Alkaloids: Chemical and Biological Perspectives 13

449 Pages·1999·18.33 MB·English

by  S. William Pelletier (Eds.)

Alkaloids: Chemical
and Biological
Perspectives
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ALKALOIDS: CHEMICAL
AND BIOLOGICAL
PERSPECTIVES
Volume Thirteen
Edited by
S. WILLIAM PELLETIER
Institute for Natural Products Research
and
Department of Chemistry
The University of Georgia, Athens
1999
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Dedicated to
the memory of
Ernst Spath
(1886-1946)
Ernst Spath was bom in Bam, a small village in Austro-Hungarian Europe. After comple-
tion of the doctorate degree (1910), he was on the faculty of Vienna University for over
thirty years where he maintained a large group of research students. He attained a wide
reputation for his researches on the chemistry of plant substances; the study of alkaloids,
was of special interest to Spath.
He made important contributions to the chemistry of alkaloids: the tetrahydroisoquinolines
(papaverine, a-methylnorlaudanosine, anhalidine, anhalonine, carnegine), quinolines
(galipoline, cusparine), aporphines (bulbocarpine, A^-methyllaurotetanin), benzophenan-
thridines (chelidonine, chelerythrine, sanguinarine), amaryllidaceae (tazettine), quino-
lizidine (cytisine), etc. He investigated the pyridine and piperidine alkaloids such as nico-
tine, anabasine, and conhydrine. Spath also worked on other pharmacologiclly important
alkaloids: ephedrine, conessine, mescaline, harmine, harmaline, and calycanthine. Besides
the alkaloids, he explored other classes of natural products such as coumarins, flavonoids,
lignans, and saponins.
Spath had a love for Vienna which he adopted as his home. On September 30, 1946 while
attending the celebration of the Swiss Society of Natural Sciences, he succumbed to a heart
attack and passed away soon after his sixtieth birthday.
B. S. Joshi
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Contributors
Uffe Anthoni, Marine Chemistry Section, Department of Chemistry, University of
Copenhagen, Universitetsparken 5, DK-2100, Copenhagen, DENMARK.
Todd A. Blythe, Vertex Pharmaceuticals, 130 Waverly Street, Cambridge, Massachusetts
02139-4242, U.S.A.
Carsten Christopherson, Marine Chemistry Section, Department of Chemistry, University
of Copenhagen, Universitetsparken 5, DK-2100, Copenhagen, DENMARK.
John W. Daly, Laboratory of Bioorganic Chemistry, National Institutes of Diabetes and
Digestive and Kidney Diseases, National Institutes of Health, Bethesda, Maryland
20892, U.S.A.
Ying Dong, Department of Chemistry and Bamett Institute, Northeastern University, 360
Huntington Avenue, Boston, Massachusetts 02115-5096, U.S.A.
H. Martin Garraffo, Laboratory of Bioorganic Chemistry, National Institutes of Diabetes
and Digestive and Kidney Diseases, National Institutes of Health, Bethesda,
Maryland 20892, U.S.A.
Donna M. lula. Department of Chemistry, State University of New York at Stoney Brook,
Stoney Brook, New York 11794, U.S.A.
Balawant S. Joshi, Institute for Natural Products Research, Chemistry Building, The
University of Georgia, Athens, Georgia 30602-2556, U.S.A.
Philip W. LeQuesne, Department of Chemistry and Barnett Institute, Northeastern
University, 360 Huntington Avenue, Boston, Massachusetts 02115-5096, U.S.A.
Per Half dan Nielson, Marine Chemistry Section, Department of Chemistry, University of
Copenhagen, Universitetsparken 5, DK-2100, Copenhagen, DENMARK.
Iwao Ojima, Department of Chemistry, State University of New York at Stoney Brook,
Stoney Brook, New York 11794, U.S.A.
S. William Pelletier, Institute for Natural Products Research and Department of Chemistry,
The University of Georgia, Athens, Georgia 30602-2556, U.S.A.
Thomas F. Spande, Laboratory of Bioorganic Chemistry, National Institutes of Diabetes
and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, Mary-
land 20892, U.S.A.
This Page Intentionally Left Blank
Preface
Volume 13 of this series presents five timely reviews of research on alkaloids. Chapter 1, by
John W. Daly, H. Martin Garraffo and Thomas F. Spande is a comprehensive update and supple-
ment to the chapter, "Amphibian Alkaloids: Chemistry, Pharmacology, and Biology," written by
Daly and Spande for volume 4 of Alkaloids: Chemical and Biological Perspectives (1986). This
chapter presents newer developments in the chemistry and biology of alkaloids from amphibian
skin. It provides a synopsis and tabulation of the hundreds of alkaloids that have been detected,
with an emphasis on occurrence, structure, dietary origins, and biological activity. Also included
are references to synthetic work that has appeared since the 1986 review.
Chapter 2, by Uffe Anthoni, Carsten Christophersen and Per Halfdan Nielson reviews alka-
loids containing the 1,2, 3, 3a, 8, 8a - hexahydropyrrolo [2,3b] indole ring system and the cy-
clotryptamines. This chapter provides an exhaustive list of available structures. Moreover, the
chemical and biological structures have been evaluated critically so as to identify existing errors and
expose regularities in appearance or biological function. In addition attention is drawn to the pos-
sible implications of the accumulated knowledge related to the synthesis, occurrence, and biochem-
istry of this class of alkaloids.
Chapter 3 by Philip W. Le Quesne, Ying Dong and Todd A. Blythe summarizes recent work
on alkaloids containing the comparatively non - basic pyrrole ring system. Over the past fifteen
years there has been a dramatic increase in the number of pyrrole alkaloids identified. This chapter
treats isolation, structure elucidation, biological activity, and selected chemical syntheses of certain
pyrrole alkaloids.
Chapter 4 by Balawant S. Joshi and S. William Pelletier surveys recent developments in the
chemistry of diterpenoid and norditerpenoid alkaloids occurring in Aconitum, Delphinium and
Consolida genera of the Ranunculaceae family. These plants have been used in tradition Chinese
and Indian medicine as cardiotonics, febrifuges, sedatives, and anti - rheumatics. Because recent
studies have shown that diterpenoid alkaloids are the active constituents responsible for the medici-
nal properties of these plants, great interest in these alkaloids has developed.
Chapter 5 by Iwao Ojima and Donna M. lula focuses on transition metal - catalyzed carbony-
lations as efficient and novel approaches to the construction of piperidine, izidine and quinazoline
alkaloids, which occur in great numbers in nature. Because of their diverse biological activities,
these compounds have attracted the attention of synthetic, medicinal, pharmaceutical, and organic