An Efficient Regioselective Synthesis of 8‑Formylhomoisoflavonoids with Neuroprotective Activity by Enhancing Autophagy
6-Formylisoophiopogonone B (7a) and 8-formylophiopogonone B (7b), two natural products isolated from Ophiopogon japonicus, represent a subgroup of rare 6/8-formyl/methyl-homoisoflavonoid skeletons. Herein we report an efficient method for the synthesis of these formyl/methyl-homoisoflavonoids. The s...
Gespeichert in:
| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2021-04, Vol.84 (4), p.1385-1391 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1391 |
|---|---|
| container_issue | 4 |
| container_start_page | 1385 |
| container_title | Journal of natural products (Washington, D.C.) |
| container_volume | 84 |
| creator | Li, Jie Yang, Fan Zeng, Lin-Wei Zhang, Fang-Min Zhou, Chang-Xin Gan, Li-She |
| description | 6-Formylisoophiopogonone B (7a) and 8-formylophiopogonone B (7b), two natural products isolated from Ophiopogon japonicus, represent a subgroup of rare 6/8-formyl/methyl-homoisoflavonoid skeletons. Herein we report an efficient method for the synthesis of these formyl/methyl-homoisoflavonoids. The synthesized compounds were evaluated for their neuroprotective effects on the MPP+-induced SH-SY5Y cell injury model and showed marked activity. Exploration of the neuroprotective mechanisms of compound 7b led to an increased expression of autophagy marker LC3-II and down-regulation of autophagy substrate p62/SQSTM1. Molecular docking studies showed that 7b may prevent the inhibition of the classic PI3K-AKT-mTOR signaling pathway by interfering with the human HSP90AA1. |
| doi_str_mv | 10.1021/acs.jnatprod.0c00830 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2501851302</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2501851302</sourcerecordid><originalsourceid>FETCH-LOGICAL-a381t-2279718593d7f7426097003e236d00a23b7e3378c39645e08be7c6a8068f27423</originalsourceid><addsrcrecordid>eNqNkU1u2zAQhYkiReOkvUFQcJmN3CEpUdTSCJwmQNAC_VkLNDWyGEikK1IptOsVesWcJHTsZFl0NZv33ryZj5ALBksGnH3SJizvnY670TdLMABKwBuyYAWHTAIvTsgCmBSZUDI_JWch3AOAgKp4R06FKHkOQi7IvHJ03bbWWHSRfsOt9QF7NNE-IP0-u9hhsIH6lqrHP3-v_TjMfecHb4Nve_3gnbdNoL9t7OgXnEaf2sSje7UfNs50M9O167Qz1m3paop-1-nt_J68bXUf8MNxnpOf1-sfVzfZ3dfPt1eru0wLxWLGeVmVTBWVaMq2zLmEqkx3IBeyAdBcbEpM5ygjKpkXCGqDpZFagVQtT3pxTi4PuanarwlDrAcbDPa9duinUPOiYBXLWS7_QwqpCROwT80PUjP6EEZs691oBz3ONYN6z6dOfOoXPvWRT7J9PG6YNgM2r6YXIEkAB8Gz3U-jS7_5d-YT40WhMA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2501851302</pqid></control><display><type>article</type><title>An Efficient Regioselective Synthesis of 8‑Formylhomoisoflavonoids with Neuroprotective Activity by Enhancing Autophagy</title><source>ACS Publications</source><creator>Li, Jie ; Yang, Fan ; Zeng, Lin-Wei ; Zhang, Fang-Min ; Zhou, Chang-Xin ; Gan, Li-She</creator><creatorcontrib>Li, Jie ; Yang, Fan ; Zeng, Lin-Wei ; Zhang, Fang-Min ; Zhou, Chang-Xin ; Gan, Li-She</creatorcontrib><description>6-Formylisoophiopogonone B (7a) and 8-formylophiopogonone B (7b), two natural products isolated from Ophiopogon japonicus, represent a subgroup of rare 6/8-formyl/methyl-homoisoflavonoid skeletons. Herein we report an efficient method for the synthesis of these formyl/methyl-homoisoflavonoids. The synthesized compounds were evaluated for their neuroprotective effects on the MPP+-induced SH-SY5Y cell injury model and showed marked activity. Exploration of the neuroprotective mechanisms of compound 7b led to an increased expression of autophagy marker LC3-II and down-regulation of autophagy substrate p62/SQSTM1. Molecular docking studies showed that 7b may prevent the inhibition of the classic PI3K-AKT-mTOR signaling pathway by interfering with the human HSP90AA1.</description><identifier>ISSN: 0163-3864</identifier><identifier>ISSN: 1520-6025</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/acs.jnatprod.0c00830</identifier><identifier>PMID: 33724036</identifier><language>eng</language><publisher>United States: American Chemical Society and American Society of Pharmacognosy</publisher><subject>autophagy ; humans ; neuroprotective effect ; Ophiopogon japonicus ; regioselectivity</subject><ispartof>Journal of natural products (Washington, D.C.), 2021-04, Vol.84 (4), p.1385-1391</ispartof><rights>2021 American Chemical Society and American Society of Pharmacognosy</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a381t-2279718593d7f7426097003e236d00a23b7e3378c39645e08be7c6a8068f27423</citedby><cites>FETCH-LOGICAL-a381t-2279718593d7f7426097003e236d00a23b7e3378c39645e08be7c6a8068f27423</cites><orcidid>0000-0002-4726-9838 ; 0000-0002-5688-5894</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.jnatprod.0c00830$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.jnatprod.0c00830$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,777,781,2752,27057,27905,27906,56719,56769</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33724036$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Li, Jie</creatorcontrib><creatorcontrib>Yang, Fan</creatorcontrib><creatorcontrib>Zeng, Lin-Wei</creatorcontrib><creatorcontrib>Zhang, Fang-Min</creatorcontrib><creatorcontrib>Zhou, Chang-Xin</creatorcontrib><creatorcontrib>Gan, Li-She</creatorcontrib><title>An Efficient Regioselective Synthesis of 8‑Formylhomoisoflavonoids with Neuroprotective Activity by Enhancing Autophagy</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>6-Formylisoophiopogonone B (7a) and 8-formylophiopogonone B (7b), two natural products isolated from Ophiopogon japonicus, represent a subgroup of rare 6/8-formyl/methyl-homoisoflavonoid skeletons. Herein we report an efficient method for the synthesis of these formyl/methyl-homoisoflavonoids. The synthesized compounds were evaluated for their neuroprotective effects on the MPP+-induced SH-SY5Y cell injury model and showed marked activity. Exploration of the neuroprotective mechanisms of compound 7b led to an increased expression of autophagy marker LC3-II and down-regulation of autophagy substrate p62/SQSTM1. Molecular docking studies showed that 7b may prevent the inhibition of the classic PI3K-AKT-mTOR signaling pathway by interfering with the human HSP90AA1.</description><subject>autophagy</subject><subject>humans</subject><subject>neuroprotective effect</subject><subject>Ophiopogon japonicus</subject><subject>regioselectivity</subject><issn>0163-3864</issn><issn>1520-6025</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqNkU1u2zAQhYkiReOkvUFQcJmN3CEpUdTSCJwmQNAC_VkLNDWyGEikK1IptOsVesWcJHTsZFl0NZv33ryZj5ALBksGnH3SJizvnY670TdLMABKwBuyYAWHTAIvTsgCmBSZUDI_JWch3AOAgKp4R06FKHkOQi7IvHJ03bbWWHSRfsOt9QF7NNE-IP0-u9hhsIH6lqrHP3-v_TjMfecHb4Nve_3gnbdNoL9t7OgXnEaf2sSje7UfNs50M9O167Qz1m3paop-1-nt_J68bXUf8MNxnpOf1-sfVzfZ3dfPt1eru0wLxWLGeVmVTBWVaMq2zLmEqkx3IBeyAdBcbEpM5ygjKpkXCGqDpZFagVQtT3pxTi4PuanarwlDrAcbDPa9duinUPOiYBXLWS7_QwqpCROwT80PUjP6EEZs691oBz3ONYN6z6dOfOoXPvWRT7J9PG6YNgM2r6YXIEkAB8Gz3U-jS7_5d-YT40WhMA</recordid><startdate>20210423</startdate><enddate>20210423</enddate><creator>Li, Jie</creator><creator>Yang, Fan</creator><creator>Zeng, Lin-Wei</creator><creator>Zhang, Fang-Min</creator><creator>Zhou, Chang-Xin</creator><creator>Gan, Li-She</creator><general>American Chemical Society and American Society of Pharmacognosy</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7S9</scope><scope>L.6</scope><orcidid>https://orcid.org/0000-0002-4726-9838</orcidid><orcidid>https://orcid.org/0000-0002-5688-5894</orcidid></search><sort><creationdate>20210423</creationdate><title>An Efficient Regioselective Synthesis of 8‑Formylhomoisoflavonoids with Neuroprotective Activity by Enhancing Autophagy</title><author>Li, Jie ; Yang, Fan ; Zeng, Lin-Wei ; Zhang, Fang-Min ; Zhou, Chang-Xin ; Gan, Li-She</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-2279718593d7f7426097003e236d00a23b7e3378c39645e08be7c6a8068f27423</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>autophagy</topic><topic>humans</topic><topic>neuroprotective effect</topic><topic>Ophiopogon japonicus</topic><topic>regioselectivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Jie</creatorcontrib><creatorcontrib>Yang, Fan</creatorcontrib><creatorcontrib>Zeng, Lin-Wei</creatorcontrib><creatorcontrib>Zhang, Fang-Min</creatorcontrib><creatorcontrib>Zhou, Chang-Xin</creatorcontrib><creatorcontrib>Gan, Li-She</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Jie</au><au>Yang, Fan</au><au>Zeng, Lin-Wei</au><au>Zhang, Fang-Min</au><au>Zhou, Chang-Xin</au><au>Gan, Li-She</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An Efficient Regioselective Synthesis of 8‑Formylhomoisoflavonoids with Neuroprotective Activity by Enhancing Autophagy</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2021-04-23</date><risdate>2021</risdate><volume>84</volume><issue>4</issue><spage>1385</spage><epage>1391</epage><pages>1385-1391</pages><issn>0163-3864</issn><issn>1520-6025</issn><eissn>1520-6025</eissn><abstract>6-Formylisoophiopogonone B (7a) and 8-formylophiopogonone B (7b), two natural products isolated from Ophiopogon japonicus, represent a subgroup of rare 6/8-formyl/methyl-homoisoflavonoid skeletons. Herein we report an efficient method for the synthesis of these formyl/methyl-homoisoflavonoids. The synthesized compounds were evaluated for their neuroprotective effects on the MPP+-induced SH-SY5Y cell injury model and showed marked activity. Exploration of the neuroprotective mechanisms of compound 7b led to an increased expression of autophagy marker LC3-II and down-regulation of autophagy substrate p62/SQSTM1. Molecular docking studies showed that 7b may prevent the inhibition of the classic PI3K-AKT-mTOR signaling pathway by interfering with the human HSP90AA1.</abstract><cop>United States</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>33724036</pmid><doi>10.1021/acs.jnatprod.0c00830</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0002-4726-9838</orcidid><orcidid>https://orcid.org/0000-0002-5688-5894</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0163-3864 |
| ispartof | Journal of natural products (Washington, D.C.), 2021-04, Vol.84 (4), p.1385-1391 |
| issn | 0163-3864 1520-6025 1520-6025 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2501851302 |
| source | ACS Publications |
| subjects | autophagy humans neuroprotective effect Ophiopogon japonicus regioselectivity |
| title | An Efficient Regioselective Synthesis of 8‑Formylhomoisoflavonoids with Neuroprotective Activity by Enhancing Autophagy |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-20T01%3A38%3A24IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=An%20Efficient%20Regioselective%20Synthesis%20of%208%E2%80%91Formylhomoisoflavonoids%20with%20Neuroprotective%20Activity%20by%20Enhancing%20Autophagy&rft.jtitle=Journal%20of%20natural%20products%20(Washington,%20D.C.)&rft.au=Li,%20Jie&rft.date=2021-04-23&rft.volume=84&rft.issue=4&rft.spage=1385&rft.epage=1391&rft.pages=1385-1391&rft.issn=0163-3864&rft.eissn=1520-6025&rft_id=info:doi/10.1021/acs.jnatprod.0c00830&rft_dat=%3Cproquest_cross%3E2501851302%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2501851302&rft_id=info:pmid/33724036&rfr_iscdi=true |