The Isoquinolone Alkaloids

Journal of Natural Products
1982.0

Abstract

Fifteen isoquinolone alkaloids are presently known. They may be found either in the fully aromatic form A, or else in the partially reduced form B. The numbering system is as indicated in expression A. The R substituent on the nitrogen atom may be either hydrogen or methyl, and carbons 6 and 7 usually possess oxygenated substituents. Three dimeric isoquinolone alkaloids are known; these are baluchistanamine (l), revolutinone (9), and punjabine (15). Isoquinolone alkaloids have been found among the Ranunculaceae, Menispermaceae, Berberidaceae, Papaveraceae, Hernandiaceae, Fumariaceae, Lauraceae, and Jlonimiaceae. The alkaloid siamine (ll), found in a leguminaceous plant, has an exceptional oxygenation pattern and also bears a methyl substituent at C-3. It, thus, differs markedly from the other naturally occurring isoquinolones.Isoquinolones may originate in nature from the oxidation of benzylisoquinolines. It is possible, however, that they may also be formed from the in civo oxidation of protoberberines, phthalideisoquinolines, or even spirobenzylisoquinolines. The biogenesis of siamine (11) is clearly different from that of the fourteen other isoquinolone alkaloids.

Knowledge Graph

Similar Paper

The Isoquinolone Alkaloids
Journal of Natural Products 1982.0
Berbidine: A Simple Isoquinoline-Isoquinolone Dimer
Journal of Natural Products 1989.0
Chapter 2 Spirobenzylisoquinoline and Related Alkaloids
The Alkaloids: Chemistry and Pharmacology 1990.0
β-Phenylethylamines and the isoquinoline alkaloids
Natural Product Reports 2002.0
β-Phenylethylamines and the isoquinoline alkaloids
Nat. Prod. Rep. 2004.0
Pakistanine and pakistanamine, two new dimeric isoquinoline alkaloids
Journal of the American Chemical Society 1973.0
Some Dimeric Benzylisoquinoline Alkaloids With an Unusual Oxygenation Pattern
Journal of Natural Products 1983.0
Alcaloïdes des Annonacées
Planta Medica 1983.0
Chapter 5 Quinoline Alkaloids Related to Anthranilic Acid
The Alkaloids: Chemistry and Pharmacology 1988.0
Isoquinoline and isoindole alkaloids from Menispermum dauricum
Phytochemistry 2004.0