Production of high antioxidant activity flavonoid monoglucosides from citrus flavanone with immobilised α‐L‐rhamnosidase in one step
Summary The rhamnosyl group of naringin dihydrochalcone, neohesperidin dihydrochalcone, naringin and hesperidin was selectively removed by enzymatic hydrolysis using an immobilised α‐L‐rhamnosidase. Monoglycosylated products, including trilobatin, hesperetin dihydrochalcone‐7‐O‐glucoside, prunin and...
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Published in | International journal of food science & technology Vol. 54; no. 10; pp. 2854 - 2862 |
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Main Authors | , , , , , |
Format | Journal Article |
Language | English |
Published |
Oxford
Wiley Subscription Services, Inc
01.10.2019
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Abstract | Summary
The rhamnosyl group of naringin dihydrochalcone, neohesperidin dihydrochalcone, naringin and hesperidin was selectively removed by enzymatic hydrolysis using an immobilised α‐L‐rhamnosidase. Monoglycosylated products, including trilobatin, hesperetin dihydrochalcone‐7‐O‐glucoside, prunin and hesperetin‐7‐O‐glucoside, were isolated and characterised by 1H and 13C NMR and ESI‐MS. To optimise the enzymatic reaction conditions and its process costs, the hydrolysis of neohesperidin dihydrochalcone to produce trilobatin was selected as a model reaction. Using a ratio of neohesperidin dihydrochalcone: immobilised α‐L‐rhamnosidase equal to 1:0.6, the trilobatin yields was over 98%. The recycle of enzyme was also investigated, obtaining trilobatin with a yields of 80% even when the twentieth reaction cycle was conducted. Moreover, antiradical and antimicrobial activities of the obtained flavonoid monoglucosides were examined by DPPH, FRAP and ORAC methods, and compared with the efficacy of parental flavonoid glycosides and their aglycone. The results highlight that some of the obtained flavonoid monoglucosides show significant improvement in the antioxidant activity.
The enzymatic hydrolysis of flavonoid diglycosides, selectively removing the rhamnosyl groups, with an immobilised α‐L‐rhamnosidase is able to produce flavonoid monoglucosides that possess better functionalities for further applications. Some of these flavonoid monoglucosides obtained show significant improvement in the antioxidant activity. |
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AbstractList | Summary
The rhamnosyl group of naringin dihydrochalcone, neohesperidin dihydrochalcone, naringin and hesperidin was selectively removed by enzymatic hydrolysis using an immobilised α‐L‐rhamnosidase. Monoglycosylated products, including trilobatin, hesperetin dihydrochalcone‐7‐O‐glucoside, prunin and hesperetin‐7‐O‐glucoside, were isolated and characterised by
1
H and
13
C
NMR
and
ESI
‐
MS
. To optimise the enzymatic reaction conditions and its process costs, the hydrolysis of neohesperidin dihydrochalcone to produce trilobatin was selected as a model reaction. Using a ratio of neohesperidin dihydrochalcone: immobilised α‐L‐rhamnosidase equal to 1:0.6, the trilobatin yields was over 98%. The recycle of enzyme was also investigated, obtaining trilobatin with a yields of 80% even when the twentieth reaction cycle was conducted. Moreover, antiradical and antimicrobial activities of the obtained flavonoid monoglucosides were examined by
DPPH
,
FRAP
and
ORAC
methods, and compared with the efficacy of parental flavonoid glycosides and their aglycone. The results highlight that some of the obtained flavonoid monoglucosides show significant improvement in the antioxidant activity. The rhamnosyl group of naringin dihydrochalcone, neohesperidin dihydrochalcone, naringin and hesperidin was selectively removed by enzymatic hydrolysis using an immobilised α‐L‐rhamnosidase. Monoglycosylated products, including trilobatin, hesperetin dihydrochalcone‐7‐O‐glucoside, prunin and hesperetin‐7‐O‐glucoside, were isolated and characterised by 1H and 13C NMR and ESI‐MS. To optimise the enzymatic reaction conditions and its process costs, the hydrolysis of neohesperidin dihydrochalcone to produce trilobatin was selected as a model reaction. Using a ratio of neohesperidin dihydrochalcone: immobilised α‐L‐rhamnosidase equal to 1:0.6, the trilobatin yields was over 98%. The recycle of enzyme was also investigated, obtaining trilobatin with a yields of 80% even when the twentieth reaction cycle was conducted. Moreover, antiradical and antimicrobial activities of the obtained flavonoid monoglucosides were examined by DPPH, FRAP and ORAC methods, and compared with the efficacy of parental flavonoid glycosides and their aglycone. The results highlight that some of the obtained flavonoid monoglucosides show significant improvement in the antioxidant activity. Summary The rhamnosyl group of naringin dihydrochalcone, neohesperidin dihydrochalcone, naringin and hesperidin was selectively removed by enzymatic hydrolysis using an immobilised α‐L‐rhamnosidase. Monoglycosylated products, including trilobatin, hesperetin dihydrochalcone‐7‐O‐glucoside, prunin and hesperetin‐7‐O‐glucoside, were isolated and characterised by 1H and 13C NMR and ESI‐MS. To optimise the enzymatic reaction conditions and its process costs, the hydrolysis of neohesperidin dihydrochalcone to produce trilobatin was selected as a model reaction. Using a ratio of neohesperidin dihydrochalcone: immobilised α‐L‐rhamnosidase equal to 1:0.6, the trilobatin yields was over 98%. The recycle of enzyme was also investigated, obtaining trilobatin with a yields of 80% even when the twentieth reaction cycle was conducted. Moreover, antiradical and antimicrobial activities of the obtained flavonoid monoglucosides were examined by DPPH, FRAP and ORAC methods, and compared with the efficacy of parental flavonoid glycosides and their aglycone. The results highlight that some of the obtained flavonoid monoglucosides show significant improvement in the antioxidant activity. The enzymatic hydrolysis of flavonoid diglycosides, selectively removing the rhamnosyl groups, with an immobilised α‐L‐rhamnosidase is able to produce flavonoid monoglucosides that possess better functionalities for further applications. Some of these flavonoid monoglucosides obtained show significant improvement in the antioxidant activity. |
Author | Zhou, Jin‐Lin Huang, Baohua Lei, Lin Lu, Yu‐Jing Wong, Wing‐Leung Liu, Aolu |
Author_xml | – sequence: 1 givenname: Aolu surname: Liu fullname: Liu, Aolu organization: Guangdong University of Technology – sequence: 2 givenname: Baohua surname: Huang fullname: Huang, Baohua email: huangbh@gdut.edu.cn organization: Goldenpomelo Biotechnology Co. Ltd – sequence: 3 givenname: Lin surname: Lei fullname: Lei, Lin organization: Guangdong University of Technology – sequence: 4 givenname: Yu‐Jing surname: Lu fullname: Lu, Yu‐Jing organization: Goldenpomelo Biotechnology Co. Ltd – sequence: 5 givenname: Jin‐Lin surname: Zhou fullname: Zhou, Jin‐Lin organization: Goldenpomelo Biotechnology Co. Ltd – sequence: 6 givenname: Wing‐Leung orcidid: 0000-0001-7191-7578 surname: Wong fullname: Wong, Wing‐Leung email: wingleung@wyu.edu.cn organization: International Healthcare Innovation Institute (Jiangmen) |
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Cites_doi | 10.1016/S0963-9969(02)00064-9 10.1016/j.procbio.2017.07.012 10.1111/ijfs.13796 10.1016/j.foodchem.2011.07.030 10.1007/s13197-016-2228-6 10.1111/ijfs.13887 10.1016/j.biortech.2012.05.083 10.1021/jf0490807 10.1016/j.micpath.2017.03.033 10.1016/j.foodcont.2015.05.032 10.1016/j.ejmech.2017.07.034 10.1021/jf0341060 10.1021/jf00035a021 10.1007/s11418-017-1169-3 10.1016/j.foodchem.2014.06.022 10.1111/ijfs.13746 10.1111/ijfs.13877 10.1002/jctb.2433 10.1080/10715760000301181 10.1016/j.foodchem.2016.02.130 10.1016/j.jff.2014.01.032 10.3109/13880200490893492 10.1021/jf402711h 10.3109/09637480903292601 10.1371/journal.pone.0146013 10.1021/jf2040675 10.1021/jf0484632 10.1016/j.envexpbot.2011.04.019 10.1016/j.foodcont.2012.09.012 10.1016/j.foodchem.2017.02.029 10.1006/abio.1996.0292 10.3184/030823406778521455 10.1016/j.molcatb.2007.10.011 10.1021/jf60155a029 10.1007/s00217-006-0481-z 10.3390/antiox6010011 10.1016/j.resmic.2016.10.003 |
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The rhamnosyl group of naringin dihydrochalcone, neohesperidin dihydrochalcone, naringin and hesperidin was selectively removed by enzymatic hydrolysis... The rhamnosyl group of naringin dihydrochalcone, neohesperidin dihydrochalcone, naringin and hesperidin was selectively removed by enzymatic hydrolysis using... |
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SourceType | Aggregation Database Publisher |
StartPage | 2854 |
SubjectTerms | Antioxidants citrus flavanone Flavonoids Glucosides Glycosides Hesperidin Hydrolysis immobilised rhamnosidase monoglucosides Neohesperidin dihydrochalcone NMR Nuclear magnetic resonance |
Title | Production of high antioxidant activity flavonoid monoglucosides from citrus flavanone with immobilised α‐L‐rhamnosidase in one step |
URI | https://onlinelibrary.wiley.com/doi/abs/10.1111%2Fijfs.14202 https://www.proquest.com/docview/2290688096 |
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