T. (1990) Volatile constituents of essential oils obtained from newly developed tea tree (Melaleuca alternifolia) clones. J. Agric. Food Chem., 38, 16571661.

Kerrola, K. (1995) Literature review: Isolation of essential oils and flavour compounds by dense carbon dioxide. Food Rev. Int., 11, 547-573.

Koedam, A. (1987) Some aspects of essential oil preparation. In P.Sandra and C.Bicchi, (eds) Capillary Gas Chromatography in Essential Oil Analysis, Huethig, Heidelberg, pp. 13-27.

Laakso, P.V. (1966) Fractionation of tea tree oil (Melaleuca alternifolia). In Hanc, O. and Hubik, J. (eds) Scientiae Pharmaceuticae Proceedings of the 25th Congress of Pharmaceutical Sciences, Prague, 1965. Czechoslovakian Medical Press: Prague, 1, pp. 485-492.

Lassak, E.V. and McCarthy, T. (1983) Australian Medicinal Plants, Methuen, Sydney, p. 97.

Leach, D.N., Wyllie, S.G., Hall, J.G. and Kyratzis, I. (1993) The enantiomeric composition of the principal components of the oil of Melaleuca alternifolia. J. Agric. Food Chem., 41, 16271632.

Lichtenthaler, H.K., Schwender, J., Disch, A. and Rohmer, M. (1997) Biosynthesis of isoprenoids in higher plant chloroplasts proceeds via a mevalonate independent pathway. FEBS Lett., 400, 271-274.

Liener, I.E. (1996) Editorial. J. Agric. Food Chem., 44, 1.

Markham, J. (1996) Antimicrobial effectiveness of tea tree oil. In Conference Program and Papers, Tea Tree Oil into the 21st Century—The Proof and the Promise. Austteam. Lismore, pp. 30-37.

Naidu, B.P. (1997) Commonwealth Scientific and Industrial Research Organisation. Personal communication.

Naidu, B.P., Jones, G.P., Paleg, L.G. and Poljakoff-Mayber, A. (1987) Proline analogues in Melaleuca species: Response of Melaleuca lanceolata and M.uncinata to water stress and salinity. Aust. J. Plant Physiol., 14, 669-677.

Naves, Y.R. and Tullen, P. (1960) Die bisher beobachtete Hochstdrehung von terpinenol-4 betragt 48.3. Bull. Soc. Chim. France, 2123.

Ohloff, von G. and Uhde, G. (1965) Abosolute Konfiguration von Terpinenol-(4), Helv. Chim. Acta, 48, 10-28.

Penfold, A.R. (1925) The Essential Oils of Melaleuca linariifolia (Smith) and M.alternifolia (Cheel). J. Proc. Roy. Soc. NSW, 59, 306-325.

Penfold, A.R., Morrison, F.R. and McKern, H.H.G. (1948) Studies in the physiological forms of the Myrtaceae, Part II. The occurrence of physiological forms in Melaleuca alternifolia Cheel. Researches on the Essential Oils of the Australian Flora; Museum of Technology and Applied Science: Sydney 1, 18-19.

Russell, M., Southwell, I.A. and Stiff, I.A. (1997) NSW Agriculture. Unpublished results.

Southwell, I.A. (1973) Variation in the leaf oil of Eucalyptus punctata. Phytochem., 12, 1341-1343.

Southwell, I.A. (1988) Australian tea tree: Oil of Melaleuca, terpinen-4-ol type. Chem. in Aust., 55, 400-402.

Southwell, I.A. (1989) Terpenoid pathways in Australian tea trees. In S.C.Bhattacharyya, N.Sen and K.L.Sethi (eds) 11th International Congress of Essential Oils Fragrances and Flavours. New Delhi, India, 12-16 November, 1989. Oxford. New Delhi.

Southwell, I.A. and Stiff, I.A. (1989) Ontogenetical changes in monoterpenoids of Melaleuca alternifolia leaf. Phytochemistry, 28, 1047-1051.

Southwell, I.A. and Stiff, I.A. (1990) Differentiation between Melaleuca alternifolia and M. linariifolia by monoterpenoid comparison. Photochemistry, 29, 3529-3533.

Southwell, I.A., Freeman, S. and Rubel, D. (1997) Skin irritancy of tea tree oil. J. Essent. Oil Res., 9, 47-52.

Southwell, I.A. and Tucker, D.J. (1991) NSW Agriculture, University of New England. Unpublished results.

Southwell, I.A., Stiff, I.A. and Brophy, J.J. (1992) Terpinolene varieties of Melaleuca. J. Essent. Oil Res., 4, 363-367.

Southwell, I.A., Maddox, C.D.A. and Zalucki, M.P. (1995) Metabolism of 1,8-cineole in tea tree (Melaleuca alternifolia and M. linariifolia) by pyrgo beetle (Paropsisterna tigrina) J. Chem. Ecol., 21, 439-453.

Standards Association of Australia. (1967) Oil of Melaleuca alternifolia; Standards Australia: Sydney, K175.

Standards Association of Australia. (1985) Essential Oils—Oil of Melaleuca, Terpinen-4-ol Type; Standards Association of Australia: North Sydney, AS 2782-1985.

Standards Australia. (1997) Oil of Melaleuca, terpinen-4-ol type (Tea Tree oil) Standards Australia: Sydney, AS 2782-1997.

Stevens, R. (1996) Editorial. Flav. Frag. J., 11, 1.

Stiff, I.A. (1996) Ph.D. Thesis. Macquarie University, Sydney.

Swords, G. and Hunter, G.L.K. (1978) Composition of Australian Tea Tree Oil (Melaleuca alternifolia). J. Agric. Food Chem., 26, 734-737.

Taskinen, J. (1974) Composition of the essential oil of sweet marjoram obtained by distillation with steam and by extraction and distillation with alcohol-water mixture. Acta Chem. Scand., B28, 1121.

Tisserand, R. and Balacs, T. (1995) Essential Oil Safety, Churchill Livingston, Edinburgh, p. 186.

Verghese, J. (1966) Terpinen-4-ol, Perfumery and Essential Oil Record, 694-498.

Williams, L.R. and Lusunzi, I. (1994) Essential oil from Melaleuca dissitiflora: a potential source of high quality tea tree oil. Indust. Crops Prod., 2, 211-217. Wong, V. (1997) Supercritical Fluid Extraction (SFE) of Monoterpenes from Australian Tea Tree Leaves (Melaleuca alternifolia). B. Appl. Sci. (Hons) Thesis. University of Western Sydney, Hawkesbury, Richmond.

Wrigley, J.W. and Fagg, M. (1993) Bottlebrushes, Paperbarks and Tea Trees and all other Plants in the Leptospermum Alliance. Angus and Robertson, Sydney pp. 5-17.

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