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Biologically Important Eremophilane Sesquiterpenes from Alaska Cedar Heartwood Essential Oil and Their Semi-Synthetic Derivatives
Department of Chemistry, College of Science, United Arab Emirates University, Al-Ain, P.O. Box 17551, United Arab Emirates
Department of Forest Products and Engineering, College of Forestry, Oregon State University, Corvallis, Oregon 97333, USA
National School of Biological Sciences, National Polytechnic Institute, Carpio Y Plan De Ayala, Mexico City 11340 D.F. Mexico
* Author to whom correspondence should be addressed.
Received: 11 April 2011; in revised form: 28 May 2011 / Accepted: 30 May 2011 / Published: 8 June 2011
Abstract: The essential oil of Alaska cedar heartwood is known to contain compounds which contribute to the remarkable durability of this species. While previous research has identified several compounds, a complete description of this oil has not been undertaken. In this research a profile of the oil is given in which the major components are identified by GC, isolation and spectroscopic techniques. The major components of the steam distilled essential oil were identified as nootkatin, nootkatone, valencene, nootaktene, carvacrol, methyl carvacrol, nootkatol (2), and eremophil-1(10),11-dien-13-ol (3). The last two compounds were isolated for the first time from Alaska cedar in this research. The absolute stereochemistry at C-2 of nootkatol was shown to have the (S) configuration using the Mosher ester method. Assignment of stereochemistry for valencene-13-ol (3) was established by synthesis from valencene (6). Finally, two related sesquiterpenoids were synthesized from nootkatone and valencene. These sesquiterpenoids were nootkatone-1,10-11,12-diepoxide (5) and valencene-13-aldehyde (4), respectively.
Keywords: eremophilane sesquiterpenes; nootkatol; valencene-13-ol; stereochemistry; Chamaecyparis nootkatensis
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Khasawneh, M.A.; Xiong, Y.; Peralta-Cruz, J.; Karchesy, J.J. Biologically Important Eremophilane Sesquiterpenes from Alaska Cedar Heartwood Essential Oil and Their Semi-Synthetic Derivatives. Molecules 2011, 16, 4775-4785.
Khasawneh MA, Xiong Y, Peralta-Cruz J, Karchesy JJ. Biologically Important Eremophilane Sesquiterpenes from Alaska Cedar Heartwood Essential Oil and Their Semi-Synthetic Derivatives. Molecules. 2011; 16(6):4775-4785.
Khasawneh, Mohammad A.; Xiong, Yeping; Peralta-Cruz, Javier; Karchesy, Joe J. 2011. "Biologically Important Eremophilane Sesquiterpenes from Alaska Cedar Heartwood Essential Oil and Their Semi-Synthetic Derivatives." Molecules 16, no. 6: 4775-4785.