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Book Review Dictionary of Alkaloids. Edited by I. W. Southon and J. Buckingham

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as all students should have already learned in their preparative work how to write reports. In any case, it is not possible
to lay down a report structure which can be applied universally. On the other hand, a useful feature are the exercises
which the student can work through to test his or her knowledge of the methods for detecting functional groups and of
the most important derivatizations for particular classes of
compounds. However, the learning content of the exercises
could have been further increased by including references to
the IR, ‘H NMR and 13CNMR spectra of the compounds.
Despite the fact that at some universities wet analytical
methods are no longer taught, due to the shortening of studies and to the introduction of essential courses on topics such
as spectroscopy and separation techniques, every student
should work through this book. The experimental exercises
and the practical hints are extremely valuable. It is especially
worth mentioning that only a very few errors could be detected. The book has the usual high standard of production of
the Thieme publishing house, and its price is reasonable,
even for students.
Klaus Weinges [NB 1008 IE]
Organisch-Chemisches Institut
der Universitat Heidelberg (FRG)
Dictionary of Alkaloids. Edited by I. W: Southon and J.
Buckingham. Chapman and Hall, London 1989.1161 pp./
index 620 pp., hardcover, L 675.00. -ISBN 0-412-24910-3
The alkaloids, with over 300 structural types and biosynthetic branches, form a group of secondary metabolites
whose variety of structures is unrivalled by any other class of
substances in nature. Since in many cases they show high
toxicity or have other striking physiological effects, they
have long attracted the interest of chemists; their structures
continue to present challenges to analytical, synthetic and
biosynthetic chemists, as befits their great importance in
medicine and research, as toxins, and in chemotaxonomy
and the classification of plants.
As the number of known natural products has grown, the
definition of the term “alkaloid” has become widened to
include not only basic plant substances but also non-basic
nitrogen compounds. The editors of the present book now
take this a step further by including almost all naturally
occurring nitrogen-containing secondary metabolites of
plant, microbial and animal origin; thus the definition is no
longer based on physiological effects, nor on basicity.
In view of this wide definition of alkaloids, it is understandable that the present book contains an enormous number of compounds - about 10000. Thus the extent of this
compilation is greater than in any other similar work. The
only nitrogen-containing natural products that are omitted
or not treated in full are a few simple lower amines, the
nucleobases and nucleosides, and the pterins. Besides true
peptides, the amino acids are also not covered (with only a
few exceptions), but the amines such as tryptamine that are
derived from these by decarboxylation are included. However, the peptide alkaloids are covered thoroughly.
In contrast to other well-known compilations, the alkaloids are not arranged according to the types of organisms
that produce them, nor on the basis of (bio)chemical criteria,
but are instead listed in alphabetical order. In adopting this
method the editors define their aim as that of collecting
together accurate and critical data on all known alkaloids, or
Angew Chem. lnr.
Ed. Engl. 29 (1990) No. 5
at least on those whose structures are known. This necessitates summarizing the information in a concise form; each
entry begins with the name, giving the most usual one where
several alternatives exist, followed by the systematic name.
This is followed by the stereochemical formula according to
the current state of knowledge (showing the absolute configuration where this is known); the stereochemical diagrams
are well-drawn and essentially free from errors. However,
the representation of the sempervirin structure as an N,Nzwitterion seems rather unconventional, in contrast to the
more usual representation as given, for example, for the related alkaloid melinonin E. Following the molecular formula, molecular mass and origin, the entry lists the main physical properties (melting and boiling points, specific rotation,
refractive index) for the parent compound, and often also for
derivatives, together with information on biological activity.
For some alkaloids, however, the last item could have been
more complete; for example, the toxicities of the various
curare alkaloids have been very precisely determined by
Wieiand, whereas this compilation only gives these data for
the main alkaloids, and even here instead of LD 50 values in
most cases there is only a general statement such as “highly
toxic”.
For the many alkaloids whose structures are still unknown, this compilation of data is especially useful, since all
the information contained in the secondary literature has
been extracted from the different sources, critically evaluated, and reduced to a consensus! It would, of course, have
been useful to have spectroscopic data too, but this would
scarcely have been practicable within the predetermined size
of the book. For these the reader is referred to the HEILBRON data bank, from which the present dictionary of alkaloids, like the dictionary of antibiotics from the same publisher, is an extract in book form. This accounts for the
contents of the book being very up-to-date, a fact which is
especially obvious in the literature citations.
Under each entry there is a bibliography, which includes
publications up to the beginning of 1988, and is indexed
under various headings such as isolation, structure determination, spectroscopic data and synthesis. Another very useful item included is the Chemical Abstracts Registry Number, which facilitates making a more extensive literature
search if needed.
Preceding the alphabetically listed information on individual alkaloids there is a 32-page description of the main types
of alkaloids, of which there are about 35. Here nomenclature
and biosynthetic relationships are discussed in a condensed
but very lucid form, with many examples. A list of review
literature is provided with each section.
One can well believe the claim that all alkaloids known up
to the beginning of 1988 are listed: the reviewer can hardly
be expected to check this, of course, and a few tests will have
to suffice. In the main part of the dictionary the simplest
alkaloids, such as benzylamine, are, of course, readily found,
but one can also find those with highly complex structures,
such as leurosin and virotoxin. However, not all of these are
listed under the expected names: whereas dimethyltryptamine and bufotenin are included under these names, serotonin
appears at first glance to be absent, but is then found under
5-hydroxytryptamine. The isomeric psilocin (and also psilocybin), on the other hand, appear under their systematic
names. Yet other alkaloids are not listed separately, but appear under the corresponding parent compounds. As a result
one finds, for example, that only the nitrogen-free compound 12-oxooctadecanoic acid appears as a structural formula, whereas the alkaloid derived from it, lycaonic acid
piperidide, does not.
0 VCH Verlagsgesellschaft mbH, 0-6940
Weinheim, 1990
0570-0~33~90~0505-0S61$02.50/0
561
In these cases, therefore, one needs to use the separately
bound names index, which contains all the systematic names
and common trivial names that are listed in the main work.
Here it is worth noting that many of the names from the
older literature have been altered to conform with modern
rules of nomenclature. The index volume also contains a
molecular formulas index, a list of CAS Registry Numbers,
and an index of compound types. In this each alkaloid is
assigned to one or more of 296 groups arranged mainly according to structural types, which enables one to easily obtain a complete survey of alkaloids of a particular type, e.g.
mold alkaloids, alkaloid-N-oxides, tropane alkaloids, or
compounds related to morphine.
The species index, containing nearly 20000 references, is
without doubt an especially useful feature, even though it
has a few gaps--for example, under the anhalonium types
the important alkaloid mescalin is not listed. Under the botanical name Corfinarius orellanus one finds, as expected, a
reference to orellanin. However, the peptide structure for
cortinarin, which although it seems unlikely has not yet been
disproved, is not mentioned here-ould
this be a result of
critical selection?
With such an all-embracing definition of alkaloids it is
inevitable that the boundaries are somewhat fluid, and this
unavoidably leads to some inconsistencies. For example, although indirubin is included, the better-known indigo isomer is absent; also not mentioned are indoxyl and isatin.
However, one hardly expects to find these compounds in a
book on alkaloids in any case; their omission is therefore a
trivial matter in this extremely up-to-date survey of the literature on alkaloids, which is the most complete printed compilation available anywhere on the subject. Of course, it goes
without saying that a mammoth work of this nature, which
is comprehensive and up-to-date to a degree otherwise only
achieved in computerized data banks, is priced accordingly.
To read this book is aesthetically pleasurable, in addition to
the information that it yields; it should be in every library
which is concerned with natural products.
Hartmut Laatsch [NB 1004 IE]
Institut fur Organische Chemie
der Universitat Gottingen (FRG)
Preparative Polar Organometallic Chemistry. Val. 1. By L.
Brandsma and H . D. Verkruijsse. Springer, Berlin 1987.
240 pp., paperback, DM 78.00. - ISBN 3-540-16916-4
When one compares the increase in the library budget (at
any rate, that in Marburg) with the increase in the cost of
journals and books, the effect in recent years has been to cut
resources, making it necessary to exercise special care over
the purchase of new books. Can we or can we not afford a
certain book? In this case the answer must be an unqualified
“yes”, if only because, pursuing this economic theme, the
book by Brandsma and Verkruijsse enables one to save money. The authors have produced an extremely practical book,
a “laboratory manual”, as they call it, for chemistry students
and for chemists in industrial and university laboratories.
Nothing has been left to chance; all the laboratory recipes
have been tested several times by the authors themselves,
who have a great deal of experience in the field of polar
organometallic compounds. Everyone who has ever worked
with a recipe which is not reproducible (or which does not
work at all!) will appreciate what it means to use one that has
been tested and optimized.
562
0 VCH
~rlagsgeselkchaftmhH, 0-6940 Weinherm,1990
The book deals with polar organometallic compounds (intermediates) obtained from sp2 compounds. Chapter ’I gives
an introductory general survey entitled “0rganomet:tllic
Reagents, Solvents and Laboratory Equipment”. This includes useful hints on the safe handling of such compounds,
and also on their disposal. The following chapters are: Chapter 2 “Reactivity of Polar Organometallic Intermediates”,
Chapter 3 “Metallated Olefinic and Allenic Hydrocarbons”,
Chapter 4 “Metallation of Hetero-Substituted Unsaturated
Systems”, Chapter 5 “Metallated Hetero-Aromatic Compounds”, and Chapter 6 “Metallated Aromatic Compounds”. There is a very useful appendix consisting of tables
from which the reader can find suitable methods for preparing any particular polar organometallic compound, and for
reacting it with an electrophilic species. Another table lists
typical reaction conditions with a wide variety of electrophiles.
In summary, anyone who wishes to save money and avoid
irritation in preparing and carrying out reactions with polar
organometallic compounds should buy this book by Brandsma and Verkruijsse. The money will be well spent.
Gernot Boche [NB 1010 IE]
Fachbereich Chemie
der Universitat Marburg (FRG)
Spectrometric Titrations. Analysis of Chemical Equilibria. By
.
I
Polster and H . Lachmann. VCH Verlagsgesellschaft,
Weinheim 1989. 433 pp., hardcover, DM 196.00. ISBN 3-527-26436-1
The meaning primarily attached to the word “titration” is
the method introduced by Gay-Lussac for the quantitative
determination of dissolved substances. The end-point of
such a titration is usually determined using an indicator
which undergoes a color change. However, it was soon recognized that this method can be used to investigate a wide
variety of other equilibrium systems. The changes in the
physical condition of the system are observed in either a
stepwise or a continuous fashion by means of suitable instruments which detect changes in variables such as pH, electrical conductivity, optical density, fluorescence or optical rotation. From the resulting titration curves it is then usually
possible to calculate the equilibrium constants, which play a
fundamental role not only in chemistry and physics, but also
in biochemistry and medicine, pharmacy and toxicology,
and other areas.
Part I of this book deals with the basic theory and methodology of spectrometric titration. The topics covered are the
classification of the various methods, the graphical treatment of the experimental data, multiple wavelength spectrometry, and thermodynamic and electrochemical principles.
Part I1 discusses in detail the formal treatment of titration
systems and the calculation of results. Acid-base equilibria
involving one, two, three and still more stages are considered, and methods of treating the data by iterative curve
fitting and statistical analysis are described. For non-overlapping multi-stage titration systems it is necessary to add an
external standard proteolyte whose pK-value is known very
accurately; from the simultaneous titrations one can then
determine a relative pK-value for the equilibrium being investigated. Branched acid-base equilibria, metal complex
equilibria, association equilibria and redox equilibria are
also considered.
o570-o833]90j050S-a5623 02.80j0
Angen. Chrm. Int. Ed Engl. 29 (1990) No 5
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