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Edulisones A and B, two epimeric benzo[b]oxepine derivatives from the bark of Aglaia edulis |
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| Authors: | Soyoung Kim Bao-Ning Su Soedarsono Riswan Leonardus B.S. Kardono Johar J. Afriastini Judith C. Gallucci Heebyung Chai Norman R. Farnsworth Geoffrey A. Cordell Steven M. Swanson A. Douglas Kinghorn |
| Affiliation: | aProgram for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, USA bDivision of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH 43210, USA cHerbarium Bogoriense, Research and Development Center for Biology, Indonesian Institute of Science, 16122 Bogor, Indonesia dResearch and Development Chemistry, Indonesian Institute of Science, Serpong, 15310 Tangerang, Indonesia eDepartment of Chemistry, The Ohio State University, Columbus, OH 43210, USA |
| Abstract: | Two benzo[b]oxepine derivatives, edulisones A (1) and B (2), were isolated from the bark of Aglaia edulis, collected in Indonesia. The relative stereochemistry of 1 was determined by single-crystal X-ray diffraction analysis. Treatment of compounds 1 and 2 with lithium hydroxide produced the same hydrolysis products, 1a and 1b, as a result of cleavage of the pyrrolidine ring to an alkylated amide mixture in each case, which demonstrated that these substances are epimeric at their 2-aminopyrrolidine moiety. |
| Keywords: | Aglaia edulis Meliaceae Edulisones A and B Benzo[b]oxepines Epimers NMR data X-ray analysis Alkaline hydrolysis |
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