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The chemical structures,biosynthesis,and biological activities of secondary metabolites from the culinary-medicinal mushrooms of the genus Hericium:a review

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Chinese Journal of natural Medicines 2024年第8期22卷 676-698页

作者： QI Jianzhao WU Jing KANG Shijie GAO Jingming Hirokazu Kawagishi LIU Hongwei LIU Chengwei key laboratory for Enzyme and Enzyme-Like Material Engineering of Heilongjiang College of Life ScienceNortheast Forestry UniversityHarbin 150040China Shaanxi key laboratory of natural products&chemical biology College of Chemistry&PharmacyNorthwest A&F UniversityYangling 712100China Faculty of Agriculture Shizuoka UniversityShizuoka 422-8529Japan State key laboratory of Mycology Institute of MicrobiologyChinese Academy of SciencesBeijing 100101China

Fungal phytochemicals derived from higher fungi,particularly those from the culinary-medicinal genus Hericium,have gained significant attention in drug discovery and *** review aims to provide a comprehensive analysis of the chemical structures,biosynthetic pathways,biological activities,and pharmacological properties of monomeric compounds isolated from Hericium *** the past 34 years,253 metabolites have been identified from various Hericium species,including cyathane diterpenes,alkaloids,benzofurans,chromenes,phenols,pyrones,steroids,and other miscellaneous *** investigations into the biosynthesis of erinacines,a type of cyathane diterpene,have led to the discovery of novel cyathane *** research has highlighted the biological activities and pharmacological properties of Hericium-derived compounds,with particular emphasis on their neuroprotective and neurotrophic effects,immunomodulatory capabilities,anti-cancer activity,antioxidant properties,and antimicrobial *** A,in particular,has been extensively ***,transcriptomic,and proteomic analyses of Hericium species have facilitated the discovery of new compounds and provided insights into enzymatic reactions through genome *** diverse chemical structures and biological activities of Hericium compounds underpin their potential applications in medicine and as dietary *** review not only advances our understanding of Hericium compounds but also encourages further research into Hericium species within the realms of medicine,health,functional foods,and agricultural *** broad spectrum of compound types and their diverse biological activities present promising opportunities for the development of new pharmaceuticals and edible products.

关键词： Hericium Secondary metabolites Biological activity Biosynthesis

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Rearranged 19-nor-7,8-seco-labdane diterpenoids and Diels-Alder cycloadducts from the Chinese liverwort Pallavicinia ambigua:Structural elucidation,photoinduced rearrangement,and cytotoxic activity

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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 *** structures were identified via combined analysis of their spectroscopic data,single-crystal X-ray diffraction patterns,and ECD *** 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

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One stone three birds:Ni-catalyzed asymmetric allenylic substitution of allenic ethers,hydroalkylation of 1,3-enynes and double alkylation of enynyl ethers

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Chinese chemical Letters 2024年第8期35卷 282-287页

作者： Zhirong Yang Shan Wang Ming Jiang Gengchen Li Long Li Fangzhi Peng Zhihui Shao key laboratory of Medicinal Chemistry for natural Resource Ministry of EducationSchool of Chemical Science and TechnologyYunnan Provincial Center for Research&Development of Natural Productsand State Key Laboratory for Conservation and Utilization of Bio-Resources in YunnanYunnan UniversityKunming 650091China

The development of low-cost,earth-abundant and environmentally benign transition metal catalysts,which can catalyze multiple different types of asymmetric reactions,is an important objective in mod-ern asymmetric *** we demonstrate that a chiral Ni/P-Phos catalyst achieves three types of asymmetric reactions:allenylic substitution of racemic allenic ethers,1,4-hydroalkylation of prochiral 1,3-enynes and double alkylation of newly designed enynyl ether *** methods complement each other and produce various axially chiral allene derivatives bearing a pyrazolidine-3,5-dione unit,which is widely present in drugs and biologically active molecules with versatile pharmacological activities.

关键词： Nickel Asymmetric catalysis Allenylic substitution Hydroalkylation Double alkylation Allene 1,3-Enyne Pyrazolidine-3,5-dione

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Hericium erinaceus: the enchanting medicinal-culinary mushroom of East Asian tradition

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Integrative Medicine Discovery 2024年第13期8卷 1-2页

作者： Jian-Zhao Qi Shaanxi key laboratory of natural products&chemical biology College of Chemistry&PharmacyNorthwest A&F UniversityXianyang 712100China

Hericium mushrooms,a type of fungi imbued with mystical connotations in traditional East Asian diet and medicine,hold a prestigious position as the foremost among the“eight treasures of the mountain”in China,earning them the moniker“mountain delicacies and marine flavors.”As traditional medicinal fungi,Hericium mushrooms are renowned for their brain-boosting and cognitive-enhancing *** erinaceus(***)is the leading variety of Hericium mushrooms and has been cultivated on a large *** addition,some new species such as the Hericium coralloides,Hericium alpestre,and Hericium rajendrae have been progressively discovered and documented[1,2].The recent pursuit of health and nutrition has propelled this nutrient-rich and bioactive mushroom into the *** article explores the traditional uses of Hericium mushrooms,the chemical structures and biological activities of their secondary metabolites,as well as the pivotal role of omics technologies in this field(Figure 1).

关键词： properties Figure boosting

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A multi-enzymatic cascade reaction for the synthesis of bioactive C-oligosaccharides

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Chinese chemical Letters 2024年第6期35卷 451-455页

作者： Kebo Xie Qian Zhang Fei Ye Jungui Dai State key laboratory of Bioactive Substance and Function of natural Medicines CAMS Key Laboratory of Enzyme and Biocatalysis of Natural Drugs and NHC Key Laboratory of Biosynthesis of Natural ProductsInstitute of Materia MedicaChinese Academy of Medical Sciences and Peking Union Medical CollegeBeijing 100050China

C-Oligosaccharides are rare in nature and possess diverse ***,their chemical synthesis faces many *** this work,enzymatic introduction of C-linked sugar chains to target aglycones was successfully achieved by multi-enzymatic cascade reactions.A C-glycosyltransferase from Aloe barbadensis was employed to introduce the first C-linked glucose and then a cyclomaltodextrin glucanotransferase from Bacillus licheniformis was used to extend the sugar chain.A total of twenty C-oligosaccharides with 2-6 sugars were synthesized from scale-up reactions and exhibited good water solubility and sodium-dependent glucose transporter 2(SGLT2)inhibitory ***,a glucoamylase was used to control the length of the sugar chain and the C-maltosides were efficiently *** findings not only expanded the structural diversity of C-oligosaccharides,but also provided a strategy for the modification of C-glycoside drugs to improve the druggability.

关键词： C-Oligosaccharides C-Glycosyltransferase Cyclomaltodextrin glucanotransferase Glucoamylase Enzymatic synthesis SGLT2 inhibitory activity

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A fungal CYP from Beauveria bassiana with promiscuous steroid hydroxylation capabilities

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Chinese chemical Letters 2024年第5期35卷 218-222页

作者： Yu Peng Yue Wang Tian-Jiao Chen Jing-Jing Chen Jin-Ling Yang Ting Gong Ping Zhu State key laboratory of Bioactive Substance and Function of natural Medicines NHC Key Laboratory of Biosynthesis of Natural ProductsCAMS Key Laboratory of Enzyme and Biocatalysis of Natural DrugsInstitute of Materia MedicaChinese Academy of Medical Sciences&Peking Union Medical CollegeBeijing 100050China

Hydroxylation of steroid core is critical to the synthesis of steroid *** sp^(3) C-H hydroxylation is challenging through chemical catalysis,alternatively,fungal biotransformation offers a possible solution to this ***,mining and metabolic engineering of cytochrome P450 monooxygenases(CYPs)is usually regarded as a more eco-friendly and efficient ***,we report the mining and identification of a new steroid CYP(CYP68BE1)from Beauveria bassiana by transcriptomics,heterologous expression,in vivo and in vitro functional *** catalytic promiscuity of CYP68BE1 was explored,and CYP68BE1 showed promiscuously and catalytically versatile,which is qualified for monohydroxylation on C11α,C1α,C6βand dihydroxylation on C1β,11αand C6β,11αof six steroids,leading to the production of key steroid intermediates required in the industrial synthesis of some indispensable steroid *** dynamics simulations were performed,revealing the molecular basis of different binding orientations of CYP68BE1 with different *** discovery of CYP68BE1 offers a promising biocatalyst for enriching the steroid structural and functional diversity,which also can be applied to biosynthesize valuable steroid drug intermediates.

关键词： Fungal CYPs Steroid hydroxylase Beauveria bassiana Promiscuous biocatalyst Molecular dynamics

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Revealing the Multifunctional Electrocatalysis of Indium-Modulated Phthalocyanine for High-Performance Lithium-Sulfur Batteries

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Energy & Environmental Materials 2024年第1期7卷 1-8页

作者： Yang Guo Zhaoqing Jin Jianhao Lu Zilong Wang Zihao Song Anbang Wang Weikun Wang Yaqin Huang Beijing key laboratory of Electrochemical Process and Technology for Materials Key Laboratory of Biomedical Materials of Natural MacromoleculesMinistry of EducationBeijing University of Chemical TechnologyBeijing 100029China Research Institute of chemical Defense Beijing Key Laboratory of Advanced Chemical Energy Storage Technology and MaterialsBeijing 100191China

The sluggish kinetics of complicated multiphase conversions and the severe shuttling effect of lithium polysulfides(LiPSs)significantly hinder the applications of Li-S battery,which is one of the most promising candidates for the next-generation energy storage ***,a bifunctional electrocatalyst,indium phthalocyanine self-assembled with carbon nanotubes(InPc@CNT)composite material,is proposed to promote the conversion kinetics of both reduction and oxidation processes,demonstrating a bidirectional catalytic effect on both nucleation and dissolution of Li_(2)S *** theoretical calculation shows that the unique electronic configuration of InPc@CNT is conducive to trapping soluble polysulfides in the reduction process,as well as the modulation of electron transfer dynamics also endows the dissolution of Li_(2)S in the oxidation reaction,which will accelerate the effectiveness of catalytic conversion and facilitate sulfur ***,the InPc@CNT modified separator displays lower overpotential for polysulfide transformation,alleviating polarization of electrode during *** integrated spectroscopy analysis,HRTEM,and electrochemical study reveal that the InPc@CNT acts as an efficient multifunctional catalytic center to satisfy the requirements of accelerating charging and discharging ***,the Li-S battery with InPc@CNT-modified separator obtains a discharge-specific capacity of 1415 mAh g^(-1)at a high rate of 0.5 ***,the 2 Ah Li-S pouch cells deliver 315 Wh kg^(-1)and achieved 80%capacity retention after 50 cycles at 0.1 C with a high sulfur loading of 10 mg cm^(-2).Our study provides a practical method to introduce bifunctional electrocatalysts for boosting the electrochemical properties of Li-S batteries.

关键词： bidirectional catalyst indium phthalocyanine lithium-sulfur batteries pouch cells

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Applications of genetic code expansion technology in eukaryotes

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Protein & Cell 2024年第5期15卷 331-363页

作者： Qiao-ru Guo Yu J.Cao State key laboratory of chemical Oncogenomic Guangdong Provincial Key Laboratory of Chemical GenomicsPeking University Shenzhen Graduate SchoolShenzhen 518055China Institute of chemical biology Shenzhen Bay LaboratoryShenzhen 518132China

Unnatural amino acids(UAAs)have gained significant attention in protein engineering and drug development owing to their ability to introduce new chemical functionalities to *** eukaryotes,genetic code expansion(GCE)enables the incorporation of UAAs and facilitates posttranscriptional modification(PTM),which is not feasible in prokaryotic *** is also a powerful tool for cell or animal imaging,the monitoring of protein interactions in target cells,drug development,and switch ***,there is keen interest in utilizing GCE in eukaryotic *** review provides an overview of the application of GCE in eukaryotic systems and discusses current challenges that need to be addressed.

关键词： genetic code expansion unnatural amino acid eukaryotes basic research therapeutic applications

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Low-melting mixture solvents: extension of deep eutectic solvents and ionic liquids for broadening green solvents and green chemistry

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Green chemical Engineering 2024年第4期5卷 409-417页

作者： Yu Chen Zhiwu Yu MOE key laboratory of Bioorganic Phosphorous Chemistry and chemical biology Department of ChemistryTsinghua University

Green solvents such as water and ionic liquids(ILs) are pillars of the great mansion of green chemistry and green processing. Initially proposed as a new family of ILs,deep eutectic solvents(DESs) have received fast development in the past two decades. In this contribution,DESs are reviewed critically and the concept is extended to lowmelting mixture solvents(Lo MMSs),which cover all kinds of materials including ionic compounds,molecular compounds,and metals. Six classes of Lo MMSs are proposed as the new classification system and examples are given. Finally,several thermodynamic issues concerning Lo MMSs are discussed. Two new concepts,robustness of Lo MMSs and high-entropy Lo MMSs,are proposed.

关键词： Green solvents Deep eutectic solvents Low transition temperature mixture solvents Phase diagram EGaIn

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Nickel-catalyzed enantioselective reductive amination of benzylic ketones in alcohols

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Science China Chemistry 2024年第8期67卷 2566-2570页

作者： Xiuhua Wang Jianrong Steve Zhou State key laboratory of chemical Oncogenomics School of Chemical Biology and BiotechnologyPeking University Shenzhen Graduate SchoolShenzhen 518055China

Asymmetric reductive amination directly converts ketones and amines to alkylamines, which are important motifs in *** report that cationic nickel complexes of chiral diphosphines promote enantioselective reductive amination of benzylic ketones with both arylamines and benzhydrazide. Isopropanol was used as a safe and cheap source of hydrogen instead of formic acid. The reaction can be readily applied to a concise synthesis of diarylethylamines, a class of neuroactive substances.

关键词： transfer hydrogenation nickel catalysis chiral alkylamine reductive amination synthetic method

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