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Artematrovirenolides A—D and Artematrolides S—Z,Sesquiterpenoid Dimers with Cytotoxicity against Three Hepatoma Cell lines from Artemisia atrovirens

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Chinese Journal of Chemistry 2022年第1期40卷 104-114页

作者： li-hua su Tian-Ze li Yun-Bao Ma Chang-An Geng Xiao-Yan huang Xin Zhang Zhen Gao Ji-Jun Chen State Key Laboratory of Phytochemistry and Plant Resources in West China Yunnan Key Laboratory of Natural Medicinal ChemistryKunming Institute of BotanyChinese Academy of SciencesKunmingYunnan 650201China University of Chinese Academy of Sciences Beijing 100049China

Inspired by the intriguing structures and remarkable activities of sesquiterpenoid dimers,12 new sesquiterpenoid dimers,artematrovirenolides A—D(1—4)and artematrolides S—Z(8—12),were isolated from the EtOAc fraction of Artemisia atrovirens through a bioactivity-guided *** structures were elucidated by comprehensive spectroscopic data and absolute configuration was assigned based on single crystal X-ray diffraction data and ECD ***,all compounds are presumably formed via[4+2]cycloaddition involving three connecting *** 1—4 are four novel hetero-dimeric[4+2]Diels-Alder adducts dimerized from a rotundane-type unit and a guaiane-type monomer,and compounds 5—12 are eight new homo-dimeric[4+2]adducts derived from two guaianolide moieties.A putative biosynthetic pathway for compounds 1—4 was also *** 4,6,7,and 10 demonstrated moderate cytotoxicity against HepG2,SMMC-7721,and Huh7 cell lines with IC50 values ranging from 9.3 to 62.3μmol/***,compounds 5 and 11 manifested cytotoxicity with IC50 values of 13.6 and 12.8(HepG2),18.5 and 13.1(SMMC-7721),and 16.5 and 19.4μmol/L(Huh7),respectively,which were equivalent to the positive control,*** investigation suggests that compounds 5 and 11 might be considered as potent antihepatoma candidates and deserve further structural modification and mechanism study.

关键词： Artemisia atrovirens Sesquiterpenoid dimers Structure elucidation X-ray diffraction Antihepatoma activity

Synthesis of Novel 1-Arylsulfonyl-4-(1′-N-2′, 3′, 4′, 6′-tetra- O-acetyl-β-D-glucopyranosyl)thiosemicarbazides

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Chinese Chemical Letters 2006年第2期17卷 153-155页

作者： Yu Xin li Zheng Ming li Wei Guang ZHAO Wen li DONG su hua WANG State Key Laboratory of Elemento-Organic Chemistry Nankai University Tianjin 300071

The synthesis of novel 1-arylsulfonyl -4- （1＇-N -2＇, 3＇, 4＇, 6＇-tetra-O-acetyl-β-D-gluco- pyranosyl） thiosemicarbazides via condensation of 2, 3, 4, 6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate with substituted phenylsulfonyl hydrazines was described. Their structures and physical properties were confirmed by ^1H NMR, ^13C NMR spectra, elemental analysis and MS.

关键词： Phenylfulfonyl hydrazine thiosemicatbazide condensation.

Artemiprincepsolides A-F,Novel Germacrane-guaiane and Eudesmane-guaiane Sesquiterpenoid Dimers from Artemisia princeps and Their Antihepatoma Activity

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Chinese Journal of Chemistry 2023年第20期41卷 2648-2656页

作者： li-hua su Wen-Jing Ma Yun-Bao Ma Tian-Ze li Chang-An Geng Wei Dong Xiao-Feng He Xue-Mei Zhang Ji-Jun Chen State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of SciencesKunmingYunnan650201 China University of Chinese Academy of Sciences Beijing100049 China

Artemiprincepsolides A-F(1-6)were isolated from Artemisia princeps guided by bioactivity and elucidated by comprehensive spectral data and ECD *** 1-3 represented the first connecting model of germacrane-guaiane hetero-dimeric adducts,and compounds 4-6 were eudesmane-guaiane hetero-coupled sesquiterpenoid dimers,meanwhile,all these were presumably formed by Diels-Alder *** 1-6 were evaluated for their hepatomatic cytotoxicity on three hepatoma cell lines,and demonstrated cytotoxicity with IC_(50)values in the range of 5.0-67.3μmol/***,compound 1 manifested significant cytotoxicity against HepG2,Huh7,and SK-Hep-1 cells with IC_(50)values of 9.9,9.2,and 5.0μmol/L,which were almost equivalent to the positive control,*** cytometry data and Western blot assays revealed the most active compound 1 dose-dependently inhibited cell migration and invasion,and significantly induced HepG2 cells arrest in G2/M phase by downregulating proteins pcdc2 and upregulating the level of protein CyclinB1;and induced apoptosis by downregulating of Bcl-2 expression and upregulating Bax level.

关键词： Artemisia princeps Hetero-coupled sesquiterpenoid dimers Structure elucidation Stereochemistry Artemiprincepsolides Biological activity Antihepatoma activity Apoptosis

Influence of ligand with Fine Difference at Donor Site on MMCT Property in Binuclear Mixed Valence Complexes

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Chinese Journal of Structural Chemistry 2021年第2期40卷 207-216,147页

作者： li su-hua YANG Yu-Ying ZHANG Yu-Xiao WU Xin-Tao SHENG Tian-Lu State Key Laboratory of Structural Chemistry Fujian Institute of Research on the Structure of MatterChinese Academy of SciencesFuzhou 350002China College of Chemistry Fuzhou UniversityFuzhou 350002China University of Chinese Academy of Sciences Beijing 100049China

To investigate how the electronic effect of ligand at donor site influences electronic communication or metal-to-metal charge transfer(MMCT)properties in similar mixed-valence(MV)complexes,a series of binuclear organometallic complexes,MeCp(dppe)RuCNFeCl_(3)(1),MeCp(PPh_(3))_(2)RuCNFeCl_(3)(2),Cp^(*)(dppe)FeCNFeCl_(3)(3),Cp^(*)(dppe)RuCNFeCl_(3)(4)and Cp^(*)(PPh_(3))_(2)RuCNFeCl_(3)(5),have been synthesized and *** electronic absorptions of these complexes show the presence of MMCT properties between RuⅡ or FeⅡ and FeⅢ ions,strongly supported by the theoretical *** increasing electron-donating ability of ligands(PPh3>dppe,Cp^(*)>MeCp)at donor site,the MMCT absorption bands are red-shifted,which expresses in the sequence of absorption bands with 1(500 nm),4(536 nm),2(542 nm),5(580 nm)from high-energy to ***,the MMCT absorption energy of 4(536 nm)is larger than that of 3(760 nm)due to the stronger electron-donating ability of FeⅡ than RuⅡ.Furthermore,these complexes belong to the Class Ⅱ systems according to the Robin and Day’s classification.

关键词： metal-to-metal charge transfer(MMCT) mixed-valence complexes ClassⅡ

Artemyrianosins A-J,cytotoxic germacrane-type sesquiterpene lactones from Artemisia myriantha

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Natural Products and Bioprospecting 2022年第1期12卷 199-210页

作者： Xin Zhang Yun-Bao Ma Xiao-Feng He Tian-Ze li Chang-An Geng li-hua su Shuang Tang Zhen Gao Ji-Jun Chen State Key Laboratory of Phytochemistry and Plant Resources in West China Yunnan Key Laboratory of Natural Medicinal ChemistryKunming Institute of BotanyChinese Academy of Sciences132#Lanhei RoadKunming 650201YunnanPeople’s Republic of China University of Chinese Academy of Sciences Beijing 100049People’s Republic of China

Ten new germacrane-type sesquiterpenoids,artemyrianosins A-J(1-10),were isolated from the aerial parts of Arte-misia *** structures were elucidated by spectral analyses including UV,IR,HRESIMS,1D and 2D NMR,ECD and the absolute configurations of compounds 1 and 7-9 were characterized using X-ray *** isolates were tested their cytotoxicity against three human hepatoma cell lines(HepG2,Huh7,and SK-Hep-1),and com-pounds 1-3,7,and 10 showed cytotoxicity with IC50 values ranging from 43.7 to 89.3μ*** them,the most active compound 3 exhibited activity against three human hepatoma cell lines with IC50 values of 43.7μM(HepG2),47.9μM(Huh7),and 44.9μM(SK-Hep-1).

关键词： Artemisia myriantha Artemyrianosins A-J Germacrane-type sesquiterpenoids Cytotoxicity

Artemlavanins A and B from Artemisia lavandulaefolia and Their Cytotoxicity Against Hepatic Stellate Cell line LX2

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Natural Products and Bioprospecting 2020年第4期10卷 243-250页

作者： Cheng Shen Xiao-Yan huang Chang-An Geng Tian-Ze li Shuang Tang li-hua su Zhen Gao Xue-Mei Zhang Jing Hu Ji-Jun Chen State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of SciencesKunming 650201People’s Republic of China Yunnan Key Laboratory of Natural Medicinal Chemistry Kunming 650201People’s Republic of China University of Chinese Academy of Sciences Beijing 100049People’s Republic of China

Two new sesquiterpenoids,artemlavanins A(1)and B(3),together with fifteen known compounds(2 and 4−17)were iso-lated from the EtOH extract of Artemisia *** structures of new compounds were elucidated by extensive spectroscopic analyses(HRESIMS,1D and 2D NMR)and ECD *** 1 was a sesquiterpenoid lactone possessing a rearranged eudesmane skeleton;compounds 2-5,6-8,9 and 10-12 belonged to the eudesmane,guaiane,oppositane and farnesane sesquiterpenoids,respectively;compounds 13-17 were the phenyl derivatives with a 4-hydroxy-acetophenone *** compounds(1-3,5-7,10-12,14,15 and 17)displayed cytotoxicity against hepatic stellate cell line LX2(HSC-LX2)with IC50 values ranging from 35.1 to 370.3μ*** 2,7,10-12 and 17 exhibited the stronger cytotoxicity than silybin(IC50,169.6μM)with IC50 values of 82.1,35.1,95.0,83.8,81.6 and 90.1μ*** 7 as the most active one showed significant inhibition on the deposition of human collagen type I(Col I),human hyaluronic acid(HA)and human laminin(HL)with IC50 values of 10.7,24.5 and 13.3μM.

关键词： Artemisia lavandulaefolia Sesquiterpenoids Artemlavanins Cytotoxicity HSC-LX2

Artemyrianins A-G from Artemisia myriantha and Their Cytotoxicity Against HepG2 Cells

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Natural Products and Bioprospecting 2020年第4期10卷 251-260页

作者： Shuang Tang Yun-Bao Ma Chang-An Geng Cheng Shen Tian-Ze li Xue-Mei Zhang li-hua su Zhen Gao Jing Hu Ji-Jun Chen State Key Laboratory of Phytochemistry and Plant Resources in West China Yunnan Key Laboratory of Natural Medicinal ChemistryKunming Institute of BotanyChinese Academy of SciencesKunming 650201People’s Republic of China University of Chinese Academy of Sciences Beijing 100049People’s Republic of China

Four new sesquiterpenoids,artemyrianins A-D(1-4),and three new norlignans,artemyrianins E-G(5-7),together with five known compounds(8-12),were isolated from the aerial parts of Artemisia myriantha(Asteraceae).The new compounds were established by spectroscopic data analyses(HRMS,IR,1D and 2D NMR),and their absolute configurations were confirmed by the single-crystal X-ray diffraction or ECD *** isolates showed cytotoxicity against HepG2 cells with IC50 values ranging from 33.3 to 145.2μM.

关键词： Artemisia myriantha Artemyrianins A-G Sesquiterpenoids Norlignans Cytotoxicity HepG2 cells

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液压铸件冒口的设计及应用

铸造 2001年第2期50卷 105-108页

作者：李素华崔宝琛榆次液压件厂山西晋中030600

介绍了适用于液压铸铁件冒口的设计及应用情况 ,在保证铸件质量的前提下 ,合理设计冒口 ,提高了补缩效率和工艺出品率。

关键词：液压铸件铸铁件冒口设计浇注系统

Investigating the Aggregation of Imported Cutaneous Leishmaniasis in Henan, Central China

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Biomedical and Environmental Sciences 2021年第3期34卷 247-249页

作者： ZHAO Yu ling li su hua ZHU Xin ZHOU Rui Min YANG Cheng Yun liU Ying NIU Yuan Na LU De ling ZHANG Hong Wei ZHAO Dong Yang Henan Key Laboratory of Infectious Disease Microbiology Henan Center for Disease Control and PreventionZhengzhou 450016HenanChina Luoyang Center for Disease Control and Prevention Luoyang 471023HenanChina

Leishmania is a parasitic disease caused due to infection with Leishmaniasis,which is prevalent in 88 countries across the globe[1].Clinically,Leishmaniasisis is divided into 3 types:visceral leishmaniasis(VL),mucosal... 详细信息

关键词： Leishmania Clinical sis