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Ergosterol Peroxide from Flowers of Erigeron annuus L.as an Anti-Atherosclerosis Agent

Kim, Dong-Hyun    (Graduate School of Biotechnology & Plant Metabolism Research Center, Kyung Hee University   ); Jung, Sung-Je    (Graduate School of Biotechnology & Plant Metabolism Research Center, Kyung Hee University   ); Chung, In-Sik    (Graduate School of Biotechnology & Plant Metabolism Research Center, Kyung Hee University   ); Lee, Youn-Hyung    (Graduate School of Biotechnology & Plant Metabolism Research Center, Kyung Hee University   ); Kim, Dae-Keun    (Department of Pharmacy, Woosuk University   ); Kim, Sung-Hoon    (Graduate School of East-West Medical Science, Kyung-Hee University   ); Kwon, Byoung-Mog    (Korea Research Institute of Bioscience and Biotechnology   ); Jeong, Tae-Sook    (Korea Research Institute of Bioscience and Biotechnology   ); Park, Mi-Hyun    (Erom Life Co. Ltd.   ); Seoung, Nak-Sul    (National Institute of Crop Science, RDA   ); Baek, Nam-In    (Graduate School of Biotechnology & Plant Metabolism Research Center, Kyung Hee University  );
  • 초록

    Flowers of Erigeron annuus L. were extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH, and H $_2$ O. Repeated silica gel and OD S column chromatography of the EtOAc fraction led to the isolation of a sterol, through activityguided fractionation, using ACAT inhibitory activity measurements. From the physico-chemical data, including NMR, MS, and IR, the chemical structure of the compound was determined to be an ergosterol peroxide (1), which has been isolated for the first time from this plant. This compound exhibited hACAT-1 and Lp-PLA $_2$ inhibitory effects, with inhibitory values of 51.6 ${\pm}$ 0.9 and 51 .7 ${\pm}$ 1.2%, at a treatment concentration of 0.23 mM.


  • 주제어

    Erigeron annuus L.   .   Compositae .   hACAT1 Inhibitory effect'Lp-PLA $_2$ Inhibitory effect .   Ergosterol peroxide.  

  • 참고문헌 (28)

    1. Brown, M. S., Dana, S. E., and Goldstein, J. L., Cholsterol ester formation in cultured human fibroblasts. J. Biol. Chem., 250, 4025-4027 (1975) 
    2. Lee, C. H., Jeong, T. S., Choi, Y. K., Hyun, B. W., Oh, G. T., Kim, E. H., Kim, J. R., Han, J. I., and Bok, S. H., Anti-atherogenic effect of citrus flavonoids, naringin and naringenin, associated with hepatic ACAT and aortic VCAM-1 and MCP-1 in high cholesterol-fed rabbits. Biochem. Biophys. Res. Commun., 284, 681-688 (2001) 
    3. Nam, K. S., Jo, Y. S., Kim, Y. H., Hyun, J. W., and Kim, H. W., Cytotoxic activities of acetoxyscirpenediol and ergosterol peroxide from Paecilomyces tenuipes. Life science, 69, 229- 237 (2001) 
    4. Tew, D. G., Southan, C., Rice, S. Q. J., Lawrence, G. M. P., Li, H., Boyd, H. F., Moores, K., Gloger, I. S., and Macphee, C. H., Purification, properties, sequencing, and cloning of a lipoprotein-associated, serine-dependent phospholipase involved in the oxidative modification of low-density lipoproteins. Arterioscler. Thromb. Vasc. Biol., 16, 591-597 (1996) 
    5. Jeong, T. S., Kim, J. R., Kim, K. S., Cho, K. H., Bae, K. H., and Lee, W. S., Inhibitory effects of multi-substituted benzylidenzethiazolidine- 2,4-diones on LDL oxidation. Bioorg. Med. Chem., 12, 4017-4023 (2004) 
    6. Rudel, L. L., Lee, R. G., and Cockman, T. L., Acyl coenzyme A:cholesterol acyltransferase types 1 and 2: structure and function in atherosclerosis. Curr. Opin. Lipidol., 12, 121-127 (2001) 
    7. Yagyu, H., Kitamine, T., Osuga, J., Tozawa, R., Chen, Z., Kaji, Y., Oka, T., Perry, S., Tamura, Y., Ohashi, K., Okazaki, H., Yahagi, N., Shionori, F., Iizuka, Y., Harada, K., Shimano, H., Yamashita, H., Gotoda, T., Yamamda, N., and Ishibashi, S. J., Absence of ACAT-1 attenuates atherosclerosis but causes dry eye and cutaneous xanthomatosis in mice with congenital hyperlipidemia. J. Biol. Chem., 275, 21324-21330 (2000) 
    8. Sliskovic, D. R., Picard, J. A., and Krause, B. R., 3 ACAT inhibitors: The search for a novel and effective treatment of hypercholesterolemia and atherosclerosis. Prog. Med. Chem., 39, 121-171 (2002) 
    9. Buhman, K. K., Accad, M., Novak, S., Choi, R. S., Wong, J. S., Hamilton, R. L., Turley, S., and Farese, R. V., Jr., Resistance to diet-induced hypercholesterolemia and gallstone formation in ACAT2-deficient mice. Nat. Med., 6, 1341-1347 (2000) 
    10. Leach, C. A., Hickey, D. M. B., Ife, R. J., Macphee, C. H., Smith, S. A., and Tew, D. G., Lipoprotein-associated PLA2 inhibitiona novel, non-lipid lowering strategy for atherosclerosis therapy. Il Farmaco., 56, 45-50 (2001) 
    11. Matsuo, M., Hashimoto, M., Suzuki, J., Iwanami, K., Tomoi, M., and Shimomura, K., Difference between Normal and WHHL Rabbits in Susceptibility to the Adrenal Toxicity of an Acyl- CoA:Cholesterol Acyltransferase Inhibitor, FR145237. Toxicol. Appl. Pharmacol., 140, 387-392 (1996) 
    12. Anderson, R. A., Joyce, C., Davis, M., Reagan, J. W., Clark, M., Shelness, G. S., and Rudel, L. L., Identification of a form of acyl-CoA:cholesterol acyltransferase specific to liver and intestine in nonhuman primates. J. Biol. Chem., 273, 26747- 26754 (1998) 
    13. Bloomer, J. C., Boyd, H. F., Hickey, D. M. B., Ife, R. J., Leach, C. A., Macphee, C. H., Milliner, K. J., Pinto, I. L., Rawlings, D. A., Smith, S. A., Stansfield, I. G., Stanway, S. J., Taylor, M. A., Theobald, C. J., and Whittaker, C. M., 1-(Arylpiperazinylamidoalkyl)- pyrimidones: orally active inhibitors of lipoproteinassociated phospholipase $A_{2}$. Bioorg. Med. Chem. Lett., 11, 1925-1929 (2001) 
    14. Cases, S., Novak, S., Zheng, Y., Myers, H. M., Lear, S. R., Sande, E., Welch, C. B., Lusis, A. J., Spancer, T. A., Krouse, B. R., Erickson, S. K., Jr., and Farese, R. V., Jr., ACAT-2, a second mammalian acyl-CoA: cholesterol acyltransferase. J. Biol. Chem., 273, 26755-26764 (1998) 
    15. Accad, M., Smith, S. J., Newland, D. L., Sanan, D. A., King, L. E., Jr., Linton, M. F., Fazio, S., and Farese, R., Jr., Massive xanthomatosis and altered composition of atherosclerotic lesions in hyperlipidemic mice lacking acyl CoA:cholesterol acyltransferase 1. J. Clin. Invest., 105, 711-719 (2000) 
    16. Kim, Y. K., Tomoda, H., and Nishida, H., Pyripyropenes, novel inhibitors of acyl-CoA:Cholesterol acyltransferase produced by Aspergillus fumigatus. J. Antibiot., 47, 154-162 (1994) 
    17. Dommick, M. A., Mcguire, E. J., Reindel, J. F., Bobrowski, W. F., Bocan, T. M., and Gough, A. W., Subacute Toxicity of a Novel Inhibitor of Acyl-CoA: Cholesterol Acyltransferase in Beagle Dogs. Fundam. Appl. Toxicol., 20, 217-224 (1993) 
    18. Oh, H. C., Lee, S. Y., Lee, H. S., Lee, D. H., Lee, S. Y., Chung, H. T., Kim, T. S., and Kwon, T. O., Germination inhibitory constituents from Erigeron annuus. Phytochemistry, 61, 175- 179 (2002) 
    19. Bok, J. W., Lermer, L., Chilton, J., Klingeman, H. G., and Twers, G. H. N., Antitumor sterols from the mycelia of Cordyceps sinensis. Phytochemistry, 51, 891-898 (1999) 
    20. Macphee, C. H., Moores, K. E., Boyd, H. F., Dhanak, D., Ife, R. J., Leach, C. A., Leake, D. S., Milliner, K. J., Patterson, R. A., Suckling, K. E., Tew, D. G., and Hickey, D. M. B., Lipoproteinassociated phospholipase A2, platelet-activating factor acetylhydrolase, generates two bioactive products during the oxidation of low-density lipoprotein: use of a novel inhibitor. Biochem. J., 338, 479-487 (1999) 
    21. Joyce, C. W., Shelness, G. S., Davis, M. A., Lee, R. G., Skinner, K., Anderson, R. A., and Rudel, L. L., ACAT1 and ACAT2 membrane topology segregates a serine residue essential for activity to opposite sides of the endopasmic reticulum membrane. Mol. Biol. Cell, 11, 3675-3687 (2000) 
    22. Thirkettle, J., Alvarez, E., Boyd, H., Brown, M., Diez, E., Hueso, J., Elson, S., Fulston, M., Gershater, C., Morata, M. L., Perez, P., Ready, S., Sanchez-Puelles, J. M., Sheridan, R., Stefanska, A., and Warr, S., SB-253514 and analogues; novel inhibitors of lipoprotein-associated phospholipase A2 produced by Pseudomonas fluorescens DSM 11579. I. Fermentation of producing strain, isolation and biological activity. J. Antibiot., 53, 664-669 (2000) 
    23. Blackie, J. A., Bloomer, J. C., Brown, M. J. B., Cheng, H. Y., Hammond, B., Hickey, D. M. B., Ife, R. J., Leach, C. A., Lewis, V. A., Macphee, C. H., Milliner, K. J., Moores, K. E., Pinto, I. L., Smith, S. A., Stansfield, I. G., Stanway, S. J., Taylor, M. A., and Theobald, C. J., The identification of clinical candidate SB-480848: a potent inhibitor of lipoprotein-associated phospholipase A2. Bioorg. Med. Chem. Lett., 13, 1067-1070 (2003) 
    24. Brecher, P. and Chan, C. T., Properties of acyl-CoA:Cholesterol O-acyltransferase in aortic microsomes from atherosclerotic rabbits. Biochem. Biophys. Acta, 617, 458-471 (1980) 
    25. Roth, B. D., Blankley, J., and Hoefle, M. L., Inhibitors of acyl- CoA:cholesterol acyltransferase. 1. Identification and structureactivity relationships of a novel series of fatty acid anilide hypocholesterolemic agents. J. Med. Chem., 35, 1609-1617 (1992) 
    26. Stafforini, D. M., Elstad, M. R., Mclntyre, T. M., Zimmerman, G. A., and Prescott, S. M., Human macrophages secret plateletactivating factor acetylhydrolase. J. Biol. Chem., 265, 9682- 9687 (1990) 
    27. Oh, H. C., Kang, D. G., Lee, S. Y., and Lee, H. S., Angiotensin converting enzyme inhibitors from Cuscuta japonica choisy. J. Ethnopharmacol., 83, 105-108 (2002) 
    28. Jeong, T. S., Kim, S. U., Son, K. H., Kwon, B. M., Kim, Y. K., Choi, M. U., and Bok, S. H., GERI-BP001 compounds, new inhibitors of acyl-CoA: Cholesterol acytransferase from Aspergillus fumigatus F37. J. Antibiot., 48, 751-756 (1995) 
  • 이 논문을 인용한 문헌 (6)

    1. 2006. "" 韓國藥用作物學會誌 = Korean journal of medicinal crop science, 14(5): 273~277     
    2. 2006. "" Archives of pharmacal research : a publication of the Pharmaceutical Society of Korea, 29(3): 191~194     
    3. 2007. "" Archives of pharmacal research : a publication of the Pharmaceutical Society of Korea, 30(11): 1392~1397     
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  • 정성제 (15)

  • Chung, In-Sik (52)

  • 이윤형 (24)

  • Kim, Dae-Keun (128)

  • Kwon, Byoung-Mog (27)

  • Jeong, Tae-Sook (15)

  • 백남인 (142)

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