Microbial Transformation of the Sesquiterpene Lactone, Vulgarin, by <i>Aspergillus niger</i>
The biotransformation of vulgarin <b>(1)</b>, an eudesmanolides-type sesquiterpene lactone obtained from <i>Artemisia judaica</i>, by the microorganism, <i>Aspergillus niger</i>, was carried out to give three more polar metabolites; 1-<i>epi</i>-tetrah...
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MDPI AG
2023-04-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/9/3729 |
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| author | Reem A. ElGamal Amal A. Galala Maged S. Abdel-Kader Farid A. Badria Amal F. Soliman |
| author_facet | Reem A. ElGamal Amal A. Galala Maged S. Abdel-Kader Farid A. Badria Amal F. Soliman |
| author_sort | Reem A. ElGamal |
| collection | DOAJ |
| description | The biotransformation of vulgarin <b>(1)</b>, an eudesmanolides-type sesquiterpene lactone obtained from <i>Artemisia judaica</i>, by the microorganism, <i>Aspergillus niger</i>, was carried out to give three more polar metabolites; 1-<i>epi</i>-tetrahydrovulgarin (1α,4α-dihydroxy-5αH,6,11βH-eudesman-6,12-olide <b>(2)</b>, 20% yield, 1α,4α-dihydroxyeudesm-2-en-5αH,6,11βH-6,12-olide <b>(3a)</b>, 10% yield, and C-1 epimeric mixture <b>(3a, b)</b>, 4% yield, in a ratio of 4:1, <b>3a/3b</b>. The structures of vulgarin and its metabolites were elucidated by 1 and 2D NMR spectroscopy in conjunction with HRESIMS. Metabolites <b>(3a)</b> and <b>(3b)</b> are epimers, and they are reported here for the first time as new metabolites obtained by biotransformation by selective reduction at C-1. Vulgarin and its metabolites were evaluated as anti-inflammatory agents using the human cyclooxygenase (COX) inhibitory assay. The obtained data showed that <b>(1)</b> exhibited a good preferential inhibitory activity towards COX-2 (IC50 = 07.21 ± 0.10) and had a moderate effect on COX-1 (IC50 = 11.32 ± 0.24). Meanwhile, its metabolite <b>(3a)</b> retained a selective inhibitory activity against COX-1 (IC50 = 15.70 ± 0.51). In conclusion, the results of this study revealed the necessity of the presence α, β unsaturated carbonyl group in <b>(1)</b> for better COX-2 inhibitory activity. On the other hand, the selectivity of <b>(1)</b> as COX-1 inhibitor may be enhanced via the reduction of C-1 carbonyl group. |
| first_indexed | 2024-03-11T04:12:36Z |
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| id | doaj.art-df99b1927d7c4602bdfa48de3974be81 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T04:12:36Z |
| publishDate | 2023-04-01 |
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| spelling | doaj.art-df99b1927d7c4602bdfa48de3974be812023-11-17T23:22:39ZengMDPI AGMolecules1420-30492023-04-01289372910.3390/molecules28093729Microbial Transformation of the Sesquiterpene Lactone, Vulgarin, by <i>Aspergillus niger</i>Reem A. ElGamal0Amal A. Galala1Maged S. Abdel-Kader2Farid A. Badria3Amal F. Soliman4Pharmacognosy Department, Faculty of Pharmacy, Mansoura University, El Mansoura 35516, EgyptPharmacognosy Department, Faculty of Pharmacy, Mansoura University, El Mansoura 35516, EgyptDepartment of Pharmacognosy, College of Pharmacy, Prince Sattam Bin Abdulaziz University, Al-Kharj 11942, Saudi ArabiaPharmacognosy Department, Faculty of Pharmacy, Mansoura University, El Mansoura 35516, EgyptPharmacognosy Department, Faculty of Pharmacy, Mansoura University, El Mansoura 35516, EgyptThe biotransformation of vulgarin <b>(1)</b>, an eudesmanolides-type sesquiterpene lactone obtained from <i>Artemisia judaica</i>, by the microorganism, <i>Aspergillus niger</i>, was carried out to give three more polar metabolites; 1-<i>epi</i>-tetrahydrovulgarin (1α,4α-dihydroxy-5αH,6,11βH-eudesman-6,12-olide <b>(2)</b>, 20% yield, 1α,4α-dihydroxyeudesm-2-en-5αH,6,11βH-6,12-olide <b>(3a)</b>, 10% yield, and C-1 epimeric mixture <b>(3a, b)</b>, 4% yield, in a ratio of 4:1, <b>3a/3b</b>. The structures of vulgarin and its metabolites were elucidated by 1 and 2D NMR spectroscopy in conjunction with HRESIMS. Metabolites <b>(3a)</b> and <b>(3b)</b> are epimers, and they are reported here for the first time as new metabolites obtained by biotransformation by selective reduction at C-1. Vulgarin and its metabolites were evaluated as anti-inflammatory agents using the human cyclooxygenase (COX) inhibitory assay. The obtained data showed that <b>(1)</b> exhibited a good preferential inhibitory activity towards COX-2 (IC50 = 07.21 ± 0.10) and had a moderate effect on COX-1 (IC50 = 11.32 ± 0.24). Meanwhile, its metabolite <b>(3a)</b> retained a selective inhibitory activity against COX-1 (IC50 = 15.70 ± 0.51). In conclusion, the results of this study revealed the necessity of the presence α, β unsaturated carbonyl group in <b>(1)</b> for better COX-2 inhibitory activity. On the other hand, the selectivity of <b>(1)</b> as COX-1 inhibitor may be enhanced via the reduction of C-1 carbonyl group.https://www.mdpi.com/1420-3049/28/9/3729vulgarinbiotransformation<i>Aspergillus niger</i>vulgarin metabolitesCOX inhibitors |
| spellingShingle | Reem A. ElGamal Amal A. Galala Maged S. Abdel-Kader Farid A. Badria Amal F. Soliman Microbial Transformation of the Sesquiterpene Lactone, Vulgarin, by <i>Aspergillus niger</i> Molecules vulgarin biotransformation <i>Aspergillus niger</i> vulgarin metabolites COX inhibitors |
| title | Microbial Transformation of the Sesquiterpene Lactone, Vulgarin, by <i>Aspergillus niger</i> |
| title_full | Microbial Transformation of the Sesquiterpene Lactone, Vulgarin, by <i>Aspergillus niger</i> |
| title_fullStr | Microbial Transformation of the Sesquiterpene Lactone, Vulgarin, by <i>Aspergillus niger</i> |
| title_full_unstemmed | Microbial Transformation of the Sesquiterpene Lactone, Vulgarin, by <i>Aspergillus niger</i> |
| title_short | Microbial Transformation of the Sesquiterpene Lactone, Vulgarin, by <i>Aspergillus niger</i> |
| title_sort | microbial transformation of the sesquiterpene lactone vulgarin by i aspergillus niger i |
| topic | vulgarin biotransformation <i>Aspergillus niger</i> vulgarin metabolites COX inhibitors |
| url | https://www.mdpi.com/1420-3049/28/9/3729 |
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