New 3,5-dimethylorsellinic acid-based meroterpenoids with BACE1 and AchE inhibitory activities from Aspergillus terreus

Chemical investigation of the extracts of Aspergillus terreus resulted in the identification of terreusterpenes A-D (1-4), four new 3,5-dimethylorsellinic acid-based meroterpenoids. The structures and absolute configurations of 1-4 were elucidated by spectroscopic analyses including HRESIMS and 1D-...

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Veröffentlicht in:Organic & biomolecular chemistry 2018-11, Vol.16 (46), p.9046-9052
Hauptverfasser: Qi, Changxing, Qiao, Yuben, Gao, Weixi, Liu, Mengting, Zhou, Qun, Chen, Chunmei, Lai, Yongji, Xue, Yongbo, Zhang, Jinwen, Li, Dongyan, Wang, Jianping, Zhu, Hucheng, Hu, Zhengxi, Zhou, Yuan, Zhang, Yonghui
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container_issue 46
container_start_page 9046
container_title Organic & biomolecular chemistry
container_volume 16
creator Qi, Changxing
Qiao, Yuben
Gao, Weixi
Liu, Mengting
Zhou, Qun
Chen, Chunmei
Lai, Yongji
Xue, Yongbo
Zhang, Jinwen
Li, Dongyan
Wang, Jianping
Zhu, Hucheng
Hu, Zhengxi
Zhou, Yuan
Zhang, Yonghui
description Chemical investigation of the extracts of Aspergillus terreus resulted in the identification of terreusterpenes A-D (1-4), four new 3,5-dimethylorsellinic acid-based meroterpenoids. The structures and absolute configurations of 1-4 were elucidated by spectroscopic analyses including HRESIMS and 1D- and 2D-NMR, chemical conversion, and single crystal X-ray diffraction. Terreusterpenes A (1) and B (2) featured 2,3,5-trimethyl-4-oxo-5-carboxy tetrahydrofuran moieties. Terreusterpene D (4) was characterized by a 4-hydroxy-3-methyl gamma lactone fragment that was generated by accident from the rearrangement of 3 in a mixed tetrahydrofuran-H2O-MeOH solvent. All these compounds were evaluated for the β-site amyloid precursor protein-cleaving enzyme 1 (BACE1) and acetylcholinesterase (AchE) inhibitory activities. Among them, compounds 1 and 2 showed potentially significant BACE1 inhibitory activity, with IC50 values of 5.98 and 11.42 μM, respectively. Interestingly, compound 4 exhibited promising BACE1 and AchE inhibitory activities, with IC50 values of 1.91 and 8.86 μM, respectively, while 3 showed no such activity. Taken together, terreusterpenes A and B could be of great importance for the development of new BACE1 inhibitors, while terreusterpene D could serve as the first dual-targeted 3,5-dimethylorsellinic acid-based meroterpenoid for the treatment of Alzheimer's disease.
doi_str_mv 10.1039/c8ob02741b
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The structures and absolute configurations of 1-4 were elucidated by spectroscopic analyses including HRESIMS and 1D- and 2D-NMR, chemical conversion, and single crystal X-ray diffraction. Terreusterpenes A (1) and B (2) featured 2,3,5-trimethyl-4-oxo-5-carboxy tetrahydrofuran moieties. Terreusterpene D (4) was characterized by a 4-hydroxy-3-methyl gamma lactone fragment that was generated by accident from the rearrangement of 3 in a mixed tetrahydrofuran-H2O-MeOH solvent. All these compounds were evaluated for the β-site amyloid precursor protein-cleaving enzyme 1 (BACE1) and acetylcholinesterase (AchE) inhibitory activities. Among them, compounds 1 and 2 showed potentially significant BACE1 inhibitory activity, with IC50 values of 5.98 and 11.42 μM, respectively. Interestingly, compound 4 exhibited promising BACE1 and AchE inhibitory activities, with IC50 values of 1.91 and 8.86 μM, respectively, while 3 showed no such activity. 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The structures and absolute configurations of 1-4 were elucidated by spectroscopic analyses including HRESIMS and 1D- and 2D-NMR, chemical conversion, and single crystal X-ray diffraction. Terreusterpenes A (1) and B (2) featured 2,3,5-trimethyl-4-oxo-5-carboxy tetrahydrofuran moieties. Terreusterpene D (4) was characterized by a 4-hydroxy-3-methyl gamma lactone fragment that was generated by accident from the rearrangement of 3 in a mixed tetrahydrofuran-H2O-MeOH solvent. All these compounds were evaluated for the β-site amyloid precursor protein-cleaving enzyme 1 (BACE1) and acetylcholinesterase (AchE) inhibitory activities. Among them, compounds 1 and 2 showed potentially significant BACE1 inhibitory activity, with IC50 values of 5.98 and 11.42 μM, respectively. Interestingly, compound 4 exhibited promising BACE1 and AchE inhibitory activities, with IC50 values of 1.91 and 8.86 μM, respectively, while 3 showed no such activity. 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inhibitors</subject><subject>GPI-Linked Proteins - metabolism</subject><subject>Humans</subject><subject>Medical treatment</subject><subject>Models, Molecular</subject><subject>Molecular Docking Simulation</subject><subject>Neurodegenerative diseases</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Organic chemistry</subject><subject>Proteins</subject><subject>Resorcinols - chemical synthesis</subject><subject>Resorcinols - chemistry</subject><subject>Resorcinols - pharmacology</subject><subject>Single crystals</subject><subject>Tetrahydrofuran</subject><subject>X ray spectra</subject><subject>X-ray diffraction</subject><subject>β-Site APP-cleaving enzyme 1</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkUtPwzAQhC0E4n3hByBLXBAiYMd2bB_bqjwkBBc4R46zpkZJXOyEqv-elNeB0-7hm9HuDEInlFxRwvS1VaEiueS02kL7lEuZEcH09t-ekz10kNIbIVTLgu-iPUY4I1TKfbR6hBVmlyKrfQv9Yt2EmKBpfOctNtbXWWUS1LiFGHqIS-iCrxNe-X6Bp5PZnGLT1XhiF3Psu4WvfB_iehT2_sP3HhJ2MbR4kpYQX33TDAmPLhGGdIR2nGkSHP_MQ_RyM3-e3WUPT7f3s8lDZpko-oyDhhycoABa64rlAoSzhXWFcg6sEZoXkjJpgVmljSuM48YSoBUboxGKHaLzb99lDO8DpL5sfbLjh6aDMKQyp4ypXEilR_TsH_oWhtiN120opSTjmo_UxTdlY0gpgiuX0bcmrktKyk0d5Uw9Tb_qmI7w6Y_lULVQ_6G_-bNPjK2GKQ</recordid><startdate>20181128</startdate><enddate>20181128</enddate><creator>Qi, Changxing</creator><creator>Qiao, Yuben</creator><creator>Gao, Weixi</creator><creator>Liu, Mengting</creator><creator>Zhou, Qun</creator><creator>Chen, Chunmei</creator><creator>Lai, Yongji</creator><creator>Xue, Yongbo</creator><creator>Zhang, Jinwen</creator><creator>Li, Dongyan</creator><creator>Wang, Jianping</creator><creator>Zhu, Hucheng</creator><creator>Hu, Zhengxi</creator><creator>Zhou, Yuan</creator><creator>Zhang, Yonghui</creator><general>Royal Society of Chemistry</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-8881-1232</orcidid><orcidid>https://orcid.org/0000-0002-6672-0014</orcidid><orcidid>https://orcid.org/0000-0001-9133-6439</orcidid><orcidid>https://orcid.org/0000-0003-4272-9003</orcidid><orcidid>https://orcid.org/0000-0002-7222-2142</orcidid><orcidid>https://orcid.org/0000-0002-1247-5615</orcidid></search><sort><creationdate>20181128</creationdate><title>New 3,5-dimethylorsellinic acid-based meroterpenoids with BACE1 and AchE inhibitory activities from Aspergillus terreus</title><author>Qi, Changxing ; Qiao, Yuben ; Gao, Weixi ; Liu, Mengting ; Zhou, Qun ; Chen, Chunmei ; Lai, Yongji ; Xue, Yongbo ; Zhang, Jinwen ; Li, Dongyan ; Wang, Jianping ; Zhu, Hucheng ; Hu, Zhengxi ; Zhou, Yuan ; Zhang, Yonghui</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c356t-4e9e2ef51ee999b325e5fc6cf68ffeca59467137ce3c89af6af4ac0e1b3103583</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Acetylcholinesterase</topic><topic>Acetylcholinesterase - metabolism</topic><topic>Acids</topic><topic>Alzheimer Disease - drug therapy</topic><topic>Alzheimer Disease - metabolism</topic><topic>Alzheimer's disease</topic><topic>Amyloid precursor protein</topic><topic>Amyloid Precursor Protein Secretases - antagonists &amp; inhibitors</topic><topic>Amyloid Precursor Protein Secretases - metabolism</topic><topic>Aspartic Acid Endopeptidases - antagonists &amp; inhibitors</topic><topic>Aspartic Acid Endopeptidases - metabolism</topic><topic>Aspergillus - chemistry</topic><topic>Aspergillus terreus</topic><topic>Cholinesterase Inhibitors - chemical synthesis</topic><topic>Cholinesterase Inhibitors - chemistry</topic><topic>Cholinesterase Inhibitors - pharmacology</topic><topic>Crystallography</topic><topic>Crystallography, X-Ray</topic><topic>GPI-Linked Proteins - antagonists &amp; inhibitors</topic><topic>GPI-Linked Proteins - metabolism</topic><topic>Humans</topic><topic>Medical treatment</topic><topic>Models, Molecular</topic><topic>Molecular Docking Simulation</topic><topic>Neurodegenerative diseases</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Organic chemistry</topic><topic>Proteins</topic><topic>Resorcinols - chemical synthesis</topic><topic>Resorcinols - chemistry</topic><topic>Resorcinols - pharmacology</topic><topic>Single crystals</topic><topic>Tetrahydrofuran</topic><topic>X ray spectra</topic><topic>X-ray diffraction</topic><topic>β-Site APP-cleaving enzyme 1</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Qi, Changxing</creatorcontrib><creatorcontrib>Qiao, Yuben</creatorcontrib><creatorcontrib>Gao, Weixi</creatorcontrib><creatorcontrib>Liu, Mengting</creatorcontrib><creatorcontrib>Zhou, Qun</creatorcontrib><creatorcontrib>Chen, Chunmei</creatorcontrib><creatorcontrib>Lai, Yongji</creatorcontrib><creatorcontrib>Xue, Yongbo</creatorcontrib><creatorcontrib>Zhang, Jinwen</creatorcontrib><creatorcontrib>Li, Dongyan</creatorcontrib><creatorcontrib>Wang, Jianping</creatorcontrib><creatorcontrib>Zhu, Hucheng</creatorcontrib><creatorcontrib>Hu, Zhengxi</creatorcontrib><creatorcontrib>Zhou, Yuan</creatorcontrib><creatorcontrib>Zhang, Yonghui</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic &amp; biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Qi, Changxing</au><au>Qiao, Yuben</au><au>Gao, Weixi</au><au>Liu, Mengting</au><au>Zhou, Qun</au><au>Chen, Chunmei</au><au>Lai, Yongji</au><au>Xue, Yongbo</au><au>Zhang, Jinwen</au><au>Li, Dongyan</au><au>Wang, Jianping</au><au>Zhu, Hucheng</au><au>Hu, Zhengxi</au><au>Zhou, Yuan</au><au>Zhang, Yonghui</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>New 3,5-dimethylorsellinic acid-based meroterpenoids with BACE1 and AchE inhibitory activities from Aspergillus terreus</atitle><jtitle>Organic &amp; biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2018-11-28</date><risdate>2018</risdate><volume>16</volume><issue>46</issue><spage>9046</spage><epage>9052</epage><pages>9046-9052</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>Chemical investigation of the extracts of Aspergillus terreus resulted in the identification of terreusterpenes A-D (1-4), four new 3,5-dimethylorsellinic acid-based meroterpenoids. The structures and absolute configurations of 1-4 were elucidated by spectroscopic analyses including HRESIMS and 1D- and 2D-NMR, chemical conversion, and single crystal X-ray diffraction. Terreusterpenes A (1) and B (2) featured 2,3,5-trimethyl-4-oxo-5-carboxy tetrahydrofuran moieties. Terreusterpene D (4) was characterized by a 4-hydroxy-3-methyl gamma lactone fragment that was generated by accident from the rearrangement of 3 in a mixed tetrahydrofuran-H2O-MeOH solvent. All these compounds were evaluated for the β-site amyloid precursor protein-cleaving enzyme 1 (BACE1) and acetylcholinesterase (AchE) inhibitory activities. Among them, compounds 1 and 2 showed potentially significant BACE1 inhibitory activity, with IC50 values of 5.98 and 11.42 μM, respectively. Interestingly, compound 4 exhibited promising BACE1 and AchE inhibitory activities, with IC50 values of 1.91 and 8.86 μM, respectively, while 3 showed no such activity. Taken together, terreusterpenes A and B could be of great importance for the development of new BACE1 inhibitors, while terreusterpene D could serve as the first dual-targeted 3,5-dimethylorsellinic acid-based meroterpenoid for the treatment of Alzheimer's disease.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>30430177</pmid><doi>10.1039/c8ob02741b</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0002-8881-1232</orcidid><orcidid>https://orcid.org/0000-0002-6672-0014</orcidid><orcidid>https://orcid.org/0000-0001-9133-6439</orcidid><orcidid>https://orcid.org/0000-0003-4272-9003</orcidid><orcidid>https://orcid.org/0000-0002-7222-2142</orcidid><orcidid>https://orcid.org/0000-0002-1247-5615</orcidid></addata></record>
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source MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects Acetylcholinesterase
Acetylcholinesterase - metabolism
Acids
Alzheimer Disease - drug therapy
Alzheimer Disease - metabolism
Alzheimer's disease
Amyloid precursor protein
Amyloid Precursor Protein Secretases - antagonists & inhibitors
Amyloid Precursor Protein Secretases - metabolism
Aspartic Acid Endopeptidases - antagonists & inhibitors
Aspartic Acid Endopeptidases - metabolism
Aspergillus - chemistry
Aspergillus terreus
Cholinesterase Inhibitors - chemical synthesis
Cholinesterase Inhibitors - chemistry
Cholinesterase Inhibitors - pharmacology
Crystallography
Crystallography, X-Ray
GPI-Linked Proteins - antagonists & inhibitors
GPI-Linked Proteins - metabolism
Humans
Medical treatment
Models, Molecular
Molecular Docking Simulation
Neurodegenerative diseases
NMR
Nuclear magnetic resonance
Organic chemistry
Proteins
Resorcinols - chemical synthesis
Resorcinols - chemistry
Resorcinols - pharmacology
Single crystals
Tetrahydrofuran
X ray spectra
X-ray diffraction
β-Site APP-cleaving enzyme 1
title New 3,5-dimethylorsellinic acid-based meroterpenoids with BACE1 and AchE inhibitory activities from Aspergillus terreus
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