摘要:

Book reviews Alkaloids Chemical and Biological Perspectives Vol. 14 Ed. S. W. Pelletier Pergamon 1999 560 pp. price US$292.50 ISBN 0-080-43665-X The continuing value of Natural Product Reports attests to the abiding importance of natural products exemplified amongst others by the alkaloids of which ten thousand or more richly diverse examples are known. Interestingly and uniquely among such naturally occurring compounds the alkaloids are very well served by a comprehensive review literature. The bedrock of this literature has long been the series first edited by R. H. F. Manske and which initially appeared a distant half century ago. The reviews are characterised in general by an orderly and detailed survey of different groups of alkaloids with judicious updates.Thus through ‘Manske’ and on into Natural Product Reports one has been able to track all of the relevant chemistry and biology of these fascinating nitrogeneous compounds. (A stately change of editors occurred with Volume 21; the current editor is G. A. Cordell.) There are other ways to keep up with the natural product literature notably by means of The Dictionary of Natural Products (Chapman-Hall) which is available on updating CD ROM. There is also another distinguished alkaloid series that should be consulted. Since 1983 a series of reviews called Alkaloids Chemical and Biological Perspectives has been published edited by S. William Pelletier himself a distinguished alkaloid chemist that is slightly different but complementary to Manske.The surveys tend to be individual if not personal essays within the field rather than strictly systematic reviews. And so we come to the latest volume in the series Volume 14 which is concerned with three such essays. The first is a labour of love by Paul L. Schiff Jr. on bisbenzylisoquinoline alkaloids. It is a largely tabular review in 235 pages of these large dimeric bases that is drawn from four earlier surveys written by the reviewer. It succeeds handsomely in its aim of being ‘a useful pragmatic tool for the bench scientist’ which provides the reader with a comprehensive description of botanical distribution and occurrence of these alkaloids in several different tables. A listing of structures and the discussion types is provided.Clearly this is for reference not bedtime reading. The second review fits more with bedtime reading; it too is accompanied by tables. This second review is a competent survey of the alkaloids from Malaysian flora by T.-S. Kam. As the author points out ‘it is somewhat artificial to suppose that flora are respecters of national boundaries’; the survey could easily be similar to one on the flora found elsewhere in South East Asia. Interestingly the alkaloids from the plants of Thailand are covered similarly in Volume 41 of the Manske series. The third and last review is concerned with something completely different the application of palladium chemistry to the total synthesis of naturally occurring indole alkaloids by J. J. Li. This is a comprehensive survey that includes all the main type of C–C bond forming reactions involving palladium.Richard Herbert University of Leeds UK This journal is © The Royal Society of Chemistry 2000 The Handbook of Natural Flavonoids Ed. J. B. Harborne and H. Baxter John Wiley and Sons 1999 889 xiii pp. and 879 xvi pp. (2 volumes) price £595 ISBN 0-471-95893-X The cover description proclaims these two volumes to be edited by one of the world’s acknowledged leading researchers in flavonoid chemistry and biochemistry and are the essential guide to the chemical structure and function of all known flavonoids containing full references CAS numbers chemical structures molecular formulae and several extensive indexes. It goes on to say The Handbook of Natural Flavonoids is the definitive reference to this large and important group of natural products for researchers in pharmaceutical and medicinal chemistry plant biochemistry and organic chemistry.I was more than happy to review these volumes and looked forward to seeing this ‘essential guide’ and ‘definitive reference’ to a group of compounds that had formed a mainstay of my research for many years. As I delved into these volumes I became very disappointed by what I found and felt that despite the obvious amount of work that had gone into their preparation a golden opportunity to produce a valuable and usable reference work had been missed. I don’t know whether this handbook is aimed primarily at flavonoid specialists or towards researchers from other areas who want some flavonoid data; in my opinion both groups will be frustrated from what little they find.Each volume is written as a self-contained unit. Volume 1 covers flavones flavone O-glycosides flavonols flavonol O-glycosides C-glycosylflavones and biflavonyls and Volume 2 anthocyanins chalcones dihydrochalcones aurones flavanones dihydroflavonols flavans and proanthocyanins isoflavonoids and neoflavonoids in separate sections as indicated. Each volume starts with the same three-page general introduction to the flavonoids rich in flavonoid-specific jargon and not very user-friendly to the non-specialist. This is followed by succinct introductions to the separate groups of compounds which include structural variations encountered numbering distribution in nature biological activities etc.and references to earlier reviews and compound listings. Overall introductory remarks take up only six pages in Volume 1 and ten pages in Volume 2. Because of the rather specific comments about the various groups including explanations of the abbreviations used I considered these remarks would have served their purpose rather better if located adjacent to the listings for those particular groups. The main content is the listing of natural flavonoids in the style of several other publications notably the Dictionary of Organic Compounds and the Dictionary of Natural Products but it falls well short of the standard set by these two. For each compound there is its trivial name and other names (if any) a structure class of flavonoid molecular formula CAS number molecular weight biological sources biological activity (if any) and one or perhaps two references.Sugars in glycosides were nicely shown with their conformations rather than as Haworth representations or abbreviations. Each compound has its own number which run through the various flavonoid groups from 1–3147 in Volume 1 and 1–3320 in Volume 2 so 421 Nat. Prod. Rep. 2000 17 421–422 that there is no unique number ascribed to a particular compound. At the end of each volume there is a subject index containing both trivial and systematic names and a species index which lists flavonoid names under each biological species referred to. I thought the amount of information presented for each compound was minimal and not that useful.There were no physical data. References were not cited in any way that gave any indication of what might be found there. There could be a dozen or more plant species listed as sources but to which the reference might lead would be a lucky dip. Where might one go to find a proton or carbon-13 NMR spectrum UV spectrum optical data details of isolation or a study of biosynthesis? Stereochemistry a fairly important aspect of natural products was swept under the carpet as far as possible. In many cases the stereochemistry may not be known but it is very important to put it in where it is known. So whilst dihydroflavonol and flavan structures were presented with stereochemistry flavanone and isoflavonoid stereochemistry was totally ignored.Occasionally different CAS numbers were shown because of () () or racemic forms but one was presented with no further information about which enantiomer was which. Over the years I have contributed several reviews and checklists on isoflavonoids to The Flavonoids which in its various guises comprised regular five-yearly updates on the area edited as always by the highly respected Jeffrey Harborne. I thus felt sufficiently well-informed to cast a particularly critical eye over the isoflavonoid section to assess its value. The introductory remarks outline the need to separate the isoflavonoids into groups in the order isoflavones isoflavanones rotenoids pterocarpans etc. with structures listed in order of increasing chemical complexity.This is duly followed but then halfway through this sequence starts again! I note that the first group covers the literature up to about 422 Nat. Prod. Rep. 2000 17 421–422 1981 then we get the 1982–1990 literature reports with no attempt to integrate the two sets. I couldn’t find any isoflavonoid references later than 1990 though a Natural Product Reports review published in 1995 covers the 1991–1993 literature. Other classes of flavonoid did feature references as far as 1995 or 1996 depending on class. I noted that homopterocarpin and pterocarpin had the same two (but only two) references which are actually from 1887 and 1935 hardly the most up to date or useful ones for the reader. That old chestnut myriconol reappears in this listing.This compound was established not to be a rotenoid back in 1971. I also found a number of other irritations and inconsistencies. Through the isoflavonoids I also tested the efficacy of the indexes. Both isomucronulatol and 7,2-dihydroxy-3,4-dimethoxyisoflavan led me correctly to Colutea arborescens and vice versa. Trifolium pratense gave me 9-O-methylcoumestrol but not medicarpin maackiain or the major isoflavonoid formononetin. These compounds could however be found under Trifolium species. The self-contained nature of the two volumes means you will have to use the indexes of both books if you do not know the class of flavonoid involved. Unfortunately there is no formula index. I have tried hard to like The Handbook of Natural Flavonoids but I regret to say I found the content not particularly inspiring and I rate it less useful to the flavonoid researcher than the last volume (1994) of The Flavonoids. It is a disgrace that in some areas (certainly isoflavonoids) it is no more up to date than that book five years on. There are serious shortcomings in the amount and level of information presented and I cannot seriously recommend it to either libraries or to individuals. At its unreasonably high price it does not seem to offer value for money. Paul M. Dewick University of Nottingham UK

ISSN:0265-0568    

DOI:10.1039/a004bkry

出版商:RSC    

年代:2000

数据来源: RSC