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

Research output: Contribution to journalArticleScientificpeer-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 languageEnglish
Pages (from-to)9905-9910
Number of pages6
JournalJournal of the American Chemical Society
Volume122
Issue number41
DOIs
Publication statusPublished - 2000
MoE publication typeNot Eligible

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Euphorbiaceae
Alkaloids
Biosynthesis
Cell culture
Glycine
Amino acids
Cell Culture Techniques
Nuclear magnetic resonance spectroscopy
Polyketides
Substitution reactions
Skeleton
Carbon
Magnetic Resonance Spectroscopy
Experiments
antidesmone

Cite this

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title = "Biosynthesis of antidesmone in cell cultures of Antidesma membranaceum (Euphorbiaceae): An unprecedented class of glycine-derived alkaloids",
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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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 journalArticleScientificpeer-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

M3 - Article

VL - 122

SP - 9905

EP - 9910

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 41

ER -