Human Saliva-Mediated Hydrolysis of Eugenyl-β-D-Glucoside and Fluorescein-di-β-D-Glucoside in In Vivo and In Vitro Models
Eugenyl-β-D-glucopyranoside, also referred to as Citrusin C, is a natural glucoside found among others in cloves, basil and cinnamon plants. Eugenol in a form of free aglycone is used in perfumeries, flavourings, essential oils and in medicinal products. Synthetic Citrusin C was incubated with human...
| Main Authors: | , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2021-01-01
|
| Series: | Biomolecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2218-273X/11/2/172 |
| _version_ | 1827597353182298112 |
|---|---|
| author | Mariusz Dziadas Adam Junka Henryk Jeleń |
| author_facet | Mariusz Dziadas Adam Junka Henryk Jeleń |
| author_sort | Mariusz Dziadas |
| collection | DOAJ |
| description | Eugenyl-β-D-glucopyranoside, also referred to as Citrusin C, is a natural glucoside found among others in cloves, basil and cinnamon plants. Eugenol in a form of free aglycone is used in perfumeries, flavourings, essential oils and in medicinal products. Synthetic Citrusin C was incubated with human saliva in several in vitro models together with substrate-specific enzyme and antibiotics (clindamycin, ciprofloxacin, amoxicillin trihydrate and potassium clavulanate). Citrusin C was detected using liquid chromatography with tandem mass spectrometry (LC-MS/MS). Citrusin C was completely degraded only when incubated with substrate-specific <i>A. niger</i> glucosidase E.C 3.2.1.21 (control sample) and when incubated with human saliva (tested sample). The addition of antibiotics to the above-described experimental setting, stopped Citrusin C degradation, indicating microbiologic origin of hydrolysis observed. Our results demonstrate that Citrusin C is subjected to complete degradation by salivary/oral cavity microorganisms. Extrapolation of our results allows to state that in the human oral cavity, virtually all β-D-glucosides would follow this type of hydrolysis. Additionally, a new method was developed for an in vivo rapid test of glucosidase activity in the human mouth on the tongue using fluorescein-di-β-D-glucoside as substrate. The results presented in this study serve as a proof of concept for the hypothesis that microbial hydrolysis path of β-D-glucosides begins immediately in the human mouth and releases the aglycone directly into the gastrointestinal tract. |
| first_indexed | 2024-03-09T03:29:06Z |
| format | Article |
| id | doaj.art-0a99ce79d6b44432b3a7c30b60392386 |
| institution | Directory Open Access Journal |
| issn | 2218-273X |
| language | English |
| last_indexed | 2024-03-09T03:29:06Z |
| publishDate | 2021-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Biomolecules |
| spelling | doaj.art-0a99ce79d6b44432b3a7c30b603923862023-12-03T14:57:56ZengMDPI AGBiomolecules2218-273X2021-01-0111217210.3390/biom11020172Human Saliva-Mediated Hydrolysis of Eugenyl-β-D-Glucoside and Fluorescein-di-β-D-Glucoside in In Vivo and In Vitro ModelsMariusz Dziadas0Adam Junka1Henryk Jeleń2Faculty of Chemistry, University of Wrocław, 50-383 Wrocław, PolandDepartment of Pharmaceutical Microbiology and Parasitology, Medical University of Wrocław, 50-556 Wrocław, PolandFaculty of Food Science and Nutrition, Poznan University of Life Science, 60-624 Poznań, PolandEugenyl-β-D-glucopyranoside, also referred to as Citrusin C, is a natural glucoside found among others in cloves, basil and cinnamon plants. Eugenol in a form of free aglycone is used in perfumeries, flavourings, essential oils and in medicinal products. Synthetic Citrusin C was incubated with human saliva in several in vitro models together with substrate-specific enzyme and antibiotics (clindamycin, ciprofloxacin, amoxicillin trihydrate and potassium clavulanate). Citrusin C was detected using liquid chromatography with tandem mass spectrometry (LC-MS/MS). Citrusin C was completely degraded only when incubated with substrate-specific <i>A. niger</i> glucosidase E.C 3.2.1.21 (control sample) and when incubated with human saliva (tested sample). The addition of antibiotics to the above-described experimental setting, stopped Citrusin C degradation, indicating microbiologic origin of hydrolysis observed. Our results demonstrate that Citrusin C is subjected to complete degradation by salivary/oral cavity microorganisms. Extrapolation of our results allows to state that in the human oral cavity, virtually all β-D-glucosides would follow this type of hydrolysis. Additionally, a new method was developed for an in vivo rapid test of glucosidase activity in the human mouth on the tongue using fluorescein-di-β-D-glucoside as substrate. The results presented in this study serve as a proof of concept for the hypothesis that microbial hydrolysis path of β-D-glucosides begins immediately in the human mouth and releases the aglycone directly into the gastrointestinal tract.https://www.mdpi.com/2218-273X/11/2/172β-glucosideshydrolysishuman saliva |
| spellingShingle | Mariusz Dziadas Adam Junka Henryk Jeleń Human Saliva-Mediated Hydrolysis of Eugenyl-β-D-Glucoside and Fluorescein-di-β-D-Glucoside in In Vivo and In Vitro Models Biomolecules β-glucosides hydrolysis human saliva |
| title | Human Saliva-Mediated Hydrolysis of Eugenyl-β-D-Glucoside and Fluorescein-di-β-D-Glucoside in In Vivo and In Vitro Models |
| title_full | Human Saliva-Mediated Hydrolysis of Eugenyl-β-D-Glucoside and Fluorescein-di-β-D-Glucoside in In Vivo and In Vitro Models |
| title_fullStr | Human Saliva-Mediated Hydrolysis of Eugenyl-β-D-Glucoside and Fluorescein-di-β-D-Glucoside in In Vivo and In Vitro Models |
| title_full_unstemmed | Human Saliva-Mediated Hydrolysis of Eugenyl-β-D-Glucoside and Fluorescein-di-β-D-Glucoside in In Vivo and In Vitro Models |
| title_short | Human Saliva-Mediated Hydrolysis of Eugenyl-β-D-Glucoside and Fluorescein-di-β-D-Glucoside in In Vivo and In Vitro Models |
| title_sort | human saliva mediated hydrolysis of eugenyl β d glucoside and fluorescein di β d glucoside in in vivo and in vitro models |
| topic | β-glucosides hydrolysis human saliva |
| url | https://www.mdpi.com/2218-273X/11/2/172 |
| work_keys_str_mv | AT mariuszdziadas humansalivamediatedhydrolysisofeugenylbdglucosideandfluoresceindibdglucosideininvivoandinvitromodels AT adamjunka humansalivamediatedhydrolysisofeugenylbdglucosideandfluoresceindibdglucosideininvivoandinvitromodels AT henrykjelen humansalivamediatedhydrolysisofeugenylbdglucosideandfluoresceindibdglucosideininvivoandinvitromodels |