Terpenoids from Neolitsea dealbata

Natural Product Communications

Volumn 3, Issue 2, 2008, Pages 129-132

  Wu, Xiujun ^a   Vogler, Bernhard ^a   Jackes, Betsy R ^b   Setzer, William N ^a  

^a UNIVERSITY OF ALABAMA IN HUNTSVILLE   (United States)

^b JAMES COOK UNIVERSITY   (Australia)

Author keywords

Ab initio; Cope rearrangement; Density functional theory; Furanosesquiterpenoids; Linderalactone; Neolitsea dealbata

Indexed keywords

LINDERALACTONE; PSEUDONEOLINDERANE; SESQUITERPENOID; TARAXEROL; TARAXERONE; TERPENOID DERIVATIVE; TRITERPENOID; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; AUSTRALIA; BARK; CONFORMATION; CRYSTAL STRUCTURE; DENSITY FUNCTIONAL THEORY; ENTHALPY; NEOLITSEA DEALBATA; NONHUMAN; PHYTOCHEMISTRY; PLANT;

NEOLITSEA DEALBATA;

EID: 77953964904     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x0800300204     Document Type: Article

References (29)

1. (a) Takaoka D, Tani H, Nozaki H, Nakayama M. (1993) Aciculatalactone, a new elemanolide sesquiterpenoid from Neolitsea aciculata Koidz. Chemistry Letters, 1467-1468;
2. (b) Chang FR, Hsieh TJ, Huang TL, Chen CY, Kuo RY, Chang YC, Chiu HF, Wu YC. (2002) Cytotoxic constituents of the stem bark of Neolitsea acuminatissima. Journal of Natural Products, 65, 255-258;
3. (c) Sharma MC, Ohira T, Yatagai M. (1993) Sericeol, a cycloartane triterpene from Neolitsea sericea. Phytochemistry, 33, 721-722;
4. (d) Sharma MC, Ohira T, Yatagai M. (1994) Lanostane triterpenes from the bark of Neolitsea sericea. Phytochemistry, 37, 201-203;
5. (e) Yano K, Akihisa T, Tamura T, Matsumoto T. (1992) Four 4α-methylsterols and triterpene alcohols from Neolitsea aciculata. Phytochemistry, 31, 2093-2098;
6. (f) Brophy JJ, Goldsack RJ, Fookes CJR, Forster PI. (2002) The leaf oils of the Australian Neolitsea (Lauraceae). Journal of Essential Oil Research, 14, 191-195.
7. (a) Li WS, Duh CY. (1993) Sesquiterpene lactones from Neolitsea villosa. Phytochemistry, 32, 1503-15071;
8. (b) Tori K, Ueyama M, Horibe I, Tamura Y, Takeda K. (1975) Carbon-13 NMR spectra of some furanosequiterpenes, major components of Lindera strychnifolia. Tetrahedron Letters, 51, 4583-4586;
9. (c) Chen KS, Chang FR. (1996) Two novel sesquiterpenes from Neolitsea parvigemma. Journal of Natural Products, 59, 704-706;
10. (d) Chen KS, Wu YC. (1999) Sesquiterpenoids from Neolitsea parvigemma: Isolation, oxidation products and antiplatelet actions. Tetrahedron, 55, 1353-1366;
11. (e) Padalia, RC, Chanotiya CS, Thakuri BC, Mathela CS. (2007) Germacranolide rich essential oil from Neolitsea pallens. Natural Product Communications, 2, 291-293.
12. (a) Zhang CF, Sun QS, Wang ZT, Chou GX. (2001) Studies on constituents of the leaves of Lindera aggregata (Sims) Kosterm. China Journal of Chinese Materia Medica, 26, 765-767;
13. (b) Wataru K, Toshio M, Mitsuaki S, Kaoru U, Tsutomu W, Hiroshi N. (2002) Prolyl endopeptidase inhibitors from the roots of Lindera strychnifolia F. Vill. Biological & Pharmaceutical Bulletin, 25, 1049-1052.
14. (a) Takeda K, Horibe I, Toraoka M, Minato H. (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. (b) Takeda K, Horibe I, Minato H. (1970) Cope rearrangement of some germacrane-type furan sesquiterpenes. Part I. Journal of the Chemical Society, C, 1142-1147;
16. (c) Takeda K, Horibe I, Minato H. (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. (a) Gopalan A, Magnus P. (1980) Synthesis of (±)-linderalactone, (±)-isolinderalactone, and (±)-neolinderalactone. Journal of the American Chemical Society, 102, 1756-1757;
18. (b) Gopalan A, Magnus P. (1984) Studies on terpenes, 8. Total synthesis of (±)-linderalactone, (±)-isolinderalactone, and (±)-neolinderalactone, germacrane furanosesquiterpenes. Journal of Organic Chemistry, 49, 2317-2321.
19. Ess DH, Houk KN. (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. (a) Woodrich MD, Corminboeuf C, Schreiner PR, Fokin AA, Schleyer PvR. (2007) How accurate are DFT treatments of organic energies? Organic Letters, 9, 1851-1854;
21. (b) 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.
22. Setzer MC, Setzer WN, Jackes BR, Gentry GA, Moriarity DM. (2001) The medicinal value of tropical rainforest plants from Paluma, north Queensland, Australia. Pharmaceutical Biology, 39, 67-78.
23. Bates RB, Jacobsen NE, Setzer WN, Stessman CC. (1998) NMR assignments and conformation of taraxerenes. Magnetic Resonance in Chemistry, 36, 539-541.
24. Parvez M, Gul W, Yousaf M, Iqbal Choudhary M, Atta-ur-Rahman, Riaz Khan M. (1999) Taraxerone. Acta Crystallographica, Section C, 55, 213-215.
25. SPARTAN '06 for Windows (2006) Wavefunction, Inc., Irvine, California.
26. Halgren TA. (1996) Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF 94. Journal of Computational Chemistry, 17, 490-519.
27. Hehre WJ, Radom L, Schleyer PvR. (1986) Ab initio Molecular Orbital Theory. Wiley, New York.
28. (a) Becke AD. (1993) Density-functional thermochemistry. III. The role of exact exchange. Journal of Chemical Physics, 98, 5648-5652;
29. (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.