دورية أكاديمية
Resolving a Natural Product Cold Case: Elucidation of Fusapyrone Structure and Absolute Configuration and Demonstration of Their Fungal Biofilm Disrupting Properties.
| العنوان: | Resolving a Natural Product Cold Case: Elucidation of Fusapyrone Structure and Absolute Configuration and Demonstration of Their Fungal Biofilm Disrupting Properties. |
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| المؤلفون: | Kil YS; Natural Products Discovery Group, Institute for Natural Products Applications and Research Technologies, Department of Chemistry & Biochemistry, Stephenson Life Science Research Center, University of Oklahoma, Norman, Oklahoma 73019, United States., You J; Natural Products Discovery Group, Institute for Natural Products Applications and Research Technologies, Department of Chemistry & Biochemistry, Stephenson Life Science Research Center, University of Oklahoma, Norman, Oklahoma 73019, United States., Wendt KL; Natural Products Discovery Group, Institute for Natural Products Applications and Research Technologies, Department of Chemistry & Biochemistry, Stephenson Life Science Research Center, University of Oklahoma, Norman, Oklahoma 73019, United States., King JB; Natural Products Discovery Group, Institute for Natural Products Applications and Research Technologies, Department of Chemistry & Biochemistry, Stephenson Life Science Research Center, University of Oklahoma, Norman, Oklahoma 73019, United States., Cichewicz RH; Natural Products Discovery Group, Institute for Natural Products Applications and Research Technologies, Department of Chemistry & Biochemistry, Stephenson Life Science Research Center, University of Oklahoma, Norman, Oklahoma 73019, United States. |
| المصدر: | The Journal of organic chemistry [J Org Chem] 2023 Jul 07; Vol. 88 (13), pp. 9167-9186. Date of Electronic Publication: 2023 Jun 21. |
| نوع المنشور: | Journal Article |
| اللغة: | English |
| بيانات الدورية: | Publisher: American Chemical Society Country of Publication: United States NLM ID: 2985193R Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1520-6904 (Electronic) Linking ISSN: 00223263 NLM ISO Abbreviation: J Org Chem Subsets: MEDLINE |
| أسماء مطبوعة: | Publication: Columbus Oh : American Chemical Society Original Publication: Easton, Pa. [etc.] |
| مواضيع طبية MeSH: | Candida albicans* , Antifungal Agents*/pharmacology , Antifungal Agents*/chemistry, Humans ; Pyrones/pharmacology ; Biofilms |
| مستخلص: | Fusapyrones are fungal metabolites, which have been reported to have broad-spectrum antibacterial and antifungal properties. Despite the first members of this chemical class being described three decades prior, many aspects of their structures have remained unresolved, thereby constraining efforts to fully understand structure-activity relationships within this metabolite family and impeding the design of streamlined syntheses. Among the main challenges posed by fusapyrones is the incorporation of several single and groups of stereocenters separated by atoms with freely rotating bonds, which have proven unyielding to spectroscopic analyses. In this study, we obtained a series of new ( 2 - 5 and 7 - 9 ) and previously reported fusapyrones ( 1 and 6 ), which were subjected to a combination of spectroscopic, chemical, and computational techniques enabling us to offer proposals for their full structures, as well as provide a pathway to reinterpreting the absolute configurations of other published fusapyrone metabolites. Biological testing of the fusapyrones revealed their abilities to inhibit and disrupt biofilms made by the human fungal pathogen, Candida albicans . These results show that fusapyrones reduce hyphae formation in C. albicans , as well as decrease the surface adherence capabilities of planktonic cells and cells transitioning into early-stage biofilm formation. |
| المشرفين على المادة: | 156856-31-4 (fusapyrone) 0 (Antifungal Agents) 0 (Pyrones) |
| تواريخ الأحداث: | Date Created: 20230621 Date Completed: 20230710 Latest Revision: 20231221 |
| رمز التحديث: | 20231221 |
| DOI: | 10.1021/acs.joc.3c00765 |
| PMID: | 37343240 |
| قاعدة البيانات: | MEDLINE |
Find this issue from the American Chemical Society | تدمد: | 1520-6904 |
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| DOI: | 10.1021/acs.joc.3c00765 |