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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01期 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.

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A reporter gene system for screening inhibitors of Wnt signaling pathway

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Natural Products and Bioprospecting 2013年第1期3卷 24-28页

作者： Xing-Yao LI yuan-yuan WANG chun-mao yuan Xiao-Jiang HAO Yan LI State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of SciencesKunming 650201YunnanChina University of Chinese Academy of Sciences Beijing 100049China School of Marine Science and Technology Harbin Institute of Technology at WeihaiShandong 264209China

Abnormal activation of canonical Wnt signaling has been associated with various types of *** reagents targeting the Wnt signaling have great potential to inhibit the growth of relevant *** we generated a cell-based screening strategy for identification of antagonists of the Wnt/β-catenin signaling *** expression wnt3a was generated in HEK293 cell line,which harbors dual-luciferase *** Wnt signaling in the stably transfected cell line was proved to be very sensitive to(-)-epigallocatechin-3-gallate(EGCG)and lithium chloride(LiCl)treatment,*** compounds were screened and a couple of novel inhibitory modulators of the Wnt signaling pathway were obtained.

关键词： Wnt signaling natural compounds dual-luciferase reporter tumor

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Five quinolizidine alkaloids with anti-tobacco mosaic virus activities from two species of Sophora

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Chinese Chemical Letters 2024年第6期35卷 380-384页

作者： Ji Zhang Tong Zhang Qiao An Peng Zhang Cai-Yan Tian chun-mao yuan Ping Yi Zhan-Xing Hu Xiao-Jiang Hao State Key Laboratory of Functions and Applications of Medicinal Plants Guizhou Medical UniversityGuiyang 550014China Natural Products Research Center of Guizhou Province Guiyang 550014China School of Pharmaceutical Sciences Guizhou Medical UniversityGuiyang 550025China School of Pharmacy Guizhou University of Traditional Chinese MedicineGuiyang 550025China State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of ScienceKunming 650201China Research Unit of Chemical Biology of Natural Anti-Virus Products Chinese Academy of Medical SciencesKunming 650201China

Three novel matrine-type alkaloids(1-3)and two unprecedented aloperine-type alkaloids(4 and 5)were isolated from the root of Sophora tonkinensis and the seeds of Sophora alopecuroides ***,compound 1 possessed an unprecedented 6/5/6 tricyclic skeleton,while compounds 2 and 3 characterized by rare 6/6/5/6 tetracyclic system and 6/6/6/6/6 pentacyclic system ***,compound 4 possessed an unprecedented 6/7/6/6 tetracyclic core,and compound 5 characterized by rare 6/6/6/6tetracyclic *** structures were elucidated by comprehensive spectroscopic data analysis and electronic circular dichroism(ECD)*** tests indicated that compound 5 displayed significant anti-tobacco mosaic virus(TMV)activity compared with the positive control ningnanmycin.

关键词： Matrine-type alkaloids Aloperine-type alkaloids Sophora tonkinensis Sophora alopecuroides Anti-tobacco mosaic virus

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Hypermonones A-I,New Polyprenylated Acylphloroglucinols from Hypericum monogynum with Multidrug Resistance Reversal Activity

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Chinese Journal of Chemistry 2021年第9期39卷 2422-2432页

作者： Yan-Rong Zeng Ya-Nan Li Jue Yang Ping Yi Lei Huang Lie-Jun Huang Wei Gu Zhan-Xing Hu Yan-Mei Li chun-mao yuan Xiao-Jiang Hao State Key Laboratory of Functions and Applications of Medicinal Plants Guizhou Medical UniversityGuiyangGuizhou 550014China The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences GuiyangGuizhou 550014China State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of SciencesKunmingYunnan 650201China

Eleven biogenetically related polyprenylated acylphloroglucinols(PPAPs),including four novel skeletons(1-4)and five new com-pounds(5-9),were isolated from the flowers of Hypericum *** A-D(1-4)represented the first example of a unique dilactone structure containing carbonyl bonded single 5-lactone and tricyclic γ-lactone *** structures were elucidated by NMR analysis,X-ray crystallography,and ECD ***,we revised the structure of hyperibrin B to hy perm on one I(9)via NMR an alysis,a qua ntum computational chemistry method,and hypothetic bios yn thetic con *** compounds(5,6,and 9)with significant MDR reversal activity(RF ranging from 61 to 223)were superior to the positive control verapamil(MCF-7/ADR,RF:53;HepG2/ADRz RF:124).Mechanism study for compound 5 indicated that this compound could inhibit the function of P-gp tran sport rather tha n its expressi on,and the possible recog nition mechanism betwee n compo und 5 and P-gp was predicted by molecular docking.

关键词： Hypericum monogynum Phytochemistry Structure elucidation Biological activity Multidrug resistance reversal activity

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Five new limonoids isolated from Walsura robusta

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Natural Products and Bioprospecting 2023年第1期13卷 657-664页

作者： Li Hou Cui-Xuan Mei chun-mao yuan Gui-Hua Tang Duo-Zhi Chen Qing Zhao Hong-Ping He Ming-Ming Cao Xiao-Jiang Hao State Key Laboratory of Photochemistry and Plant Resources in West China and Yunnan Key Laboratory of Natural Medicinal ChemistryKunming Institute of BotanyChinese Academy of SciencesKunming 650201China School of Ethnic Medicine and School of Chinese Materia MedicalYunnan University of Chinese MedicineKunming 650500China University of Chinese Academy of Sciences Beijing 100049China Bureau of Commerce and Market Supervision of Management Committee of Hunan Xiangjiang New Area Changsha 410205China The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences Guiyang 550014China Research Unit of Chemical Biology of Natural Anti-Virus Products Chinese Academy of Medical SciencesBeijing 100730China Yunnan Characteristic Plant Extraction Laboratory Kunming 650106China

Five new toosendanin limonoids with highly oxidative furan ring walsurobustones A-D(1-4),and one new furan ring degraded limonoid walsurobustone E(5)together with one known compound toonapubesic acid B(6)were isolated from the leaves of Walsura *** structures were elucidated by NMR and MS ***,the absolute configuration of toonapubesic acid B(6)was confirmed by X-ray diffraction *** 1-6 exhibited good cytotoxicity against the cancer cell lines HL-60,SMMC-7721,A-549,MCF-7,and SW480.

关键词： Limonoids Tetranortriterpenoids Walsura robusta Cytotoxicity

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Two new tirucallane triterpenoids from Aphanamixis grandifolia

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Natural Products and Bioprospecting 2012年第5期2卷 222-226页

作者： Xiao-Ying WANG Gui-Hua TANG chun-mao yuan Yu ZHANG Li HOU Qing ZHAO Xiao-Jiang HAO Hong-Ping HE State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of SciencesKunming 650201China Faculty of Pharmacy Yunnan University of TCMKunming 650500China

Two new tirucallane triterpenoids,2a-ethoxy-2,3-secotirucalla-2,29-epoxy-7-ene-23-oxo-3-oic acid(1)and(23E)-2a-hydroxytirucalla-7,23,25-triene-3-one(2),along with the known 2,3-secotirucalla-2,3;2,29-diepoxy-7-ene-3,23-dione(3),were isolated from the leaves and twigs of Aphanamixis *** structures were elucidated by extensive NMR and MS data,and compound 3 was further confirmed by X-ray crystal diffraction *** activities and insecticidal activities of these three compounds were also *** 1 showed good antimicrobial activity against Staphylococcus aureus with the MIC value of 1.56μg/mL,while compounds 1 and 2 showed insecticidal activity at 100 ppm,with the corrected mortality 79.1%and 60.6%,respectively.

关键词： Aphanamixis grandifolia Meliaceae 2 3-seco-tirucallane triterpenoid bioassays

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Daphmacrodins A and B, alkaloids from Daphniphyllum macropodum

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Natural Products and Bioprospecting 2013年第1期3卷 29-32页

作者： Ming-Ming CAO Hong-Ping HE Yu-Cheng GU Qiang ZHANG Xiao-Nian LI Guo-Ying ZUO Ying-Tong DI chun-mao yuan Shun-Lin LI Yu ZHANG Xiao-Jiang HAO State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of SciencesKunming 650201China University of Chinese Academy of Sciences Beijing 100049China Syngenta Jealott’s Hill International Research CentreBracknellBerkshireRG426EYUK Northwest A&F University Yangling 712100China Research Center of Natural Medicine Clinical School of Kunming General Hospital of Chengdu Military CommandKunming 650032China

Two new daphnicyclidin-type Daphniphyllum alkaloids,daphmacrodins A and B(1 and 2)were isolated from the leaves and stems of Daphniphyllum *** structures were elucidated by extensive spectroscopic techniques,including 2D NMR spectroscopy and mass *** relative configuration of 1 was further confirmed by a single-crystal X-ray diffraction *** cytotoxic activities against five human cancer cell lines,pesticidal activities against brine shrimp(Artemia salina),and antibacterial activities against five standard bacterial and fungal strains were *** structure of 1 was successfully transformed to 2 by a chemical method.

关键词： Daphniphyllaceae Daphniphyllum macropodum cyclopentadienyl anion

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连云港市区域竞争力SWOT分析及提升对策

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淮海工学院学报（人文社会科学版） 2004年第2期2卷 38-41页

作者：毛春元淮海工学院经济管理系江苏连云港222001

运用区域竞争力理论 ,从优势 (S)、劣势 (W )、威胁 (T)、机会 (O)四个方面对连云港市区域竞争力进行了具体分析 ,全面揭示了该市区域竞争力的战略地位 ,认为该市区域竞争力在苏北处于中游水平 ,在全省处于下游水平。在此基础上 ,提出... 详细信息

运用区域竞争力理论 ,从优势 (S)、劣势 (W )、威胁 (T)、机会 (O)四个方面对连云港市区域竞争力进行了具体分析 ,全面揭示了该市区域竞争力的战略地位 ,认为该市区域竞争力在苏北处于中游水平 ,在全省处于下游水平。在此基础上 ,提出了提升连云港市区域竞争力的对策与建议。

关键词：连云港市区域竞争力 SWOT分析对策

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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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科学通报 2024年

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 SpeF and P450 monooxygenase SpeG, is identified in the biosynthesis of spiro polycyclic alkaloids(+)-notoamide B and its diastereomer(+)-versicolamide B. Using notoamide E as a substance, SpeF/SpeG metabolon can control the stereoselectivity of its 2,3-epoxidation, followed by hydrogen atom ion at C-17 to generate reactive epoxide tau-mA 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.

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蜂蛰伤致儿童中毒24例临床分析

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中国医药指南 2009年第6期7卷 28-28,27页

作者：刘兵虎春元刘春四川省巴中市人民医院儿科 636000

目的总结急性蜂毒中毒致儿童多器官功能障碍的治疗经验。方法综合分析我院1997年至2007年间急性蜂毒中毒患儿24例临床资料。结果24例患儿入院后均呈现不同程度的心、肝、肾功能损害等临床表现。结论治疗蜂毒中毒应尽早采用透析等综合性... 详细信息

目的总结急性蜂毒中毒致儿童多器官功能障碍的治疗经验。方法综合分析我院1997年至2007年间急性蜂毒中毒患儿24例临床资料。结果24例患儿入院后均呈现不同程度的心、肝、肾功能损害等临床表现。结论治疗蜂毒中毒应尽早采用透析等综合性治疗措施,保护心、肝、肾等多器官功能,促使多器官功能恢复是抢救治疗该病的关键。

关键词：急性蜂毒中毒多器官功能障碍治疗临床资料

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