Lipase-catalyzed synthesis of capsaicin analogs by transacylation of capsaicin with natural oils or fatty acid derivatives in n-hexane

Biotechnology Letters

Volumn 21, Issue 6, 1999, Pages 547-550

  Kobata, Kenji ^a   Kobayashi, Mamiko ^a   Tamura, Yukiyoshi ^b   Miyoshi, Shozo ^b   Ogawa, Susumu ^b   Watanabe, Tatsuo ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

^b Maruzen Pharmaceuticals Co   (Japan)

Author keywords

Capsaicin analog; Lipase; Natural oil; Transacylation; Triacylglyceride

Indexed keywords

CAPSAICIN; CAPSAICIN DERIVATIVE; FATTY ACID DERIVATIVE; HEXANE; MYRISTIC ACID; OLIVE OIL; OLVANIL; PERILLA OIL; SAFFLOWER OIL; TRIACYLGLYCEROL LIPASE; TRIOLEIN;

ACYLATION; ARTICLE; CATALYST; SYNTHESIS; TEMPERATURE; TIME;

EID: 0032768694     PISSN: 01415492     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1005567923159     Document Type: Article

References (10)

1. Buck SH, Burks TF (1986) The neuropharmacology of capsaicin: review of some recent observations. Pharmacol. Rev. 38: 179-226.
2. Campbell EA, Dray A, Perkins MN (1989) Comparison of capsaicin and olvanil as antinociceptive agents in vivo and in vitro. Br. J. Pharmacol. 98:907.
3. Kobata K, Yoshikawa K, Kohashi M, Watanabe T (1996) Enzymatic synthesis of capsaicin analogs with liver acetone powder. Tetrahedron Lett. 37: 2789-2790.
4. Kobata K, Kawamura M, Toyoshima M, Tamura Y, Ogawa S, Watanabe T (1998a) Lipase-catalyzed synthesis of capsaicin analogs by amidation of vanillylamine with fatty acid derivatives. Biotechnol. Lett. 20: 451-453.
5. Kobata K, Toyoshima M, Kawamura M, Watanabe T (1998b) Lipase-catalyzed synthesis of capsaicin analogs using natural oils as an acyl donor. Biotechnol. Lett. 20: 781-783.
6. Sietsema WK, Berman EF, Farmer RW, Maddin CS (1988) The antinociceptive effect and pharmacokinetics of olvanil following oral and subcutaneous dosing in the mouse. Life Sci. 43: 1385-1391.
7. Suzuki T, Iwai K (1984) Constituents of red pepper species: chemistry, biochemistry, pharmacology, and food science of the pungent principle of Capsicum species. In: Brossi A, ed. The Alkaloids Chemistry and Pharmacology, Vol. 23. Orlando: Academic Press, pp. 227-299.
8. Szolcsányi J (1982) Capsaicin type pungent agents producing pyrexia. In: Milton AS, ed. Handbook of Experimental Pharmacology, Vol. 60. Berlin: Springer-Verlag, pp. 437-478.
9. Watanabe T, Kawada T, Kato T, Harada T, Iwai K (1994) Effects of capsaicin analogs on adrenal catecholamine secretion in rats Life Sci. 54: 369-374.
10. Zaks A, Klibanov AM (1985) Enzyme-catalyzed processes in organic solvents. Proc. Natl. Acad. Sci. 82: 3192-3196.