Anti-inflammatory Activities and Gastric Ulcer-inducing Properties of Tetraacetylquercetin and Tetrapivaloylquercetin
Quercetin (3,3’4’,5,7-pentahydroxyflavone) has been reported to show anti-inflammatory activity. However, its low oral bioavailability limits the application of quercetin in therapy. Ester derivatives of quercetin have been reported to have higher bioavailability than quercetin. This research aimed...
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| Format: | Article |
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ITB Journal Publisher
2016-12-01
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| Series: | Journal of Mathematical and Fundamental Sciences |
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| Online Access: | http://journals.itb.ac.id/index.php/jmfs/article/view/548 |
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| author | Rina Herowati Rahmana Emran Kartasasmita I Ketut Adnyana Tutus Gusdinar Kartawinata |
| author_facet | Rina Herowati Rahmana Emran Kartasasmita I Ketut Adnyana Tutus Gusdinar Kartawinata |
| author_sort | Rina Herowati |
| collection | DOAJ |
| description | Quercetin (3,3’4’,5,7-pentahydroxyflavone) has been reported to show anti-inflammatory activity. However, its low oral bioavailability limits the application of quercetin in therapy. Ester derivatives of quercetin have been reported to have higher bioavailability than quercetin. This research aimed to study the anti-inflammatory activities and gastric ulcer-inducing properties of tetraacetylquercetinas well as tetrapivaloylquercetin. Synthesis of tetra-acyl derivatives of quercetin was conducted using acetic anhydride or pivaloyl chloride in the presence of pyridine and the structure was confirmed by 1H-NMR and 13C-NMR spectroscopy as well as elemental analysis. At a dose of 20 mg/kg bw, oral administration of quercetin only showed 20% inhibition activity on carragenan induced rat paw edema, while tetraacetyl and tetrapivaloyl derivatives at equimolar dose showed 11-33% and 5-15% inhibition activity respectively. Contrary to the gastric ulcer healing-promoting action of quercetin, tetraacetylquercetin caused mild gastric ulcers. However, no gastric ulcer was observed after administration of tetrapivaloylquercetin. It was concluded that acylation enhances the anti-inflammatory activity of quercetin but causes mild gastric ulcers in the case of tetraacetylation. |
| first_indexed | 2024-12-14T10:50:14Z |
| format | Article |
| id | doaj.art-4d5b089fd3e549809528dfea5c4500c8 |
| institution | Directory Open Access Journal |
| issn | 2337-5760 2338-5510 |
| language | English |
| last_indexed | 2024-12-14T10:50:14Z |
| publishDate | 2016-12-01 |
| publisher | ITB Journal Publisher |
| record_format | Article |
| series | Journal of Mathematical and Fundamental Sciences |
| spelling | doaj.art-4d5b089fd3e549809528dfea5c4500c82022-12-21T23:05:16ZengITB Journal PublisherJournal of Mathematical and Fundamental Sciences2337-57602338-55102016-12-0148325226210.5614/j.math.fund.sci.2016.48.3.6Anti-inflammatory Activities and Gastric Ulcer-inducing Properties of Tetraacetylquercetin and TetrapivaloylquercetinRina Herowati0Rahmana Emran Kartasasmita1I Ketut Adnyana2Tutus Gusdinar Kartawinata3Faculty of Pharmacy, Universitas Setia Budi, Jl.Letjen Sutoyo, Surakarta, IndonesiaSchool of Pharmacy, Institut Teknologi Bandung, Jl. Ganesa 10, IndonesiaSchool of Pharmacy, Institut Teknologi Bandung, Jl. Ganesa 10, IndonesiaSchool of Pharmacy, Institut Teknologi Bandung, Jl. Ganesa 10, IndonesiaQuercetin (3,3’4’,5,7-pentahydroxyflavone) has been reported to show anti-inflammatory activity. However, its low oral bioavailability limits the application of quercetin in therapy. Ester derivatives of quercetin have been reported to have higher bioavailability than quercetin. This research aimed to study the anti-inflammatory activities and gastric ulcer-inducing properties of tetraacetylquercetinas well as tetrapivaloylquercetin. Synthesis of tetra-acyl derivatives of quercetin was conducted using acetic anhydride or pivaloyl chloride in the presence of pyridine and the structure was confirmed by 1H-NMR and 13C-NMR spectroscopy as well as elemental analysis. At a dose of 20 mg/kg bw, oral administration of quercetin only showed 20% inhibition activity on carragenan induced rat paw edema, while tetraacetyl and tetrapivaloyl derivatives at equimolar dose showed 11-33% and 5-15% inhibition activity respectively. Contrary to the gastric ulcer healing-promoting action of quercetin, tetraacetylquercetin caused mild gastric ulcers. However, no gastric ulcer was observed after administration of tetrapivaloylquercetin. It was concluded that acylation enhances the anti-inflammatory activity of quercetin but causes mild gastric ulcers in the case of tetraacetylation.http://journals.itb.ac.id/index.php/jmfs/article/view/548anti-inflammatory activitygastric ulcer-inducing propertytetraacetylquercetintetrapivaloylquercetinquercetin |
| spellingShingle | Rina Herowati Rahmana Emran Kartasasmita I Ketut Adnyana Tutus Gusdinar Kartawinata Anti-inflammatory Activities and Gastric Ulcer-inducing Properties of Tetraacetylquercetin and Tetrapivaloylquercetin Journal of Mathematical and Fundamental Sciences anti-inflammatory activity gastric ulcer-inducing property tetraacetylquercetin tetrapivaloylquercetin quercetin |
| title | Anti-inflammatory Activities and Gastric Ulcer-inducing Properties of Tetraacetylquercetin and Tetrapivaloylquercetin |
| title_full | Anti-inflammatory Activities and Gastric Ulcer-inducing Properties of Tetraacetylquercetin and Tetrapivaloylquercetin |
| title_fullStr | Anti-inflammatory Activities and Gastric Ulcer-inducing Properties of Tetraacetylquercetin and Tetrapivaloylquercetin |
| title_full_unstemmed | Anti-inflammatory Activities and Gastric Ulcer-inducing Properties of Tetraacetylquercetin and Tetrapivaloylquercetin |
| title_short | Anti-inflammatory Activities and Gastric Ulcer-inducing Properties of Tetraacetylquercetin and Tetrapivaloylquercetin |
| title_sort | anti inflammatory activities and gastric ulcer inducing properties of tetraacetylquercetin and tetrapivaloylquercetin |
| topic | anti-inflammatory activity gastric ulcer-inducing property tetraacetylquercetin tetrapivaloylquercetin quercetin |
| url | http://journals.itb.ac.id/index.php/jmfs/article/view/548 |
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