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Main description:
The dithiophenes and trithiophenes reviewed in this article are part of a large group of biogenetically related molecules found in plants of the family Compo sitae (Asteraceae). They include compounds having a variable number of unsaturations, particularly double bonds and triple bonds, which occur singly or in combinations. The first report of a naturally occurring trithiophene, ex-terthienyl in the flowers of Tagetes erecta, appeared in 1947 (270); the first naturally occurring dithiophene was isolated from Bidens radiata and described in 1961 (142). The book Naturally Occurring Acetylenes, by BOHLMANN et al. (29), is a superb review of the field up to 1972. Interestingly, out of its more than 500 pages, only two were devoted to physiological and pharmacological aspects. BOHLMANN and ZDERO later contributed one chapter, "Naturally Occurring Thiophenes", to a volume Thiophenes and its Derivatives which appeared in 1985 (57). This chapter presents a survey of such thiophenes based on biogenetic considerations, includes an extensive analysis of the distribution of these compounds, and discusses methods of analysis based on UV, lH-NMR, 13C-NMR, and mass spectra.
The most recent references in the chapter came from publications appearing in 1981. In view of the information on naturally occurring dithiophenes and trithiophenes already available from these sources, this survey emphas- izes the occurrence, the biosynthesis, the synthesis, the photophysical and photochemical properties, and especially the biological properties of these molecules. II.
Contents:
Bacterial Lipids Containing Amino Acids or Peptides Linked by Amide Bonds.- I. Introduction.- II. N-Acylamino Acids.- 1. N-Acyl-l-serine.- 1.1. Serratamolide.- 1.2. Flavolipin.- 2. N-Acyl-l-ornithine.- 2.1. Ornithine-containing Lipid.- 2.2. Cerilipin.- 3. Mass Spectrometry.- 4. Biological Properties.- III. N-Acylpeptides.- 1. N-Acylpeptides with a Linear Peptide Moiety.- 1.1. N-Acyldipeptides: Majusculamides A and B.- 1.2. N-Acyltetrapeptides from Rhodococcus erythropolis.- 1.3. N-Acylpentapeptides from. Mycobacterium paratuberculosis.- 1.4. N-Acyloctapeptide: Stenothricin.- 1.5. N-Acylnonapeptide: Fortuitin.- 1.6. N-Acyldecapeptides: Cerexins.- 1.7. N-Acyltridecapeptides: Tridecapeptins.- 1.8. N-Acylundecapeptide: Amphomycin.- 2. N-Acylpeptides Containing a Hydroxy Fatty Acid Involved in a Lactone Ring.- 2.1. N-Acylpentapeptide: Globomycin.- 2.2. N-Acylheptapeptides: Surfactin, Esperin and Related Compounds.- 2.3. N-Acylheptapeptides: Peptidolipin NA.- 3. N-Acylpeptides with a Lactone Ring not Involving the Hydroxyl Group of a Hydroxy Fatty Acid.- 3.1. N-Acyloctapeptides.- 3.1.1. Lipopeptins.- 3.1.2. Neopeptins.- 3.2. N-Acylnonapeptide: Viscosin.- 3.3. N-Acyldecapeptides: Imacidines.- 3.4. N-Acyltridecapeptides: Antibiotic A21978 C.- 3.5. N-Acyltetradecapeptide: Stendomycin.- 4. Peptidolipids with a Lactam Ring.- 4.1. Iturins.- 4.2. Bacillomycins.- 4.3. Mycosubtilin.- 4.4. General Comments on the Peptidolipids of the Iturin Group.- 4.5. Cyclic Peptides: Octapeptins.- 4.6. Cyclic Peptides: Antibiotic EM 49.- 5. Mass Spectrometry of N-Acylpeptides.- 6. Biological Properties of Peptidolipids.- IV. Glycosides of Peptidolipids.- 1. Glycosides of Peptidolipids Isolated from Rhodococcus erythropolis.- 2. Glycoside of N-Acylnonapeptide: Herbicolin A.- 3. Mycosides C and Related Antigenic Compounds.- 3.1. Apolar Mycosides C.- 3.2. Polar Mycosides C: Antigenic Glycopeptidolipids.- 3.3. Mycosides C as Receptors for Mycobacteriophages.- V. Conclusion.- Acknowledgements.- Addendum.- References.- Naturally Occurring Di- and Trithiophenes.- I. Introduction.- II. Nomenclature.- III. Naturally Occurring Dithiophenes: Structures.- IV. Distribution of Dithiophenes.- V. Naturally Occurring Trithiophenes: Structures.- VI. Distribution of Trithiophenes.- VII. Biosynthesis of Di- and Trithiophenes.- VIII. Synthesis of Di- and Trithiophenes.- IX. Photophysical Studies.- X. Photochemical Reactions.- XI. Biological Reactions.- 1. Effect on DNA.- 2. Antiviral Properties.- 3. Effect on Skin.- 4. Effect on Erythrocytes.- 5. Phototoxicity Toward Bacteria and Fungi.- 6. Nematocidal Activity.- 7. Trithiophenes as Insecticides.- 8. Toxicity Toward Fish and Other Aquatic Organisms.- 9. Toxicity of ?-Terthienyl Toward Plants.- XII. Conclusion.- Acknowledgement.- References.- Author Index.
PRODUCT DETAILS
Publisher: Springer (Springer Verlag GmbH)
Publication date: February, 2012
Pages: 187
Weight: 306g
Availability: Available
Subcategories: Biochemistry, Pharmacology
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