WO2012014244A1 - Utilisation de terpinèn-4-ol en tant qu'agent antimicrobien contre des bactéries du genre legionella - Google Patents

Utilisation de terpinèn-4-ol en tant qu'agent antimicrobien contre des bactéries du genre legionella Download PDF

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Publication number
WO2012014244A1
WO2012014244A1 PCT/IT2011/000267 IT2011000267W WO2012014244A1 WO 2012014244 A1 WO2012014244 A1 WO 2012014244A1 IT 2011000267 W IT2011000267 W IT 2011000267W WO 2012014244 A1 WO2012014244 A1 WO 2012014244A1
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Prior art keywords
terpinen
systems
legionella
use according
pneumophila
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PCT/IT2011/000267
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English (en)
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Francesca Mondello
Maria Luisa Ricci
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Istituto Superiore Di Sanita'
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
    • A61L2/16—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using chemical substances
    • A61L2/18—Liquid substances or solutions comprising solids or dissolved gases
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/06—Oxygen or sulfur directly attached to a cycloaliphatic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/08—Magnoliopsida [dicotyledons]
    • A01N65/28—Myrtaceae [Myrtle family], e.g. teatree or clove
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
    • A61L2/16—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using chemical substances
    • A61L2/20—Gaseous substances, e.g. vapours
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/50—Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2307/00—Location of water treatment or water treatment device
    • C02F2307/14—Treatment of water in water supply networks, e.g. to prevent bacterial growth

Definitions

  • the present invention refers to the use of terpinen-4-ol as antimicrobial agent against bacteria of Legionella genus.
  • the present invention concerns the use of terpinen-4-ol, both in aqueous solutions and vapour form, as antimicrobial agent against bacteria of Legionella genus, preferably L. pneumophila, for disinfecting systems for the distribution of or containing water such as building water distribution systems, cooling towers, spas, small waterlines such as dental unit, medical devices present in hospital and health care facilities or respiratory medical devices from the above bacteria.
  • L. pneumophila is the causative agent of two clinical syndromes in humans: a severe pneumonia called Legionnaires' disease (6) and Pontiac fever, a self-limited flu-like illness (7).
  • Legionella is ubiquitous in freshwater environment where it survives as intracellular parasite of free- living protozoa and could be associated with biofilms (8,9).
  • the infection occurs through inhalation or aspiration of Legionella contaminated aerosols, followed by replication in lung alveolar macrophages.
  • the disease arises by the ability of bacteria to replicate inside the phagosome and to escape from lysosomal degradation (10,11).
  • Legionella species are the causative agent of about 1.9% of all community-acquired pneumonia cases, 4.9% of those hospitalized, and in 7.9% of those requiring admission to intensive care units (12).
  • Outbreaks of legionellosis have been mostly associated to artificial contaminated environments such as building water distribution systems, cooling towers, spas, and similar. Water distribution systems and aerosol-producing medical devices are main sources of health care-associated legionellosis (13, 14).
  • TTO Australian tea tree oil
  • terpinen-4-ol the main component of TTO, against Legionella pneumophila are lacking, probably also due to the difficulties encountered in standardizing susceptibility methods for this fastidious-to-grow microorganism.
  • the EOs and components constitute an interesting category of compounds endowed with broad spectrum antimicrobial activity (21 , 22, 23).
  • the terpinen-4-ol (trade names/synonyms: (+/-)-4- terpineol; (+/-)-p- menth-1-en-4-ol; (+/-)-para-menth-1-en-4-ol; (+/-)-terpinen-4-ol; 1-terpinen- 4-ol; 1-para-menthen-4-ol; 3-cyclohexen-1-ol, 4-methyl-1-(1-methylethyl)-; 4-carvomenthenol; 4-carvomenthenol, natural; 4-methyl-1-(1-methylethyl)- 3-cyclohexen-1-ol; 4-methyl-1-isopropyl-3-cyclohexen-1-ol; 4-terpinenol; 4- terpineol; dl-4-terpineol; menth-1-en-4-ol; para-menth-1-en-4-ol; p-menth- 1-en-4-ol; terpineno
  • Terpinen-4-ol is available commercially from the producers Acros Organics BVBA, Geel, Belgium, catalogue number 360020000, 360020250, 36002100097%, from Hangzhou Standard Chemical Co., Ltd. China, from Sanmenxia Xiawei Chemical Co., Ltd. China and from Takasago International Corporation, Japan 2906.14.0000 C020007.
  • Terpinen-4-ol may be produced by synthesis or extracted by fractional distillation of essential oil of Melaleuca alternifolia Cheel (MelaleucolTM, from BGR CORPORATION PTY LTD., Level 6, 130 Phillip Street Sydney WALES 2000) or other species of the genus Melaleuca (Myrtaceae), or Leptospermum, Origanum, Cupressus, Chamaecyparis, Juniperus, Elettaria, Myristica, Thymus.
  • the present invention concerns the determination of the in vitro activity of terpinen-4-ol against various L. pneumophila serogroups (SG), from different sources (stock cultures, environment, clinical) by using two different methods: the Clinical and Laboratory Standards Institute (CLSI) broth micro-dilution method (26) with slight modifications, and the micro-atmosphere diffusion method (27,28). Furthermore, the conditions of the assay have been improved by careful consideration of oil activity in aqueous phase and preventing evaporation by microplate sealing.
  • CLSI Clinical and Laboratory Standards Institute
  • terpinen-4-ol the main component of tea tree oil (TTO)
  • TTO tea tree oil
  • pneumophila is sensitive to terpinen-4-ol, with minimal inhibitory concentration (MIC) ranging from 0.06 to 0.125 % v/v, and a bactericidal activity at 0.5% v/v.
  • MIC inhibitory concentration
  • terpinen-4-ol vapours exerted critical activity and its action must be controlled for reproducible MIC determination.
  • increasing the temperature of the assay to 40°C and, particularly, 45°C causes a major increase of terpinen-4-ol an ⁇ -Legionella activity compared to the TTO activity suggesting that terpinen-4-ol could be particularly useful in the combination with high temperature in the eradication of Legionella.
  • terpinen-4-ol is active as L pneumophila disinfectant for a possible control measure for Legionella water system contamination, especially in spas, in small waterlines or in particular respiratory medical devices. They also indicate a superior advantage of terpinen-4-ol as Legionella disinfectant at temperature in the range of 40-45°C.
  • two different assay methods have been compared for the assessment of the antimicrobial activity of terpinen- 4-ol against L. pneumophila, possibly also applying to other EOs, particular to the mother mixture TTO.
  • These conditions particularly considered the potential effects of the diffusion of oil vapours in aqueous phase and preventing evaporation by plate sealing.
  • vapour effects of EOs were examined in aqueous phase under plate sealing only to determine the antifungal activity and never for antibacterial activity.
  • a simple but quite effective sealing procedure in the micro-dilution method to determine the antibacterial activity of terpinen-4-ol against L. pneumophila in aqueous phase was evaluated for the first time.
  • TTO vapours which have been shown to be growth-inhibitory against Staphylococcus aureus (40), were lost during incubation.
  • the oil evaporation caused remarkable inconsistencies in antimicrobial effects, with apparently very low MIC values, and rendered somehow ephemeral and irreproducible the exact quantitative determination of the inhibitory effects.
  • the oil vapours were entrapped between the microplate and its lid causing a non-homogeneous distribution of oil concentration in the microplate wells.
  • the present invention shows that L. pneumophila, quite irrespective of serogroup and source of isolation, is extraordinarly sensitive to terpinen-4-ol, a main compound of the TTO mixture, the effect is bactericidal, particularly in the temperature range of 40-45°C.
  • terpinen-4-ol vapour exerts critical activity and its action must be controlled for reproducible MIC determination.
  • TTO contains multiple components, each with individual properties, it would more practical to make a formulation containing a single active ingredient as potential alternative agent for control of Legionella infections.
  • terpinen-4-ol as antimicrobial agent against bacteria of Legionella genus, preferably L. pneumophila and other Legionella species such as L. micdadei.L. bozemanii, L. longbeachae, L. gormanii, L. rubrilucens, L. dumoffii.
  • terpinen-4-ol is intended pure terpinen-4-ol extracted from natural sources (i.e. terpinen-4-ol concentration >97%), as mentioned above, or produced by synthesis.
  • Terpinen-4-ol according to the present invention is not TTO.
  • terpinen-4-ol is used particularly for disinfecting systems for distribution of or containing water such as, but not limited to, building water distribution systems, cooling towers, spas, small waterlines, such as dental units, respiratory medical devices present in hospital and health care facilities or other medical devices where contact with L.pneumophila contaminated water can occur.
  • water such as, but not limited to, building water distribution systems, cooling towers, spas, small waterlines, such as dental units, respiratory medical devices present in hospital and health care facilities or other medical devices where contact with L.pneumophila contaminated water can occur.
  • terpinen-4-ol is used particularly for disinfecting systems for distribution of or containing water such as, but not limited to, building water distribution systems, cooling towers, spas, small waterlines, such as dental units, respiratory medical devices present in hospital and health care facilities or other medical devices where contact with L.pneumophila contaminated water can occur.
  • air conditioning systems like humidifiers, nebulizers, spray systems, heat pumps;
  • the emergency water systems such as decontamination showers, eye washing stations and the sprinkler anti-fire systems;
  • terpinen-4-ol can be used in form of aqueous solution or vapour.
  • Terpinen-4-ol in form of aqueous solution or vapour is preferably used at a temperature ranging from 40°C to 60°C, preferably from 40°C to 50°C, more preferably from 40°C to 45°C.
  • the concentration of terpinen-4-ol in aqueous solution can be from 0,001 % v/v, preferably from 0,01% v/v, more preferably from 0,02% v/v to 0,125 % v/v.
  • the solution can be used directly on the surfaces of the above systems or terpinen-4-ol can be dissolved in water circulating or contained in the above systems so that to obtain the above suitable concentrations depending on temperature.
  • terpinen-4-ol concentrations can be used, for instance 5% v/v.
  • L. pneumophila strains from stock collection, clinical and environmental isolate were tested. They included: L pneumophila SG 1 (Lp 1) ATCC 33152, L. pneumophila SG 6 (Lp 6) ATCC 33215, 5 Lp1 clinical isolates, 5 Lp1 environmental isolates, 5 Lp6 clinical isolates and 1 Lp6 environmental isolates. All strains were stored at -70 °C in sterile skimmed milk until use. Subculture of frozen bacteria were grown on buffered charcoal yeast extract agar supplemented with 0.1% alpha- ketoglutarate (BCYE-a, Oxoid, LTD, Basingstoke, England). Plates were incubated at 36 ⁇ 1 °C in humidified air with 2.5% CO 2 for 72 h. E.coli ATCC 25922 was used as quality control.
  • the micro-dilution test for L. pneumophila and for quality control strain was performed using buffered yeast extract broth (BYEB) prepared with Bacto yeast extract (Becton Dickinson and Company Sparks, MD, USA) added with Legionella BCYE growth supplement (Oxoid LTD, Basingstoke, England). Tween-80 (Sigma-Aldrich, St Louis, MO, USA) was added to BYEB to facilitate oil solubility (32). After preparing micro- dilution trays with EO solutions the filled trays were sealed in plastic bags and immediately placed in a freezer at ⁇ 20 °C until needed.
  • TTO and terpinen-4-ol were performed according to the CLSI broth micro-dilution method, with the following modifications: 1 ) BYEB instead of Muller-Hinton broth; 2) emulsifier Tween 80; 3) inoculum size 10 8 instead of 10 5 CFU/ml; 4) use of a sterilised Transparent Microplate Sealer (TMS) during incubation for 72 h. TTO and terpinen-4-ol were diluted using BYEB in the presence of Tween 80 at 0.001 % v/v.
  • TMS Transparent Microplate Sealer
  • TMS Transparent Microplate Sealer
  • the minimum inhibitory concentration (MIC) values were defined as the lowest TTO or terpinen-4-ol concentration showing a growth inhibition of 100% compared with the oil-free L. pneumophila control growth as resulted spectrophotometrically or visually.
  • the minimum bactericidal concentration (MBC) values were determined by plating 10 ⁇ from each wells with no apparent growth onto BCYE-cc agar medium and incubated at temperature ranging from 36° to 45 °C with 2.5% CO 2 , After 72 h the viability was assessed. Each experiment was carried out in duplicate. MBC were defined as the lowest oil concentration resulting in the death of
  • Agar diffusion method BCYE- ⁇ agar medium added with sterile Tween 80 (0.01 % v/v) was used to assay the susceptibility of L. pneumophila reference strains, clinical and environmental Lp1 and Lp6, to terpinen-4-ol in this assay. Approximately 1x10 8 CFU/ml were used to lawn inoculate solid media. A 6 mm in diameter paper disc (Oxoid, LTD, Basingstoke, England) was placed on the inoculated agar surfaces and impregnated with of 10 ⁇ of pure terpinen-4-ol.
  • a slightly modified agar diffusion method was used to estimate the terpinen-4-ol activity on L. pneumophila reference, clinical and environmental strains Lp1 and Lp6, in vapour phase, (27,28).
  • a micro- coverglass (Prestige, Italy, 22 mm x 22 mm) was attached with a drop of commercial enamel on the upper lid of a Petri dish.
  • a 6 mm in diameter paper disc (Oxoid, Unipath LTD, Basingstoke, England) moistened with 10 ⁇ of pure terpinen-4-ol was put at the centre of this slide.
  • the surface of the disc was at a distance of about 4 mm from the growth surface of the test organism.
  • Tween 80 In order to exclude the interference of the detergent in our assay we carried out preliminary experiments in our working condition to establish the correct solubilising but non-inhibitory concentration of Tween 80. In fact, and as already described (33), various detergents could have an inhibitory effect against some Legionella species depending on the concentration.
  • Table 2 compares the MIC 50 and MIC 90 of the two serogroups isolates. In both tables, the uniformity of MIC values at 0.25% v/v and the MBC values at 0.5% v/v is noticed, with rare exceptions, and no differences either between the two serogroups or between the environmental and the clinical isolates.
  • Table 3 shows in independent experiments the comparison of TTO and terpinen-4-ol an ⁇ -Legionella activity at temperatures of 40°C and 45 °C, showing the markedly superior terpinen-4-ol activity compared to TTO at these temperatures with respect to 36°C.
  • Micro-atmosphere diffusion method terpinen-4-ol vapours effect on Legionella pneumophila (Lp) serogroups growth
  • Table 5 shows the comparative effects of TTO and terpinen-4-ol in the temperature range of 36 to 45°C for three selected strains of Legionella pneumophila. It is quite evident that temperature increase causes a dissociation between TTO and terpinen-4-ol anti- Legionella activity markedly in favour of the latter, at least in some representative strains, as assessed by the diameter of growth inhibition. Table 5.
  • Micro-atmosphere diffusion method tea tree oil and terpinen 4-ol vapours effects on Legionella pneumophila (Lp) after seven days contact 2 at different temperatures.
  • Legionella pneumophila - a human pathogen that co-evolved with fresh water protozoa. Cell Mol. Life Sci. 64, 432-448.

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Abstract

La présente invention concerne l'utilisation de terpinèn-4-ol, à la fois dans des solutions aqueuses et sous forme gazeuse, en tant qu'agent antimicrobien contre des bactéries du genre Legionella, de préférence Legionella pneumophila, pour des systèmes de désinfection pour la distribution ou le stockage d'eau, tels que des systèmes de distribution d'eau pour des bâtiments, des tours de refroidissement, des spas, des petits circuits d'eau tels qu'une unité dentaire, des dispositifs médicaux présents dans des équipements hospitaliers et de soins de santé ou des dispositifs médicaux d'assistance respiratoire, pour les bactéries mentionnées ci-dessus. L'invention indique des concentrations de terpinèn-4-ol et des plages de température optimales pour l'expression d'une activité anti-Legionella.
PCT/IT2011/000267 2010-07-26 2011-07-25 Utilisation de terpinèn-4-ol en tant qu'agent antimicrobien contre des bactéries du genre legionella WO2012014244A1 (fr)

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ITRM2010A000414 2010-07-26
ITRM2010A000414A IT1401202B1 (it) 2010-07-26 2010-07-26 Uso del terpinen-4-ol come agente antimicrobico contro la legionella pneumophila.

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT201900012408A1 (it) * 2019-07-19 2021-01-19 Silvio Carta Olio essenziale di Artemisia arborescens, metodo per la sua preparazione e suo uso come anti-microbico.
CN115317468A (zh) * 2022-09-22 2022-11-11 贵州医科大学 萜品-4-醇在制备抗炎药物或抗呼吸道合胞病毒药物中的应用

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