Structure-Odor Relationship Study on Geraniol, Nerol, and Their Synthesized Oxygenated Derivatives

Journal of Agricultural and Food Chemistry

Volumn 66, Issue 10, 2018, Pages 2324-2333

  Elsharif, Shaimaa Awadain ^a   Buettner, Andrea ^a,b  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^b FRAUNHOFER INSTITUTE FOR PROCESS ENGINEERING AND PACKAGING IVV   (Germany)

Author keywords

8 hydroxygeraniol; gas chromatography olfactometry; mass spectrometry; odor threshold in air; retention indices

Indexed keywords

GAS CHROMATOGRAPHY; ISOMERS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PLANTS (BOTANY); SPECTROMETRY;

8-HYDROXYGERANIOL; GAS CHROMATOGRAPHY OLFACTOMETRIES; NUCLEAR MAGNETIC RESONANCE (NMR); ODOR THRESHOLDS; OXYGENATED COMPOUNDS; OXYGENATED DERIVATIVES; RETENTION INDEX; STRUCTURAL FEATURE;

MONOTERPENES;

FRAGRANCE; GERANIOL; OXYGEN; TERPENE;

CHEMICAL STRUCTURE; CHEMISTRY; ISOMERISM; MASS FRAGMENTOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLFACTOMETRY; SYNTHESIS;

GAS CHROMATOGRAPHY-MASS SPECTROMETRY; ISOMERISM; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; ODORANTS; OLFACTOMETRY; OXYGEN; TERPENES;

EID: 85043755225     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/acs.jafc.6b04534     Document Type: Article

References (49)

1. Semikolenov, V. A.; Ilyna, I. I.; Maksimovskaya, R. I. Linalool to geraniol/nerol isomerization catalyzed by (RO)3VO complexes: studies of kinetics and mechanism. J. Mol. Catal. A: Chem. 2003, 204-205, 201-210, 10.1016/S1381-1169(03)00299-1
2. Du, X.; Rouseff, R. Aroma active volatiles in four southern highbush blueberry cultivars determined by gas chromatography-olfactometry (GC-O) and gas chromatography-mass spectrometry (GC-MS). J. Agric. Food Chem. 2014, 62, 4537-4543, 10.1021/jf500315t
3. Smitha, G. R.; Rana, V. S. Variations in essential oil yield, geraniol and geranyl acetate contents in palmarosa (Cymbopogon martinii, Roxb. Wats. var. motia) influenced by inflorescence development. Ind. Crops Prod. 2015, 66, 150-160, 10.1016/j.indcrop.2014.12.062
4. Shoff, S. M.; Grummer, M.; Yatvin, M. B.; Elson, C. E. Concentration-dependent increase of murine P388 and B16 population doubling time by the acyclic monoterpene geraniol. Cancer Res. 1991, 51, 37-42
5. Yu, S. G.; Hildebrandt, L. A.; Elson, C. E. Geraniol, an inhibitor of mevalonate biosynthesis, suppresses the growth of hepatomas and melanomas transplanted to rats and mice. J. Nutr. 1995, 125, 2763-2767
6. Madan, K. A.; Devaki, T. Geraniol, a component of plant essential oils-a review of its pharmacological activities. Int. J. Pharm. Pharm. Sci. 2015, 7, 67-70
7. Lins, L.; Santos, I.; Santos de Melo, M.; Menezes, P.; Araújo, A.; Nunes, R.; Dos Santos, M.; Medeiros, I.; Ribeiro, E.; dos Santos, J. El efecto anticonvulsivo de geraniol y la inclusión de geraniol complejo: β-ciclodextrina. Bol. Latinoam. Caribe Plant. Med. Aromat. 2014, 13.
8. Kennedy, D. O.; Wake, G.; Savelev, S.; Tildesley, N. T. J.; Perry, E. K.; Wesnes, K. A.; Scholey, A. B. Modulation of mood and cognitive performance following acute administration of single doses of Melissa officinalis (lemon balm) with human CNS nicotinic and muscarinic receptor-binding properties. Neuropsychopharmacology 2003, 28, 1871-1881, 10.1038/sj.npp.1300230
9. Escobar, P.; Milena Leal, S.; Herrera, L. V.; Martinez, J. R.; Stashenko, E. Chemical composition and antiprotozoal activities of Colombian Lippia spp. essential oils and their major components. Mem. Inst. Oswaldo Cruz 2010, 105, 184-190, 10.1590/S0074-02762010000200013
10. Topal, U.; Sasaki, M.; Goto, M.; Otles, S. Chemical compositions and antioxidant properties of essential oils from nine species of Turkish plants obtained by supercritical carbon dioxide extraction and steam distillation. Int. J. Food Sci. Nutr. 2008, 59, 619-634, 10.1080/09637480701553816
11. Marques, T. H. C.; Marques, M. L. B. G. C. B.; Lima, D. d. S.; Siqueira, H. D. á. S.; Neto, J. D. N.; Branco, M. S. B. G. C.; Souza, A. A. d.; Sousa, D. P. d.; Freitas, R. M. d. Evaluation of the neuropharmacological properties of nerol in mice. World J. Neurosci. 2013, 03, 32-38, 10.4236/wjns.2013.31004
12. Lapczynski, A.; Foxenberg, R. J.; Bhatia, S. P.; Letizia, C. S.; Api, A. M. Fragrance material review on nerol. Food Chem. Toxicol. 2008, 46, S241-S244, 10.1016/j.fct.2008.06.062
13. Kladar, N. V.; Anackov, G. T.; Rat, M. M.; Srdenovic, B. U.; Grujic, N. N.; Sefer, E. I.; Bozin, B. N. Biochemical Characterization of Helichrysum italicum (Roth) G.Don subsp. italicum (Asteraceae) from Montenegro: phytochemical screening, chemotaxonomy, and antioxidant properties. Chem. Biodiversity 2015, 12, 419-431, 10.1002/cbdv.201400174
14. Charles, D. J.; Simon, J. E. Volatile compounds of the curry plant. HortScience 1991, 26, 69-70
15. Chadha, A.; Madyastha, K. M. Metabolism of geraniol and linalool in the rat and effects on liver and lung microsomal enzymes. Xenobiotica 1984, 14, 365-374, 10.3109/00498258409151425
16. Wirth, J.; Guo, W.; Baumes, R.; Gunata, Z. Volatile compounds released by enzymatic hydrolysis of glycoconjugates of leaves and grape berries from Vitis vinifera Muscat of Alexandria and Shiraz cultivars. J. Agric. Food Chem. 2001, 49, 2917-2923, 10.1021/jf001398l
17. Aubert, C.; Ambid, C.; Baumes, R.; Günata, Z. Investigation of bound aroma constituents of yellow-fleshed nectarines (Prunus persica L. cv. Springbright). Changes in bound aroma profile during maturation. J. Agric. Food Chem. 2003, 51, 6280-6286, 10.1021/jf034613h
18. Bianco, A.; Passacantilli, P.; Nicoletti, M.; Alves de Lima, R. Iridoids in equatorial and tropical flora. Part 4. Isolation of amareloside. Planta Med. 1982, 46, 33-37, 10.1055/s-2007-970013
19. Lota, M. L.; de Rocca Serra, D.; Tomi, F.; Jacquemond, C.; Casanova, J. Volatile components of peel and leaf oils of lemon and lime species. J. Agric. Food Chem. 2002, 50, 796-805, 10.1021/jf010924l
20. Sarrou, E.; Chatzopoulou, P.; Dimassi-Theriou, K.; Therios, I. Volatile constituents and antioxidant activity of peel, flowers and leaf oils of Citrus aurantium L. growing in Greece. Molecules 2013, 18, 10639-10647, 10.3390/molecules180910639
21. Venskutonis, P. R.; Dagilyte, A. Composition of essential oil of sweet flag (Acorus calamus L.) leaves at different growing phases. J. Essent. Oil Res. 2003, 15, 313-318, 10.1080/10412905.2003.9698598
22. Aldrich, J. R.; Oliver, J. E.; Waite, G. K.; Moore, C.; Waters, R. M. Identification of presumed pheromone blend from Australasian predaceous bug, Oechalia schellenbergii (Heteroptera: Pentatomidae). J. Chem. Ecol. 1996, 22, 729-738, 10.1007/BF02033582
23. Elsharif, S. A.; Banerjee, A.; Buettner, A. Structure-odor relationships of linalool, linalyl acetate and their corresponding oxygenated derivatives. Front. Chem. 2015, 3, 57, 10.3389/fchem.2015.00057
24. van den Dool, H.; Kratz, P. D. A Generalization of the retention index system including linear temperature programmed gas-liquid partitionchromatography. J. Chromatogr. 1963, 11, 463-471, 10.1016/S0021-9673(01)80947-X
25. Czerny, M.; Brueckner, R.; Kirchhoff, E.; Schmitt, R.; Buettner, A. The influence of molecular structure on odor qualities and odor detection thresholds of volatile alkylated phenols. Chem. Senses 2011, 36, 539-553, 10.1093/chemse/bjr009
26. Czerny, M.; Christlbauer, M.; Christlbauer, M.; Fischer, A.; Granvogl, M.; Hammer, M.; Hartl, C.; Hernandez, N.; Schieberle, P. Re-investigation on odour thresholds of key food aroma compounds and development of an aroma language based on odour qualities of defined aqueous odorant solutions. Eur. Food Res. Technol. 2008, 228, 265-273, 10.1007/s00217-008-0931-x
27. Wakayama, S.; Namba, S.; Hosoi, K.; Ohno, M. The synthesis and the absolute configurations of lilac alcohols, new naturally occurring odorous ingredients of lilac flower. Bull. Chem. Soc. Jpn. 1973, 46, 3183-3187, 10.1246/bcsj.46.3183
28. Liu, H.-x.; Chen, X.-h.; Huang, C.-s. Facile and efficient syntheses of (±)-(E)-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid and its methyl ester. Chem. Res. Chin. Univ. 2003, 19, 425-427
29. Ward, D. E.; Rhee, C. K. Chemoselective reductions with sodium borohydride. Can. J. Chem. 1989, 67, 1206-1211, 10.1139/v89-182
30. Nakai, T.; Yajima, A.; Akasaka, K.; Kaihoku, T.; Ohtaki, M.; Nukada, T.; Ohrui, H.; Yabuta, G. Synthesis of the four stereoisomers of 2,6-dimethyloctane-1,8-dioic acid, a component of the copulation release pheromone of the cowpea weevil. Biosci., Biotechnol., Biochem. 2005, 69, 2401-2408, 10.1271/bbb.69.2401
31. Holsclaw, C. M.; Sogi, K. M.; Gilmore, S. A.; Schelle, M. W.; Leavell, M. D.; Bertozzi, C. R.; Leary, J. A. Structural characterization of a novel sulfated menaquinone produced by stf3 from Mycobacterium tuberculosis. ACS Chem. Biol. 2008, 3, 619-624, 10.1021/cb800145r
32. Ono, T.; Koutari, S.; Marumoto, S.; Miyazawa, M. Novel compound, (2Z,6E)-1-hydroxy-3,7-dimethyl-2,6-octadien-8-oic acid produced from biotransformation of nerol by Spodoptera litura larvae. J. Oleo Sci. 2013, 62, 313-318, 10.5650/jos.62.313
33. Tomooka, K.; Komine, N.; Fujiki, D.; Nakai, T.; Yanagitsuru, S.-i. Planar chiral cyclic ether: asymmetric resolution and chirality transformation. J. Am. Chem. Soc. 2005, 127, 12182-3, 10.1021/ja053347g
34. Pinnick, H. W.; Bal, B. S.; Childers, W. E., Jr. Oxidation of α,β-unsaturated aldehydes. Tetrahedron 1981, 37, 2091-2096, 10.1016/S0040-4020(01)97963-3
35. Wise, P. M.; Olsson, M. J.; Cain, W. S. Quantification of odor quality. Chem. Senses 2000, 25, 429-443, 10.1093/chemse/25.4.429
36. Chambers, E., IV; Smith, E. C.; Seitz, L. M.; Sauer, D. B. Sensory properties of musty compounds in food. In Developments in Food Science; Contis, E. T., Ho, C.-T., Mussinan, C. J., Parliment, T. H., Shahidi, F., Spanier, A. M., Eds.; Elsevier, 1998; Vol. 40, pp 173-180.
37. Jong, S.; Birmingham, J. Mushrooms as a source of natural flavor and aroma compounds. Mushroom Biol. Mushroom Prod. 1993, 345-366
38. Toledo, P. R. A. B.; Pezza, L.; Pezza, H. R.; Toci, A. T. Relationship between the different aspects related to coffee quality and their volatile compounds. Compr. Rev. Food Sci. Food Saf. 2016, 15, 705-719, 10.1111/1541-4337.12205
39. Rao, B. R. R.; Kaul, P. N.; Syamasundar, K. V.; Ramesh, S. Chemical profiles of primary and secondary essential oils of palmarosa (Cymbopogon martinii (Roxb.) Wats var. motia Burk.). Ind. Crops Prod. 2005, 21, 121-127, 10.1016/j.indcrop.2004.02.002
40. Charles, D. J.; Simon, J. E. A new geraniol chemotype of Ocimum gratissimum L. J. Essent. Oil Res. 1992, 4, 231-234, 10.1080/10412905.1992.9698054
41. Sari, A. O.; Ceylan, A. Yield characteristics and essential oil composition of lemon balm (Melissa officinalis L.) grown in the Aegean region of Turkey. Turk. J. Agric. For. 2002, 26, 217-224
42. Yakoubi, M.; Belboukhari, N.; Sekkoum, K.; Cheriti, A.; Bouchekara, M.; Aboul-Enein, H. Y. The chemical composition of essential oil of Warionea saharae Benth & Coss.(Fam. Asteraceae) from southern Algeria. Curr. Bioact. Compd. 2015, 11, 116-121, 10.2174/1573407211666150605224634
43. Dekic, M. S.; Radulovic, N. S.; Randelovic, V. N.; Stojanovic-Radic, Z. Z.; Veljkovic, B. P. Essential oils and diethyl ether extracts of Serbian Xeranthemum cylindraceum and X. annum: chemical composition, antimicrobial activity, and chemotaxonomic implications. Chem. Biodiversity 2015, 12, 1378-1397, 10.1002/cbdv.201400316
44. Ojeda de Rodriguez, G.; Ysambertt, F.; Sulbaran de Ferrer, B.; Cabrera, L. Volatile fraction composition of Venezuelan sweet orange essential oil (Citrus sinensis (L.) Osbeck). Ciencia (Maracaibo, Venez.) 2003, 11, 55-60
45. Lee, K. Y.; Kim, S. H.; Sung, S. H.; Kim, Y. C. Inhibitory constituents of lipopolysaccharide-induced nitric oxide production in BV2 microglia isolated from Amomum tsao-ko. Planta Med. 2008, 74, 867-869, 10.1055/s-2008-1074552
46. Schulz, S.; Boppre, M.; Vane-Wright, R. I. Specific mixtures of secretions from male scent organs of African milkweed butterflies (Danainae). Philos. Trans. R. Soc., B 1993, 342, 161-181, 10.1098/rstb.1993.0144
47. Chin, Y. W.; Chai, H. B.; Keller, W. J.; Kinghorn, A. D. Lignans and other constituents of the fruits of Euterpe oleracea (acai) with antioxidant and cytoprotective activities. J. Agric. Food Chem. 2008, 56, 7759-64, 10.1021/jf801792n
48. Feng, T.; Su, J.; Ding, Z.-H.; Zheng, Y.-T.; Li, Y.; Leng, Y.; Liu, J.-K. Chemical constituents and their bioactivities of "Tongling white ginger" (Zingiber officinale). J. Agric. Food Chem. 2011, 59, 11690-11695, 10.1021/jf202544w
49. Liu, J.; Nakamura, S.; Xu, B.; Matsumoto, T.; Ohta, T.; Fujimoto, K.; Ogawa, K.; Fukaya, M.; Miyake, S.; Yoshikawa, M.; Matsuda, H. Chemical structures of constituents from the flowers of Osmanthus fragrans var. aurantiacus. J. Nat. Med. 2015, 69, 135-141, 10.1007/s11418-014-0869-1