PubMed · 5722353
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1968-11-22. Gefarnate.. https://pubmed.ncbi.nlm.nih.gov/5722353/
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Effects of the sesquiterpene farnesol (3,7,11-trimethyl-2,6,10-dodecatrien-1-ol) and the sesquiterpene derivative geosmin (1,10-trans-dimethyl-trans-9-decalol) were investigated in a geosmin-producing actinomycete, Streptomyces tendae. Exposure to 300 microM farnesol reduced biomass (fresh matter) accumulation by 97% compared with biomass accumulation by controls, whereas an equal amount of geosmin did not affect biomass accumulation. Increasing exposure to farnesol corresponded with reduced optical density of the culture, reduced levels of geosmin, and reduced metabolic heat production compared with controls, while exogenous geosmin did not affect these parameters. Geosmin dissipated from unioculated medium more rapidly than farnesol, indicating that in addition to the lower toxicity of geosmin, the actual exposure to geosmin over time may be less than exposure to an equal amount of farnesol. Cultures grown on Actinomyces-B medium contained 99.5% less geosmin and were more sensitive to farnesol than those grown on Hickey-Tresner medium, indicating that geosmin synthesis was associated with reduced sensitivity to farnesol. Consumption of farnesyl moieties during geosmin synthesis may reduce the potential for farnesol-induced inhibition of growth and metabolism.
Enzymatic formation of nerolidol was demonstrated by incubation of [14C]farnesyl pyrophosphate with the ultracentrifugal supernatant of cell-free extract of Rhodotorula glutinis. Farnesol was also formed concomitantly with the formation of nerolidol and the ratios of formation of both alcohols were from 1:3 to 1:4. Divalent cation was necessary for the reaction and Mn2+ was much more active than Mg2+ for nerolidol formation. No nerolidol was formed when farnesyl monophosphate or farnesol was used instead of farnesyl pyrophosphate as a substrate. Nerolidyl pyrophosphate or nerolidyl monophosphate could not be detected as an intermediate in the reaction. Based on these observations, nerolidol was presumed to be formed not via nerolidyl pyrophosphate or nerolidyl monophosphate but via a carbonium ion intermediate which was formed by cleavage of the carbon-oxygen bond of farnesyl pyrophosphate. This reaction seems to proceed in a similar manner to the acid hydrolysis of farnesyl pyrophosphate to form nerolidol and farnesol.
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