The polyketide folding mode in the biogenesis of isoshinanolone and plumbagin from Ancistrocladus heyneanus (Ancistrocladaceae)

G. Bringmann (Corresponding Author), M. Wohlfarth, Heiko Rischer, M. Rückert, J. Schlauer

Research output: Contribution to journalArticleScientificpeer-review

31 Citations (Scopus)

Abstract

The biosynthetic orgins of the tetralone isoshinanolone and the related naphthoquinone plumbagin were investigated by feeding [13C2]-acetate to suspended callus cultures of Ancistrocladus heyneanus. The orientation of the acetate subunits was elucidated by a similar experiment using [2-13C]-acetate. The polyketide folding mode found for isoshinanolone and plumbagin constitutes a further hint at the acetogenic nature of the naphthylisoquinoline alkaloids, which are typical of A. heyneanus and other species of Ancistrocladaceae and Dioncophyllaceae.

The acetogenic origin and the polyketide folding mode of the naphthoquinone plumbagin (5) and the tetralone isoshinanolone (6) in Ancistrocladus heyneanus were established by feeding of differently 13C-labelled acetate and subsequent 13C NMR analysis.
Original languageEnglish
Pages (from-to)8445-8448
JournalTetrahedron Letters
Volume39
Issue number46
DOIs
Publication statusPublished - 1998
MoE publication typeA1 Journal article-refereed

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Polyketides
Acetates
Tetralones
Naphthoquinones
Dioncophyllaceae
Bony Callus
Alkaloids
Nuclear magnetic resonance
isoshinanolone
plumbagin
Experiments

Cite this

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title = "The polyketide folding mode in the biogenesis of isoshinanolone and plumbagin from Ancistrocladus heyneanus (Ancistrocladaceae)",
abstract = "The biosynthetic orgins of the tetralone isoshinanolone and the related naphthoquinone plumbagin were investigated by feeding [13C2]-acetate to suspended callus cultures of Ancistrocladus heyneanus. The orientation of the acetate subunits was elucidated by a similar experiment using [2-13C]-acetate. The polyketide folding mode found for isoshinanolone and plumbagin constitutes a further hint at the acetogenic nature of the naphthylisoquinoline alkaloids, which are typical of A. heyneanus and other species of Ancistrocladaceae and Dioncophyllaceae.The acetogenic origin and the polyketide folding mode of the naphthoquinone plumbagin (5) and the tetralone isoshinanolone (6) in Ancistrocladus heyneanus were established by feeding of differently 13C-labelled acetate and subsequent 13C NMR analysis.",
author = "G. Bringmann and M. Wohlfarth and Heiko Rischer and M. R{\"u}ckert and J. Schlauer",
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language = "English",
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journal = "Tetrahedron Letters",
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The polyketide folding mode in the biogenesis of isoshinanolone and plumbagin from Ancistrocladus heyneanus (Ancistrocladaceae). / Bringmann, G. (Corresponding Author); Wohlfarth, M.; Rischer, Heiko; Rückert, M.; Schlauer, J.

In: Tetrahedron Letters, Vol. 39, No. 46, 1998, p. 8445-8448.

Research output: Contribution to journalArticleScientificpeer-review

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T1 - The polyketide folding mode in the biogenesis of isoshinanolone and plumbagin from Ancistrocladus heyneanus (Ancistrocladaceae)

AU - Bringmann, G.

AU - Wohlfarth, M.

AU - Rischer, Heiko

AU - Rückert, M.

AU - Schlauer, J.

PY - 1998

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AB - The biosynthetic orgins of the tetralone isoshinanolone and the related naphthoquinone plumbagin were investigated by feeding [13C2]-acetate to suspended callus cultures of Ancistrocladus heyneanus. The orientation of the acetate subunits was elucidated by a similar experiment using [2-13C]-acetate. The polyketide folding mode found for isoshinanolone and plumbagin constitutes a further hint at the acetogenic nature of the naphthylisoquinoline alkaloids, which are typical of A. heyneanus and other species of Ancistrocladaceae and Dioncophyllaceae.The acetogenic origin and the polyketide folding mode of the naphthoquinone plumbagin (5) and the tetralone isoshinanolone (6) in Ancistrocladus heyneanus were established by feeding of differently 13C-labelled acetate and subsequent 13C NMR analysis.

U2 - 10.1016/S0040-4039(98)01935-2

DO - 10.1016/S0040-4039(98)01935-2

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JF - Tetrahedron Letters

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ER -