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Science China Chemistry 2024年第7期67卷 2306-2313页

作者： Dong-yue Cai Weiming Shi Zhao-Hui Jin Zhi-Xiang Yu Jin-Xin Zhao jian-min yue State Key Laboratory of Drug Research Shanghai Institute of Materia MedicaChinese Academy of SciencesShanghai 201203China University of Chinese Academy of Sciences Beijing 100049China Beijing National Laboratory for Molecular Sciences(BNLMS) Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of EducationCollege of ChemistryPeking UniversityBeijing 100871China

Mimicking biosynthetic pathways of hongkonoids led to the development of a new Cu(Ⅰ)-catalyzed[3+2]cycloaddition ofα-hydroxyketone andβ-keto enol ethers,affording tetrahydrofuran acetals in a highly diastereoselective manner and 100%atom economy.Computational studies on the mechanism disclosed a concerted but asynchronous Michael addition/aldol reaction.Of the same importance,this methodology provides a practical biomimetic approach for one-step construction of the dibenzylbutyrolactol lignan backbone starting from two phenyl propane derivatives,opening up a powerful new approach for lignan synthesis,which is showcased by succinct total syntheses of two biologically important aryltetralin-type lignans,β-apopicropodophyllin and cycloolivil.Given the mild and operationally simple conditions,the developed chemistry might have a promising prospect in potential industrial applications.

关键词： [3+2]cycloaddition transition-metal catalysis tetrahydrofuran lignans natural products

Natural products are the treasure pool for antimalarial agents

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National Science Review 2022年第11期9卷 11-13页

作者： Bin Zhou jian-min yue State Key Laboratory of Drug Research Shanghai Institute of Materia Medica Chinese Academy of Sciences

The history of mankind is a constant struggle against diseases, and humans have learned to use natural sources as the remedies to alleviate and/or treat diseases since prehistoric times.e structural diversity and comp... 详细信息

关键词： MALARIA

Frontier studies on natural products:moving toward paradigm shifts

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Science China Chemistry 2023年第4期66卷 928-942页

作者： Jin-Xin Zhao jian-min yue State Key Laboratory of Drug Research Shanghai Institute of Materia MedicaChinese Academy of SciencesShanghai 201203China Shandong Laboratory of Yantai Drug Discovery Bohai Rim Advanced Research Institute for Drug DiscoveryYantai 264117China

1 Introduction Natural products(NPs)historically serve as a valuable and productive source of bioactive compounds for drug development.The discovery of a range of alkaloids in the early1800s,including strychnine,morph... 详细信息

关键词： alkaloids moving compounds

Suadimins D—J,Monoterpenoid Indole-Quinoline and Bisindole Alkaloids from Melodinus suaveolens

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Chinese Journal of Chemistry 2023年第18期41卷 2296-2304页

作者： Xin-Hua Gao Pei-Qian Wu Yao-yue Fan Bin Zhou jian-min yue State Key Laboratory of Drug Research Shanghai Institute of Materia MedicaChinese Academy of Sciences555 Zuchongzhi RoadShanghai201203China shandong Laboratory of Yantai Drug Discovery Bohai Rim Advanced Research Institute for Drug DiscoveryYantaiShandong 264117China Research Units of Discovery of New Drug Lead Molecules Chinese Academy of Medical SciencesShanghai 201203China

Comprehensive Summary,Compounds 1—12,including seven complex monoterpenoid indole-quinoline and bisindole alkaloids,suadimins D—J(1—7)with previously unreported carbon-carbon linkages,were isolated and identified from the twigs and leaves of Melodinus suaveolens.Their structures were elucidated by a combination of diverse methods,especially the extensive spectroscopic data analysis and electric circular dichroism(ECD)calculations.The cytotoxicity of these compounds against three cancer cell lines was evaluated,some of which showed moderate activities with IC50 values ranging from 2.4 to 8.0μM.

关键词： Melodinus suaveolens Alkaloids Dimerization Structure elucidation ECD calculations Cytotoxic activity

Concise Total Synthesis of Dysoxylactam A and a Simplified Analog

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Chinese Journal of Chemistry 2022年第17期40卷 2027-2034页

作者： Guan-Zhou Yang Lei Wang Yao-yue Fan Zeng-Wei Lai Xue-Ni Yu Li-Guang Lou Kun Gao jian-min yue State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical EngineeringLanzhou University222 Tianshui South RoadLanzhouGansu730000 China State Key Laboratory of Drug Research Shanghai Institute of Materia MedicaChinese Academy of Sciences555 Zuchongzhi RoadShanghai201203 China University of Chinese Academy of Sciences No.19A Yuquan RoadBeijing100049 China

A total synthesis of 17-membered macrocyclolipopeptide dysoxylactam A,a potent agent reversing P-glycoprotein(P-gp)-mediated multidrug resistance(MDR)in cancer cells,was developed from the starting material(S)-2-methylbutanal in a linear sequence of 12 steps with 23.2%overall yield.The key steps include proline-catalyzed asymmetric aldol reaction,Evans aldol reaction and Krische allylation to construct the multiple stereocenters containing fragment,and ring-closing metathesis to furnish the macrocycle.This total synthesis facilitates the preparation of large amount samples of dysoxylactam A and the side chain simplified derivatives for further biological tests and preliminary structure-activity relationship exploration.

关键词： Total synthesis Dysoxylactam A Macrocyclolipopeptide Reversing multidrug resistance Structure-activity relationship

Two Terpenoid Derivatives with Different 3/5/6/6/5-Fused Pentacyclic Skeletons from Hedyosmum orientale

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Chinese Journal of Chemistry 2023年第4期41卷 392-398页

作者： Yao-yue Fan Cheng-Yu Zheng Bin Zhou Flavia M.Zimbres Maria B.Cassera jian-min yue State Key Laboratory of Drug Research Shanghai Institute of Materia MedicaChinese Academy of Sciences555 Zuchongzhi RoadShanghai201203 China Shandong Laboratory of Yantai Drug Discovery Bohai Rim Advanced Research Institute for Drug DiscoveryYantaiShandong264117 China Research Units of Discovery of New Drug Lead Molecules Chinese Academy of Medical SciencesShanghai201203 China Department of Biochemistry and Molecular Biology Center for Tropical and Emerging Global Diseases(CTEGD)University of GeorgiaAthensGeorgia30602 United States

Chemical investigation of Hedyosmum orientale led to the identification of two terpenoid derivatives,dyosmunoids A and B(1 and 2)featuring two different 3/5/6/6/5-fused pentacyclic ring systems,respectively.Compound 1 is the second natural product of this C_(25) terpenoid compound class,and compound 2 is a rare dinor-C25 terpenoid with a peroxide bridge.Their structural elucidation was achieved by the comprehensive analysis of spectroscopic data,single-crystal X-ray diffraction,and ECD calculation.Putative biosynthetic pathways for compounds 1 and 2 are proposed.Compound 2 exhibited strong antimalarial activity with an IC_(50) value of 0.42μmol·L^(-1).

关键词： Natural products C_(25)Terpenoids Structure elucidation Biosynthetic pathway hypothesis Antimalarial activity

A new class of potent liver injury protective compounds: Structural elucidation, total synthesis and bioactivity study

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Acta Pharmaceutica Sinica B 2023年第8期13卷 3414-3424页

作者： Kailong Ji Wei Liu Weihang Yin Xiangrong Kong Honghong Xu Zeng-Wei Lai Jing-Ya Li jian-min yue State Key Laboratory of Drug Research Shanghai Institute of Materia MedicaChinese Academy of SciencesShanghai 201203China School of Chinese Materia Medica Nanjing University of Chinese MedicineNanjing 210023China

A new class of potent liver injury protective compounds,phychetins A-D(1-4)featuring an unique 6/6/5/6/5 pentacyclic framework,were isolated and structurally characterized from a Chinese medicinal plant Phyllanthus franchetianus.Compounds 2-4 are three pairs of enantiomers that were initially obtained in a racemic manner,and were further separated by chiral HPLC preparation.Compounds 1-4 were proposed to be originated biosynthetically from a coexisting lignan via an intramolecular Friedel-Crafts reaction as the key step.A bioinspired total synthesis strategy was thus designated,and allowed the effective syntheses of compounds 2-4 in high yields.Some of compounds exhibited significant anti-inflammatory activities in vitro via suppressing the production of pro-inflammatory cytokine IL-1β.Notably,compound 4,the most active enantiomeric pair in vitro,displayed prominent potent protecting activity against liver injury at a low dose of 3 mg/kg in mice,which could serve as a promising lead for the development of acute liver injury therapeutic agent.

关键词： Phychetins Phyllanthusfranchetianus Structural elucidation Total synthesis Liver injury protection Anti-inflammation

Rearranged Dichapetalin-Type Triterpenoids with Cytotoxic Activity from Dichapetalum gelonioides

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Chinese Journal of Chemistry 2022年第21期40卷 2531-2538页

作者： Xin-Hua Gao Xi-Yuan Wang Jun-Su Zhou Yan Zhang Hong-Chun Liu Bin Zhou jian-min yue State Key Laboratory of Drug Research Shanghai lnstitute of Materia MedicaChinese Academy of SciencesShanghai 201203China Research Units of Discovery of New Drug Lead Molecules Chinese Academy of Medical SciencesShanghai 201203china Shandong Laboratory of Yantai Drug Discovery Bohai Rim Advanced Research Institute for Drug DiscoveryYantaiShandong 264117China

Dichagelinoids A—C(1—3),three unusual dichapetalin-type triterpenoids,together with two biogenetically related derivatives dichagelinoids D and E(4 and 5)were isolated and characterized by solid data from Dichapetalum gelonioides.Compounds 1—3 possess a common rearranged C ring and different C6—C2 modified motifs at the A rings.Biological evaluation revealed that compounds 1—3 showed distinct cytotoxic activity against the tested human cancer cell lines.

关键词： Dichapetalum gelonioides Natural products Dichapetalin-type triterpenoids Structural elucidation Cytotoxic activity

Cephalotane-Type Norditerpenoids from Cephalotaxus fortunei var.alpina

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Chinese Journal of Chemistry 2022年第10期40卷 1177-1184页

作者： Zhan-Peng Ge Bin Zhou Flavia M.Zimbres Maria B.Cassera Jin-Xin Zhao jian-min yue State Key Laboratory of Drug Research Shanghai Institute of Materia MedicaChinese Academy of Sciences555 Zuchongzhi RoadShanghai 201203China Department of Biochemistry and Molecular Biology Center for Tropical and Emerging Global Diseases(CTEGD)University of GeorgiaAthensGeorgia30602UnitedStates

A chemical investigation of the 95%EtoH extract of the seeds of Cephalotaxus fortunei var.alpina led to the isolation of nine new cephalotane-type norditerpenoids,ceforalides A-I(1-9),and two known analogues(10 and 11).Compounds 1-8 belong to a rare class of A-ring-contracted cephalotane-type norditerpenoids,of which compound 8 incorporates a unique tetrasubstituted 2,5-cyclohexadienone A-ring.Compound 9 is a rare 13,14-seco-17-nor-cephalotane-type diterpenoid.Their structures were determined based on NMR,HRESIMS,ECD,and X-ray diffraction analysis.Biological tests revealed compounds 10 and 11 displayed moderate antimalarial activity.

关键词： Cephalotaxus fortunei var.alpine Natural products Structural elucidation Cephalotane norditerpenoids I Antimalarial activity

Attractive natural products with strained cyclopropane and/or cyclobutane ring systems

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Science China Chemistry 2016年第9期59卷 1126-1141页

作者： Yao-yue Fan Xin-Hua Gao jian-min yue Shanghai Institute of Materia Medica Chinese Academy of Sciences

The strained cyclopropane and/or cyclobutane subunits occurred in many complex natural products including terpenoids, steroids and alkaloids. Natural products with cyclopropane and/or cyclobutane motifs not only furnished fascinating structures, but also exhibited versatile biological activities, such as cytotoxic, anti-HIV, antimicrobial, antiviral, and immunosuppressive effects. This review covered a large array of structurally unique natural products with strained cyclopropane and/or cyclobutane motifs and summarized their structural features, distributions, biological activities, as well as biogenetic considerations.

关键词：天然产品环丙烷吸引力系统免疫抑制作用结构特征天然产物生物活性