Carotenoids Part B: Metabolism, Genetics, and Biosynthesis

504 Pages·1993·8.653 MB·English

by  Lester Packer (Eds.)

Methods in Enzymology
Volume2 14
Carotenoids
Part B
Metabolism, Genetics,a nd Biosynthesis
EDITED BY
Lester Packer
DEPARTkENT OF MOLECULAB AND CELL BIOLOGY
UNNEIWTYOFCALIFORNL4,BERKELEY
BERKELEY, CALJFOBNL4
Editorial Advisory Board
LouiseC anfield Maria A. Livre.a
John E. Hearst JamesA . Olson
Norman Krinsky GeorgeA . Wolf
ACADEMIC PRESS, INC.
EiarcourtB rsceJ ovsnovichP ublishers
San Diego New York Boston
London Sydney Tokyo Toronto
Contributors to Volume 214
elcitrA numbers are in l~entheses following the names of contributors.
Affiliations listed are .tnerruc
GREGORY W. APONTE (3), tnemtrapeD of mann-La Roche, Ltd., CH-4002 Basel,
Nutritional Sciences, University of -rofilaC Switzerland
nia, Berkeley, Berkeley, California 94720 SILLYHP E. NEWOB (1), Department of Nu-
YROGERG A. GNORTSMRA (26), Department trition and Medical Dietetics, University of
of Plant Genetics, Institute for Plant Illinois at Chicago, Chicago, Illinois
Sciences, Swiss Federal Institute of Tech- 60612
nology (ETH), CH-8092 Zarich, Switzer-
PETER M. BRAMLEY (33), Department of
land Biochemistry, Royal Holloway, University
ALAMAYS S. ALAKATHSA (31), Department of Loudon, Surrey TW20 ,XEO England
of Biology, Concordia University, Mon-
TNERB BUCr~ER (27), Division of ,ecneicS
,laert Quebec, Canada H3G 1MS
Northeast Missouri State University,
JAVlER ,~VALOS (25), Departamento de Kirksville, Missouri 63501
,acitbneG Universidad de Sevilla, E-41012
GEORGE S. BULLERJAHN (36), Department
Seville, Spain
of Biological Sciences, Center for Photo-
PAOLO BALLARIO (38), Dipartimento di chemical Sciences, Bowling Green State
Genetica e Biologia Molecolare, Centro di ,ytisrevinU Bowling Green, Ohio 43403
Studio per gli Acidi Nucleici, Universitd di
BILAL CAMARA (32), lnstitut de Biologie
Roma "La Sapienza, "" 00185 Rome, Italy
Mol~culaire des Plantes, Centre National
GLENN E. BARTLEY (34), DuPont Central de la Recherche Scientifique, 1:-67084
Research and Development, Wilmington, ,gruobsartS France
Delaware 19880
ESIUOL M. CANFIELD (10), Department of
REHPOTSIRHC J. BATES (16), Dunn Nutri- Biochemistry, University of Arizona, Tus-
tional Laboratory, Medical Research ,noc Arizona 85721
Council, Cambridge CB4 IX J, England
E. ODEMLO-ADREC (25), Departamento de
EDUARDO R. ONARAJ.FB (25), Departa- ,acit~neG Universidad de St, ,alliv E-41012
mento de Biologia Celular y ,acit~neG Seville, Spain
Universidud de M~laga, E-29071 M~laga,
YLREVEB A. ECNEDIVELC (4), Lipid Nutri-
Spain tion Laboratory, Beltsville Human Nutri-
JOHN S. MARTREB (6), Molecular Oncology tion Research Center, U.S. Department of
Program, Cancer Research Center of ,erutlucirgA Agricultural Research ,ecivreS
Hawaii, University of Hawaii, Honolulu, ,ellivstleB Maryland 20705
Hawaii 96813 RICHARD J. COGDELL (18), Department of
RETEP REYEB (34), Institut f~r Biologie II, Botany, University of Glasgow, Glasgow
Albert Ludwig Universit4t, D-7800 Frei- G12 8QQ, Scotland
,grub Germany TREBOR V. YENOOC (6), Molecular Oncol-
JOHN G. BIERI (4), National Institute of Dia- ogy Program, Cancer Research Center of
betes and Digestive and Kidney Diseases, Hawaii, University of Hawaii, Honolulu,
U.S. Department of Health and Human Hawaii 96813
,secivreS National Institutes of Health, Be- AMECARI M. AD SILVA (35), Departmento de
thesda, Maryland 20892 Engenharia Bioquimica, Universidade
NAFETS BISCHOF (15), Department of Vita- Federal do Rio de Janeiro, Rio de Janeiro
min and Nutrition Research, F. -ffoH 21941, Brazil
ix
X CONTRIBUTORS TO VOLUME 214
A. P. DE REEHNEEL (21), Laboratoria voor cology Program, Cancer Research Center,
Medische Biochemie en voor Klinische An- University of Hawaii, Honolulu, Hawaii
alyse, Universiteit Gent, B-9000 Gent, Bel- 96813
gium AYUZTET KATOH (37), Department of Bo-
SEOROEG T. SDDOD (31), Department of Ag- tany, Faculty of Science, Kyoto University,
ricultural Engineering, Macdonald College Kyoto 606-01, Japan
of McGill University, Ste. Anne-de- NAMRON I. KRINSKY (7), Department of
Bellevue, Quebec, Canada H9X 3V9 Biochemistry, Tufts University School of
NHOJ W. ,NAMDRE JR. (11), Division of Nu- Medicine, Boston, Massachusetts 02111
tritional Sciences, University of Illinois at N1RAK AKSNIPURK (17), Institutf~r Allge-
Urbana-Champaign, Urbana, Illinois meine Botanik, D-2000 Hamburg ,25 Ger-
61801 many
DLORAH B. FAULKNER (13), Faculty of ETTENA ELMUK (34), Institut fftr Biologie II,
Medicine, University of Toronto, Toronto, Albert Ludwig Universitilt, D-7800 Frei-
Ontario, Canada M5S 1A8 burg, Germany
PAUL D. RESARF (33), Department of -DiB M. R. NAMHSKAL (8, 23), Department of
chemistry, Royal Holloway, University of Medicine, George Washington University,
London, Surrey TW20 OEX, England Washington, D.C. 20037
DLORAH C. FURR (14), Department of Nu- NEHPETS W. XUERUOMAL (31), Pharmaceu-
tritional Sciences, University of Connecti- tical Division, Boehringer Manheim,
cut, Storrs, Connecticut 06269 Laval, Quebec, Canada H7V 4A2
RIATSALA T. RENXDRAG (18), Department of BARHOS NAHRABOM (1), Department of
Botany, University of Glasgow, Glasgow Medicine~Gastroenterology, Loyola Uni-
G12 8QQ, Scotland versity Medical Center, Maywood, Illinois
ANNA R. GIULIANO (10), Department of 60153
Family and Community Medicine, Uni- EPPESUIG MACINO (38), Dipartimento di
versity of Arizona, Tuscon, Arizona 85716 Biopatologia Umana, Poh'clinico Umberto
TSNRE GLINZ (15), Department of Pharma- L Universit~ di Roma "'La Sapienza,'"
ceutical Research, F. Hoffmann-La Roche, 00164 Rome, Italy
Ltd., CH-4002 Basel, Switzerland EBEH ILLETRAM (35), Departmento de En-
T. W. NIWDOOG (29), Department of Bio- genharia Bioqulmica, Universidade Fed-
chemistry, University of Liverpool, Liver- eral do Rio de Janeiro, Rio de Janeiro
pool, England 21941, Brazil
CIRE T. GUGGER (11), Department of Food AKINOM B. RENZTAM (10), Arizona Cancer
Science, University of Illinois at Urbana- Center, University of Arizona, Tuscon, Ar-
Champaign, Urbana, Illinois 61801 izona 85724
NHOJ E. TSRAEH (26), Department of Chem- MARC S. MICOZZl (2), National Museum of
istry, University of California, Berkeley, Health and Medicine, Armed Forces Insti-
Berkeley, California 94720 tute of Pathology, Washington, D.C.
SUALCI KCEBMUH 07), Institut raF. Allge- 20306
meine Botanik, D.2000 Hamburg ,25 Ger- UROMAM ORUMIM (37), Nationallnstitutefor
many Basic Biology, Okazaki, Aichi 444, Japan
REDNIPUHB S. ELDNUH (26), Department of OiOROiG ILLEROM (38), Unitd di Nutrizione
Neurology, School of Medicine, University Sperimentale, Istituto Nazionale della Nu-
of California, San Francisco, San Fran- trizione, 00178 Rome, Italy
cisco, California 94110 HPESOJ L. NAPOLI (19), Department of -DiB
T. HPESOJ ,KCOPPAK IV (6), Molecular On- chemistry, School of Medicine and -DiB
CONTRIBUTORS TO VOLUME 214 xi
medical Sciences, State University of New Food Science, North Carolina State Uni-
York at Buffalo, Buffalo, New York 14214 versity, Raleigh, North Carolina 27695
H. J. NELIS (21), Laboratoria voor Medische LEOJ L. ZTRAWHCS (22), Department of Oral
Biochemie en voor Klinische Analyse, Uni- Pathology, Harvard School of Dental Med-
versiteit Gent, B-9000 Gent, Belgium icine, Boston, Massachusetts 02115
MARY ANNE NOSLEN (38), Department of GioROlO SClTA (3), Department of Nutri-
Biology, University of New Mexico, Albu- tional Sciences, University of California,
querque, New Mexico 87131 Berkeley, Berkeley, California 94720
CmTUA OKOH (8, 23), Department of Medi- OLBAP A. SCOLmK (34), DuPont Central
cine, George Washington University, Research and Development Department,
Washington, D.C. 20037 Wilmington, Delaware 19880
SEMAJ A. NOSLO (14), Department of Bio- Louis A. NAMREHS (36), Department of Bio-
chemistry and Biophysics, Iowa State Uni- logical Sciences, Purdue University, West
versity, Ames, Iowa 50011 Lafayette, Indiana 47907
TREBOR S. PARKER (9), Division of Nutri- J. CECIL ,HTIMS JR. (1), Vitamin and Min-
tional Sciences, Cornell University, Ithaca, eral Nutrition Laboratory, Beltsville
New York 14853 Human Nutrition Research Center, U.S.
Department of Agriculture, Agriculture Re-
REHPOTSIRHC L. ROOP (11), Division of Nu-
search Service, Beltsville, Maryland 20705
tritional Sciences, University of Illinois at
Urbana-Champaign, Urbana, Illinois P. SOOLEOROS (21), Laboratory of Aquacul-
61801 ture and Artemia Reference Center, Uni-
Ao lONG (6), Molecular Oncology Program, versity of Gent, B-9000 Gent, Belgium
Cancer Research Center, University of NAIRAM E. DIESDNEWS (12), School of Pub-
Hawaii, Honolulu, Hawaii 96813 lic Health, University of California, Los
K. J. I~DDY (36), Department of Biological Angeles, Los Angeles, California 90024
Sciences, State University of New York at MmIRO TADA (24), Department of Biofunc-
Binghamton, Binghamton, New York tion and Genetic Resources, Faculty of
13902 Agriculture, Okayama University,
DLANOD S. NOSTREBOR (27), Department of Okayama 700, Japan
Zoology and Genetics, Iowa State Univer- AYUMI TANAKA (37), Department of Bo-
sity, Ames, Iowa 50011 tany, Faculty of Science, Kyoto University,
LYREHC L. ROCK (12), Program in Human Kyoto 606-01, Japan
Nutrition, The University of Michigan, NEWONAUG TANG (7), Gastrointestinal Nu-
Ann Arbor, Michigan 48109 trition Laboratory, U.S. Department of
ENHPAD A. EOR (13), Division of Nutritional Agriculture, Human Nutrition Research
Sciences, Cornell University, Ithaca, New Center on Aging, Tufts University, Boston,
York 14853 Massachusetts 02111
GERHARD NNAMDNAS (28, 30), Lehrstuhl JOHN D. ROLYAT (5), Department of Bio-
ft~r Physiologie und Biochemie der Pflan- logical Sciences, Wayne State University,
zen, Universitdt Konstanz, D-7750 Kon- Detroit, Michigan 48202
stanz, Germany T. T. TCHEN (5), Department of Chemistry,
KATHARINA SCHIEDT (15), Department of Wayne State University, Detroit, Michigan
Vitamin and Nutrition Research, F. Hoff- 48202
mann-La Roche, Ltd., CH-4002 Basel,
R. W. NOSEVUT (28), Department of Micro-
Switzerland biology, University of Illinois at Urbana-
DLORAH H. ZTIMHCS (11), Department of Champaign, Urbana, Illinois 61801
xii CONTRIBUTORS TO VOLUME 214
LAURENCE VILLARD-MAcKINTOSH (16), tional Sciences, University of ,ainrofilaC
Department of Public Health and Primary ,yelekreB Berkeley, ainrofilaC 02749
,eraC University of Oxford, Oxford, OX2 SHAN YUAN YANG (20), Department of
6HE, England ,sisehtnysotohP Shanghai Institute of
Plant Physiology, 200032 ShanghaL
WENDY S. WHITE (13), Department of Food
anihC
Science and Human Nutrition, Iowa State
,ytisrevinU Ames, Iowa 11005 SIHUI ZENG (14), Department of -simehcoiB
try and ,scisyhpoiB Iowa State ,ytisrevinU
EORO~IG WOLF (3), Department of Nutri- Ames, Iowa 11005
Preface
Carotenoids are unique pigments synthesized in photosynthetic higher
plants and photosynthetic microorganisms which serve essential functions
in the protection against ringlet oxygen-generated damage by photosensi-
tized reactions. In the plant they participate in fight-harvesting reactions
and may act as a protective covering for certain higher plant species. In
animals, carotenoids have attracted considerable interest, beginning over
fifty years ago when it was discovered that they are precursors for vitamin
A and its derivatives. Mammaliam species do not synthesize carotenoids or
vitamin A. These essential substances are therefore derived solely from
plant carotenoids, which are absorbed and stored in tissues and subse-
quently metabolized.
From a biomedical and biotechnological viewpoint, the carotenoids
have also received considerable attention recently. In numerous epidemio-
logical studies, the dietary intake of foods rich in carotenoids, but not of
preformed vitamin A, has been associated with a reduced risk of some
types of cancer. Chemical studies have shown that the carotenoids are very
powerful quenchers of singlet oxygen and other reactive oxygen species.
Carotenoids, which are considered to be safe and stable, are currently
used primarily as colorants in food products such as margarine. However,
there is increasing interest in their possible role in maintaining health
particularly in regard to lowering the risk of cancer. Many multivitamin
supplements now contain ~.carotene.
In addition to being of widespread biomedical interest, the carotenoids
and their biosynthetic pathways are also being considered as targets for
precise inhibitors that would act as herbm'des.
Studies of the genetics and molecular biology of carotenoids in mi-
crobial photosynthetic systems, or nonphotosynthetic organisms such as
Escherichia coli, are leading to the identification of the gene sequence
homologies and differences between microbial and higher plant systems.
This area of genetics and molecular and cell biology is undergoing rapid
development. It is suspected that carotenoids, or perhaps their metabolic
products, may act as regulators of gene expression.
In addition to research on their natural occurrence, structure, and
biological activity, the distribution of carotenoids in animal and plant
tissues has also been receiving considerable attention.
xiii
xiv ECAFERP
These developments have led to an explosion of activity in this research
area. This volume and its companion, Volume 213 of Methods ni Enzy-
mology, present a comprehensive and state-of-the-art compilation of the
molecular and cellular methodologies needed for pursuing research with
carotenoids.
RETSEL REKCAP
METHODS IN ENZYMOLOGY
EMULOV I. Preparation and Assay of Enzymes
detidE yb YENDIS P. KCIWOLOC DNA NAHTAN O. NALPAK
EMULOV II. Preparation and Assay of Enzymes
detidE yb YENDIS P. KClWOLOC DNA NAHTAN O. NALPAK
EMULOV III. Preparation and Assay of Substrates
detidE yb YENDIS P. KCIWOLOC DNA NAHTAN O. NALPAK
EMULOV IV. Special Techniques for the Enzymologist
detidE yb YENDIS P. KCIWOLOC DNA NAHTAN O. NALPAK
EMULOV V. Preparation and Assay of Enzymes
detidE yb YENDIS P. KCIWOLOC DNA NAHTAN O. NALPAK
EMULOV VI. Preparation and Assay of Enzymes )deunitnoC(
Preparation and Assay of Substrates
Special Techniques
detidE yb YENDIS P. KCIWOLOC DNA NAHTAN O. NALPAK
EMULOV VII. Cumulative Subject Index
detidE yb YENDIS P. KClWOLOC DNA NAHTAN O. NALPAK
EMULOV VIII. Complex Carbohydrates
detidE yb HTEBAZILE F. DLEFUEN DNA ROTCIV GRUBSNIG
EMULOV IX. Carbohydrate Metabolism
detidE yb WILLIS A. WOOD
EMULOV X. Oxidation and Phosphorylation
detidE yb RONALD W. KOORBATSE DNA MAYNARD E, PULLMAN
EMULOV XI. Enzyme Structure
detidE yb C. H. W. SRIH
EMULOV XII. Nucleic Acids (Parts A and B)
detidE yb ECNERWAL NAMSSORG DNA KIVIE EVADLOM
EMULOV XIII. Citric Acid Cycle
detidE yb J. M. NIETSNEWOL
EMULOV XIV. Lipids
detidE yb J. M. NIETSNEWOL
EMULOV XV. Steroids and Terpenoids
detidE yb DNOMYAR B. NOTYALC
EMULOV XVI. Fast Reactions
detidE yb HTENNEK NITSUK
VX
XVi METHODS IN ENZYMOLOGY
EMULOV XVII. Metabolism of Amino Acids and Amines (Parts A and B)
detidE yb TREBREH ROBAT DNA WHITE CELIA ROBAT
EMULOV XVIII. Vitamins and Coenzymes (Parts A, B, and C)
detidE yb DLANOD B. KCIMROCCM DNA LEUMEL n. WRIGHT
EMULOV XIX. Proteolytic Enzymes
detidE yb EDURTREG E. NNAMLREP DNA DNAROL OLZSAL
EMULOV XX. Nucleic Acids and Protein Synthesis (Part C)
detidE yb IOvm EVADLOM DNA ECNERWAL NAMSSORG
EMULOV XXI. Nucleic Acids (Part D)
detidE yb ECNERWAL NAMSSORG DNA KIVIE EVADLOM
EMULOV XXII. Enzyme Purification and Related Techniques
detidE yb B. WILLIAM YBOKAJ
EMULOV XXIII. Photosynthesis (Part A)
detidE yb YNOHTNA NAS PmTRO
EMULOV XXIV. Photosynthesis and Nitrogen Fixation (Part B)
detidE yb YNOHTNA NAS PIETRO
EMULOV XXV. Enzyme Structure (Part B)
detidE yb C. H. W. HIRS DNA EGRES N. FFEHSAMIT
EMULOV XXVI. Enzyme Structure (Part C)
detidE yb C. H. W. HIRS DNA EGRES N. FFEHSAMIT
EMULOV XXVII. Enzyme Structure (Part D)
detidE yb C. H. W. HIRS DNA EGRES N. FFEHSAMIT
EMULOV XXVIII. Complex Carbohydrates (Part B)
detidE yb VICTOR GRUBSNIG
EMULOV XXIX. Nucleic Acids and Protein Synthesis (Part E)
detidE yb NAMSSORG ECNERWAL DNA KIVIE EVADLOM
EMULOV XXX. Nucleic Acids and Protein Synthesis (Part F)
detidE yb KIVIE EVADLOM DNA ECNERWAL NAMSSORG
EMULOV XXXI. Biomembranes (Part A)
detidE yb YENDIS REHCSIELF DNA RETSEL REKCAP
EMULOV XXXII. Biomembranes (Part B)
detidE yb YENDIS REHCSIELF DNA RETSEL REKCAP
EMULOV XXXIII. Cumulative Subject Index Volumes I-XXX
detidE yb MARTHA G. DENNIS DNA DRAWDE A. SINNED
EMULOV XXXIV. Affinity Techniques (Enzyme Purification: Part B)
detidE yb WILLIAM B. YBOKAJ DNA MEre KEHC,.IIW
EMULOV XXXV. Lipids (Part B)
detidE yb JOHN M. NIETSNEWOL
SDOHTEM NI YGOLOMYZNE xvii
EMULOV XXXVI. Hormone Action (Part A: Steroid Hormones)
Edited by BERT W. O'MALLEY DNA JOEL G. NAMDRAH
EMULOV XXXVII. Hormone Action (Part B: Peptide Hormones)
Edited by BERT W. O'MALLEY DNA JOEL G. NAMDRAH
EMULOV XXXVIII. Hormone Action (Part C: Cyclic Nucleotides)
Edited by JOEL G. NAMDRAH DNA BERT W. YELLAM'O
EMULOV XXXIX. Hormone Action (Part D: Isolated Cells, Tissues, and Organ
Systems)
Edited by JOEL G. NAMDRAH DNA BERT W. YELLAM'O
EMULOV XL. Hormone Action (Part E: Nuclear Structure and Function)
Edited by BERT W. O'MALLEY DNA JOEL G. NAMDRAH
EMULOV XLI. Carbohydrate Metabolism (Part B)
Edited by W. A. DOOW
EMULOV XLII. Carbohydrate Metabolism (Part C)
Edited by W. A. DOOW
EMULOV XLIII. Antibiotics
Edited by JOHN H. HSAH
EMULOV XLIV. Immobilized Enzymes
Edited by SUALK HCAaSOM
EMULOV XLV. Proteolytic Enzymes (Part B)
Edited by OLZSAL DNAROL
EMULOV XLVI. Affinity Labeling
Edited by MAILLIW B. YBOKAJ DNA MEIR KEHCLIW
EMULOV XLVII. Enzyme Structure (Part E)
Edited by C. H. W. HIRS DNA EGRES N. FFEHSAMIT
EMULOV XLVIII. Enzyme Structure (Part F)
Edited by C. H. W. HIRS DNA EGRES N. FFEHSAMIT
EMULOV XLIX. Enzyme Structure (Part G)
Edited by C. H. W. HIRS DNA EGRES N. FFEHSAMIT
EMULOV L. Complex Carbohydrates (Part C)
Edited by VICTOR GINSBURG
VOLUME .IL Purine and enidimiryP editoelcuN Metabolism
Edited by AICIRTAP A. EEFFOH DNA MARY NELLE SENOJ
EMULOV LII. Biomembranes (Part C: Biological Oxidations)
Edited by YENDIS REHCSIELF DNA RETSEL REKCAP
EMULOV LIIL Biomembranes (Part D: Biological Oxidations)
Edited by YENDIS REHCSIELF DNA RETSEL REKCAP
EMULOV LIV. Biomembranes (Part E: Biological Oxidations)
Edited by YENDIS REHCSIELF DNA RETSEL REKCAP