Korean Journal of Pharmacognosy (생약학회지)

The Korean Society of Pharmacognosy (한국생약학회)
권호 표지

Constituents of Cynanchum auriculatum and their Inhibitory Effect on Melanogenesis in B16 Mouse Melanoma Cell Lines

이엽우피소의 성분 및 멜라닌 생성 억제활성

  • Choi, Hyun-Gyu (College of Pharmacy, Yeungnam University) ;
  • Jiang, Yanfu (College of Pharmacy, Yeungnam University) ;
  • Roh, Eun-Mi-Ri (College of Pharmacy & Research Center for Bioresource and Health, Chungbuk National University) ;
  • Kim, Young-Soo (College of Pharmacy & Research Center for Bioresource and Health, Chungbuk National University) ;
  • Xu, Guang-Hua (College of Pharmacy, Yeungnam University) ;
  • Na, Min-Kyun (College of Pharmacy, Yeungnam University) ;
  • Lee, Seung-Ho (College of Pharmacy, Yeungnam University)
  • Received : 2010.11.05
  • Accepted : 2010.11.23
  • Published : 2011.12.31
Download PDF
⟨ Previous Next ⟩

Abstract

Fourteen compounds were isolated from the roots of Cynanchum auriculatum and their chemical structures were identified as ${\beta}$-sitosterol (1), acetovanillone (2), p-hydroxyacetophenone (3), 2,4-dihydroxyacetophenone (4), 2,5-dihydroxyacetophenone (5), cynandione A (6), methyleugenol (7), daucosterol (8), Succinic acid (9), cynauriculoside A (10), wilfoside C3N (11), wilfoside C1N (12), wilfoside K1N (13) and wilfoside C1G (14). Among them, compounds 2-5 were isolated from this plant for the first time. And 2, 5-dihydroxyacetophenone (5) showed the most potent inhibitory effect on melanogenesis in B-16 mouse melanoma cell lines with $IC_{50}$ value of $20\;{\mu}M$.

Keywords

References

  1. Zhang. (2006) 上海科學技術出版社, 中約大辭典 : 4594
  2. Zhang, J. F., Li, Y. B., Li, C. L. and Jiang, J. Q. (2006) Studies on chemical constituents in root tuber of Cynanchum auriculatum, Zhongguo Zhong Yao Za Zhi 31(10): 814-816.
  3. Song, J., Tao, G., Yang, J. and Ding, X. (2002) Isolation and characterization of steroidal aglycones from Cynanchum auriculatum, J. of Wuxi University of Light Industry 21(2): 176-178.
  4. Wang, Y., Yan, X., Gong, S. and Fu, W. (2002) Two New C-21 Steroidal glycosides from Cynanchum aurichulatum, Chinese Chemical letters 13(6): 543-546.
  5. Gu, X. J., Yao, N., Qian, S. H., Li, Y. B. and Li, P. (2009) Four New C21 Steroidal glycosides from the roots of Cynanchum auriculatum, Helv. Chim. Acta, 92: 88-92. https://doi.org/10.1002/hlca.200800186
  6. 徐凌川, 张华, 许昌盛(2003) 白首乌化学成分与药理现代研究述评, 中医药学刊, 21(11),1893-1895
  7. 함인혜, 이주영, 윤예진, 양갑식, 태진, 부영민, 김호철, 최호영 (2007) 국산 및 중국산 白首烏의 Triton WR-1339 유발 高脂血症 흰쥐에 대한 효능 연구, 대한본초학회지 22(4): 279-286.
  8. Min, Y., Xu, F. and Dong, Y. (2004) Advances in research of chemistry and pharmacology of Bai-shou-wu, Chinese Wild Plant Resources 23(2): 8-11.
  9. 김민자, 송범헌, 남상영, 김인재, 이철희, 윤태 (2005) 백수오 (이엽우피소)의 무지주 재배방법에 따른 생육 및 수량, 한국약용작물학회지 13(6): 268-272.
  10. Moon, B. C., Choo, B. K., Cheon, M. S., Yoon, T., Ji, Y., Kim, B. B., Lee, A. Y. and Kim, H. K. (2010) Rapid molecular authentication of three medicinal plant species, Cynanchum wilfordii, C. auriculatum, and Polygonum multiflorum by the development of RAPD-derived SCAR markers and multiplex-PCR, Plant Biotechnol. Rep. 4: 1-7. https://doi.org/10.1007/s11816-009-0114-7
  11. 김호경, 김영아, 이아영, 고병섭 (2003) 백수오와 하수오의 패턴분석 연구, 생약학회지 34(4): 278-281.
  12. Kobayashi, T., Urabe, K., Winder, A., Jimenez-Cervantes, C., Imokawa, G., Brewington, T., Solano, F., Garcia-Borron, J. C. and Hearing, V. J. (1994) Tyrosinase related protein 1 (TRP1) functions as a DHICA oxidase in melanin biosynthesis, EMBO J. 13, 5818-5825.
  13. De. Eknamkul, W. and Potduang, B. (2003) Biosynthesis of $\beta$-sitosterol and stigmasterol in Croton sublyratus proceeds via a mixed origin of isoprene units. Phytochemistry 62: 389-398. https://doi.org/10.1016/S0031-9422(02)00555-1
  14. Junior, P. (1986) Acetophenonglucoside aus Penstemon pinifolius. Planta Med. 52: 218-220. https://doi.org/10.1055/s-2007-969127
  15. Hoque, E. (1984) Spruce die-back: Isolation of p-hydroxy-acetophenone from diseased shoots of Picea abies. Phytochemistry 23: 923-925. https://doi.org/10.1016/S0031-9422(00)85068-2
  16. Lin, C. N., Huang, P. L., Lu, C. M., Yen, M. H. and Wu, R. R. (1997) Revised structure for five acetophenones from Cynanchum taiwanianum. Phytochemistry 4: 1359-1363.
  17. Akamanchi, K. G., Padmawar, P. A., Thatte, U. M., Rege, N. N. and Dahanukar, S. A. (1999) Synthesis and in-vitro evaluation of platelet aggregation inhibitory activity of paeonol and its analogues. Pharm. Pharmacol. Commun. 5: 323-329. https://doi.org/10.1211/146080899128734910
  18. Lin, Y. L. and Lin, T. C. (1997) Two acetophenone glucosides, cynanonesides A and B, from Cynanchum taiwanianum and revision of the structure for cynandione A. J. Nat. Prod. 60: 368-370. https://doi.org/10.1021/np960256b
  19. Meepagala, K. M., Sturtz, G. and Wedge, D. E. (2002) Antifungal constituents of the essential oil fraction of Artemisia dracunculus L. Var. dracunculus. J. Arg. Food Chem. 50: 6989-6992. https://doi.org/10.1021/jf020466w
  20. Faizi, S., Ali, M., Saleem, R. and Irfanullah Bibi, S. (2001) Complete $^{1}H and ^{13}C$ NMR assignments of stigma-5-en-3-O-$\beta$-glucoside and its acetyl derivative. Magn. Reson. Chem. 39: 399-405. https://doi.org/10.1002/mrc.855
  21. Nord, L. I., Vaag, A. and Duus, J. O. (2004) Quantification of organic and amino acids in beer by $^{1}H$ NMR Spectroscopy. Anal. Chem. 76: 47901-4798.
  22. Tsukamoto, S., Hayashi, K. and Mitsuhashi, H. (1985) The structures of six glycosides, wilfoside C1N, C2N, C3N, C1G, C2G and C3G, with novel sugar chain containing a pair of optically isomeric sugars. Tetrahedron 41: 927-934. https://doi.org/10.1016/S0040-4020(01)96411-7