Essential oil composition of Dendropanax gonatopodus from Monteverde, Costa Rica. An ab initio examination of aromadendrane sesquiterpenoids

Natural Product Communications

Volumn 3, Issue 9, 2008, Pages 1557-1561

  Setzer, William N ^a  

^a University of Alabama in Huntsville   (United States)

Author keywords

Ab initio molecular orbital theory; Aromadendrane sesquiterpenoid; Dendropanax gonatopodus; Density functional theory; Essential oil composition

Indexed keywords

2 HEXENAL; AROMADENDRENE; CARYOPHYLLENE; COPAENE; DELTA CADINENE; DENDROPANAX GONATOPODUS EXTRACT; ESSENTIAL OIL; PLANT EXTRACT; SESQUITERPENOID; SPATHULENOL; TERPINOLENE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ANALYTIC METHOD; ARTICLE; CHEMICAL COMPOSITION; COSTA RICA; DENDROPANAX GONATOPODUS; DENSITY; DISTILLATION; ENTROPY; MASS FRAGMENTOGRAPHY; MEDICINAL PLANT; NONHUMAN; PLANT LEAF;

DENDROPANAX;

EID: 68149110647     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x0800300932     Document Type: Article

References (49)

1. nd Ed. Cambridge University Press, UK, 51.
2. Gongyan H, Weihua Z, Ruihua H. (1998) Separation and determination of chemical constituents in the volatile oil of three traditional Chinese crude drugs. Journal of Pharmaceutical and Biomedical Analysis, 17, 1423-1426. (Pubitemid 29027749)
3. Garneau FX, Collin G, Gagnon H, Jean FI, Strobl H, Pichette A. (2006) The essential oil composition of devil's club, Oplopanax horridus J.E. Smith Miq. Flavour and Fragrance Journal, 21, 792-794.
4. Muselli A, Hoi TM, Cu LD, Moi LD, Bessiere JM, Bighelli A, Casanova J. (1999) Composition of the essential oil of Acanthopanax trifoliatus (L.) Merr. (Araliaceae) from Vietnam. Flavour and Fragrance Journal, 14, 41-44. (Pubitemid 29117023)
5. (a) Pino JA, Marbot R, Payo A, Chao D, Herrera P, Marti MP. (2005) Leaf oil of Dendropanax arboreus L. from Cuba. Journal of Essential Oil Research, 17, 547-548;
6. (b) Werka JS, Boehme AK, Setzer WN. (2007) Biological activities of essential oils from Monteverde, Costa Rica. Natural Product Communications, 2, 1215-1219.
7. Richter R, Basar S, Koch A, König WA. (2005) Three sesquiterpene hydrocarbons from the roots of Panax ginseng C.A. Meyer (Araliaceae). Phytochemistry, 66, 2708-2713. (Pubitemid 41727655)
8. (a) Swords G, Hunter GLK. (1978) Composition of Australian tea tree oil (Melaleuca alternifolia). Journal of Agricultural and Food Chemistry, 26, 734-737;
9. (b) Brophy JJ, Lassak EV. (1991) Steam volatile leaf oils of some Western Australian Eucalyptus species. Flavour and Fragrance Journal, 6, 265-269;
10. (c) Lassak EV, Brophy JJ. (2004) Steam volatile leaf oils of some Western Australian species of the family Myrtaceae. Flavour and Fragrance Journal, 19, 12-16;
11. (d) Cole RA, Bansal A, Moriarity DM, Haber WA, Setzer WN. (2007) Chemical composition and cytotoxic activity of the leaf essential oil of Eugenia zuchowskiae from Monteverde, Costa Rica. Journal of Natural Medicines, 61, 414-417. (Pubitemid 47441013)
12. (a) Becke AD. (1993) Density-functional thermochemistry. III. The role of exact exchange. Journal of Chemical Physics, 98, 5648-5652;
13. (b) Lee C, Yang W, Parr RG. (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Physical Review B, 37, 785-789.
14. Hehre WJ, Radom L, Schleyer PvR. (1986) Ab initio Molecular Orbital Theory. Wiley, New York.
15. Schreiner PR, Fokin AA, Pascal RA, de Meijere A. (2006) Many density functional theory approaches fail to give reliable large hydrocarbon isomer energy differences. Organic Letters, 8, 3635-3638.
16. El-Ghorab A, Fadel HM, El-Massry KF. (2002) The Egyptian Eucalyptus camaldulensis var. brevirostris: chemical compositions of the fruit volatile oil and antioxidant activity. Flavour and Fragrance Journal, 17, 306-312. (Pubitemid 34752847)
17. Cheng SS, Lin HY, Chang ST. (2005) Chemical composition and antifungal activity of essential oils from different tissues of Japanese cedar (Cryptomeria japonica). Journal of Agricultural and Food Chemistry, 53, 614-619.
18. Weyerstahl P, Marschall H, Weirauch M, Thefeld K, Surburg H. (1998) Constituents of commercial Labdanum oil. Flavour and Fragrance Journal, 13, 295-318.
19. Moreno-Dorado FJ, Lamers YMAW, Mironov G, Wijnberg JBPA, de Groot A. (2003) Chemistry of (+)-aromadendrene. Part 6: Rearrangement reactions of ledene, isoledene and their epoxides. Tetrahedron, 59, 7743-7750. (Pubitemid 37107453)
20. Polovinka MP, Shal'ko AA, Korchagina DV, Gatilov YV, Shcherbukhin VV, Barkhash VA. (1996) Rearrangements of ledene and aromadendrene in superacids. Tetrahedron Letters, 37, 2631-2632.
21. (a) Bignell CM, Dunlop PJ, Brophy JJ, Fookes CJR. (1997) Volatile leaf oils of some south-western and southern Australian species of the genus Eucalyptus (Series I). Part XIV. Subgenus Monocalyptus. Flavour and Fragrance Journal, 12, 177-183;
22. (b) Bignell CM, Dunlop PJ, Brophy JJ. (1997) Volatile leaf oils of some south-western and southern Australian species of the genus Eucalyptus (Series I). Part XVIII. A. Subgenus Monocalyptus. B. Subgenus Symphyomyrtus: (i) section Guilfoyleanae; (ii) section Bisectaria, series Accedentes, series Occidentales, series Levispermae, series Loxophlebae, series Macrocarpae, series Orbifoliae, series Calycogonae; (iii) section Dumaria, series Incrassatae, and series Ovulares. Flavour and Fragrance Journal, 12, 423-432.
23. Setzer WN. (2008) Germacrene D cyclization: An ab initio investigation. International Journal of Molecular Sciences, 9, 89-97.
24. Setzer WN. (2008) Ab initio analysis of the Cope rearrangement of germacrane sesquiterpenoids. Journal of Molecular Modeling, 14, 335-342.
25. (a) Berenbaum MR. (1995) The chemistry of defense: Theory and practice. Proceedings of the National Academy of Sciences of the United States of America, 92, 2-8;
26. (b) Gershenzon J, Dudareva N. (2007) The function of terpene natural products in the natural world. Nature Chemical Biology, 3, 408-414; (Pubitemid 46956324)
27. (c) Hartmann T. (2007) From waste products to ecochemicals: Fifty years research of plant secondary metabolism. Phytochemistry, 68, 2831-2846;
28. (d) Macías FA, Calindo JLG, Galindo JCG. (2007) Evolution and current status of ecological phytochemistry. Phytochemistry, 68, 2917-2936. (Pubitemid 350180960)
29. Wittstock U, Gershenzon J. (2002) Constitutive plant toxins and their role in defense against herbivores and pathogens. Current Opinion in Plant Biology, 5, 300-307. (Pubitemid 34695967)
30. (a) Paré PW, Tumlinson JH. (1996) Plant volatile signals in response to herbivore feeding. Florida Entomologist, 79, 93-103;
31. (b) Pichersky E, Gershenzon J. (2002) The formation and function of plant volatiles: perfumes for pollinator attraction and defense. Current Opinion in Plant Biology, 5, 237-243; (Pubitemid 34452071)
32. (c) Maffei ME, Mithöfer A, Boland W. (2007) Insects feeding on plants: Rapid signals and responses preceding the induction of phytochemical release. Phytochemistry, 68, 2946-2959. (Pubitemid 350180944)
33. (a) Vallejo I, Rebordinos L, Collado IG, Fernández JMC. (2001) Differential behaviour of mycelial growth of several Botrytis cinerea strains on either patchoulol- or globulol-amended media. Journal of Phytopathology, 149, 113-118; (Pubitemid 32235380)
34. (b) Aleu J, Hanson JR, Galán RH, Collado IG. (2001) Biotransformation of the fungistatic sesquiterpenoids patchoulol, ginsenol, cedrol and globulol by Botrytis cinerea. Journal of Molecular Catalysis B: Enzymatic, 11, 329-334; (Pubitemid 32114218)
35. (c) Terry LA, Joyce DC, Khambay PS. (2003) Antifungal compounds in Geraldton waxflower tissues. Australasian Plant Pathology, 32, 411-420.
36. Bichlmaier I, Kurkela M, Siiskonen A, Finel M, Yli-Kauhaluoma J. (2007) Eudismic analysis of tricyclic sesquiterpenoid alcohols: Lead structures for the design of potent inhibitors of the human UDP-glucuronosyltransferase 2B7. Bioorganic Chemistry, 35, 386-400.
37. Kim YS, Shin DH. (2004) Volatile constituents from the leaves of Callicarpa japonica Thunb. and their actibacterial activities. Journal of Agricultural and Food Chemistry, 52, 781-787.
38. (a) Tanaka Y, Kikuzaki H, Nakatani N. (2003) Antibacterial activity of essential oils against pathogens bacteria in upper airway respiratory tract. Koryo, Terupen oyobi Seiyu Kagaku ni kansuru Toronkai Koen Yoshishu, 47, 303-305.
39. (b) Tanaka Y. (2005) Antibacterial activity of volatile compounds against pathogens bacteria in upper airway respiratory tract. Koryo, 225, 135-142.
40. Scher JM, Speakman JB, Zapp J, Becker H. (2004) Bioactivity guided isolation of antifungal compounds from the liverwort Bazzania trilobata (L.) S.F. Gray. Phytochemistry, 65, 2583-2588.
41. Miyazawa M, Watanabe H, Umemoto K, Kameoka H. (1998) Inhibition of acetylcholinesterase activity by essential oils of Mentha species. Journal of Agricultural and Food Chemistry, 46, 3431-3434.
42. Jäger AK, Almqvist JP, Vangsøe SAK, Stafford GI, Adsersen A, Van Staden J. (2007) Compounds from Mentha aquatica with affinity to the GABA-benzodiazepine receptor. South African Journal of Botany, 73, 518-521.
43. Matos MFC, Leite LISP, Brustolim D, de Sequeira JM, Carollo CA, Hellmann AR, Pereira NFG, da Silva DB. (2006) Antineoplastic activity of selected constituents of Duguetia glabriuscula. Fitoterapia, 77, 227-229.
44. Gwaltney SL, Shea KJ. (1996) Bridged to fused ring interchange. The total synthesis of (±)-ledol. Tetrahedron Letters, 37, 949-952.
45. Ulubelen A, Topcu G, Eriş C, Sönmez U, Kartal M, Kurucu S, Bozok-Johansson C. (1994) Terpenoids from Salvia sclarea. Phytochemistry, 36, 971-974.
46. (a) Pacciaroni AdV, Mongelli E, Espinar LA, Romano A, Ciccia G, Silva GL. (2000) Bioactive constituents of Conyza albida. Planta Medica, 66, 720-723;
47. (b) Fukuda M, Ohkoshi E, Makino M, Fujimoto Y. (2006) Studies on the constituents of the leaves of Baccharis dracunculifolia (Asteraceae) and their cytotoxic activity. Chemical and Pharmaceutical Bulletin, 54, 1465-1468.
48. Adams RP. (2007) Identification of Essential Oil Components byGas Chromatography / Mass Spectrometry, 4th Ed. Allured Publishing, Carol Stream, Illinois.
49. SPARTAN '06 for Windows (2006) Wavefunction, Inc., Irvine, California.