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Structural diversification of chemical constituents from bryophytes and their antifungal virulent effects

Structural diversification of chemical constituents from bry...

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中国化学会第十二届全国天然有机化学学术会议

作者： Bin Sun Jiao-Zhen Zhang 娄红祥 Key Laboratory of natural products & Chemical Biology Ministry of EducationSchool of Pharmaceutical SciencesShandong University

natural products played a key role in the drug discovery.During these years,it was found that the diversification of natural products was very important for the drug development.Based on the long-term research of natural products from the bryophyte,our present investigation is to diversify bryophyte-derived compounds(such as biflavone,diterpenoids and bisbibenzyls) by chemical engineering,photo-driven chemical conversion or total synthesis.Firstly,the antifungal compounds were obtained from the bryophyte extracts efficiently by the bio-test guided separation.Secondly,the flavones in the extracts were diversified rapidly by the chemical engineering method,especially,through the reaction with hydrazine as well as its derivatives to obtain pyrazoles,or by the Mannich reaction with secondary amines to give alkaloid derivatives.Thirdly,a series of novel compounds were prepared from diterpenoides in the bryophyte by the photo-driven rearrangement or [2+2] cycloaddition.Finally,four bisbibenzyls were obtained by the total synthesis and diversified by the alkylation,Mannich reaction or bromination.All these novel derivatives were assayed by the method based on the virulence factors-targeting,which was related to the formation of hyphae,biofilm and drug resistance in the invasion process.

关键词： Diversification Antifungal activity natural products Chemical engineering Photo-driven chemical conversion

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Screening of Jumonji domain-containing protein 3 inhibitors innatural products by capillary electrophoresis

Screening of Jumonji domain-containing protein 3 inhibitors ...

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中国化学会第22届全国色谱学术报告会及仪器展览会

作者： Yi Zhang Jingwu Kang State Key Laboratory of Bio-organic and natural products Chemistry Center for Excellence in Molecular Synthesis Shanghai Institute of OrganicChemistry University of Chinese Academy of Sciences Chinese Academy of Sciences

＜正＞Jumonji domain-containing protein 3（JMJD3/KDM6 B） plays an important role intheepigeneticregulation of gene expression.Its abnormal expressioncan be observed in the progression ofa variety of diseases, such as... 详细信息

关键词： KDM6B inhibitor natural products capillary electrophoresis

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Total Synthesis of Hamigerans

Total Synthesis of Hamigerans

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中国化学会第十四届全国有机合成化学学术研讨会

作者： Xiaojun Li Dongsheng Xue Cheng Wang Shuanhu Gao Shanghai Key Laboratory of Green Chemistry and Chemical Processes School of Chemistry and Molecular Engineering East China Normal University

The hamigerans are a novel bioactive family of metabolites isolated from the poecilosclerid sponge Hamigeratarangaensis. These natural products generally contain a unique 5-6-6 or 5-7-6 tricarbocyclic core structure in which contains three or four contiguous stereogenic centers.Due to the unique structures and interesting biological activity,hamigerans attracted a considerable attention from synthetic chemists.Our group firstly finished the total synthesis of hamigerans G and its biomimetic transformation to hamigerans L,D and N-Q. A convergent approach was used to build the basic 5-6-6 structure.The key steps include an acid promoted semipinacol rearrangement to construct the cyclopentane ring A,Suzuki-Miyaura cross-coupling reaction to connect A-C ring and Mc Murry coupling reaction to generate the basic 5-6-6 tricarbocyclic skeleton.A sequence of oxidative cleavage,homologation and ring regeneration enabled the access of 5-7-6 skeleton of hamigeran G.Based on the biogenetic hypothesis,biomimetic transformations of hamigeran G to hamigerans D,N-Q and L were achieved with high efficiency and elegancy.

关键词： biomimetic synthesis cross-couplings heterocycles natural products total synthesis

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Chiral Agrochemicals Based on Succinate Dehydrogenase

Chiral Agrochemicals Based on Succinate Dehydrogenase

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中国化学会第一届农业化学学术讨论会

作者： Dangdang Li Wei Li Zehua Song Shengkun Li Nanjing Agricultural University

With the optimal efficacy, increased selectivity and favorable toxicological and environmental safety, discovery of novel chiral agrochemicals is one of most elegant approaches to green plant protection. We are engaged in the synthetic methodologies and structure optimization of biologically important chiral molecules potentially targeting Succinate Dehydrogenase（SDH, the complex II in ETC）, including drimane meroterpenoids and β-arylamine alkaloids.（1） Structure optimization of β-arylamines and drimane meroterpenoids was carried out for novel leads. Dearomatization and bioactivity-guided mixed synthesis were conceived and implemented for lead optimization in the discovery of new antifungal candidates.（2） Asymmetric catalytic methodologies and decarboxylative coupling were developed for the acquirement of β-aryl amines and drimane meroterpenoids, respectively. The concept of multifunctional ligands was proposed and implemented.（3） Novel and high efficient approaches were established for the synthesis of agrochemicals and drugs that structurally related to the aforementioned pesticides, new insights into the biological performance of the antifungal candidates were also acquired.

关键词： Chiral Agrochemicals Succinate Dehydrogenase Asymmetric Synthesis natural products

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Deciphering gliotoxin biosynthesis in Aspergillus fumigatus

Deciphering gliotoxin biosynthesis in Aspergillus fumigatus

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多彩菌物美丽中国——中国菌物学会2019年学术年会

作者： Daniel H Scharf Department of Microbiology and Parasitology Collaborative Innovation Center for Diagnosis and Treatment of Infectious Diseases School of Medicine Zhejiang University

Gliotoxin is the prototype of the infamous family of ETP（epi-dithiodiketopiperazine） toxins that are produced by a wide range of microorganisms. A hallmark of ETPs is the cyclopeptide scaffold equipped with a transannular disulfide bridge. This outstanding structural unit is indeed responsible for deleterious effects of the toxins as it readily mediates intracellular redox-cycling and inactivates vital proteins by conjugation. Endowed with these adverse properties, gliotoxin significantly contributes to the virulence of the human pathogen Aspergillus fumigatus. Notably, invasive aspergillosis caused by this fungus is the leading cause for death in immunocompromized patients. Since knowledge of the molecular basis and enzymology of ETP biosynthesis could greatly aid in developing diagnostics and antifungal therapy, this area has been the focus of intense research over the past years. Using various methods stemming from molecular biology, structural biology, biochemistry,and organic chemistry, I was able to present a virtually complete model of this biosynthetic pathway. Gliotoxin’s biosynthesis revealed enzymes that catalyze some truly fascinating reactions.

关键词： Gliotoxin natural products virulence factor

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Development and Application of Virtual Screening and Medical Biostatistics Methods in Oncology Drug Development and Precision Medicine

Development and Application of Virtual Screening and Medical...

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2019中国化学会第十五届全国计算（机）化学学术会议

作者：黄遵楠广东医科大学

This presentation involved in the development and application of virtual screening methods to aid the design of bioactive compounds in oncology drug development as well as medical biostatistics methods to study the complicated genetics and disease associations in precision medicine. In the first half, we began with the development of an effective method to determine the good protein structures for receptor-based virtual screening or ensemble docking a priori without evaluating the ability of each conformation to discriminate between known ligands and non-ligands. Then we briefly reviewed reverse screening methods to search for protein targets of chemopreventive compounds and computational approaches in preclinical studies for in silico ADMET prediction. After that, we showed to apply those computational screening methods to design the small molecular inhibitors of tumor proteins such as TRAF6 and RSK2. In the second half, we started with the development of a standard stratification method to control for confounding factors and reveal their interactions in genetic association meta-analysis. Then we introduced several advanced meta-analysis works with emphasizing on the application of stratified analysis, relative predispositional effect method, hierarchical correlation graphs, and genetic inheritance models to clarify the associations between the common tumors and their susceptibility genes.

关键词： Virtual Screening Drug Design natural products Meta-analysis Stratification Analysis

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Application of hydrophilic interaction chromatography in natural product analysis

Application of hydrophilic interaction chromatography in nat...

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中华中医药学会第七次中药分析学术交流会

作者： Yan Gao Yi Luo Ru-Feng Wang Bin Liu School of Chinese Medicine Beijing University of Chinese Medicine

Recently,the hydrophilic interaction chromatography(HILIC) developed rapidly for highly polar compounds with good separation and have drawn more highly focused on natural products isolation areas.In this paper,to describe HILIC mobile phase、 stationary phase and its application in NPs analysis,for the purpose of providing a reference for the polar compounds separation and the NPs application.

关键词： hydrophilic interaction chromatography natural products separation highly polar compounds

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Chemical Biology Study Based on the natural ’Probes’ From Traditional Chinese Medicines

Chemical Biology Study Based on the Natural ’Probes’ From ...

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第五届全国化学生物学学术会议

作者： Samuel X.Qiu Chemistry Department of Washington University in St.Louis,St.Louis,USA.,and Kunming Institute of Botany,CAS,Kunming,Yunnan,China

＜正＞In biological systems,function and malfunction ultimately originate from interacting,rather than isolated, molecules.As such,most cellular processes are carried out by multiprotein complexes,and the organization of the assembly of expressed proteins into functional units result in complex protein interaction networks.The depth of understanding of biological systems has been largely determined by the availability of tools that can be used to

关键词： Chemical Biology natural products bioprobes Cancer Inflammation

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Me2AlSEt-Promoted Domino Dieckmann Cyclization Enables the Total Synthesis of Polycyclic Polyprenylated Acylphloroglucinols

Me2AlSEt-Promoted Domino Dieckmann Cyclization Enables the T...

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中国化学会·第十六届全国有机合成化学学术研讨会

作者： Liping Wang Lian Sun Xueying Wang 郑昌武 School of Pharmacy Shanghai University of Traditional Chinese Medicineand Engineering Research Center of Shanghai Colleges for TCM New Drug Discovery 上海中医药大学

A bioinspired,MeAlSEt-promoted domino Dieckmann cyclization was developed for the syntheses of nine polycyclic polyprenylated acylphloroglucinols(PPAPs).This novel domino cyclization tolerates a series of congested linear precursors decorated with prenyl or bulky geranyl groups,providing a very efficient way of Dieckmann reaction with sterically hindered substrates.The mechanism,stereoselectivity and advantages of this strategy were investigated and demonstrated.A diversity-oriented synthesis featuring a divergent synthetic pathway towards a range of homo-and hetero-substituted linear precursors was also developed.A late-stage C-acylation with a bulky aryl group was also explored and modified under Lewis acidic conditions.Moreover,the cytotoxicities of the synthesized PPAPs and related analogues were evaluated,leading to the identification of three simplified potent antitumor agents.

关键词： PPAPs Dieckmann condensation total synthesis structure-activity relationships natural products

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