Nitric oxide inhibitory limonoids as potential anti-neuroinflammatory agents from Swietenia mahagoni

Zhaoyu Shi; Lijun An; Xueyuan Yang; Yaru Xi; Chenyue Zhang; Yuan Shuo; Jie Zhang; Da Qing Jin; Yasushi Ohizumi; Dongho Lee; Jing Xu; Yuanqiang Guo

doi:10.1016/j.bioorg.2018.11.012

Nitric oxide inhibitory limonoids as potential anti-neuroinflammatory agents from Swietenia mahagoni

Zhaoyu Shi, Lijun An, Xueyuan Yang, Yaru Xi, Chenyue Zhang, Yuan Shuo, Jie Zhang, Da Qing Jin, Yasushi Ohizumi, Dongho Lee, Jing Xu, Yuanqiang Guo

Department of Biosystems and Biotechnology

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

6 Citations (Scopus)

Abstract

Recent studies have revealed that there is a close relationship between neuroinflammation and Alzheimer's disease (AD) and compounds with anti-neuroinflammatory effects are potentially useful for the treatment of AD. A phytochemical investigation to obtain new neuroinflammatory inhibitors resulted in the isolation of four new and three known limonoids from Swietenia mahagoni. The structures of these limonoids were established by NMR, MS, and electronic circular dichroism (ECD) data analysis. Compounds 1–3 feature complicated polycyclic caged structures of limonoid orthoester and represent new examples of phragmalin-type limonoids. All of the isolates showed anti-neuroinflammatory activities by inhibiting nitric oxide (NO) release in LPS-induced murine microglial BV-2 cells with compounds 1 and 3–6 having IC ₅₀ values of 26.8, 26.1, 26.0, 37.1, and 16.5 μM, respectively. 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)	177-185
Number of pages	9
Journal	Bioorganic Chemistry
Volume	84
DOIs	https://doi.org/10.1016/j.bioorg.2018.11.012
Publication status	Published - 2019 Mar

Keywords

Anti-neuroinflammatory
Limonoids
Molecular docking
NO inhibitors
Swietenia mahagoni

ASJC Scopus subject areas

Biochemistry
Molecular Biology
Drug Discovery
Organic Chemistry

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10.1016/j.bioorg.2018.11.012

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Nitric oxide inhibitory limonoids as potential anti-neuroinflammatory agents from Swietenia mahagoni. / Shi, Zhaoyu; An, Lijun; Yang, Xueyuan; Xi, Yaru; Zhang, Chenyue; Shuo, Yuan; Zhang, Jie; Jin, Da Qing; Ohizumi, Yasushi; Lee, Dongho; Xu, Jing; Guo, Yuanqiang.

In: Bioorganic Chemistry, Vol. 84, 03.2019, p. 177-185.

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

@article{f065d78462694ff8b4297651d9acd5f2,

title = "Nitric oxide inhibitory limonoids as potential anti-neuroinflammatory agents from Swietenia mahagoni",

abstract = " Recent studies have revealed that there is a close relationship between neuroinflammation and Alzheimer's disease (AD) and compounds with anti-neuroinflammatory effects are potentially useful for the treatment of AD. A phytochemical investigation to obtain new neuroinflammatory inhibitors resulted in the isolation of four new and three known limonoids from Swietenia mahagoni. The structures of these limonoids were established by NMR, MS, and electronic circular dichroism (ECD) data analysis. Compounds 1–3 feature complicated polycyclic caged structures of limonoid orthoester and represent new examples of phragmalin-type limonoids. All of the isolates showed anti-neuroinflammatory activities by inhibiting nitric oxide (NO) release in LPS-induced murine microglial BV-2 cells with compounds 1 and 3–6 having IC 50 values of 26.8, 26.1, 26.0, 37.1, and 16.5 μM, respectively. 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, Limonoids, Molecular docking, NO inhibitors, Swietenia mahagoni",

author = "Zhaoyu Shi and Lijun An and Xueyuan Yang and Yaru Xi and Chenyue Zhang and Yuan Shuo and Jie Zhang and Jin, {Da Qing} and Yasushi Ohizumi and Dongho Lee and Jing Xu and Yuanqiang Guo",

note = "Funding Information: This research was financially supported by the National Key Research and Development Program of China (No. 2018YFA0507204 ), the National Natural Science Foundation of China (Nos. U1703107 , 21642016 , and 21372125 ), the Natural Science Foundation of Tianjin, China (No. 16JCYBJC27700 ), the Hundred Young Academic Leaders Program of Nankai University , and State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources ( Guangxi Normal University , No. CMEMR2018-B02 ). Funding Information: This research was financially supported by the National Key Research and Development Program of China (No. 2018YFA0507204), the National Natural Science Foundation of China (Nos. U1703107, 21642016, and 21372125), the Natural Science Foundation of Tianjin, China (No. 16JCYBJC27700), the Hundred Young Academic Leaders Program of Nankai University, and State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Guangxi Normal University, No. CMEMR2018-B02). Publisher Copyright: {\textcopyright} 2018 Elsevier Inc.",

year = "2019",

month = mar,

doi = "10.1016/j.bioorg.2018.11.012",

language = "English",

volume = "84",

pages = "177--185",

journal = "Bioorganic Chemistry",

issn = "0045-2068",

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AU - Shi, Zhaoyu

AU - An, Lijun

AU - Yang, Xueyuan

AU - Xi, Yaru

AU - Zhang, Chenyue

AU - Shuo, Yuan

AU - Zhang, Jie

AU - Jin, Da Qing

AU - Ohizumi, Yasushi

AU - Lee, Dongho

AU - Xu, Jing

AU - Guo, Yuanqiang

N1 - Funding Information: This research was financially supported by the National Key Research and Development Program of China (No. 2018YFA0507204 ), the National Natural Science Foundation of China (Nos. U1703107 , 21642016 , and 21372125 ), the Natural Science Foundation of Tianjin, China (No. 16JCYBJC27700 ), the Hundred Young Academic Leaders Program of Nankai University , and State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources ( Guangxi Normal University , No. CMEMR2018-B02 ). Funding Information: This research was financially supported by the National Key Research and Development Program of China (No. 2018YFA0507204), the National Natural Science Foundation of China (Nos. U1703107, 21642016, and 21372125), the Natural Science Foundation of Tianjin, China (No. 16JCYBJC27700), the Hundred Young Academic Leaders Program of Nankai University, and State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Guangxi Normal University, No. CMEMR2018-B02). Publisher Copyright: © 2018 Elsevier Inc.

PY - 2019/3

Y1 - 2019/3

N2 - Recent studies have revealed that there is a close relationship between neuroinflammation and Alzheimer's disease (AD) and compounds with anti-neuroinflammatory effects are potentially useful for the treatment of AD. A phytochemical investigation to obtain new neuroinflammatory inhibitors resulted in the isolation of four new and three known limonoids from Swietenia mahagoni. The structures of these limonoids were established by NMR, MS, and electronic circular dichroism (ECD) data analysis. Compounds 1–3 feature complicated polycyclic caged structures of limonoid orthoester and represent new examples of phragmalin-type limonoids. All of the isolates showed anti-neuroinflammatory activities by inhibiting nitric oxide (NO) release in LPS-induced murine microglial BV-2 cells with compounds 1 and 3–6 having IC 50 values of 26.8, 26.1, 26.0, 37.1, and 16.5 μM, respectively. 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.

AB - Recent studies have revealed that there is a close relationship between neuroinflammation and Alzheimer's disease (AD) and compounds with anti-neuroinflammatory effects are potentially useful for the treatment of AD. A phytochemical investigation to obtain new neuroinflammatory inhibitors resulted in the isolation of four new and three known limonoids from Swietenia mahagoni. The structures of these limonoids were established by NMR, MS, and electronic circular dichroism (ECD) data analysis. Compounds 1–3 feature complicated polycyclic caged structures of limonoid orthoester and represent new examples of phragmalin-type limonoids. All of the isolates showed anti-neuroinflammatory activities by inhibiting nitric oxide (NO) release in LPS-induced murine microglial BV-2 cells with compounds 1 and 3–6 having IC 50 values of 26.8, 26.1, 26.0, 37.1, and 16.5 μM, respectively. 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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KW - Limonoids

KW - Molecular docking

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DO - 10.1016/j.bioorg.2018.11.012

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VL - 84

SP - 177

EP - 185

JO - Bioorganic Chemistry

JF - Bioorganic Chemistry

SN - 0045-2068

ER -

Nitric oxide inhibitory limonoids as potential anti-neuroinflammatory agents from Swietenia mahagoni

Abstract

Keywords

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