Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

ISBN-13: 9783709187616 / Angielski / Miękka / 2012 / 256 str.

E. Fujita; S. Johne; R. Kasai

Spis treści

Saponins of Ginseng and Related Plants.- I. Introduction.- II. Structure and Chemistry of Dammarane Sapogenins.- 1. Panaxadiol, an Artifact.- 2. Acid Catalyzed Reactions of Dammarane Type Triterpenes and the Genuine Sapogenin of Ginseng.- III. Structures of Ginseng Saponins (1).- 1. Structure of the Prosapogenin Common of Ginsenosides-Rb1, -Rb2, -Rb3, -Rc and-Rd.- 2. Ginsenosides-Rb1, -Rb2, -Rb3, -Rc and -Rd, Saponins of 20(S)-Protopanaxadiol.- 3. Panaxatriol and Ginsenosides-Rf, -Rg1, -Rg2 and 20-Gluco-ginsenoside-Rf (glc-Rf), Saponins of 20(S)-Protopanaxatriol.- IV. Modern Techniques Used in Structure Determination.- 1. Enzymatic Hydrolysis of Glycosides.- 2. 13C-NMR Spectroscopy of Dammarane Type Triterpenes.- 3. Glycosylation Shifts in 13C-NMR Spectra.- 4. Mass Spectrometry.- V. Structures of Ginseng Saponins (2).- 1. Minor Saponins of Ginseng, Ginsenosides-Ra1, -Ra2, -Ra3, and –Rh1.- 2. Saponins of Red Ginseng.- VI. Analysis of Ginseng Saponins.- 1. Quantitative Analysis of Panaxadiol and Panaxatriol.- 2. Separative Analysis of Ginsenosides.- 3. Localization of Saponins in Ginseng Roots.- 4. Seasonal Variation of Ginseng Root Constituents.- VII. Production of Saponins by Tissue Culture.- VIII. Saponins of Other Panax spp..- 1. Saponins of American Ginseng and Dwarf Ginseng.- 2. Saponins of Chinese Sanchi-Ginseng.- 3. Saponins of P. japonicus Rhizomes (Japanese Chikusetsu-Ninjin and Chinese Zhujie-Shen).- 4. Saponins of Rhizomes of P. japonicus var. major (Chinese Zu-Tzi-Shen).- 5. Saponins of P. zingiberensis Rhizomes.- 6. Saponins of Rhizomes of Himalayan Panax, P. pseudo-ginseng subsp. himalaicus.- IX. Saponins of Aerial Parts of Panax spp..- 1. Saponins of P. ginseng Leaves and Flower Buds.- 2. Saponins of Leaves of Himalayan and American Panax spp..- 3. Saponins of Aerial Parts of Chinese Panax spp..- 4. Saponins of Leaves of P. japonicus (Japanese Chikusetsu-Ninjin).- X. Syntheses of Dammarane Sapogenins.- XI. Other Constituents of Ginseng Roots.- 1. Ether-Soluble Compounds.- 2. Carbohydrates.- 3. Nitrogen-Containing Compounds.- XII. Pharmaceutical Studies of Ginseng Saponins.- XIII. Biological Activities of Ginseng.- References.- Diterpenoids of Rabdosia Species.- I. Introduction.- II. Isolation and Structure Determination.- 1. Structure Determination of Enmein in Outline.- 2. Listing of Rabdosia Diterpenoids and Their Sources.- 3. Properties and Reactions Important for Structure Determination.- a) Spectral Aspects and Important Reactions for Ring D Structure Determination.- b) Structure Determination of ent-Kaurane-type Diterpenoids.- c) Structure Determination of ent-6,7-Secokaurane-type Diterpenoids.- d) Structure Determination of ent-8,9-Secokaurane-type Diterpenoids.- e) Structure Determination of ent-7,20-Bonded Kaurane-type Diterpenoids.- f) Structure Determination of an ent-Gibberellane-type Diterpenoid.- III. Chemical Conversions.- 1. Conversion of Rabdosia Diterpenoids to ent-Kaurane and ent-Kaurene.- 2. Conversion of Enmein to ent-Abietane.- 3. Conversion of Enmein and Trichokaurin to Aconite Alkaloids.- 4. Conversion of Enmein into Gibberellins.- 5. Interconversions among Rabdosia Diterpenoids.- a) Biogenetic-type Conversion (Kaurene type ? 6,7-Secokaurene-type).- b) Retrobiogenetic-type Conversions.- 6. Other Topics.- a) Stereochemistry of Ring D in Enmein Derivatives.- b) Hypoiodite Reaction of Enmein Derivatives.- c) Isolation of Dihydroenmein and Its Conversion to Enmein.- IV. Total Synthesis of Enmein.- V. Biosynthesis.- VI. Physiological Activity.- 1. Antibacterial Activity.- 2. Antitumor Activity.- 3. Insect Growth Inhibitory Activity.- 4. Bitterness.- References.- The Quinazoline Alkaloids.- I. Introduction.- II. Simple Substituted Quinazolin-4-ones.- 1. General Characteristics.- 2. Arborine.- 3. Glycorine.- 4. Glycosmicine.- 5. Glycosminine.- 6. Glycophymoline.- 7. Pegamine.- 8. Quinazolines of Zanthoxylum arborescens.- 9. Febrifugine and Isofebrifugine.- III. The Pyrroloquinazolines.- 1. Vasicine (Peganine), Vasicinone, 7-Hydroxypeganine, Vasicinolone, Vasicol, Nordine and Deoxyvasicinone.- 2. Anisotine, Anisessine, Aniflorine, Deoxyaniflorine and Sessiflorine.- 3. Vasicoline, Vasicolinone and Adhatodine.- 4. Peganidine, Isopeganidine, Deoxypeganidine, Dipegine and Peganol.- IV. The Pyridoquinazolines.- V. The Indolopyridoquinazolines.- 1. Rutaecarpine and Related Alkaloids.- 2. Evodiamine and Dehydroevodiamine.- 3. Hortiamine and Hortiacine.- 4. Euxylophorine A—D; Euxylophoricine A—F.- 5. Paraensine.- VI. Quinazolines Produced by Microorganisms.- 1. Tryptanthrin.- 2. Quinazolines of Pseudomonas Species.- 3. Quinazolines of Aspergillus Species.- 4. Quinazolines of Streptomyces.- 5. Chrysogine.- VII. Quinazolines Found in Animals.- 1. Glomerin and Homoglomerin.- 2. Tetrodotoxin.- VIII. Biosynthesis.- 1. Pyrroloquinazolines.- 2. Arborine and Glomerin.- 3. Indolopyridoquinazolines.- 4. Fungal Metabolites.- IX. Biological Activity of Natural and Synthetic Quinazolines.- Acknowledgement.- References.- Author Index.