Three new meroterpenoids from Sargassum macrocarpum and their inhibitory activity against amyloid β aggregation
Amyloid β (Aβ) is thought to be involved in the pathogenesis of Alzheimer’s disease (AD). Aβ aggregation in the brain is considered the cause of AD. Therefore, inhibiting Aβ aggregation and degrading existing Aβ aggregates is a promising approach for the treatment and prevention of the disease. In s...
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Veröffentlicht in: | Journal of natural medicines 2023-06, Vol.77 (3), p.508-515 |
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creator | Shinoda, Seiya Tozawa, Yuta Kurimoto, Shin-ichiro Shigemori, Hideyuki Sekiguchi, Mitsuhiro |
description | Amyloid β (Aβ) is thought to be involved in the pathogenesis of Alzheimer’s disease (AD). Aβ aggregation in the brain is considered the cause of AD. Therefore, inhibiting Aβ aggregation and degrading existing Aβ aggregates is a promising approach for the treatment and prevention of the disease. In searching for inhibitors of Aβ42 aggregation, we found that meroterpenoids isolated from
Sargassum macrocarpum
possess potent inhibitory activities. Therefore, we searched for active compounds from this brown alga and isolated 16 meroterpenoids, which contain three new compounds. The structures of these new compounds were elucidated using two-dimensional nuclear magnetic resonance techniques. Thioflavin-T assay and transmission electron microscopy were used to reveal the inhibitory activity of these compounds against Aβ42 aggregation. All the isolated meroterpenoids were found to be active, and compounds with a hydroquinone structure tended to have stronger activity than those with a quinone structure.
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doi_str_mv | 10.1007/s11418-023-01693-y |
format | Article |
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Sargassum macrocarpum
possess potent inhibitory activities. Therefore, we searched for active compounds from this brown alga and isolated 16 meroterpenoids, which contain three new compounds. The structures of these new compounds were elucidated using two-dimensional nuclear magnetic resonance techniques. Thioflavin-T assay and transmission electron microscopy were used to reveal the inhibitory activity of these compounds against Aβ42 aggregation. All the isolated meroterpenoids were found to be active, and compounds with a hydroquinone structure tended to have stronger activity than those with a quinone structure.
Graphical abstract</description><identifier>ISSN: 1340-3443</identifier><identifier>EISSN: 1861-0293</identifier><identifier>DOI: 10.1007/s11418-023-01693-y</identifier><identifier>PMID: 36933089</identifier><language>eng</language><publisher>Singapore: Springer Nature Singapore</publisher><subject>Algae ; Alzheimer Disease - drug therapy ; Alzheimer's disease ; Amyloid ; Amyloid beta-Peptides - antagonists & inhibitors ; Biomedical and Life Sciences ; Biomedicine ; brain ; Complementary & Alternative Medicine ; Humans ; Hydroquinone ; Medicinal Chemistry ; meroterpenoids ; Metabolites ; Neurodegenerative diseases ; NMR ; Nuclear magnetic resonance ; nuclear magnetic resonance spectroscopy ; Original Paper ; Pathogenesis ; Pharmacology/Toxicology ; Pharmacy ; Plant Sciences ; quinones ; Sargassum ; Sargassum - chemistry ; Sargassum macrocarpum ; Terpenes - chemistry ; Terpenes - pharmacology ; Transmission electron microscopy</subject><ispartof>Journal of natural medicines, 2023-06, Vol.77 (3), p.508-515</ispartof><rights>Crown 2023</rights><rights>2023. Crown.</rights><rights>Crown 2023.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c383t-339e992c8e907719c2dcb29dd0e8367bdee51633863d1f096058b2755093b9ff3</cites><orcidid>0000-0001-6780-4538 ; 0000-0001-9778-8057 ; 0000-0002-7906-2866</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11418-023-01693-y$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11418-023-01693-y$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,41464,42533,51294</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36933089$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Shinoda, Seiya</creatorcontrib><creatorcontrib>Tozawa, Yuta</creatorcontrib><creatorcontrib>Kurimoto, Shin-ichiro</creatorcontrib><creatorcontrib>Shigemori, Hideyuki</creatorcontrib><creatorcontrib>Sekiguchi, Mitsuhiro</creatorcontrib><title>Three new meroterpenoids from Sargassum macrocarpum and their inhibitory activity against amyloid β aggregation</title><title>Journal of natural medicines</title><addtitle>J Nat Med</addtitle><addtitle>J Nat Med</addtitle><description>Amyloid β (Aβ) is thought to be involved in the pathogenesis of Alzheimer’s disease (AD). Aβ aggregation in the brain is considered the cause of AD. Therefore, inhibiting Aβ aggregation and degrading existing Aβ aggregates is a promising approach for the treatment and prevention of the disease. In searching for inhibitors of Aβ42 aggregation, we found that meroterpenoids isolated from
Sargassum macrocarpum
possess potent inhibitory activities. Therefore, we searched for active compounds from this brown alga and isolated 16 meroterpenoids, which contain three new compounds. The structures of these new compounds were elucidated using two-dimensional nuclear magnetic resonance techniques. Thioflavin-T assay and transmission electron microscopy were used to reveal the inhibitory activity of these compounds against Aβ42 aggregation. All the isolated meroterpenoids were found to be active, and compounds with a hydroquinone structure tended to have stronger activity than those with a quinone structure.
Graphical abstract</description><subject>Algae</subject><subject>Alzheimer Disease - drug therapy</subject><subject>Alzheimer's disease</subject><subject>Amyloid</subject><subject>Amyloid beta-Peptides - antagonists & inhibitors</subject><subject>Biomedical and Life Sciences</subject><subject>Biomedicine</subject><subject>brain</subject><subject>Complementary & Alternative Medicine</subject><subject>Humans</subject><subject>Hydroquinone</subject><subject>Medicinal Chemistry</subject><subject>meroterpenoids</subject><subject>Metabolites</subject><subject>Neurodegenerative diseases</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>nuclear magnetic resonance spectroscopy</subject><subject>Original Paper</subject><subject>Pathogenesis</subject><subject>Pharmacology/Toxicology</subject><subject>Pharmacy</subject><subject>Plant Sciences</subject><subject>quinones</subject><subject>Sargassum</subject><subject>Sargassum - chemistry</subject><subject>Sargassum macrocarpum</subject><subject>Terpenes - chemistry</subject><subject>Terpenes - pharmacology</subject><subject>Transmission electron microscopy</subject><issn>1340-3443</issn><issn>1861-0293</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkcFu1TAQRS1ERUvhB1ggS2y6CbU9cWIvUQUtUiUWlLXlJJM8Vy92sB2q_BYfwjfh9hWQWMBqrmbOXMtzCXnF2VvOWHueOK-5qpiAivFGQ7U9ISdcNby0NDwtGmpWQV3DMXme0i1jtQDgz8gxFBqY0idkudlFROrxjs4YQ8a4oA9uSHSMYaafbZxsSutMZ9vH0Nu4FG39QPMOXaTO71zncogbtX1231wuYrLOp0ztvO2LE_3xvbSmiJPNLvgX5Gi0-4QvH-sp-fLh_c3FVXX96fLjxbvrqgcFuQLQqLXoFWrWtlz3Yug7oYeBoYKm7QZEyRsA1cDAR6YbJlUnWimZhk6PI5ySs4PvEsPXFVM2s0s97vfWY1iTAS6Bayll-19UKMEA2lIK-uYv9Das0ZePPFCS1ZzxQokDVU6WUsTRLNHNNm6GM3MfnTlEZ0p05iE6s5Wl14_Wazfj8HvlV1YFgAOQyshPGP-8_Q_bn139pdI</recordid><startdate>20230601</startdate><enddate>20230601</enddate><creator>Shinoda, Seiya</creator><creator>Tozawa, Yuta</creator><creator>Kurimoto, Shin-ichiro</creator><creator>Shigemori, Hideyuki</creator><creator>Sekiguchi, Mitsuhiro</creator><general>Springer Nature Singapore</general><general>Springer Nature B.V</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>K9.</scope><scope>7X8</scope><scope>7S9</scope><scope>L.6</scope><orcidid>https://orcid.org/0000-0001-6780-4538</orcidid><orcidid>https://orcid.org/0000-0001-9778-8057</orcidid><orcidid>https://orcid.org/0000-0002-7906-2866</orcidid></search><sort><creationdate>20230601</creationdate><title>Three new meroterpenoids from Sargassum macrocarpum and their inhibitory activity against amyloid β aggregation</title><author>Shinoda, Seiya ; Tozawa, Yuta ; Kurimoto, Shin-ichiro ; Shigemori, Hideyuki ; Sekiguchi, Mitsuhiro</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c383t-339e992c8e907719c2dcb29dd0e8367bdee51633863d1f096058b2755093b9ff3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Algae</topic><topic>Alzheimer Disease - drug therapy</topic><topic>Alzheimer's disease</topic><topic>Amyloid</topic><topic>Amyloid beta-Peptides - antagonists & inhibitors</topic><topic>Biomedical and Life Sciences</topic><topic>Biomedicine</topic><topic>brain</topic><topic>Complementary & Alternative Medicine</topic><topic>Humans</topic><topic>Hydroquinone</topic><topic>Medicinal Chemistry</topic><topic>meroterpenoids</topic><topic>Metabolites</topic><topic>Neurodegenerative diseases</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>nuclear magnetic resonance spectroscopy</topic><topic>Original Paper</topic><topic>Pathogenesis</topic><topic>Pharmacology/Toxicology</topic><topic>Pharmacy</topic><topic>Plant Sciences</topic><topic>quinones</topic><topic>Sargassum</topic><topic>Sargassum - chemistry</topic><topic>Sargassum macrocarpum</topic><topic>Terpenes - chemistry</topic><topic>Terpenes - pharmacology</topic><topic>Transmission electron microscopy</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shinoda, Seiya</creatorcontrib><creatorcontrib>Tozawa, Yuta</creatorcontrib><creatorcontrib>Kurimoto, Shin-ichiro</creatorcontrib><creatorcontrib>Shigemori, Hideyuki</creatorcontrib><creatorcontrib>Sekiguchi, Mitsuhiro</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><jtitle>Journal of natural medicines</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shinoda, Seiya</au><au>Tozawa, Yuta</au><au>Kurimoto, Shin-ichiro</au><au>Shigemori, Hideyuki</au><au>Sekiguchi, Mitsuhiro</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Three new meroterpenoids from Sargassum macrocarpum and their inhibitory activity against amyloid β aggregation</atitle><jtitle>Journal of natural medicines</jtitle><stitle>J Nat Med</stitle><addtitle>J Nat Med</addtitle><date>2023-06-01</date><risdate>2023</risdate><volume>77</volume><issue>3</issue><spage>508</spage><epage>515</epage><pages>508-515</pages><issn>1340-3443</issn><eissn>1861-0293</eissn><abstract>Amyloid β (Aβ) is thought to be involved in the pathogenesis of Alzheimer’s disease (AD). Aβ aggregation in the brain is considered the cause of AD. Therefore, inhibiting Aβ aggregation and degrading existing Aβ aggregates is a promising approach for the treatment and prevention of the disease. In searching for inhibitors of Aβ42 aggregation, we found that meroterpenoids isolated from
Sargassum macrocarpum
possess potent inhibitory activities. Therefore, we searched for active compounds from this brown alga and isolated 16 meroterpenoids, which contain three new compounds. The structures of these new compounds were elucidated using two-dimensional nuclear magnetic resonance techniques. Thioflavin-T assay and transmission electron microscopy were used to reveal the inhibitory activity of these compounds against Aβ42 aggregation. All the isolated meroterpenoids were found to be active, and compounds with a hydroquinone structure tended to have stronger activity than those with a quinone structure.
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subjects | Algae Alzheimer Disease - drug therapy Alzheimer's disease Amyloid Amyloid beta-Peptides - antagonists & inhibitors Biomedical and Life Sciences Biomedicine brain Complementary & Alternative Medicine Humans Hydroquinone Medicinal Chemistry meroterpenoids Metabolites Neurodegenerative diseases NMR Nuclear magnetic resonance nuclear magnetic resonance spectroscopy Original Paper Pathogenesis Pharmacology/Toxicology Pharmacy Plant Sciences quinones Sargassum Sargassum - chemistry Sargassum macrocarpum Terpenes - chemistry Terpenes - pharmacology Transmission electron microscopy |
title | Three new meroterpenoids from Sargassum macrocarpum and their inhibitory activity against amyloid β aggregation |
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