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The article contains sections titled: 1. Introduction 2. Alkaloids Derived from Polyketides and the Amino Acids Ornithine and Lysine 2.1. Alkaloids Derived by the Insertion of Nitrogen into a Polyketide 2.1.1. ( S )‐(+)‐Coniine, γ‐Coniceine and Related Alkaloids 2.1.2. Solenopsin Family (Fire Ant Alkaloids) 2.1.3. Perhydroazaphenalenes: Defensive Alkaloids of the Coccinellidae 2.1.4. Cyanobacteria Alkaloids 2.1.5. Additional Polyketide‐Derived Alkaloids 2.2. Alkaloids Derived from Ornithine and/or Arginine 2.2.1. Tropane Alkaloids 2.2.2. Pyrrolizidine Alkaloids 2.3. Alkaloids Derived from Ornithine (and/or Arginine) and Nicotinic Acid 2.4. Alkaloids Derived from Lysine (Lys, K) and Nicotinic Acid 2.5. Purine Alkaloids 2.6. Imidazole Alkaloids 2.7. Pepper Alkaloids 3. Alkaloids Derived from the Shikimate Pathway 3.1. Alkaloids Derived from Anthranilate 3.2. Alkaloids Derived from Phenylalanine and Tyrosine 3.2.1. Biosynthesis of Dopamine, Mescaline and Capsaicin 3.2.2. Biosynthesis of Tetrahydroisoquinoline Alkaloids 3.2.3. Cryptostyline (Orchidaceae) and Alkaloids of the Amaryllidaceae 3.2.4. Ephedra Alkaloids 3.3. Alkaloids Derived from Tyrosine 3.4. Alkaloids Derived from Tryptophan and/or Tryptamine (Indole Alkaloids) 3.4.1. Alkaloids Derived from Tryptamine and an Unrearranged Monoterpene Unit 3.4.2. Mold Metabolites 3.4.3. Ergot Alkaloids 3.4.4. Corynantheine–Heteroyohimbine Structural Types 3.4.5. Corynantheine‐Type Alkaloids 3.4.6. Ajmalicine‐Type Alkaloids 3.4.7. Heteroyohimbine Oxindole Type 3.4.8. Glucoalkaloids 3.4.9. Yohimbine–Reserpine Structural Types 3.4.10. Akuammidine–Quebrachidine–Ervatamine–Gelsemine–Akuammiline Structural Types 3.4.11. Uleine–Ellipticine–Vallesamine–Ngouniensine Structural Types 3.5. The Cinchona Structural Type 3.6. The Camptothecin Structural Type 3.7. Terpene, Sesquiterpene, Diterpene and Steroidal Alkaloids (→ ((anchor interlink a26_205.xml Terpenes))) 3.7.1. Overview of Terpenoid Biosynthesis 3.7.2. Monoterpene Alkaloids 3.7.3. Sesquiterpene Alkaloids 3.7.4. Diterpene Alkaloids 3.7.5. Sesterterpene and Triterpene Alkaloids 3.7.6. Steroidal Alkaloids 4. Summary
The article contains sections titled: 1. Introduction 2. Alkaloids Derived from Polyketides and the Amino Acids Ornithine and Lysine 2.1. Alkaloids Derived by the Insertion of Nitrogen into a Polyketide 2.1.1. ( S )‐(+)‐Coniine, γ‐Coniceine and Related Alkaloids 2.1.2. Solenopsin Family (Fire Ant Alkaloids) 2.1.3. Perhydroazaphenalenes: Defensive Alkaloids of the Coccinellidae 2.1.4. Cyanobacteria Alkaloids 2.1.5. Additional Polyketide‐Derived Alkaloids 2.2. Alkaloids Derived from Ornithine and/or Arginine 2.2.1. Tropane Alkaloids 2.2.2. Pyrrolizidine Alkaloids 2.3. Alkaloids Derived from Ornithine (and/or Arginine) and Nicotinic Acid 2.4. Alkaloids Derived from Lysine (Lys, K) and Nicotinic Acid 2.5. Purine Alkaloids 2.6. Imidazole Alkaloids 2.7. Pepper Alkaloids 3. Alkaloids Derived from the Shikimate Pathway 3.1. Alkaloids Derived from Anthranilate 3.2. Alkaloids Derived from Phenylalanine and Tyrosine 3.2.1. Biosynthesis of Dopamine, Mescaline and Capsaicin 3.2.2. Biosynthesis of Tetrahydroisoquinoline Alkaloids 3.2.3. Cryptostyline (Orchidaceae) and Alkaloids of the Amaryllidaceae 3.2.4. Ephedra Alkaloids 3.3. Alkaloids Derived from Tyrosine 3.4. Alkaloids Derived from Tryptophan and/or Tryptamine (Indole Alkaloids) 3.4.1. Alkaloids Derived from Tryptamine and an Unrearranged Monoterpene Unit 3.4.2. Mold Metabolites 3.4.3. Ergot Alkaloids 3.4.4. Corynantheine–Heteroyohimbine Structural Types 3.4.5. Corynantheine‐Type Alkaloids 3.4.6. Ajmalicine‐Type Alkaloids 3.4.7. Heteroyohimbine Oxindole Type 3.4.8. Glucoalkaloids 3.4.9. Yohimbine–Reserpine Structural Types 3.4.10. Akuammidine–Quebrachidine–Ervatamine–Gelsemine–Akuammiline Structural Types 3.4.11. Uleine–Ellipticine–Vallesamine–Ngouniensine Structural Types 3.5. The Cinchona Structural Type 3.6. The Camptothecin Structural Type 3.7. Terpene, Sesquiterpene, Diterpene and Steroidal Alkaloids (→ ((anchor interlink a26_205.xml Terpenes))) 3.7.1. Overview of Terpenoid Biosynthesis 3.7.2. Monoterpene Alkaloids 3.7.3. Sesquiterpene Alkaloids 3.7.4. Diterpene Alkaloids 3.7.5. Sesterterpene and Triterpene Alkaloids 3.7.6. Steroidal Alkaloids 4. Summary
Kopsirachine, an Unusual Alkaloid from the Apocynaeeae Kopsia dasyrachis Ridl. SummaryFrom the leaves of Kopsiu dusyruchis Ridl. a new type of alkaloid, kopsirachine (l), built up from catechin (2) and skytanthine (3) has been isolated. The structure elucidation is based on spectral and chemical evidence. Oxidative cleavage of its derivative 4 with KMnO, afforded veratric acid which was identified as its methylester by comparison with an authentic sample. Pyrolysis of 1 yielded &skytanthine (3). The stereochemistry of the skytanthine substituents in 1 could not yet be established.Aus den Blattern von Kopsiu dasyrachis Ridl. wurden bisher drei Indolalkaloide, Kopsidasin-N-oxid, Kopsidasin und Kopsidasinin isoliert und in ihrer Struktur aufgeklart [2]. In der vorliegenden Mitteilung wird uber die Isolierung und Strukturaufklarung des Hauptalkaloides, Kopsirachin (l), berichtet. Die Verbindung ist aufgebaut aus einem Mol Catechin und zwei Molen Skytanthin.1. Chemische und spektroskopische Befunde. -Kopsirachin (1, M = 6203)) ist amorph und besitzt ein UV-Spektrum [h,,, 281 nm (log& = 3,88), h,,, 256 (3,71)], welches eine grosse Ahnlichkeit mit demjenigen von Catechin (2)4) zeigt. Auch aus dem Vergleich der 'H-und I3C-NMR-Spektren von 1 und 2 lasst sich folgern, dass sich die beiden Chromophore entsprechen; s. unten. Im IR-Spektrum von 1 sind AromatenBanden bei 1620 und 1510 cm-' erkennbar.Im Elektronenstoss-Massenspektrum (EI-MS) von 1 wird das Molekularion nicht registriert, das Ion mit hochster Masse tritt bei m / z 166 (C,,H2,N)5) auf. Es entsteht durch die offenbar bevorzugten Spaltungen der C(
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