classics in spectroscopy: isolation and structure elucidation of natural products. by stefan berger...

2
Classics in Spectroscopy: Isolation and Structure Elucidation of Natural Products By Stefan Berger and Dieter Sicker. Wiley-VCH, Weinheim 2009, XIV + 645 pp., softcover E 79.00.—ISBN 978-3-527-32516-0 Natural product chemistry is a key area of organic chemistry, and the one on which, historically, the whole discipline is founded. While many books are published on nat- ural products in general or on their synthesis and aspects thereof, only a few deal with their isola- tion and characterization by spectro- scopic methods. Therefore, this 600-page book is a welcome addition, filling a gap in the monograph literature. The book is the fifth title in the highly acclaimed series Classics in… published by Wiley-VCH. Readers who know the other titles may be surprised, because the rationale behind this book is com- pletely different from that of the other titles. Here 30 procedures for the isola- tion and thorough characterization of well-known natural products are present- ed. The compounds discussed range from nicotine, strychnine, eugenol, cap- santhin, lactose, cnicin etc. to aleuritic acid, covering all major classes of natural products. Most of the compounds (28) can be isolated from plants and seem to have been selected in part because of the availability of the starting material. The book is based on a laboratory course in natural product isolation at the University of Leipzig, Germany. Every compound is presented in a chapter that follows a unique style not commonly found in science books. It begins with an essay on that particular compound, discussing aspects of the cul- tural history and natural history of the compound and its source, written in quite a personal style. There is usually a short discussion of the biosynthesis, but the focus lies on the properties and his- tory. Every chapter is amply illustrated with many photographs, albeit one could say that this is overdone. For ex- ample, four photos of simple coffee beans, four of bell peppers or of other rather simple products from everyday life are not really necessary and only in- crease the volume of the book without benefit. Another interesting idea is the use of the margin for short textual ex- cerpts from authors ranging from an- cient Greeks and Julius Caesar up to modern authors, including trivia. These texts are presented in the original lan- guage, and a translation into English can be found in an appendix. This arrange- ment leads to problems with the legibili- ty of the book. The main part of the text goes in very close to the central bound edge. Thus, when reading the book, you have to move it a little every time you come to a line end; this becomes cum- bersome when you are reading for longer periods. Next, a short list of references is given. An optimized isolation procedure is then presented in detail. The different ap- proaches used for the individual compo- nents give a nice broad overview of the methodologies used for the isolation of natural products. The most impressive part of the book comes next, the presen- tation of full UV, IR, CD, NMR, and mass spectra of the isolated compounds. The focus lies on the NMR spectra, which are presented as a full set including 1 H, 13 C, COSY, HSQC, NOESY, and HMBC spectra. These spectra are discussed in detail, giving wonderful material for courses on NMR spectroscopy, and may even have some surprises for readers who know NMR spectroscopy very well. The mass spectra are also discussed, but the pro- posed fragmentations seem sometimes questionable to an experienced reader, and the arrows in the figures are not always correctly positioned. Clearer dif- ferentiation between proposed and proven pathways would be helpful. The structures of the compounds are repeat- ed on each double page, which makes working with the spectra very easy. A three-dimensional structure is given for every compound, but any explanation as how a given structure was produced (X- ray analysis, simple or advanced molecu- lar modeling) is missing. A set of ques- tions closes each chapter, with answers in the appendix, followed by a free half page for your own observations. The production of the book is not up to the usual high Wiley-VCH standard. While the presentation is nice—every- thing is clearly printed, and color is used in an advantageous way—the English text is rather bumpy. Furthermore, many typing errors occur, also sometimes in the spectral discussions. A bit more at- tention to the language would have helped the book in every respect. Last but not least, who will read this book? It is not clear to me why this nice book is a member of the Classics in… family. The title is misleading, because the other books in this series point out those scientific hallmarks of their disci- pline that are still valid today. After read- ing the title, I expected a book discus- sing the most important and cutting- edge spectroscopic methods, exempli- fied on the most difficult problems in the structure elucidation of natural prod- ucts, historically and recently. In fact, this book is a laboratory and spectroscopic course with added interesting general in- formation. In essence, Classics in Spec- troscopy is a valuable addition to any university library and fills a gap not cov- Natural Classics 2800 www.chembiochem.org # 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim ChemBioChem 2009, 10, 2800 – 2803

Upload: stefan-schulz

Post on 06-Jun-2016

218 views

Category:

Documents


1 download

TRANSCRIPT

Page 1: Classics in Spectroscopy: Isolation and Structure Elucidation of Natural Products. By Stefan Berger and Dieter Sicker

Classics in Spectroscopy:Isolation and StructureElucidation of NaturalProductsBy Stefan Berger and Dieter Sicker.

Wiley-VCH, Weinheim 2009, XIV + 645 pp. ,softcover E 79.00.—ISBN 978-3-527-32516-0

Natural productchemistry is a keyarea of organicchemistry, and theone on which,historically, thewhole discipline isfounded. Whilemany books arepublished on nat-ural products ingeneral or on their synthesis and aspectsthereof, only a few deal with their isola-tion and characterization by spectro-scopic methods. Therefore, this 600-pagebook is a welcome addition, filling a gapin the monograph literature.

The book is the fifth title in the highlyacclaimed series Classics in… publishedby Wiley-VCH. Readers who know theother titles may be surprised, becausethe rationale behind this book is com-pletely different from that of the othertitles. Here 30 procedures for the isola-tion and thorough characterization ofwell-known natural products are present-ed. The compounds discussed rangefrom nicotine, strychnine, eugenol, cap-santhin, lactose, cnicin etc. to aleuriticacid, covering all major classes of naturalproducts. Most of the compounds (28)can be isolated from plants and seem tohave been selected in part because ofthe availability of the starting material.The book is based on a laboratorycourse in natural product isolation at theUniversity of Leipzig, Germany.

Every compound is presented in achapter that follows a unique style not

commonly found in science books. Itbegins with an essay on that particularcompound, discussing aspects of the cul-tural history and natural history of thecompound and its source, written inquite a personal style. There is usually ashort discussion of the biosynthesis, butthe focus lies on the properties and his-tory. Every chapter is amply illustratedwith many photographs, albeit onecould say that this is overdone. For ex-ample, four photos of simple coffeebeans, four of bell peppers or of otherrather simple products from everydaylife are not really necessary and only in-crease the volume of the book withoutbenefit. Another interesting idea is theuse of the margin for short textual ex-cerpts from authors ranging from an-cient Greeks and Julius Caesar up tomodern authors, including trivia. Thesetexts are presented in the original lan-guage, and a translation into English canbe found in an appendix. This arrange-ment leads to problems with the legibili-ty of the book. The main part of the textgoes in very close to the central boundedge. Thus, when reading the book, youhave to move it a little every time youcome to a line end; this becomes cum-bersome when you are reading forlonger periods.

Next, a short list of references is given.An optimized isolation procedure is thenpresented in detail. The different ap-proaches used for the individual compo-nents give a nice broad overview of themethodologies used for the isolation ofnatural products. The most impressivepart of the book comes next, the presen-tation of full UV, IR, CD, NMR, and massspectra of the isolated compounds. Thefocus lies on the NMR spectra, which arepresented as a full set including 1H, 13C,COSY, HSQC, NOESY, and HMBC spectra.These spectra are discussed in detail,giving wonderful material for courses onNMR spectroscopy, and may even have

some surprises for readers who knowNMR spectroscopy very well. The massspectra are also discussed, but the pro-posed fragmentations seem sometimesquestionable to an experienced reader,and the arrows in the figures are notalways correctly positioned. Clearer dif-ferentiation between proposed andproven pathways would be helpful. Thestructures of the compounds are repeat-ed on each double page, which makesworking with the spectra very easy. Athree-dimensional structure is given forevery compound, but any explanation ashow a given structure was produced (X-ray analysis, simple or advanced molecu-lar modeling) is missing. A set of ques-tions closes each chapter, with answersin the appendix, followed by a free halfpage for your own observations.

The production of the book is not upto the usual high Wiley-VCH standard.While the presentation is nice—every-thing is clearly printed, and color is usedin an advantageous way—the Englishtext is rather bumpy. Furthermore, manytyping errors occur, also sometimes inthe spectral discussions. A bit more at-tention to the language would havehelped the book in every respect.

Last but not least, who will read thisbook? It is not clear to me why this nicebook is a member of the Classics in…family. The title is misleading, becausethe other books in this series point outthose scientific hallmarks of their disci-pline that are still valid today. After read-ing the title, I expected a book discus-sing the most important and cutting-edge spectroscopic methods, exempli-fied on the most difficult problems inthe structure elucidation of natural prod-ucts, historically and recently. In fact, thisbook is a laboratory and spectroscopiccourse with added interesting general in-formation. In essence, Classics in Spec-troscopy is a valuable addition to anyuniversity library and fills a gap not cov-

Natural Classics

2800 www.chembiochem.org � 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim ChemBioChem 2009, 10, 2800 – 2803

Page 2: Classics in Spectroscopy: Isolation and Structure Elucidation of Natural Products. By Stefan Berger and Dieter Sicker

ered by other books. Certainly it will beheavily used by students, especially be-cause of the spectroscopic part.

Stefan SchulzTechnische Universit�t Braunschweig(Germany)DOI: 10.1002/cbic.200900650

Epigenetic Targets in DrugDiscoveryEdited by Wolfgang Sippl andManfred Jung.

Wiley-VCH, Weinheim 2009, 297 pp., hard-cover E 110.00.—ISBN 978-3-527-32355-5

Nearly all the cellsin a human bodyshare the verysame genetic in-formation. Evenso, cellular pheno-types vary dra-matically betweencell types, thusindicating thatdifferent function-al states of thegenome exist, in which distinct sets ofgenes are activated and repressed. Thesedifferent cellular states are set by epige-netic signals (such as methylation of theDNA, modification of histone tails, ornoncoding RNA molecules) that are at-tached to the chromatin and regulatethe expression of genes. Cellular statescan be bequeathed to daughter cells, asillustrated by the process of cellular dif-ferentiation in which, starting from amultipotent state, the future fate of acell becomes more and more restricted.This inheritance of epigenetic states im-plies transmission of epigenetic signals.In fact, there is a continuous transition inthe stability of cellular reactions rangingfrom a transient response to an immedi-ate environmental signal, to alterationsthat are stable over cell divisions, some-times even through a germ line. Re-search has shown that the epigeneticprocesses contribute to a cellularmemory by gradually transforming tran-sient reactions into durable ones. Thus,

the epigenetic cellular memory is of rele-vance for processes in as diverse fieldsas physiology and cellular signaling, neu-robiology, stem cells, or cancer. Disease,by definition, is characterized by a lossof cellular homeostasis that leads toaberrant behavior of the cell. Althoughgenetic changes may be involved in thedevelopment of diseases (like mutationsaccumulating in cancer cells), one mainreason for pathological phenotypes is achange in epigenetic regulation of geneexpression. Thus the dream of correctingpathological processes by “simple” cor-rection of some wrong epigenetic wiringexists. One necessary step towards thislong-term goal is to manipulate the ac-tivity of the epigenetic players : enzymesthat set and remove epigenetic marksand proteins that specifically interactwith these marks.

The book Epigenetic Targets in DrugDiscovery edited by Sippl and Jung, pro-vides an authoritative and comprehen-sive entry into the field of drug designfor epigenetic enzymes. It is written byexperts in the field in a style very appro-priate for both specialist and nonspecial-ist readers. In its initial part, epigeneticprocesses, mechanisms, enzymes, andstructures are reviewed followed bysome technical chapters presenting im-portant methods and assay systemsused. Finally, those drugs and compoundclasses already identified are presented.Reading the book I found many referen-ces to new literature and many interest-ing and important small hints and facts,that were new and illuminating for me.

After going through the approximate-ly 300 pages of the book, it becomesclear that there was and is ongoingenormous progress in this field. Whilebeing impressed, I was still left in somedespair, because current pharmacologi-cal approaches will always cause undir-ected effects, like the inhibition of a his-tone deacetylase or DNA methyltransfer-ase that will affect gene expressiongenome-wide. While there are no doubtsthat this approach will be useful in manycases (and well-documented clinical ex-amples already exist), one would desirehaving access to more targeted rewritingof the epigenetic code to enable a truecorrection of epigenetic mistakes. Itwould be great success of basic and

applied research in molecular epigenet-ics if in ten years or so a book, similarlyinsightful and readable as the work ofSippl and Jung, could be written on thetargeted rewriting of specific epigeneticmarks and its application in medicaltreatments.

Albert JeltschJacobs University Bremen (Germany)

Methods in Molecular Biology,Vol. 515: Viral Applications ofGreen Fluorescent Protein,Methods and ProtocolsEdited by Barry W. Hicks.

Humana Press, Totowa 2009, XI + 357 pp. ,hardcover $ 109.00.—ISBN 978-1-934115-87-9

This book focuses on a very importantarea of application of green fluorescentprotein (GFP) and its variants-––a familyof proteins that was in the truest senseof the word “ennobled” by the NobelPrize for Chemistry in 2008 to MartinChalfie, Osamu Shimomura and Roger Y.Tsien. The importance of this field is alsostressed in the preface of the book, writ-ten by the editor Barry W. Hicks, whocompared the number of publications inthe SciFinder database dealing with GFPto those of other up-to-date technolo-gies. In a timeframe from 1994 to 2005,this number increased from a fewdozens to about 7000, leaving othermodern fields such as RNAi or DNA mi-croarray clearly behind. Very similar num-bers are found in the public PubMed da-tabase, which shows more than 12 500hits when you search for “GFP” or “fluo-rescent protein” in the year 2008. Thesignificance of viral applications of fluo-rescent proteins is well covered in thisbook, which comprises 24 chapters from66 contributing authors from all over theworld and deals with all the major usesof GFP in viral form.

The general structure of the bookchapters begins with an introduction tothe particular topic that explains thebackground and the meaning of thespecific application described. These in-

ChemBioChem 2009, 10, 2800 – 2803 � 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim www.chembiochem.org 2801