Synthesis of Proposed Structure of Aaptoline A, a Marine Sponge-Derived 7,8-Dihydroxyquinoline, and Its Neuroprotective Properties in <i>C. elegans</i>
A concise and efficient synthesis of the proposed structure of aaptoline A, a 7,8-dihydroxyquinoline derived from a marine sponge, was accomplished in seven steps with a 52% overall yield. A key feature of the synthesis is the high-yielding Ag(I)-catalyzed cycloisomerization of the <i>N</i&...
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| Format: | Article |
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MDPI AG
2021-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/19/5964 |
| _version_ | 1797515925599027200 |
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| author | Soobin Kim Wooin Yang Dong Seok Cha Young Taek Han |
| author_facet | Soobin Kim Wooin Yang Dong Seok Cha Young Taek Han |
| author_sort | Soobin Kim |
| collection | DOAJ |
| description | A concise and efficient synthesis of the proposed structure of aaptoline A, a 7,8-dihydroxyquinoline derived from a marine sponge, was accomplished in seven steps with a 52% overall yield. A key feature of the synthesis is the high-yielding Ag(I)-catalyzed cycloisomerization of the <i>N</i>-propargylaniline precursor to afford the quinoline carboxylate skeleton from acid-labile methyl aminobenzoate. However, the spectral data of the synthesized aaptoline A were not consistent with those of previous studies. The structure of the synthesized aaptoline A was confirmed by combined 2D NMR analysis. Additional studies on the bioactivity of the synthesized aaptoline A revealed that it has the ability to protect dopaminergic neurons against MPP<sup>+</sup>-induced neurotoxicity in <i>C. elegans</i>. In addition, impaired food-sensing ability and travel distance capability in <i>C. elegans</i> were significantly ameliorated by aaptoline A treatment, suggesting that aaptoline A can protect dopaminergic neurons both morphologically and functionally. |
| first_indexed | 2024-03-10T06:54:07Z |
| format | Article |
| id | doaj.art-7aad5fbf67884d9185b6781e1e6423aa |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T06:54:07Z |
| publishDate | 2021-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-7aad5fbf67884d9185b6781e1e6423aa2023-11-22T16:35:17ZengMDPI AGMolecules1420-30492021-10-012619596410.3390/molecules26195964Synthesis of Proposed Structure of Aaptoline A, a Marine Sponge-Derived 7,8-Dihydroxyquinoline, and Its Neuroprotective Properties in <i>C. elegans</i>Soobin Kim0Wooin Yang1Dong Seok Cha2Young Taek Han3College of Pharmacy, Dankook University, Cheonan 31116, Chungnam, KoreaCollege of Pharmacy, Woosuk University, Wanju-gun 55338, Jeonbuk, KoreaCollege of Pharmacy, Woosuk University, Wanju-gun 55338, Jeonbuk, KoreaCollege of Pharmacy, Dankook University, Cheonan 31116, Chungnam, KoreaA concise and efficient synthesis of the proposed structure of aaptoline A, a 7,8-dihydroxyquinoline derived from a marine sponge, was accomplished in seven steps with a 52% overall yield. A key feature of the synthesis is the high-yielding Ag(I)-catalyzed cycloisomerization of the <i>N</i>-propargylaniline precursor to afford the quinoline carboxylate skeleton from acid-labile methyl aminobenzoate. However, the spectral data of the synthesized aaptoline A were not consistent with those of previous studies. The structure of the synthesized aaptoline A was confirmed by combined 2D NMR analysis. Additional studies on the bioactivity of the synthesized aaptoline A revealed that it has the ability to protect dopaminergic neurons against MPP<sup>+</sup>-induced neurotoxicity in <i>C. elegans</i>. In addition, impaired food-sensing ability and travel distance capability in <i>C. elegans</i> were significantly ameliorated by aaptoline A treatment, suggesting that aaptoline A can protect dopaminergic neurons both morphologically and functionally.https://www.mdpi.com/1420-3049/26/19/5964aaptoline A7,8-dihydroxyquinolinesilver-catalyzed cycloisomerizationdopaminergic neuroprotectionParkinson’s disease |
| spellingShingle | Soobin Kim Wooin Yang Dong Seok Cha Young Taek Han Synthesis of Proposed Structure of Aaptoline A, a Marine Sponge-Derived 7,8-Dihydroxyquinoline, and Its Neuroprotective Properties in <i>C. elegans</i> Molecules aaptoline A 7,8-dihydroxyquinoline silver-catalyzed cycloisomerization dopaminergic neuroprotection Parkinson’s disease |
| title | Synthesis of Proposed Structure of Aaptoline A, a Marine Sponge-Derived 7,8-Dihydroxyquinoline, and Its Neuroprotective Properties in <i>C. elegans</i> |
| title_full | Synthesis of Proposed Structure of Aaptoline A, a Marine Sponge-Derived 7,8-Dihydroxyquinoline, and Its Neuroprotective Properties in <i>C. elegans</i> |
| title_fullStr | Synthesis of Proposed Structure of Aaptoline A, a Marine Sponge-Derived 7,8-Dihydroxyquinoline, and Its Neuroprotective Properties in <i>C. elegans</i> |
| title_full_unstemmed | Synthesis of Proposed Structure of Aaptoline A, a Marine Sponge-Derived 7,8-Dihydroxyquinoline, and Its Neuroprotective Properties in <i>C. elegans</i> |
| title_short | Synthesis of Proposed Structure of Aaptoline A, a Marine Sponge-Derived 7,8-Dihydroxyquinoline, and Its Neuroprotective Properties in <i>C. elegans</i> |
| title_sort | synthesis of proposed structure of aaptoline a a marine sponge derived 7 8 dihydroxyquinoline and its neuroprotective properties in i c elegans i |
| topic | aaptoline A 7,8-dihydroxyquinoline silver-catalyzed cycloisomerization dopaminergic neuroprotection Parkinson’s disease |
| url | https://www.mdpi.com/1420-3049/26/19/5964 |
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