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Cobalamin-dependent radical S-adenosyl-L-methionine protein functions with a partner to successively methylate tricyclic indole alkaloid for chuangxinmycin maturation and derivatization

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Science China Chemistry 2025年第1期68卷 308-316页

作者： Sili Wang Jiancheng Huang Yanan Du Wei Huang Yufeng Xue Xiaokun Xu Guannan Zhong Yuanyuan Shi Bin Hong Xiaoying Bian Wen Liu State Key laboratory of chemical biology Shanghai Institute of Organic Chemistry University of Chinese Academy of SciencesChinese Academy of Sciences State Key laboratory of Microbial Technology Shandong University National Health Commission (NHC) Key laboratory of Biotechnology for Microbial Drugs Institute of Medicinal BiotechnologyChinese Academy of Medical Science & Peking Union Medical College

Cobalamin(Cbl)-dependent radical S-adenosyl-L-methionine(SAM) proteins constitute the largest collection of the radical SAM superfamily that has hundreds of thousands of individual members. Many of these proteins are involved in the biosynthesis of pharmaceutically important natural products to catalyze chemically demanding reactions. In the biosynthetic pathway of chuangxinmycin(CXM), a unique indole alkaloid antibiotic with potent anti-infective activity, functionalization of the characteristic thiopyrano[4,3,2-cd]indole scaffold by regio-and stereoselective C3-methylation is believed to rely on a Cbl-dependent radical process, which, however, remained to be reconstituted biochemically. We here report the dissection of this enzymatic process, which requires the incorporation of Cxm8, a Cbl-dependent radical SAM protein, with Cxm9, a DUF5825family protein that shares no homology to any proteins of known functions. Cxm8 and Cxm9 function together by forming an unexpected heterodimeric complex that selectively catalyzes C3-methylation of the tricyclic indole-S-hetero ring system in a successive manner, achieving CXM and a recently identified, C3-dimethylated congener. Detailed biochemical characterization,isotope labeling, structural simulation and bioinformatics analysis rationalized the catalysis of the Cxm8/Cxm9 complex and particularly the necessity of the DUF5825 protein for C3-methylase activity. This is the first example that a Cbl-dependent protein acts with a partner to exhibit radical SAM activity.

关键词： cbl-dependent radical SAM protein biosynthesis chuangxinmycin stereoselective methylation

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Deciphering fungal metabolon coupling tandem inverse-electrondemand Diels-Alder reaction and semipinacol rearrangement for the biosynthesis of spiro polycyclic alkaloids

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Science China Chemistry 2025年第1期68卷 288-296页

作者： Shuai Liu Wen-Qiang Xu Ying-Tong Di Man-Cheng Tang Ding-Kang Chen Ming-Ming Cao Yao-Wen Chang Hong-Yu Tang Chun-Mao Yuan Jun-Bo Yang Zhi-Li Zuo Han Guo Zi-Fei Xu Ying Zeng Yun-Dong Wu Xiao-Jiang Hao Key laboratory of Phytochemistry and Natural Medicines (Chinese Academy of Sciences) Kunming Institute of Botany Chinese Academy of Sciences University of Chinese Academy of Sciences Lab of Computational Chemistry and Drug Design State Key Laboratory of Chemical Oncogenomics Peking University Shenzhen Graduate School Shenzhen Bay laboratory State Key laboratory of Microbial Metabolism School of Life Sciences & Biotechnology Shanghai Jiao Tong University State Key laboratory of Functions and Applications of medicinal Plants Guizhou Medical University Molecular biology Experimental Center Germplasm Bank of Wild Species in Southwest China Kunming Institute of Botany Chinese Academy of Sciences Yunnan Key laboratory for Wild Plant Resources Kunming Institute of Botany Chinese Academy of Sciences Research Unit of chemical biology of Natural Anti-Virus Products Chinese Academy of Medical Sciences

In the intricate process of natural product biosynthesis, a metabolon can enhance metabolic flux by associating sequential enzymes. A fungal metabolon, comprising of flavin-dependent monooxygenase Spe F and P450 monooxygenase Spe G, is identified in the biosynthesis of spiro polycyclic alkaloids(+)-notoamide B and its diastereomer(+)-versicolamide B. Using notoamide E as a substance, Spe F/Spe G metabolon can control the stereoselectivity of its 2,3-epoxidation, followed by hydrogen atom ion at C-17 to generate reactive epoxide tau-m A with dienyl iminium unit. Subsequently,(+)-notoamide B and(+)-versicolamide B are produced via tandem nonenzymatic inverse-electron-demand Diels-Alder reaction and semipinacol rearrangement. This provides the first example of metabolon in the biosynthesis of spiro-prenylated indole alkaloids.

关键词： metabolon Diels-Alder reaction semipinacol rearrangement biosynthesis notoamides spiro polycyclic alkaloids

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Enhanced subacute ischemic stroke treatment via multistage drug delivery system design for combination therapy

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Science China Chemistry 2025年

作者： Xihan Xu Juan-Juan Li Jiamin Li Hui-Yan Zhang Yilin Qi Bing-Sen Shi Tianqi Li Shan-Shan Su Weitao Zhao Chang Chen Zhongying Gong Huiyu Liu Ke-Rang Wang Dong-Sheng Guo Xue Xue State Key laboratory of medicinal chemical biology College of Pharmacy Nankai University College of Chemistry State Key Laboratory of Elemento-Organic Chemistry Key Laboratory of Functional Polymer Materials (Ministry of Education) Frontiers Science Center for New Organic Matter Collaborative Innovation Center of Chemical Science and EngineeringNankai University College of Chemistry and Materials Science State Key Laboratory of New Pharmaceutical Preparations and Excipients Key Laboratory of Medicinal Chemistry and Molecular Diagnosis (Ministry of Education) Key Laboratory of Chemical Biology of Hebei Province Hebei Research Center of the Basic Discipline of Synthetic Chemistry Hebei University Department of Neurology Tianjin First Central Hospital School of Medicine Nankai University Beijing Advanced Innovation Center for Soft Matter Science and Engineering State Key Laboratory of Organic-Inorganic Composites Beijing Laboratory of Biomedical Materials Bionanomaterials & Translational Engineering Laboratory Beijing Key Laboratory of BioprocessBeijing University of Chemical Technology

The management of acute ischemic stroke remains challenging due to its abrupt onset and the narrow treatment window,resulting in high rates of disability and *** therapy for neuroprotection and neurorepair strategies provided new hopes for subacute stroke *** we designed a multistage nanodelivery system that matches the unique microenvironment of the subacute phase of stroke,which utilizes calixarene as a building block to effectively load the neuroprotective drug *** calixarene is designed with glycosidic linkages targeting the glucose transporter 1 (GLUT1)on the blood-brain barrier (BBB) and azo bonds that are responsive to hypoxic ***,the decomposed calixarene molecules themselves possess intrinsic bio-activation to modulate inflammatory responses,achieving a multistage therapeutic approach that transitions from targeting to release and finally to *** approach combines anti-inflammation and neuroprotection,providing a multi-level treatment *** system was validated in a rat model of permanent middle cerebral artery occlusion (pMCAO),demonstrating that intravenous administration of the nanodelivery system repairs brain damage and improves motor function 24 h post-pMCAO *** work offers a precise and integrative strategy for stroke patients missing the acute therapy window to improve functional recovery and enhance the effect of comprehensive treatment.

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Modular assembly of complex C-alkyl glycoside enabled via cooperative NHC and photoredox catalysis

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Science China Chemistry 2025年

作者： Rui-Qiang Jiao Ming Li Xi Chen Mei-Ze Xu Tian Ding Xiao-Ping Gong Zhuo-Mei Li Xue-Yuan Liu Yong-Min Liang State Key laboratory of Applied Organic Chemistry Lanzhou University College of Chemistry and chemical Engineering Northwest Normal University

C-Alkyl glycosides are found in natural products and are indispensable in drug development programs,owing to their diverse range of medicinal ***-component reactions involving glycosyl radical addition are well documented and proved efficient for the C-alkyl glycosides ***,multicomponent reactions for the rapid and controllable construction of structurally diversified C-alkyl glycosides in a single step remains a significant challenge due to the issues associated with balancing reactivity,compatibility,and ***,we report an NHC and photoredox co-catalyzed three-component method to access complex and valuable C-alkyl *** protocol exhibits broad substrate scope and excellent chemoand ***,nine types of sugars are compatible with this *** addition,the generality of this catalytic strategy was further highlighted by the potential for scalable production,the feasibility of further modifications of the products and its successful application in the late-stage functionalization of pharmaceutical skeletons.

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Theranostical application of nanomedicine for treating central nervous system disorders

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Science China(Life Sciences) 2018年第4期61卷 392-399页

作者： Wang Ran Xue Xue State Key laboratory of medicinal chemical biology and College of Pharmacy Nankai University

The primary reason for the failure of traditional medicine in treating the disorders of the central nervous system(CNS) is the obstruction to traverse the blood-brain barrier(BBB). Due to the unique physiochemical properties of nanoparticles, they can preferably help deliver drugs passing through the BBB. Researchers have been investigating the capacity of multifunctional nanomaterials as theranostical agents. However, some of the studies have reported controversial results, which might be due to different schematic designs, including size, surface charge, and shape. This review summarizes the applications of nanoparticles to overcome the BBB or contribute to improving the diagnostic and therapeutic effects in CNS diseases.

关键词： nanomedicine theranostical efficacy drug delivery system blood-brain barrier central nervous system

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Effects of ultrasonic-assisted extraction on bioactive compounds,volatile flavors and antioxidant activities of vine tea water extracts

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Traditional Medicine Research 2025年第1期10卷 73-81页

作者： Xiao-Long Zhou Wei-Jin Jiang Ji Yu Mao-Jun Yao Yun-Tong Li Hunan Provincial Key laboratory of Research Resource Mining and High-valued Utilization on Edible&Medicinal PlantCollege of Chemistry and Chemical EngineeringJishou UniversityJishou 416000China Hunan Gaoge Dairy Co. Ltd.Changsha 410000China

Background:Ampelopsis grossedentata,vine tea,which is the tea alternative beverages in *** vine tea processing,a large amount of broken tea is produced,which has low commercial ***:This study investigates the influence of different extraction methods(room temperature water extraction,boiling water extraction,ultrasonic-assisted room temperature water extraction,and ultrasonic-assisted boiling water extraction,referred to as room temperature water extraction(RE),boiling water extraction(BE),ultrasonic assistance at room temperature water extraction(URE),and ultrasonic assistance in boiling water extraction(UBE))on the yield,dihydromyricetin(DMY)content,free amino acid composition,volatile aroma components,and antioxidant properties of vine tea ***:A notable influence of extraction temperature on the yield of vine tea extracts(P<0.05),with BE yielding the highest at 43.13±0.26%,higher than that of RE(34.29±0.81%).Ultrasound-assisted extraction significantly increased the DMY content of the extracts(P<0.05),whereas DMY content in the RE extracts was 59.94±1.70%,that of URE reached 66.14±2.78%.Analysis revealed 17 amino acids,with L-serine and aspartic acid being the most abundant in the extracts,nevertheless ultrasound-assisted extraction reduced total free amino acid *** chromatography-mass spectrometry analysis demonstrated an increase in the diversity and quantity of compounds in the vine tea water extracts obtained through ultrasonic-assisted ***,69 and 68 volatile compounds were found in URE and UBE extracts,which were higher than the number found in RE and BE *** vitro,antioxidant activity assessments revealed varying antioxidant capacities among different extraction methods,with RE exhibiting the highest DPPH scavenging rate,URE leading in ABTS•+free radical scavenging,and BE demonstrating superior ferric ion reducing antioxidant ***:The findings suggest that extraction methods signi

关键词： vine tea dihydromyricetin ultrasonic-assisted extraction volatile aroma components

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Antimycobacterial natural products from Moroccan medicinal plants: chemical composition, bacteriostatic and bactericidal profile of Thymus satureioides and Mentha pulegium essential oils

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Asian Pacific Journal of Tropical Biomedicine 2016年第10期6卷 836-840页

作者： Marwa Chraibi Abdellah Farah Sara Lebrazi Oumaima El Amine Mohammed Iraqui Houssaini Kawtar Fikri-Benbrahim laboratory of Microbial Biotechnology Faculty of Science and Technology Sass Sidi Mohamed Ben Abdellah University laboratory of Aromatic Plants Medicinal and Natural Substances National Institute of Medicinal and Aromatic PlantsPhytochemistry Department

Objective: To evaluate the susceptibility of Mycobacterium aurum and Mycobacterium smegmatis in vitro to the essential oils obtained from two medicinal plants: Thymus satureioides(T. satureioides) and Mentha pulegium(M. pulegium), and to study their chemical ***: The aerial parts of T. satureioides and M. pulegium(leaves and stems) were hydro-distillated using a Clevenger-type apparatus and essential oils were analyzed and identified by gas chromatography-mass spectrometry. Antimycobacterial screening of essential oils was performed on the basis of the inhibition zone diameter by disc diffusion method against two mycobacterial strains whereas the minimal inhibitory concentration and minimal bactericidal concentration were determined by using the micro-dilution ***: chemical analysis of their aerial part's essential oils gave as major compounds,borneol(34.26%), carvacrol(31.21%) and thymol(3.71%) for T. satureioides and R(+)-pulegone(75.48%), carvone(6.66%) and dihydrocarvone(4.64%) for M. *** their antimycobacterial effect evaluation, using the micro-dilution method,indicated that minimal inhibitory concentration values of T. satureioides essential oil ranged from 0.062% to 0.015%(v/v) and from 0.125% to 0.031%(v/v) for M. pulegium respectively against Mycobacterium aurum and Mycobacterium ***: It is clearly evident from the results obtained that the Moroccan medicinal plants have great potential to be used as anti-tuberculosis agents. These findings may help scientists to undertake several research projects to discover useful natural product as new anti-tuberculosis drug.

关键词： Thymus satureioides Mentha pulegium Essential oil chemical composition Antimycobacterial activity

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Visualization of α_1-adrenergic receptors with phenylpiperazine-based fluorescent probes

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Science China Chemistry 2016年第5期59卷 624-628页

作者： Yuxing Lin Wenhua Li Qinying Yu Xinyang Zhou Wei Zhang Lupei Du Minyong Li Key laboratory of chemical biology (Ministry of Education) Department of medicinal Chemistry School of Pharmacy Shandong University

Several novel fluorescent probes targeting α_1-adrenergic receptors were well designed and synthesized by conjugating phenylpiperazine pharmacophore with coumarin and fluorescein fluorophores. These compounds showed suitable fluorescence property, high receptor affinity, and low cytotoxicity. Moreover, the cell imaging results displayed that these probes can be effective tools for the real-time detection of ligand-receptor interactions, as well as the visualization and location of α_1-adrenergic receptors in living cells.

关键词： α1-adrenergic receptors fluorescent probes high affinity fluorescent imaging

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Bifunctional fluorescent probes for hydrogen peroxide and diols based on a 1,8-naphthalimide fluorophore

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Science China Chemistry 2013年第10期56卷 1440-1445页

作者： SUN Wei MA Zhao LI Jing LI WenHua DU LuPei LI MinYong Department of medicinal Chemistry Key Laboratory of Chemical Biology (MOE) School of Pharmacy Shandong University

This report discloses a series of naphthalimide-based bifunctional fluorescent probes for hydrogen peroxide and *** a result,these molecules not only demonstrated high turn-on fluorescent response and good selectivity towards hydrogen peroxide over other relevant reactive oxygen species,but also displayed different responses to ***,these fluorescent probes could be served as sensitive,selective and practical chemosensors for both hydrogen peroxide and diols under physiologicallike conditions.

关键词： 1,8-naphthalimide bifunctional fluorescent probe hydrogen peroxide diols

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Synthesis and screening of novel inositol phosphonate derivatives for anticancer functions in vitro

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Chinese chemical Letters 2015年第3期26卷 329-333页

作者： Wen-Bin Chen Jian-Bing Liu Dao-Lei Dou Fan-Bo Song Lu-Yuan Li Zhen Xi State Key laboratory of Elemento-Organic Chemistry Department of Chemical BiologyNankai University State Key laboratory of medicinal chemical biology College of PharmacyNankai University

Phosphonates have been frequently used as suitable isosteric and isoelectronic replacements for biologically important phosphates in the development of drugs or drug candidates because of their stability toward the action of phosphatases and other *** this paper,12 mono-phosphonate inositol compounds were prepared with phosphonate instead of phosphate by two kinds of strategies,nucleophilic substitution and Arbuzov rearrangement,*** compounds were evaluated in vitro for their activity against non-small cell lung cancer（NSCLC） cell line *** compounds（3ac and 3bb） exhibited good antitumor activity at 10 mg/mL.

关键词： phosphonate inositol toward anticancer screening instead biologically antitumor dissolved hydroxyl

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