Nitric oxide inhibitory daphnane diterpenoids as potential anti-neuroinflammatory agents for AD from the twigs of Trigonostemon thyrsoideus

Feng Liu; Xueyuan Yang; Jun Ma; Yuling Yang; Chunfeng Xie; Muhetaer Tuerhong; Da Qing Jin; Jing Xu; Dongho Lee; Yasushi Ohizumi; Yuanqiang Guo

doi:10.1016/j.bioorg.2017.09.007

Nitric oxide inhibitory daphnane diterpenoids as potential anti-neuroinflammatory agents for AD from the twigs of Trigonostemon thyrsoideus

Feng Liu, Xueyuan Yang, Jun Ma, Yuling Yang, Chunfeng Xie, Muhetaer Tuerhong, Da Qing Jin, Jing Xu, Dongho Lee, Yasushi Ohizumi, Yuanqiang Guo

Research output: Contribution to journal › Article › peer-review

40 Citations (Scopus)

Abstract

The extensive pathology studies revealed that Alzheimer's disease (AD) is closely related to neuroinflammation and anti-neuroinflammatory agents may be potentially useful for the treatment of AD. A continuous search for new nitric oxide (NO) inhibitory compounds as anti-neuroinflammatory agents for AD resulted in the isolation of four new (1−4) and eight known (5−12) daphnane diterpenoids from the twigs of Trigonostemon thyrsoideus. Their structures were elucidated on the basis of extensive nuclear magnetic resonance (NMR) spectroscopic data analysis and the time-dependent density functional theory (TDDFT) electronic circular dichroism (ECD) calculations. Compounds 1–4 represent new examples of daphnane diterpenoid orthoesters and 4 features a rare and complex macroring diterpenoid structure. The anti-neuroinflammatory effects were examined by inhibiting NO release in lipopolysaccharide (LPS)-induced murine microglial BV-2 cells. The possible mechanism of NO inhibition of some bioactive compounds was also investigated using molecular docking, which revealed the interactions of bioactive compounds with the inducible nitric oxide synthase (iNOS) protein.

Original language	English
Pages (from-to)	149-156
Number of pages	8
Journal	Bioorganic Chemistry
Volume	75
DOIs	https://doi.org/10.1016/j.bioorg.2017.09.007
Publication status	Published - 2017 Dec

Bibliographical note

Funding Information:
This work was supported by the National Natural Science Foundation of China (Nos. 21372125 and 21642016 ), the Natural Science Foundation of Tianjin, China (No. 16JCYBJC27700 ), the Fundamental Research Funds for the Central Universities , Hundred Young Academic Leaders Program of Nankai University , and the State Key Laboratory of Medicinal Chemical Biology (No. 201602007 ).

Publisher Copyright:
© 2017 Elsevier Inc.

Keywords

Anti-neuroinflammatory
Daphnane diterpenoids
Molecular docking
NO inhibitors
Trigonostemon thyrsoideus

ASJC Scopus subject areas

Biochemistry
Molecular Biology
Drug Discovery
Organic Chemistry

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10.1016/j.bioorg.2017.09.007

Cite this

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title = "Nitric oxide inhibitory daphnane diterpenoids as potential anti-neuroinflammatory agents for AD from the twigs of Trigonostemon thyrsoideus",

abstract = "The extensive pathology studies revealed that Alzheimer's disease (AD) is closely related to neuroinflammation and anti-neuroinflammatory agents may be potentially useful for the treatment of AD. A continuous search for new nitric oxide (NO) inhibitory compounds as anti-neuroinflammatory agents for AD resulted in the isolation of four new (1−4) and eight known (5−12) daphnane diterpenoids from the twigs of Trigonostemon thyrsoideus. Their structures were elucidated on the basis of extensive nuclear magnetic resonance (NMR) spectroscopic data analysis and the time-dependent density functional theory (TDDFT) electronic circular dichroism (ECD) calculations. Compounds 1–4 represent new examples of daphnane diterpenoid orthoesters and 4 features a rare and complex macroring diterpenoid structure. The anti-neuroinflammatory effects were examined by inhibiting NO release in lipopolysaccharide (LPS)-induced murine microglial BV-2 cells. The possible mechanism of NO inhibition of some bioactive compounds was also investigated using molecular docking, which revealed the interactions of bioactive compounds with the inducible nitric oxide synthase (iNOS) protein.",

keywords = "Anti-neuroinflammatory, Daphnane diterpenoids, Molecular docking, NO inhibitors, Trigonostemon thyrsoideus",

author = "Feng Liu and Xueyuan Yang and Jun Ma and Yuling Yang and Chunfeng Xie and Muhetaer Tuerhong and Jin, {Da Qing} and Jing Xu and Dongho Lee and Yasushi Ohizumi and Yuanqiang Guo",

note = "Funding Information: This work was supported by the National Natural Science Foundation of China (Nos. 21372125 and 21642016 ), the Natural Science Foundation of Tianjin, China (No. 16JCYBJC27700 ), the Fundamental Research Funds for the Central Universities , Hundred Young Academic Leaders Program of Nankai University , and the State Key Laboratory of Medicinal Chemical Biology (No. 201602007 ). Publisher Copyright: {\textcopyright} 2017 Elsevier Inc.",

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doi = "10.1016/j.bioorg.2017.09.007",

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AU - Yang, Yuling

AU - Xie, Chunfeng

AU - Tuerhong, Muhetaer

AU - Jin, Da Qing

AU - Xu, Jing

AU - Lee, Dongho

AU - Ohizumi, Yasushi

AU - Guo, Yuanqiang

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AB - The extensive pathology studies revealed that Alzheimer's disease (AD) is closely related to neuroinflammation and anti-neuroinflammatory agents may be potentially useful for the treatment of AD. A continuous search for new nitric oxide (NO) inhibitory compounds as anti-neuroinflammatory agents for AD resulted in the isolation of four new (1−4) and eight known (5−12) daphnane diterpenoids from the twigs of Trigonostemon thyrsoideus. Their structures were elucidated on the basis of extensive nuclear magnetic resonance (NMR) spectroscopic data analysis and the time-dependent density functional theory (TDDFT) electronic circular dichroism (ECD) calculations. Compounds 1–4 represent new examples of daphnane diterpenoid orthoesters and 4 features a rare and complex macroring diterpenoid structure. The anti-neuroinflammatory effects were examined by inhibiting NO release in lipopolysaccharide (LPS)-induced murine microglial BV-2 cells. The possible mechanism of NO inhibition of some bioactive compounds was also investigated using molecular docking, which revealed the interactions of bioactive compounds with the inducible nitric oxide synthase (iNOS) protein.

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Nitric oxide inhibitory daphnane diterpenoids as potential anti-neuroinflammatory agents for AD from the twigs of Trigonostemon thyrsoideus

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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