| InChI=1S/C15H26O/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,11,16H,5-6,8,10,12H2,1-4H3 |
| CRDAMVZIKSXKFV-UHFFFAOYSA-N |
| [H]C(CO)=C(C)CCC([H])=C(C)CCC=C(C)C |
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plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
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View more via ChEBI Ontology
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3,7,11-trimethyldodeca-2,6,10-trien-1-ol
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3,7,11-trimethyl-2,6,10-dodecatrien-1-ol
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ChemIDplus
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3,7,11-trimethyl-2,6,10-dodecatrienol
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NIST Chemistry WebBook
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Farnesol
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KEGG COMPOUND
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farnesol
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UniProt
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farnesyl alcohol
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NIST Chemistry WebBook
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1763926
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Reaxys Registry Number
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Reaxys
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4602-84-0
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CAS Registry Number
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KEGG COMPOUND
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4602-84-0
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CAS Registry Number
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ChemIDplus
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4602-84-0
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CAS Registry Number
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NIST Chemistry WebBook
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Brasch J, Horter F, Fritsch D, Beck-Jendroschek V, Tröger A, Francke W (2014)
Acyclic sesquiterpenes released by Candida albicans inhibit growth of dermatophytes.
Medical mycology 52, 46-55 [PubMed:23902158]
[show Abstract]
It is unresolved as to whether fungi that share a common skin habitat might in principal interact. In in vitro screening tests with Candida albicans, Trichophytum rubrum and other common dermatophytes, we found C. albicans releases volatile compounds that inhibit growth of the dermatophytes. By applying (enantioselective) gas chromatography combined with mass spectrometry we identified 8 compounds among which stereochemically pure (3R,6E)-2,3-dihydrofarnesol (R-DHF) and (2E,6E)-farnesol (F-ol) were the main components. Synthetic R-DHF and its enantiomer, (3S,6E)-2,3-dihydrofarnesol (S-DHF), as well as F-ol were tested for their capacity to inhibit growth of dermatophytes in microtiter-plate assays over 62 h. All three compounds showed significant and concentration-dependent, to a certain extent even species-specific, inhibitory effects on T. rubrum, T. mentagrophytes, Microsporum canis and Epidermophyton floccosum. In general, S-DHF and F-ol had a pronounced effect on the dermatophytes, similar to or even stronger than that of fluconazole. E. floccosum was completely suppressed by 12.5 μg/ml dihydrofarnesol, as was the inhibition caused by 50 μg/ml fluconazole. Similarly, S-DHF- was more active against T. rubrum than fluconazole. To the best of our knowledge, 2,3-dihydrofarnesol has not yet been described as a volatile generated by microorganisms, and its inhibitory effect on dermatophytes is new to science. However, the relevance of this compound in interfungal interference in situ is unknown. In contrast, farnesol is a well-known semiochemical of C. albicans with intraspecific effects and a clear impact on other microorganisms. Mutual intermicrobial communication based on fungal volatiles therefore appears to be an exciting field for future investigations. | Ibrahim H, Sivasothy Y, Syamsir DR, Nagoor NH, Jamil N, Awang K (2014)
Essential oil composition and antimicrobial activities of two closely related species, Alpinia mutica Roxb. and Alpinia latilabris Ridl., from Peninsular Malaysia.
TheScientificWorldJournal 2014, 430831 [PubMed:24987733]
[show Abstract]
The essential oils obtained by hydrodistillation of the unripe and ripe fruits of Alpinia mutica Roxb. and Alpinia latilabris Ridl. were analysed by capillary GC and GC-MS. The oils were principally monoterpenic in nature. The unripe and ripe fruit oils of A. mutica were characterized by camphor (21.0% and 15.8%), camphene (16.6% and 10.2%), β-pinene (8.6% and 13.5%), and trans,trans-farnesol (8.0% and 11.2%), respectively. The oils of the unripe and ripe fruits were moderately active against Staphylococcus aureus, Bacillus subtilis, Trichophyton mentagrophytes, and Trichophyton rubrum. 1,8-Cineole (34.2% and 35.9%) and β-pinene (20.2% and 19.0%) were the two most abundant components in the unripe and ripe fruit oils of A. latilabris. The oil of the unripe fruits elicits moderate activity against Staphylococcus aureus and Trichophyton mentagrophytes while Candida glabrata was moderately sensitive to the oil of the ripe fruits. | Derengowski LS, De-Souza-Silva C, Braz SV, Mello-De-Sousa TM, Báo SN, Kyaw CM, Silva-Pereira I (2009)
Antimicrobial effect of farnesol, a Candida albicans quorum sensing molecule, on Paracoccidioides brasiliensis growth and morphogenesis.
Annals of clinical microbiology and antimicrobials 8, 13 [PubMed:19402910]
[show Abstract]
BackgroundFarnesol is a sesquiterpene alcohol produced by many organisms, and also found in several essential oils. Its role as a quorum sensing molecule and as a virulence factor of Candida albicans has been well described. Studies revealed that farnesol affect the growth of a number of bacteria and fungi, pointing to a potential role as an antimicrobial agent.MethodsGrowth assays of Paracoccidioides brasiliensis cells incubated in the presence of different concentrations of farnesol were performed by measuring the optical density of the cultures. The viability of fungal cells was determined by MTT assay and by counting the colony forming units, after each farnesol treatment. The effects of farnesol on P. brasiliensis dimorphism were also evaluated by optical microscopy. The ultrastructural morphology of farnesol-treated P. brasiliensis yeast cells was evaluated by transmission and scanning electron microscopy.ResultsIn this study, the effects of farnesol on Paracoccidioides brasiliensis growth and dimorphism were described. Concentrations of this isoprenoid ranging from 25 to 300 microM strongly inhibited P. brasiliensis growth. We have estimated that the MIC of farnesol for P. brasiliensis is 25 microM, while the MLC is around 30 microM. When employing levels which don't compromise cell viability (5 to 15 microM), it was shown that farnesol also affected the morphogenesis of this fungus. We observed about 60% of inhibition in hyphal development following P. brasiliensis yeast cells treatment with 15 microM of farnesol for 48 h. At these farnesol concentrations we also observed a significant hyphal shortening. Electron microscopy experiments showed that, despite of a remaining intact cell wall, P. brasiliensis cells treated with farnesol concentrations above 25 microM exhibited a fully cytoplasmic degeneration.ConclusionOur data indicate that farnesol acts as a potent antimicrobial agent against P. brasiliensis. The fungicide activity of farnesol against this pathogen is probably associated to cytoplasmic degeneration. In concentrations that do not affect fungal viability, farnesol retards the germ-tube formation of P. brasiliensis, suggesting that the morphogenesis of this fungal is controlled by environmental conditions. | Cugini C, Calfee MW, Farrow JM, Morales DK, Pesci EC, Hogan DA (2007)
Farnesol, a common sesquiterpene, inhibits PQS production in Pseudomonas aeruginosa.
Molecular microbiology 65, 896-906 [PubMed:17640272]
[show Abstract]
Farnesol is a sesquiterpene produced by many organisms, including the fungus Candida albicans. Here, we report that the addition of farnesol to cultures of Pseudomonas aeruginosa, an opportunistic human bacterial pathogen, leads to decreased production of the Pseudomonas quinolone signal (PQS) and the PQS-controlled virulence factor, pyocyanin. Within 15 min of farnesol addition, decreased transcript levels of pqsA, the first gene in the PQS biosynthetic operon, were observed. Transcript levels of pqsR (mvfR), which encodes the transcription factor that positively regulates pqsA, were unaffected. An Escherichia coli strain producing PqsR and containing the pqsA promoter fused to lacZ similarly showed that farnesol inhibited PQS-stimulated transcription. Electrophoretic mobility shift assays showed that, like PQS, farnesol stimulated PqsR binding to the pqsA promoter at a previously characterized LysR binding site, suggesting that farnesol promoted a non-productive interaction between PqsR and the pqsA promoter. Growth with C. albicans leads to decreased production of PQS and pyocyanin by P. aeruginosa, suggesting that the amount of farnesol produced by the fungus is sufficient to impact P. aeruginosa PQS signalling. Related isoprenoid compounds, but not other long-chain alcohols, also inhibited PQS production at micromolar concen-trations, suggesting that related compounds may participate in interspecies interactions with P. aeruginosa. |
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