{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,12]],"date-time":"2026-10-12T02:11:16Z","timestamp":1791771076689,"version":"4.3.4"},"reference-count":35,"publisher":"MDPI AG","issue":"14","license":[{"start":{"date-parts":[[2020,7,20]],"date-time":"2020-07-20T00:00:00Z","timestamp":1595203200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Natural products (NPs) constitute a significant source of active biomolecules widely used in medicine, pharmacology and cosmetics. However, NPs structural characterization has the drawback of their chemical instability during the extraction steps and their likely transformation during the analytical protocol. In particular, tamariscol and conocephalenol are two compounds largely used in the cosmetic industry for their odorant properties. Thus, in the present study, we focused on the evolution of these two metabolites (extracted from Frullania tamarisci and Conocephalum conicum, respectively), as followed by NMR. Interestingly, we found that, once dissolved in deuterated chloroform, these two tertiary alcohols are both subjected to transformation processes, leading to degradation compounds with altered structures. Accordingly, these detected degradation compounds have been fully characterized by NMR and the experimental findings were supported by computational chemistry data.<\/jats:p>","DOI":"10.3390\/molecules25143292","type":"journal-article","created":{"date-parts":[[2020,7,22]],"date-time":"2020-07-22T07:31:28Z","timestamp":1595403088000},"page":"3292","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Caution: Chemical Instability of Natural Biomolecules During Routine Analysis"],"prefix":"10.3390","volume":"25","author":[{"given":"Ana\u00efs","family":"Pannequin","sequence":"first","affiliation":[{"name":"UMR CNRS 6134 SPE, Laboratoire Chimie des Produits Naturels (CPN), Campus Grimaldi, Universit\u00e9 de Corse,  BP 52, 20250 Corte, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6092-6532","authenticated-orcid":false,"given":"Erik","family":"Laurini","sequence":"additional","affiliation":[{"name":"Molecular Biology and Nanotechnology Laboratory (MolBNL@UniTS), DEA, University of Trieste, 34127 Trieste, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Laurent","family":"Giordano","sequence":"additional","affiliation":[{"name":"Aix Marseille Univ, CNRS, Ecole Centrale de Marseille, Institut des Sciences Mol\u00e9culaires de Marseille UMR7313, 13397 Marseille, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alain","family":"Muselli","sequence":"additional","affiliation":[{"name":"UMR CNRS 6134 SPE, Laboratoire Chimie des Produits Naturels (CPN), Campus Grimaldi, Universit\u00e9 de Corse,  BP 52, 20250 Corte, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8380-4474","authenticated-orcid":false,"given":"Sabrina","family":"Pricl","sequence":"additional","affiliation":[{"name":"Molecular Biology and Nanotechnology Laboratory (MolBNL@UniTS), DEA, University of Trieste, 34127 Trieste, Italy"},{"name":"Department of General Biophysics, Faculty of Biology and Environmental Protection, University of Lodz, 90-236 Lodz, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8790-7753","authenticated-orcid":false,"given":"Aura","family":"Tintaru","sequence":"additional","affiliation":[{"name":"Aix Marseille Univ, CNRS, Institut de Chimie Radicalaire UMR7273, 13397 Marseille, France"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2020,7,20]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"497","DOI":"10.3184\/174751917X15021050367558","article-title":"Pseudo-Natural Products, Some Artefacts Formed during the Isolation of Terpenoids","volume":"41","author":"Hanson","year":"2017","journal-title":"J. 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