Synthesis of Hydroxyrutaecarpine

• Main Authors: Chang-Hsin Lee, 李常新
• Other Authors: Hsi-Jung Yu
• Format: Others
• Language: zh-TW
• Published: 2003
• Online Access: http://ndltd.ncl.edu.tw/handle/97275080108711632048

碩士 === 中國文化大學 === 應用化學研究所 === 91 === The dried fruit of Evodia rutaecarpa has been used in traditional Chinese medicine for the treatment of headache, gastrointestinal disorders, and dysentery. Rutaecarpine, evodiamine, and dehydroevodiamine were three main quinazolinocarboline alkaloids isolated from the fruit of Evodia rutaecarpa. In earlier reports, rutaecarpine was reported to possess a variety of pharmacological effects including antithrombotic, vasorelaxant and antiinflammatory activities. In previous study, rutaecarpine was oxidized by microsomal enzymes to form four hydroxyrutaecarpines. In order to identify these four metabolites from rutaecarpine oxidation, eight possible hydroxyrutaecarpines were synthesized. Two methods were used for preparation of hydroxyrutaecarpines. The first method was followed the literature procedure reported by Bergman, and methoxytryptamines and isatoic anhydride were used as starting materials to yield 9-, 10-, 11-, and 12-methoxyrutaecarpines (CL09a-CL09d). 1,2,3,4-Tetrahydro--carboline-1-one and methoxyanthranilic acids were used in the second method as starting materials to yield 1-, 2-, 3-, and 4-methoxyrutaecarpine (CL09e-CL09h). Methoxyrutaecarpines (CL09a-CL09h) were treated with boron tribromide to form hydroxyrutaecarpines (CL10a-CL10h). By comparison of 1H-NMR spectra of four metabolites with 1H-NMR spectra of eight hydroxyrutaecarpines, we found that four rutaecarpine oxidative metabolites might be 3-, 10-, 11, and 12-hydroxyrutaecarpine.