2. Academic Validation
  3. Nine pairs of megastigmane enantiomers from the leaves of Eucommia ulmoides Oliver

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

  • J Nat Med. 2017 Oct;71(4):780-790. doi: 10.1007/s11418-017-1102-9.
Jiankun Yan 1 2 3,  Xuliu Shi 1 2,  Paul Owusu Donkor 1 2,  Huajie Zhu 4,  Xiumei Gao 2,  Liqin Ding 5,  Feng Qiu 6 7
Affiliations

Affiliations

  • 1 School of Chinese Materia Medica, Tianjin University of Traditional Chinese Medicine, Tianjin, 300193, People's Republic of China.
  • 2 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.
  • 3 Department of Natural Products Chemistry, School of Traditional Chinese Materia Medica, Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, 110016, People's Republic of China.
  • 4 College of Pharmacy, Hebei University, Baoding, 071002, People's Republic of China.
  • 5 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. ruby70303@163.com.
  • 6 School of Chinese Materia Medica, Tianjin University of Traditional Chinese Medicine, Tianjin, 300193, People's Republic of China. fengqiu20070118@163.com.
  • 7 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. fengqiu20070118@163.com.
PMID: 28634927 DOI: 10.1007/s11418-017-1102-9
Abstract

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 (AT1R).

Keywords

Absolute configuration; CDOCKER; ECD; Leaves of Eucommia ulmoides Oliver; Megastigmane enantiomers; OR; Virtual screening.

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