Biosynthesis of antidesmone in cell cultures of Antidesma membranaceum (Euphorbiaceae): An unprecedented class of glycine-derived alkaloids

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

doi:10.1021/ja001391k

Biosynthesis of antidesmone in cell cultures of Antidesma membranaceum (Euphorbiaceae): An unprecedented class of glycine-derived alkaloids

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

Not published at VTT

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

10 Citations (Scopus)

Abstract

Antidesmone (3), known from several species of Antidesma and Hyeronima (Euphorbiaceae), is a quinoline alkaloid with an unusual substitution pattern. It carries a linear aliphatic side chain that indicates an at least partially acetogenic origin of the carbon skeleton. Feeding experiments with ¹³C and ¹⁵N labeled precursors administered to cell cultures of Antidesma membranaceum yielded antidesmone, which was investigated by NMR spectroscopy. Accordingly, antidesmone is built up from a linear C₁₆-polyketide chain and a C₂ unit derived directly from glycine. It is thus the first representative of a biosynthetically novel class of alkaloids.

Original language	English
Pages (from-to)	9905-9910
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	122
Issue number	41
DOIs	https://doi.org/10.1021/ja001391k
Publication status	Published - 2000
MoE publication type	Not Eligible

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Bringmann, G., Rischer, H., Wohlfarth, M., & Schlauer, J. (2000). Biosynthesis of antidesmone in cell cultures of Antidesma membranaceum (Euphorbiaceae): An unprecedented class of glycine-derived alkaloids. Journal of the American Chemical Society, 122(41), 9905-9910. https://doi.org/10.1021/ja001391k

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abstract = "Antidesmone (3), known from several species of Antidesma and Hyeronima (Euphorbiaceae), is a quinoline alkaloid with an unusual substitution pattern. It carries a linear aliphatic side chain that indicates an at least partially acetogenic origin of the carbon skeleton. Feeding experiments with 13C and 15N labeled precursors administered to cell cultures of Antidesma membranaceum yielded antidesmone, which was investigated by NMR spectroscopy. Accordingly, antidesmone is built up from a linear C16-polyketide chain and a C2 unit derived directly from glycine. It is thus the first representative of a biosynthetically novel class of alkaloids. ",

author = "G. Bringmann and Heiko Rischer and M. Wohlfarth and J. Schlauer",

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doi = "10.1021/ja001391k",

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Biosynthesis of antidesmone in cell cultures of Antidesma membranaceum (Euphorbiaceae) : An unprecedented class of glycine-derived alkaloids. / Bringmann, G. (Corresponding Author); Rischer, Heiko; Wohlfarth, M.; Schlauer, J.

In: Journal of the American Chemical Society, Vol. 122, No. 41, 2000, p. 9905-9910.

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

TY - JOUR

T1 - Biosynthesis of antidesmone in cell cultures of Antidesma membranaceum (Euphorbiaceae)

T2 - An unprecedented class of glycine-derived alkaloids

AU - Bringmann, G.

AU - Rischer, Heiko

AU - Wohlfarth, M.

AU - Schlauer, J.

PY - 2000

Y1 - 2000

N2 - Antidesmone (3), known from several species of Antidesma and Hyeronima (Euphorbiaceae), is a quinoline alkaloid with an unusual substitution pattern. It carries a linear aliphatic side chain that indicates an at least partially acetogenic origin of the carbon skeleton. Feeding experiments with 13C and 15N labeled precursors administered to cell cultures of Antidesma membranaceum yielded antidesmone, which was investigated by NMR spectroscopy. Accordingly, antidesmone is built up from a linear C16-polyketide chain and a C2 unit derived directly from glycine. It is thus the first representative of a biosynthetically novel class of alkaloids.

AB - Antidesmone (3), known from several species of Antidesma and Hyeronima (Euphorbiaceae), is a quinoline alkaloid with an unusual substitution pattern. It carries a linear aliphatic side chain that indicates an at least partially acetogenic origin of the carbon skeleton. Feeding experiments with 13C and 15N labeled precursors administered to cell cultures of Antidesma membranaceum yielded antidesmone, which was investigated by NMR spectroscopy. Accordingly, antidesmone is built up from a linear C16-polyketide chain and a C2 unit derived directly from glycine. It is thus the first representative of a biosynthetically novel class of alkaloids.

U2 - 10.1021/ja001391k

DO - 10.1021/ja001391k

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JF - Journal of the American Chemical Society

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