The leaf essential oil of Dendropanax gonatopodus from Monteverde, Costa Rica, has been obtained by hydrodistillation and the chemical composition determined by GC-MS. The major components in the leaf oil were (E)-2-hexenal (16.9%), terpinolene (14.8%), δ-cadinene (13.5%), (E)-caryophyllene (9.9%), and α-copaene (7.3%). Minor amounts of the aromadendrane sesquiterpenoids aromadendrene (0.3%), alloaromadendrene (0.3%), spathulenol (0.6%) and globulol (0.6%) were also detected. An ab initio investigation of the aromadendrane sesquiterpenoids has been carried out using both density functional (B3LYP/6-31G*) and post Hartree-Fock (MP2/6-31G**) methods. The calculated relative energies of the aromadendranes belie their relative concentrations generally observed in essential oil compositions.
MabberleyDJ. (1997) The Plant-Book, 2nd Ed. Cambridge University Press, UK, 51.
2.
GongyanH, WeihuaZ, RuihuaH. (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.
3.
GarneauFX, CollinG, GagnonH, JeanFI, StroblH, PichetteA. (2006) The essential oil composition of devil's club, Oplopanax horridus J.E. Smith Miq. Flavour and Fragrance Journal, 21, 792–794.
4.
MuselliA, HoiTM, CuLD, MoiLD, BessiereJM, BighelliA, CasanovaJ. (1999) Composition of the essential oil of Acanthopanax trifoliatus (L.) Merr. (Araliaceae) from Vietnam. Flavour and Fragrance Journal, 14, 41–44.
5.
PinoJA, MarbotR, PayoA, ChaoD, HerreraP, MartiMP. (2005) Leaf oil of Dendropanax arboreus L. from Cuba. Journal of Essential Oil Research, 17, 547–548
6.
WerkaJS, BoehmeAK, SetzerWN. (2007) Biological activities of essential oils from Monteverde, Costa Rica. Natural Product Communications, 2, 1215–1219.
7.
RichterR, BasarS, KochA, KönigWA. (2005) Three sesquiterpene hydrocarbons from the roots of Panax ginseng C.A. Meyer (Araliaceae). Phytochemistry, 66, 2708–2713.
8.
SwordsG, HunterGLK. (1978) Composition of Australian tea tree oil (Melaleuca alternifolia). Journal of Agricultural and Food Chemistry, 26, 734–737
9.
BrophyJJ, LassakEV. (1991) Steam volatile leaf oils of some Western Australian Eucalyptus species. Flavour and Fragrance Journal, 6, 265–269
10.
LassakEV, BrophyJJ. (2004) Steam volatile leaf oils of some Western Australian species of the family Myrtaceae. Flavour and Fragrance Journal, 19, 12–16
11.
ColeRA, BansalA, MoriarityDM, HaberWA, SetzerWN. (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.
12.
BeckeAD. (1993) Density-functional thermochemistry. III. The role of exact exchange. Journal of Chemical Physics, 98, 5648–5652
13.
LeeC, YangW, ParrRG. (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Physical Review B, 37, 785–789.
14.
HehreWJ, RadomL, SchleyerPvR. (1986) Ab initio Molecular Orbital Theory.Wiley, New York.
15.
SchreinerPR, FokinAA, PascalRA, de MeijereA. (2006) Many density functional theory approaches fail to give reliable large hydrocarbon isomer energy differences. Organic Letters, 8, 3635–3638.
16.
El-GhorabA, FadelHM, El-MassryKF. (2002) The Egyptian Eucalyptus camaldulensis var. brevirostris: chemical compositions of the fruit volatile oil and antioxidant activity. Flavour and Fragrance Journal, 17, 306–312.
17.
ChengSS, LinHY, ChangST. (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.
WeyerstahlP, MarschallH, WeirauchM, ThefeldK, SurburgH. (1998) Constituents of commercial Labdanum oil. Flavour and Fragrance Journal, 13, 295–318.
19.
Moreno-DoradoFJ, LamersYMAW, MironovG, WijnbergJBPA, de GrootA. (2003) Chemistry of (+)-aromadendrene. Part 6: Rearrangement reactions of ledene, isoledene and their epoxides. Tetrahedron, 59, 7743–7750.
20.
PolovinkaMP, Shal'koAA, KorchaginaDV, GatilovYV, ShcherbukhinVV, BarkhashVA. (1996) Rearrangements of ledene and aromadendrene in superacids. Tetrahedron Letters, 37, 2631–2632.
21.
BignellCM, DunlopPJ, BrophyJJ, FookesCJR. (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.
BignellCM, DunlopPJ, BrophyJJ. (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.
SetzerWN. (2008) Germacrene D cyclization: An ab initio investigation. International Journal of Molecular Sciences, 9, 89–97.
24.
SetzerWN. (2008) Ab initio analysis of the Cope rearrangement of germacrane sesquiterpenoids. Journal of Molecular Modeling, 14, 335–342.
25.
BerenbaumMR. (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.
GershenzonJ, DudarevaN. (2007) The function of terpene natural products in the natural world. Nature Chemical Biology, 3, 408–414
27.
HartmannT. (2007) From waste products to ecochemicals: Fifty years research of plant secondary metabolism. Phytochemistry, 68, 2831–2846
28.
MacíasFA, CalindoJLG, GalindoJCG. (2007) Evolution and current status of ecological phytochemistry. Phytochemistry, 68, 2917–2936.
29.
WittstockU, GershenzonJ. (2002) Constitutive plant toxins and their role in defense against herbivores and pathogens. Current Opinion in Plant Biology, 5, 300–307.
30.
ParéPW, TumlinsonJH. (1996) Plant volatile signals in response to herbivore feeding. Florida Entomologist, 79, 93–103
31.
PicherskyE, GershenzonJ. (2002) The formation and function of plant volatiles: perfumes for pollinator attraction and defense. Current Opinion in Plant Biology, 5, 237–243
32.
MaffeiME, MithöferA, BolandW. (2007) Insects feeding on plants: Rapid signals and responses preceding the induction of phytochemical release. Phytochemistry, 68, 2946–2959.
33.
VallejoI, RebordinosL, ColladoIG, FernándezJMC. (2001) Differential behaviour of mycelial growth of several Botrytis cinerea strains on either patchoulol- or globulol-amended media. Journal of Phytopathology, 149, 113–118
34.
AleuJ, HansonJR, GalánRH, ColladoIG. (2001) Biotransformation of the fungistatic sesquiterpenoids patchoulol, ginsenol, cedrol and globulol by Botrytis cinerea. Journal of Molecular Catalysis B: Enzymatic, 11, 329–334
BichlmaierI, KurkelaM, SiiskonenA, FinelM, Yli-KauhaluomaJ. (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.
KimYS, ShinDH. (2004) Volatile constituents from the leaves of Callicarpa japonica Thunb. and their actibacterial activities. Journal of Agricultural and Food Chemistry, 52, 781–787.
38.
TanakaY, KikuzakiH, NakataniN. (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.
TanakaY. (2005) Antibacterial activity of volatile compounds against pathogens bacteria in upper airway respiratory tract. Koryo, 225, 135–142.
40.
ScherJM, SpeakmanJB, ZappJ, BeckerH. (2004) Bioactivity guided isolation of antifungal compounds from the liverwort Bazzania trilobata (L.) S.F. Gray. Phytochemistry, 65, 2583–2588.
41.
MiyazawaM, WatanabeH, UmemotoK, KameokaH. (1998) Inhibition of acetylcholinesterase activity by essential oils of Mentha species. Journal of Agricultural and Food Chemistry, 46, 3431–3434.
42.
JägerAK, AlmqvistJP, VangsøeSAK, StaffordGI, AdsersenA, Van StadenJ. (2007) Compounds from Mentha aquatica with affinity to the GABA-benzodiazepine receptor. South African Journal of Botany, 73, 518–521.
43.
MatosMFC, LeiteLISP, BrustolimD, de SequeiraJM, CarolloCA, HellmannAR, PereiraNFG, da SilvaDB. (2006) Antineoplastic activity of selected constituents of Duguetia glabriuscula. Fitoterapia, 77, 227–229.
44.
GwaltneySL, SheaKJ. (1996) Bridged to fused ring interchange. The total synthesis of (±)-ledol. Tetrahedron Letters, 37, 949–952.
45.
UlubelenA, TopcuG, ErişC, SönmezU, KartalM, KurucuS, Bozok-JohanssonC. (1994) Terpenoids from Salvia sclarea. Phytochemistry, 36, 971–974.
FukudaM, OhkoshiE, MakinoM, FujimotoY. (2006) Studies on the constituents of the leaves of Baccharis dracunculifolia (Asteraceae) and their cytotoxic activity. Chemical and Pharmaceutical Bulletin, 54, 1465–1468.
48.
AdamsRP. (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.
