Ultra-Performance Liquid Chromatography Coupled with Mass Metabolic Profiling of <i>Ammi majus</i> Roots as Waste Product with Isolation and Assessment of Oral Mucosal Toxicity of Its Psoralen Component Xanthotoxin
<i>Ammi majus</i>, a well-established member of the Umbelliferae (Apiaceae) family, is endogenous to Egypt. The main parts of this plant that are used are the fruits, which contain coumarins and flavonoids as major active constituents. The roots are usually considered by-products that ar...
| Main Authors: | , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2023-09-01
|
| Series: | Metabolites |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2218-1989/13/10/1044 |
| _version_ | 1797573062881705984 |
|---|---|
| author | Noha Fathallah Mona El Deeb Amany A. Rabea Alshaimaa M. Almehmady Hanaa Alkharobi Sameh S. Elhady Noha Khalil |
| author_facet | Noha Fathallah Mona El Deeb Amany A. Rabea Alshaimaa M. Almehmady Hanaa Alkharobi Sameh S. Elhady Noha Khalil |
| author_sort | Noha Fathallah |
| collection | DOAJ |
| description | <i>Ammi majus</i>, a well-established member of the Umbelliferae (Apiaceae) family, is endogenous to Egypt. The main parts of this plant that are used are the fruits, which contain coumarins and flavonoids as major active constituents. The roots are usually considered by-products that are discarded and not fed to cattle because of coumarins’ potential toxicity. The goal of this study was to ensure the sustainability of the plant, investigate the active metabolites present in the roots using UPLC/MS-MS, isolate and elucidate the major coumarin Xanthotoxin, and predict its oral bioavailability and its potential biological impact on tongue papillae. The results revealed coumarins as the dominant chemical class in a positive acquisition mode, with bergaptol-<i>O</i>-hexoside 5%, Xanthotoxin 5.5%, and isoarnoittinin 6% being the major compounds. However, phenolics ruled in the negative mode, with <i>p</i>-coumaroyl tartaric acid 7%, 3,7-dimethyl quercetin 6%, and hesperidin 5% being the most prominent metabolites. Fractionation and purification of the chloroform fraction yielded Xanthotoxin as one of the main compounds, which appeared as white needle crystals (20 mg). ADME studies for oral bioavailability were performed to predict the potential properties of the compound if used orally. It was noted that it followed Lipinski’s rule of five, had just one parameter outside of the pink area in the radar plot, and was detected inside the threshold area using the boiled egg approach. In vivo, histopathological studies performed on rats showed a notable decrease in the tongue’s keratin thickness from an average of 51.1 µm to 9.1 µm and an average of 51.8 µm to 9.8 µm in fungiform and filiform cells, respectively. The results indicated that although Xanthotoxin is a well-known medical agent with several potential therapeutic activities in oral therapy, it may cause a destructive effect on the structure of the specialized mucosa of the tongue. |
| first_indexed | 2024-03-10T21:04:20Z |
| format | Article |
| id | doaj.art-f0c4572cce004cf0b8de01476e32b408 |
| institution | Directory Open Access Journal |
| issn | 2218-1989 |
| language | English |
| last_indexed | 2024-03-10T21:04:20Z |
| publishDate | 2023-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Metabolites |
| spelling | doaj.art-f0c4572cce004cf0b8de01476e32b4082023-11-19T17:19:39ZengMDPI AGMetabolites2218-19892023-09-011310104410.3390/metabo13101044Ultra-Performance Liquid Chromatography Coupled with Mass Metabolic Profiling of <i>Ammi majus</i> Roots as Waste Product with Isolation and Assessment of Oral Mucosal Toxicity of Its Psoralen Component XanthotoxinNoha Fathallah0Mona El Deeb1Amany A. Rabea2Alshaimaa M. Almehmady3Hanaa Alkharobi4Sameh S. Elhady5Noha Khalil6Department of Pharmacognosy and Medicinal Plants, Faculty of Pharmacy, Future University in Egypt, Cairo 11835, EgyptDepartment of Oral Biology, Faculty of Oral and Dental Medicine, Future University in Egypt, Cairo 11835, EgyptDepartment of Oral Biology, Faculty of Oral and Dental Medicine, Future University in Egypt, Cairo 11835, EgyptDepartment of Pharmaceutics, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Saudi ArabiaDepartment of Oral Biology, Faculty of Dentistry, King Abdulaziz University, Jeddah 21589, Saudi ArabiaDepartment of Natural Products, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Saudi ArabiaDepartment of Pharmacognosy and Medicinal Plants, Faculty of Pharmacy, Future University in Egypt, Cairo 11835, Egypt<i>Ammi majus</i>, a well-established member of the Umbelliferae (Apiaceae) family, is endogenous to Egypt. The main parts of this plant that are used are the fruits, which contain coumarins and flavonoids as major active constituents. The roots are usually considered by-products that are discarded and not fed to cattle because of coumarins’ potential toxicity. The goal of this study was to ensure the sustainability of the plant, investigate the active metabolites present in the roots using UPLC/MS-MS, isolate and elucidate the major coumarin Xanthotoxin, and predict its oral bioavailability and its potential biological impact on tongue papillae. The results revealed coumarins as the dominant chemical class in a positive acquisition mode, with bergaptol-<i>O</i>-hexoside 5%, Xanthotoxin 5.5%, and isoarnoittinin 6% being the major compounds. However, phenolics ruled in the negative mode, with <i>p</i>-coumaroyl tartaric acid 7%, 3,7-dimethyl quercetin 6%, and hesperidin 5% being the most prominent metabolites. Fractionation and purification of the chloroform fraction yielded Xanthotoxin as one of the main compounds, which appeared as white needle crystals (20 mg). ADME studies for oral bioavailability were performed to predict the potential properties of the compound if used orally. It was noted that it followed Lipinski’s rule of five, had just one parameter outside of the pink area in the radar plot, and was detected inside the threshold area using the boiled egg approach. In vivo, histopathological studies performed on rats showed a notable decrease in the tongue’s keratin thickness from an average of 51.1 µm to 9.1 µm and an average of 51.8 µm to 9.8 µm in fungiform and filiform cells, respectively. The results indicated that although Xanthotoxin is a well-known medical agent with several potential therapeutic activities in oral therapy, it may cause a destructive effect on the structure of the specialized mucosa of the tongue.https://www.mdpi.com/2218-1989/13/10/1044<i>Ammi majus</i> rootsApiaceaemetabolitesADMEboiled egghistopathological studies |
| spellingShingle | Noha Fathallah Mona El Deeb Amany A. Rabea Alshaimaa M. Almehmady Hanaa Alkharobi Sameh S. Elhady Noha Khalil Ultra-Performance Liquid Chromatography Coupled with Mass Metabolic Profiling of <i>Ammi majus</i> Roots as Waste Product with Isolation and Assessment of Oral Mucosal Toxicity of Its Psoralen Component Xanthotoxin Metabolites <i>Ammi majus</i> roots Apiaceae metabolites ADME boiled egg histopathological studies |
| title | Ultra-Performance Liquid Chromatography Coupled with Mass Metabolic Profiling of <i>Ammi majus</i> Roots as Waste Product with Isolation and Assessment of Oral Mucosal Toxicity of Its Psoralen Component Xanthotoxin |
| title_full | Ultra-Performance Liquid Chromatography Coupled with Mass Metabolic Profiling of <i>Ammi majus</i> Roots as Waste Product with Isolation and Assessment of Oral Mucosal Toxicity of Its Psoralen Component Xanthotoxin |
| title_fullStr | Ultra-Performance Liquid Chromatography Coupled with Mass Metabolic Profiling of <i>Ammi majus</i> Roots as Waste Product with Isolation and Assessment of Oral Mucosal Toxicity of Its Psoralen Component Xanthotoxin |
| title_full_unstemmed | Ultra-Performance Liquid Chromatography Coupled with Mass Metabolic Profiling of <i>Ammi majus</i> Roots as Waste Product with Isolation and Assessment of Oral Mucosal Toxicity of Its Psoralen Component Xanthotoxin |
| title_short | Ultra-Performance Liquid Chromatography Coupled with Mass Metabolic Profiling of <i>Ammi majus</i> Roots as Waste Product with Isolation and Assessment of Oral Mucosal Toxicity of Its Psoralen Component Xanthotoxin |
| title_sort | ultra performance liquid chromatography coupled with mass metabolic profiling of i ammi majus i roots as waste product with isolation and assessment of oral mucosal toxicity of its psoralen component xanthotoxin |
| topic | <i>Ammi majus</i> roots Apiaceae metabolites ADME boiled egg histopathological studies |
| url | https://www.mdpi.com/2218-1989/13/10/1044 |
| work_keys_str_mv | AT nohafathallah ultraperformanceliquidchromatographycoupledwithmassmetabolicprofilingofiammimajusirootsaswasteproductwithisolationandassessmentoforalmucosaltoxicityofitspsoralencomponentxanthotoxin AT monaeldeeb ultraperformanceliquidchromatographycoupledwithmassmetabolicprofilingofiammimajusirootsaswasteproductwithisolationandassessmentoforalmucosaltoxicityofitspsoralencomponentxanthotoxin AT amanyarabea ultraperformanceliquidchromatographycoupledwithmassmetabolicprofilingofiammimajusirootsaswasteproductwithisolationandassessmentoforalmucosaltoxicityofitspsoralencomponentxanthotoxin AT alshaimaamalmehmady ultraperformanceliquidchromatographycoupledwithmassmetabolicprofilingofiammimajusirootsaswasteproductwithisolationandassessmentoforalmucosaltoxicityofitspsoralencomponentxanthotoxin AT hanaaalkharobi ultraperformanceliquidchromatographycoupledwithmassmetabolicprofilingofiammimajusirootsaswasteproductwithisolationandassessmentoforalmucosaltoxicityofitspsoralencomponentxanthotoxin AT samehselhady ultraperformanceliquidchromatographycoupledwithmassmetabolicprofilingofiammimajusirootsaswasteproductwithisolationandassessmentoforalmucosaltoxicityofitspsoralencomponentxanthotoxin AT nohakhalil ultraperformanceliquidchromatographycoupledwithmassmetabolicprofilingofiammimajusirootsaswasteproductwithisolationandassessmentoforalmucosaltoxicityofitspsoralencomponentxanthotoxin |