Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, Vol. 92 (eBook)

A. Douglas Kinghorn, Heinz Falk, Junichi Kobayashi (Herausgeber)

eBook Download: PDF

2010 | 2010
XI, 175 Seiten
Springer Wien (Verlag)
978-3-211-99661-4 (ISBN)

Infos

Resin glycosides are part of a very extensive family of secondary metabolites known as glycolipids or lipo-oligosaccharides and are constituents of complex resins (glycoresins) (1) unique to the morning glory family, Convolvulaceae (2). These active principles are responsible for the drastic purgative action of all the important Convolvulaceous species used in traditional medicine throughout the world since ancient times. Several commercial purgative crude drugs can be prepared from the roots of different species of Mexican morning glories. Their incorporation as therapeutic agents in Europe is an outstanding example of the assimilation of botanical drugs from the Americas as substitutes for traditional Old World remedies (3). Even though phytochemical investigations on the constituents of these drugs were initiated during the second half of the nineteenth century, the structure of their active ingredients still remains poorly known for some examples of these purgative roots. During the last two decades, the higher resolution c- abilities of modern analytical isolation techniques used in conjunction with pow- ful spectroscopic methods have facilitated the elucidation of the active principles of these relevant herbal products. This chapter describes the ethnobotanical information associated with the p- gative morning glory species and how traditional usages were instrumental in plant selection for chemical studies. The advantages and limitations of available analy- cal techniques for the isolation, puri?cation, and structure characterization of the individual constituents of these complex glycoconjugates are also discussed.

Inhalt

Brief CV – Herbert Budzikiewicz 6
Brief CV – Rogelio Pereda-Miranda 7
Brief CV – Daniel Rosas-Rami ´ rez 8
Brief CV – Jhon Castan ˜eda-Go ´mez 9
Contents 10
List of Contributors 12
Microbial Siderophores 13
1. Introduction 14
2. Peptide Siderophores 16
2.1. Pyoverdins and Related Siderophores from Pseudomonas spp. 16
2.2. Azomonas and Azotobacter Siderophores 21
2.3. Anachelin 22
2.4. Actinomycetal Metabolites 23
2.5. Bacterial Hydroxamate Siderophores 24
2.6. Fungal L-Ornithine-Based Hydroxamate Siderophores 24
2.7. Catecholate Siderophores 28
2.8. Lipopeptidic Siderophores 31
2.9. Pseudomonas mendocina Siderophores 35
3. Siderophores Based on Diamino- and Triaminoalkane Skeletons 35
4. Citrate Siderophores 41
4.1. Siderophores with Two Hydroxamic Acid Units 41
4.2. Siderophores with 2-Oxoglutaric Acid Units 44
4.3. Siderophores with Two Catecholate Units 45
4.4. Siderophores with Two Citric Acid Units 46
4.5. Legiobactin 46
5. Pyochelin and Related Structures 47
6. Miscellaneous Siderophores 49
7. Fe2+ Binding Ligands 52
8. Selected Syntheses 53
8.1. Anachelin H ( 10) 53
8.2. Alterobactin ( 26) 54
8.3. Parabactin ( 44) 56
8.4. Nannochelin A 57
8.5. Pyochelin 58
9. Epilog 59
Appendix 60
References 65
Resin Glycosides from the Morning Glory Family 88
1. Introduction 90
2. Ethnobotanical Background and Discovery 90
3. Structural Diversity 93
4. Isolation Techniques 134
5. Structure Elucidation of Resin Glycosides 134
5.1. Degradative Chemical Methods 134
5.2. Spectroscopic Methods 135
5.3. Crystallographic Methods 139
5.4. Molecular Modeling 141
6. Strategies for Synthesis 142
6.1. Tricolorin A 142
6.2. Ipomoeassin E 146
6.3. Woodrosin I 149
7. Significance 149
7.1. Traditional Medicine and Morning Glories 151
7.2. Biological Activities 153
7.3. Pharmacology and Toxicology 156
7.4. Chemical Ecology 157
References 158
Author Index 165
Subject Index 179

Produkt-Details

• Erscheint lt. Verlag: 3.3.2010
• Reihe/Serie: Fortschritte der Chemie organischer Naturstoffe Progress in the Chemistry of Organic Natural Products
• Reihe/Serie: Fortschritte der Chemie organischer Naturstoffe Progress in the Chemistry of Organic Natural Products
• Co-Autor: Herbert Budzikiewicz, Rogelio Pereda-Miranda, Daniel Rosas-Ramírez, Jhon Castañeda-Gómez
• Zusatzinfo: XI, 175 p.
• Verlagsort: Vienna
• Sprache: englisch
• Themenwelt: Medizin / Pharmazie
• Themenwelt: Naturwissenschaften ► Chemie ► Organische Chemie
• Themenwelt: Technik
• Schlagworte: biochemistry • Chemistry • Coumarinolignans • Flavonolignans • non-conventional lignans • picrotoxane • picrotoxin • Polymer • Stilbenolignans
• ISBN-10: 3-211-99661-3 / 3211996613
• ISBN-13: 978-3-211-99661-4 / 9783211996614