Effect of Double Bond Position on 2-Phenyl-benzofuran Antioxidants: A Comparative Study of Moracin C and Iso-Moracin C

Two 2-phenyl-benzofurans, moracin C {2-[3′,5′-dihydroxy-4′-(3-methlbut-2-enyl)phenyl]-6-hydroxybenzofuran} and its isomer iso-moracin C{2-[3′,5′-dihydroxy-4′-(3-methlbut-1-enyl)phenyl]-6-hydroxybenzofuran}, were comparatively studied using redox-related antioxidant assays and non-redox antioxidant a...
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Autor*in:	Xican Li [verfasserIn] Hong Xie [verfasserIn] Ruicai Zhan [verfasserIn] Dongfeng Chen [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2018

Schlagwörter:	2-phenyl-benzofuran antioxidant moracin double bond positional isomeric effect

Übergeordnetes Werk:	In: Molecules - MDPI AG, 2003, 23(2018), 4, p 754
Übergeordnetes Werk:	volume:23 ; year:2018 ; number:4, p 754

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DOI / URN:	10.3390/molecules23040754

Katalog-ID:	DOAJ001707779

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520			\|a Two 2-phenyl-benzofurans, moracin C {2-[3′,5′-dihydroxy-4′-(3-methlbut-2-enyl)phenyl]-6-hydroxybenzofuran} and its isomer iso-moracin C{2-[3′,5′-dihydroxy-4′-(3-methlbut-1-enyl)phenyl]-6-hydroxybenzofuran}, were comparatively studied using redox-related antioxidant assays and non-redox antioxidant assays. Moracin C always resulted in higher IC50 values than iso-moracin C in the redox-related antioxidant assays, including •O2−-inhibition, Cu2+-reducing power, DPPH•-inhibition, and ABTS+•-inhibition assays. In the non-redox antioxidant assay, moracin C and iso-moracin C underwent similar radical-adduct-formation (RAF), evidenced by the peaks at m/z 704 and m/z 618 in HPLC-MS spectra. In conclusion, both moracin C and iso-moracin C can act as 2-phenyl-benzofuran antioxidants; their antioxidant mechanisms may include redox-related ET and H+-transfer, and non-redox RAF. A double bond at the conjugation position can enhance the redox-related antioxidant potential, but hardly affects the RAF potential.
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spelling	10.3390/molecules23040754 doi (DE-627)DOAJ001707779 (DE-599)DOAJ1d9dcb8c7a3841aca29b09ec5c199987 DE-627 ger DE-627 rakwb eng QD241-441 Xican Li verfasserin aut Effect of Double Bond Position on 2-Phenyl-benzofuran Antioxidants: A Comparative Study of Moracin C and Iso-Moracin C 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Two 2-phenyl-benzofurans, moracin C {2-[3′,5′-dihydroxy-4′-(3-methlbut-2-enyl)phenyl]-6-hydroxybenzofuran} and its isomer iso-moracin C{2-[3′,5′-dihydroxy-4′-(3-methlbut-1-enyl)phenyl]-6-hydroxybenzofuran}, were comparatively studied using redox-related antioxidant assays and non-redox antioxidant assays. Moracin C always resulted in higher IC50 values than iso-moracin C in the redox-related antioxidant assays, including •O2−-inhibition, Cu2+-reducing power, DPPH•-inhibition, and ABTS+•-inhibition assays. In the non-redox antioxidant assay, moracin C and iso-moracin C underwent similar radical-adduct-formation (RAF), evidenced by the peaks at m/z 704 and m/z 618 in HPLC-MS spectra. In conclusion, both moracin C and iso-moracin C can act as 2-phenyl-benzofuran antioxidants; their antioxidant mechanisms may include redox-related ET and H+-transfer, and non-redox RAF. A double bond at the conjugation position can enhance the redox-related antioxidant potential, but hardly affects the RAF potential. 2-phenyl-benzofuran antioxidant moracin double bond positional isomeric effect Organic chemistry Hong Xie verfasserin aut Ruicai Zhan verfasserin aut Dongfeng Chen verfasserin aut In Molecules MDPI AG, 2003 23(2018), 4, p 754 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:23 year:2018 number:4, p 754 https://doi.org/10.3390/molecules23040754 kostenfrei https://doaj.org/article/1d9dcb8c7a3841aca29b09ec5c199987 kostenfrei http://www.mdpi.com/1420-3049/23/4/754 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 23 2018 4, p 754
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allfieldsSound	10.3390/molecules23040754 doi (DE-627)DOAJ001707779 (DE-599)DOAJ1d9dcb8c7a3841aca29b09ec5c199987 DE-627 ger DE-627 rakwb eng QD241-441 Xican Li verfasserin aut Effect of Double Bond Position on 2-Phenyl-benzofuran Antioxidants: A Comparative Study of Moracin C and Iso-Moracin C 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Two 2-phenyl-benzofurans, moracin C {2-[3′,5′-dihydroxy-4′-(3-methlbut-2-enyl)phenyl]-6-hydroxybenzofuran} and its isomer iso-moracin C{2-[3′,5′-dihydroxy-4′-(3-methlbut-1-enyl)phenyl]-6-hydroxybenzofuran}, were comparatively studied using redox-related antioxidant assays and non-redox antioxidant assays. Moracin C always resulted in higher IC50 values than iso-moracin C in the redox-related antioxidant assays, including •O2−-inhibition, Cu2+-reducing power, DPPH•-inhibition, and ABTS+•-inhibition assays. In the non-redox antioxidant assay, moracin C and iso-moracin C underwent similar radical-adduct-formation (RAF), evidenced by the peaks at m/z 704 and m/z 618 in HPLC-MS spectra. In conclusion, both moracin C and iso-moracin C can act as 2-phenyl-benzofuran antioxidants; their antioxidant mechanisms may include redox-related ET and H+-transfer, and non-redox RAF. A double bond at the conjugation position can enhance the redox-related antioxidant potential, but hardly affects the RAF potential. 2-phenyl-benzofuran antioxidant moracin double bond positional isomeric effect Organic chemistry Hong Xie verfasserin aut Ruicai Zhan verfasserin aut Dongfeng Chen verfasserin aut In Molecules MDPI AG, 2003 23(2018), 4, p 754 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:23 year:2018 number:4, p 754 https://doi.org/10.3390/molecules23040754 kostenfrei https://doaj.org/article/1d9dcb8c7a3841aca29b09ec5c199987 kostenfrei http://www.mdpi.com/1420-3049/23/4/754 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 23 2018 4, p 754
language	English
source	In Molecules 23(2018), 4, p 754 volume:23 year:2018 number:4, p 754
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topic_facet	2-phenyl-benzofuran antioxidant moracin double bond positional isomeric effect Organic chemistry
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authorswithroles_txt_mv	Xican Li @@aut@@ Hong Xie @@aut@@ Ruicai Zhan @@aut@@ Dongfeng Chen @@aut@@
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callnumber-first	Q - Science
author	Xican Li
spellingShingle	Xican Li misc QD241-441 misc 2-phenyl-benzofuran misc antioxidant misc moracin misc double bond misc positional isomeric effect misc Organic chemistry Effect of Double Bond Position on 2-Phenyl-benzofuran Antioxidants: A Comparative Study of Moracin C and Iso-Moracin C
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topic_title	QD241-441 Effect of Double Bond Position on 2-Phenyl-benzofuran Antioxidants: A Comparative Study of Moracin C and Iso-Moracin C 2-phenyl-benzofuran antioxidant moracin double bond positional isomeric effect
topic	misc QD241-441 misc 2-phenyl-benzofuran misc antioxidant misc moracin misc double bond misc positional isomeric effect misc Organic chemistry
topic_unstemmed	misc QD241-441 misc 2-phenyl-benzofuran misc antioxidant misc moracin misc double bond misc positional isomeric effect misc Organic chemistry
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title	Effect of Double Bond Position on 2-Phenyl-benzofuran Antioxidants: A Comparative Study of Moracin C and Iso-Moracin C
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title_full	Effect of Double Bond Position on 2-Phenyl-benzofuran Antioxidants: A Comparative Study of Moracin C and Iso-Moracin C
author_sort	Xican Li
journal	Molecules
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author_browse	Xican Li Hong Xie Ruicai Zhan Dongfeng Chen
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title_sort	effect of double bond position on 2-phenyl-benzofuran antioxidants: a comparative study of moracin c and iso-moracin c
callnumber	QD241-441
title_auth	Effect of Double Bond Position on 2-Phenyl-benzofuran Antioxidants: A Comparative Study of Moracin C and Iso-Moracin C
abstract	Two 2-phenyl-benzofurans, moracin C {2-[3′,5′-dihydroxy-4′-(3-methlbut-2-enyl)phenyl]-6-hydroxybenzofuran} and its isomer iso-moracin C{2-[3′,5′-dihydroxy-4′-(3-methlbut-1-enyl)phenyl]-6-hydroxybenzofuran}, were comparatively studied using redox-related antioxidant assays and non-redox antioxidant assays. Moracin C always resulted in higher IC50 values than iso-moracin C in the redox-related antioxidant assays, including •O2−-inhibition, Cu2+-reducing power, DPPH•-inhibition, and ABTS+•-inhibition assays. In the non-redox antioxidant assay, moracin C and iso-moracin C underwent similar radical-adduct-formation (RAF), evidenced by the peaks at m/z 704 and m/z 618 in HPLC-MS spectra. In conclusion, both moracin C and iso-moracin C can act as 2-phenyl-benzofuran antioxidants; their antioxidant mechanisms may include redox-related ET and H+-transfer, and non-redox RAF. A double bond at the conjugation position can enhance the redox-related antioxidant potential, but hardly affects the RAF potential.
abstractGer	Two 2-phenyl-benzofurans, moracin C {2-[3′,5′-dihydroxy-4′-(3-methlbut-2-enyl)phenyl]-6-hydroxybenzofuran} and its isomer iso-moracin C{2-[3′,5′-dihydroxy-4′-(3-methlbut-1-enyl)phenyl]-6-hydroxybenzofuran}, were comparatively studied using redox-related antioxidant assays and non-redox antioxidant assays. Moracin C always resulted in higher IC50 values than iso-moracin C in the redox-related antioxidant assays, including •O2−-inhibition, Cu2+-reducing power, DPPH•-inhibition, and ABTS+•-inhibition assays. In the non-redox antioxidant assay, moracin C and iso-moracin C underwent similar radical-adduct-formation (RAF), evidenced by the peaks at m/z 704 and m/z 618 in HPLC-MS spectra. In conclusion, both moracin C and iso-moracin C can act as 2-phenyl-benzofuran antioxidants; their antioxidant mechanisms may include redox-related ET and H+-transfer, and non-redox RAF. A double bond at the conjugation position can enhance the redox-related antioxidant potential, but hardly affects the RAF potential.
abstract_unstemmed	Two 2-phenyl-benzofurans, moracin C {2-[3′,5′-dihydroxy-4′-(3-methlbut-2-enyl)phenyl]-6-hydroxybenzofuran} and its isomer iso-moracin C{2-[3′,5′-dihydroxy-4′-(3-methlbut-1-enyl)phenyl]-6-hydroxybenzofuran}, were comparatively studied using redox-related antioxidant assays and non-redox antioxidant assays. Moracin C always resulted in higher IC50 values than iso-moracin C in the redox-related antioxidant assays, including •O2−-inhibition, Cu2+-reducing power, DPPH•-inhibition, and ABTS+•-inhibition assays. In the non-redox antioxidant assay, moracin C and iso-moracin C underwent similar radical-adduct-formation (RAF), evidenced by the peaks at m/z 704 and m/z 618 in HPLC-MS spectra. In conclusion, both moracin C and iso-moracin C can act as 2-phenyl-benzofuran antioxidants; their antioxidant mechanisms may include redox-related ET and H+-transfer, and non-redox RAF. A double bond at the conjugation position can enhance the redox-related antioxidant potential, but hardly affects the RAF potential.
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title_short	Effect of Double Bond Position on 2-Phenyl-benzofuran Antioxidants: A Comparative Study of Moracin C and Iso-Moracin C
url	https://doi.org/10.3390/molecules23040754 https://doaj.org/article/1d9dcb8c7a3841aca29b09ec5c199987 http://www.mdpi.com/1420-3049/23/4/754 https://doaj.org/toc/1420-3049
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up_date	2024-07-03T21:58:21.397Z
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Effect of Double Bond Position on 2-Phenyl-benzofuran Antioxidants: A Comparative Study of Moracin C and Iso-Moracin C

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