Bioassay-Guided Isolation, Metabolic Profiling, and Docking Studies of Hyaluronidase Inhibitors from <i>Ravenala madagascariensis</i>
Hyaluronidase enzyme (HAase) has a role in the dissolution or disintegration of hyaluronic acid (HA) and in maintaining the heathy state of skin. Bioassay-guided fractionation of <i>Ravenala madagascariensis</i> (Sonn.) organ extracts (leaf, flower, stem, and root) testing for hyaluronid...
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MDPI AG
2020-04-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/7/1714 |
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| author | Esraa M. Mohamed Mona H. Hetta Mostafa E. Rateb Mohamed A. Selim Asmaa M. AboulMagd Farid A. Badria Usama Ramadan Abdelmohsen Hani A. Alhadrami Hossam M. Hassan |
| author_facet | Esraa M. Mohamed Mona H. Hetta Mostafa E. Rateb Mohamed A. Selim Asmaa M. AboulMagd Farid A. Badria Usama Ramadan Abdelmohsen Hani A. Alhadrami Hossam M. Hassan |
| author_sort | Esraa M. Mohamed |
| collection | DOAJ |
| description | Hyaluronidase enzyme (HAase) has a role in the dissolution or disintegration of hyaluronic acid (HA) and in maintaining the heathy state of skin. Bioassay-guided fractionation of <i>Ravenala madagascariensis</i> (Sonn.) organ extracts (leaf, flower, stem, and root) testing for hyaluronidase inhibition was performed followed by metabolic profiling using LC–HRMS. Additionally, a hyaluronidase docking study was achieved using Molecular Operating Environment (MOE). Results showed that the crude hydroalcoholic (70% EtOH) extract of the leaves as well as its <i>n</i>-butanol (<i>n</i>-BuOH) partition showed higher HAase activity with 64.3% inhibition. Metabolic analysis of <i>R. madagascariensis</i> resulted in the identification of 19 phenolic compounds ranging from different chemical classes (flavone glycosides, flavonol glycosides, and flavanol aglycones). Bioassay-guided purification of the leaf <i>n</i>-BuOH partition led to the isolation of seven compounds that were identified as narcissin, rutin, epiafzelechin, epicatechin, isorhamnetin 7-<i>O</i>-glucoside, kaempferol, and isorhamnetin-7-<i>O</i>-rutinoside. The docking study showed that narcissin, rutin, and quercetin 3-<i>O</i>-glucoside all interact with HAase through hydrogen bonding with the Asp111, Gln271, and/or Glu113 residues. Our results highlight <i>Ravenala madagascariensis</i> and its flavonoids as promising hyaluronidase inhibitors in natural cosmetology preparations for skin care. |
| first_indexed | 2024-03-10T20:35:46Z |
| format | Article |
| id | doaj.art-5a14397f79074c1982da19b43570be1d |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T20:35:46Z |
| publishDate | 2020-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-5a14397f79074c1982da19b43570be1d2023-11-19T21:03:13ZengMDPI AGMolecules1420-30492020-04-01257171410.3390/molecules25071714Bioassay-Guided Isolation, Metabolic Profiling, and Docking Studies of Hyaluronidase Inhibitors from <i>Ravenala madagascariensis</i>Esraa M. Mohamed0Mona H. Hetta1Mostafa E. Rateb2Mohamed A. Selim3Asmaa M. AboulMagd4Farid A. Badria5Usama Ramadan Abdelmohsen6Hani A. Alhadrami7Hossam M. Hassan8Department of Pharmacognosy, Faculty of Pharmacy, MUST, Giza 12566, EgyptDepartment of Pharmacognosy, Faculty of Pharmacy, Fayoum University, Fayoum 63514, EgyptDepartment of Pharmacognosy, Faculty of Pharmacy, Beni-Suef University, Beni-Suef 62514, EgyptDepartment of Pharmacognosy, Faculty of Pharmacy, MUST, Giza 12566, EgyptDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Nahda University, Beni-Suef 62511, EgyptDepartment of Pharmacognosy, Faculty of Pharmacy, Mansoura University, Mansoura 35516, EgyptDepartment of Pharmacognosy, Faculty of Pharmacy, Minia University, Minia 61519, EgyptFaculty of Applied Medical Sciences, Department of Medical Laboratory Technology, King Abdulaziz University, P.O. Box 80402, Jeddah 21589, Saudi ArabiaDepartment of Pharmacognosy, Faculty of Pharmacy, Beni-Suef University, Beni-Suef 62514, EgyptHyaluronidase enzyme (HAase) has a role in the dissolution or disintegration of hyaluronic acid (HA) and in maintaining the heathy state of skin. Bioassay-guided fractionation of <i>Ravenala madagascariensis</i> (Sonn.) organ extracts (leaf, flower, stem, and root) testing for hyaluronidase inhibition was performed followed by metabolic profiling using LC–HRMS. Additionally, a hyaluronidase docking study was achieved using Molecular Operating Environment (MOE). Results showed that the crude hydroalcoholic (70% EtOH) extract of the leaves as well as its <i>n</i>-butanol (<i>n</i>-BuOH) partition showed higher HAase activity with 64.3% inhibition. Metabolic analysis of <i>R. madagascariensis</i> resulted in the identification of 19 phenolic compounds ranging from different chemical classes (flavone glycosides, flavonol glycosides, and flavanol aglycones). Bioassay-guided purification of the leaf <i>n</i>-BuOH partition led to the isolation of seven compounds that were identified as narcissin, rutin, epiafzelechin, epicatechin, isorhamnetin 7-<i>O</i>-glucoside, kaempferol, and isorhamnetin-7-<i>O</i>-rutinoside. The docking study showed that narcissin, rutin, and quercetin 3-<i>O</i>-glucoside all interact with HAase through hydrogen bonding with the Asp111, Gln271, and/or Glu113 residues. Our results highlight <i>Ravenala madagascariensis</i> and its flavonoids as promising hyaluronidase inhibitors in natural cosmetology preparations for skin care.https://www.mdpi.com/1420-3049/25/7/1714hyaluronidase inhibitors<i>Ravenala madagascariensis</i>metabolomicsdocking |
| spellingShingle | Esraa M. Mohamed Mona H. Hetta Mostafa E. Rateb Mohamed A. Selim Asmaa M. AboulMagd Farid A. Badria Usama Ramadan Abdelmohsen Hani A. Alhadrami Hossam M. Hassan Bioassay-Guided Isolation, Metabolic Profiling, and Docking Studies of Hyaluronidase Inhibitors from <i>Ravenala madagascariensis</i> Molecules hyaluronidase inhibitors <i>Ravenala madagascariensis</i> metabolomics docking |
| title | Bioassay-Guided Isolation, Metabolic Profiling, and Docking Studies of Hyaluronidase Inhibitors from <i>Ravenala madagascariensis</i> |
| title_full | Bioassay-Guided Isolation, Metabolic Profiling, and Docking Studies of Hyaluronidase Inhibitors from <i>Ravenala madagascariensis</i> |
| title_fullStr | Bioassay-Guided Isolation, Metabolic Profiling, and Docking Studies of Hyaluronidase Inhibitors from <i>Ravenala madagascariensis</i> |
| title_full_unstemmed | Bioassay-Guided Isolation, Metabolic Profiling, and Docking Studies of Hyaluronidase Inhibitors from <i>Ravenala madagascariensis</i> |
| title_short | Bioassay-Guided Isolation, Metabolic Profiling, and Docking Studies of Hyaluronidase Inhibitors from <i>Ravenala madagascariensis</i> |
| title_sort | bioassay guided isolation metabolic profiling and docking studies of hyaluronidase inhibitors from i ravenala madagascariensis i |
| topic | hyaluronidase inhibitors <i>Ravenala madagascariensis</i> metabolomics docking |
| url | https://www.mdpi.com/1420-3049/25/7/1714 |
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