Anti-Alzheimer's flavanolignans from Ceiba pentandra aerial parts
Four flavanolignans, ceibapentains A (1) and B (2) and cinchonains Ia (3) and Ib (4), were isolated for the first time from an ethyl acetate extract of Ceiba pentandra (L) (Bombacaceae) aerial parts. The ceibapentains A (1) and B (2) are new compounds and their structures, including the absolute con...
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| Veröffentlicht in: | Fitoterapia 2020-06, Vol.143, p.104541-7, Article 104541 |
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| creator | Abouelela, Mohamed E. Orabi, Mohamed A.A. Abdelhamid, Reda A. Abdelkader, Mohamed S.A. Darwish, Faten M.M. Hotsumi, Mayumi Konno, Hiroyuki |
| description | Four flavanolignans, ceibapentains A (1) and B (2) and cinchonains Ia (3) and Ib (4), were isolated for the first time from an ethyl acetate extract of Ceiba pentandra (L) (Bombacaceae) aerial parts. The ceibapentains A (1) and B (2) are new compounds and their structures, including the absolute configurations, were determined by HRESIMS, 1D and 2D NMR, and electronic circular dichroism analyses, then compared with reported data. Compounds 1–4 were tested for their anti-Alzheimer's activity via an assessment of their inhibitory effect on amyloid β42 aggregation using a thioflavin T assay. The results revealed that cinchonain Ia (3) showed a higher inhibitory effect (91%) than the standard curcumin (70%). Compounds 1, 2, and 4 exhibited moderate activity, with inhibition ratios of 43%, 47%, and 58%, respectively. A molecular docking study on the binding mode of 3 and curcumin with an amyloid β1–40 peptide fibril structure indicated a high affinity of cinchonain 1a (3) towards amyloid β1–40 peptide, in agreement with the experimental results.
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•Isolation of two new and two known flavanolignans from Ceiba pentandra•Investigation of the anti-Alzheimer's activities of the isolated compounds•Assessment of their inhibitory effect on amyloid β42 aggregation•Molecular docking study on the binding mode of compounds with amyloid β1–40 |
| doi_str_mv | 10.1016/j.fitote.2020.104541 |
| format | Article |
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[Display omitted]
•Isolation of two new and two known flavanolignans from Ceiba pentandra•Investigation of the anti-Alzheimer's activities of the isolated compounds•Assessment of their inhibitory effect on amyloid β42 aggregation•Molecular docking study on the binding mode of compounds with amyloid β1–40</description><identifier>ISSN: 0367-326X</identifier><identifier>EISSN: 1873-6971</identifier><identifier>DOI: 10.1016/j.fitote.2020.104541</identifier><identifier>PMID: 32151639</identifier><language>eng</language><publisher>Netherlands: Elsevier B.V</publisher><subject>Acetic acid ; Alzheimer's disease ; Amyloid beta-Peptides - antagonists & inhibitors ; Amyloid β42 ; Anti-Alzheimer's ; Bombacaceae ; Ceiba - chemistry ; Ceiba pentandra ; Ceibapentains ; Circular Dichroism ; Curcumin ; Dichroism ; Egypt ; Ethyl acetate ; Flavanolignan ; Flavonolignans - isolation & purification ; Flavonolignans - pharmacology ; Humans ; Molecular docking ; Molecular Docking Simulation ; Molecular Structure ; Neurodegenerative diseases ; NMR ; Nuclear magnetic resonance ; Peptide Fragments - antagonists & inhibitors ; Peptides ; Phytochemicals - isolation & purification ; Phytochemicals - pharmacology ; Plant Components, Aerial - chemistry ; Plant Extracts - chemistry ; Two dimensional analysis ; β-Amyloid</subject><ispartof>Fitoterapia, 2020-06, Vol.143, p.104541-7, Article 104541</ispartof><rights>2020 Elsevier B.V.</rights><rights>Copyright © 2020 Elsevier B.V. All rights reserved.</rights><rights>Copyright Elsevier Science Ltd. Jun 2020</rights><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c390t-585f8390700f9aad4a7820331b5eff50f891c8e409bb3d82bac0aba357228f6b3</citedby><cites>FETCH-LOGICAL-c390t-585f8390700f9aad4a7820331b5eff50f891c8e409bb3d82bac0aba357228f6b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.fitote.2020.104541$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3548,27923,27924,45994</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32151639$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Abouelela, Mohamed E.</creatorcontrib><creatorcontrib>Orabi, Mohamed A.A.</creatorcontrib><creatorcontrib>Abdelhamid, Reda A.</creatorcontrib><creatorcontrib>Abdelkader, Mohamed S.A.</creatorcontrib><creatorcontrib>Darwish, Faten M.M.</creatorcontrib><creatorcontrib>Hotsumi, Mayumi</creatorcontrib><creatorcontrib>Konno, Hiroyuki</creatorcontrib><title>Anti-Alzheimer's flavanolignans from Ceiba pentandra aerial parts</title><title>Fitoterapia</title><addtitle>Fitoterapia</addtitle><description>Four flavanolignans, ceibapentains A (1) and B (2) and cinchonains Ia (3) and Ib (4), were isolated for the first time from an ethyl acetate extract of Ceiba pentandra (L) (Bombacaceae) aerial parts. The ceibapentains A (1) and B (2) are new compounds and their structures, including the absolute configurations, were determined by HRESIMS, 1D and 2D NMR, and electronic circular dichroism analyses, then compared with reported data. Compounds 1–4 were tested for their anti-Alzheimer's activity via an assessment of their inhibitory effect on amyloid β42 aggregation using a thioflavin T assay. The results revealed that cinchonain Ia (3) showed a higher inhibitory effect (91%) than the standard curcumin (70%). Compounds 1, 2, and 4 exhibited moderate activity, with inhibition ratios of 43%, 47%, and 58%, respectively. A molecular docking study on the binding mode of 3 and curcumin with an amyloid β1–40 peptide fibril structure indicated a high affinity of cinchonain 1a (3) towards amyloid β1–40 peptide, in agreement with the experimental results.
[Display omitted]
•Isolation of two new and two known flavanolignans from Ceiba pentandra•Investigation of the anti-Alzheimer's activities of the isolated compounds•Assessment of their inhibitory effect on amyloid β42 aggregation•Molecular docking study on the binding mode of compounds with amyloid β1–40</description><subject>Acetic acid</subject><subject>Alzheimer's disease</subject><subject>Amyloid beta-Peptides - antagonists & inhibitors</subject><subject>Amyloid β42</subject><subject>Anti-Alzheimer's</subject><subject>Bombacaceae</subject><subject>Ceiba - chemistry</subject><subject>Ceiba pentandra</subject><subject>Ceibapentains</subject><subject>Circular Dichroism</subject><subject>Curcumin</subject><subject>Dichroism</subject><subject>Egypt</subject><subject>Ethyl acetate</subject><subject>Flavanolignan</subject><subject>Flavonolignans - isolation & purification</subject><subject>Flavonolignans - pharmacology</subject><subject>Humans</subject><subject>Molecular docking</subject><subject>Molecular Docking Simulation</subject><subject>Molecular Structure</subject><subject>Neurodegenerative diseases</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Peptide Fragments - antagonists & inhibitors</subject><subject>Peptides</subject><subject>Phytochemicals - isolation & purification</subject><subject>Phytochemicals - pharmacology</subject><subject>Plant Components, Aerial - chemistry</subject><subject>Plant Extracts - chemistry</subject><subject>Two dimensional analysis</subject><subject>β-Amyloid</subject><issn>0367-326X</issn><issn>1873-6971</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kEtLxDAUhYMoOo7-A5GCC1cd8-gj3QjD4AsG3Ci4Czftjaa0aU06A_rr7dDRpav74Jx7uB8hF4wuGGXZTb0wdugGXHDKd6skTdgBmTGZizgrcnZIZlRkeSx49nZCTkOoKWWpSNgxORGcpSwTxYwsl26w8bL5_kDbor8OkWlgC65r7LsDN46-a6MVWg1Rj24AV3mIAL2FJurBD-GMHBloAp7v65y83t-9rB7j9fPD02q5jktR0CFOZWrk2OWUmgKgSiCXnArBdIrGpNTIgpUSE1poLSrJNZQUNIg051yaTIs5uZru9r773GAYVN1tvBsjFU-yXDKRF2xUJZOq9F0IHo3qvW3BfylG1Y6bqtXETe24qYnbaLvcH9_oFqs_0y-oUXA7CXB8cWvRq1BadCVW1mM5qKqz_yf8AGtmf2o</recordid><startdate>202006</startdate><enddate>202006</enddate><creator>Abouelela, Mohamed E.</creator><creator>Orabi, Mohamed A.A.</creator><creator>Abdelhamid, Reda A.</creator><creator>Abdelkader, Mohamed S.A.</creator><creator>Darwish, Faten M.M.</creator><creator>Hotsumi, Mayumi</creator><creator>Konno, Hiroyuki</creator><general>Elsevier B.V</general><general>Elsevier Science Ltd</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>7U7</scope><scope>7U9</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>H94</scope><scope>M7N</scope><scope>P64</scope></search><sort><creationdate>202006</creationdate><title>Anti-Alzheimer's flavanolignans from Ceiba pentandra aerial parts</title><author>Abouelela, Mohamed E. ; Orabi, Mohamed A.A. ; Abdelhamid, Reda A. ; Abdelkader, Mohamed S.A. ; Darwish, Faten M.M. ; Hotsumi, Mayumi ; Konno, Hiroyuki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c390t-585f8390700f9aad4a7820331b5eff50f891c8e409bb3d82bac0aba357228f6b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Acetic acid</topic><topic>Alzheimer's disease</topic><topic>Amyloid beta-Peptides - antagonists & inhibitors</topic><topic>Amyloid β42</topic><topic>Anti-Alzheimer's</topic><topic>Bombacaceae</topic><topic>Ceiba - chemistry</topic><topic>Ceiba pentandra</topic><topic>Ceibapentains</topic><topic>Circular Dichroism</topic><topic>Curcumin</topic><topic>Dichroism</topic><topic>Egypt</topic><topic>Ethyl acetate</topic><topic>Flavanolignan</topic><topic>Flavonolignans - isolation & purification</topic><topic>Flavonolignans - pharmacology</topic><topic>Humans</topic><topic>Molecular docking</topic><topic>Molecular Docking Simulation</topic><topic>Molecular Structure</topic><topic>Neurodegenerative diseases</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Peptide Fragments - antagonists & inhibitors</topic><topic>Peptides</topic><topic>Phytochemicals - isolation & purification</topic><topic>Phytochemicals - pharmacology</topic><topic>Plant Components, Aerial - chemistry</topic><topic>Plant Extracts - chemistry</topic><topic>Two dimensional analysis</topic><topic>β-Amyloid</topic><toplevel>online_resources</toplevel><creatorcontrib>Abouelela, Mohamed E.</creatorcontrib><creatorcontrib>Orabi, Mohamed A.A.</creatorcontrib><creatorcontrib>Abdelhamid, Reda A.</creatorcontrib><creatorcontrib>Abdelkader, Mohamed S.A.</creatorcontrib><creatorcontrib>Darwish, Faten M.M.</creatorcontrib><creatorcontrib>Hotsumi, Mayumi</creatorcontrib><creatorcontrib>Konno, Hiroyuki</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>Toxicology Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Fitoterapia</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Abouelela, Mohamed E.</au><au>Orabi, Mohamed A.A.</au><au>Abdelhamid, Reda A.</au><au>Abdelkader, Mohamed S.A.</au><au>Darwish, Faten M.M.</au><au>Hotsumi, Mayumi</au><au>Konno, Hiroyuki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Anti-Alzheimer's flavanolignans from Ceiba pentandra aerial parts</atitle><jtitle>Fitoterapia</jtitle><addtitle>Fitoterapia</addtitle><date>2020-06</date><risdate>2020</risdate><volume>143</volume><spage>104541</spage><epage>7</epage><pages>104541-7</pages><artnum>104541</artnum><issn>0367-326X</issn><eissn>1873-6971</eissn><abstract>Four flavanolignans, ceibapentains A (1) and B (2) and cinchonains Ia (3) and Ib (4), were isolated for the first time from an ethyl acetate extract of Ceiba pentandra (L) (Bombacaceae) aerial parts. The ceibapentains A (1) and B (2) are new compounds and their structures, including the absolute configurations, were determined by HRESIMS, 1D and 2D NMR, and electronic circular dichroism analyses, then compared with reported data. Compounds 1–4 were tested for their anti-Alzheimer's activity via an assessment of their inhibitory effect on amyloid β42 aggregation using a thioflavin T assay. The results revealed that cinchonain Ia (3) showed a higher inhibitory effect (91%) than the standard curcumin (70%). Compounds 1, 2, and 4 exhibited moderate activity, with inhibition ratios of 43%, 47%, and 58%, respectively. A molecular docking study on the binding mode of 3 and curcumin with an amyloid β1–40 peptide fibril structure indicated a high affinity of cinchonain 1a (3) towards amyloid β1–40 peptide, in agreement with the experimental results.
[Display omitted]
•Isolation of two new and two known flavanolignans from Ceiba pentandra•Investigation of the anti-Alzheimer's activities of the isolated compounds•Assessment of their inhibitory effect on amyloid β42 aggregation•Molecular docking study on the binding mode of compounds with amyloid β1–40</abstract><cop>Netherlands</cop><pub>Elsevier B.V</pub><pmid>32151639</pmid><doi>10.1016/j.fitote.2020.104541</doi><tpages>7</tpages></addata></record> |
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| subjects | Acetic acid Alzheimer's disease Amyloid beta-Peptides - antagonists & inhibitors Amyloid β42 Anti-Alzheimer's Bombacaceae Ceiba - chemistry Ceiba pentandra Ceibapentains Circular Dichroism Curcumin Dichroism Egypt Ethyl acetate Flavanolignan Flavonolignans - isolation & purification Flavonolignans - pharmacology Humans Molecular docking Molecular Docking Simulation Molecular Structure Neurodegenerative diseases NMR Nuclear magnetic resonance Peptide Fragments - antagonists & inhibitors Peptides Phytochemicals - isolation & purification Phytochemicals - pharmacology Plant Components, Aerial - chemistry Plant Extracts - chemistry Two dimensional analysis β-Amyloid |
| title | Anti-Alzheimer's flavanolignans from Ceiba pentandra aerial parts |
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