본문 바로가기
HOME> 논문 > 논문 검색상세

논문 상세정보

Prenylated Flavonoids as Tyrosinase Inhibitors

Lee, Nan-Kyoung    (College of Pharmacy, Kangwon National University   ); Son, Kun-Ho    (Department of Food Nutrition, Andong National University   ); Chang, Hyeun-Wook    (College of Pharmacy, Yeungnam University   ); Kang, Sam-Sik    (Natural Products Research Institute, Seoul National University   ); Park, Hae-Il    (College of Pharmacy, Kangwon National University   ); Heo, Moon-Young    (College of Pharmacy, Kangwon National University   ); Kim, Hyun-Pyo    (College of Pharmacy, Kangwon National University  );
  • 초록

    In order to find new tyrosinase inhibitors and the effects of prenyl residue on flavonoid molecules, eight prenylated and three synthetic vinylated flavonoids were examined on their inhibitory effect against tyrosinase activity. From the results, kuwanon C, papyriflavonol A, sanggenon D and sophoflavescenol were found to possess the considerable inhibitory activity. Especially, sanggenon D is revealed as a potent inhibitor ( $IC_{50}$ =7.3<TEX> 7.3 $\mu$ M), compared to the reference compound, kojic acid ( $IC_{50}$ =24.8 <TE 24.8 $\mu$ M). However, the prenylation with isoprenyl group or the vinylation to flavonoid molecules did not enhance tyrosinase inhibitory activity.


  • 주제어

    Flavonoid .   Tyrosinase .   Skin .   Sanggenon .   Kuwanon .   Prenylation.  

  • 참고문헌 (16)

    1. Ha, T J., Yang, M. S., Jang, D. S., Choi, S. U., and Park, K. H., Inhibitory activities of flavanone derivatives isolated from Sophora flavecens for melanogenesis. Bull. Kor. Chem. Soc., 22, 97-99 (2001) 
    2. Matsuda, H., Higashino, M., Nakai, Y., linuma, M., Kubo, M., and Lang, F. A., Studies of cuticle drugs from natural sources. IV. Inhibitory effects of some Arctostaphylos plants on melanin biosynthesis. BioI. Pharm. Bull., 19, 153-156 (1996) 
    3. Son, J. K., Park, J. S., Kim, J. A., Kim, Y., Chung, S. R., and Lee, S. H., Prenylated flavonoids from the roots of Sophora flavescens with tyrosinase inhibitory activity. Planta Med., 69, 559-561 (2003) 
    4. Kubo, I., Kinst-Hori, I., Chaudhuri, S. K., Kubo, Y, Sanchez, Y., and Ogura, T., Flavonols from Heterotheca inuloides. Tyrosinase inhibitory activity and structural criteria. Bioorg. Med. Chem., 8, 1749-1755 (2000) 
    5. Shimizu, K., Kondo, R., and Sakai, K., Inhibition of tyrosinase by flavonoids, stilbenes and related-4-substituted resorcinols: structure-activity investigations. Planta Med., 66, 11-15(2000) 
    6. No, J. K., Soung, D. Y., Kim, Y. J., Shim, K. H., Jun, Y. S., Rhee, S. H., Yokozawa, T., and Chung, H. Y., Inhibition of tyrosinase by green tea components. Life Sci., 65, 241-246 (1999) 
    7. Nomura, T., Phenolic compounds of the mulberry tree and related plants. In Hertz, W., Griesebach, H., Kirby, G. W., and Tamm, C. (Eds). Progress in the chemistry of organic natural products (vol.53). Springer, Berlin, pp. 87-201, (1988) 
    8. Yokota, T., Nishio, H., Kubota, Y., and Mizoguchi, M., The inhibitory effect of glabridin from licorice extracts on melanogenesis and inflammation. Pigment Cell Res., 11, 355-361 (1998) 
    9. Kang, S. S., Kim, J. S., Son, K. H., Chang, H. W., and Kim, H. P., A new prenylated flavanone from the roots of Sophora flavescens. Fitoterapia, 71, 511-515 (2000) 
    10. Dao, T. T., Oh, J. W., Chi, Y. S., Kim, H. P., Sin, K-S., and Park, H., Synthesis and $PGE_2$ inhibitory activity of vinylated and allylated chrysin analogues. Arch. Pharm. Res., 26, 581-584 (2003) 
    11. Sanchez-Ferrer, A., Rodriguez-Lopez, J. N., Garcia-Canova, F., and Garcia-Carmona, F., Tyrosinase: a comprehensive review of its mechanism. Biochim. Biophys. Acta, 1247, 1-11 (1995) 
    12. Kim, S. J., Son, K. H., Chang, H. W., Kang, S. S., and Kim, H. P., Tyrosinase inhibitory prenylated flavonoids from Sophora flavescens. BioI. Pharm. Bull., 26, 1348-1350 (2003) 
    13. Nerya, O., Vaya, J., Musa, R., Israel, S., Ben-Arie, R., and Tamir, S., Glabrene and isoliquiritigenin as tyrosinase inhibitors from Licorice roots. J. Agric. Food Chem., 51, 1201-1207 (2003) 
    14. Kim, J. S., Byun, J. H., Kang, S. S., Son, K. H., Kim, H. P., and Chang, H. W., Isolation of flavonoids and a saponin from Echinosophora koreensis. Kor. J. Pharmacogn., 33, 110-115 (2002) 
    15. Badria, F. A. and Elgayyar, M. A., A new type of tyrosinase inhibitors from natural products as potential treatments for hyperpigmentation. Boll. Chim. Farmac., 140, 267-271 (2001) 
    16. Son, K. H., Kwon, S. J., Chang, H. W., Kim, H. P., and Kang, S. S., Papyriflavonol A, a new prenylated flavonol, from the root barks of Broussonetia papyriferra. Fitoterapia, 72, 456-458 (2001) 
  • 이 논문을 인용한 문헌 (4)

    1. 2008. "" Journal of microbiology and biotechnology, 18(1): 110~117     
    2. 2010. "" Journal of microbiology and biotechnology, 20(10): 1397~1402     
    3. 2011. "" Archives of pharmacal research : a publication of the Pharmaceutical Society of Korea, 34(12): 2087~2099     
    4. Cho, Eun Jeong ; Um, Seung In ; Han, Jeong Hoon ; Kim, Byeonghee ; Han, Sang Beom ; Jeong, Ji Hoon ; Kim, Hak Rim ; Kim, Inkyeom ; Whang, Wan Kyun ; Lee, Eunhwa ; Sohn, Uy Dong 2016. "The cytoprotective effect of Rumex Aquaticus Herba extract against hydrogen peroxide-induced oxidative stress in AGS cells" Archives of pharmacal research : a publication of the Pharmaceutical Society of Korea, 39(12): 1739~1747   

 저자의 다른 논문

  • Son, Kun-Ho (108)

    1. 1991 "Neochlorogenin from the Fruits of Solanum nigrum" 생약학회지 22 (2): 142~143    
    2. 1991 "Further Spirostanol Glycosides from the Tuber of Liriope spicata" 생약학회지 22 (2): 73~77    
    3. 1991 "쉽싸리 전초의 성분 연구(I)" 생약학회지 22 (3): 162~165    
    4. 1991 "Triterpenoids from the Roots of Rubus parvifolius" Archives of pharmacal research : a publication of the Pharmaceutical Society of Korea 14 (3): 225~230    
    5. 1992 "Flavonoids from the Leaves of Polygalga japonica" 생약학회지 23 (1): 9~13    
    6. 1992 "Flavonol Glycosides from the Leaves of Kalopanax pictum" 생약학회지 23 (4): 280~282    
    7. 1992 "Flavonoid Glycosides from the Fronds of Pyrrosia lingua" 생약학회지 23 (4): 276~279    
    8. 1993 "단풍마 근경의 Saponin 성분에 관한 연구" 생약학회지 24 (3): 187~191    
    9. 1993 "Antiinflammatory Activity of Naturally Occurring Flavone and Flavonol Glycosides" Archives of pharmacal research : a publication of the Pharmaceutical Society of Korea 16 (1): 25~28    
    10. 1993 "Triterpenoids from the Roots of Dipsacus asper" Archives of pharmacal research : a publication of the Pharmaceutical Society of Korea 16 (1): 32~35    
  • 장현욱 (69)

  • 강삼식 (212)

  • Park, Haeil (24)

  • 허문영 (61)

  • Kim, Hyun-Pyo (66)

 활용도 분석

  • 상세보기

    amChart 영역
  • 원문보기

    amChart 영역

원문보기

무료다운로드
유료다운로드

유료 다운로드의 경우 해당 사이트의 정책에 따라 신규 회원가입, 로그인, 유료 구매 등이 필요할 수 있습니다. 해당 사이트에서 발생하는 귀하의 모든 정보활동은 NDSL의 서비스 정책과 무관합니다.

원문복사신청을 하시면, 일부 해외 인쇄학술지의 경우 외국학술지지원센터(FRIC)에서
무료 원문복사 서비스를 제공합니다.

NDSL에서는 해당 원문을 복사서비스하고 있습니다. 위의 원문복사신청 또는 장바구니 담기를 통하여 원문복사서비스 이용이 가능합니다.

이 논문과 함께 출판된 논문 + 더보기