Table Of ContentNatural Sulfur
Compounds
Novel Biochemical
and Structural Aspects
Natural Sulfur
Compounds
Novel Biochemical
and Structural Aspects
Edited by
Doriano Cavallini
University of Rome
Rome, Italy
Gerald E. Gaull
Institute for Basic Research in Mental Retardation
Staten Island, New York
and
Vincenzo Zappia
University ofN aples
Naples, Italy
Plenum Press • New York and London
Library of Congress Cataloging in Publication Data
International Meeting on Low Molecular Weight Sulfur-Containing Natural Products,
3d, Rome, 1979.
Natural sulfur compounds.
"Proceedings of the Third International Meeting on Low Molecular Weight Sulfur
Containing Natural Products, held in Rome, Italy, June 18-21, 1979."
Includes index.
1. Organosulphur compounds-Physiological effect-Congresses. 2. Sulphur metabo
Iism-Congresses. I. Cava1lini, Doriano. II. Gaull, Gerald E. III. Zappia, Vincenzo.
IV. Title.
QP535.S1IS4 1979 574.19'214 79-28239
ISBN-13:978-1-4613-3047-9 e-ISBN-13:978-1-4613-3045-5
001: 10.1007/978-1-4613-3045-5
Proceedings of the Third International Meeting on Low Molecular Weight Sulfur
Containing Natural Products, held in Rome, Italy, June 18-21, 1979.
© 1980 Plenum Press, New York
Softcover reprint oft he hanlcover 1st edition 1980
A Division of Plenum Publishing Corporation
227 West 17th Street, New York, N.Y. lOOn
All rights reserved
No part of this book may be reproduced, stored in a retrieval system, or transmitted,
in any form or by any means, electronic, mechanical, photocopying, microfilming,
recording, or otherwise, without written permission from the Publisher
Preface
The third International Meeting on "Low Molecular
Weight Sulfur Containing Natural Products,"sponsored by the
International Union of Pure and Applied Chemistry, was
held in the historical building of the Accademia Nazionale
dei Lincei, Rome, Italy, June 18-21, 1979.
The symposium was held in order to exchange knowledge
in the intriguing and complex field of sulfur biochemistry.
This theme brought together scientists from many speciali
zed areas from organic and physical chemistry to biology
and medicine. The interdisciplinary nature of the meeting
gave to the participants the opportunity to discuss pro
blems of common interest approached from different scienti
fic standpoints.
This volume contains 47 contributions presented at
the meeting which mainly deal with new structural and
metabolic aspects of sulfur biochemistry.
An important aspect of such a scientific meeting is
the rapid publication of the proceedings. Through the
cooperation of the authors in providing "camera ready"
copies of their manuscripts, the good efforts of the Orga
nizing Committee, and the Plenum Press Publishing Co., it
has been possible to publish this book within a few months
of the meeting.
Finally, the Editors wish to express their sincere
appreciation to the Accademia dei Lincei for its generous
hospitality. They also gratefully acknowledge the financial
support received from the following Institutions: The Uni
versity of Rome; Consiglio Nazionale delle Ricerche; Ita
lian Society of Biochemistry; Soc. Beckman Analytical,Rome;
Soc. Baldacci, Pisa; Soc. Farmitalia Carlo Erba, Milano;
Soc. Gio De Vita, Rome; Soc.Tecnochimica Moderna, Rome;
Soc. C. Donati, Rome
Doriano Cavallini
Gerald E. Gaull
Vincenzo Zappia
v
Contents
Stereochemical Aspects of Transmethylations
of Potential Biological Interest ••••••••••••••••••.. 1
A.Kjaer, G.Grue-S¢rensen, E.Kelstrup and
J. ¢gaard Madsen
Methylase Mechanisms: Steric Constraints and
Modes of Catalysis ••.•...••••.••••••••.•.••••••.••.• 15
J.K. Coward
Adenosylmethionine as a Precursor for Nucleic
Acids Modification................................... 25
F. Salvatore, C. Traboni, A. Colonna,
G. Ciliberto, G. Paolella, F. Cimino
Involvement of S-Adenosylmethionine in Brain
Phospholipid Metabolism ••••••.••.••••••••.••.••••••. 41
R. Mozzi, V. Andreoli and G. Porcellati
Effect of S-Adenosyl-L-Methionine and
S-Adenosyl-L-Homocysteine Derivatives
on Protein Methylation ••••••.•.••.•.••••••••••••.••.• 55
A. Oliva, P. Galletti, V. Zappia, W.K. Paik
and S. Kim
The Role of S-Adenosylhomocysteine and
S-Adenosylhomocysteine Hydrolase in
the Control of Biological Methylations .•.••.••••.•••. 67
G.L. Cantoni and P.K. Chiang
Homocysteine Biosynthesis in Plants ••..••••.••••••••.•••••.•• 81
J. Giovanelli, S.H. Mudd and A.H. Datko
Inhibition of the Synthesis of Glutathione,
Glutamine and Glutamate by Certain
Methionine Derivatives •••....•.•••••••••••••••••.•••• 93
A. l-1eister
vii
viii CONTENTS
Methionine Metabolism in Developing Neural Tissue •••••••••••••• 107
J.A. Sturman
Antagonists of :Fol.i'c Acid and Vitamin B6 in
Regulation of S-Adenosylmethionine
and S-Adenosylhomocysteine Content
in Normal and Malignant Tissues •••••••••••••••••••••••• 121
Y.V. Bukin and E.N. Orlov
Recent Studies on the Metabolism of
5'-Methylthioadenosine ••••••••••••••••••••••••••••••••• 133
V. Zappia, M. Carteni-:Farina, G. Cacciapuoti
A. Oliva and A. Gambacorta
Two Different Modes of Synthesis and Transformation
of Cysteine (and Related Amino Acids) by
Pyridoxal-P-Dependent Lyases •••••••••••••••••••••••••• 149
A. E. Braunstein and E. V. Goryachencova
Possible Physiological ;Functions of Taurine
in Mammalian Systems •••••••••••••••••••••••••••••••••• 163
J.G. Jacobsen
Cysteine Dioxygenase of Rat Liver: Some Properties
and its Significance on Cysteine Metabolism
of Rat................................................. 175
K. Yamaguchi
Cysteamine Pathway of Taurine Biosynthesis •.•••••••••••.•••••• 187
G. Federici, G. Ricci, L. Santoro, A. Antonucci
and D. Cavallini
Metabolism of Hypotaurine in Some Organs
of the Rat............................................ 195
Y. Pierre, C. Loriette and F. Chatagner
Hypotaurine Oxidation by Mouse Tissues •••••••••••••••••••••••• 201
P. Kontro and S.S. Oja
Sulfur Amino Acids in the Reproductive Tract
of Male Guinea Pigs, Rats,Mice and
Several Marine Animals................................ 213
C.D. Kochakian
Hypotaurine in the Reproductive Tract ••••••••.•••••••••••••••• 225
C.J.G.van der Horst
Taurine in Human Nutrition and Development •••••••••••••••••••• 235
G.E. Gaull and D.K. Rassin
CONTENTS ix
The Effect of Total Parenteral Nutrition on
Taurine. . . . . • • • • • • • • • • • • . • • • • • • • • • • . . • • • . • • • • • • • . . • • •• 245
M.H. Malloy, G.E. Gaull, W.C. Heird and D.K.Rassin
Taurine and Isethionate in Squid Nerve .•••.•....•.••••••.••••• 253
F.C.G. Hoskin and P.K. Noonan
Taurine Biosynthesis in Ox Retina •••••.•••••.••••••••••.•••• 265
S. Macaione, R.M. Di Giorgio, G. De Luca and
G. Nistico
The Regulation and Function of Taurine in the
Heart and Other Organs •••.••••••••••••..•.•.••.•.•.••• 277
R.J. Huxtable
Effects of Ischemia on Taurine Levels •••.•••••••••••••..•••••• 295
J.B. Lombardini
Taurine Effects on Calcium Transport in
Nervous Tissue........................................ 307
H. Pasantes-Morales and A. Gamboa
Taurine in Retinas of Taurine Deficient Cats
and RCS Rats.......................................... 319
S.Y. Schmidt
Thialysine, Thiaisoleucine and Thiaproline as
Inhibitors in Protein Synthesizing
Systems •••.•••••••....•.•••.••...•..•.•.•••••.•••••••• 331
C. De Marco and M. Di Girolamo
Lanthionine Decarboxylation by Animal Tissues •••••••••••.••••• 345
R. scandurra, V. Consalvi, C. De Marco,
L.Politi and D. Cavallini
Sulfur Containing Nuphar Alkaloids .•••••.••••..•••.•••.••••.•• 353
J.T. Wrobel, H. Bielawska, A.Iwanow and
J. Ruszkowska
Biologically Active 1,2-Dithiolane Derivatives from
Mangrove Plants and Related Compounds .•••••••••.•••••• 361
A. Kato and Y.Hashimoto
Biochemical and Clinical Effects of Penicillamine
and Other Thiols Used in the Treatment
of Rheumatoid Arthritis ••••.••••..••.•••••.•••.•••••••• 375
E. Jellum and E. Munthe
x CONTENTS
CYanoepithioalkanes: Some Chemical and
Toxicological Studies •••••••••••••••••••••.•••••••••• 381
J. Luthy and M. Benn
Cysteine and Glutathione in Mammalian
Pigmentation ••••.••••••••.•.•••.••••••••.•••••••••••• 391
G. Prota
Sulfur Compounds in Mustelids .•.••••.•••.•••.••••••••••••••••• 399
K.K.Andersen and D.T. Bernstein
On the Mechanism of C-S Bonds Formation in
the Biosynthesis of Biotin ••••.••.••••••••••••••••••• 407
A. Marquet, A.G.Salib, F. Frappier and
G. Guillerm
'The Biosynthesis of Lipoic Acid in the Rat •••••••••••••••.•••• 413
S. Dupre, G. Spoto, R.M. Matares~M. Orlando
and D. Cavallini
Some Aspects of the Metabolism of Sulfur
Containing Heterocyclic Cofactors:
Lipoic Acid, Biotin, and 8a-(S-L-
cysteinyl) Riboflavin •••••••••••••..••••••••••.•••••.• 423
D.B. McCormick
Implication of Essential Fatty Acids in
Pyruvate Dehydrogenase Activation ••••••. , •• ' .•••.•• , •. 435
J, Raul in , M. Launay, C. Loriette, D. Lapous
and M. Bouchene
Stimulation of Fatty Acid Metabolism by
Panteth (e) ine. • • . • • • • • • • • • • • • • • • • • • . • • • • • • • . • • . . • • • •. 443
K.Kameda and Y. Abiko
Effects of a Hypolipidemic Drug (Clofibrate) on
the Biosynthesis and Degradation of CoA
in Rat Liver ••.••••••••••••••.•••••••••••••••••.••••• 453
S. Skrede
Clinical Chemistry of Mercaptopyruvate and
its Metabolites...................................... 463
B. Sorbo, U. Hannestad, P. Lundquist,
J. Mirtensson and S. Ohman
Spectral Properties of Persulfide Sulfur in
Rhodanese. • • . • • . • • • • • • • • . • • . • • • • • • • • . • • • • • • • • • • • • • . •• 471
C. Cannella, L. Pecci, F. Ascoli, M. Costa,
B. Pensa and D. Cavallini
CONTENTS xi
Biochemistry of Thiocystine ••••••••••••...••..••••••••••.••.••. 483
R. Abdolrasulnia and J.L. Wood
Subcellular compartmentation and Biological
Functions of Mercaptopyruvate
Sulphurtransferase and Rhodanese •••••••••••••••••••••• 493
A. Koj
Semisynthetic Cephalosporins. III. Synthesis
and Structure Activity Relationships
of Novel Orally Active 7-[4-Hydroxy-
3-(Substituted Methyl)Phenylj- ceta
mido-3-Cephem-4-Carboxylic Acids ••••••••••••••••••••• 505
A. Nudelman, A. Patchornick, E.Karoly-Hafely
F. Braun and R.C. Erickson
Ambigui ties in the Enzymology of Sulfur-
Containing Compounds.................................. 511
D. Cavallini, G. Federici, S. Dupre,
C. Cannella and R. Scandurra
Contributors •••••••••••••• 525
A ••••••••••••••••••••••••••••••••••••
Index. • • • • • • • • • • • • • • • • • • • • • • • • • . • • • • • • • • • • • • • • • • • • • • • • • • • • • • • •• 537
Abbreviations
A adenosine
0;
aAA = a aminoacrilate
Acethyl-Coa = acethyl coenzyme A
Acyl-CoA = acyl coenzyme A
ACYS = adenosylcysteine
ACYM = adenosylcysteamine
Ado Hcy = S-adenosylhomocysteine
Ado Met .. S-adenosylmethionine
AEC .. aminoethylcysteine
Ala .. alanine
Alkenyacyl-GPC .. alkenyl-acyl-sn-glycero-3-phosphorylcholine
ALS .. acid labile sulphide
APS = adenosylphosphosulfate
ATP .. adenosine triphosphate
BAL .. 2,3-mercaptoethanol
BSO = buthionine sulfoximine
Bisnor- .. 4,6-dithiohexanoate or l,2-dithiolane-3-propanoate
CBI = covalent binding index
CD - circular dichroism
CD = cysteamine dioxygenase
cis-APD = cis-2,S-bis(aminooxymethyl)-piperazine-3,6-dione
CM - carboxymethyl (cellulose)
CNS = central nervous system
CoA = coenzyme A
COMT = catechol-O-methyl transferase
ConA = concanavalin A
CSA = cysteine sulfinic acid
CSAD = cysteine sulfinic acid decarboxylase
Cycloserine .. 4-aminoisoxazolidone-3
CYM = cysteamine
CYMS03H .. cysteamine sulfonate
Cys .. cysteine
CYSS03H .. cysteine sulfonate
=
Decarboxy Ado-Met S-adenosyl-(Yr3-methylthiopropylamine
DEAE .. diethylaminoethyl (cellulose)
xlii
