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Synthesis and Analytical Characterization of Purpurogallin: A Pharmacologically Active Constituent of Oak Galls
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SYSNO ASEP 0556924 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Synthesis and Analytical Characterization of Purpurogallin: A Pharmacologically Active Constituent of Oak Galls Author(s) Kelly-Hunt, A. E. (GB)
Mehan, A. (GB)
Brooks, S. (US)
Leanca, M. A. (GB)
McKay, J. E.D. (GB)
Mahamed, N. (GB)
Lambert, D. (FR)
Dempster, N. M. (GB)
Allen, R. J. (GB)
Evans, A. R. (GB)
Sarker, S. D. (GB)
Nahar, Lutfun (UEB-Q) ORCID
Sharples, G. P. (GB)
Drew, M. G. B. (GB)
Fielding, A. J. (GB)
Ismail, F. M.D. (GB)Number of authors 16 Source Title Journal of Chemical Education. - : American Chemical Society - ISSN 0021-9584
Roč. 99, č. 2 (2022), s. 983-993Number of pages 11 s. Language eng - English Country US - United States Keywords Graduate Education/Research ; Hands-On Learning/Manipulatives ; Natural Products ; NMR Spectroscopy ; Organic Chemistry ; Synthesis OECD category Organic chemistry Method of publishing Open access Institutional support UEB-Q - RVO:61389030 UT WOS 000734444800001 EID SCOPUS 85121926176 DOI 10.1021/acs.jchemed.1c00699 Annotation Purpurogallin (PPG), an orange-red crystalline compound from nutgalls and oak bark, is an exemplar of numerous, ubiquitous natural colorants, biosynthesized through oxidative dimerization-decarboxylation of phenolic compounds. It possesses antioxidant, anticancer, and anti-inflammatory effects. Herein, a robust method is presented to allow students to expediently make this interesting compound that contains a tropolone ring, whose identity initiated a paradigm shift in the understanding of aromaticity. 1D and 2D nuclear magnetic resonance (NMR) spectroscopic data (1H, 13C-DEPT-Q, HSQC, HMBC) were used to identify which protons are connected to carbon atoms. Fourier transform infrared spectroscopy (FT-IR), mass spectrometry, and X-ray diffraction were used to provide complementary information. Importantly, sufficient historical detail is given to provide a useful narrative that highlights the shift from deductive and synthetic proof of structural identity to modern methods of structural elucidation. As a minor, but important, aspect of iron gall inks, PPG links the work of important western historical documents from Da Vinci's Vitruvian Man to the United States Declaration of Independence. In the experience of the authors, such a pedagogic approach enlivens students with practical exercises which place them within the historical arc and reasoning of notable scientists, adding a sense of scientific discovery. Workplace Institute of Experimental Botany Contact David Klier, knihovna@ueb.cas.cz, Tel.: 220 390 469 Year of Publishing 2023 Electronic address http://doi.org/10.1021/acs.jchemed.1c00699
Number of the records: 1