Citation: Guo Rui, Lv Tianming, Han Fengying, Hou Zilin, Yao Guodong, Lin Bin, Wang Xiaobo, Huang Xiaoxiao, Song Shaojiang. New norlignan enantiomers from the fruit of Crataegus pinnatifida with neuroprotective activities[J]. Chinese Chemical Letters, ;2020, 31(5): 1254-1258. doi: 10.1016/j.cclet.2019.09.042 shu

New norlignan enantiomers from the fruit of Crataegus pinnatifida with neuroprotective activities

Guo Rui ^a ,
Lv Tianming ^a ,
Han Fengying ^a ,
Hou Zilin ^a ,
Yao Guodong ^a ,
Lin Bin ^b ,
Wang Xiaobo ^c ,
Huang Xiaoxiao ^a,c,*, ,
Song Shaojiang ^a,*,

a.
Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research&Development, Liaoning Province, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China
b.
School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, China
c.
Chinese People's Liberation Army Logistics Support Force No. 967 Hospital, Dalian 116021, China

xiaoxiao270@163.com

songsj99@163.com

Received Date: 10 August 2019
Revised Date: 18 September 2019
Accepted Date: 20 September 2019
Available Online: 20 September 2019

Figures(7)

(±)-Crataegusnorin A (1a/1b) and B (2a/2b), two pairs of rare 8, 9'-epoxy-type norlignan enantiomers featuring a γ-butyrolactone ring, were isolated from the fruit of Crataegus pinnatifida. Their structures were determined via extensive spectroscopic analyses. Gauge-independent atomic orbital (GIAO) NMR chemical shift calculations, combined with the advanced statistical method DP4⁺ were employed to establish the relative configurations of four compounds. Next, chiral separation was accomplished by chiral chromatographic column and the absolute configurations of the four compounds were unambiguously assigned by comparison between their experimental electronic circular dichroism curves with the quantum-mechanically calculated curves based on time-dependent density functional theory (TDDFT). All the isolates were evaluated for their neuroprotective activities against H₂O₂-induced cell injury in human neuroblastoma SH-SY5Y cells. The results showed that two pairs of enantiomers 1a/1b and 2a/2b displayed diff; erent effect on neuroprotective activity. Among them, compound 2a displayed the most potent neuroprotective effect. Further flow cytometry analysis indicated that 2a could protect SH-SY5Y cells from oxidative damage through inhibiting cell apoptosis.
- Crataegus pinnatifida,
- Norlignan enantiomer,
- Neuroprotective activity,
- SH-SY5Y cells,
- Apoptosis
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