29 No. 6
Natural Product Chemistry at a Glance
Stephen P. Staniforth, Blackwell Publishing, 2006 ISBN 1-4051-4562-5
reviewed by Mary Garson
Natural Product Chemistry at a Glance is a concise primer on natural products in which the author points out the striking mechanistic parallels between biosynthesis and many common organic reactions. This book is intended for senior undergraduates studying chemistry who have some familiarity with organic reactions and mechanistic concepts. The book may well suit the British and European markets, but it is unlikely to be suitable for the North American market where natural products is a topic covered at the graduate course level. In my experience, natural products is taught within a course on medicinal chemistry, something this textbook does not provide.
The book begins with a brief introduction to primary and secondary metabolites, and is then divided into six short sections that address the origin of fatty acids, polyketides, shikimate metabolites, terpenes, and alkaloids. (A final section provides answers to the mechanistic problems that are scattered throughout the text; the 141-page book also includes an index.)
Although the book jacket states that it “will serve as an initial platform for more advanced excursions” into natural products, the text does not capture the current “chemical biology” approach to natural products chemistry, nor does it put the numerous examples of natural product structures in an appropriate biological context—which would make it hard for a reader to use it as the basis for more advanced reading. The entire field of chemical ecology is covered in two brief paragraphs, and there is only occasional mention of the origin or medicinal effects of metabolites. A page of references provides some suggestions for additional reading, but the most recent reference is 2003, and those covering polyketides are from 1997—not recent enough given that this rapidly evolving research field is constantly updated through review literature.
Technically, the book is a useful catalog of natural products biosynthesis, however, it is too brief in some subject areas. The section on polyketide biosynthesis, for example, does not provide a good sense of the current state of this discipline. In relation to the important training example of 6-methylsalicylic acid, the biosynthesis is discussed starting from a tetraketide precursor, consequently the progressive mode of polyketide biosynthesis is not adequately explained. The brief section on labeling studies is not adequate either, since there were few accompanying diagrams that show individual labeling results. In fact, the reader is referred back to the earlier discussion on 6-methylsalicylic acid, but to an incorrect diagram. A mechanistic textbook also should discuss the chorismate to prephenate rearrangement, given its medicinal chemistry significance. In addition, the older term “pyrophosphate” is used in place of the more common term “diphosphate” in the section on terpene biosynthesis.
Finally, the graphics in a chemistry textbook are important, and I found a number of problems with the diagrams in this book. In some diagrams, for example, the biosynthetic origin of carbon atoms are identified using letters, which was visually distracting and contrary to the asterisks, squares, or other symbols used in most biosynthesis textbooks. Despite the condensed format, the text and diagrams were also repetitious in content. For example, Figures 2.12 and 3.8 use different abbreviations to represent the enzyme, “SCoA” and the “SEnz” descriptor, respectively, which is confusing for a student. In addition, some of the structures in the graphics are not aligned , such as the carbonyl groups in Figure 4.61.
Although the educational concepts behind this series of “at-a-glance” books are sound, I would not strongly recommend this textbook for students. It would, however, be a good reference guide.
Mary Garson <[email protected]> is a professor at the School of Molecular and Microbial Sciences at the University of Queensland, in Brisbane, Australia.
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