Enhancement of debitterness, water-solubility, and neuroprotective effects of naringin by transglucosylation.
Debittering
Glucansucrase
Naringin glucoside
Neuroprotection
Transglucosylation
Water solubility
Journal
Applied microbiology and biotechnology
ISSN: 1432-0614
Titre abrégé: Appl Microbiol Biotechnol
Pays: Germany
ID NLM: 8406612
Informations de publication
Date de publication:
Oct 2023
Oct 2023
Historique:
received:
24
04
2023
accepted:
27
07
2023
revised:
22
07
2023
medline:
9
10
2023
pubmed:
29
8
2023
entrez:
29
8
2023
Statut:
ppublish
Résumé
Naringin found in citrus fruits is a flavanone glycoside with numerous biological activities. However, the bitterness, low water-solubility, and low bioavailability of naringin are the main issues limiting its use in the pharmaceutical and nutraceutical industries. Herein, a glucansucrase from isolated Leuconostoc citreum NY87 was used for trans-α-glucosylattion of naringin by using sucrose as substrate. Two naringin glucosides (O-α-D-glucosyl-(1'''' → 6″) naringin (compound 1) and 4'-O-α-D-glucosyl naringin (compound 2)) were purified and determined their structures by nuclear magnetic resonance. The optimization condition for the synthesis of compound 1 was obtained at 10 mM naringin, 200 mM sucrose, and 337.5 mU/mL at 28 °C for 24 h by response surface methodology method. Compound 1 and compound 2 showed 1896- and 3272 times higher water solubility than naringin. Furthermore, the bitterness via the human bitter taste receptor TAS2R39 displayed that compound 1 was reduced 2.9 times bitterness compared with naringin, while compound 2 did not express bitterness at 1 mM. Both compounds expressed higher neuroprotective effects than naringin on human neuroblastoma SH-SY5Y cells treated with 5 mM scopolamine based on cell viability and cortisol content. Compound 1 reduced acetylcholinesterase activity more than naringin and compound 2. These results indicate that naringin glucosides could be utilized as functional material in the nutraceutical and pharmaceutical industries. KEY POINTS: • A novel O-α-D-glucosyl-(1 → 6) naringin was synthesized using glucansucrase from L. citreum NY87. • Naringin glucosides improved water-solubility and neuroprotective effects on SH-SY5Y cells. • Naringin glucosides showed a decrease in bitterness on bitter taste receptor 39.
Identifiants
pubmed: 37642718
doi: 10.1007/s00253-023-12709-8
pii: 10.1007/s00253-023-12709-8
doi:
Substances chimiques
naringin
N7TD9J649B
Neuroprotective Agents
0
Acetylcholinesterase
EC 3.1.1.7
Flavanones
0
Sucrose
57-50-1
Glucosides
0
Water
059QF0KO0R
TAS2R39 protein, human
0
Receptors, Cell Surface
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
6205-6217Subventions
Organisme : Ministry of Education
ID : NRF-2020R1I1A1A01074322
Organisme : Rural Development Administration
ID : PJ016161
Informations de copyright
© 2023. The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature.
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