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注意:在常规分析过程中天然生物分子的化学不稳定性。

Caution: Chemical Instability of Natural Biomolecules During Routine Analysis.

机构信息

UMR CNRS 6134 SPE, Laboratoire Chimie des Produits Naturels (CPN), Campus Grimaldi, Université de Corse, BP 52, 20250 Corte, France.

Molecular Biology and Nanotechnology Laboratory (MolBNL@UniTS), DEA, University of Trieste, 34127 Trieste, Italy.

出版信息

Molecules. 2020 Jul 20;25(14):3292. doi: 10.3390/molecules25143292.

DOI:10.3390/molecules25143292
PMID:32698478
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7397321/
Abstract

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 and 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.

摘要

天然产物(NPs)是生物活性分子的重要来源,广泛应用于医学、药理学和化妆品领域。然而,NPs 的结构特征分析存在提取步骤中化学不稳定性的缺点,并且在分析方案中可能发生转化。特别是,tamariscol 和 conocephalenol 是两种化合物,由于其具有气味特性,在化妆品行业中大量使用。因此,在本研究中,我们重点关注这两种代谢物(分别从 和 中提取)通过 NMR 检测到的变化。有趣的是,我们发现,这两种叔醇一旦溶解在氘代氯仿中,都会发生转化过程,导致结构发生变化的降解化合物。因此,通过 NMR 对这些检测到的降解化合物进行了充分的表征,并通过计算化学数据支持了实验结果。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9059/7397321/2933b3760811/molecules-25-03292-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9059/7397321/0944fe33e9ce/molecules-25-03292-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9059/7397321/92da3d6d6960/molecules-25-03292-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9059/7397321/1f6218d559f6/molecules-25-03292-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9059/7397321/d489a656e230/molecules-25-03292-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9059/7397321/6abf587de728/molecules-25-03292-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9059/7397321/7bd12b3d1ab9/molecules-25-03292-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9059/7397321/2933b3760811/molecules-25-03292-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9059/7397321/0944fe33e9ce/molecules-25-03292-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9059/7397321/92da3d6d6960/molecules-25-03292-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9059/7397321/1f6218d559f6/molecules-25-03292-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9059/7397321/d489a656e230/molecules-25-03292-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9059/7397321/6abf587de728/molecules-25-03292-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9059/7397321/7bd12b3d1ab9/molecules-25-03292-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9059/7397321/2933b3760811/molecules-25-03292-sch004.jpg

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