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Structurally Diverse Matrine-Based Alkaloids with Anti-inflam-matory Effects from sophora alopecuroides

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Chinese Journal of Chemistry 2021年第12期39卷 3339-3346页

作者： Ding Luo Neng-Hua Chen Wen-Zhi Wang Ji-Hui Zhang Can-Jie Li Xue-Fang Zhuo Zhen-Chao Tu Zhong-Nan Wu Chun-Lin Fan Hai-Peng Zhang Yao-Lan Li Guo-Cai Wang Yu-Bo Zhang Institute of Traditional Chinese Medicine&Natural Products Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs ResearchCollege of PharmacyJinan UniversityGuangzhouGuangdong 510632China Guangdong Clinical Translational Center for Targeted Drug Department of PharmacologySchool of MedicineJinan UniversityGuangzhouGuangdong 510632China

A phytochemical investigation on the seeds of sophora alopecuroides led to obtaining fourteen structurally diverse matrine-based alkaloids(1-14),including eight new ones(1,6,8-12,14).Notably,alopecuroide F(1)represents the first dimeric matrine-type skeleton assembled via unprecedent C-13-C-12'*** new structures were determined through extensive spectroscopic data(UV,OR,HRESIMS,1D,and 2D NMR),ECD calculations,and three instances,verified by X-ray ***,all alkaloids were evaluated for cytotoxicity against four human cancer cell lines(HepG2,A549,THP-1,and MCF-7)and anti-inflammatory activities for two pro-inflammatory cytokines(TNF-αand IL-6).Alopecuroide F(1)can inhibit TNF-αand IL-6 productions in a dose-dependent manner with IC50 values of 35.6±0.5 and 41.7±0.8μmol/L,respectively.

关键词： sophora alopecuroides Alkaloids Structure elucidation Anti-inflammatory activity Biological activitiy Configuration determination

Alopecuroidines A-C, three matrine-derived alkaloids from the seeds of sophora alopecuroides

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Chinese Chemical Letters 2021年第12期32卷 4058-4062页

作者： Xiang Yuan Zhenyuan Li Ziming Feng Jianshuang Jiang Yanan Yang Peicheng Zhang State Key Laboratory of Bioactive Substance and Function of Natural Medicines Institute of Materia MedicaChinese Academy of Medical Sciences and Peking Union Medical CollegeBeijing 100050China

Three matrine-derived alkaloids, alopecuroidine A(1), alopecuroidine B(2 a) and alopecuroidine C(2 b)were isolated from the seeds of sophora alopecuroides. Their structures were elucidated by extensive spectroscopic analyses and X-ray diffraction. Three compounds possess an unprecedented rearranged fused7/6/5/6 tetracyclic skeleton with a diazacycloheptane structure. Their plausible biosynthetic pathway was also proposed. The anti-proliferative activities of compounds 1 and 2 a were examined by the MTT *** 1 inhibited the viability of human lung cancer A549 cells, having a half maximal inhibitory concentration(IC50) of 7.58 ± 2.47 μmol/L at 72 h. The flow cytometric analysis suggested that 1 inhibited A549 cell growth by inducing apoptosis and cell-cycle arrest. Additionally, 1 induced the loss of mitochondrial membrane potential, elevated intracellular reactive oxygen species, increased the Bax/Bcl-2 ratio, stimulated cleaved-caspase-3 and P53 protein levels, and suppressed the pro-caspase-3 level. Thus,1 appeared to induce A549 cells apoptosis through a mitochondria-mediated apoptotic pathway.

关键词： Alkaloids sophora alopecuroides X-ray diffraction Anti-proliferative Apoptosis

Sophaloseedlines A-G: Diverse Matrine-Based Alkaloids from sophora alopecuroides with Potential Anti-Hepatitis B Virus Activities

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Chinese Journal of Chemistry 2021年第9期39卷 2555-2562页

作者： Ding Luo Zhong-Nan Wu Ji-Hui Zhang Qiang Lin Neng-Hua Chen Si Chen Qing Tang Zhao-Chun Zhan Chun-Lin Fan Yao-Lan Li Guo-Cai Wang Yu-Bo Zhang Institute of Traditional Chinese Medicine&Natural Products Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs ResearchCollege of PharmacyJinan UniversityGuangzhouGuangdong 510632China Guangdong Clinical Translational Center for Targeted Drug Department of PharmacologySchool of MedicineJinan UniversityGuangzhouGuangdong 510632China

Sophaloseedlines A-G(1-7),seven new matrine-based alkaloids along with two known analogues,were isolated from the seeds of sophora *** new structures were determined based on extensive spectroscopic data,electronic circular dichroism calculations,and X-ray ***,sophaloseedline A(1)represents a novel rearranged 6(5→17)-abeo-matrine alkaloid featuring unprecedented highly constructed 7/6/5/6 tetracyclic fused ring *** hypothetical biosynthetic pathways for sophaloseedli nes A-F were proposed based on co-existing ***,all the isolated alkaloids were screened for their antiviral activities against hepatitis B virus,and new alkaloids 1 and 2 displayed more potent activities than those of matrine(a parent alkaloid of title plant)and positive control(lamivudine).

关键词： sophora alopecuroides Matrine-based alkaloid Structure elucidation Anti-HBV activity Biological activity

Five quinolizidine alkaloids with anti-tobacco mosaic virus activities from two species of sophora

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Chinese Chemical Letters 2024年第6期35卷 380-384页

作者： Ji Zhang Tong Zhang Qiao An Peng Zhang Cai-Yan Tian Chun-Mao Yuan Ping Yi Zhan-Xing Hu Xiao-Jiang Hao State Key Laboratory of Functions and Applications of Medicinal Plants Guizhou Medical UniversityGuiyang 550014China Natural Products Research Center of Guizhou Province Guiyang 550014China School of Pharmaceutical Sciences Guizhou Medical UniversityGuiyang 550025China School of Pharmacy Guizhou University of Traditional Chinese MedicineGuiyang 550025China State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of ScienceKunming 650201China Research Unit of Chemical Biology of Natural Anti-Virus Products Chinese Academy of Medical SciencesKunming 650201China

Three novel matrine-type alkaloids(1-3)and two unprecedented aloperine-type alkaloids(4 and 5)were isolated from the root of sophora tonkinensis and the seeds of sophora alopecuroides ***,compound 1 possessed an unprecedented 6/5/6 tricyclic skeleton,while compounds 2 and 3 characterized by rare 6/6/5/6 tetracyclic system and 6/6/6/6/6 pentacyclic system ***,compound 4 possessed an unprecedented 6/7/6/6 tetracyclic core,and compound 5 characterized by rare 6/6/6/6tetracyclic *** structures were elucidated by comprehensive spectroscopic data analysis and electronic circular dichroism(ECD)*** tests indicated that compound 5 displayed significant anti-tobacco mosaic virus(TMV)activity compared with the positive control ningnanmycin.

关键词： Matrine-type alkaloids Aloperine-type alkaloids sophora tonkinensis sophora alopecuroides Anti-tobacco mosaic virus

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Chinese Herbal Medicines 2011年第1期3卷 70-74页

作者： ZHAO Wen-chang SONG Li-un School of Pharmacy Guangdong Medical College Dongguan 523808 China

The 3rd International Conference and Exposition on the Modernization of Traditional Chinese Medicine was held during Nov.25-26,2010 in Chengdu(Sichuan,China),editorial director CHEN Chang-qing associated with other me... 详细信息

关键词： alkaloids HPLC-DAD qualitative analysis quantitative analysis sophora alopecuroides

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拮抗性苦豆子内生细菌的遗传多样性(英文)

Plant Diseases and Pests 2011年第4期2卷 6-8,33页

作者：林天兴李超龚明福乐山师范学院化学与生命学院四川乐山634004 新疆生产建设兵团塔里木盆地生物资源保护利用重点实验室塔里木大学生命科学学院新疆阿拉尔843300

[ Objective ] The paper was to study and analyze the genetic diversity of 48 endophytic bacteria isolated from sophora alopecuroide with strong antagonis- tic effect against Fusarium oxysporum and Verticillium dahliae, and carry out sequence measurement and phylogenetic analysis on 10 representative strains. [ Meth- od] Using total DNA ERIC-PCR and 16S rRNA sequencing analysis method, a total of 48 endophytic bacteria were carried out genetic diversity and phylogenetic analysis. [Result] ERIC-PCR fingerprint map showed that 48 endophytic bacteria were divided into 6 ERIC groups and 2 strains with independent groups at Wat- son distance of 0.31. Representative strains were selected from each group to determine 16S rRNA gene for phylogenetic analysis, and the results showed that these strains belonged to Bacillus atrophaeus, Bacillus subtilis, Bacillus cereus, Bacillus megaterium, Bacillus pumilus and Serratia marcescens, respectively. [ Conclu- sion ] The genetic diversity of 48 strains of bacteria was obvious. Determination of 48 strains of bacteria on diversity and phylogenetic status could lay foundation for study on mechanism of F. oxysporum and V. dahliae, which could also provide new strain sources for biological control of diseases in cotton production.

关键词： sophora alopecuroides Endophytic bacteria Diversity Antagonistic China