The antioxidative potential of benzofuran-stilbene hybrid derivatives: a comparison between natural and synthetic compounds
The antioxidative activity of natural product compound amurensin H ( 1 ) and its three synthetic compounds 5-(6-hydroxy-2-(4-hydroxyphenyl)benzofuran-3-yl)benzene-1,3-diol ( 2 ), ( E )-2-(4-hydroxyphenyl)-4-(4-hydroxystyryl)benzofuran-6-ol ( 3 ), and ( E )-5-(6-hydroxy-4-(4-hydroxystyryl)benzofuran-...
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| Veröffentlicht in: | Structural chemistry 2021-12, Vol.32 (6), p.2271-2281 |
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| creator | Thuy, Phan Thi Van Trang, Nguyen Duc, Dau Xuan Son, Ninh The |
| description | The antioxidative activity of natural product compound amurensin H (
1
) and its three synthetic compounds 5-(6-hydroxy-2-(4-hydroxyphenyl)benzofuran-3-yl)benzene-1,3-diol (
2
), (
E
)-2-(4-hydroxyphenyl)-4-(4-hydroxystyryl)benzofuran-6-ol (
3
), and (
E
)-5-(6-hydroxy-4-(4-hydroxystyryl)benzofuran-3-yl)benzene-1,3-diol (
4
) are extensively studied by DFT (density functional theory) method. At the theoretical B3LYP/6-311G(d,p) level, the HAT (hydrogen atom transfer) mechanism is assignable to compounds
1-4
in gas, but the SPL-ET (sequential proton loss-electron transfer) mechanism is the main way in water and methanol. The antioxidative actions of the studied compounds are mainly based on OH bond breakage, especially OH groups directly substituted at benzofuran nucleus. Amurensin H (
1
) is better than the remaining compounds due to 6-OH group.
1
-6-OH induces the low bond BDE (bond dissociation enthalpy) and PA (proton affinity) values in thermal analysis. Importantly, the kinetic reaction of
1
-6-OH + HOO
•
in methanol exerts the lowest ΔG
#
value of 5.6 kcal/mol and the highest
K
value of 1.983 x 10
10
L/mol.s. At the B3LYP/6-311G(d,p)/LANL2DZ level, the successful formation of complex [Zn(compound
1
)
2
(H
2
O)
2
] at 6-OH is confirmed by molecular orbital and UV-Vis spectroscopic analyses. |
| doi_str_mv | 10.1007/s11224-021-01802-1 |
| format | Article |
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1
) and its three synthetic compounds 5-(6-hydroxy-2-(4-hydroxyphenyl)benzofuran-3-yl)benzene-1,3-diol (
2
), (
E
)-2-(4-hydroxyphenyl)-4-(4-hydroxystyryl)benzofuran-6-ol (
3
), and (
E
)-5-(6-hydroxy-4-(4-hydroxystyryl)benzofuran-3-yl)benzene-1,3-diol (
4
) are extensively studied by DFT (density functional theory) method. At the theoretical B3LYP/6-311G(d,p) level, the HAT (hydrogen atom transfer) mechanism is assignable to compounds
1-4
in gas, but the SPL-ET (sequential proton loss-electron transfer) mechanism is the main way in water and methanol. The antioxidative actions of the studied compounds are mainly based on OH bond breakage, especially OH groups directly substituted at benzofuran nucleus. Amurensin H (
1
) is better than the remaining compounds due to 6-OH group.
1
-6-OH induces the low bond BDE (bond dissociation enthalpy) and PA (proton affinity) values in thermal analysis. Importantly, the kinetic reaction of
1
-6-OH + HOO
•
in methanol exerts the lowest ΔG
#
value of 5.6 kcal/mol and the highest
K
value of 1.983 x 10
10
L/mol.s. At the B3LYP/6-311G(d,p)/LANL2DZ level, the successful formation of complex [Zn(compound
1
)
2
(H
2
O)
2
] at 6-OH is confirmed by molecular orbital and UV-Vis spectroscopic analyses.</description><identifier>ISSN: 1040-0400</identifier><identifier>EISSN: 1572-9001</identifier><identifier>DOI: 10.1007/s11224-021-01802-1</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Benzene ; Chemistry ; Chemistry and Materials Science ; Computer Applications in Chemistry ; Density functional theory ; Electron transfer ; Enthalpy ; Hydrocarbons ; Methanol ; Molecular orbitals ; Natural products ; Original Research ; Physical Chemistry ; Protons ; Stilbene ; Theoretical and Computational Chemistry ; Thermal analysis</subject><ispartof>Structural chemistry, 2021-12, Vol.32 (6), p.2271-2281</ispartof><rights>The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2021</rights><rights>The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2021.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c319t-3608dfa6db81fe38f34626b773c0a7aa6fb46b22c4b5864ae28318a1d5273bf23</citedby><cites>FETCH-LOGICAL-c319t-3608dfa6db81fe38f34626b773c0a7aa6fb46b22c4b5864ae28318a1d5273bf23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11224-021-01802-1$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11224-021-01802-1$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,778,782,27907,27908,41471,42540,51302</link.rule.ids></links><search><creatorcontrib>Thuy, Phan Thi</creatorcontrib><creatorcontrib>Van Trang, Nguyen</creatorcontrib><creatorcontrib>Duc, Dau Xuan</creatorcontrib><creatorcontrib>Son, Ninh The</creatorcontrib><title>The antioxidative potential of benzofuran-stilbene hybrid derivatives: a comparison between natural and synthetic compounds</title><title>Structural chemistry</title><addtitle>Struct Chem</addtitle><description>The antioxidative activity of natural product compound amurensin H (
1
) and its three synthetic compounds 5-(6-hydroxy-2-(4-hydroxyphenyl)benzofuran-3-yl)benzene-1,3-diol (
2
), (
E
)-2-(4-hydroxyphenyl)-4-(4-hydroxystyryl)benzofuran-6-ol (
3
), and (
E
)-5-(6-hydroxy-4-(4-hydroxystyryl)benzofuran-3-yl)benzene-1,3-diol (
4
) are extensively studied by DFT (density functional theory) method. At the theoretical B3LYP/6-311G(d,p) level, the HAT (hydrogen atom transfer) mechanism is assignable to compounds
1-4
in gas, but the SPL-ET (sequential proton loss-electron transfer) mechanism is the main way in water and methanol. The antioxidative actions of the studied compounds are mainly based on OH bond breakage, especially OH groups directly substituted at benzofuran nucleus. Amurensin H (
1
) is better than the remaining compounds due to 6-OH group.
1
-6-OH induces the low bond BDE (bond dissociation enthalpy) and PA (proton affinity) values in thermal analysis. Importantly, the kinetic reaction of
1
-6-OH + HOO
•
in methanol exerts the lowest ΔG
#
value of 5.6 kcal/mol and the highest
K
value of 1.983 x 10
10
L/mol.s. At the B3LYP/6-311G(d,p)/LANL2DZ level, the successful formation of complex [Zn(compound
1
)
2
(H
2
O)
2
] at 6-OH is confirmed by molecular orbital and UV-Vis spectroscopic analyses.</description><subject>Benzene</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Computer Applications in Chemistry</subject><subject>Density functional theory</subject><subject>Electron transfer</subject><subject>Enthalpy</subject><subject>Hydrocarbons</subject><subject>Methanol</subject><subject>Molecular orbitals</subject><subject>Natural products</subject><subject>Original Research</subject><subject>Physical Chemistry</subject><subject>Protons</subject><subject>Stilbene</subject><subject>Theoretical and Computational Chemistry</subject><subject>Thermal analysis</subject><issn>1040-0400</issn><issn>1572-9001</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNp9kEtLAzEUhYMoWB9_wFXAdTSPmczUnRRfUHBT1yGZJDZlmtQkU63-eWNHcOfich-c71w4AFwQfEUwbq4TIZRWCFOCMGkxReQATEjdUDTFmByWGVcYlcLH4CSlVTkSzuoJ-FosDZQ-u_DhtMxua-AmZFMOsofBQmX8Z7BDlB6l7PqyGrjcqeg01Ca67R5JN1DCLqw3MroUfIHyuzEeepkL2Rd_DdPO56XJrtsLw-B1OgNHVvbJnP_2U_Byf7eYPaL588PT7HaOOkamGTGOW20l16ol1rDWsopTrpqGdVg2UnKrKq4o7SpVt7yShraMtJLomjZMWcpOweXou4nhbTApi1UYoi8vBa3belrxGldFRUdVF0NK0VixiW4t404QLH5CFmPIooQs9iELUiA2QqmI_auJf9b_UN-phoId</recordid><startdate>20211201</startdate><enddate>20211201</enddate><creator>Thuy, Phan Thi</creator><creator>Van Trang, Nguyen</creator><creator>Duc, Dau Xuan</creator><creator>Son, Ninh The</creator><general>Springer US</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20211201</creationdate><title>The antioxidative potential of benzofuran-stilbene hybrid derivatives: a comparison between natural and synthetic compounds</title><author>Thuy, Phan Thi ; Van Trang, Nguyen ; Duc, Dau Xuan ; Son, Ninh The</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c319t-3608dfa6db81fe38f34626b773c0a7aa6fb46b22c4b5864ae28318a1d5273bf23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Benzene</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Computer Applications in Chemistry</topic><topic>Density functional theory</topic><topic>Electron transfer</topic><topic>Enthalpy</topic><topic>Hydrocarbons</topic><topic>Methanol</topic><topic>Molecular orbitals</topic><topic>Natural products</topic><topic>Original Research</topic><topic>Physical Chemistry</topic><topic>Protons</topic><topic>Stilbene</topic><topic>Theoretical and Computational Chemistry</topic><topic>Thermal analysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Thuy, Phan Thi</creatorcontrib><creatorcontrib>Van Trang, Nguyen</creatorcontrib><creatorcontrib>Duc, Dau Xuan</creatorcontrib><creatorcontrib>Son, Ninh The</creatorcontrib><collection>CrossRef</collection><jtitle>Structural chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Thuy, Phan Thi</au><au>Van Trang, Nguyen</au><au>Duc, Dau Xuan</au><au>Son, Ninh The</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The antioxidative potential of benzofuran-stilbene hybrid derivatives: a comparison between natural and synthetic compounds</atitle><jtitle>Structural chemistry</jtitle><stitle>Struct Chem</stitle><date>2021-12-01</date><risdate>2021</risdate><volume>32</volume><issue>6</issue><spage>2271</spage><epage>2281</epage><pages>2271-2281</pages><issn>1040-0400</issn><eissn>1572-9001</eissn><abstract>The antioxidative activity of natural product compound amurensin H (
1
) and its three synthetic compounds 5-(6-hydroxy-2-(4-hydroxyphenyl)benzofuran-3-yl)benzene-1,3-diol (
2
), (
E
)-2-(4-hydroxyphenyl)-4-(4-hydroxystyryl)benzofuran-6-ol (
3
), and (
E
)-5-(6-hydroxy-4-(4-hydroxystyryl)benzofuran-3-yl)benzene-1,3-diol (
4
) are extensively studied by DFT (density functional theory) method. At the theoretical B3LYP/6-311G(d,p) level, the HAT (hydrogen atom transfer) mechanism is assignable to compounds
1-4
in gas, but the SPL-ET (sequential proton loss-electron transfer) mechanism is the main way in water and methanol. The antioxidative actions of the studied compounds are mainly based on OH bond breakage, especially OH groups directly substituted at benzofuran nucleus. Amurensin H (
1
) is better than the remaining compounds due to 6-OH group.
1
-6-OH induces the low bond BDE (bond dissociation enthalpy) and PA (proton affinity) values in thermal analysis. Importantly, the kinetic reaction of
1
-6-OH + HOO
•
in methanol exerts the lowest ΔG
#
value of 5.6 kcal/mol and the highest
K
value of 1.983 x 10
10
L/mol.s. At the B3LYP/6-311G(d,p)/LANL2DZ level, the successful formation of complex [Zn(compound
1
)
2
(H
2
O)
2
] at 6-OH is confirmed by molecular orbital and UV-Vis spectroscopic analyses.</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s11224-021-01802-1</doi><tpages>11</tpages></addata></record> |
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| subjects | Benzene Chemistry Chemistry and Materials Science Computer Applications in Chemistry Density functional theory Electron transfer Enthalpy Hydrocarbons Methanol Molecular orbitals Natural products Original Research Physical Chemistry Protons Stilbene Theoretical and Computational Chemistry Thermal analysis |
| title | The antioxidative potential of benzofuran-stilbene hybrid derivatives: a comparison between natural and synthetic compounds |
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