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Published in: Journal of Natural Medicines 4/2017

01-10-2017 | Note

Nine pairs of megastigmane enantiomers from the leaves of Eucommia ulmoides Oliver

Authors: Jiankun Yan, Xuliu Shi, Paul Owusu Donkor, Huajie Zhu, Xiumei Gao, Liqin Ding, Feng Qiu

Published in: Journal of Natural Medicines | Issue 4/2017

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Abstract

Nine pairs of megastigmane enantiomers (1a/1b9a/9b), comprising two new compounds (6S,9R)-blumenol C (7b), (6S,9S)-blumenol C (8b), two pairs of enantiomers (+)-(6R)-eucomegastigmane A (1a), (−)-(6S)-eucomegastigmane A (1b), (+)-(3S,4S)-eucomegastigmane B (5a), (−)-(3R,4R)-eucomegastigmane B (5b) isolated by chiral resolution firstly, and twelve known compounds, were isolated from the leaves of Eucommia ulmoides Oliver. Their structures were elucidated based on extensive spectroscopic analysis. Absolute configurations of the megastigmane enantiomers were assigned by comparing experimental ECD and OR with calculated ECD and OR. Docking-based virtual screening of all compounds showed that megastigmane enantiomers have weak intermolecular interactions with the binding site residues of angiotensin-converting enzyme (ACE) and angiotensin II type 1 receptor (AT1R).
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Metadata
Title
Nine pairs of megastigmane enantiomers from the leaves of Eucommia ulmoides Oliver
Authors
Jiankun Yan
Xuliu Shi
Paul Owusu Donkor
Huajie Zhu
Xiumei Gao
Liqin Ding
Feng Qiu
Publication date
01-10-2017
Publisher
Springer Singapore
Published in
Journal of Natural Medicines / Issue 4/2017
Print ISSN: 1340-3443
Electronic ISSN: 1861-0293
DOI
https://doi.org/10.1007/s11418-017-1102-9

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