222048-85-3Relevant academic research and scientific papers
Identification and synthesis of volatiles released by the myxobacterium Chondromyces crocatus
Schulz, Stefan,Fuhlendorff, Jens,Reichenbach, Hans
, p. 3863 - 3872 (2004)
Cultures of the myxobacterium Chondromyces crocatus on agar plates were analysed by closed-loop-stripping analysis or solid phase micro extraction. The odour profiles consist mainly of pyrazines, sesquiterpenoids and some aromatic compounds, summing up to more than 50 components. Several new pyrazines as 2-(1-hydroxy-1-methylethyl)-3-methoxypyrazine (9), 2-(1-hydroxy-1-methylpropyl)- 3-methoxypyrazine (10), and 2-(1-hydroxy-2-methylpropyl)-3-methoxypyrazine (11) were identified besides several known pyrazines. A major pyrazine occurring in most samples was 2,5-bis-(1-methylethyl)pyrazine (3). While the well known sesquiterpenoid geosmin (1) was present in low amounts, the related compound (1(10)E,5E)-germacradien-11-ol (21) was identified in most samples in larger quantities. Other prominent sesquiterpenoids not reported before from microorganisms were (6S,10S)-6,10-dimethylbicyclo[4.4.0]dec-1-en-3-one (16), which was accompanied by smaller amounts of several derivatives. The biosynthesis of these compounds is discussed in relation to the recently proposed biosynthetic pathways to 1 and 21.
Identification of host-related volatiles attractive to pineapple beetle Carpophilus humeralis
Zilkowski, Bruce W.,Bartelt, Robert J.,Blumberg, Daniel,James, David G.,Weaver, David K.
, p. 229 - 252 (1999)
Volatiles collected from oranges fed upon by Carpophilus humeralis of either sex were consistently more attractive than volatiles from beetle-free oranges in wind-tunnel bioassays. Three compounds were identified as attractants from this system: 4-ethyl-2-methoxyphenol (1), 2,5- diisopropylpyrazine (2) (a new natural product), and 2-phenylethanol (3). Identifications were confirmed with synthetic compounds that had matching chromatographic and spectral properties. Compounds 1, 2, and 3 had only slight activity alone, but were highly synergistic with each other and with propyl acetate (PA), a fruity ester that is mildly attractive to Carpophilus beetles. Compound 2 was the most active in the wind tunnel; its threshold dose was 0.5 ng when PA was present. The structural specificity for these compounds was high. Twelve phenol analogs of 1 were tested, but only one of these, 2-methoxyphenol, was more attractive than the control. Similarly, the analogs of 2, 2-isopropylpyrazine and 2,6-diisopropylpyrazine, were completely inactive. In the field, a combination of 1, 2, and 3 was not attractive by itself, but it strongly synergized attraction to fermentation volatiles, Carpophilus pheromones, or both. Compounds 1, 2, and 3 apparently have a microbial origin because all three were detected when the host fruit was pineapples instead of oranges, because they could occur in the absence of beetles, and because autoclaved pineapple began to produce the compounds after inoculation from an attractive piece of fruit. The study demonstrated that host location for this generalist species can be far more complex than responding simply to the bouquet of low-molecular-weight volatiles normally associated with fermentation.
