Optical Resolution and Structure Determination of New Indolizidine Alkaloids from Elaeocarpus sphaericus |
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| Authors: | Chang‐Xin Zhou Xue‐Yao Wang Jian‐Xia Mo Jian Zhang Li‐She Gan |
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| Affiliation: | 1. Institute of Modern Chinese Medicine (IMCM), College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, P.?R. China (phone: +86‐571‐88208456;2. fax: +86‐571‐88208457);3. Institute of Medical Science, School of Medicine, Shanghai Jiaotong University, Shanghai 200025, P.?R. China |
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| Abstract: | Two new indolizidine alkaloids, (±)‐3‐oxoisoelaeocarpine ( 1 ) and (±)‐elaeocarpine N‐oxide ( 2 ), along with three known alkaloids, (±)‐isoelaeocarpine ( 3 ), (±)‐elaeocarpine ( 4 ), and (?)‐isoelaeocarpiline ( 5 ), were isolated from an EtOH extract of the branches and leaves of Elaeocarpus sphaericus. The structures of these compounds were determined by spectroscopic and chemical methods. Furthermore, enantiomers of compounds 1 and 3 were separated on a chiral CD‐Ph column, and their absolute configurations were determined by TD‐DFT (=time‐dependent density‐functional theory) quantum‐chemical calculations of their electronic circular dichroism (ECD) spectra. |
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| Keywords: | Elaeocarpus sphaericus Alkaloids Indolizidine alkaloids Isoelaeocarpine, (± )‐3‐oxo‐ (± )‐Elaeocarpine N‐oxide |
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