1. Hyperterpenoids A and B: Two pairs of unprecedented 6/6/4/6/6 polycyclic cyclobutane meroterpenoids with potent neuroprotective and anti-inflammatory activities from Hypericum beanii
- Author
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Jian-Dong Jiang, Jia-Jia Wang, Wei-Ping Wang, Xin-Yue Suo, Bo Zhen, Teng-Fei Ji, Li Li, Ming-Bao Lin, Qi Hou, Yanduo Tao, Jun Dang, Huilan Yue, and Xiaoliang Wang
- Subjects
Preparative hplc ,medicine.drug_class ,Stereochemistry ,Chemistry ,Diastereomer ,02 engineering and technology ,General Chemistry ,010402 general chemistry ,021001 nanoscience & nanotechnology ,01 natural sciences ,Neuroprotection ,Anti-inflammatory ,0104 chemical sciences ,Cyclobutane ,chemistry.chemical_compound ,Hypericum beanii ,medicine ,Structure–activity relationship ,Enantiomer ,0210 nano-technology - Abstract
Hyperterpenoid A (1) and B (2), two pairs of enantiomers, with an unprecedented 6/6/4/6/6 polycyclic skeleton, along with one known compoud hypermonone A (3) were isolated from Hypericum beanii. The racemate (±)-1 and (±)-2 were successfully separated into the two optically pure enantiomers (ee ≥ 99%) using a preparative HPLC system. Their absolute configurations were elucidated by extensive spectroscopic analyses and single-crystal X-ray diffraction method. The related plausible biogenetic pathways were presented. Compound 1-3 showed significant neuroprotective activity and potential anti-inflammatory activity. The result that (+)-2 and (-)-2 presented different anti-inflammatory properties, may lead us to new discovery of structure activity relationship between racemates, enantiomers, and diastereomers, as well as further research regarding the binding of drugs to target proteins.
- Published
- 2021
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