Comparison of the formation of peppery and woody sesquiterpenes derived from α-guaiene and α-bulnesene under aerial oxidative conditions

Journal of Agricultural and Food Chemistry

Volumn 63, Issue 7, 2015, Pages 1932-1938

  Huang, An Cheng ^a   Sefton, Mark A ^a   Taylor, Dennis K ^a  

^a UNIVERSITY OF ADELAIDE   (Australia)

Author keywords

autoxidation; bulnesene; bulnesone; guaiene; rotundone

Indexed keywords

AUTOXIDATION; BULNESENE; BULNESONE; GUAIENE; ROTUNDONE;

OXIDATION;

ALPHA-BULNESENE; AZULENE DERIVATIVE; FLAVORING AGENT; GUAIENE; SESQUITERPENE;

ANALYSIS; CHEMISTRY; COMPARATIVE STUDY; ODOR; OXIDATION REDUCTION REACTION;

AZULENES; FLAVORING AGENTS; ODORS; OXIDATION-REDUCTION; SESQUITERPENES; SESQUITERPENES, GUAIANE;

EID: 84923330930     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf505537s     Document Type: Article

References (19)

1. Ansari, H.; Curtis, A. Sesquiterpenes in the perfumery industry J. Soc. Cosmet. Chem. 1974, 25, 203-231
2. Wood, C.; Siebert, T.; Parker, M.; Capone, D.; Elsey, G.; Pollnitz, A.; Eggers, M.; Meier, M.; Vössing, T.; Widder, S. From wine to pepper: rotundone, an obscure sesquiterpene, is a potent spicy aroma compound J. Agric. Food Chem. 2008, 56 (10) 3738-3744
3. Huang, A.-C.; Burrett, S.; Sefton, M.; Taylor, D. Production of the Pepper Aroma Compound, (-)-Rotundone, by Aerial Oxidation of α-Guaiene J. Agric. Food Chem. 2014, 62 (44) 10809-10815
4. Schilling, B.; Granier, T.; Locher, E. Preparation of 1-hydroxyoctahydroazulenes as fragrances. WO2012001018A1, 2012.
5. Huang, A.-C.; Sefton, M.; Sumby, C.; Tiekink, E. T. R.; Taylor, D. Mechanistic Studies on the Autoxidation of a-Guaiene: The Structural Diversity of the Sesquiterpenoid Downstream Products J. Nat. Prod. 2014, 10.1021/np500819f
6. Kumeta, Y.; Ito, M. Characterization of δ-guaiene synthases from cultured cells of Aquilaria, responsible for the formation of the sesquiterpenes in agarwood Plant Physiol. 2010, 154 (4) 1998-2007
7. Kapadia, V. H.; Naik, V. G.; Wadia, M. S.; Dev, S. Sesquiterpenoids from the essential oil of cyperus rotundus Tetrahedron Lett. 1967, 8 (47) 4661-4667
8. Liu, X. C.; Zhou, L.; Liu, Z. L., Identification of Insecticidal Constituents from the Essential Oil of Valeriana jatamansi Jones against Liposcelis bostrychophila Badonnel. J. Chem. 2013, 2013.
9. Prakash, O.; Joshi, S.; Shukla, A. K.; Pant, A. K. Sesquiterpenoid Rich Essential Oil from the Leaves of Pogostemon patchouli Pellet Grown Organically Under Tarai Conditions J. Essent. Oil Bear. Plants 2007, 10 (2) 157-161
10. Winck, C. R.; Cardoso, C. A.; Jeller, A. H.; Ré-Poppi, N.; Coelho, R. M.; Schleder, E. J. D. Identification of the volatile compounds of leaf oil of Anacardium humile (Anacardiaceae) J. Essent. Oil Res. 2010, 22 (1) 11-12
11. Verma, R. S.; Verma, R. K.; Padalia, R. C.; Chauhan, A.; Singh, A.; Singh, H. P. Chemical Diversity in the Essential Oil of Indian Valerian (Valeriana jatamansiJones) Chem. Biodiversity 2011, 8 (10) 1921-1929
12. Armarego, W. L. F.; Chai, C. L. L. Purification of Laboratory Chemicals, 5 th ed.; Elsevier Inc.: New York, 2003.
13. Gupta, A. S.; Dev, S. Chromatography of organic compounds. I. Thin-layer chromatography of olefins J. Chromatogr. 1963, 12 (2) 189-95
14. Siebert, T.; Wood, C.; Elsey, G.; Pollnitz, A. Determination of rotundone, the pepper aroma impact compound, in grapes and wine J. Agric. Food Chem. 2008, 56 (10) 3745-3748
15. Huang, A.-C.; Sumby, C.; Tiekink, E. R. T.; Taylor, D. Synthesis of Guaia-4(5)-en-11-ol, Guaia-5(6)-en-11-ol, Aciphyllene, 1-epi-Melicodenone C and E and other Guaiane-type Sesquiterpenoids via the Diastereoselective Epoxidation of Guaiol J. Nat. Prod. 2014, 77 (11) 2522-2536
16. 1] farnesyl diphosphate catalyzed by recombinant patchoulol synthase J. Am. Chem. Soc. 2010, 132, 2998-3008
17. Ishihara, M.; Tsuneya, T.; Shiga, M.; Uneyama, K. Three sesquiterpenes from agarwood Phytochemistry 1991, 30 (2) 563-6
18. 2. High intramolecular selectivity Synlett 2007, 1869-1872
19. Ishihara, M.; Masatsugu, Y.; Uneyama, K. Preparation of (-)-guaia-1(10),11-dien-15,2-olide and (-)-2α-hydroxyguaia-1(10),11-dien-15-oic acid, fragrant sesquiterpenes in agarwood (Aquilaria agallocha Roxb.) Tetrahedron 1992, 48 (47) 10265-10276