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Artemordins A-S, Cadinane-Type Sesquiterpenoid Dimers from Artemisia ordosica and Their Antihepatoma Activities

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Chinese Journal of Chemistry 2024年第13期42卷 1493-1508页

作者： Yuan Wang Tian-Ze Li Yun-Bao Ma Chang-An Geng Yong-Cui Wang ji-jun chen State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of SciencesKunmingYunnan 650201China University of Chinese Academy of Sciences Beijing 100049China

Nineteen new cadinane-involving sesquiterpenoid dimers,artemordins A-S(1-—19),together with 13 known SDs(20-32)were isolated from Artemisia *** structures and absolute configurations were established by comprehensive spectral analyses,X-ray single crystal diffraction,theoretical ECD,and NMR ***,artemordins A-F(1—6)were the first examples of two cadinane units constructed by unprecedented C-3−C-15′or C-3−C-13′single bond with an oxido-rearranged 6/5/6/6 fused ring system;artemordins G-K(7-11)were biogenetically connected by[4+2]cycloaddition reaction and artemordins G-J(7-10)possessed a novel 5/6/6/6/6/6/5-heptacyclic fused ring *** L-S(12-19)were formed by esterification,which involved three different types of *** assay suggested that the most active compounds,artemordins B and H(2 and 8),exhibited inhibitory activities on three hepatoma cell lines with IC50 values of 26.9 and 25.1μmol/L(HepG2),29.5 and 18.3μmol/L(Huh7),19.7 and 15.7μmol/L(SK-Hep-1).

关键词： Artemisia ordosica Artemordins A-s Cadinane-type sesquiterpenoid dimers Antihepatoma activities Terpenoids Natural products Cytotoxicity

Three Types of Isocoumarins with Unusual Carbon Skeletons from Artemisia dubia var. subdigitata and Their Antihepatoma Activity

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Chinese Journal of Chemistry 2024年第16期42卷 1901-1912页

作者： Ke-Xin Yang Tian-Ze Li Yun-Bao Ma Yong-Cui Wang Feng-jiao Li ji-jun chen State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of SciencesKunmingYunnan 650201China University of Chinese Academy of Sciences Beijing 100049China

Ten novel isocoumarins,including four pairs of enantiomers,were isolated from Artemisia dubia ***(Asteraceae).Compounds 1,2 and 3a/3b possessed a unique 6/6/6-tricyclic system comprising an unusual 1-(2-methylcyclohexyl)propan-1-one moiety fused with isocoumarin core *** 4a/4b were characterized as an unexpected 2,5-dimethylcyclohexan-1-one scaffold,and compounds 5a/5b and 6a/6b were rare 1,*** structures and absolute configurations were elucidated through spectroscopic data,X-ray crystallography,ECD and NMR calculations with DP4+*** biosynthetic pathways were proposed from the naturally occurring *** pharmacological analysis suggested that the targets of compound 1 were significantly enriched in the cell cycle and Pl3K-Akt signaling *** molecular docking revealed that compound 1 had high binding affinity with CDK2(total score:6.8717).Furthermore,compounds 1 and 2 exhibited inhibitory activity on three human hepatoma cell lines,with inhibitory ratios of 85.1% and 84.5%(HepG2),88.2% and 87.3%(Huh7),and 69.2% and 69.1%(SK-Hep-1)at 200μmol·L^(-1),respectively.

关键词： Artemisia dubia var.subdigitata Isocoumarins Antihepatoma activity Cancer Natural products X-ray diffraction

Perioperative complication incidence and risk factors for retroperitoneal neuroblastoma in children:analysis of 571 patients

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World Journal of Pediatrics 2024年第3期20卷 250-258页

作者： Min He jia-Bin Cai Xuan Wu Yin-Bing Tang jin-Yan Wang jun-Qin Mao ji-jun chen Li-Feng Zhang Zhong-Hai Guan jie-Ni Xiong Wan-Xin Peng jin-Hu Wang Ting Tao Pediatric Cancer Research Center National Clinical Research Center for Child HealthHangzhouChina Department of Surgical Oncology Children's HospitalZhejiang University School of MedicineHangzhouChina Cancer Center Zhejiang UniversityNo.3333 Binsheng RodeHangzhouChina

Background Surgery plays an important role in the treatment of *** complications may impact the course of neuroblastoma *** date,comprehensive analyses of complications and risk factors have been *** Patients with retroperitoneal neuroblastoma undergoing tumor resection were retrospectively analyzed between 2014 and *** data collected included clinical characteristics,operative details,operative complications and postopera-tive *** factors for perioperative complications of retroperitoneal neuroblastoma were *** A total of 571 patients were enrolled in this *** complications were observed in 255(44.7%)*** leakage(28.4%),diarrhea(13.5%),and injury(vascular,nerve and organ;7.5%)were the most frequent *** were three operation-related deaths(0.53%):massive hemorrhage(n=1),biliary tract perforation(n=1)and intestinal necrosis(n=1).The presence of image-defined risk factors(IDRFs)[odds ratio(OR)=2.09,P<0.01],high stage of the International Neuroblastoma Risk Group staging system(INRGSS)(OR=0.454,P=0.04),retroperitoneal lymph node metastasis(OR=2.433,P=0.026),superior mesenteric artery encasement(OR=3.346,P=0.003),and inferior mesenteric artery encasement(OR=2.218,P=0.019)were identified as independent risk factors for perioperative *** Despite the high incidence of perioperative complications,the associated mortality rate was quite ***-perative complications of retroperitoneal neuroblastoma were associated with IDRFs,INRGSS,retroperitoneal lymph node metastasis and vascular *** with high-risk factors should receive more serious attention during surgery but should not discourage the determination to pursue total resection of neuroblastoma.

关键词： Complication Neuroblastoma Risk factors Surgery

DNA methylation assay for colorectal carcinoma

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Cancer Biology & Medicine 2017年第1期14卷 42-49页

作者： ji-jun chen Ai-Qin Wang Qing-Qi chen Research&Development Allonger LLCColumbia 22045MDUSA Mei chen Biotechnology Co.Ltd. Qingdao 266012China The Affiliated Hospital of Qingdao University Qingdao 266003China

Colorectal carcinoma(CRC) is a common cause of morbidity and mortality worldwide. Two pathogenic pathways are involved in the development of adenoma to CRC. The first pathway involves APC/β-catenin characterized by chromosomal instability resulting in the accumulation of mutations. The second pathway is characterized by lesions in DNA mismatch repair *** DNA methylation in selected gene promoters has emerged as a new epigenetic pathway in CRC development. CRC screening is the most efficient strategy to reduce death. Specific DNA methylation events occur in multistep *** gene silencing is a causative factor of CRC development. DNA methylations have been extensively examined in stool from CRC and precursor lesions. Many methylated genes have been described in CRC and adenoma, although no definite DNA methylation biomarkers panel has been established. Multiple DNA methylation biomarkers, including secreted frizzled-related protein 2, secreted frizzled-related protein 1, tissue factor pathway inhibitor 2, vimentin, and methylguanine DNA methyltransferase, have been further investigated, and observations have revealed that DNA methylation biomarkers exhibit with high sensitivity and specificity. These markers may also be used to diagnose CRC and adenoma in early stages. Real time polymerase chain reaction(q PCR) is sensitive, scalable, specific, reliable, time saving, and cost effective. Stool exfoliated markers provide advantages, including sensitivity and specificity. A stool q PCR methylation test may also be an enhanced tool for CRC and adenoma screening.

关键词： Biomarker colorectal carcinoma DNA methylation real time PCR stool

Bishyoscyamine,one unusual dimeric tropane alkaloid from Anisodus acutangulus

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Chinese Chemical Letters 2013年第3期24卷 236-238页

作者： Chang-An Geng Yun-Bao Ma ji-jun chen State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of Sciences

One unusual dimeric tropane alkalolcl, blshyoscyamme, was ISOlated from the roots o! Amsoaus acutangulus, whose structure including the absolute stereochemistry was unambiguously determined based on extensive 1D NMR and 2D NMR, HR-ESI-MS [et]D and CD spectroscopic analyses. To our knowledge, bishyoscyamine is the first example of tropane alkaloid dimer condensed by a C-N bond.

关键词： Anisodus acutangulusBishyoscyamineTropane alkaloid dimers

Synthesis,Crystal Structure and Quantum Chemical Investigation of Bis-Schiff Base Compounds Derived from2-phenyl-1,2,3-triazole-4-carboxaldehyde with Diamine

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Chinese Journal of Structural Chemistry 2008年第5期27卷 616-621页

作者： XIE Ling LIU Gang WANG Yan WANG ji-De chen jun-Feng Department of Chemistry Key Laboratory of Oil ＆ Gas Fine Chemicals Ministry of Education Xinjiartg University Urumqi 830046 China

Two new schiff base N,N＇-bis（（2-phenyl-2H-1,2,3-triazol-4-yl）methylene）-1,3-propanediamine （1） and N,N＇-bis（（2-phenyl-2H-1,2,3-triazol-4-yl）methylene） -1,4-butanediamine （2） were synthesized by condensation of 2-phenyl-1,2,3-triazole-4-carboxaldehyde with diamine, and characterized by elemental analysis, IR, IH NMR and MS spectra. Their crystal structures were determined by X-ray single crystal diffraction. Both crystals belong to the monoclinic system, space group P21/c. For compound 1（C21H20N8, Mr=384.45）： a = 16.314（3）, b =5.7168（11）, c = 21.316（4） A, β = 105.3（2）°, Z = 4, V = 1917.6（7） A^3, De =1.332 g/cm^3, F（000） = 808,μ = 0.086 mm 1, R = 0.0533 and wR = 0.1460; for compound 2 （C22H22N8, Mr=398.48）： a = 8.6156（17）, b = 5.2964（11）, c = 22.665（5）A, β = 100.54（3）°, Z = 2, V = 1016.8（4） A^3, De= 1.302 g/cm^3, F （000） = 420, μ = 0.083 mm^-1, R = 0.0373 and wR = 0.1155. Based on the crystal data, quantum chemistry calculation was performed on the two title compounds by means of Gaussian 98 program. The molecular orbital energies and atomic net charges population were obtained. Furthermore, we antilyzed their active atoms. The investigation can serve as a theoretical guide to study the synthesis and activity of the title compounds.

关键词： schiff base crystal structure quantum chemical calculation

The Progress of Anti-HBV Constituents from Medicinal Plants in China

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Natural Products and Bioprospecting 2018年第4期8卷 227-244页

作者： Chang-An Geng ji-jun chen State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of SciencesNo.132 Lanhei RoadKunming 650201China Yunnan Key Laboratory of Natural Medicinal Chemistry Kunming 650201China University of Chinese Academy of Sciences Beijing 100049China

Hepatitis B virus(HBV)infection causing acute and chronic hepatitis is a serious problem worldwide,whereas the current treatment methods are *** Chinese herbs that have long been used for medicinal purposes are fascinating sources for novel anti-HBV *** paper summarizes the progress of anti-HBV constituents from diverse medicinal plants in China to provide information for searching new anti-HBV drugs from natural sources.

关键词： Hepatitis B virus Anti-HBV activity Medicinal plants HBsAg HBeAg HBV DNA

A Fragmentation Study on Four Unusual Secoiridoid Trimers,Swerilactones H–K,by Electrospray Tandem Mass Spectrometry

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Natural Products and Bioprospecting 2016年第6期6卷 297-303页

Swerilactones H–K(1–4)as four unprecedented secoiridoid trimers represent a new type of natural product,which has attracted much interest of natural chemists due to their novel skeletons and promising *** order to well understand their MS fragmentation behaviors,they were investigated by electrospray ionization ion-trap time-of-flight multistage product ion mass spectrometry(ESI-IT-TOF-MSn)for the first *** protonated molecules([M?H]?)of swerilactones J and K,and deprotonated molecules([M-H]-)of swerilactones H,J and K were readily observed in the conventional single-stage mass spectra(MS);however only the[M?Cl]-ion for swerilactone I was obtained in negative *** on the MSn study,the fragmentation pathways of swerilactones H and I in negative mode,and swerilactones J and K in both positive and negative modes were *** neutral losses of H_(2)O,CO,CO_(2)and C_(2)H_(4)O moieties are the particular elimination from the precursor ions due to the presence of hydroxyl,d-lactone and 1-O-ethyl moieties in their structures,of which the retro-Diels–Alder cleavage was the most particular *** fragment ions at m/z 341 and 291 in negative mode can be considered as the diagnostic ions for secoiridoid *** investigation will provide valuable information for their fast characterization from complicated natural mixtures and extensive understanding their structural architectures.

关键词： ESI-IT-TOF-MSn Fragmentation rules Secoiridoid trimers Swerilactones H-K Retro-Diels-Alder(RDA)cleavage

A Fragmentation Study on Four Oligostilbenes by Electrospray Tandem Mass Spectrometry

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Natural Products and Bioprospecting 2019年第4期9卷 279-286页

作者： chen‑chen Zhang Chang‑An Geng ji‑jun chen State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of Sciences132#Lanhei RoadKunming 650201YunnanPeople’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

Oligostilbenes have attracted much interest due to their intricate structures and diverse *** this study,two stilbene dimers,(−)-7,8-cis-ε-viniferin(1)and carasiphenol A(2),and two trimers,suffruticosol A(3)and suffruticosol C(4),were investigated by electrospray ionization ion-trap time-of-flight multistage mass spectrometry(ESI-IT-TOF-MS^(n)).Based on the MS^(n) study,the fragmentation pathways and diagnostic ions of four oligostilbenes in both positive and negative modes were *** consecutive elimination of phenol(C_(6)H_(6)O)and resorcinol(C_(6)H_(6)O_(2))moieties were the particular dissociation for oligostilbenes due to the presence of 1,2-diphenylethylene *** present MS^(n) fragmentation study will provide valuable information for the fast characterization of oligostilbenes from complicated natural mixtures.

关键词： ESI-IT-TOF-MS^(n) Fragmentation rules Oligostilbenes