A phytochemical investigation of the crude chloroform bark extract of Neolitsea dealbata from Paluma, north Queensland, Australia, revealed the two common triterpenoids, taraxerone and taraxerol, as well as three furanogermacranolide sesquiterpenoids, linderadine, linderalactone, and pseudoneolinderane. These compounds are reported for the first time from this plant. An ab initio investigation (DFT, B3LYP/6-31G* and post HF, MP2/6-31G**) of the Cope rearrangement of linderalactone has been carried out.
TakaokaD, TaniH, NozakiH, NakayamaM. (1993) Aciculatalactone, a new elemanolide sesquiterpenoid from Neolitsea aciculata Koidz. Chemistry Letters, 1467–1468;
2.
ChangFR, HsiehTJ, HuangTL, ChenCY, KuoRY, ChangYC, ChiuHF, WuYC. (2002) Cytotoxic constituents of the stem bark of Neolitsea acuminatissima. Journal of Natural Products, 65, 255–258;
3.
SharmaMC, OhiraT, YatagaiM. (1993) Sericeol, a cycloartane triterpene from Neolitsea sericea. Phytochemistry, 33, 721–722;
4.
SharmaMC, OhiraT, YatagaiM. (1994) Lanostane triterpenes from the bark of Neolitsea sericea. Phytochemistry, 37, 201–203;
5.
YanoK, AkihisaT, TamuraT, MatsumotoT. (1992) Four 4α-methylsterols and triterpene alcohols from Neolitsea aciculata. Phytochemistry, 31, 2093–2098;
6.
BrophyJJ, GoldsackRJ, FookesCJR, ForsterPI. (2002) The leaf oils of the Australian Neolitsea (Lauraceae). Journal of Essential Oil Research, 14, 191–195.
ZhangCF, SunQS, WangZT, ChouGX. (2001) Studies on constituents of the leaves of Lindera aggregata (Sims) Kosterm. China Journal of Chinese Materia Medica, 26, 765–767;
13.
WataruK, ToshioM, MitsuakiS, KaoruU, TsutomuW, HiroshiN. (2002) Prolyl endopeptidase inhibitors from the roots of Lindera strychnifolia F. Vill. Biological & Pharmaceutical Bulletin, 25, 1049–1052.
14.
TakedaK, HoribeI, ToraokaM, MinatoH. (1969) Components of the root of Lindera strychnifolia Vill. Part XV. Absolute configuration of linderalactone, linderane, and isolinderalactone and its derivatives. Journal of the Chemical Society, C, 1491–1495;
15.
TakedaK, HoribeI, MinatoH. (1970) Cope rearrangement of some germacrane-type furan sesquiterpenes. Part I. Journal of the Chemical Society, C, 1142–1147;
16.
TakedaK, HoribeI, MinatoH. (1973) Cope rearrangement of some germacrane-type furan sesquiterpenes. Part IV. Preparation of some cyclodeca-cis-trans-diene derivatives and their Cope rearrangements. Journal of the Chemical Society, Perkin Transactions I, 2212–2220.
17.
GopalanA, MagnusP. (1980) Synthesis of (±)-linderalactone, (±)-isolinderalactone, and (±)-neolinderalactone. Journal of the American Chemical Society, 102, 1756–1757;
18.
GopalanA, MagnusP. (1984) Studies on terpenes, 8. Total synthesis of (±)-linderalactone, (±)-isolinderalactone, and (±)-neolinderalactone, germacrane furanosesquiterpenes. Journal of Organic Chemistry, 49, 2317–2321.
19.
EssDH, HoukKN. (2005) Activation energies of pericyclic reactions: Performance of DFT, MP2, and CBS-QB3 methods for the prediction of activation barriers and reaction energetics of 1,3-dipolar cycloadditions, and revised activation enthalpies for a standard set of hydrocarbon pericyclic reactions. Journal of Physical Chemistry, A, 109, 9542–9553.
20.
WoodrichMD, CorminboeufC, SchreinerPR, FokinAA, SchleyerPvR. (2007) How accurate are DFT treatments of organic energies?Organic Letters, 9, 1851–1854;
21.
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.
22.
SetzerMC, SetzerWN, JackesBR, GentryGA, MoriarityDM. (2001) The medicinal value of tropical rainforest plants from Paluma, north Queensland, Australia. Pharmaceutical Biology, 39, 67–78.
23.
BatesRB, JacobsenNE, SetzerWN, StessmanCC. (1998) NMR assignments and conformation of taraxerenes. Magnetic Resonance in Chemistry, 36, 539–541.
SPARTAN ‘06 for Windows (2006) Wavefunction, Inc., Irvine, California.
26.
HalgrenTA. (1996) Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF 94. Journal of Computational Chemistry, 17, 490–519.
27.
HehreWJ, RadomL, SchleyerPvR. (1986) Ab initio Molecular Orbital Theory.Wiley, New York.
28.
BeckeAD. (1993) Density-functional thermochemistry. III. The role of exact exchange. Journal of Chemical Physics, 98, 5648–5652;
29.
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.
