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

G. Bringmann; M. Wohlfarth; Heiko Rischer; M. Rückert; J. Schlauer

doi:10.1016/S0040-4039(98)01935-2

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

Julius-Maximilians-Universität Würzburg

Research output: Contribution to journal › Article › Scientific › peer-review

36 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 language	English
Pages (from-to)	8445-8448
Journal	Tetrahedron Letters
Volume	39
Issue number	46
DOIs	https://doi.org/10.1016/S0040-4039(98)01935-2
Publication status	Published - 1998
MoE publication type	A1 Journal article-refereed

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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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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

Y1 - 1998

N2 - 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.

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

M3 - Article

SN - 0040-4039

VL - 39

SP - 8445

EP - 8448

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 46

ER -

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

Abstract

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