Xylochemical Synthesis and Biological Evaluation of Shancigusin C and Bletistrin G
The biological activities of shancigusin C (<b>1</b>) and bletistrin G (<b>2</b>), natural products isolated from orchids, are reported along with their first total syntheses. The total synthesis of shancigusin C (<b>1</b>) was conducted by employing the Perkin re...
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| Format: | Article |
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MDPI AG
2021-05-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/11/3224 |
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| author | Leander Geske Ulrich Kauhl Mohamed E. M. Saeed Anja Schüffler Eckhard Thines Thomas Efferth Till Opatz |
| author_facet | Leander Geske Ulrich Kauhl Mohamed E. M. Saeed Anja Schüffler Eckhard Thines Thomas Efferth Till Opatz |
| author_sort | Leander Geske |
| collection | DOAJ |
| description | The biological activities of shancigusin C (<b>1</b>) and bletistrin G (<b>2</b>), natural products isolated from orchids, are reported along with their first total syntheses. The total synthesis of shancigusin C (<b>1</b>) was conducted by employing the Perkin reaction to forge the central stilbene core, whereas the synthesis of bletistrin G (<b>2</b>) was achieved by the Wittig olefination followed by several regioselective aromatic substitution reactions. Both syntheses were completed by applying only renewable starting materials according to the principles of xylochemistry. The cytotoxic properties of shancigusin C (<b>1</b>) and bletistrin G (<b>2</b>) against tumor cells suggest suitability as a starting point for further structural variation. |
| first_indexed | 2024-03-10T10:59:01Z |
| format | Article |
| id | doaj.art-ee3cff6e205f45be9168ced622b4541f |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T10:59:01Z |
| publishDate | 2021-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-ee3cff6e205f45be9168ced622b4541f2023-11-21T21:41:15ZengMDPI AGMolecules1420-30492021-05-012611322410.3390/molecules26113224Xylochemical Synthesis and Biological Evaluation of Shancigusin C and Bletistrin GLeander Geske0Ulrich Kauhl1Mohamed E. M. Saeed2Anja Schüffler3Eckhard Thines4Thomas Efferth5Till Opatz6Department of Chemistry, Organic Chemistry Section, Johannes Gutenberg University, Duesbergweg 10-14, 55128 Mainz, GermanyDepartment of Chemistry, Organic Chemistry Section, Johannes Gutenberg University, Duesbergweg 10-14, 55128 Mainz, GermanyInstitute of Pharmaceutical and Biomedical Sciences, Johannes Gutenberg University, Staudingerweg 5, 55128 Mainz, GermanyInstitut für Biotechnologie und Wirkstoff-Forschung gGmbH, Hanns-Dieter-Hüsch-Weg 17, 55128 Mainz, GermanyInstitut für Biotechnologie und Wirkstoff-Forschung gGmbH, Hanns-Dieter-Hüsch-Weg 17, 55128 Mainz, GermanyInstitute of Pharmaceutical and Biomedical Sciences, Johannes Gutenberg University, Staudingerweg 5, 55128 Mainz, GermanyDepartment of Chemistry, Organic Chemistry Section, Johannes Gutenberg University, Duesbergweg 10-14, 55128 Mainz, GermanyThe biological activities of shancigusin C (<b>1</b>) and bletistrin G (<b>2</b>), natural products isolated from orchids, are reported along with their first total syntheses. The total synthesis of shancigusin C (<b>1</b>) was conducted by employing the Perkin reaction to forge the central stilbene core, whereas the synthesis of bletistrin G (<b>2</b>) was achieved by the Wittig olefination followed by several regioselective aromatic substitution reactions. Both syntheses were completed by applying only renewable starting materials according to the principles of xylochemistry. The cytotoxic properties of shancigusin C (<b>1</b>) and bletistrin G (<b>2</b>) against tumor cells suggest suitability as a starting point for further structural variation.https://www.mdpi.com/1420-3049/26/11/3224shancigusin Cbletistrin Gtotal synthesisbiological activitynatural products |
| spellingShingle | Leander Geske Ulrich Kauhl Mohamed E. M. Saeed Anja Schüffler Eckhard Thines Thomas Efferth Till Opatz Xylochemical Synthesis and Biological Evaluation of Shancigusin C and Bletistrin G Molecules shancigusin C bletistrin G total synthesis biological activity natural products |
| title | Xylochemical Synthesis and Biological Evaluation of Shancigusin C and Bletistrin G |
| title_full | Xylochemical Synthesis and Biological Evaluation of Shancigusin C and Bletistrin G |
| title_fullStr | Xylochemical Synthesis and Biological Evaluation of Shancigusin C and Bletistrin G |
| title_full_unstemmed | Xylochemical Synthesis and Biological Evaluation of Shancigusin C and Bletistrin G |
| title_short | Xylochemical Synthesis and Biological Evaluation of Shancigusin C and Bletistrin G |
| title_sort | xylochemical synthesis and biological evaluation of shancigusin c and bletistrin g |
| topic | shancigusin C bletistrin G total synthesis biological activity natural products |
| url | https://www.mdpi.com/1420-3049/26/11/3224 |
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