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Isolation of chemical compositions as dietary antioxidant supplements and neuroprotectants from Chaga mushroom (Inonotus obliquus)

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Food Bioscience 2022年第3期47卷 211-220页

作者： Ye Chang Ming Bai Xiao-Bian Xue Chun-Xin Zou Xiao-Xiao Huang Shao-Jiang Song key laboratory of computational chemistry-based natural antitumor drug research & development Liaoning ProvinceChina Engineering research Center of natural Medicine Active Molecule research & development Liaoning ProvinceChina key laboratory of natural Bioactive Compounds Discovery & Modification ShenyangChina School of Traditional Chinese Materia Medica Shenyang Pharmaceutical UniversityShenyangLiaoning110016China

Excessive free radicals can cause oxidative stress (OS),which lead to neurodegenerative diseases (ND) are harmful to the human ***,it is necessary to explore dietary antioxidants and neuroprotectants from nutrient *** mushroom (Inonotus obliquus ) has been used as an important functional food in many countries for *** present study was carried out to discover active compounds from *** and investigate the in vitro antioxidant activity and neuroprotective *** natural products including two new isocoumarins (1 –2 ),a new 8-O -4′-neolignan (3 ),a new cyclic diarylheptanoid (4 ),and twelve known compounds (5 –16 ) were separated from *** .Their structures were elucidated by extensive spectroscopic analyses of high resolution electrospray mass spectrometry (HRESIMS),ultra violet (UV),and nuclear magnetic resonance (NMR).Among them,compounds 1 and 2 revealed remarkable antioxidant activities through the comprehensive analysis of DPPH,ABTS,and ferric reducing antioxidant power (FRAP) ***,compound 1 demonstrated significant neuroprotective activity by increasing SH-SY5Y cells viability and preventing mitochondrial *** from that,electronic analyses were performed using the highest occupied molecular orbital (HOMO),and the lowest unoccupied molecular orbital (LUMO) to analyze compound 1 .These results indicated that compound 1 had a significant implication for the search of natural raw material to prevent OS and nerve damage in the field of functional foods,and the isocoumarin fragment as well as an oxygenated cis double-bond might be the active sites to play prominent parts in antioxidant and neuroprotective activities of compound 1 .

关键词： Inonotus obliquus Chaga mushroom Functional food Neuroprotective activity Antioxidant activity

Discovery of β-Dihydroagarofuran-Type Sesquiterpenoids from the Leaves of Tripterygium wilfordii with Neuroprotective Activities

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Chinese Journal of chemistry 2021年第2期39卷 337-344页

作者： Shuhui Dong Bin Lin Xiaobian Xue Ming Bai Xiaoxiao Huang Shaojiang Song key laboratory of computational chemistry-based natural antitumor drug research&development Liaoning ProvinceSchool of Traditional Chinese Materia MedicaShenyang Pharmaceutical UniversityShenyangLiaoning110016 China School of Pharmaceutical Engineering Shenyang Pharmaceutical UniversityShenyangLiaoning110016 China

Nine undescribed dihydro-β-agarofuran sesquiterpenoid derivatives(1—9),along with a known analogue(10),were obtained from the leaves of Tripterygium *** gross structures were determined via extensive spectroscopic data,and the absolute configurations were elucidated by means of single-crystal X-ray diffraction analysis and electron circular dichroism(ECD)techniques,which include ECD exciton chirality,octant rule of saturated cyclohexanone and comparison between the experimental and calculated ECD *** the isolated compounds were tested for their neuroprotective activities against H2O2-induced cell injury in human neuroblastoma SH-SY5Y *** 5 and 6 improved cell viability by 16.15%and 15.12%compared with the H2O2 treated group at 25μmol·L^(-1),respectively.

关键词： Tripterygium wilfordii Terpenoids Biological activity Structure elucidation Single-crystal X-ray diffraction

Quassinoids from the Root Barks of Ailanthus altissima:Isolation,Configurational Assignment,and Cytotoxic Activities

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Chinese Journal of chemistry 2021年第4期39卷 879-886页

作者： Ye-Qing Du Ming Bai Xiao-Qi Yu Tian-Ming Lv Bin Lin Xiao-Xiao Huang Shao-Jiang Song key laboratory of computational chemistry-based natural antitumor drug research&development Liaoning ProvinceSchool of Traditional Chinese Materia MedicaShenyang Pharmaceutical UniversityShenyangLiaoning 110016China School of Pharmaceutical Engineering Shenyang Pharmaceutical UniversityShenyangLiaoning 110016China

Main observation and conclusion Quassinoids,a class of highly oxygenated triterpenes,have been isolated as bitter principles from the plants of Simaroubaceae *** new quassinoids,chouchunlactone A-E(1-5),and two known ones were identified from the root barks of Ailanthus altissima Swingle(Simaroubaceae).The chemical structures of the new compounds were deduced by spectroscopic data analyses,NMR calculations and DP4+probability *** absolute configurations were defined by comparison of their experimental and calculated electronic circular dichroism(ECD)spectra data,and compounds 1-2 were further confirmed by single-crystal X-ray ***,compound 5 showed potencies equivalent to sorafenib(IC50 value,9.70μmol·L–1)against HepG2 *** Hoechst 33342 staining,JC-1 fluorescent dye and Annexin V/PI analysis studies demonstrated that 5 can induce apoptosis and attenuate mitochondrial membrane potential(MMP)in HepG2 cells.

关键词： Ailanthus altissima Simaroubaceae Quassinoids Cytotoxicity Apoptosis

Lung protective effects of dietary malate esters derivatives from Bletilla striata against SiO_(2) nanoparticles through activation of Nrf2 pathway

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Chinese Herbal Medicines 2023年第1期15卷 76-85页

作者： Di Zhou Wenhui Chang Jiaxin Qi Gang Chen Ning Li key laboratory of computational chemistry-based natural antitumor drug School of Traditional Chinese Materia MedicaShenyang Pharmaceutical UniversityShenyang 110016China

Objective: To study the protective activities of the dietary malate esters derivatives of Bletilla striata against SiO_(2)nanoparticles-induced A549 cell lines and its mechanism ***: The components were isolated and elucidated by spectroscopic methods such as 1D NMR and 2D NMR. And MTT assays was used to tested these components on the A549 cell survival rates and ROS or proteins levels were detected by Western ***: A new glucosyloxybenzyl 2-isobutylmalate(a malate ester derivative), along with 31 known compounds were isolated and identified from n-BuOH extract of EtOH extract of B. striata. Among them,compounds 3, 4, 11, 12 and 13 possessed noteworthy proliferative effects for damaged cells, with ED50of 14.0, 13.1, 3.7, 11.6 and 11.5 μmol/L, respectively, compared to positive control resveratrol(ED50, 14.7 μmol/L). Militarine(8) prominently inhibited the intracellular ROS level, and increased the expression of Nrf2 and its downstream genes(HO-1 and γ-GCSc). Furthermore, Nrf2 activation mediates the interventional effects of compound 8 against SiO_(2)nanoparticles(nm SiO_(2))-induced lung ***, treatment with compound 8 significantly reduced lung inflammation and oxidative stress in nm SiO_(2)-instilled mice. Molecular docking experiment suggested that 8 bound stably to the HO-1 protein by hydrogen bond ***: The dietary malate esters derivatives of B. striata could significantly increase the viability of nm SiO_(2)-induced A549 cells and decrease the finer particles-induced cell damages. Militarine is especially promising compound for chemoprevention of lung cancer induced by nm SiO_(2)through activation of Nrf2 pathway.

关键词： Bletilla striata(Thunb.)Reichb.f. dietary malate esters derivatives lung cancer chemoprevention militarine SiO_(2)nanoparticles-induced A549 cell

Rapid discovery of two unprecedented meroterpenoids from Daphne altaica *** molecular networking integrated with MolNetEnhancer and Network Annotation Propagation

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Chinese Chemical Letters 2024年第8期35卷 294-298页

作者： Wei-Yu Zhou Zi-Han Xi Ning-Ning Du Li Ye Ming-Hao Jiang Jin-Le Hao Bin Lin Guo-Dong Yao Xiao-Xiao Huang Shao-Jiang Song key laboratory of computational chemistry-based natural antitumor drug research&development Liaoning ProvinceEngineering Research Center of Natural Medicine Active Molecule Research&DevelopmentLiaoning ProvinceKey Laboratory of Natural Bioactive Compounds Discovery&ModificationShenyangSchool of Traditional Chinese Materia Medic1Shenyang Pharmaceutical UniversityShenyang 110016China key laboratory of Structure-based drug Design and Discovery of Ministry of Education Shenyang Pharmaceutical UniversityShenyang 110016China Wuya College of Innovation Shenyang Pharmaceutical UniversityShenyang 110016China

Under the guidance of the approach which integrates molecular networking,MolNetEnhancer and Net-work Annotation Propagation(NAP),daphnaltaicanoids A and B(1 and 2)with unprecedented 9-oxa-tetracyclo[6.***.1.0^(2,6).0^(8,13)]pentadecane and tetracyclo[5.***.0.1^(2,5).2^(4,11)]tridecane central frameworks were iso-lated from Daphne altaica Pall.,representing two types of unparalleled meroterpenoid *** struc-tures were elucidated by extensive spectroscopic analysis,nuclear magnetic resonance(NMR)calcula-tions,DP4+analysis and electronic circular dichroism(ECD)*** plausible biosynthetic path-ways for 1 and 2 were ***,2 exerted potent neuroprotective activities which were su-perior to trolox at 12.5 and 25μmol/***,1 and 2 exhibited more noticeable acetylcholinesterase inhibitory activities than *** docking simulations were performed to explore the inter-molecular interaction of compounds 1 and 2 with *** bioactivity evaluation results highlight the prospects of 1 and 2 as a novel category of neurological agents.

关键词： Daphne altaica Pall. Molecular networking MolNetEnhancer NAP Unprecedented meroterpenoid frameworks Neuroprotective activities Acetylcholinesterase inhibitors

Discovery of alkaloids from the leaves of Isatis indigotica Fortune with neuroprotective activity

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Chinese Journal of natural Medicines 2021年第9期19卷 680-685页

作者： XI Yu-Fei LOU Li-Li HAN Feng-Ying WANG Xiao-Bo HUANG Xiao-Xiao YAO Guo-Dong SONG Shao-Jiang key laboratory of computational chemistry-based natural antitumor drug research&development Liaoning ProvinceSchool of Traditional Chinese Materia MedicaShenyang Pharmaceutical UniversityShenyang 110016China Chinese People's Liberation Army Logistics Support Force No.967 Hospital Dalian 116000China

Seven alkaloids including five undescribed ones(1 a/1 b,2,3 and 5)were obtained from the leaves of Isatis indigotica *** structures were established by extensive spectroscopic *** absolute configurations of compounds 1 a,1 b,3 and 5 were determined by comparison of the experimental and calculated electronic circular dichroism(ECD)***,the neuroprotective effects of all the isolates against H_(2)O_(2)-induced injury in SH-SY5 Y cells were evaluated in vitro by MTT ***,Annexin V-FITC/PI double staining was performed,while the activities of antioxidant enzymes(SOD,CAT and GSH-Px)for compounds 1 a and 1 b were measured.

关键词： Isatis indigotica Alkaloids Neuroprotective effects Structure elucidation

Diverse sesquiterpenoids from Litsea lancilimba *** potential neuroprotective effects against H_(2)O_(2)-induced SH-SY5Y cell injury

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Chinese Journal of natural Medicines 2022年第9期20卷 701-711页

作者： ZHANG Yi-Jie BAI Ming LI Jia-Yi QIN Shu-Yan LIU Yu-Yang HUANG Xiao-Xiao ZHENG Jiang SONG Shao-Jiang key laboratory of computational chemistry-based natural antitumor drug research&development Liaoning ProvinceEngineering Research Center of Natural Medicine Active Molecule Research&DevelopmentLiaoning ProvinceKey Laboratory of Natural Bioactive Compounds Discovery&ModificationShenyangSchool of Traditional Chinese Materia MedicaShenyang Pharmaceutical UniversityShenyang 110016China Wuya College of Innovation Shenyang Pharmaceutical UniversityShenyang 110016China State key laboratory of Functions and Applications of Medicinal Plants Guizhou Provincial Key Laboratory of PharmaceuticsGuizhou Medical UniversityGuiyang 550004China

Five undescribed sesquiterpenoids(1–5),and nine known sesquiterpenoids(6–14)were obtained from the fruits of Litsea lancilimba *** LC-MS/MS molecular networking *** A(1)possessed a unique 8-member ring through unexpected cyclization of the methyl group on C-10 of *** structures were elucidated by spectroscopic techniques including IR,UV,NMR,HR-ESI-MS,and their absolute configurations were assigned by ECD *** isolated sesquiterpenoids were analyzed by bioinformatics and evaluated for their neuroprotective effects against H_(2)O_(2)-induced injury in human neuroblastoma SH-SY5Y cells.

关键词： Litsea lancilimba Lauraceae Sesquiterpenoids Neuroprotective effect

Brusatol:A potential anti-tumor quassinoid from Brucea javanica

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Chinese Herbal Medicines 2020年第4期12卷 359-366页

作者： Xiao-qi Yu Xin-yue Shang Xiao-xiao Huang Guo-dong Yao Shao-jiang Song Liaoning key laboratory of computational chemistry-based natural antitumor drug research&development School of Traditional Chinese Materia MedicaShenyang Pharmaceutical UniversityShenyang 110016China Jiangsu Kanion Pharmaceutical Co. Ltd.Lianyungang 222001China

Brusatol,a triterpene lactone compound mainly from Brucea javanica,sensitizes a broad spectrum of cancer *** is known as a specific inhibitor of nuclear factor-erythroid 2-related factor 2(Nrf2)*** this review,we provide a comprehensive overview on the antitumor effect and molecular mechanisms of brusatol in vitro and in *** review also covers pharmacokinetics studies,modification of dosages forms of *** evidences have validated the value of brusatol as a chemotherapeutic agent in cancers,which may contribute to drug development and clinical application.

关键词： antitumor Brucea javanica(L.)Merr. brusatol triterpene lactone

New norlignan enantiomers from the fruit of Crataegus pinnatifida with neuroprotective activities

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Chinese Chemical Letters 2020年第5期31卷 1254-1258页

作者： Rui Guo Tianming Lv Fengying Han Zilin Hou Guodong Yao Bin Lin Xiaobo Wang Xiaoxiao Huang Shaojiang Song key laboratory of computational chemistry-based natural antitumor drug research&development Liaoning ProvinceSchool of Traditional Chinese Materia MedicaShenyang Pharmaceutical UniversityShenyang 110016China School of Pharmaceutical Engineering Shenyang Pharmaceutical UniversityShenyang 110016China Chinese People's Liberation Army Logistics Support Force No.967 Hospital Dalian 116021China

(±)-Crataegusnorin A(la/1b) and B(2a/2b),two pairs of rare 8,9’-epoxy-type norlignan enantiomers featuring a y-butyrolactone ring,were isolated from the fruit of Crataegus *** structures were determined via extensive spectroscopic ***-independent atomic orbital(GIAO) NMR chemical shift calculations,combined with the advanced statistical method DP4+were employed to establish the relative configurations of four ***,chiral separation was accomplished by chiral chromatographic column and the absolute configurations of the four compounds were unambiguously assigned by comparison between their experimental electronic circular dichroism curves with the quantum-mechanically calculated curves based on time-dependent density functional theory(TDDFT).All the isolates were evaluated fo r their neuroprotective activities against H2O2-induced cell injury in human neuroblastoma SH-SY5Y *** results showed that two pairs of enantiomers 1a/1b and 2a/2b displayed diff;erent effect on neuroprotective *** them,compound 2a displayed the most potent neuroprotective effect Further flow cytometry analysis indicated that 2a could protect SH-SY5Y cells from oxidative damage through inhibiting cell apoptosis.

关键词： Crataegus pinnatifida Norlignan enantiomer Neuroprotective activity SH-SY5Y cells Apoptosis