Analytical and sensory differentiation of 1-octen-3-ol enantiomers

Mosandl, Armin; Heusinger, Georg; Gessner, Martin

doi:10.1021/jf00067a033

Cited by 101 publications

(37 citation statements)

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“…2) (Dijkstra and Wiken 1976). The odor of the (−) isoform is said to be mushroom like, instead of the moldy grass note of the (+) form (Mosandl et al 1986). …”

Section: Eight-carbon Volatiles and Fungal Aromamentioning

confidence: 99%

Eight-carbon volatiles in mushrooms and fungi: properties, analysis, and biosynthesis

et al. 2006

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Eight-carbon volatiles are ubiquitous among fungi and characteristic of the fungal aroma. They are the product of the oxidation and cleavage of the fatty acid linoleic acid and are classified as oxylipins, molecules taking part in a wide range of biological processes. Their involvement in the fungal aroma, interactions with pests and pathogens, and reproductive events are reviewed here, as well as the enzymic systems involved in their biosynthesis.

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“…2) (Dijkstra and Wiken 1976). The odor of the (−) isoform is said to be mushroom like, instead of the moldy grass note of the (+) form (Mosandl et al 1986). …”

Section: Eight-carbon Volatiles and Fungal Aromamentioning

confidence: 99%

Eight-carbon volatiles in mushrooms and fungi: properties, analysis, and biosynthesis

et al. 2006

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“…(Table 1) displayed a total of 8 carbon signals composed of one double bond at δ C 141.3 and 114.9, two oxygenated methine carbons at δ C 73.3 and 68.2, three methylene carbons at δ C 39.2, 37.0, and 21.6, and one methyl carbon at δ C 23.7, which were also verified by the analysis of DEPT data. Detailed inspection of the 1 H and 13 C NMR data revealed that the 1 H and 13 C NMR spectra of 1 were quite similar to those of (3R)-oct-1-en-3-ol (2), 10) which was also isolated from this plant, with apparent differences being the signals for an oxygenated methine at δ H 3.83 and δ C 68.2 in 1. The position of replacement was confirmed to be C-2 by the 1 H-1 H COSY correlations of H-1/H-2/H-3 and HMBC correlations of H-1/C-2 and H-1/C-3 (Fig.…”

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confidence: 79%

“…Compound 1 represents only the second natural example of octanediol as one of the aglycones; the first octanediol reported, 7-octene-1,6-diol, was isolated from Aeschynanthus bracteatus. 16) The known compounds were identified as (3R)-oct-1-en-3-ol (2), 10) citroside B (3), 17) (−)-caryophyllene oxide (4), 18) 6β-hydroxystigmast-4-en-3-one (5), 19) 3β-hydroxystigmast-5-en-7-one (6), 19) methyl (9S,12S,13S)-9,12,13-trihydroxy-10E-octadecenoate (7), 20) and methyl (9S,12R,13S)-9,12,13-trihydroxy-10E-octadecenoate (8). 21) All the compounds, except for compound 4, were reported for the first time from this plant.…”

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confidence: 99%

A new aliphatic alcohol and cytotoxic chemical constituents from Acorus gramineus rhizomes

Kim

Kang

Eom

et al. 2015

Bioscience, Biotechnology, and Biochemistry

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A new aliphatic alcohol, (2R,6R)-oct-7-ene-2,6-diol (1), and seven other known compounds (2-8) were isolated from Acorus gramineus rhizomes. The structure of 1 was elucidated by a combination of extensive spectroscopic analyses, including 2D NMR, HR-MS, and the modified Mosher’s method. Compounds 3-8 displayed consistent antiproliferative activities against the cell lines tested with IC50 values ranging from 7 to 48 μm.

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“…Because mushroom alcohol has a chiral carbon, it can exist as two optical isomers or enantiomers: (R)-(-)-1-octen-3-ol and (S)-(? )-1-octen-3-ol [46]. (R)-(-)-1-octen-3-ol exhibits the typical aroma of fresh mushrooms, while (S)-(?…”

Section: Introductionmentioning

confidence: 99%

Effects of Three Volatile Oxylipins on Colony Development in Two Species of Fungi and on Drosophila Larval Metamorphosis

et al. 2015

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The aim of this study is to investigate the effects of three volatile oxylipins on colony development in two fungi and on Drosophila larval metamorphosis. Using an airborne exposure technique, three common and volatile oxylipins (1-octen-3-ol, (E)-2-hexenal, and 1-hexanol) were compared for their effects on spore germination and colony growth in Aspergillus niger and Penicillium chrysogenum, as well as for their effects on the morphogenesis of larvae of Drosophila melanogaster. Conidia of both A. niger and P. chrysogenum plated in the presence of low concentrations (50 ppm) of these three volatile organic compounds (VOCs) formed fewer colony-forming units (CFUs) and exhibited reduced radial growth of colonies as compared to controls. When A. niger and P. chrysogenum spores were germinated in the presence of the enantiomers of 1-octen-3-ol, (R)-(-)-1-octen-3-ol had the greatest impact on colony morphology (decreased sporulation and colony diameter), while (S)-(+)-1-octen-3-ol and the racemic form yielded similar morphological changes but to a lesser extent. In addition, Drosophila larvae exposed to vapors of these oxylipins exhibited serious delays in metamorphosis and toxic effects on pupae and adult stages. Low concentration of these three VOCs can significantly inhibit the formation of CFUs and the growth of fungi. (R)-(-)-1-octen-3-ol imposed the greatest impact on fungal morphology compared to (S)-(+)-1-octen-3-ol and the racemic form. The three volatile oxylipins could also delay the metamorphosis of Drosophila and impose toxic effects on its pupae and adult stages.

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Analytical and sensory differentiation of 1-octen-3-ol enantiomers

Cited by 101 publications

References 1 publication

Eight-carbon volatiles in mushrooms and fungi: properties, analysis, and biosynthesis

Eight-carbon volatiles in mushrooms and fungi: properties, analysis, and biosynthesis

A new aliphatic alcohol and cytotoxic chemical constituents from Acorus gramineus rhizomes

Effects of Three Volatile Oxylipins on Colony Development in Two Species of Fungi and on Drosophila Larval Metamorphosis

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