Comparative chemical analysis of the essential oil constituents in the bark, heartwood and fruits of Cryptocarya massoy (Oken) Kosterm. (Lauraceae) from Papua New Guinea

Molecules

Volumn 12, Issue 2, 2007, Pages 149-154

  Rali, Topul ^a   Wossa, Stewart W ^b   Leach, David N ^c  

^a UNIVERSITY OF PAPUA NEW GUINEA   (Papua New Guinea)

^b University of Goroka   (Papua New Guinea)

^c SOUTHERN CROSS UNIVERSITY   (Australia)

Author keywords

, unsaturated lactone; 5,6 dihydro 6 heptyl 2H pyran 2 one (C 12 massoia lactones); 5,6 dihydro 6 pentyl 2H pyran 2 one (C 10 massoia lactone); Benzyl benzoate; Cryptocarya massoy; Essential oil analysis; Lauraceae; Massoia lactones

Indexed keywords

ESSENTIAL OIL; VEGETABLE OIL;

ANGIOSPERM; ARTICLE; BARK; CHEMISTRY; CRYPTOCARYA; FRUIT; PAPUA NEW GUINEA;

CRYPTOCARYA; FRUIT; LAURACEAE; OILS, VOLATILE; PAPUA NEW GUINEA; PLANT BARK; PLANT OILS;

EID: 33847723387     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/12020149     Document Type: Article

References (31)

1. Hutchinson, J. Evolution and Phylogeny of Flowering Plants; Academic Press: London, 1969; p. 28
2. Rohwer, J.A. Lauraceae. In: Kubitzki, K., Rohwer, J.A. and Bittrich, V. Eds. The Families and Genera of Vascular Plants. Vol II. Flowering Plants - Dicotyledons; Springer-Verlag: Berlin, 1993; pp. 366-391.
3. Gottlieb, O. R. Chemosystematics of the Lauraceae. Phytochemistry 1972, 11, 1537-1570.
4. Zschocke, S.; van Staden, J. Cryptocarya species - substitute plants for Ocotea bullata? A pharmacological investigation in terms of cyclooxygenase-1 and -2 inhibition. J. Ethnopharmacol. 2000, 71, 473-478.
5. Drewers, S.E.; Horn, M.H.; Mavis, S. Cryptocarya liebertiana and Ocotea bullata - Their phytochemical relationship. Phytochemistry 1997, 44, 437-440.
6. Hawariah, A.L.P.; Stanslas, J.; Laily, D. Non-steroid receptor mediated antiproliferative activity of styrylpyrone derivative in human breast cancer cell lines. Anticancer Res. 1998, 18, 1739-1744.
7. Hawariah, A.L.P.; Munawar, M.; Laily, D. Antifertility effect of Goniothalamin: A styrylpyrone isolated from Goniothalamus tapis Miqo. Asia Pacific J. Pharmacol. 1994, 9, 273-277.
8. Hawariah, A.L.P.; Stanslas, J. In vitro response of human breast cancer cell lines to the growth-inhibitory effects of styrylpyrone derivative (SPD) and assessment of its antiestrogenicity. Anticancer Res. 1998, 18, 4383-4386.
9. Collins, D.J.; Culvenor, C.C.J.; Lamberton, J.A.; Loder, J.W.; Price, J.R. Plants for medicine: a chemical and pharmacological survey of plants of the Australian region. CSIRO Australia, 1990.
10. Hlubucek, J.R.; Robertson, A.V. (+)-(5S)-δ-lactone of 5-hydroxy-7-phenylhepta-2,6-dienoic acid, a natural product from Cryptocarya caloneura (Scheff.) Kostermans. Aust. J. Chem. 1967, 20, 2199-2206.
11. Abe, S. Massoy oil. J. Chem. Soc. Japan 1937, 58, 246-251.
12. Cavill, G.W.K.; Clark, D.V.; Whitfield, F.B. Insect Venom, Attractants and Repellents. XI. Massoialactone from two species of Formicine ants, and some observations on constituents of the bark oil of Cryptocarya massoia. Aust. J. Chem. 1968, 21, 2819-2823.
13. Lloyd, H.A.; Schmuff, N.R.; Hefetz, A. Chemistry of the male mandibular gland secretion of the carpenter ant, Camponotus thoracicus fellah emery. Comp. Biochem. Physiol. Part B. Biochem. Mol. Biol. 1984, 78, 687-689.
14. Fleisher, Z.; Fleisher, A. Volatiles of Achillea fragrantissima (Forssk.) Sch. Bip. Aromatic Plants of the Holy Land and the Sinai. Part XI. J. Essent. Oil Res. 1993, 5, 211-214.
15. Brophy, J.J.; Goldsack, R.J.; Forster, P.I. The Leaf essential oil of Cryptocarya cunninghamii Meissner (Lauraceae). J. Essent. Oil Res., 1998, 10, 73-75.
16. You, Z-W.; Wu, Y-Y.; Qing, F-L. Synthesis of gem-difluoromethylenated massoialactone by ring-closing metathesis. Tetrahedron Lett. 2004, 45, 9479-9481.
17. Fournier, L.; Korcienski, P.; Pons, J-M. The β-lactone route to α,β-unsaturated δ-lactones. Total syntheses of (±)-goniothalamin and (-)-massoialactone. Tetrahedron 2004, 60, 1659-1663.
18. Gupta, P.; Naidu, S.K.; Kumar, P. A practical enantioselective syntheses of massoialactone via hydrolytic kinetic resolution. Tetrahedron Lett. 2004, 45, 849-851.
19. Ramachandran, P.V.; Reddy, M.V.R.; Brown, H.C. Asymmetric synthesis of goniothalamin, hexadecanolide, massoialactone and parasorbic acid via sequential allylboration-esterification ring-closing metathesis reaction. Tetrahedron Lett. 2000, 41, 583-586.
20. Pais, G.C.G.; Fernandes, R.A.; Kumar. P. Asymmetric synthesis of (S)-Massoialactone. Tetrahedron 1999, 55, 13445-13450.
21. Romeyke, Y.; Keller, M.; Grabley, S.; Hammann, P. Secondary metabolites by chemical screening-13- Enantioselective synthesis of δ-lactones from streptenola, a chiral building block from Streptomyces sp. Tetrahedron 1991, 47, 3335-3346.
22. Pohmakotr, M.; Jarupan, P. A new syntheses of α,β-unsaturated γ- and δ-lactones via intramolecular acylation of α-sulfinylcarbanion. Tetrahedron Lett. 1985, 26, 2253-2256.
23. Gil, B.; Christopher, D. Process for the biotechnological production of Delta-decalactone and Delta-dodecalactone. European Patent EP0899342, 1999.
24. D'Arrigo, P.; Fuganti, C.; Fantoni, G.P.; Servi, S. Extractive biocatalysis: A powerful tool in selectivity control in yeast biotransformation. Tetrahedron 1998, 54, 15017-15026.
25. Fuganti, C.; Fantoni, G.P.; Sarra, A.; Servi, S. Stereochemistry of Baker's yeast mediated conversion of α,β-unsaturated δ-lactones in the goniothalamin series. Tetrahedron: Asymmetr. 1994, 5, 1135-1138.
26. Shinobu, G.; Rumi, K.; Tsuyoshi, K. Process for the production of the δ-decalactone. Eur. Pat. EP0822259, 1998.
27. Cardillo, R.; Fugati, C.; Babeni, M.; Allegro, G. Process for the preparation of saturated delta lactones by biohydrogenation of the corresponding unsaturated compounds by microorganisms. European Patent EP0577463, 1994.
28. Garnero, J.; Joulain, D. Massoia essential oil. IXth International Congress of Essential Oils, Essential Oil Technical Paper Book 3, 1983; pp. 184-193.
29. Joulain, D.; Konig, W.A. The Atlas of Spectral Data of Sesquiterpene Hydrocarbons; E.B. Verlag: Hamburg, Germany, 1998.
30. Adams, R.P. Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry; Allured Pub. Corp.: Carol Stream, IL, USA, 1995.
31. Swigar, A.A.; Silverstein, R.M. Monoterpenes; Aldrich: Milwaukee, USA, 1981.