Discovery of aromatic components with excellent fragrance properties and biological activities: β-ionols with antimelanogenetic effects and their asymmetric syntheses

Chemical and Pharmaceutical Bulletin

Volumn 61, Issue 3, 2013, Pages 310-314

  Komaki, Ryoichi ^a   Ikawa, Takashi ^b   Saito, Kozumo ^b   Hattori, Kazuyo ^a   Ishikawa, Natsuyo ^a   Fukawa, Hidemichi ^c   Egi, Masahiro ^b   Akai, Shuji ^b  

^a KANEBO LTD   (Japan)

^b UNIVERSITY OF SHIZUOKA   (Japan)

^c Yukiguni Aguri Co Ltd   (Japan)

Author keywords

Antimelanogenetic effect; Aromatic component; Asymmetric synthesis; Dihydro ionol; Lipase catalyzed kinetic resolution; Osmanthus flower

Indexed keywords

4 (2,6,6 TRIMETHYLCYCLOHEX 1 ENYL)BUTAN 2 OL; BUTYLCRESOL; FRAGRANCE; O ACETYL BETA IONOL; UNCLASSIFIED DRUG;

ANTIMELANOGENETIC EFFECT; ARTICLE; ASYMMETRIC SYNTHESIS; BIOLOGICAL ACTIVITY; DRUG EFFECT; DRUG STRUCTURE; ENANTIOMER; MELANOMA; PEACH; RACEMIC MIXTURE;

BIOLOGICAL FACTORS; CATALYSIS; FLOWERS; KINETICS; LIPASE; NORISOPRENOIDS; PERFUME; PRUNUS;

EID: 84875457986     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.c12-00916     Document Type: Article

References (31)

1. Özcan M. M., Arslan D., Food Chem., 129, 171-174 (2011).
2. Bilgrami K. S., Sinha K. K., Sinha A. K., Indian J. Med. Res., 96, 171-175 (1992).
3. Suresh P., Ingle V. K., Vijaialkshima V., J. Food Sci. Technol., 29, 254-256 (1992).
4. Pacheco P., Sierra J., Schmeda-Hirschmann G., Potter C. W., Jones B. M., Moshref M., Phytother. Res., 7, 415-418 (1993).
5. Friedman M., Henika P. R., Mandrell R. E., J. Food Prot., 65, 1545-1560 (2002).
6. Divakar N. G., Bhupal J. V. R., Indian Perfum., 24, 46-47 (1980).
7. Shaath N. A., Azzo N. B., Perfum. Flavor., 17, 49-55 (1992).
8. Verghese J., Sunny T. P., Flavour Fragrance J., 7, 323-327 (1992).
9. Takahashi K., Muraki S., Yoshida T., Agric. Biol. Chem., 45, 129-131 (1981).
10. Bayrak A., Akgül A., J. Sci. Food Agric., 64, 441-448 (1994).
11. Yu Z., Yi Y.-F., Wu Y., Yu X.-J., Wang P., Ding J.-K., Acta Botan Yunnanica, 16, 75-80 (1994).
12. Li G., Ju H. K., Chang H. W., Jahng Y., Lee S.-H., Son J.-K., Biol. Pharm. Bull., 26, 1039-1041 (2003).
13. Ando H., Watabe H., Valencia J. C., Yasumoto K., Furumura M., Funasaka Y., Oka M., Ichihashi M., Hearing V. J., J. Biol. Chem., 279, 15427-15433 (2004).
14. Yoshimura M., Watanabe Y., Kasai K., Yamakoshi J., Koga T., Biosci. Biotechnol. Biochem., 69, 2368-2373 (2005).
15. Kim K.-S., Kim J. A., Eom S.-Y., Lee S. H., Min K. R., Kim Y., Pigment Cell Res., 19, 90-98 (2006).
16. Arung E. T., Shimizu K., Kondo R., Planta Med., 72, 847-850 (2006).
17. Komaki R., 8th International Essential Oil Congress, Cannes, France, "Technical Data," 1980, pp. 394-400.
18. Gogiya V. T., Kharebava L. G., Gogiya R. V., Gvatua E. B., Lour. Rastit. Resur., 22, 243-248 (1986).
19. Deng C., Song G., Hu Y., Ann. Chim., 94, 921-927 (2004).
20. Sakamoto S., Machida K., Kikuchi M., J. Nat. Med., 62, 362-363 (2008).
21. Kaiser R., Lamparsky D., Helv. Chim. Acta, 61, 373-382 (1978).
22. Wang L.-M., Li M., Jin W., Li S., Zhang S., Yu L., Food Chem., 114, 233-236 (2009).
23. Hu C.-D., Liang Y.-Z., Guo F.-Q., Li X.-R., Wang W.-P., Molecules, 15, 3683-3693 (2010).
24. Nakayama Y., Abe S., Yamaguchi Y., Sakurai K., 55th Symposium on the Chemistry of Terpenes, Essential Oils, and Aromatics, Tsukuba, Japan (2011). Abstract Book, pp. 22-24.
25. For our preliminary studies on this project, see: Komaki R., Fukawa H., Matsumura Y., Endo T., Maruyama K., JP2002-226415 (2002).
26. Komaki R., Fukawa H., Matsumura Y., Endo T., Maruyama K., JP2002-226416 (2002).
27. Linares-Palomino P. J., Salido S., Altarejos J., Nogueras M., Sánchez A., Flavour Fragrance J., 21, 659-666 (2006).
28. Akai S., Hanada R., Fujiwara N., Kita Y., Egi M., Org. Lett., 12, 4900-4903 (2010).
29. Dihydro-β-ionol 1 is known to be present in volatile aromatic components of Hakuto peach, see: Osaki K., Yukawa C., Zhong X., Iwabuchi H., Foods and Food Ingredients Journal of Japan, 44-60 (2001).
30. Peter S., Datsevich L., Jess A., Appl. Catal. A Gen., 286, 96-110 (2005).
31. Ichikawa A., Ono H., Biosci. Biotechnol. Biochem., 72, 2418-2422 (2008).