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Trends in Organic Chemistry   Volumes    Volume 22 
Abstract
Prioritizing natural product compounds using 1D-TOCSY NMR spectroscopy
Cassandra Diaz-Allen, Richard W. Spjut, A. Douglas Kinghorn, Harinantenaina L. Rakotondraibe
Pages: 99 - 114
Number of pages: 16
Trends in Organic Chemistry
Volume 22 

Copyright © 2021 Research Trends. All rights reserved

ABSTRACT
 
Natural product (NP) secondary metabolites are designed evolutionarily to have biological effects in other organisms for defense and the mediation of ecological interactions. Their structural complexity and diversity complement biological systems, allowing them to display unique bioactivities. Although more than half of all pharmaceuticals stem from NPs, pharmaceutical companies have reduced NP-based drug discovery programs due to various time and cost-consuming pitfalls; the re-isolation of already known, bioactive compounds being one of the most common. Dereplication methods minimize cost and speed up the discovery of new, bioactive leads by quickly identifying known small molecules. Liquid chromatography coupled mass spectrometry (LC-MS) is the most widely utilized dereplication technique because of its sensitivity and the open-source availability of MS libraries. However, single-ionization techniques are not able to detect all metabolites in a biological sample. Even more concerning, bioactive isomers cannot be differentiated by their mass alone. In response to these issues, complementary dereplication tools are needed to assist MS. Total correlation spectroscopy (TOCSY) is an NMR experiment that illustrates the connection between all coupled protons in a spin system. Most molecules contain several spin systems, and together, these networks form a unique fingerprint that can be utilized to quickly differentiate and dereplicate known compounds, even those with identical masses. In addition, these fingerprints can be used to identify possible new compounds in a crude NP-extract that are structurally related to known small molecules. From a sample of the U.S. endemic lichen Niebla homalea, five non-cytotoxic, new triterpenoids and three known triterpenoids were isolated in our laboratory. As our goal is to discover both new and cytotoxic compounds, we developed a one-dimensional TOCSY-based dereplication method to quickly identify these non-bioactive triterpenoids. After prioritizing triterpenoid-free fractions that showed antiproliferative activity in various cancer cell lines, the new compound 11 was isolated from another Niebla species.
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