Iodine-catalyzed etherification of morroniside.
In this study, we describe a highly selective etherification procedure of unprotected morroniside catalyzed by molecular iodine in acetone. The etherification reaction furnished 7-O-alkyl ether derivatives in reasonable yields within few hours under neutral conditions. Studies of the obtained products on cytotoxicity activity in colon 26-L5 cell line were examined. Among the tested compounds, 7-O-dodecylmorroniside showed moderate cytotoxic activity, having IC50 values equal to 20.9 microM.
Sunghwa
Fortunatus
F
Department of Chemistry, Faculty of Science, University of Dar es salaam, Dar es salaam, Tanzania.
Sakurai
Hiroaki
H
Saiki
Ikuo
I
Koketsu
Mamoru
M
D000096:Acetone / Q000737:chemistry; D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000627:therapeutic use; D002384:Catalysis; D045744:Cell Line, Tumor; D003110:Colonic Neoplasms / Q000188:drug therapy; D004987:Ethers / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry* / Q000627:therapeutic use; D007455:Iodine / Q000737:chemistry*; D051379:Mice; D015394:Molecular Structure; D018517:Plant Roots / Q000737:chemistry; D031451:Strychnos / Q000737:chemistry
D000972:Antineoplastic Agents, Phytogenic; D004987:Ethers; D006027:Glycosides; C488401:morroniside; D000096:Acetone; D007455:Iodine