Geosmin
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| Geosmin | |
|---|---|
| Image:Geosmin minus acsv.svg | |
| General | |
| Systematic name | 4,8a-dimethyldecalin-4a-ol
or 4,8a-dimethyl-decahydronaphthalen-4a-ol |
| Molecular formula | C12H22O |
| SMILES | CC1CCCC2(C1(CCCC2)O)C |
| Molar mass | 182.3 g·mol−1 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
Geosmin, which literally translates to "earth smell", is an organic compound with a distinct earthy flavour and aroma, and is responsible for the earthy taste of beets. The human nose is exquisitely sensitive to geosmin, able to detect it at concentrations down to 5 parts per trillion.
Geosmin is produced by several classes of microbes, including cyanobacteria (blue-green algae) and actinobacteria especially though streptomyces, and released when these microbes die. Communities whose water supply depends on surface water can periodically experience episodes of unpleasant-tasting water when a sharp drop in the population of these bacteria releases geosmin into the local water supply. Under acidic conditions, geosmin decomposes into odorless substances.
Geosmin is also responsible for the muddy smell in bottom-dwelling freshwater fish such as carp and catfish. Blue green algae produce geosmin and methylisoborneol which concentrate in the skin and dark muscle tissue. Geosmin breaks down in acid conditions, and hence vinegar and other acidic ingredients in fish recipes help reduce the muddy flavor.
Recently, the biosynthesis of geosmin by a bifunctional Streptomyces coelicolor enzyme has been unravelled by Jiang et al. (2006, 2007). A single enzyme, the germacradienol/germacrene D Synthase converts farnesyl diphosphate to geosmin in a two steps reaction.
Streptomyces coelicolor is the model representative of a group of soil-dwelling organisms with a complex lifecycle involving mycelial growth and spore formation. Beside the production of volatile geosmin, it also produces many other complex molecules of pharmacological interest and his genome sequence is available at the Sanger Institute.
See also
- Petrichor
- Streptomyces coelicolor
References
- Bear, I.J.; R.G. Thomas (1964). "Nature of argillaceous odour". Nature 201 (4923): 993-995.
- Bear, I.J.; R.G. Thomas (1965). "Petrichor and plant growth". Nature 207 (5005): 1415-1416.
- Jiang, J.; X. He, D.E. Cane (2006). "Geosmin biosynthesis. Streptomyces coelicolor germacradienol/germacrene D Synthase converts farnesyl diphosphate to geosmin". Journal of the American Chemical Society 128 (25): 8128-8129. doi:10.1021/ja062669x. ISSN 0002-7863.
- Jiang, J.; X. He, D.E. Cane (2007). "Biosynthesis of the earthy odorant geosmin by a bifunctional Streptomyces coelicolor enzyme". Nat. Chem. Biol. advanced online publication. doi:10.1038/nchembio.2007.29. ISSN 1552-4469.
- The genome of Streptomyces coelicolor producing geosmin is available at the Sanger Institute: http://www.sanger.ac.uk/Projects/S_coelicolor/de:Geosminja:ジオスミン
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
