The organic constituents of higher plants: their chemistry and interrelationships
320 Pages
English
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The organic constituents of higher plants: their chemistry and interrelationships

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Downloading requires you to have access to the YouScribe library
Learn all about the services we offer
320 Pages
English

Description

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I 1^ LIFE SCIENCE SERIES
Consulting Editors
ROBERT H. BURRIS, Biochemistry
HERMAN C. LICHSTEIN, Microbiology
PRINCIPLES OF RADIOISOTOPE METHODOLOGY. .Chase
IDENTIFICATION OF
ENTEROBACTERIACEAE Edwards-Ewing
PROCEDURES FOR ROUTINE
DIAGNOSIS OF VIRUS AND
RICKETTSIAL DISEASES Kalter
HANDBOOK OF CELL AND
ORGAN CULTURE Merchant-Kahn-Murphy
ELEMENTARY BIOCHEMISTRY Mertz
NUCLEIC ACID OUTLINES:
Vol. I—Structure and Metabolism Potter
BEHAVIOR OF ENZYME SYSTEMS Reiner
THE ORGANIC CONSTITUENTS OF
HIGHER PLANTS: THEIR CHEMISTRY
AND INTERRELATIONSHIPS Robinson
METABOLIC MAPS, Volume II Umbreit
MANOMETRIC TECHNIQUES Umbreit-Burris-StaufFer L^
ci\<
THE ORGANIC CONSTITUENTS
OF HIGHER PLANTS
Their Chemistry and Interrelationships
by
TREVOR ROBINSON
Chemistry Department
University of Massachusetts
Amherst, Mass.
with contributions by
ERNEST SONDHEIMER
Department of Forest Chemistry
New York State College of Forestry
Syracuse, New York
BURGESS PUBUSHING COMPANY
Minneapolis 15, Minn.426 South 6th Street, Copyright © 1963
by
Trevor Robinson
All rights reserved
Library of Congress Catalog Card No. 63-8920
Printed in the United States of ...

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iiijijljii; Miiililiiili ilillfili;: liif^ :!;!:: "lit:- ORGANIC CONSTITUENTS PLANTS ROBINSON .TitiT-^'-i-''- ! t': itt:mm tin iiiii iJiaini'',:; WS^. "( v.';- ."w tl li.-i: attihiaiiiiilifiiifjiiiJiiUiiitt tHmUI»jmHUiiiijhJn2iiiti>!HiiiiHiiii{iiHJi»Hi{Mmu(hlli!liidtUtSilHnintii! ;^lii»iK :r zri =X r-q I°§1 i•^— ^-IS I torn r^11 I Ia im C3 I 1^ LIFE SCIENCE SERIES Consulting Editors ROBERT H. BURRIS, Biochemistry HERMAN C. LICHSTEIN, Microbiology PRINCIPLES OF RADIOISOTOPE METHODOLOGY. .Chase IDENTIFICATION OF ENTEROBACTERIACEAE Edwards-Ewing PROCEDURES FOR ROUTINE DIAGNOSIS OF VIRUS AND RICKETTSIAL DISEASES Kalter HANDBOOK OF CELL AND ORGAN CULTURE Merchant-Kahn-Murphy ELEMENTARY BIOCHEMISTRY Mertz NUCLEIC ACID OUTLINES: Vol. I—Structure and Metabolism Potter BEHAVIOR OF ENZYME SYSTEMS Reiner THE ORGANIC CONSTITUENTS OF HIGHER PLANTS: THEIR CHEMISTRY AND INTERRELATIONSHIPS Robinson METABOLIC MAPS, Volume II Umbreit MANOMETRIC TECHNIQUES Umbreit-Burris-StaufFer L^ ci\< THE ORGANIC CONSTITUENTS OF HIGHER PLANTS Their Chemistry and Interrelationships by TREVOR ROBINSON Chemistry Department University of Massachusetts Amherst, Mass. with contributions by ERNEST SONDHEIMER Department of Forest Chemistry New York State College of Forestry Syracuse, New York BURGESS PUBUSHING COMPANY Minneapolis 15, Minn.426 South 6th Street, Copyright © 1963 by Trevor Robinson All rights reserved Library of Congress Catalog Card No. 63-8920 Printed in the United States of America PREFACE Chemistry is becoming more and more an essential tool for biological investigations. effective manyYet, although the biologist to be in areas of study needs a strong knowledge of chemistry, the kinds of things he needs to know are not necessarily the same things which a chemist needs know.to In many ways the biologist's knowledge of chemistry must be more comprehensive than the chemist's since he is usually unable to choose the workcompounds which he must with. They are presented to him in a bewildering variety. On the other hand, the lifeblood of chemical investigations into natural products is made degradations, proof of structure,up of and synthesis; none of these are usually of much concern to the biologist. What the biologist wants to know is, "What sort of compound is this which haveI found to be involved in such and such a process; from what precursors is it made, and what happens to it later?" The exact structure of a compound down to the location of every double bond and the precise spatial configuration and conformation of the atoms are problems which ultimately must be faced, but by a chemist rather than a biolo- gist. Because of this difference between chemical and biological outlook, the wealth of literature and courses on the chemistry of natural products seldom gives the biologist satisfying answers to his questions, or else delivers these answers with effort and in the midst of much extraneous information. There are multivolume and multiauthor works which direct their discussions of the chemistry of natural products toward biologists, but despite their enormous coverage and depth, even if the individual could afford haveto them all at his fingertips, he would find large gaps and unevenness in the information which they provide. Certain classes of compounds are not adequately described, others are well-treated per se but not contrasted with other types of compounds which they re- semble or which are found in nature along with them. Sometimes detailed and elaborate methods of characterization are given which are essential for laboratories engaged in an intensive investigation of a certain type of compound but which merely frustrate an indi- vidual who just wants to know if he has a of that type. It is for these various reasons, and others, that this book was conceived. It may appear that we have given undue prominence to some relatively unimportant classes of compounds. This has been intentional, and it is an important justification for the book. A reader who desires general information about carbohydrates or amino acids can turn to many excellent sources; but should he want to know something about naturally- occurring lignans or acetylenes, he can at present find no discussion at a level of com- plexity suitable for the interested non-specialist. It should be evident that we have intended to present a book of chemistry rather than biochemistry. Although the metabolic interrelationships of compounds are summa- rized, we have avoided the temptation to discuss the enzymology of these processes or their place in the total picture of plant physiology. Nevertheless, a brief summary of metabolic pathways should be helpful in orientation, and, if one compound has been found, may point the way to finding others that may be associated with it. We have assumed that the reader is familiar with elementary organic and biological chemistry. Many simple concepts which are well covered in general textbooks of these subjects are therefore omitted, assumed, or briefly referred to. While this book has been directed primarily toward botanists and pharmaceutical chemists, perhaps by glancing through it organic chemists with an intensive knowledge of one area or another will be brought to see an immense number of untouched problems -- i await their notice. Certain classes of natural products havewhich received much atten- tion from many chemists; others may be the private province of a single laboratory or ignored.even completely prepared 10Dr. Ernest Sondheimer has Chapter and given valuable advice through- out the rest the manuscriptcommencedwhile Iof the book. Preparation of was a member of the Department of Bacteriology and Botany, Syracuse University, and I am grateful for away from my regular duties which was grantedthe time me to work on it there. Thanks are also due to all my present colleagues and former teachers whose knowledge and en- made this possible;couragement really book to Mrs. Cecile Gitlin and Mrs. Viva Rice whose expert typing and good humor expedited preparation of the manuscript; and finally to my wife and children who were of no help to the book but lots of fun to live with. Trevor Robinson Amherst, Mass. August 19621, 11 ' Hi-' i^t LI3RARY CONTENTS Page Preface 1 Chapter 1. Introduction, 1 2. Carbohydrates, 11 3. Water-soluble organic acids, 36 4. Aromatic compounds, 45 5. Saponifiable lipids, 70 6. Miscellaneous unsaponiftable lipids, 89 7. Volatile alcohols and carbonyl compounds 112 8. Terpenoids and steroids, 117 9. Flavonoids and related compounds, 173 10. Amino acids and proteins, 205 11. Nucleic acids and derivatives, 231 12. Alkaloids, 249 13. Porphyrins, 262 14. Miscellaneous nitrogen and sulfur compounds, 274.... Index 299 81321 ui