Kevin J. Shaw

Agropine: A revised structure

Abstract The product known as agropine from crown-gall tumour is shown to be indistinguishable in all of its properties (physical, chemical, and biological) from N 2 -(1′-deoxy- d -mannitol-l′-yl)- l -glutamine, 1,2′-lactone, a C 11 H 20 N 2 O 7 compound produced by cyclisation of N 2 -(l′-deoxy- d -mannitol-l′-yl)- l -glutamine. Two prior assignments of a C 11 H 17 NO 7 formula obtained by high-resolution electron-impact mass spectrometry have been shown by field-desorption mass spectrometry to correspond to a fragment produced by the rapid loss of ammonia from the parent molecular species.

Corynetoxins causative agents of annual ryegrass toxicity; their identification as tunicamycin group antibiotics

The corynetoxins, formed in galled seeds of Lolium rigidum(annul ryegrass) occupied by Corynebacterium rathayi and responsible for annual ryegrass toxicity, are identified as new members of the tunicamycin group of antibiotics.

Role of Yersinia intermedia and Pseudomonas putida in the development of a fruity off-flavour in pasteurized milk.

Analysis by gas chromatography-mass spectrometry of pasteurized milk with a fruity (pineapple like) off odour and a sour, rancid and soapy taste indicated the presence of concentrations at microg/ml levels of ethyl butanoate, ethyl hexanoate, ethyl octanoate, ethyl decanoate, octanoic acid, decanoic acid and dodecanoic acid. The off-odour and taste were attributed to the presence of these compounds in the milk. Microbiological examination confirmed that the milk was also contaminated with a series of psychrotrophic bacteria including Yersinia intermedia, Pseudomonas putida and Rahnella aquatilis. Growth of isolates of these bacteria in UHT milk at 23 degrees C for 7 d showed that Yer. intermedia produced significant quantities of the C4-C12 alkanoic acids; Ps. putida produced only small quantities of these acids and Rah. aquatilis produced none. In addition, Yer. intermedia and Ps. putida also produced small but significant quantities of the corresponding ethyl esters. In milk inoculated with both Yer. intermedia and Ps. patida, the quantity of ethyl esters produced was greater than that found in cultures containing only one of the isolates. These studies indicated that Yer. intermedia was the principal source of the alkanoic acids in the tainted milk and that the major producer of the corresponding ethyl esters was Ps. patida. This is the first report that Yer. intermedia and Ps. putida can cause an off-odour or taste in dairy products.

Production of trichothecene mycotoxins by Australian Fusarium species

Australian isolates of Fusarium species were grown on potato dextrose agar. Trichothecenes produced by these species were extracted by ethyl acetate followed by methanol and a silica gel column was used to clean-up the extract. The extracted samples were derivatized by acetylation with trifluoroacetic anhydride and the derivatives analysed by gas chromatography/mass spectrometry (GC/MS). Multiple ion detection was used to trace ions characteristic of the trichothecenes expected to be present. Quantitation of those found was based on a known mass of pentabromophenol that was added as an internal standard. Eight species of Fusarium (nineteen strains) were surveyed, of which three species, F. acuminatum, F. equiseti and F. sporotrichioides, produced the trichothecenes scirpentriol, diacetoxyscirpenol, neosolaniol, HT-2 toxin, T-2 toxin, T-2 tetraol and deoxynivalenol. Wheat samples were inoculated with four different species of Fusarium, F. acuminatum, F. equiseti, F. graminearum and F. sporotrichioides, and in these samples diacetoxyscirpenol, neosolaniol, HT-2 toxin and T-2 toxin were found.

Analysis of deoxynivalenol as its trifluoroacetyl ester by gas chromatography-electron ionization mass spectrometry.

Mass spectra of the trifluoroacetyl esters of the trichothecenes deoxynivalenol, diacetoxyscirpenol and T-2 toxin, as well as zearalenone, were obtained by gas chromatography-electron ionization mass spectrometry. Quantitation of deoxynivalenol as its trifluoroacetyl ester by selected ion monitoring was then possible down to 10 pg in the mass spectrometer (equivalent to 1 ng/g in a sample). The method was tested by extracting and analysing mouldy wheat which had previously given a positive result for deoxynivalenol when analysed by thin layer chromatography. The method was also suitable for the analysis of diacetoxyscirpenol and T-2 toxin; however, quantitation of zearalenone was unsuccessful because of the instability of the derivative.