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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-HIM 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： natural products cyclopropane-containing cyclobutane-containing biological activity biosynthetic pathway

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 *** discovery of a range of alkaloids in the early1800s,including strychnine,morphine,etc.,her... 详细信息

关键词： alkaloids moving compounds

Two New Cytotoxic Sesquiterpenoids from Eupatorium lindleyanum DC.

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Journal of Integrative Plant Biology 2006年第4期48卷 473-477页

作者： Jun Huo Sheng-Ping Yang jian Ding jian-min yue State Key Laboratory of Drug Research Institute of Materia Medica Shanghai Institute for Biological Sciences the Chinese Academy of Sciences Shanghai 201203 China

Two new sesqulterpenold lactones, namely eupallnllides K and L, were isolated from Eupatorlum Ilndleyanum DC. Their structures were determined by spectral methods, Including 1 D-and 2D-NMR spectra. Cytotoxlc evaluatlon showed that eupallnlllde L exhibited potent cytotoxlclty against P-388 and A-549 tumor cell lines with IC50 values of 0.17 and 2.60 p, mol/L, respectively.

关键词： eupalinilides K and L Eupatorium lindleyanum sesquiterpenoid

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 *** structures were elucidated by a combination of diverse methods,especially the extensive spectroscopic data analysis and electric circular dichroism(ECD)*** 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

Natural products inspired[3+2]cycloaddition enables efficient construction of hydroxylated tetrahydrofuran acetals and concise syntheses of lignans

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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 *** studies on the mechanism disclosed a concerted but asynchronous Michael addition/aldol *** 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 *** 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

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,*** 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 *** structural elucidation was achieved by the comprehensive analysis of spectroscopic data,single-crystal X-ray diffraction,and ECD *** biosynthetic pathways for compounds 1 and 2 are *** 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

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 *** 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 *** 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

Amphiphilic drug-drug conjugate for cancer therapy with combination of chemotherapeutic and antiangiogenesis drugs

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Science China Chemistry 2020年第1期63卷 35-41页

作者： Mo Sun Qiuhui Qian Leilei Shi Li Xu Qunfang Liu Linzhu Zhou Xinyuan Zhu jian-min yue Deyue Yan School of Chemistry and Chemical Engineering State Key Laboratory of Metal Matrix CompositesShanghai Jiao Tong UniversityShanghai 200240China State Key Laboratory of Drug Research Shanghai Institute of Materia MedicaChinese Academy of SciencesShanghai 201203China

The progression and metastasis of solid tumors strongly rely on the process of forming nascent blood ***,using angiogenesis inhibitors alone does not meet the cancer treatment ***,we used the amphiphilic drug-drug conjugate(ADDC)strategy to fabricate a new drug conjugate with the combination of chemotherapeutic drug and antiangiogenesis drug *** one-step esterification of hydrophilic floxuridine(FUDR)and hydrophobic pseudolaric acid B(PAB),the conjugate was *** amphiphilic property of FUDR-PAB conjugate induced the self-assembly to form nanoparticles in *** further in vitro and in vivo experiments,this FUDR-PAB conjugate does not only have a high antitumor effect,but also shows efficient antianiogenesis *** results offer a promising ADDC strategy for designing drugs with combination of chemotherapeutic drug and antiangiogenesis drug together.

关键词： nanoparticle combination therapy cancer treatment supramolecular chemistry

Highly Aromatic Norditerpenoid Heterodimers and Monomers from Trigonostemon fragilis

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Engineering 2024年第7期38卷 144-154页

作者： Jun-Su Zhou Long Cheng Yuan Gao Zhan-Peng Ge Bin Zhou Jing-Ya Li 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

Four new norditerpenoid heterodimers with different dimerization patterns-namely,trigofragiloids A-C(denoted as compounds 1-3)and(+)-and(-)-trigofragiloid D(compound 4)-and three new phenanthrenone norditerpenoids-namely,trigofragiloids E-G(compounds 5-7)-were isolated from Trigonostemon *** 1 and 2 feature a novel heterodimeric carbon skeleton formed by the conjugation of a tetra-norditerpenoid and an ennea-norditerpenoid;they have been identified as class 2 atropisomers by means of quantum chemical *** 3 is an unprecedented phenylpropanoid-norditerpenoid adduct with a new dimerization ***(+)-and(-)-4 are the first example of S-shaped 1,4-dioxane-fused norditerpenoid *** by the structure elucidation of compound 4,two co-occurring analogues,actephilol A and epiactephilol A,were structurally revised as a pair of geometrical isomers and were identified as two pairs of enantiomers,(+)-and(-)-8 and(+)-and(-)-9,*** structures were characterized using a combined ***,compound 7 exhibits remarkable adenosine triphosphate-citrate lyase(ACLY)inhibition with a halfmaximal inhibition concentration(IC50)value of(0.46±0.11)lmol·L^(-1),as active as the positive control BMS-303141,and a molecular docking study offers deep insight into the interaction between compound 7 and ACLY.

关键词： Norditerpenoid heterodimer Trigonostemon fragilis Euphorbiaceae Trigofragiloid Structural revision Adenosine triphosphate-citrate lyase(ACLY) inhibitory activity