Monoterpenes, A. A. Swigar and R. M. Silverstein, Aldrich Chemical Co., Milwaukee, Wisconsin, 1981....

1
BOOK REVIEWS 24 1 MONOTERPENES, A. A. Swigar and R. M. Silverstein, Aldrich Chemical Co., Milwaukee, Wisconsin, 1981. No. of pages; iv + 130, price E25.80. This book was marked as ‘new’ in Aldrich’s 1991- 1992 Flavors & Fragrance Catalogue but it was originally published in 1981 and has been quoted in this journal. It is a useful collection of spectra-mass, infrared, ‘H-NMR and, in most cases, I3C-NMR- of 122 mono- terpenes arranged in alphabetical order of the common names. In addition to the spectra, for each compound the structure, molecular formula and the Kovats constant on OV-101 are also given. The common name index gives the Chemical Abstracts systematic name and the Chemi- cal Abstracts systematic name index gives the common name and number of the spectrum. Also provided is a molecular formula index, a chemical class index and a mass spectral index in order of decreasing m/e of base peaks. With my review copy was enclosed an undated Errata and Comments section, which is probably the ‘new’ component. A number of sensitive terpenes were found to have undergone thermal rearrangement and/or dehydration in the inlet system or in the source of the mass spectrometer used in the original work. Twenty- nine new mass spectra, measured under very mild ther- mal conditions on a Finnegan 4OOO GC-MS, are now presented together with a new mass spectral index and ten errata or comments. This handbook, with its update, will be welcomed in all laboratories working with essen- tial oils. A companion volume dealing with sesquiter- penes would be even more welcome. ROGER STEVENS Threlkeld STUDIES IN NAIURAL PRODUCTS. VOLUME 9: STRUCTURE AND CHEMISTRY, (Part B), edited by Atta-ur-Rahman, Elsevier Science Publishers BV, Amsterdam, 1991. No of pages: xviii + 634, price US$ 220.50, Dfl. 430.00. ISBN 0-444- 89 165-X. As the not-very-informative title ‘Structure and chem- istry’ of Volume 9 of this series more or less suggests, the subjects treated in 24 chapters by specialists in the field cover a very broad range. This is exemplified by an index of 22 double-column pages. Although the common de- nominator is ‘natural products’, its treatment varies from the purely instrumental, over synthesis, to biochemistry, and in many instances contains all three. The chapters are written in the form of reviews, mostly based on the personal experience of the authors. Thirteen papers put the accent on the use of instru- mental techniques: the scope of single-crystal X-ray diffraction as a powerful tool for structure determination is shown with marine products, when ”C- and ‘H-NMR experiments alone did not allow unambiguous conclu- sions; an in-depth study based on 13C- and ‘H-NMR data for the determination of the absolute stereochem- istry of new norterpene cyclic peroxides of marine origin, leading to the stereochemical reassignment of over a dozen ‘known’ substances; the identification of a miscel- laneous collection of new substances from terrestrial and marine plants (saponins, sesquiterpenes, alkaloids, diter- penes, halogenated sesquiterpenes, sterols) mainly by “C-NMR and negative ion FABS-MS techniques; an NMR strategy for the deduction of the structure of complex molecules, applied to two new heptanortriter- penoids from Entandrophragma utile (Meliaceae); hetero- atoms in NMR spectrometry; a descriptive approach to the theory of modem 2-D NMR techniques; an exten- sively documented and practical method for the identifi- cation of trace amounts of indole alkaloids using H-NMR; the structure determination by spectrometric means and confirmation by synthesis of sesquiterpenoids of liverworts or marine organisms, and structure determi- nation of complex aromatic structures by ‘H-NMR spectrometry; the isolation and identification of a series of components from the heartwood of Euphorbiafidjiana, making extensive use of high field NMR techniques; isolation and identification of cytotoxic triterpenoids from fresh leaves of Nerium oleander. Isolation and identification of new biologically active triterpenes from Azodirachta indica; a review of the methodology for the analysis (separation and identification) of plant steryl esters based on chromatography (TLC, GC, HPLC) and mass spectrometry; a paper on the use of FABMS/MS in the field of peptides and proteins; the structure determi- nation of peptide siderophores (complexing agents of Fe3+) of bacteria. While still making use of instrumental techniques, the remaining papers treat the subject of the structure of natural products more from a phytochemical, biochemi- cal and metabolic point of view: a review of rare cyclo- propane and even more uncommon cyclopropene containing sterols of marine origin, and their biochem- istry; the production of secondary metabolites (mostly mycotoxins) by Fusarium species, their isolation, identifi- cation and chemical synthesis; germination self-inhibi- tors from uredospores of rusts (Uromyces phaseoli and P uccinia species) and from conidia of Colletotrichum species; a highly informative report on isoprenoid phen- olic lipids, mainly in connection with cashew nuts (bio- synthesis, production, analysis, synthesis); three simple, effective bioassays (with detailed descriptions) to help phytochemists detect bioactive substances with a poten- tial as antitumour agents, pesticides, herbicides, plant growth regulators, documented with ten different plant species; the use of j-sitosterol as the starting material for the preparation of corticoid hormones by a combination

Transcript of Monoterpenes, A. A. Swigar and R. M. Silverstein, Aldrich Chemical Co., Milwaukee, Wisconsin, 1981....

BOOK REVIEWS 24 1

MONOTERPENES, A. A. Swigar and R. M. Silverstein, Aldrich Chemical Co., Milwaukee, Wisconsin, 1981. No. of pages; iv + 130, price E25.80.

This book was marked as ‘new’ in Aldrich’s 1991- 1992 Flavors & Fragrance Catalogue but it was originally published in 1981 and has been quoted in this journal. It is a useful collection of spectra-mass, infrared, ‘H-NMR and, in most cases, I3C-NMR- of 122 mono- terpenes arranged in alphabetical order of the common names. In addition to the spectra, for each compound the structure, molecular formula and the Kovats constant on OV-101 are also given. The common name index gives the Chemical Abstracts systematic name and the Chemi- cal Abstracts systematic name index gives the common name and number of the spectrum. Also provided is a molecular formula index, a chemical class index and a

mass spectral index in order of decreasing m/e of base peaks. With my review copy was enclosed an undated Errata and Comments section, which is probably the ‘new’ component. A number of sensitive terpenes were found to have undergone thermal rearrangement and/or dehydration in the inlet system or in the source of the mass spectrometer used in the original work. Twenty- nine new mass spectra, measured under very mild ther- mal conditions on a Finnegan 4OOO GC-MS, are now presented together with a new mass spectral index and ten errata or comments. This handbook, with its update, will be welcomed in all laboratories working with essen- tial oils. A companion volume dealing with sesquiter- penes would be even more welcome.

ROGER STEVENS Threlkeld

STUDIES IN NAIURAL PRODUCTS. VOLUME 9 : STRUCTURE AND CHEMISTRY, (Part B), edited by Atta-ur-Rahman, Elsevier Science Publishers BV, Amsterdam, 1991. No of pages: xviii + 634, price US$ 220.50, Dfl. 430.00. ISBN 0-444- 89 165-X.

As the not-very-informative title ‘Structure and chem- istry’ of Volume 9 of this series more or less suggests, the subjects treated in 24 chapters by specialists in the field cover a very broad range. This is exemplified by an index of 22 double-column pages. Although the common de- nominator is ‘natural products’, its treatment varies from the purely instrumental, over synthesis, to biochemistry, and in many instances contains all three. The chapters are written in the form of reviews, mostly based on the personal experience of the authors.

Thirteen papers put the accent on the use of instru- mental techniques: the scope of single-crystal X-ray diffraction as a powerful tool for structure determination is shown with marine products, when ”C- and ‘H-NMR experiments alone did not allow unambiguous conclu- sions; an in-depth study based on 13C- and ‘H-NMR data for the determination of the absolute stereochem- istry of new norterpene cyclic peroxides of marine origin, leading to the stereochemical reassignment of over a dozen ‘known’ substances; the identification of a miscel- laneous collection of new substances from terrestrial and marine plants (saponins, sesquiterpenes, alkaloids, diter- penes, halogenated sesquiterpenes, sterols) mainly by “C-NMR and negative ion FABS-MS techniques; an NMR strategy for the deduction of the structure of complex molecules, applied to two new heptanortriter- penoids from Entandrophragma utile (Meliaceae); hetero- atoms in NMR spectrometry; a descriptive approach to the theory of modem 2-D NMR techniques; an exten- sively documented and practical method for the identifi- cation of trace amounts of indole alkaloids using

’ H-NMR; the structure determination by spectrometric means and confirmation by synthesis of sesquiterpenoids of liverworts or marine organisms, and structure determi- nation of complex aromatic structures by ‘H-NMR spectrometry; the isolation and identification of a series of components from the heartwood of Euphorbiafidjiana, making extensive use of high field NMR techniques; isolation and identification of cytotoxic triterpenoids from fresh leaves of Nerium oleander. Isolation and identification of new biologically active triterpenes from Azodirachta indica; a review of the methodology for the analysis (separation and identification) of plant steryl esters based on chromatography (TLC, GC, HPLC) and mass spectrometry; a paper on the use of FABMS/MS in the field of peptides and proteins; the structure determi- nation of peptide siderophores (complexing agents of Fe3+) of bacteria.

While still making use of instrumental techniques, the remaining papers treat the subject of the structure of natural products more from a phytochemical, biochemi- cal and metabolic point of view: a review of rare cyclo- propane and even more uncommon cyclopropene containing sterols of marine origin, and their biochem- istry; the production of secondary metabolites (mostly mycotoxins) by Fusarium species, their isolation, identifi- cation and chemical synthesis; germination self-inhibi- tors from uredospores of rusts (Uromyces phaseoli and P uccinia species) and from conidia of Colletotrichum species; a highly informative report on isoprenoid phen- olic lipids, mainly in connection with cashew nuts (bio- synthesis, production, analysis, synthesis); three simple, effective bioassays (with detailed descriptions) to help phytochemists detect bioactive substances with a poten- tial as antitumour agents, pesticides, herbicides, plant growth regulators, documented with ten different plant species; the use of j-sitosterol as the starting material for the preparation of corticoid hormones by a combination