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Chinese Chemical Letters 2024年第3期35卷 415-418页

作者： Chunyang Zhang Yuelan Li Zhaojun Chu Shuangzhi Yuan Yanan Qiao Jiaozhen Zhang Lin Li Yueqing Zhang Ruifeng Tian Yajie Tang Hongxiang Lou Department of Natural Products Chemistry Key Lab of Chemical Biology(MOE)School of Pharmaceutical SciencesShandong UniversityJi'nan 250012China State Key Laboratory of Microbial Technology Shandong UniversityQingdao 266237China

Two distinctive rearranged 19-nor-7,8-seco-labdane diterpenoids(1 and 2)with a novel tetracyclo[5.***.1.0^(2,5.)0^(4,10)]decane skeleton,a derivative of the open tetrahydrofuran ring(7),three dimeric compounds(8-10),and four revised homologs(3-6)were obtained from Chinese liverwort Pallavicinia ambigua.Their structures were identified via combined analysis of their spectroscopic data,single-crystal X-ray diffraction patterns,and ECD calculations.The light-driven conversion of compound 5 to compounds 1-4 demonstrated that photochemically induced postmodification involved in biosynthesis is an important way to diversify natural structures.A preliminary cytotoxicity assay revealed that compound 5 showed significant inhibition in the human prostate cancer(PC-3)cell line via an apoptotic pathway.

关键词： Liverwort Pallavicinia ambigua 19-nor-7 8-seco-Labdan diterpenoid Photoinduced rearrangement cytotoxic activity

β-Carboline alkaloids from the roots of Peganum harmala L.

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Chinese Journal of Natural Medicines 2024年第2期22卷 171-177页

作者： LI Shengge ZHANG Qin WANG Yuetong LIN Bin LI Dahong HUA Huiming HU Xu Henan Key Laboratory of Zhang Zhongjing Formulate and Herbs for Immunoregulation Zhang Zhongjing Traditional School of Chinese MedicineNanyang Institute of TechnologyNanyang 473004China Key Laboratory of Structure-Based Drug Design&Discovery Ministry of EducationShenyang Pharmaceutical UniversityShenyang 110016China Wuya College of Innovation Shenyang Pharmaceutical UniversityShenyang 110016China School of Pharmaceutical Engineering Shenyang Pharmaceutical UniversityShenyang 110016China

This study reports the isolation of four newβ-carboline alkaloids(1−4)and six previously identified alkaloids(5−10)from the roots of Peganum harmala L.Among these compounds,1 and 2 were characterized as rareβ-carboline-quinazoline dimers exhibiting axial chirality.Compound 3 possessed a unique 6/5/6/7 tetracyclic ring system with an azepine ring,and compound 4 was a novel annomontineβ-carboline.The structures of these compounds were elucidated by spectroscopic data and quantum mechanical calculations.The biosynthetic pathways of 1−3 were proposed.Additionally,the cytotoxicity of some isolates against four cancer cell lines(HL-60,A549,MDA-MB-231,and DU145)was evaluated.Notably,compound 4 exhibited significant cytotoxicity against HL-60,A549,and DU145 cells with IC_(50) values of 12.39,12.80,and 30.65μmol·L^(−1),respectively.Furthermore,compound 2 demonstrated selective cytotoxicity against HL-60 cells with an IC_(50) value of 17.32μmol·L^(−1).

关键词： β-Carboline alkaloids Peganum harmala Structure elucidation cytotoxic activity

Rearranged Dichapetalin-Type Triterpenoids with cytotoxic activity from Dichapetalum gelonioides

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Chinese Journal of Chemistry 2022年第21期40卷 2531-2538页

作者： Xin-Hua Gao Xi-Yuan Wang Jun-Su Zhou Yan Zhang Hong-Chun Liu Bin Zhou Jian-Min Yue State Key Laboratory of Drug Research Shanghai lnstitute of Materia MedicaChinese Academy of SciencesShanghai 201203China Research Units of Discovery of New Drug Lead Molecules Chinese Academy of Medical SciencesShanghai 201203china Shandong Laboratory of Yantai Drug Discovery Bohai Rim Advanced Research Institute for Drug DiscoveryYantaiShandong 264117China

Dichagelinoids A—C(1—3),three unusual dichapetalin-type triterpenoids,together with two biogenetically related derivatives dichagelinoids D and E(4 and 5)were isolated and characterized by solid data from Dichapetalum gelonioides.Compounds 1—3 possess a common rearranged C ring and different C6—C2 modified motifs at the A rings.Biological evaluation revealed that compounds 1—3 showed distinct cytotoxic activity against the tested human cancer cell lines.

关键词： Dichapetalum gelonioides Natural products Dichapetalin-type triterpenoids Structural elucidation cytotoxic activity

Distachydrimanes A-F,phenylspirodrimane dimers and hybrids with cytotoxic activity from the coral-derived fungus Stachybotrys chartarum

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Chinese Chemical Letters 2022年第10期33卷 4587-4594页

作者： Shuang Lin Jianzheng Huang Hanxiao Zeng Qingyi Tong Xueke Zhang Beiye Yang Ying Ye Jianping Wang Zhengxi Hu Yonghui Zhang Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation School of PharmacyTongji Medical CollegeHuazhong University of Science and TechnologyWuhan 430030China

By integrating one strain-many compounds(OSMAC)and LC-MS-based molecular networking strategies,distachydrimanes A-F(1-6),six novel phenylspirodrimane dimers and hybrids representing two types of unprecedented terpenoid-polyketide hybrid skeletons,were isolated from the modified fermented rice substrate of a coral-derived fungus Stachybotrys chartarum.All the structures incorporating their absolute configurations were elucidated based on comprehensive spectroscopic analyses,mainly including HRESIMS and NMR data,single-crystal X-ray diffraction(Cu Kα),and comparison of the experimental electronic circular dichroism(ECD)data.Architecturally,compounds 1-6 represent an unprecedented class of dimeric phenylspirodrimanes with an unexpected C-18-C-23′linkage,of which compounds 1-3 also feature an unexpected 5-methyl-1,3-benzenediol moiety via a carbon-carbon linkage.The bioactivity assay demonstrated that compounds 1,5 and 6 induced cell proliferation inhibition,G0/G1 cell cycle arrest,senescence and mitochondrial-mediated apoptosis in L1210 cells,highlighting their potentials as a new category of anticancer agents.

关键词： Stachybotrys chartarum Distachydrimanes A-F Structure elucidation cytotoxic activity Mechanism of action

cytotoxic activity and DNA binding of naphthalimide derivatives with amino acid and dichloroacetamide functionalizations

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Chinese Chemical Letters 2014年第7期25卷 1087-1093页

作者： Ke-Rang Wang Feng Qian Xiao-Man Wang Guan-Hai Tan Rui-Xue Rong Zhi-Ran Cao Hua Chen Ping-Zhu Zhang Xiao-Liu Li Key Laboratory of Chemical Biology of Hebei Province College of Chemistry and Environmental ScienceHebei University Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education Hebei University Department of Immunology School of Basic Medical ScienceHebei University

A series of novel naphthalimide derivatives modified by amino acids and their dichloroacetamide derivatives at the 3-position have been synthesized. Their cytotoxic activities were preliminarily evaluated against He/a, A549 and K562 cells, which showed that the length of the side chains of the amino acids influenced the cytotoxic activities. Moreover, compound 7d showed a very good cytotoxic activity against A549 cells with an IC50 value of 4.78 μmol L-1, Furthermore, the UV-vis, fluorescence, and circular dichroism （CD） spectroscopies and thermal denaturation experiment indicated that compounds 6a, 6d and 7a, 7d, as DNA intercalators, exhibited binding affinities with calf-thymus DNA （Ct-DNA）.

关键词： Naphthalimide Dichloroacetamide cytotoxic activity DNA binding

Synthesis and cytotoxic activity of 3, 4, 11-trihydroxyl modified derivatives of bergenin

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Chinese Journal of Natural Medicines 2014年第12期12卷 929-936页

作者： YAN De-Biao ZHANG Dong-Ping LI Ming LIU Wen-Yuan FENG Feng DI Bin GUO Qing-Long XIE Ning Department of Natural Medicinal Chemistry China Pharmaceutical University Department of Pharmaceutical Analysis China Pharmaceutical University Key Laboratory of Drug Quality Control and Pharmacovigilance Ministry of Education China Pharmaceutical University Jiangsu Key Laboratory of Carcinogenesis and Intervention China Pharmaceutical University Jiangxi Qingfeng Pharmaceutical Ltd.

To synthesize a series of 3-, 4-, and/or 11-trihydroxy modified bergenin derivatives and evaluated their cytotoxic activity in vitro. The phenolic hydroxyl groups of bergenin were protected by benzyl groups with benzyl bromide. Treatment of dibenzyl bergenin with the corresponding acid in the presence of EDC·HCl and DMAP in CH2Cl2, followed by hydrogenation over Pd/C catalysts, afforded derivatives of bergenin esters. All of the target compounds were identified by IR, MS, and 1H NMR. Twenty-six novel and three known derivatives of bergenin esters were synthesized. Their cytotoxicity values were evaluated by the MTT assay on the inhibition of DU-145 and BGC-823 cells in vitro. Several triply-substituted(3a, 4a, 5a, 6a, 7a) and doublysubstituted(8b, 9b) bergenin derivatives exhibited higher cytotoxic activity than bergenin. The result showed that the size of substituents and the lipophilicity of the bergenin esters displayed an important role on their cytotoxic activity.

关键词： Bergenin 3-,4-,and/or 11-trihydroxyl modified derivatives cytotoxic activity Structure-activity relationships

Steroids from the Roots of Asparagus officinalis and Their cytotoxic activity

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Journal of Integrative Plant Biology 2008年第6期50卷 717-722页

作者： Xue-Feng Huang Yu-Ying Lin Ling-Yi Kong Department of Natural Medicinal Chemistry China Pharmaceutical University Nanjing 210009 China

One new （Sarsasapogenin O） and seven known steroids were isolated from the roots of Asparagus offlcinalis L. Their structures were elucidated on the basis of spectroscopic analysis, including various 2D-NMR techniques, hydrolysis, and by comparison of spectral data of known compounds. These compounds together with nine steroids which were previously isolated from this plant, were tested for cytotoxic activity. Among them, eight compounds displayed significant cytotoxiciUes against human A2780, HO-8910, Eca-109, MGC-803, CNE, LTEP-a-2, KB and mouse L1210 tumor cells.

关键词： Asparagus officinalis cytotoxic activity Sarsasapogenin O steroid

Limonoids from seeds of Azadirachta indica A.Juss. and their cytotoxic activity

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Acta Pharmaceutica Sinica B 2018年第4期8卷 639-644页

作者： Jian Chen Xiaona Fan Jianhua Zhu Liyan Song Zhiwei Li Fei Lin Rongmin Yu Hanhong Xu Jiachen Zi Biotechnological Institute of Chinese Materia Medica Jinan University School of Life Sciences Sun Yat-Sen University State Key Laboratory for Conservation and Utilization of Subtropical Agro-Bioresources South China Agricultural University

Four new limonoid-type nortriterpenoids, 1-detigloyl-1-O-methacryloylsalannin(1), 28-deoxo-2,3-dihydronimbolide(2), 12-acetoxy-3-O-acetyl-7-O-tigloylvilasinin(3) and 12-acetoxy-3-Oacetyl-7-O-methacryloylvilasinin(4), along with five known ones, were isolated from seeds of Azadirachta indica A. Juss. Their structures were elucidated by various spectroscopic methods, including UV, IR, MS, NMR, X-ray crystallography, quantum chemical calculation, as well as by comparison of their spectroscopic data with those reported. In the in vitro cytotoxic assay, 2 showed inhibitory activity against human breast cancer MDA-MB-231 cell line with IC_(50) value of 7.68±1.74 μmol/L, and 5 inhibited growth of human cervical cancer Hela cell line, melanoma A375 cell line and promyelocytic leukemia HL-60 cell line, with IC_(50) 12.00±2.08, 17.44±2.11, and 13.95±5.74 μmol/L, respectively.

关键词： Azadirachta indica Nortriterpenoid Limonoid Spectroscopy cytotoxic activity

Anthelmintic, antimicrobial, antioxidant and cytotoxic activity of Caltha palustris var. alba Kashmir, India

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Chinese Journal of Natural Medicines 2014年第8期12卷 567-572页

作者： Sofi Mubashir Mohd Yousuf Dar Bashir A.Lone M.Iqbal Zargar Wajaht A.Shah Department of Chemistry University of Kashmir Centre of Research for Development University of Kashmir Department of Pharmaceutical Sciences University of Kashmir

The methanolic extract obtained from the root portion of Caltha palustris var. alba was evaluated for its anthelmintic efficacy against gastrointestinal nematodes of sheep under both in vitro and in vivo conditions using worm motility inhibition(WMI) assay and fecal egg count reduction(FECR) assay, respectively. The extract was subjected to antimicrobial activity using agar-well diffusion method against different bacterial strains. In addition the extract was evaluated for cytotoxic and antioxidant activity against cultured THP-1(Leukemia), A-549(Lung), HCT-15(Colon), Cervix(HeLa) and PC-3(Prostrate) cell lines by SRB and DPPH radical scavenging assays. The extract used resulted in mean %WMI of 94.44%, as observed when the worms were put in lukewarm buffer for 30 min after exposure to different treatments. The mean mortality index of the sample was 0.95. The lethal concentration(LC50) was 0.11 mg·mL-1. Cell lines were exposed to concentration of 100 μg·mL-1 of extract for 48 h, which reduced the viability of these cell lines. The same plant extract also showed 55.58% DPPH radical scavenging activity.

关键词： Caltha palustris var.alba Anthelmintic activity(in vivo and in vitro) Antimicrobial activity cytotoxic activity Radical scavenging activity

Synthesis, Crystal Structure and cytotoxic activity of a New NAN-190 Analogue

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Chinese Journal of Structural Chemistry 2014年第12期33卷 1773-1778页

作者：陈洪徐未许芳何雪兰袁牧 Pharmaceutical Research Center Guangzhou Medical University

The NAN-190 analogue 2-(2-(2-(4-(2-methoxyphenyl)piperazin-1-yl)ethoxy)ethyl)isoindoline-1,3-dione(1, C23H27N3O4, Mr = 409.48) was synthesized via a three-step reaction and characterized by 1H NMR, 13 C NMR, ESIMS and single-crystal X-ray diffraction. The crystal belongs to orthorhombic, space group Pna21 with a = 7.6445(15), b = 38.851(8), c = 7.1316(14) A, V = 2118.0(7) A3, Z = 4, Dc = 1.2840 mg/mm3, μ = 0.089 mm-1, F(000) = 872.4, R = 0.0545 and w R = 0.1681. The single-crystal X-ray structural analysis reveals that the piperazine ring in compound 1 presents a stable and minimum energy chair conformation. In addition, the preliminary cytotoxic assay shows that the title compound exhibits strong and selective inhibitory activity against DU145 cells(IC50 = 5.88 ± 1.02 μM).

关键词： NAN-190 analogue synthesis crystal structure cytotoxic activity