Chemoprotective Effects of Xanthohumol against the Carcinogenic Mycotoxin Aflatoxin B1

The present study addresses the chemoprotective effects of xanthohumol (XN), a prenylated flavonoid found in the female inflorescences (hops) of the plant <i<Humulus lupulus</i< L., against the carcinogenic food contaminant aflatoxin B1 (AFB1). The chemical reactions of XN and its deriva...
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Autor*in:	Alja Štern [verfasserIn] Veronika Furlan [verfasserIn] Matjaž Novak [verfasserIn] Martina Štampar [verfasserIn] Zala Kolenc [verfasserIn] Katarina Kores [verfasserIn] Metka Filipič [verfasserIn] Urban Bren [verfasserIn] Bojana Žegura [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2021

Schlagwörter:	xanthohumol isoxanthohumol 8-prenylnaringenin: 6-prenylnaringenin aflatoxin B1 aflatoxin B1 exo-8,9-epoxide genotoxicity

Übergeordnetes Werk:	In: Foods - MDPI AG, 2013, 10(2021), 6, p 1331
Übergeordnetes Werk:	volume:10 ; year:2021 ; number:6, p 1331

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.3390/foods10061331

Katalog-ID:	DOAJ00336996X

Internformat


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520			\|a The present study addresses the chemoprotective effects of xanthohumol (XN), a prenylated flavonoid found in the female inflorescences (hops) of the plant <i<Humulus lupulus</i< L., against the carcinogenic food contaminant aflatoxin B1 (AFB1). The chemical reactions of XN and its derivatives (isoxanthohumol (IXN), 8-prenylnaringenin (8-PN), and 6-prenylnaringenin (6-PN)) with the AFB1 metabolite, aflatoxin B1 exo-8,9-epoxide (AFBO), were investigated <i<in silico</i<, by calculating activation free energies (ΔG<sup<‡</sup<) at the Hartree–Fock level of theory in combination with the 6-311++G(d,p) basis set and two implicit solvation models. The chemoprotective effects of XN were investigated <i<in vitro</i< in the metabolically competent HepG2 cell line, analyzing its influence on AFB1-induced cytotoxicity using the MTS assay, genotoxicity using the comet and γH2AX assays, and cell cycle modulation using flow cytometry. Our results show that the ΔG<sup<‡</sup< required for the reactions of XN and its derivatives with AFBO are comparable to the ΔG<sup<‡</sup< required for the reaction of AFBO with guanine, indicating that XN, IXN, 8-PN, and 6-PN could act as scavengers of AFBO, preventing DNA adduct formation and DNA damage induction. This was also reflected in the results from the <i<in vitro</i< experiments, where a reduction in AFB1-induced cytotoxicity and DNA single-strand and double-strand breaks was observed in cells exposed to combinations of AFB1 and XN, highlighting the chemoprotective effects of this phytochemical.
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author_variant	a š aš v f vf m n mn m š mš z k zk k k kk m f mf u b ub b ž bž
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allfields	10.3390/foods10061331 doi (DE-627)DOAJ00336996X (DE-599)DOAJ81b7b413fa14461b885caa07c50fef7b DE-627 ger DE-627 rakwb eng TP1-1185 Alja Štern verfasserin aut Chemoprotective Effects of Xanthohumol against the Carcinogenic Mycotoxin Aflatoxin B1 2021 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The present study addresses the chemoprotective effects of xanthohumol (XN), a prenylated flavonoid found in the female inflorescences (hops) of the plant <i<Humulus lupulus</i< L., against the carcinogenic food contaminant aflatoxin B1 (AFB1). The chemical reactions of XN and its derivatives (isoxanthohumol (IXN), 8-prenylnaringenin (8-PN), and 6-prenylnaringenin (6-PN)) with the AFB1 metabolite, aflatoxin B1 exo-8,9-epoxide (AFBO), were investigated <i<in silico</i<, by calculating activation free energies (ΔG<sup<‡</sup<) at the Hartree–Fock level of theory in combination with the 6-311++G(d,p) basis set and two implicit solvation models. The chemoprotective effects of XN were investigated <i<in vitro</i< in the metabolically competent HepG2 cell line, analyzing its influence on AFB1-induced cytotoxicity using the MTS assay, genotoxicity using the comet and γH2AX assays, and cell cycle modulation using flow cytometry. Our results show that the ΔG<sup<‡</sup< required for the reactions of XN and its derivatives with AFBO are comparable to the ΔG<sup<‡</sup< required for the reaction of AFBO with guanine, indicating that XN, IXN, 8-PN, and 6-PN could act as scavengers of AFBO, preventing DNA adduct formation and DNA damage induction. This was also reflected in the results from the <i<in vitro</i< experiments, where a reduction in AFB1-induced cytotoxicity and DNA single-strand and double-strand breaks was observed in cells exposed to combinations of AFB1 and XN, highlighting the chemoprotective effects of this phytochemical. xanthohumol isoxanthohumol 8-prenylnaringenin: 6-prenylnaringenin aflatoxin B1 aflatoxin B1 exo-8,9-epoxide genotoxicity Chemical technology Veronika Furlan verfasserin aut Matjaž Novak verfasserin aut Martina Štampar verfasserin aut Zala Kolenc verfasserin aut Katarina Kores verfasserin aut Metka Filipič verfasserin aut Urban Bren verfasserin aut Bojana Žegura verfasserin aut In Foods MDPI AG, 2013 10(2021), 6, p 1331 (DE-627)737287632 (DE-600)2704223-6 23048158 nnns volume:10 year:2021 number:6, p 1331 https://doi.org/10.3390/foods10061331 kostenfrei https://doaj.org/article/81b7b413fa14461b885caa07c50fef7b kostenfrei https://www.mdpi.com/2304-8158/10/6/1331 kostenfrei https://doaj.org/toc/2304-8158 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_24 GBV_ILN_31 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_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 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 10 2021 6, p 1331
spelling	10.3390/foods10061331 doi (DE-627)DOAJ00336996X (DE-599)DOAJ81b7b413fa14461b885caa07c50fef7b DE-627 ger DE-627 rakwb eng TP1-1185 Alja Štern verfasserin aut Chemoprotective Effects of Xanthohumol against the Carcinogenic Mycotoxin Aflatoxin B1 2021 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The present study addresses the chemoprotective effects of xanthohumol (XN), a prenylated flavonoid found in the female inflorescences (hops) of the plant <i<Humulus lupulus</i< L., against the carcinogenic food contaminant aflatoxin B1 (AFB1). The chemical reactions of XN and its derivatives (isoxanthohumol (IXN), 8-prenylnaringenin (8-PN), and 6-prenylnaringenin (6-PN)) with the AFB1 metabolite, aflatoxin B1 exo-8,9-epoxide (AFBO), were investigated <i<in silico</i<, by calculating activation free energies (ΔG<sup<‡</sup<) at the Hartree–Fock level of theory in combination with the 6-311++G(d,p) basis set and two implicit solvation models. The chemoprotective effects of XN were investigated <i<in vitro</i< in the metabolically competent HepG2 cell line, analyzing its influence on AFB1-induced cytotoxicity using the MTS assay, genotoxicity using the comet and γH2AX assays, and cell cycle modulation using flow cytometry. Our results show that the ΔG<sup<‡</sup< required for the reactions of XN and its derivatives with AFBO are comparable to the ΔG<sup<‡</sup< required for the reaction of AFBO with guanine, indicating that XN, IXN, 8-PN, and 6-PN could act as scavengers of AFBO, preventing DNA adduct formation and DNA damage induction. This was also reflected in the results from the <i<in vitro</i< experiments, where a reduction in AFB1-induced cytotoxicity and DNA single-strand and double-strand breaks was observed in cells exposed to combinations of AFB1 and XN, highlighting the chemoprotective effects of this phytochemical. xanthohumol isoxanthohumol 8-prenylnaringenin: 6-prenylnaringenin aflatoxin B1 aflatoxin B1 exo-8,9-epoxide genotoxicity Chemical technology Veronika Furlan verfasserin aut Matjaž Novak verfasserin aut Martina Štampar verfasserin aut Zala Kolenc verfasserin aut Katarina Kores verfasserin aut Metka Filipič verfasserin aut Urban Bren verfasserin aut Bojana Žegura verfasserin aut In Foods MDPI AG, 2013 10(2021), 6, p 1331 (DE-627)737287632 (DE-600)2704223-6 23048158 nnns volume:10 year:2021 number:6, p 1331 https://doi.org/10.3390/foods10061331 kostenfrei https://doaj.org/article/81b7b413fa14461b885caa07c50fef7b kostenfrei https://www.mdpi.com/2304-8158/10/6/1331 kostenfrei https://doaj.org/toc/2304-8158 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_24 GBV_ILN_31 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_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 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 10 2021 6, p 1331
allfields_unstemmed	10.3390/foods10061331 doi (DE-627)DOAJ00336996X (DE-599)DOAJ81b7b413fa14461b885caa07c50fef7b DE-627 ger DE-627 rakwb eng TP1-1185 Alja Štern verfasserin aut Chemoprotective Effects of Xanthohumol against the Carcinogenic Mycotoxin Aflatoxin B1 2021 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The present study addresses the chemoprotective effects of xanthohumol (XN), a prenylated flavonoid found in the female inflorescences (hops) of the plant <i<Humulus lupulus</i< L., against the carcinogenic food contaminant aflatoxin B1 (AFB1). The chemical reactions of XN and its derivatives (isoxanthohumol (IXN), 8-prenylnaringenin (8-PN), and 6-prenylnaringenin (6-PN)) with the AFB1 metabolite, aflatoxin B1 exo-8,9-epoxide (AFBO), were investigated <i<in silico</i<, by calculating activation free energies (ΔG<sup<‡</sup<) at the Hartree–Fock level of theory in combination with the 6-311++G(d,p) basis set and two implicit solvation models. The chemoprotective effects of XN were investigated <i<in vitro</i< in the metabolically competent HepG2 cell line, analyzing its influence on AFB1-induced cytotoxicity using the MTS assay, genotoxicity using the comet and γH2AX assays, and cell cycle modulation using flow cytometry. Our results show that the ΔG<sup<‡</sup< required for the reactions of XN and its derivatives with AFBO are comparable to the ΔG<sup<‡</sup< required for the reaction of AFBO with guanine, indicating that XN, IXN, 8-PN, and 6-PN could act as scavengers of AFBO, preventing DNA adduct formation and DNA damage induction. This was also reflected in the results from the <i<in vitro</i< experiments, where a reduction in AFB1-induced cytotoxicity and DNA single-strand and double-strand breaks was observed in cells exposed to combinations of AFB1 and XN, highlighting the chemoprotective effects of this phytochemical. xanthohumol isoxanthohumol 8-prenylnaringenin: 6-prenylnaringenin aflatoxin B1 aflatoxin B1 exo-8,9-epoxide genotoxicity Chemical technology Veronika Furlan verfasserin aut Matjaž Novak verfasserin aut Martina Štampar verfasserin aut Zala Kolenc verfasserin aut Katarina Kores verfasserin aut Metka Filipič verfasserin aut Urban Bren verfasserin aut Bojana Žegura verfasserin aut In Foods MDPI AG, 2013 10(2021), 6, p 1331 (DE-627)737287632 (DE-600)2704223-6 23048158 nnns volume:10 year:2021 number:6, p 1331 https://doi.org/10.3390/foods10061331 kostenfrei https://doaj.org/article/81b7b413fa14461b885caa07c50fef7b kostenfrei https://www.mdpi.com/2304-8158/10/6/1331 kostenfrei https://doaj.org/toc/2304-8158 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_24 GBV_ILN_31 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_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 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 10 2021 6, p 1331
allfieldsGer	10.3390/foods10061331 doi (DE-627)DOAJ00336996X (DE-599)DOAJ81b7b413fa14461b885caa07c50fef7b DE-627 ger DE-627 rakwb eng TP1-1185 Alja Štern verfasserin aut Chemoprotective Effects of Xanthohumol against the Carcinogenic Mycotoxin Aflatoxin B1 2021 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The present study addresses the chemoprotective effects of xanthohumol (XN), a prenylated flavonoid found in the female inflorescences (hops) of the plant <i<Humulus lupulus</i< L., against the carcinogenic food contaminant aflatoxin B1 (AFB1). The chemical reactions of XN and its derivatives (isoxanthohumol (IXN), 8-prenylnaringenin (8-PN), and 6-prenylnaringenin (6-PN)) with the AFB1 metabolite, aflatoxin B1 exo-8,9-epoxide (AFBO), were investigated <i<in silico</i<, by calculating activation free energies (ΔG<sup<‡</sup<) at the Hartree–Fock level of theory in combination with the 6-311++G(d,p) basis set and two implicit solvation models. The chemoprotective effects of XN were investigated <i<in vitro</i< in the metabolically competent HepG2 cell line, analyzing its influence on AFB1-induced cytotoxicity using the MTS assay, genotoxicity using the comet and γH2AX assays, and cell cycle modulation using flow cytometry. Our results show that the ΔG<sup<‡</sup< required for the reactions of XN and its derivatives with AFBO are comparable to the ΔG<sup<‡</sup< required for the reaction of AFBO with guanine, indicating that XN, IXN, 8-PN, and 6-PN could act as scavengers of AFBO, preventing DNA adduct formation and DNA damage induction. This was also reflected in the results from the <i<in vitro</i< experiments, where a reduction in AFB1-induced cytotoxicity and DNA single-strand and double-strand breaks was observed in cells exposed to combinations of AFB1 and XN, highlighting the chemoprotective effects of this phytochemical. xanthohumol isoxanthohumol 8-prenylnaringenin: 6-prenylnaringenin aflatoxin B1 aflatoxin B1 exo-8,9-epoxide genotoxicity Chemical technology Veronika Furlan verfasserin aut Matjaž Novak verfasserin aut Martina Štampar verfasserin aut Zala Kolenc verfasserin aut Katarina Kores verfasserin aut Metka Filipič verfasserin aut Urban Bren verfasserin aut Bojana Žegura verfasserin aut In Foods MDPI AG, 2013 10(2021), 6, p 1331 (DE-627)737287632 (DE-600)2704223-6 23048158 nnns volume:10 year:2021 number:6, p 1331 https://doi.org/10.3390/foods10061331 kostenfrei https://doaj.org/article/81b7b413fa14461b885caa07c50fef7b kostenfrei https://www.mdpi.com/2304-8158/10/6/1331 kostenfrei https://doaj.org/toc/2304-8158 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_24 GBV_ILN_31 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_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 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 10 2021 6, p 1331
allfieldsSound	10.3390/foods10061331 doi (DE-627)DOAJ00336996X (DE-599)DOAJ81b7b413fa14461b885caa07c50fef7b DE-627 ger DE-627 rakwb eng TP1-1185 Alja Štern verfasserin aut Chemoprotective Effects of Xanthohumol against the Carcinogenic Mycotoxin Aflatoxin B1 2021 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The present study addresses the chemoprotective effects of xanthohumol (XN), a prenylated flavonoid found in the female inflorescences (hops) of the plant <i<Humulus lupulus</i< L., against the carcinogenic food contaminant aflatoxin B1 (AFB1). The chemical reactions of XN and its derivatives (isoxanthohumol (IXN), 8-prenylnaringenin (8-PN), and 6-prenylnaringenin (6-PN)) with the AFB1 metabolite, aflatoxin B1 exo-8,9-epoxide (AFBO), were investigated <i<in silico</i<, by calculating activation free energies (ΔG<sup<‡</sup<) at the Hartree–Fock level of theory in combination with the 6-311++G(d,p) basis set and two implicit solvation models. The chemoprotective effects of XN were investigated <i<in vitro</i< in the metabolically competent HepG2 cell line, analyzing its influence on AFB1-induced cytotoxicity using the MTS assay, genotoxicity using the comet and γH2AX assays, and cell cycle modulation using flow cytometry. Our results show that the ΔG<sup<‡</sup< required for the reactions of XN and its derivatives with AFBO are comparable to the ΔG<sup<‡</sup< required for the reaction of AFBO with guanine, indicating that XN, IXN, 8-PN, and 6-PN could act as scavengers of AFBO, preventing DNA adduct formation and DNA damage induction. This was also reflected in the results from the <i<in vitro</i< experiments, where a reduction in AFB1-induced cytotoxicity and DNA single-strand and double-strand breaks was observed in cells exposed to combinations of AFB1 and XN, highlighting the chemoprotective effects of this phytochemical. xanthohumol isoxanthohumol 8-prenylnaringenin: 6-prenylnaringenin aflatoxin B1 aflatoxin B1 exo-8,9-epoxide genotoxicity Chemical technology Veronika Furlan verfasserin aut Matjaž Novak verfasserin aut Martina Štampar verfasserin aut Zala Kolenc verfasserin aut Katarina Kores verfasserin aut Metka Filipič verfasserin aut Urban Bren verfasserin aut Bojana Žegura verfasserin aut In Foods MDPI AG, 2013 10(2021), 6, p 1331 (DE-627)737287632 (DE-600)2704223-6 23048158 nnns volume:10 year:2021 number:6, p 1331 https://doi.org/10.3390/foods10061331 kostenfrei https://doaj.org/article/81b7b413fa14461b885caa07c50fef7b kostenfrei https://www.mdpi.com/2304-8158/10/6/1331 kostenfrei https://doaj.org/toc/2304-8158 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_24 GBV_ILN_31 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_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 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 10 2021 6, p 1331
language	English
source	In Foods 10(2021), 6, p 1331 volume:10 year:2021 number:6, p 1331
sourceStr	In Foods 10(2021), 6, p 1331 volume:10 year:2021 number:6, p 1331
format_phy_str_mv	Article
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topic_facet	xanthohumol isoxanthohumol 8-prenylnaringenin: 6-prenylnaringenin aflatoxin B1 aflatoxin B1 exo-8,9-epoxide genotoxicity Chemical technology
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authorswithroles_txt_mv	Alja Štern @@aut@@ Veronika Furlan @@aut@@ Matjaž Novak @@aut@@ Martina Štampar @@aut@@ Zala Kolenc @@aut@@ Katarina Kores @@aut@@ Metka Filipič @@aut@@ Urban Bren @@aut@@ Bojana Žegura @@aut@@
publishDateDaySort_date	2021-01-01T00:00:00Z
hierarchy_top_id	737287632
id	DOAJ00336996X
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callnumber-first	T - Technology
author	Alja Štern
spellingShingle	Alja Štern misc TP1-1185 misc xanthohumol misc isoxanthohumol misc 8-prenylnaringenin: 6-prenylnaringenin misc aflatoxin B1 misc aflatoxin B1 exo-8,9-epoxide misc genotoxicity misc Chemical technology Chemoprotective Effects of Xanthohumol against the Carcinogenic Mycotoxin Aflatoxin B1
authorStr	Alja Štern
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topic_title	TP1-1185 Chemoprotective Effects of Xanthohumol against the Carcinogenic Mycotoxin Aflatoxin B1 xanthohumol isoxanthohumol 8-prenylnaringenin: 6-prenylnaringenin aflatoxin B1 aflatoxin B1 exo-8,9-epoxide genotoxicity
topic	misc TP1-1185 misc xanthohumol misc isoxanthohumol misc 8-prenylnaringenin: 6-prenylnaringenin misc aflatoxin B1 misc aflatoxin B1 exo-8,9-epoxide misc genotoxicity misc Chemical technology
topic_unstemmed	misc TP1-1185 misc xanthohumol misc isoxanthohumol misc 8-prenylnaringenin: 6-prenylnaringenin misc aflatoxin B1 misc aflatoxin B1 exo-8,9-epoxide misc genotoxicity misc Chemical technology
topic_browse	misc TP1-1185 misc xanthohumol misc isoxanthohumol misc 8-prenylnaringenin: 6-prenylnaringenin misc aflatoxin B1 misc aflatoxin B1 exo-8,9-epoxide misc genotoxicity misc Chemical technology
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title	Chemoprotective Effects of Xanthohumol against the Carcinogenic Mycotoxin Aflatoxin B1
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title_full	Chemoprotective Effects of Xanthohumol against the Carcinogenic Mycotoxin Aflatoxin B1
author_sort	Alja Štern
journal	Foods
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author_browse	Alja Štern Veronika Furlan Matjaž Novak Martina Štampar Zala Kolenc Katarina Kores Metka Filipič Urban Bren Bojana Žegura
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author-letter	Alja Štern
doi_str_mv	10.3390/foods10061331
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title_sort	chemoprotective effects of xanthohumol against the carcinogenic mycotoxin aflatoxin b1
callnumber	TP1-1185
title_auth	Chemoprotective Effects of Xanthohumol against the Carcinogenic Mycotoxin Aflatoxin B1
abstract	The present study addresses the chemoprotective effects of xanthohumol (XN), a prenylated flavonoid found in the female inflorescences (hops) of the plant <i<Humulus lupulus</i< L., against the carcinogenic food contaminant aflatoxin B1 (AFB1). The chemical reactions of XN and its derivatives (isoxanthohumol (IXN), 8-prenylnaringenin (8-PN), and 6-prenylnaringenin (6-PN)) with the AFB1 metabolite, aflatoxin B1 exo-8,9-epoxide (AFBO), were investigated <i<in silico</i<, by calculating activation free energies (ΔG<sup<‡</sup<) at the Hartree–Fock level of theory in combination with the 6-311++G(d,p) basis set and two implicit solvation models. The chemoprotective effects of XN were investigated <i<in vitro</i< in the metabolically competent HepG2 cell line, analyzing its influence on AFB1-induced cytotoxicity using the MTS assay, genotoxicity using the comet and γH2AX assays, and cell cycle modulation using flow cytometry. Our results show that the ΔG<sup<‡</sup< required for the reactions of XN and its derivatives with AFBO are comparable to the ΔG<sup<‡</sup< required for the reaction of AFBO with guanine, indicating that XN, IXN, 8-PN, and 6-PN could act as scavengers of AFBO, preventing DNA adduct formation and DNA damage induction. This was also reflected in the results from the <i<in vitro</i< experiments, where a reduction in AFB1-induced cytotoxicity and DNA single-strand and double-strand breaks was observed in cells exposed to combinations of AFB1 and XN, highlighting the chemoprotective effects of this phytochemical.
abstractGer	The present study addresses the chemoprotective effects of xanthohumol (XN), a prenylated flavonoid found in the female inflorescences (hops) of the plant <i<Humulus lupulus</i< L., against the carcinogenic food contaminant aflatoxin B1 (AFB1). The chemical reactions of XN and its derivatives (isoxanthohumol (IXN), 8-prenylnaringenin (8-PN), and 6-prenylnaringenin (6-PN)) with the AFB1 metabolite, aflatoxin B1 exo-8,9-epoxide (AFBO), were investigated <i<in silico</i<, by calculating activation free energies (ΔG<sup<‡</sup<) at the Hartree–Fock level of theory in combination with the 6-311++G(d,p) basis set and two implicit solvation models. The chemoprotective effects of XN were investigated <i<in vitro</i< in the metabolically competent HepG2 cell line, analyzing its influence on AFB1-induced cytotoxicity using the MTS assay, genotoxicity using the comet and γH2AX assays, and cell cycle modulation using flow cytometry. Our results show that the ΔG<sup<‡</sup< required for the reactions of XN and its derivatives with AFBO are comparable to the ΔG<sup<‡</sup< required for the reaction of AFBO with guanine, indicating that XN, IXN, 8-PN, and 6-PN could act as scavengers of AFBO, preventing DNA adduct formation and DNA damage induction. This was also reflected in the results from the <i<in vitro</i< experiments, where a reduction in AFB1-induced cytotoxicity and DNA single-strand and double-strand breaks was observed in cells exposed to combinations of AFB1 and XN, highlighting the chemoprotective effects of this phytochemical.
abstract_unstemmed	The present study addresses the chemoprotective effects of xanthohumol (XN), a prenylated flavonoid found in the female inflorescences (hops) of the plant <i<Humulus lupulus</i< L., against the carcinogenic food contaminant aflatoxin B1 (AFB1). The chemical reactions of XN and its derivatives (isoxanthohumol (IXN), 8-prenylnaringenin (8-PN), and 6-prenylnaringenin (6-PN)) with the AFB1 metabolite, aflatoxin B1 exo-8,9-epoxide (AFBO), were investigated <i<in silico</i<, by calculating activation free energies (ΔG<sup<‡</sup<) at the Hartree–Fock level of theory in combination with the 6-311++G(d,p) basis set and two implicit solvation models. The chemoprotective effects of XN were investigated <i<in vitro</i< in the metabolically competent HepG2 cell line, analyzing its influence on AFB1-induced cytotoxicity using the MTS assay, genotoxicity using the comet and γH2AX assays, and cell cycle modulation using flow cytometry. Our results show that the ΔG<sup<‡</sup< required for the reactions of XN and its derivatives with AFBO are comparable to the ΔG<sup<‡</sup< required for the reaction of AFBO with guanine, indicating that XN, IXN, 8-PN, and 6-PN could act as scavengers of AFBO, preventing DNA adduct formation and DNA damage induction. This was also reflected in the results from the <i<in vitro</i< experiments, where a reduction in AFB1-induced cytotoxicity and DNA single-strand and double-strand breaks was observed in cells exposed to combinations of AFB1 and XN, highlighting the chemoprotective effects of this phytochemical.
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container_issue	6, p 1331
title_short	Chemoprotective Effects of Xanthohumol against the Carcinogenic Mycotoxin Aflatoxin B1
url	https://doi.org/10.3390/foods10061331 https://doaj.org/article/81b7b413fa14461b885caa07c50fef7b https://www.mdpi.com/2304-8158/10/6/1331 https://doaj.org/toc/2304-8158
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author2	Veronika Furlan Matjaž Novak Martina Štampar Zala Kolenc Katarina Kores Metka Filipič Urban Bren Bojana Žegura
author2Str	Veronika Furlan Matjaž Novak Martina Štampar Zala Kolenc Katarina Kores Metka Filipič Urban Bren Bojana Žegura
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doi_str	10.3390/foods10061331
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up_date	2024-07-03T17:36:16.956Z
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