Toxicity of Hydrocarbons to Microorganisms

  • Hermann J. Heipieper
  • P. M. Martínez
Reference work entry
Part of the Handbook of Hydrocarbon and Lipid Microbiology book series (HHLM)


Several classes of organic compounds are toxic for living organisms as they accumulate in and disrupt cell membranes. In these cases, the dose-dependent toxicity of a compound correlates with the logarithm of its partition coefficient between octanol and water (logP). Substances with a logP value between 1 and 5 are, in general, toxic for whole cells. Therefore, toxic effects of hydrocarbons on microorganisms can cause problems in bioremediation of highly contaminated sites. The toxic effect of most hydrocarbons is caused by general, nonspecific effects on membrane fluidity due to their accumulation in the lipid bilayer. Only exceptions are hydrocarbons with specific chemically active functional groups such as aldehydes and epoxides that show an additional chemical toxicity.

Most compounds with a higher hydrophobicity than logP of 4 such as e.g., alkanes, PAHs, and biphenyl(s) have very low water solubility, thus their bioavailability is too low to show a toxic effect. By combining the logP value with the water solubility of a compound the maximum membrane concentration (MMC) of a compound can be calculated. By using this parameter it is possible to predict the potential toxicity even of unknown hydrocarbons.


  1. Antunes-Madeira MC, Madeira VMC (1989) Membrane fluidity as affected by the insecticide lindane. Biochim Biophys Acta 982:161–166CrossRefPubMedGoogle Scholar
  2. Aono R, Kobayashi H, Joblin KN, Horikoshi K (1994) Effects of organic solvents on growth of Escherichia coli K–12. Biosci Biotechnol Biochem 58:2009–2014CrossRefGoogle Scholar
  3. Blasco R, Wittich RM, Mallavarapu M, Timmis KN, Pieper DH (1995) From xenobiotic to antibiotic, formation of protoanemonin from 4-chlorocatechol by enzymes of the 3-oxoadipate pathway. J Biol Chem 270:29229–29235CrossRefPubMedGoogle Scholar
  4. Cabral JP (1991) Damage to the cytoplasmic membrane and cell death caused by dodine (dodecylguanidine monoacetate) in Pseudomonas syringae ATCC 12271. Antimicrob Agents Chemother 35:341–344CrossRefPubMedPubMedCentralGoogle Scholar
  5. Cabral MG, Viegas CA, Teixeira MC, Sa-Correia I (2003) Toxicity of chlorinated phenoxyacetic acid herbicides in the experimental eukaryotic model Saccharomyces cerevisiae: role of pH and of growth phase and size of the yeast cell population. Chemosphere 51:47–54CrossRefPubMedGoogle Scholar
  6. Camara B, Herrera C, Gonzalez M, Couve E, Hofer B, Seeger M (2004) From PCBs to highly toxic metabolites by the biphenyl pathway. Environ Microbiol 6:842–850CrossRefPubMedGoogle Scholar
  7. Chen Q, Janssen DB, Witholt B (1995a) Growth on octane alters the membrane lipid fatty acids of Pseudomonas oleovorans due to the induction of alkB and synthesis of octanol. J Bacteriol 177:6894–6901CrossRefPubMedPubMedCentralGoogle Scholar
  8. Chen Q, Nijenhuis A, Preusting H, Dolfing J, Janssen DB, Witholt B (1995b) Effects of octane on the fatty acid composition and transition temperature of Pseudomonas oleovorans membrane lipids during growth in 2-liquid-phase continuous cultures. Enzym Microb Technol 17:647–652CrossRefGoogle Scholar
  9. de Bont JAM (1998) Solvent-tolerant bacteria in biocatalysis. Trends Biotechnol 16:493–499CrossRefGoogle Scholar
  10. Duldhardt I, Nijenhuis I, Schauer F, Heipieper HJ (2007) Anaerobically grown Thauera aromatica, Desulfococcus multivorans, Geobacter sulfurreducens are more sensitive towards organic solvents than aerobic bacteria. Appl Microbiol Biotechnol 77:705–711CrossRefPubMedGoogle Scholar
  11. Ferrante AA, Augliera J, Lewis K, Klibanov AM (1995) Cloning of an organic solvent-resistance gene in Escherichia coli: the unexpected role of alkylhydroperoxide reductase. Proc Natl Acad Sci U S A 92:7617–7621CrossRefPubMedPubMedCentralGoogle Scholar
  12. Heipieper HJ, Keweloh H, Rehm HJ (1991) Influence of phenols on growth and membrane permeability of free and immobilized Escherichia coli. Appl Environ Microbiol 57:1213–1217PubMedPubMedCentralGoogle Scholar
  13. Heipieper HJ, Weber FJ, Sikkema J, Keweloh H, de Bont JAM (1994) Mechanisms behind resistance of whole cells to toxic organic solvents. Trends Biotechnol 12:409–415CrossRefGoogle Scholar
  14. Heipieper HJ, Loffeld B, Keweloh H, de Bont JAM (1995) The cis/trans isomerization of unsaturated fatty acids in Pseudomonas putida S12: an indicator for environmental stress due to organic compounds. Chemosphere 30:1041–1051CrossRefGoogle Scholar
  15. Ingram LO (1977) Changes in lipid composition of Escherichia coli resulting from growth with organic solvents and with food additives. Appl Environ Microbiol 33:1233–1236PubMedPubMedCentralGoogle Scholar
  16. Kabelitz N, Santos PM, Heipieper HJ (2003) Effect of aliphatic alcohols on growth and degree of saturation of membrane lipids in Acinetobacter calcoaceticus. FEMS Microbiol Lett 220:223–227CrossRefPubMedGoogle Scholar
  17. Leon R, Fernandes P, Pinheiro HM, Cabral JMS (1998) Whole-cell biocatalysis in organic media. Enzym Microb Technol 23:483–500CrossRefGoogle Scholar
  18. Liu D, Thomson K, Kaiser KL (1982) Quantitative structure-toxicity relationship of halogenated phenols on bacteria. Bull Environ Contam Toxicol 29:130–136CrossRefPubMedGoogle Scholar
  19. Neumann G et al (2005) Prediction of the adaptability of Pseudomonas putida DOT-T1E to a second phase of a solvent for economically sound two-phase biotransformations. Appl Environ Microbiol 71:6606–6612CrossRefPubMedPubMedCentralGoogle Scholar
  20. Neumann G et al (2006) Energetics and surface properties of Pseudomonas putida DOT-T1E in a two-phase fermentation system with 1-decanol as second phase. Appl Environ Microbiol 72:4232–4238CrossRefPubMedPubMedCentralGoogle Scholar
  21. Saito H, Koyasu J, Shigeoka T, Tomita I (1994) Cytotoxicity of chlorophenols to goldfish GFS cells with the MTT and LDH assays. Toxicol in Vitro 8:1107–1112CrossRefPubMedGoogle Scholar
  22. Salter GJ, Kell DB (1995) Solvent selection for whole cell biotransformations in organic media. Crit Rev Biotechnol 15:139–177CrossRefPubMedGoogle Scholar
  23. Schmid A, Dordick JS, Hauer B, Kiener A, Wubbolts M, Witholt B (2001) Industrial biocatalysis today and tomorrow. Nature 409:258–268CrossRefPubMedGoogle Scholar
  24. Sikkema J, Poolman B, Konings WN, de Bont JA (1992) Effects of the membrane action of tetralin on the functional and structural properties of artificial and bacterial membranes. J Bacteriol 174:2986–2992CrossRefPubMedPubMedCentralGoogle Scholar
  25. Sikkema J, de Bont JA, Poolman B (1994) Interactions of cyclic hydrocarbons with biological membranes. J Biol Chem 269:8022–8028PubMedGoogle Scholar
  26. Sikkema J, de Bont JA, Poolman B (1995) Mechanisms of membrane toxicity of hydrocarbons. Microbiol Rev 59:201–222PubMedPubMedCentralGoogle Scholar
  27. Uribe S, Ramirez J, Pena A (1985) Effects of beta pinene on yeast membrane functions. J Bacteriol 161:1195–1200PubMedPubMedCentralGoogle Scholar
  28. Uribe S, Rangel P, Espinola G, Aguirre G (1990) Effects of cyclohexane, an industrial solvent, on the yeast Saccharomyces cerevisiae and on isolated yeast mitochondria. Appl Environ Microbiol 56:2114–2119PubMedPubMedCentralGoogle Scholar
  29. Weber FJ, de Bont JAM (1996) Adaptation mechanisms of microorganisms to the toxic effects of organic solvents on membranes. Biochim Biophys Acta 1286:225–245CrossRefPubMedGoogle Scholar

Copyright information

© Springer International Publishing AG, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department Environmental BiotechnologyHelmholtz Centre for Environmental Research – UFZLeipzigGermany
  2. 2.Department of BioremediationHelmholtz Centre for Environmental Research—UFZLeipzigGermany

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