Journal of Environmental Science International (한국환경과학회지)

The Korean Environmental Sciences Society (한국환경과학회)
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Isolation of Guaianolides with ACAT Inhibitory Activity from the Leaves and Stems of Chrysanthemum boreale Makino

산국의 잎과 줄기에서 ACAT 저해활성을 가지는 Guaianolides의 분리

  • Lee, Jong Rok (Department of Pharmaceutical Engineering, Daegu Haany University) ;
  • Park, Moon Ki (Department of Pharmaceutical Engineering, Daegu Haany University)
  • 이종록 (대구한의대학교 제약공학과) ;
  • 박문기 (대구한의대학교 제약공학과)
  • Received : 2017.10.12
  • Accepted : 2017.11.27
  • Published : 2017.11.30
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Abstract

Acyltransferase (AT) catalyzes the transfer of an acyl moiety from acyl-coenzyme A (acyl-CoA) to an acceptor. ATs play important roles in the maintenance of homeostasis in the human body and have been linked to various diseases; therefore, several ATs have been proposed as potential targets for the treatment or prevention of such diseases. The AT family includes acyl-CoA:cholesterol AT (ACAT), diacylglycerol AT, and monoacylglycerol AT for the metabolism of lipids. Furthermore, recent molecular biological studies revealed the existence of their isozymes with distinct functions in the body. ACAT plays a critical role in the formation of cholesteryl esters from cholesterol and fatty acids, and is a potential target for treating hypercholesterolemia. During an experiment designed to discover biologically active compounds from herbal medicines, we isolated two known guaianolide sesquiterpene lactones from Chrysanthemum boreale Makino (Compositae). The lactones were characterized from their spectroscopic data (NMR, IR, MASS). These compounds were subjected to ACAT inhibition assay. Here, we report the isolation and structural elucidation of the compounds 8-o-acetyl-2-methoxy-10-hydroxy-3,11(13)-guaiadiene-12,6-olide and 8-acetyl-3,10-hydroxy-4(15),11(13)-guaiadiene-12,6-olide. In the ACAT inhibition assay, compound 1 showed strong inhibitory activity, with an $IC_{50}$ value $45{\mu}g/mL$, whereas compound 2 did not exhibit significant inhibitory activity with an over $100{\mu}g/mL$.

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References

  1. Barton, D. H., Nayaranan, R., 1958, J. Chem. Soc.(Lond.), 936-971.
  2. Charlwood, B. V., Banthorpe, D. V., 1991, Terpenoids in methods in plant biochemistry, in: Dey, P. M., Harborne, J. B. (eds.), Academic Press, London, 7, 187-211.
  3. Chatterjee, A., Sarkar, S., Saha, S. K., 1982, Acacetin 7-o-${\beta}$-D-galactopyranoside from Chrysanthemum indicum,Phytochemistry, 20, 1760-1761.
  4. Dan, B., Andrew, G., 1986, Chinese herbal medicine, Eastland Press, Seattle, 59.
  5. Ericson, S. K., Shrewbery, M. A., Brooks, C., Meyer, D. J., 1980, Rat liver acyl-coenzyme A : cholesterol acyltransferase : its regulation in vivo and some of its properties in vitro, J. Lipid Res., 21, 930-941.
  6. Fraga, B. M., 1986, Natural sesquiterpenoids, Natural Product Reports, 3, 473-498.
  7. Gtordano, O. S., Querreiro, E., Pestchanker, M. J., Guzman, J., Pastor, D., Guardia, T., 1990, The gastric cytoprotective effect of several sesquiterpene lactones, J. Natural Products, 53(4), 803-809. https://doi.org/10.1021/np50070a004
  8. Hoffmann, H. M. R., Rabe, J., 1985, Synthesis and biological activity of ${\alpha}$-Methylene-${\gamma}$-butyrolactones, Angew. Chem. Int. Ed. Engl., 24, 94-110. https://doi.org/10.1002/anie.198500941
  9. Jang, D. S., Park, K. H., Yang, M. S., 1998, Germacranolides from flowers of Chrysanthemum boreale Makino, Kor. J. Pharmacogn., 29(2), 67-70.
  10. Kim, Y. K., 1996, Research of new material(in Korean), FreeAcademy, 229-240.
  11. McGinley, K. J., Leyden, J. J., Marples, R. R., 1979, Quantitative microbiology of the scalp in non-dandruff, dandruff and seborrheic dermatitis, J. Invest. Dermatol., 64, 401-405.
  12. Sliskovic, D. R., White, A. D., 1991, Therapeutic potential of ACAT inhibitors as lipid lowering and antiatherosclerotic agents, Trends in Pharmacol. Sci., 12, 194-199. https://doi.org/10.1016/0165-6147(91)90546-5
  13. Sporel, J., Becker, H., Allen, N. S., Gupta, M. P., 1991, Spiroterpenoids from Plagiochila moritziana, Phytochemistry, 30(9), 3043-3047. https://doi.org/10.1016/S0031-9422(00)98249-9