Novel Dihydrocoumarins Induced by Radiolysis as Potent Tyrosinase Inhibitors
A representative naturally occurring coumarin, 4-methylumbelliferone (<b>5</b>), was exposed to 50 kGy of gamma ray, resulting in four newly generated dihydrocoumarin products <b>1</b>–<b>4</b> induced by the gamma irradiation. The structures of these new products...
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MDPI AG
2024-01-01
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| Online Access: | https://www.mdpi.com/1420-3049/29/2/341 |
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| author | Gyeong Han Jeong Manisha Yadav Seung Sik Lee Byung Yeoup Chung Jae-Hyeon Cho In-Chul Lee Hyoung-Woo Bai Tae Hoon Kim |
| author_facet | Gyeong Han Jeong Manisha Yadav Seung Sik Lee Byung Yeoup Chung Jae-Hyeon Cho In-Chul Lee Hyoung-Woo Bai Tae Hoon Kim |
| author_sort | Gyeong Han Jeong |
| collection | DOAJ |
| description | A representative naturally occurring coumarin, 4-methylumbelliferone (<b>5</b>), was exposed to 50 kGy of gamma ray, resulting in four newly generated dihydrocoumarin products <b>1</b>–<b>4</b> induced by the gamma irradiation. The structures of these new products were elucidated by interpretation of spectroscopic data (NMR, MS, [α]<sub>D</sub>, and UV). The unusual bisdihydrocoumarin <b>4</b> exhibited improved tyrosinase inhibitory capacity toward mushroom tyrosinase with IC<sub>50</sub> values of 19.8 ± 0.5 μM as compared to the original 4-methylumbelliferone (<b>5</b>). A kinetic analysis also exhibited that the potent metabolite <b>4</b> had non-competitive modes of action. Linkage of the hydroxymethyl group in the C-3 and C-4 positions on the lactone ring probably enhances the tyrosinase inhibitory effect of 4-methylumbelliferone (<b>5</b>). Thus, the novel coumarin analog <b>4</b> is an interesting new class of tyrosinase inhibitory candidates that requires further examination. |
| first_indexed | 2024-03-08T09:50:01Z |
| format | Article |
| id | doaj.art-a740922ce43646e7be1f1e9c3ac51531 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-08T09:50:01Z |
| publishDate | 2024-01-01 |
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| series | Molecules |
| spelling | doaj.art-a740922ce43646e7be1f1e9c3ac515312024-01-29T14:07:41ZengMDPI AGMolecules1420-30492024-01-0129234110.3390/molecules29020341Novel Dihydrocoumarins Induced by Radiolysis as Potent Tyrosinase InhibitorsGyeong Han Jeong0Manisha Yadav1Seung Sik Lee2Byung Yeoup Chung3Jae-Hyeon Cho4In-Chul Lee5Hyoung-Woo Bai6Tae Hoon Kim7Research Division for Biotechnology, Advanced Radiation Technology Institute (ARTI), Korea Atomic Energy Research Institute (KAERI), Jeongeup 56212, Republic of KoreaDepartment of Food Science and Biotechnology, Daegu University, Gyeongsan 38453, Republic of KoreaResearch Division for Biotechnology, Advanced Radiation Technology Institute (ARTI), Korea Atomic Energy Research Institute (KAERI), Jeongeup 56212, Republic of KoreaResearch Division for Biotechnology, Advanced Radiation Technology Institute (ARTI), Korea Atomic Energy Research Institute (KAERI), Jeongeup 56212, Republic of KoreaInstitute of Animal Medicine, College of Veterinary Medicine, Gyeongsang National University, Jinju 52828, Republic of KoreaDepartment of Cosmetic Science and Technology, Seowon University, Cheongju 28674, Republic of KoreaResearch Division for Biotechnology, Advanced Radiation Technology Institute (ARTI), Korea Atomic Energy Research Institute (KAERI), Jeongeup 56212, Republic of KoreaDepartment of Food Science and Biotechnology, Daegu University, Gyeongsan 38453, Republic of KoreaA representative naturally occurring coumarin, 4-methylumbelliferone (<b>5</b>), was exposed to 50 kGy of gamma ray, resulting in four newly generated dihydrocoumarin products <b>1</b>–<b>4</b> induced by the gamma irradiation. The structures of these new products were elucidated by interpretation of spectroscopic data (NMR, MS, [α]<sub>D</sub>, and UV). The unusual bisdihydrocoumarin <b>4</b> exhibited improved tyrosinase inhibitory capacity toward mushroom tyrosinase with IC<sub>50</sub> values of 19.8 ± 0.5 μM as compared to the original 4-methylumbelliferone (<b>5</b>). A kinetic analysis also exhibited that the potent metabolite <b>4</b> had non-competitive modes of action. Linkage of the hydroxymethyl group in the C-3 and C-4 positions on the lactone ring probably enhances the tyrosinase inhibitory effect of 4-methylumbelliferone (<b>5</b>). Thus, the novel coumarin analog <b>4</b> is an interesting new class of tyrosinase inhibitory candidates that requires further examination.https://www.mdpi.com/1420-3049/29/2/3414-methylumbelliferonegamma irradiationtyrosinase inhibitionhydrogenationhydroxymethylation |
| spellingShingle | Gyeong Han Jeong Manisha Yadav Seung Sik Lee Byung Yeoup Chung Jae-Hyeon Cho In-Chul Lee Hyoung-Woo Bai Tae Hoon Kim Novel Dihydrocoumarins Induced by Radiolysis as Potent Tyrosinase Inhibitors Molecules 4-methylumbelliferone gamma irradiation tyrosinase inhibition hydrogenation hydroxymethylation |
| title | Novel Dihydrocoumarins Induced by Radiolysis as Potent Tyrosinase Inhibitors |
| title_full | Novel Dihydrocoumarins Induced by Radiolysis as Potent Tyrosinase Inhibitors |
| title_fullStr | Novel Dihydrocoumarins Induced by Radiolysis as Potent Tyrosinase Inhibitors |
| title_full_unstemmed | Novel Dihydrocoumarins Induced by Radiolysis as Potent Tyrosinase Inhibitors |
| title_short | Novel Dihydrocoumarins Induced by Radiolysis as Potent Tyrosinase Inhibitors |
| title_sort | novel dihydrocoumarins induced by radiolysis as potent tyrosinase inhibitors |
| topic | 4-methylumbelliferone gamma irradiation tyrosinase inhibition hydrogenation hydroxymethylation |
| url | https://www.mdpi.com/1420-3049/29/2/341 |
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