Dioncophylline D and 8-O-Methyldioncophylline D, 7,8′-Coupled naphthylisoquinoline alkaloids from triphyophyllum PELTATUMfn2fn2Part 108 in the series Acetogenic Isoquinoline Alkaloids. For part 107, see Ref. [1].

Phytochemistry
1998.0

Abstract

The isolation and structural elucidation of two novel naphthylisoquinoline alkaloids, dioncophylline D and its 8-O-methyl analogue, from the West African liana Triphyophyllum peltatum are described. Their structures are based on the rare 7,8'-coupling between the two molecular moieties. The absolute configuration at the stereocentres of the isoquinoline half was established by oxidative degradation to give R-3-aminobutyric acid and D-alanine. Both alkaloids are characterized by a rapid rotation around the biaryl axis. The two new alkaloids are apparently found in young (carnivorous) plants, exclusively. (C) 1998 Elsevier Science Ltd. All rights reserved.

Knowledge Graph

Similar Paper

Dioncophylline D and 8-O-Methyldioncophylline D, 7,8′-Coupled naphthylisoquinoline alkaloids from triphyophyllum PELTATUMfn2fn2Part 108 in the series Acetogenic Isoquinoline Alkaloids. For part 107, see Ref. [1].
Phytochemistry 1998.0
Dioncophylline B, a naphthylisoquinoline alkaloid with a new coupling type fromTriphyophyllum peltatum
Phytochemistry 1991.0
Dioncophylline C from the roots of Triphyophyllum peltatum, the first 5,1′-coupled dioncophyllaceae alkaloid
Phytochemistry 1992.0
Dioncophyllinol D, the First 4-Hydroxylated Naphthylisoquinoline Alkaloid, from the Leaves of Triphyophyllum peltatum
HETEROCYCLES 1998.0
(±)-dioncophyllacine A, A naphthylisoquinoline alkaloid with A 4-methoxy substituent from the leaves of Triphyophyllum peltatum
Phytochemistry 1992.0
8-O-Methyldioncophyllinol B and revised structures of other 7, 6′-coupled naphthylisoquinoline alkaloids from Triphyophyllum peltatum (Dioncophyllaceae)
Phytochemistry 2000.0
8-O-Methyldioncophyllinol B and revised structures of other 7, 6′-coupled naphthylisoquinoline alkaloids from Triphyophyllum peltatum (Dioncophyllaceae)
Phytochemistry 2000.0
5′-O-demethyl-8-O-methyl-7-epi-dioncophylline a and its ‘regularly’ configurated atropisomer from Triphyophyllum peltatum
Phytochemistry 1994.0
5′-O-Methyldioncophylline D, a 7,8′-coupled naphthylisoquinoline alkaloid from callus cultures of Triphyophyllum peltatum, and its biosynthesis from a late-stage tetrahydroisoquinoline precursor
Tetrahedron 2016.0
An Unusual 4-Methoxylated Naphthylisoquinolin Alkaloid from the Leaves of<i>Triphyophyllum peltatum</i>
Planta Medica 1991.0