YAKHAK HOEJI (약학회지)

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

Synthesis of Novel Kojic Acid Derivatives and Their Tyrosinase Inhibitory Activities

새로운 코직산 유도체의 합성과 티로시나제 저해활성

  • 김지연 (동덕여자대학교, 약학대학) ;
  • 임세진 (동덕여자대학교, 약학대학)
  • Published : 1999.02.01
Download PDF
⟨ Previous Next ⟩

Abstract

Four derivatives of kojic acid were synthesized and their inhibitory activities against tyrosinase were evaluated. The C-2 hydroxymethyl and C-7 hydroxyl of kojic acid were replaced by carboxylate and amine, respectively. These derivatives were coupled to L-phenylalanine, producing two amide compounds. The carboxylate derivative (3), its amide compound (5), and the amine derivative (7) were weak inhibitors. The amide compound (9) where amine derivative (7) coupled to L-phenylalanine showed strong inhibitory activity ($IC_{50}=24.6{\;}{\mu}M$) comparable to kojic acid.

Keywords

References

  1. Appl. Microbiol. v.14 Production of aflatoxins and kojic acid by species of Aspergillus and Penicillium Parrish, F. W.;Wiley, B. J.;Simmons, E. G.;Lomg, L., Jr.
  2. Agric. Biol. Chem. v.43 no.6 Kojic acid, a tyrosinase inhibitor from Aspergillus albus Saruno, R.;Kato, F.;Ikeno, T.
  3. Fragrance J. v.6 Melanogenesis-inhibitory effect of kojic acid and its action mechanism Ohyama, Y.
  4. Jpn. Kokai. Tokyo Koho Cosmetic skin whitening by food containing kojic acid and its esters Obara, Y.;Ito, T.;Hizu, Y.
  5. J. Am. Chem. Soc. v.103 Competitive inhibitor binding to the binuclear copper active site in tyrosinase Winkler, M. E.;Lerch, K.;Solomon, E. I.
  6. JP 01121206 Whitening cosmetic material contains kojic acid and guanosine-3'-5'-cyclic monophosphate
  7. Bioorg. Medicin. Chem. Lett. v.6 no.12 Synthesis of N-kojic-amino acid and N-Konic-amino acid-kojiate and their tyrosinase inhibitory activity Kobayashi, Y.;Kayahara, H.;Tadasa, K.;Tanaka, H.
  8. J. Pol. Sci. Pt. A-Pol. Chem. v.34 no.2 Synthesis and radical polymerization of styrene derivative bearing kojic acid moieties Tomita, I.;Mitsuhashi, K.;Endo, T.
  9. 약학회지 v.42 no.1 멜라닌생성 억제제인 코직산 모노스테아레이트의 가수분해와 피부투과특성 및 in vivo 미백효과 하용호;유서운;김동섭;임세진;최영욱ㅇ
  10. EP-417632 Pharmaceutical compsn. contg. kojic acid for treatment of endogenous chloasma. senile moles, sunlight-induced moles or pigmented-spot after inflammation
  11. JP 61289086 Kojic acid phosphate(s) for extemal skin care prepd. form 7-hydroxy (un)protected kojic acid halide in organic solvent folowed by hydrolysis
  12. J. Jpn. Soc. Food. Sci. Tech. v.42 no.8 Comparison of some properies of kojic acid glucoside with kojic acid Nishimura, T.;Kometani, T.lTakii, H.;Terada, Y.;Okada, S.
  13. Planta Med. v.64 The inhibitory components from artocarpus incisus on melanin biosynthesis Shimizu, K.;Kondo, R.;Sakai, K.;Lee, S.;Sato, H.
  14. J. Soc. Ind. Appl. Math. v.11 An algorithm for least-squares estimation of nonlinear parameters Marquardt, D.W.
  15. Biosci. Biotech. Biochem. v.59 no.9 Synthesis of amino acid derivatives of kojic acid and their tyrosinase inhibitory activity Kobayashi, Y.;Kayahara, H.;Tadasa, K.;Nakamura, T.;Tanaka, H.