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Haperforatones A-M, thirteen undescribed limonoids from Harrisonia perforata with anti-inflammatory activity

文献类型：期刊论文

作者Wang, Qing3,4; Wu, Zhitao3,4; Li, Chenyue2,3; Qin, Guoqing1,3; Hu, Xianggang3,4; Guo, Pengju2,3; Ding, Aoxue1,3; Xu, Wenjing3,4; Wang, Wenqiong1,3; Xuan, Lijiang1,3,4
刊名BIOORGANIC CHEMISTRY
出版日期2024-10-01
卷号151页码:14
关键词Harrisonia perforata UPLC-Q-TOF-MS Mass Defect Filtering Limonoids NO inhibitors Molecular docking Anti-inflammatory
ISSN号0045-2068
DOI10.1016/j.bioorg.2024.107631
通讯作者Wang, Wenqiong(wenqiong1019@simm.ac.cn) ; Xuan, Lijiang(ljxuan@simm.ac.cn)
英文摘要UPLC-Q-TOF-MS combined with mass defect filtering strategies were applied for the phytochemical investigation of Harrisonia perforata, leading to the isolation of thirteen undescribed limonoids named haperforatones A-M (1-13) and seventeen known compounds (14-30). Particularly, haperforatones D-E (4-5) have an unprecedented A, B, C, D-seco-6, 7-nor-C-24-limonoid skeleton, structurally stripped of the five-membered lactone ring B and formed a double bond at the C-5 and C-10 positions. Their 2D structures and relative configurations were identified using spectroscopic data. The absolute configurations of 1, 4, and 6 were established via X-ray diffraction crystallography. All 30 compounds were evaluated for anti-inflammatory potential in LPS-induced Raw 264.7 cell lines. Among those tested compounds, the most potent activity against LPS-induced NO generation was demonstrated by haperforatone F (6), with the IC50 value of inhibition NO production of 7.2 mu M. Additionally, 6 could significantly inhibit IL-1 beta and IL-6 release and markedly downregulate the protein expression level of iNOS in the LPS-stimulated RAW264.7 cells at 10 mu M. The possible mechanism of NO inhibition of 6 was also investigated using molecular docking, which revealed the interaction of compound 6 with the iNOS protein.
WOS关键词PROMISING BIOLOGICAL-ACTIVITY ; REARRANGED LIMONOIDS ; CHROMONES ; QUASSINOIDS
资助项目State Key Laboratory of Drug Research[SIMM1601ZZ-03] ; National Natural Science Foundation of China[82373746] ; Shanghai Municipal Sci- ence and Technology Major Project[TM202301L001]
WOS研究方向Biochemistry & Molecular Biology ; Chemistry
语种英语
WOS记录号WOS:001273301600001
出版者ACADEMIC PRESS INC ELSEVIER SCIENCE
源URL[http://119.78.100.183/handle/2S10ELR8/312514]  
专题新药研究国家重点实验室
通讯作者Wang, Wenqiong; Xuan, Lijiang
作者单位1.Univ Chinese Acad Sci, 19A Yuquan Rd, Beijing 100049, Peoples R China
2.Fudan Univ, Sch Pharm, Shanghai 201203, Peoples R China
3.Chinese Acad Sci, State Key Lab Drug Res, Shanghai Inst Mat Med, 501 Haike Rd, Shanghai 201203, Peoples R China
4.Nanjing Univ Chinese Med, Sch Chinese Mat Med, Nanjing 210023, Peoples R China
推荐引用方式
GB/T 7714		 Wang, Qing,Wu, Zhitao,Li, Chenyue,et al. Haperforatones A-M, thirteen undescribed limonoids from Harrisonia perforata with anti-inflammatory activity[J]. BIOORGANIC CHEMISTRY,2024,151:14.
APA Wang, Qing.,Wu, Zhitao.,Li, Chenyue.,Qin, Guoqing.,Hu, Xianggang.,...&Xuan, Lijiang.(2024).Haperforatones A-M, thirteen undescribed limonoids from Harrisonia perforata with anti-inflammatory activity.BIOORGANIC CHEMISTRY,151,14.
MLA Wang, Qing,et al."Haperforatones A-M, thirteen undescribed limonoids from Harrisonia perforata with anti-inflammatory activity".BIOORGANIC CHEMISTRY 151(2024):14.

入库方式： OAI收割

来源：上海药物研究所

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