YAKHAK HOEJI (약학회지)

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

Development of an Efficient Synthetic Method for a Novel Anticancer Substance Isolated from Insect-flower

동충하초에서 분리된 신규 항암물질의 효율적 합성법 개발

  • Received : 2012.02.20
  • Accepted : 2012.03.07
  • Published : 2012.04.30
Download PDF
⟨ Previous Next ⟩

Abstract

Cordyceps militaris, a caterpillar-grown traditional medicinal mushroom, produces important bioactive compounds, cordycepin (3'-deoxyadenosine) and militarin. Militarin is reported to possess anticancer activities against several tumor cells. An efficient synthetic method of militarin was developed to prepare muti-gram scale sample for bioassay. Militarin was successfully synthesized from commercial starting materials in 5 steps and 29.3% overall yields.

Keywords

References

  1. Cho, M. A., Lee, D. S., Kim, M. J., Sung, J. M. and Ham, S. S. : Antimutagenecity and cytotoxicity of cordycepin isolated from Cordyceps militaris. Food Sci. Biotechnol. 12, 472 (2003).
  2. Choi, S. B., Park, C. H., Choi, M. K., Jun, D. W. and Park, S. M. : Improvement of insulin resistance and insulin secretion by water extracts of Cordyceps militaris, Phellinus linteus, and Paecilomyces tenuipes in 90% pancreatectomized rats. Biosci. Biotechnol. Biochem. 68, 2257 (2004).
  3. Yoo, H. S., Shin, J. W., Cho, J. H., Son, C. G., Lee, Y. W., Park, S. Y. and Cho, C. K. : Effect of Cordyceps militaris extract on angiogenesis and tumor growth. Acta Pharmacol. Sin. 25, 657 (2004).
  4. Yun, Y. H., Han, S. H., Lee, S. J., Ko, S. K., Lee, C. K., Ha, N. J. and Kim, K. J. : Anti-diabetic effects of CCCA, CMESS and cordycepin from Cordyceps militaris and the immune responses in streptozotocin-induced diabetic mice. Nat. Prod. Sci. 9, 291 (2003).
  5. Chang, W., Lim, S., Song, H., Song, B. W., Kim, H. J., Cha, M. J., Sung, J. M., Kim, T. W. and Hwang, K. C. : Cordycepin inhibits vascular smooth muscle cell proliferation. Eur. J. Pharmacol. 597, 64 (2008).
  6. 김태웅, 주식회사머쉬텍, 성재모 : 밀리타리스동충하초로부터 분리 된 항암활성이 있는 신물질과 그 제조방법 및 용도. 대한민국 등록특허 10-0538311 (2005).
  7. Busch, B. B., Staiger, C. L., Stoddard, J. M. and Kenneth, J. : Living polymerization of sulfur ylides. Synthesis of terminally functionalized and telechelic polymethylene shea. Macromolecules 35, 8330 (2002).
  8. Delamarche, E., Donzel, C., Kamounah, F. S., Wolf, H., Geissler, M., Stutz, R., Schmidt-Winkel, P., Michel, B., Mathieu, H. J. and Schaumburg, K. : Microcontact printing using poly(dimethylsiloxane) stamps hydrophilized by poly(ethylene oxide) silanes. Langmuir 19, 8749 (2003).
  9. Gutierrez-Rodriguez, M., Garcia-Lopez, M. T. and Herranz, R. : Improved synthesis of a [4.4]-spirolactam $\beta$-turn mimetic as surrogate of the didemnin side chain dipeptide Pro-N-Me-DLeu. Tetrahedron 60, 5177 (2004).
  10. Alesso, S. M., Yu, Z., Pears, D., Worthington, P. A., Luke, R. W. A. and Bradley, M. : Improving resins for solid phase synthesis: incorporation of 1-[2-(2-methoxyethoxy)ethoxy] -4- vinylbenzene. Tetrahedron 59, 7163 (2003).