Potential Industrial Production of a Well-Soluble, Alkaline-Stable, and Anti-Inflammatory Isoflavone Glucoside from 8-Hydroxydaidzein Glucosylated by Recombinant Amylosucrase of <i<Deinococcus geothermalis</i<

8-Hydroxydaidzein (8-OHDe), an <i<ortho</i<-hydroxylation derivative of soy isoflavone daidzein isolated from some fermented soybean foods, has been demonstrated to possess potent anti-inflammatory activity. However, the isoflavone aglycone is poorly soluble and unstable in alkaline solu...
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Gespeichert in:

Autor*in:	Te-Sheng Chang [verfasserIn] Tzi-Yuan Wang [verfasserIn] Szu-Yi Yang [verfasserIn] Yu-Han Kao [verfasserIn] Jiumn-Yih Wu [verfasserIn] Chien-Min Chiang [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2019

Schlagwörter:	8-hydroxydaidzein stable soluble anti-inflammation amylosucrase

Übergeordnetes Werk:	In: Molecules - MDPI AG, 2003, 24(2019), 12, p 2236
Übergeordnetes Werk:	volume:24 ; year:2019 ; number:12, p 2236

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.3390/molecules24122236

Katalog-ID:	DOAJ010085742

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520			\|a 8-Hydroxydaidzein (8-OHDe), an <i<ortho</i<-hydroxylation derivative of soy isoflavone daidzein isolated from some fermented soybean foods, has been demonstrated to possess potent anti-inflammatory activity. However, the isoflavone aglycone is poorly soluble and unstable in alkaline solutions. To improve the aqueous solubility and stability of the functional isoflavone, 8-OHDe was glucosylated with recombinant amylosucrase of <i<Deinococcus geothermalis</i< (DgAS) with industrial sucrose, instead of expensive uridine diphosphate-glucose (UDP-glucose). One major product was produced from the biotransformation, and identified as 8-OHDe-7-α-glucoside, based on mass and nuclear magnetic resonance spectral analyses. The aqueous solubility and stability of the isoflavone glucoside were determined, and the results showed that the isoflavone glucoside was almost 4-fold more soluble and more than six-fold higher alkaline-stable than 8-OHDe. In addition, the anti-inflammatory activity of 8-OHDe-7-α-glucoside was also determined by the inhibition of lipopolysaccharide-induced nitric oxide production in RAW 264.7 cells. The results showed that 8-OHDe-7-α-glucoside exhibited significant and dose-dependent inhibition on the production of nitric oxide, with an IC<sub<50</sub< value of 173.2 µM, which remained 20% of the anti-inflammatory activity of 8-OHDe. In conclusion, the well-soluble and alkaline-stable 8-OHDe-7-α-glucoside produced by recombinant DgAS with a cheap substrate, sucrose, as a sugar donor retains moderate anti-inflammatory activity, and could be used in industrial applications in the future.
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allfields	10.3390/molecules24122236 doi (DE-627)DOAJ010085742 (DE-599)DOAJ70e0a38ac8814f1d83d1407a10f49f25 DE-627 ger DE-627 rakwb eng QD241-441 Te-Sheng Chang verfasserin aut Potential Industrial Production of a Well-Soluble, Alkaline-Stable, and Anti-Inflammatory Isoflavone Glucoside from 8-Hydroxydaidzein Glucosylated by Recombinant Amylosucrase of <i<Deinococcus geothermalis</i< 2019 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier 8-Hydroxydaidzein (8-OHDe), an <i<ortho</i<-hydroxylation derivative of soy isoflavone daidzein isolated from some fermented soybean foods, has been demonstrated to possess potent anti-inflammatory activity. However, the isoflavone aglycone is poorly soluble and unstable in alkaline solutions. To improve the aqueous solubility and stability of the functional isoflavone, 8-OHDe was glucosylated with recombinant amylosucrase of <i<Deinococcus geothermalis</i< (DgAS) with industrial sucrose, instead of expensive uridine diphosphate-glucose (UDP-glucose). One major product was produced from the biotransformation, and identified as 8-OHDe-7-α-glucoside, based on mass and nuclear magnetic resonance spectral analyses. The aqueous solubility and stability of the isoflavone glucoside were determined, and the results showed that the isoflavone glucoside was almost 4-fold more soluble and more than six-fold higher alkaline-stable than 8-OHDe. In addition, the anti-inflammatory activity of 8-OHDe-7-α-glucoside was also determined by the inhibition of lipopolysaccharide-induced nitric oxide production in RAW 264.7 cells. The results showed that 8-OHDe-7-α-glucoside exhibited significant and dose-dependent inhibition on the production of nitric oxide, with an IC<sub<50</sub< value of 173.2 µM, which remained 20% of the anti-inflammatory activity of 8-OHDe. In conclusion, the well-soluble and alkaline-stable 8-OHDe-7-α-glucoside produced by recombinant DgAS with a cheap substrate, sucrose, as a sugar donor retains moderate anti-inflammatory activity, and could be used in industrial applications in the future. 8-hydroxydaidzein stable soluble anti-inflammation amylosucrase <i<Deinococcus geothermalis</i< Organic chemistry Tzi-Yuan Wang verfasserin aut Szu-Yi Yang verfasserin aut Yu-Han Kao verfasserin aut Jiumn-Yih Wu verfasserin aut Chien-Min Chiang verfasserin aut In Molecules MDPI AG, 2003 24(2019), 12, p 2236 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:24 year:2019 number:12, p 2236 https://doi.org/10.3390/molecules24122236 kostenfrei https://doaj.org/article/70e0a38ac8814f1d83d1407a10f49f25 kostenfrei https://www.mdpi.com/1420-3049/24/12/2236 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 24 2019 12, p 2236
spelling	10.3390/molecules24122236 doi (DE-627)DOAJ010085742 (DE-599)DOAJ70e0a38ac8814f1d83d1407a10f49f25 DE-627 ger DE-627 rakwb eng QD241-441 Te-Sheng Chang verfasserin aut Potential Industrial Production of a Well-Soluble, Alkaline-Stable, and Anti-Inflammatory Isoflavone Glucoside from 8-Hydroxydaidzein Glucosylated by Recombinant Amylosucrase of <i<Deinococcus geothermalis</i< 2019 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier 8-Hydroxydaidzein (8-OHDe), an <i<ortho</i<-hydroxylation derivative of soy isoflavone daidzein isolated from some fermented soybean foods, has been demonstrated to possess potent anti-inflammatory activity. However, the isoflavone aglycone is poorly soluble and unstable in alkaline solutions. To improve the aqueous solubility and stability of the functional isoflavone, 8-OHDe was glucosylated with recombinant amylosucrase of <i<Deinococcus geothermalis</i< (DgAS) with industrial sucrose, instead of expensive uridine diphosphate-glucose (UDP-glucose). One major product was produced from the biotransformation, and identified as 8-OHDe-7-α-glucoside, based on mass and nuclear magnetic resonance spectral analyses. The aqueous solubility and stability of the isoflavone glucoside were determined, and the results showed that the isoflavone glucoside was almost 4-fold more soluble and more than six-fold higher alkaline-stable than 8-OHDe. In addition, the anti-inflammatory activity of 8-OHDe-7-α-glucoside was also determined by the inhibition of lipopolysaccharide-induced nitric oxide production in RAW 264.7 cells. The results showed that 8-OHDe-7-α-glucoside exhibited significant and dose-dependent inhibition on the production of nitric oxide, with an IC<sub<50</sub< value of 173.2 µM, which remained 20% of the anti-inflammatory activity of 8-OHDe. In conclusion, the well-soluble and alkaline-stable 8-OHDe-7-α-glucoside produced by recombinant DgAS with a cheap substrate, sucrose, as a sugar donor retains moderate anti-inflammatory activity, and could be used in industrial applications in the future. 8-hydroxydaidzein stable soluble anti-inflammation amylosucrase <i<Deinococcus geothermalis</i< Organic chemistry Tzi-Yuan Wang verfasserin aut Szu-Yi Yang verfasserin aut Yu-Han Kao verfasserin aut Jiumn-Yih Wu verfasserin aut Chien-Min Chiang verfasserin aut In Molecules MDPI AG, 2003 24(2019), 12, p 2236 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:24 year:2019 number:12, p 2236 https://doi.org/10.3390/molecules24122236 kostenfrei https://doaj.org/article/70e0a38ac8814f1d83d1407a10f49f25 kostenfrei https://www.mdpi.com/1420-3049/24/12/2236 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 24 2019 12, p 2236
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allfieldsGer	10.3390/molecules24122236 doi (DE-627)DOAJ010085742 (DE-599)DOAJ70e0a38ac8814f1d83d1407a10f49f25 DE-627 ger DE-627 rakwb eng QD241-441 Te-Sheng Chang verfasserin aut Potential Industrial Production of a Well-Soluble, Alkaline-Stable, and Anti-Inflammatory Isoflavone Glucoside from 8-Hydroxydaidzein Glucosylated by Recombinant Amylosucrase of <i<Deinococcus geothermalis</i< 2019 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier 8-Hydroxydaidzein (8-OHDe), an <i<ortho</i<-hydroxylation derivative of soy isoflavone daidzein isolated from some fermented soybean foods, has been demonstrated to possess potent anti-inflammatory activity. However, the isoflavone aglycone is poorly soluble and unstable in alkaline solutions. To improve the aqueous solubility and stability of the functional isoflavone, 8-OHDe was glucosylated with recombinant amylosucrase of <i<Deinococcus geothermalis</i< (DgAS) with industrial sucrose, instead of expensive uridine diphosphate-glucose (UDP-glucose). One major product was produced from the biotransformation, and identified as 8-OHDe-7-α-glucoside, based on mass and nuclear magnetic resonance spectral analyses. The aqueous solubility and stability of the isoflavone glucoside were determined, and the results showed that the isoflavone glucoside was almost 4-fold more soluble and more than six-fold higher alkaline-stable than 8-OHDe. In addition, the anti-inflammatory activity of 8-OHDe-7-α-glucoside was also determined by the inhibition of lipopolysaccharide-induced nitric oxide production in RAW 264.7 cells. The results showed that 8-OHDe-7-α-glucoside exhibited significant and dose-dependent inhibition on the production of nitric oxide, with an IC<sub<50</sub< value of 173.2 µM, which remained 20% of the anti-inflammatory activity of 8-OHDe. In conclusion, the well-soluble and alkaline-stable 8-OHDe-7-α-glucoside produced by recombinant DgAS with a cheap substrate, sucrose, as a sugar donor retains moderate anti-inflammatory activity, and could be used in industrial applications in the future. 8-hydroxydaidzein stable soluble anti-inflammation amylosucrase <i<Deinococcus geothermalis</i< Organic chemistry Tzi-Yuan Wang verfasserin aut Szu-Yi Yang verfasserin aut Yu-Han Kao verfasserin aut Jiumn-Yih Wu verfasserin aut Chien-Min Chiang verfasserin aut In Molecules MDPI AG, 2003 24(2019), 12, p 2236 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:24 year:2019 number:12, p 2236 https://doi.org/10.3390/molecules24122236 kostenfrei https://doaj.org/article/70e0a38ac8814f1d83d1407a10f49f25 kostenfrei https://www.mdpi.com/1420-3049/24/12/2236 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 24 2019 12, p 2236
allfieldsSound	10.3390/molecules24122236 doi (DE-627)DOAJ010085742 (DE-599)DOAJ70e0a38ac8814f1d83d1407a10f49f25 DE-627 ger DE-627 rakwb eng QD241-441 Te-Sheng Chang verfasserin aut Potential Industrial Production of a Well-Soluble, Alkaline-Stable, and Anti-Inflammatory Isoflavone Glucoside from 8-Hydroxydaidzein Glucosylated by Recombinant Amylosucrase of <i<Deinococcus geothermalis</i< 2019 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier 8-Hydroxydaidzein (8-OHDe), an <i<ortho</i<-hydroxylation derivative of soy isoflavone daidzein isolated from some fermented soybean foods, has been demonstrated to possess potent anti-inflammatory activity. However, the isoflavone aglycone is poorly soluble and unstable in alkaline solutions. To improve the aqueous solubility and stability of the functional isoflavone, 8-OHDe was glucosylated with recombinant amylosucrase of <i<Deinococcus geothermalis</i< (DgAS) with industrial sucrose, instead of expensive uridine diphosphate-glucose (UDP-glucose). One major product was produced from the biotransformation, and identified as 8-OHDe-7-α-glucoside, based on mass and nuclear magnetic resonance spectral analyses. The aqueous solubility and stability of the isoflavone glucoside were determined, and the results showed that the isoflavone glucoside was almost 4-fold more soluble and more than six-fold higher alkaline-stable than 8-OHDe. In addition, the anti-inflammatory activity of 8-OHDe-7-α-glucoside was also determined by the inhibition of lipopolysaccharide-induced nitric oxide production in RAW 264.7 cells. The results showed that 8-OHDe-7-α-glucoside exhibited significant and dose-dependent inhibition on the production of nitric oxide, with an IC<sub<50</sub< value of 173.2 µM, which remained 20% of the anti-inflammatory activity of 8-OHDe. In conclusion, the well-soluble and alkaline-stable 8-OHDe-7-α-glucoside produced by recombinant DgAS with a cheap substrate, sucrose, as a sugar donor retains moderate anti-inflammatory activity, and could be used in industrial applications in the future. 8-hydroxydaidzein stable soluble anti-inflammation amylosucrase <i<Deinococcus geothermalis</i< Organic chemistry Tzi-Yuan Wang verfasserin aut Szu-Yi Yang verfasserin aut Yu-Han Kao verfasserin aut Jiumn-Yih Wu verfasserin aut Chien-Min Chiang verfasserin aut In Molecules MDPI AG, 2003 24(2019), 12, p 2236 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:24 year:2019 number:12, p 2236 https://doi.org/10.3390/molecules24122236 kostenfrei https://doaj.org/article/70e0a38ac8814f1d83d1407a10f49f25 kostenfrei https://www.mdpi.com/1420-3049/24/12/2236 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 24 2019 12, p 2236
language	English
source	In Molecules 24(2019), 12, p 2236 volume:24 year:2019 number:12, p 2236
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topic_facet	8-hydroxydaidzein stable soluble anti-inflammation amylosucrase <i<Deinococcus geothermalis</i< Organic chemistry
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authorswithroles_txt_mv	Te-Sheng Chang @@aut@@ Tzi-Yuan Wang @@aut@@ Szu-Yi Yang @@aut@@ Yu-Han Kao @@aut@@ Jiumn-Yih Wu @@aut@@ Chien-Min Chiang @@aut@@
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callnumber-label	QD241-441
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issn	14203049
topic_title	QD241-441 Potential Industrial Production of a Well-Soluble, Alkaline-Stable, and Anti-Inflammatory Isoflavone Glucoside from 8-Hydroxydaidzein Glucosylated by Recombinant Amylosucrase of <i<Deinococcus geothermalis</i< 8-hydroxydaidzein stable soluble anti-inflammation amylosucrase <i<Deinococcus geothermalis</i<
topic	misc QD241-441 misc 8-hydroxydaidzein misc stable misc soluble misc anti-inflammation misc amylosucrase misc <i<Deinococcus geothermalis</i< misc Organic chemistry
topic_unstemmed	misc QD241-441 misc 8-hydroxydaidzein misc stable misc soluble misc anti-inflammation misc amylosucrase misc <i<Deinococcus geothermalis</i< misc Organic chemistry
topic_browse	misc QD241-441 misc 8-hydroxydaidzein misc stable misc soluble misc anti-inflammation misc amylosucrase misc <i<Deinococcus geothermalis</i< misc Organic chemistry
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title	Potential Industrial Production of a Well-Soluble, Alkaline-Stable, and Anti-Inflammatory Isoflavone Glucoside from 8-Hydroxydaidzein Glucosylated by Recombinant Amylosucrase of <i<Deinococcus geothermalis</i<
ctrlnum	(DE-627)DOAJ010085742 (DE-599)DOAJ70e0a38ac8814f1d83d1407a10f49f25
title_full	Potential Industrial Production of a Well-Soluble, Alkaline-Stable, and Anti-Inflammatory Isoflavone Glucoside from 8-Hydroxydaidzein Glucosylated by Recombinant Amylosucrase of <i<Deinococcus geothermalis</i<
author_sort	Te-Sheng Chang
journal	Molecules
journalStr	Molecules
callnumber-first-code	Q
lang_code	eng
isOA_bool	true
recordtype	marc
publishDateSort	2019
contenttype_str_mv	txt
author_browse	Te-Sheng Chang Tzi-Yuan Wang Szu-Yi Yang Yu-Han Kao Jiumn-Yih Wu Chien-Min Chiang
container_volume	24
class	QD241-441
format_se	Elektronische Aufsätze
author-letter	Te-Sheng Chang
doi_str_mv	10.3390/molecules24122236
author2-role	verfasserin
title_sort	potential industrial production of a well-soluble, alkaline-stable, and anti-inflammatory isoflavone glucoside from 8-hydroxydaidzein glucosylated by recombinant amylosucrase of <i<deinococcus geothermalis</i<
callnumber	QD241-441
title_auth	Potential Industrial Production of a Well-Soluble, Alkaline-Stable, and Anti-Inflammatory Isoflavone Glucoside from 8-Hydroxydaidzein Glucosylated by Recombinant Amylosucrase of <i<Deinococcus geothermalis</i<
abstract	8-Hydroxydaidzein (8-OHDe), an <i<ortho</i<-hydroxylation derivative of soy isoflavone daidzein isolated from some fermented soybean foods, has been demonstrated to possess potent anti-inflammatory activity. However, the isoflavone aglycone is poorly soluble and unstable in alkaline solutions. To improve the aqueous solubility and stability of the functional isoflavone, 8-OHDe was glucosylated with recombinant amylosucrase of <i<Deinococcus geothermalis</i< (DgAS) with industrial sucrose, instead of expensive uridine diphosphate-glucose (UDP-glucose). One major product was produced from the biotransformation, and identified as 8-OHDe-7-α-glucoside, based on mass and nuclear magnetic resonance spectral analyses. The aqueous solubility and stability of the isoflavone glucoside were determined, and the results showed that the isoflavone glucoside was almost 4-fold more soluble and more than six-fold higher alkaline-stable than 8-OHDe. In addition, the anti-inflammatory activity of 8-OHDe-7-α-glucoside was also determined by the inhibition of lipopolysaccharide-induced nitric oxide production in RAW 264.7 cells. The results showed that 8-OHDe-7-α-glucoside exhibited significant and dose-dependent inhibition on the production of nitric oxide, with an IC<sub<50</sub< value of 173.2 µM, which remained 20% of the anti-inflammatory activity of 8-OHDe. In conclusion, the well-soluble and alkaline-stable 8-OHDe-7-α-glucoside produced by recombinant DgAS with a cheap substrate, sucrose, as a sugar donor retains moderate anti-inflammatory activity, and could be used in industrial applications in the future.
abstractGer	8-Hydroxydaidzein (8-OHDe), an <i<ortho</i<-hydroxylation derivative of soy isoflavone daidzein isolated from some fermented soybean foods, has been demonstrated to possess potent anti-inflammatory activity. However, the isoflavone aglycone is poorly soluble and unstable in alkaline solutions. To improve the aqueous solubility and stability of the functional isoflavone, 8-OHDe was glucosylated with recombinant amylosucrase of <i<Deinococcus geothermalis</i< (DgAS) with industrial sucrose, instead of expensive uridine diphosphate-glucose (UDP-glucose). One major product was produced from the biotransformation, and identified as 8-OHDe-7-α-glucoside, based on mass and nuclear magnetic resonance spectral analyses. The aqueous solubility and stability of the isoflavone glucoside were determined, and the results showed that the isoflavone glucoside was almost 4-fold more soluble and more than six-fold higher alkaline-stable than 8-OHDe. In addition, the anti-inflammatory activity of 8-OHDe-7-α-glucoside was also determined by the inhibition of lipopolysaccharide-induced nitric oxide production in RAW 264.7 cells. The results showed that 8-OHDe-7-α-glucoside exhibited significant and dose-dependent inhibition on the production of nitric oxide, with an IC<sub<50</sub< value of 173.2 µM, which remained 20% of the anti-inflammatory activity of 8-OHDe. In conclusion, the well-soluble and alkaline-stable 8-OHDe-7-α-glucoside produced by recombinant DgAS with a cheap substrate, sucrose, as a sugar donor retains moderate anti-inflammatory activity, and could be used in industrial applications in the future.
abstract_unstemmed	8-Hydroxydaidzein (8-OHDe), an <i<ortho</i<-hydroxylation derivative of soy isoflavone daidzein isolated from some fermented soybean foods, has been demonstrated to possess potent anti-inflammatory activity. However, the isoflavone aglycone is poorly soluble and unstable in alkaline solutions. To improve the aqueous solubility and stability of the functional isoflavone, 8-OHDe was glucosylated with recombinant amylosucrase of <i<Deinococcus geothermalis</i< (DgAS) with industrial sucrose, instead of expensive uridine diphosphate-glucose (UDP-glucose). One major product was produced from the biotransformation, and identified as 8-OHDe-7-α-glucoside, based on mass and nuclear magnetic resonance spectral analyses. The aqueous solubility and stability of the isoflavone glucoside were determined, and the results showed that the isoflavone glucoside was almost 4-fold more soluble and more than six-fold higher alkaline-stable than 8-OHDe. In addition, the anti-inflammatory activity of 8-OHDe-7-α-glucoside was also determined by the inhibition of lipopolysaccharide-induced nitric oxide production in RAW 264.7 cells. The results showed that 8-OHDe-7-α-glucoside exhibited significant and dose-dependent inhibition on the production of nitric oxide, with an IC<sub<50</sub< value of 173.2 µM, which remained 20% of the anti-inflammatory activity of 8-OHDe. In conclusion, the well-soluble and alkaline-stable 8-OHDe-7-α-glucoside produced by recombinant DgAS with a cheap substrate, sucrose, as a sugar donor retains moderate anti-inflammatory activity, and could be used in industrial applications in the future.
collection_details	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
container_issue	12, p 2236
title_short	Potential Industrial Production of a Well-Soluble, Alkaline-Stable, and Anti-Inflammatory Isoflavone Glucoside from 8-Hydroxydaidzein Glucosylated by Recombinant Amylosucrase of <i<Deinococcus geothermalis</i<
url	https://doi.org/10.3390/molecules24122236 https://doaj.org/article/70e0a38ac8814f1d83d1407a10f49f25 https://www.mdpi.com/1420-3049/24/12/2236 https://doaj.org/toc/1420-3049
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author2	Tzi-Yuan Wang Szu-Yi Yang Yu-Han Kao Jiumn-Yih Wu Chien-Min Chiang
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doi_str	10.3390/molecules24122236
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up_date	2024-07-04T02:10:18.758Z
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Potential Industrial Production of a Well-Soluble, Alkaline-Stable, and Anti-Inflammatory Isoflavone Glucoside from 8-Hydroxydaidzein Glucosylated by Recombinant Amylosucrase of <i<Deinococcus geothermalis</i<

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