Development of Biologically Active Compounds from Edible Plant Sources-XIX. Isolation of Inhibitory Compound on LDL-Oxidation from the Aerial Parts of Sajabalssuk (Artemisia princeps PAMPANINI, Sajabalssuk)

식용식물자원으로부터 활성물질의 탐색-XIX. 사자발쑥(Artemisia princeps PAMPANINI, Sajabalssuk)의 전초로부터 저밀도 지질 단백질(LDL) 산화 억제물질의 분리

  • Bang, Myun-Ho (Ganghwa Agricultural R&D Center) ;
  • Song, Myoung-Chong (The Graduate School of Biotechnology & Plant Metabolism Research Center, Kyung Hee University) ;
  • Han, Min-Woo (The Graduate School of Biotechnology & Plant Metabolism Research Center, Kyung Hee University) ;
  • Lee, Dae-Young (The Graduate School of Biotechnology & Plant Metabolism Research Center, Kyung Hee University) ;
  • Jo, Jin-Kyung (The Graduate School of Biotechnology & Plant Metabolism Research Center, Kyung Hee University) ;
  • Chung, Hae-Gon (Ganghwa Agricultural R&D Center) ;
  • Jeong, Tae-Sook (National Research Laboratory of Lipid Metabolism & Atherosclerosis, Korea Research Institute of Bioscience and Biotechnology) ;
  • Lee, Kyung-Tae (Department of Biochemistry, College of Pharmacy, Kyung Hee University) ;
  • Choi, Myung-Sook (Department of Food Science and Nutrition, Kyungpook National University) ;
  • Baek, Nam-In (The Graduate School of Biotechnology & Plant Metabolism Research Center, Kyung Hee University)
  • 방면호 (강화군 특화작목연구소) ;
  • 송명종 (경희대학교 생명공학원 및 식물대사연구센터) ;
  • 한민우 (경희대학교 생명공학원 및 식물대사연구센터) ;
  • 이대영 (경희대학교 생명공학원 및 식물대사연구센터) ;
  • 조진경 (경희대학교 생명공학원 및 식물대사연구센터) ;
  • 정해곤 (강화군 특화작목연구소) ;
  • 정태숙 (한국생명공학연구원 지질대사연구실) ;
  • 이경태 (경희대학교 약학대학 약품생화학교실) ;
  • 최명숙 (경북대학교 식품영양학과) ;
  • 백남인 (경희대학교 생명공학원 및 식물대사연구센터)
  • Published : 2007.09.30

Abstract

Sajabalssuk (Artemisia princeps PAMPANINI) was extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH and $H_{2}O$, successively. From the EtOAc fraction, two phenylpropanoids were isolated through the repeated silica gel and ODS column chromatographies. From the results of physico-chemical data including NMR, MS and IR, the chemical structures of the phenylpropanoids were determined as eugenol (1) and (-)-sesamin (2). They were the first to be isolated from Sajabalssuk (Artemisia princeps PAMPANINI, Sajabalssuk). Also, eugenol inhibited LDL-oxidation with the inhibitory activity of 87.8 ${\pm}$ 1.0% at a concentration of 40 ${\mu}g/ml$.

사자발쑥의 전초를 80% MeOH 용액으로 추출하고, 얻어진 추출물을 EtOAc, n-BuOH 및 물로 용매 분획 하였다. 이 중 EtOAc 분획으로부터 silica gel과 octadecyl silica gel(ODS)column chromatography로 정제하여 2종의 phenylpropanoids 화합물을 분리하였다. 각 화합물의 화학구조는 NMR, MS 및 IR등의 스펙트럼 데이터를 해석하여 eugenol(1) 및 (-)-sesamin(2)으로 동정하였다. 이 화합물들은 사자발쑥에서 처음 분리되었다. Eugenol(1)은 LDL-항산화활성 억제활성이 40 ${\mu}g/ml$ 처리 농도에서 $87.8{\pm}1.0%$로 나타났다.

Keywords

References

  1. Lee, T. B. (2003) In Coloured Flora of Korea, Hyang Mun Sa, Seoul, Korea
  2. Cho, Y. H. and Chiang, M. H. (2001) Essential oil composition and antibacterial activity of Artemisia capillaris, Artemisia argyi, and Artemisia princeps. Korean J. Intl. Agri. 13, 313- 320
  3. Ryu, S. N., Kang, S. S., Kim, J. S. and Ku, B. I. (2004) Quantitative analysis of eupatilin and jaceosidin in Artemisia herba. Korean J. Crop Sci. 49, 452-456
  4. Bang, M. H., Kim, D. H., Yoo, J. S., Lee, D. Y., Song, M. C., Yang, H. J., Jeong, T. S., Lee, K. T., Choi, M. S., Chung, H. G. and Baek, N. I. (2005) Isolation and identification of flavonoids from the aerial parts of Sajabalssuk (Artemisia herba). J. Korea Soc. Appl. Biol. Chem. 48, 418-420
  5. Havel, R. J., Edger, H. A. and Bradgon, J. H. (1995) The distribution and chemical composition of ultracentrifugally separated lipoproteins in human serum. J. Clin. Invest. 34, 1345-1353
  6. Ahn, B. T., Lee, S., Lee, S. B., Lee, E. S., Kim, J. G., Bok, S. H. and Jeong, T. S. (2001) Low-density lipoprotein-antioxdant constituents of Saururus chinensis. J. Nat. Prod. 64, 1562- 1564 https://doi.org/10.1021/np0006061
  7. Pyee, J. H. (2005) Taxonomic study and phylogenetic analysis of genus Artemisia and Brassica rapa based on RAPD and metabolite profiling. Ganghwa Agricultural R&D Center. Research Report. 12-27
  8. Miyazawa, M. and Hisama, M. (2001) Suppression of chemical mutagen-induced SOS response by alkylphenols from clove (Syzygium aromaticum) in the Salmonella typhimurium TA1535/pSK1002 umu test. J. Agric. Food Chem. 49, 4019- 4025 https://doi.org/10.1021/jf0103469
  9. Zhang, F., Chu, C. H., Xu, Q., Fu, S. P., Hu, J. H., Xiao, H. B. and Liang, X. M. (2005) A new amide from Asarum forbesii Maxim. J. Asian Nat. Prod. Res. 7, 1-5 https://doi.org/10.1080/10286020310001596015
  10. Witzum, J. L. (1990) The role of monocytes and oxidized LDL in atherosclerosis. In: Atherosclerosis Reviews. Leaf A Weber PC (eds). Raven Press, New York, USA. 21, 59-69
  11. Cho, S. H., Park, Y. Y., Yoon, J. Y., Choi, S. W. and Ha, T. Y. (2006) The effect of polyphenols from safflower seed on HMG-CoA reductase (HMGR) activity LDL oxidation and Apo A1 secretion. Korean J. Food Sci. Technol. 38, 279-283
  12. Wie, M. B., Cheon, B. H., Lee, S. Y., Son, K. H., Song, D. K., Shin, T. K. and Kim, H. C. (2006) Eugenol inhibits excitotoxins-induced delayed neurotoxicity, oxidative injury and convulsion. J. Toxicol. Pub. Health. 22, 275-282
  13. Ide, T., Ashakumary, L., Takahashi, Y., Kushiro, M., Fukuda, N. and Sugano, M. (2001) (-)-sesamin a sesame phenylpropanoids, decreases fatty acid synthesis in rat liver accompanying the down-regulation of sterol regulatory element binding protein-1. Biochim. Biophys. Acta 1534, 1-13 https://doi.org/10.1016/S1388-1981(01)00167-6
  14. Yamashita, K., Nohara, Y., Katayama, K. and Namiki, M. (1992) Sesame seed phenylpropanoids and ${\gamma}$-tocopherol act synergistically to produce vitamin E activity in rats. J. Nutr. 122, 2440-2446 https://doi.org/10.1093/jn/122.12.2440
  15. Shimizu, S., Akimoto, K., Shinmen, Y., Sugano, M. and Yamada, H. (1991) (-)-sesamin is a potent and specific inhibitor of ${\Delta}$5 desaturase in polyunsatured fatty acid biosynthesis. J. Lipids Res. 26, 512-516 https://doi.org/10.1007/BF02536595
  16. Hirose, N., Inoue, T., Nishihara, K., Sugano, M., Akimoto, A., Shimizu, S. and Yamada, H. (1991) Inhibition of cholesterol absorption and synthesis in rats by (-)-sesamin, J. Lipid Res 32, 629-638
  17. Akimoto, K., Kitagawa, Y., Akamatsu, T., Hirose, N., Sugano, M., Shimizu, S. and Yamada, H. (1993) Protective effects of (-)-sesamin against liver damage caused by alcohol or carbon tetrachloride in rodents Ann. Nutr. Metab. 37, 218-224 https://doi.org/10.1159/000177771
  18. Matsumura, Y., Kita, S., Monimoto, S., Akimoto, K., Furuya, M., Oka, M. and Tanaka, T. (1995) Antihypertensive effect of (-)-sesamin I. Protection against deoxycorticosterone acetate salt-induced hypertension and cardiovascular hypertrophy. Biol. Pham. Bull. 18, 1016-1019 https://doi.org/10.1248/bpb.18.1016
  19. Hirose, N., Doi, F., Ueki, T., Akazawa, K., Chijnwa, K., Sugano, M., Akimoto, K., Shimizu, S. and Yamada, H. (1992) Suppressive effect of (-)-sesamin against 7,12-dimethylbenz[a] anthracene induced rat mammary carcinogenesis. Anticancer Res. 12, 1259-1266