Festucine, an alkaloid from tall fescue (Festuca arundinacea Schreb.): Chemistry of the functional groups

Author:

Yates SG,Tookey HL

Abstract

The most abundant alkaloid of tall fescue hay, termed festucine by the authors, was isolated by preparative paper chromatography. The empirical formula of the free base is C8H14N2O, and the molecular weight is 154. One nitrogen of festucine is tertiary, the other secondary. The alkaloid also contains a cyclic ether which can be cleaved by treatment with hydrochloric acid at 160�. The chemical evidence for festucine is consistent with its structural formulation as a positional isomer of loline, a pyrrolizidine alkaloid from the seed of a related grass (Lolium cuneatum Nevski).

Publisher

CSIRO Publishing

Subject

General Chemistry

Cited by 47 articles. 订阅此论文施引文献 订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献

1. Excretion of loline alkaloids in urine and faeces of sheep dosed with meadow fescue (Festuca pratensis) seed containing high concentrations of loline alkaloids;New Zealand Veterinary Journal;2012-05

2. Loline alkaloids: Currencies of mutualism;Phytochemistry;2007-04

3. (1α,6α,7α,7aβ)-2,3,5,6,7,7a-Hexahydro-1,6-epoxy-1H-pyrrolizin-7-ol;Acta Crystallographica Section E Structure Reports Online;2003-08-08

4. Loline Alkaloids;Handbook of Secondary Fungal Metabolites;2003

5. Asymmetric synthesis of (+)-loline, a pyrrolizidine alkaloid from rye grass and tall fescue;Journal of the Chemical Society, Perkin Transactions 1;2001

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