Constituents of the seeds of Cornus officinalis with Inhibitory Activity on the Formation of Advanced Glycation End Products (AGEs)

산수유 씨의 최종당화산물 생성저해활성 성분

  • Lee, Ga-Young (Department of Herbal Pharmaceutical Development, Korea Institute of Oriental Medicine) ;
  • Jang, Dae-Sik (Department of Herbal Pharmaceutical Development, Korea Institute of Oriental Medicine) ;
  • Lee, Yun-Mi (Department of Herbal Pharmaceutical Development, Korea Institute of Oriental Medicine) ;
  • Kim, Young-Sook (Department of Herbal Pharmaceutical Development, Korea Institute of Oriental Medicine) ;
  • Kim, Jin-Sook (Department of Herbal Pharmaceutical Development, Korea Institute of Oriental Medicine)
  • 이가영 (한국한의학연구원 한약제제연구부) ;
  • 장대식 (한국한의학연구원 한약제제연구부) ;
  • 이윤미 (한국한의학연구원 한약제제연구부) ;
  • 김영숙 (한국한의학연구원 한약제제연구부) ;
  • 김진숙 (한국한의학연구원 한약제제연구부)
  • Published : 2008.12.31


Ten compounds, (+)-pinoresinol (1), (-)-balanophonin (2), gallicin (3), vanillin (4), 4-hydroxybenzaldehyde (5), coniferaldehyde (6), betulinic acid (7), ursolic acid (8), 5-hydroxymethyl furfural (9), and malic acid (10), were isolated from a EtOAc-soluble fraction of the seeds of Cornus officinalis. The structures of these compounds were elucidated by spectroscopic methods as well as by comparison with reported values. Compounds 1, 2, and 4-7 were isolated from this species for the first time. All the isolates (1-10) were subjected to an in vitro bioassay to evaluate their inhibitory activity against advanced glycation end products (AGEs) formation. Among these, compounds 2 and 3 showed the significant inhibitory activity on AGEs formation with $IC_{50}$ values of 27.81 and 18.04${\mu}M$, respectively.


  1. Larkins, R. G. and Dunlop, M. E. (1992) The link between hyperglycaemiaand diabetic nephropathy. Diabetologia 35, 499- 504
  2. Yokwzawa, T., Nakagawa, T. and Terasawa, K. (2001) Effects of Oriental medicines on the production of advanced glycation endproducts. J. Trad. Med. 18, 107-112
  3. Chang, I.-M. (2003) Treatise on Asian Herbal Medicines. Seoul National University Hak Sool Pyun Soo Gwan, Seoul, Korea
  4. Bae, K. H. (2000) Medicinal Plants of Korea. Kyo-Hak Publishing Co., Seoul, Korea
  5. Okuda, T., Hatano, T., Ogawa, N., Kira, R. and Matsuda, M. (1984) Cornusiin A, a dimeric ellagitannin forming four tautomers, and accompanying new tannins in Cornus officinalis. Chem. Pharm. Bull. 32, 4662-4665
  6. Whang, J. I., Moon, H. I. and Zee, O. P. (2000) Phytochemical constituents of Actinidia arguta. Kor. J. Pharmacogn. 31, 357-363
  7. Sy, L. K and Brown, G. D. (1999) Coniferaldehyde derivatives from tissue culture of Artemisia annua and Tanacetum parthenium. Phytochemistry 50, 781-785
  8. Sakurai, T. and Tsuchiya, S. (1988) Superoxide production from nonenzymatically glycated protein. FEBS Lett. 236, 406-410
  9. Hatano, T., Yasuhara, T., Abe, R. and Okuda, T. (1990) A galloylated monoterpene glucoside and a dimeric hydrolysable tannin from Cornus officinalis. Phytochemistry 29, 2975-2978
  10. Brownlee, M. (1996) Advanced glycation endproducts in diabetic complications. Curr. Opinion Endocrinol. Diabetes 3, 291-29
  11. Miyazawa, M. and Kameoka, H. (1989) Volatile flavor components of Corni fructus. Agric. Biol. Chem. 53, 3337-3340
  12. Forbes, J. M., Cooper, M. E., Oldfield, M. D. and Thomas, M. C. (2003) Role of advanced glycation end products in diabetic nephropathy. J. Am. Soc. Nephrol. 14, S254-S258
  13. Mitsuo, M., Jun, A., Jun, F. and Yukio, I. (2003) Insecticidal compounds against drosophila melanogaster from Cornus officinalis Sieb. et. Zucc. Nat. Prod. Res. 17, 337-339
  14. Seo, K. I., Lee, S. W. and Yang, K. H. (1999) Antimicrobial and Antioxidative Activities of Corni fructus extracts. Kor. J. Postharvest Sci. Technol, 6, 99-103
  15. Kim, B. H., Park, K. W., Kim, J. Y., Jeong, I. Y., Yang, G. H., Cho, Y. S., Yee, S. T. and Seo, K. I (2004) Purification and characterization of anticarcinogenic compound from Corni fructus. Korean J. Food Sci. Technol. 36, 1001-1007
  16. Endo, T. and Taguchi, H. (1973) Study on the constituents of Cornus offinalis Sieb. et Zucc. Yakugaku Zasshi 93, 30-32
  17. Kim, D. K. and Kwak, J. H. (1998) A furan derivative from Cornus officinalis. Arch. Pharm. Res. 21, 787-789
  18. Kim, D. K., Kwak, J. H., Ryu, J. H., Kwon, H. C., Song, K. W., Kang, S. S., Lee, S. H., Lee, E. A., Kwon, N. S., Lee, K. R. and Zee, O. P. (1996) A component from Cornus officinalis enhances hydrogen peroxide generation from macrophages. Kor. J. Pharmacogn. 27, 101-104
  19. Robinson, F. P. and Martel, H. (1970) Betulinic acid from Arbutus menziesii. Phytochemistry 9, 907-909
  20. Park, Y. K., Whang, W. K. and Kim, I. H. (1995) The antidiabetic effects of from Cornus officinalis seed. Chung-ang J. Pharm. Sci. 9, 5-11
  21. Rahbar, S. and Figarola, J. L. (2003) Novel inhibitors of advanced glycation endproducts. Arch. Biochem. Biophys. 419, 63-79
  22. Soren R. J., Anders K. and Bent J. N. (1973) Loniceroside (secologanin) in Cornus officinalis and C. mas. Phytochemistry 12, 2064-2065
  23. Tian, G., Zhang, T., Yang, F. and Ito, Y. (2000) Separation of gallic acid from Cornus officinalis Sieb. et Zucc by high-speed counter-current chromatography. J. Chromatogr. A. 886, 309-312
  24. Seo, Y. B., Kil, G. J., Lee, Y. K. and Lee, Y. C. (2002) Study on the effects of Corni fructus about the anti-allergic action. Kor. J. Herbology. 17, 1-12
  25. Bierhaus, A., Hofmann, M. A., Ziegler, R. and Nawroth, P. (1998) AGEs and their interaction with AGE-receptors in vascular disease and diabetic mellitus. I. The AGE concept. Cardiovasc. Res. 37, 586-600
  26. Hatano, T., Ogawa, N., Kira, R., Yasuhara, T. and Okuda, T. (1989) Tannins of cornaceous plants. I. Cornusiins A, B and C, dimeric monomeric and trimeric hydrolyzable tannins from Cornus officinalis, and orientation of valoneoyl group in related tannins. Chem. Pharm. Bull. 37, 2083-2090
  27. Kwon, C. H., Hong, N. D. and Kim, N. J. (1988) Studies on the constituents of Bambusae Caulis in taeniam. Kor. J. Pharmacogn. 19, 188-192
  28. Shinohara, R., Mono, T., Nagasaka, A., Sawai, Y., Uchimura, K., Hayashi, R., Hayakawa, N., Nagata, M., Makino, M., Kakizawa, H., Itoh, Y., Nakai, A. and Itoh, M. (1998) Effects of throid hormone on the sorbitol pathway in streptozotocininduced diabetic rats. Biochim. Biophys. Acta 1425, 577-586
  29. Vinson, J. A. and Howard , T. B. (1996) Inhibition of protein glycation and advanced glycation end products by ascorbic acid and other vitamins and nutrients. J. Nutr. Biochem. 7, 659-663
  30. Hong, S. S., Han, D. I., Hwang, B. Y., Choi, W. H., Kang, H. S., Lee, M. K., Lee, D. K., Lee, K. S. and Ro, J. S. (2001) Chemical components from the stem bark of Kalopanax septemlobus. Kor. J. Pharmacogn. 32, 302-306

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