Citation: Bo Zhen, Xinyue Suo, Jun Dang, Huilan Yue, Yanduo Tao, Jia-Jia Wang, Li Li, Ming-Bao Lin, Qi Hou, Wei-Ping Wang, Xiao-Liang Wang, Jian-Dong Jiang, Teng-Fei Ji. 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[J]. Chinese Chemical Letters, ;2021, 32(7): 2338-2341. doi: 10.1016/j.cclet.2020.10.027 shu

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

Bo Zhen ^{a, 1} ,
Xinyue Suo ^{a, 1} ,
Jun Dang ^b ,
Huilan Yue ^b ,
Yanduo Tao ^b ,
Jia-Jia Wang ^a ,
Li Li ^a ,
Ming-Bao Lin ^a ,
Qi Hou ^a ,
Wei-Ping Wang ^a ,
Xiao-Liang Wang ^a ,
Jian-Dong Jiang ^{a, *,} ,
Teng-Fei Ji ^{a, *,}

a.
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
b.
Key Laboratory of Tibetan Medicine Research, Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Xining 810008, China

jiang.jdong@163.com

jitf@imm.ac.cn

Received Date: 16 August 2020
Revised Date: 20 September 2020
Accepted Date: 21 October 2020
Available Online: 22 October 2020

Figures(8)

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.
- Hypericum beanii,
- Meroterpenoids,
- (±)-Hyperterpenoid A and B,
- Anti-inflammatory activity,
- Neuroprotective activity
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