Issue 9, 2022
From the journal:

Natural Product Reports

Pitfalls in the structural elucidation of small molecules. A critical analysis of a decade of structural misassignments of marine natural products†‡

Shou-Mao Shen, ORCID logo ab   Giovanni Appendino ORCID logo c  and  Yue-Wei Guo ORCID logo *ad  

* Corresponding authors

a State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China
E-mail: ywguo@simm.ac.cn

b School of Chinese Materia Medica, Nanjing University of Chinese Medicine, Nanjing 210023, China

c Dipartimento di Scienze del Farmaco, Universitá degli Studi del Piemonte Orientale, Largo Donegani 2, 28100 Novara, Italy

d Drug Discovery Shandong Laboratory, Bohai Rim Advanced Research Institute for Drug Discovery, Yantai, Shandong 264117, China

Abstract

Covering: July 2010 to August 2021

This article summarizes more than 200 cases of misassigned marine natural products reported between July 2010 and August 2021, sorting out errors according to the structural elements. Based on a comparative analysis of the original and the revised structures, major pitfalls still plaguing the structural elucidation of small molecules were identified, emphasizing the role of total synthesis, crystallography, as well as chemical- and biosynthetic logic to complement spectroscopic data. Distinct “trends” in natural product misassignment are evident between compounds of marine and plant origin, with an overall much lower incidence of “impossible” structures within misassigned marine natural products.

Graphical abstract: Pitfalls in the structural elucidation of small molecules. A critical analysis of a decade of structural misassignments of marine natural products

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Article information

DOI
https://doi.org/10.1039/D2NP00023G
Article type
Review Article
Submitted
28 Mar 2022
First published
30 Jun 2022

Nat. Prod. Rep., 2022,39, 1803-1832

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Pitfalls in the structural elucidation of small molecules. A critical analysis of a decade of structural misassignments of marine natural products

S. Shen, G. Appendino and Y. Guo, Nat. Prod. Rep., 2022, 39, 1803 DOI: 10.1039/D2NP00023G

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