Book Review Cite This: J. Nat. Prod. 2018, 81, 1692−1692
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Review of Chemistry of Organic Natural Products. Volume 100 natural product structure elucidation starting with a discussion on NMR-based dereplication techniques, followed by determination of the absolute concentration of compounds by quantitative NMR techniques. The next section discusses the application of various 2D NMR techniques for determination of skeletal structure and step-by-step guidelines for avoiding incorrect skeletal assignments, followed by determination of the configuration/conformation of natural products using homo- (1H−1H) and heteronuclear (1H−13C) coupling constants and NOEs. Two sections are dedicated to examples of structures solved via traditional step-by-step strategy or computer-assisted structural elucidation. The rest of this chapter covers experimental aspects ranging from probe choice to detailed discussion of various acquisition and processing parameters of 1D and 2D NMR. Overall, this chapter is a must-read for anyone in the field of natural product structure elucidation. The fourth chapter, entitled “Vibrational circular dichroism absolute configuration determination of natural products”, is the longest chapter of this book and starts with an introduction followed by the history of stereochemical characterization of organic molecules based on VCD calculations. The theoretical and experimental aspects are summarized in the next two sections. The fifth section is the longest and perhaps the most impactful section of this book. It constitutes an extended body of information on the stereochemical study of natural products using the VCD technique. Several examples of chirality determination or confirmation of terpenes, diterpenes, meroterpenoids, triterpenes, aromatic molecules, and other classes of compounds are discussed in detail. The illustrations and figures in this chapter are clear and displayed in color when needed. The purchase price for this book is relatively high ($349.99 for the hardcover, 299.99 for the softcover, and $229.00 for the eBook). Considering the differences in the quality and content of each chapter of this book, the best purchase option is the electronic version of each individual chapter, which is priced $29.95 on the publisher’s Web site.
Chemistry of Organic Natural Products. Volume 100. Edited by Douglas A. Kinghorn, Heinz Falk, and Jun’ichi Kobayashi. Springer. 2015. 588 pp. $349.99. ISBN 978-3-319-05275-5.
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his volume of Progress in the Chemistry of Organic Natural Products provides an overview of modern analytical methods currently used for structure elucidation of organic natural products. The book is organized into five chapters. Each chapter discusses the application of a specific analytical technique for characterization of organic natural products except the fifth chapter, which reviews Volumes 1 to 99 of the Progress in the Chemistry of Organic Natural Products series itself. The first chapter, entitled “Structure elucidation of natural compounds by X-ray crystallography”, starts with a brief introduction and history, followed by a section on the theoretical basis of X-ray crystallography. The theoretical discussion starts with the Bragg equation and continues with an overview of scattering theory. The fourth section of this chapter covers the general steps involved in the process of structure elucidation, including crystallography from crystallization to interpretation of data. The latter section, which constitutes more than half of the chapter, is perhaps the most useful for the average natural product chemist not specialized in the field of crystallography. The chapter continues with a brief overview of various crystallographic databases and ends with a short section on special techniques. Overall, the illustrations and graphs in this chapter are very informative and of high quality and clarity. The figures are original (not reproduced) and mostly in color. “Mass spectroscopy in natural product structure elucidation” is the title of the second chapter, which starts with a brief introduction followed by a very short description of various ionization and ion separation techniques. Analysis of mixtures, which is essential to natural product drug discovery research, is discussed in less than two pages. Additionally, the usefulness of this chapter to natural product chemists is compromised by the lack of any discussion of dereplication. The rest of the chapter covers numerous examples, organized based on the class/ source of natural product compounds, including saturated triterpenes, alkaloids from vertebrates, fatty acids and lipids, carbohydrates, peptides, proteins, nucleosides, nucleotides, and nucleic acids. The chapter is continued with a list of mass spectrometric databases and ends with an addendum section. Almost all figures and illustrations in this chapter are in black and white. The size and style of chemical structures, in general, are not consistent. Some figures are lower resolution black and white illustrations with inconsistent formatting (e.g., Figures 113, 118, 122). The third chapter is entitled “Nuclear magnetic resonance in the structure elucidation of natural products” and is the shortest and perhaps most well-written and edited chapter of this book. Emphasis is placed on the practical aspects of modern NMR methods used for natural product structure elucidation. This chapter covers the critical steps involved in © 2018 American Chemical Society and American Society of Pharmacognosy
Mohamad Nazari
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Oregon State University, Corvallis, Oregon, United States
AUTHOR INFORMATION
Notes
The author declares no competing financial interest.
Published: July 5, 2018 1692
DOI: 10.1021/acs.jnatprod.8b00488 J. Nat. Prod. 2018, 81, 1692−1692
