YAKHAK HOEJI (약학회지)

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

Formation of Methyl 2${\beta},\;3{\beta}$-Epoxy-23-hydroxyurs-12-en-28-oate from Asiaticoside and Its Reductive Epoxide Ring Opening Reaction

아시아티코사이드로부터 메칠 2${\beta},\;3{\beta}$-에폭시-23- 히드록시우르스-12-엔-28-오애이트의 합성 및 이의 환원적 에폭시환 개열반응

  • Published : 1998.10.01
Download PDF
⟨ Previous Next ⟩

Abstract

Steroidal 2${\beta},\;3{\beta}$--epoxy compound was prepared from asiaticoside via six steps and reduced regioselectively with lithium aluminum hydride. Epoxide ring opening furnished 9 as a sole product at reflux condition through axial hydride attack at C-3.

Keywords

References

  1. Bull. Sci. Pharmacol. v.49 A new heteroside, asiaticoside, isolated from Hydrocotyle asiatica L. Bontems, J. E.
  2. Compt. rend. v.228 Chemical constitution of asiaticoside and asiatic acid. Polonsky, J.
  3. Proc. Soc. Exp. Biol. Med. v.125 Effect of asiaticoside on wound healing in the rat. Rosen, H.;Blumenthal, A.;McCallum, J.
  4. Bull. Soc. chim. biol. v.31 Chemical constitution of asiaticoside, a heteroside form-naturally used against leprosy. Boiteau, P.;Buzas, A.;Lederer, E.;Polonsky, J.
  5. Dermatol. v.49 The effect of asiaticoside on gunia pig skin. J. Invest. Lawrence, J. C.
  6. Eur. J. Pharmacol. v.4 The effect of asiaticoside on pig skin in organ culture. Anne, M.
  7. Acta Ther. v.16 Effect of terpenoids isolated from Centella asiatica on granuloma tissue. Vogel, H. G.;De Souza, N. J.;D'Sa, A.
  8. Eur. Pat. Appl. v.EP 383 Preparation of 2,3,23-trihydroxyuro-12-ene and its derivatives as serotonergic receptor antagonists. Souza, D.;John, N.;Virbala, S.;Durgarao, D. P.;Krishnaji, I. P.;Dawoodbhai, L. A.;Shantaram, M. S.;Juergen, B.
  9. Wien. Med. Wochschr. v.114 Treatment of wounds with asiaticoside (madecassol). Kiesswetter. H.
  10. Planta Med. v.60 Influence of asiatic acid, madecassic acid and asiaticoside on human collagen 1 synthesis. Bonte, F.;Dumas, M.;Chaudagne, C.;Meyveck, A.
  11. Eur. J. Drug Metab. Pharmarco. v.18 The comparative steady-state bioavailability of the active ingredients of Madecassol. Rush, W. R.;Murray, G. R.;Graham, D. J. M.
  12. Arzneim.-Forsch. v.21 Metabolism of asiatic acid, madecassic acid and asiaticoside. Chasseaud, L. F.;Fry, B. J.;Hawkins, D. R.;Lewis, J. D.;Sword, I. P.;Taylor, T.;Hathway, D. E.
  13. v.8 Reduction of epoxide, Chapter 4.4 in Comprehensive Organic Synthesis, Trost, S. M., ed. Murai, S.
  14. Phytochemistry v.22 Terpenoids of Rhododendron japonicum. Sakakibara, J. S.;Kaiya, T.
  15. Phytochemistry v.31 Triterpenoids and their glycosides from the bark of Schefflera octophylla. Sung, T. V.;Lavaud, C.;Porzel, A.;Steglich, W.;Adam, G.