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Dictionary of Marine Natural Products. With CD-ROM. Edited by JohnW. Blunt and MurrayH.G. Munro

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Dictionary of Marine Natural
Products
With CD-ROM.
Edited by John W.
Blunt and Murray H. G. Munro.
Chapman & Hall/
CRC, Boca Raton
2007. 2536 pp.,
hardcover
$ 595.00.—ISBN
978-0-8493-8216-1
The Dictionary of Marine Natural Products, which lists over 30 000 individual
compounds from the marine habitat,
forms a part of the Dictionary of Natural
Products, a comprehensive data bank of
natural products, which the publisher
Chapman & Hall has continued for the
past 25 years. The latter complete work
now covers more than 300 000 compounds, and includes other parts on
alkaloids, antibiotics, etc. In their foreword, the editors explain that in this
special volume the entries taken from
the main work have been expanded by
adding a lot of information about the
natural sources of the compounds. However, as the term “marine natural products” is not easy to define precisely, the
collection has been limited to natural
products that are unambiguously of
marine origin. The dictionary covers
the literature up to the middle of 2006.
The editors of this volume, New Zealanders John W. Blunt and Murray H. G.
Munro, are widely-recognized experts in
the field of marine natural products.
They have previously compiled their
own data banks in this field, and are
certainly highly competent to cover this
subject.
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As indicated in the title of this
review, the work consists of a large
handbook with 2415 pages of main text
and a further 159 pages of introduction,
containing detailed instructions for
using the handbook and the data bank,
and information about nomenclature,
classification of marine organisms, etc.
The marine world is enormously
complex and shows immense biodiversity.
The study of the chemical diversity of just
this part of nature has already developed
into one of the most active research areas
of natural products chemistry. However,
it must be emphasized that the metabolites produced by marine organisms are
analogous in their basic structures to
those of land-based nature. Merely glancing through the pages of this large handbook provides ample evidence of that.
Nevertheless, there are differences in the
characteristics of the chemical diversity
that can be attributed to the different
conditions for marine life (for example,
different concentrations of halogens,
chalcogens, and metals) and to the
enzymes with which they are equipped.
In this volume, the publisher and the
editors have devoted much effort to the
enormous, but very important, task of
applying rigorous classification to the
chemical marine world.
For marine natural products, to an
even greater extent than for metabolites
of land-based origin, it is important to
determine whether the substances are
produced by the marine animals and
plants themselves or by the microorganisms (e.g., molds or bacteria) that exist
within them, either mutualistically or
symbiotically. To track down the true
source of marine natural products that
have been isolated, one must first succeed in cultivating small quantities of
such marine microorganisms. Genetic
engineering is being used increasingly to
solve such problems. In other interesting
cases, it has been possible to prove that
certain new natural products are produced by the metabolism of food constituents; this approach has been even
more successful than with products of
land-based origin.
In the handbook the individual compounds are arranged alphabetically, usually by their trivial names, and each
entry is, of course, given an entry
number. Usually, the information consists of the systematic name (according
. 2008 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
to Chemical Abstracts and IUPAC
rules), followed by the Chapman &
Hall entry number, the CAS registry
number, the chemical structure (including stereochemistry if known), the
molecular formula, the molecular mass,
the name of the source organism, and
selected physical data (m.p., b.p., optical
rotation, pKa, etc.) and spectroscopic
data. A very important facility is the
ability to search the data bank on the
basis of these data, including combinations of them and specified ranges (see
below). Compounds wrongly named in
the original literature have been given
their correct IUPAC names. Where the
data in the literature differ, the editors
have tried to give the values most likely to
be correct. Information about toxicity or
other risks (“Hazards and Toxicity”) is
also given where it is known for specific
compounds, and in some cases such
information is mentioned under literature
references. Safety information of this
kind is highlighted in red in the data
bank. Sometimes, however, one finds
surprises—for example, a search for
“abortifacient” gave only one hit: “urea”.
The problems caused by the occurrence of many derivatives of natural
products, and of synonyms in the
naming of products, have been solved
in the Chapman & Hall handbooks by
listing the known derivatives and alternative names below, usually distinguished by italic type, with information
like that given for the main compounds.
Some very important derivatives also
have their own separate entries. Where
different products have been given the
same or very similar names, which
unfortunately happens quite often in
the area of natural products, the entries
are marked with a double cross. Each
entry ends with selected (not comprehensive) literature references, which are
arranged chronologically, with brief
information in parentheses (reference
tags) about specific information or data
contained therein (e.g., isol, uv, ir, pmr,
cmr, struc, synth, tox, etc.). Example:
Kent, R. A. et al., Aust. J. Chem., 1970,
23, 2325–2335 (isol, pmr). The inclusion
of information about derivatives and
synonyms is very important for the
natural products chemist, as it gives a
quick impression of the known variety
of analogues that exist for a particular
basic structure.
Angew. Chem. Int. Ed. 2008, 47, 4956 – 4957
Angewandte
Chemie
Unfortunately, it is not stated in the
literature references whether the information in the publication relates to the
main compound or to the derivatives. To
save space the references are given in an
abbreviated form, with only the name of
the first author, and consequently that is
the only searchable name in the data
bank. In the CD-ROM data bank one
can usually bring up the structures of the
derivatives by a mouse-click on the
screen, whereas in the printed version
one finds only the main structure. The
structural formulas are usually clearly
legible (although the lines are a little too
thin), and are in a uniform and informative style. Sugar moieties are generally
shown in their Haworth projections,
thus allowing a quick comparison of
the stereochemistry.
It is clear from the above that when
one has found an entry for a particular
compound, it provides valuable references to further information, although
one must then do some more searching
in the literature. For help in finding an
entry in the printed version one can use
three indexes: the “Name Index”, the
“Type of Compound Index”, and the
“Type of Organism Index”. However,
the data bank on the CD-ROM offers
far more than that, and its structure is
described briefly below.
The marine natural products data
bank (DMNP) can be installed alongside the main data bank (DNP), which
includes natural products from all environments. If one first copies the CDROM onto the hard disk, then installs
the data bank from the hard disk, it is
not necessary to insert the CD-ROM
again to use the data bank. I did not find
any indication of a time-limit on the use
of this data bank, as there was when
buying the main data bank (DNP). The
enormous advantage of the digital version of the data bank is the ability to
search in not three but 35 different
indexes. The indexes for a search are
chosen by simply mouse-clicking on a
list. For searching in these fields one can
use a combination of the well-known
Boolean operators (“and”, “or”, “not”)
and range-defining operators (< , > , , , and –). It is also possible to specify
ranges for all numerical values. An
example of this is the melting point: it
is well known that widely different
values are given in the literature, and
Angew. Chem. Int. Ed. 2008, 47, 4956 – 4957
therefore the ability to search over a
range is very useful. In one example, a
search that specified a melting point
(sometimes called Fp, sometimes Mp)
within the range 200 – 202 8C (the spaces
before and after the dash are essential,
since otherwise it would be interpreted
as a minus sign) and a molecular mass
greater than 200 (> 200) gave 208 hits.
By instead giving the more accurate
data, 202 – 205 8C and molecular mass
300 – 301, one obtains just a single hit,
under the main entry neocomantherin
(synonym: 8-hydroxy-5,6-dimethoxy-2propyl-4H-naphtho[2,3-b]pyran-4-one)
with molecular mass 314.337. However,
the actual hit is not on this compound
but on a derivative, the corresponding
des-methyl compound, with molecular
mass 300.31. This hit was not highlighted
by color, and thus a little searching is
sometimes also necessary. This kind of
combined search using specified ranges
of certain physical data is one of the best
ways of searching for known natural
products in cases where a few data for a
newly isolated natural product are available. A search in this form is not
otherwise possible, for example in
Chemical Abstracts. Unfortunately, one
cannot search on the basis of NMR or
IR data, only on that of UV maxima.
A search based on the first author is
best carried out using the “References”
index. Alternatively, one must type in
AUTH = before the authorIs name, for
example AUTH = Faulkner—in this
case 16 hits were obtained. It is not
necessary to truncate the name.
In a search based on the exact
molecular mass, one must give all six
decimal places; truncating the value to
fewer decimal places does not help.
Searching based on the names of organisms, which often consist of several parts,
can be carried out using just a single
name. Searching in the indexes by name
is made easier by entering the first
letters of the complete name under
“add term”. As with any data bank,
one needs to spend some time learning
by experiment before one can use the
system most effectively.
The list of compound names (usually
the trivial name, but occasionally the
systematic name) appears on the monitor screen, and by mouse-clicking on
the list one reaches the desired entry, in
essentially the same form as it appears in
the printed handbook. One can then
“copy and paste” the text, or a selected
part of it, into a text processing program.
It does not seem to be possible to do the
same with the structures. However, the
structures (which, unlike the printed
handbook, also include most of the
derivatives) can be double-clicked to
display them on the monitor screen
above a blue benzene ring. It is possible
in principle to search in the data bank by
both texts and graphics, and one can
choose between searching based on the
exact structure or on a substructure.
ChemDraw structures, if they are small,
can be recognized when they are copied
into the system; alternatively, one can
import structures in three different formats, including the MDL MOL format.
The speed of searching is acceptable,
even with fairly large structures, and a
search is usually complete in less than
half a minute. Combined searching on
the basis of structure and text, in the
different forms described above, is possible and works very well. Thus, apart
from the lack of a facility for including
NMR and IR data, the searching capabilities cover practically every need.
In conclusion, however, one questions arises in relation to this work: Is it
necessary to buy the separate part, the
Dictionary of Marine Natural Products,
if one already has access to the Chapman & Hall main work, the Dictionary
of Natural Products? Most of the data in
the partial work are also contained in
the main work, as I found by some trials,
although the partial work may provide a
little more detail in some cases. The fact
that a structure search in the larger data
bank of the main work takes 8–10 times
longer than in the smaller data bank is
certainly a consideration. As the Dictionary of Marine Natural Products
contains a smaller quantity of data,
which is therefore easier to process, the
work should certainly be recommended
for groups engaged in research on
marine natural products. It is also suitable for libraries and, to some extent, as
a reference source for users other than
chemists.
Karsten Krohn
Institut f8r Chemie
Universit:t Paderborn (Germany)
DOI: 10.1002/anie.200785567
. 2008 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.angewandte.org
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