Yan Jiankun, Shi Xuliu, Donkor Paul Owusu, Zhu Huajie, Gao Xiumei, Ding Liqin, Qiu Feng
School of Chinese Materia Medica, Tianjin University of Traditional Chinese Medicine, Tianjin, 300193, People's Republic of China.
Tianjin State Key Laboratory of Modern Chinese Medicine, Tianjin University of Traditional Chinese Medicine, #312 Anshanxi Road, Nankai District, Tianjin, 300193, People's Republic of China.
J Nat Med. 2017 Oct;71(4):780-790. doi: 10.1007/s11418-017-1102-9. Epub 2017 Jun 20.
Nine pairs of megastigmane enantiomers (1a/1b-9a/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 (ATR).
从杜仲（Eucommia ulmoides Oliver）叶中分离得到9对巨豆三烯醇对映体（1a/1b - 9a/9b），包括2个新化合物（6S,9R）- 布卢门醇C（7b）、（6S,9S）- 布卢门醇C（8b），2对首次通过手性拆分分离得到的对映体（+）-（6R）- 杜仲巨豆三烯醇A（1a）、（-）-（6S）- 杜仲巨豆三烯醇A（1b），（+）-（3S,4S）- 杜仲巨豆三烯醇B（5a）、（-）-（3R,4R）- 杜仲巨豆三烯醇B（5b），以及12个已知化合物。通过广泛的光谱分析确定了它们的结构。通过比较实验ECD和OR与计算得到的ECD和OR，确定了巨豆三烯醇对映体的绝对构型。基于对接的所有化合物虚拟筛选表明，巨豆三烯醇对映体与血管紧张素转换酶（ACE）和血管紧张素II 1型受体（ATR）的结合位点残基具有弱分子间相互作用。
