Role of the Outer Membrane of<i>Eschericia coli</i>AG100 and<i>Pseudomonas aeruginosa</i>NCTC 6749 and Resistance/Susceptibility to Monoterpenes of Similar Chemical Structure

Griffin, Shane G.; Wyllie, S. Grant; Markham, Julie L.

doi:10.1080/10412905.2001.9712240

Cited by 13 publications

(12 citation statements)

References 24 publications

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“…In previous studies, the outer membrane of gram-negative bacteria (in particular, the lipopolysaccharide layer) was found to be an effective permeability barrier for monoterpenes (10,13). Nevertheless, the P. putida recombinant described in this paper allows production of perillyl alcohol in practical amounts, as demonstrated by the bioreactor experiment (Fig.…”

Section: Discussionmentioning

confidence: 94%

Biocatalytic Production of Perillyl Alcohol from Limonene by Using a Novel Mycobacterium sp. Cytochrome P450 Alkane Hydroxylase Expressed in Pseudomonas putida

Beilen

Holtackers

Lüscher

et al. 2005

Appl Environ Microbiol

159

133

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A number of oxygenated monoterpenes present at low concentrations in plant oils have anticarcinogenic properties. One of the most promising compounds in this respect is (؊)-perillyl alcohol. Since this natural product is present only at low levels in a few plant oils, an alternative, synthetic source is desirable. Screening of 1,800 bacterial strains showed that many alkane degraders were able to specifically hydroxylate L-limonene in the 7 position to produce enantiopure (؊)-perillyl alcohol. The oxygenase responsible for this was purified from the best-performing wild-type strain, Mycobacterium sp. strain HXN-1500. By using N-terminal sequence information, a 6.2-kb ApaI fragment was cloned, which encoded a cytochrome P450, a ferredoxin, and a ferredoxin reductase. The three genes were successfully coexpressed in Pseudomonas putida by using the broad-host-range vector pCom8, and the recombinant converted limonene to perillyl alcohol with a specific activity of 3 U/g (dry weight) of cells. The construct was subsequently used in a 2-liter bioreactor to produce perillyl alcohol on a scale of several grams.The production of (Ϫ)-perillyl alcohol from L-limonene is of interest because of the limited availability of (Ϫ)-perillyl alcohol in nature and its proven anticarcinogenic properties; phase II trials to evaluate perillyl alcohol for the treatment of breast, pancreatic, and colorectal cancer are in progress (37). The only microbial enzyme system described thus far that transforms limonene to perillyl alcohol was found in Bacillus stearothermophilus BR388. However, this enzyme system is not sufficiently regiospecific; significant quantities of carveol, carvone, and terpineol are also produced (25). Removal of these side products is difficult as their boiling points and hydrophobicities are almost identical, and expensive purification methods (for example, chromatography) would be required to obtain sufficiently pure perillyl alcohol. Therefore, the industrial production of perillyl alcohol with this Bacillus enzyme system is not attractive. The conversion of limonene to perillic acid by a Pseudomonas putida strain expressing a cymene monooxygenase was described by Mars et al. (21) and could be interesting as perillyl alcohol is likely to be an intermediate in the production of perillic acid. Other literature concerning limonene biotransformations was reviewed recently (5).The approach that we used to find strains capable of regiospecific hydroxylation of limonene consisted of screening a collection of 1,800 bacterial strains grown on a range of relatively reduced substrates, such as toluene, naphthalene, and various alkanes. Using this approach, we anticipated that we would find oxygenases involved in catabolic pathways that would accept L-limonene as a substrate. Previous work has demonstrated that many catabolic oxygenases accept a wide range of unnatural substrates. Toluene dioxygenases, for example, have been shown to oxygenate more than 100 substrates (reference 11 and references therein). Another example is ...

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Section: Discussionmentioning

confidence: 94%

Biocatalytic Production of Perillyl Alcohol from Limonene by Using a Novel Mycobacterium sp. Cytochrome P450 Alkane Hydroxylase Expressed in Pseudomonas putida

Beilen

Holtackers

Lüscher

et al. 2005

Appl Environ Microbiol

159

133

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“…1995; Karatzas et al . 2000; Griffin et al . 2001), and it is widely used as a flavoring agent, for example for toothpaste and other cosmetics.…”

Section: Discussionmentioning

confidence: 99%

“…and belongs to Group I of compounds able to form a hydrogen bond (Griffin et al 1999). This compound is a constituent of many essential oils; it is known for its antimicrobial activity (Oosterhaven et al 1995;Karatzas et al 2000;Griffin et al 2001), and it is widely used as a flavoring agent, for example for toothpaste and other cosmetics. Carvone seems to be the cause of cheilitis when used at 5% in toothpastes (Francalanci et al 2000) but it is not included in the International Fragrance Research Association (IFRA) list of compounds of established sensitizing potency.…”

Section: Discussionmentioning

confidence: 99%

Preservative properties of Calamintha officinalis essential oil with and without EDTA

Nostro

Cannatelli

Morelli

et al. 2002

Lett Appl Microbiol

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Aims: This study was focused on the preserving properties of Calamintha officinalis essential oil, a plant known for its diaphoretic, expectorant and aromatic properties. Methods and Results: The commercial aerial parts of C. officinalis Moench were hydrodistilled and the essential oil analysed by Gas chromatography/Electron impact mass spectrometry (GC/EIMS) . The inhibition efficacy of this essence, alone (0·5 and 1·0% v/v) and in combination with 2·0 mM EDTA, was assayed, in culture medium and in cetomacrogol cream, using preservative efficacy testing against standard microrganisms (E. coli ATCC 25922, Ps. aeruginosa ATCC 9027, Staph. aureus ATCC 6538P, C. albicans ATCC 10231 and A. niger ATCC 16404). C. officinalis essential oil in cetomacrogol cream with EDTA showed long‐lasting antimicrobial activity, satisfying the European Pharmacopoeia Commission (E. P.) criteria. Conclusion: C. officinalis essential oil could have a potential for a future use as a cosmetic preservative. Impact of the Study: To find natural compounds with antimicrobial activity which could be alternatives to the synthetic chemical preservatives.

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“…17, November/December 2005 as in terpinen-4-ol and α-terpineol can affect the concentration at which K + leakage from E. coli cells is effected. Finally the time frame in which the active terpenes cause signifi cant leakage from E. coli cells is consistent with E. coli cell death rates (12). It is therefore clear that the induced K + leakage by terpenes does play a signifi cant role in their antimicrobial activity against E. coli cells.…”

Section: /Journal Of Essential Oil Researchmentioning

confidence: 78%

“…This data suggests that carvone is able to more effectively permeabilise the E. coli membrane to K + ions than its counterpart carveol. It should be noted that the time frame required for carveol, carvone, α-terpineol and terpinen-4-ol to induce signifi cant K + leakage from E. coli cells is comparable to the time required to induce a 1 log reduction in cell numbers of E. coli by other terpenes of comparable antimicrobial activity (12).…”

Section: Resultsmentioning

confidence: 99%

Antimicrobially Active Terpenes Cause K+ Leakage inE. coliCells

Griffin¹,

Wyllie

Markham

2005

Journal of Essential Oil Research

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The known antimicrobially active oxygenated terpenes, carvone, terpinen-4-ol, α-terpineol, carveol and myrtenol were found to cause signifi cant K + leakage from E. coli cells. In contrast, the relatively inactive oxygenated terpenes, 1,8-cineole and p-menth-6-ene-2,8-diol, did not cause signifi cant K + leakage. Slight structural differences between active terpenes were found to affect the rate of K + leakage from E. coli cells. The membrane permeabilizing effect of the active terpenes is considered a signifi cant factor in their antimicrobial activity.

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Role of the Outer Membrane ofEschericia coliAG100 andPseudomonas aeruginosaNCTC 6749 and Resistance/Susceptibility to Monoterpenes of Similar Chemical Structure

Cited by 13 publications

References 24 publications

Biocatalytic Production of Perillyl Alcohol from Limonene by Using a Novel Mycobacterium sp. Cytochrome P450 Alkane Hydroxylase Expressed in Pseudomonas putida

Biocatalytic Production of Perillyl Alcohol from Limonene by Using a Novel Mycobacterium sp. Cytochrome P450 Alkane Hydroxylase Expressed in Pseudomonas putida

Preservative properties of Calamintha officinalis essential oil with and without EDTA

Antimicrobially Active Terpenes Cause K+ Leakage inE. coliCells

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