Ancistrocladus Naphthylisoquinoline Alkaloids

This book describes a unique class of secondary metabolites, the mono- and dimeric-naphthylisoquinoline alkaloids. They exclusively occur in lianas of the palaeotropical Ancistrocladaceae and Dioncophyllaceae plant families. Their unprecedented structures include stereogenic centers and rotationally hindered, and therefore stereogenic, axes. Extended recent investigations on six Ancistrocladus species from Asia, as reported in this contribution, shed light on their fascinating phytochemical productivity, with over 100 intriguing natural products. This high chemodiversity arises from a similarly unique biosynthesis from acetate-malonate units, following a novel polyketidic pathway to plant-derived isoquinoline alkaloids. Some of the compounds show most promising anti-parasitic activities. Additionally, strategies for the regio- and stereoselective total synthesis of the alkaloids, including the directed construction of the chiral axis, are also presented.

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Inhalt

1. Introduction.- 2. Naphthylisoquinoline Alkaloids, a Fascinating Class of Axially Chiral Biaryl Natural Products.- 3. Ancistrocladus, a Genus of Woody Lianas of the Monotypic Plant Family Ancistrocladaceae Widely Occurring in India, Sri Lanka, and Southeast Asia.- 4.The Indian Liana Ancistrocladus heyneanus and Ancistrocladus hamatus from Sri Lanka: Early Studies and More Recent Discoveries.- Full Absolute Stereostructures of Naphthylisoquinoline Alkaloids Directly from Crude Extracts: Characterization of New Metabolites from Ancistrocladus griffithii by the HPLC-MS/MS-NMR-ECD Triad.- 6. Ancistrobenomine A, the First Naphthylisoquinoline Alkaloid with a Hydroxymethylene Function at C-3, and Related 5,1'-Coupled Compounds.- 7. Ancistrocladus cochinchinensis from Central Vietnam, a Distinct Ancistrocladus Taxon? Metabolite Pattern und Phylogenetic Relationship to Ancistrocladus aff. tectorius from China.- 8.Widespread Throughout Southeast Asia: Ancistrocladus tectorius, a Rich Source of Unique, Structurally Most Diverse Mono- and Dimeric Naphthylisoquinoline Alkaloids.- 9. Tables of the Naphthylisoquinoline Alkaloids and Related Compounds Isolated from Asian Ancistrocladus Species.