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Chemical composition, antimicrobial activities and
olfactory evaluations of an essential marjoram oil from
Albania as well as some target compounds
Chemische Zusammensetzung, antimikrobielle Aktivitäten und
olfaktorische Beurteilungen eines ätherischen Majoranöls aus
Albanien sowie einiger Schlüsselkomponenten
L. Jirovetz, S. Bail, G. Buchbauer, Z. Denkova, A. Slavchev, A. Stoyanova, E. Schmidt
The chemical composition of an essential marjoram oil from Die chemische Zusammensetzung eines kommerziell herge- Albania produced for commercial purposes was analysed stellten ätherischen Majoranöls aus Albanien wurde mittels by GC and GC/MS. 28 volatiles were identified and the fol- GC und GC/MS analysiert. 28 flüchtige Inhaltsstoffe wurden lowing monoterpenes were found as main compounds: ter- identifiziert und als Hauptkomponenten die Monoterpe- pinen-4-ol (21.33%), trans-sabinene hydrate (15.53%), γ-ter- ne Terpinen-4-ol (21,33 %), trans-Sabinenhydrat (15,53 %), pinene (14.00%), α-terpinene (8.88%) and sabinene (8.27%).
γ-Terpinen (14,00 %), α-Terpinen (8,88 %) und Sabinen The essential Origanum majorana oil, some higher and (8,27 %) gefunden. Die antimikrobielle Aktivität des äthe- medium-concentrated constituents, a phenolic reference rischen Origanum-majorana-Öls sowie einiger Haupt- und component and three antibiotics were tested against sev- Nebenkomponenten wurden mit einem optimierten und eral microorganisms using modified and well-established bewährten Agardiffusions- und Agarverdünnungstest be- and optimised agar dilution and agar diffusion assays to stimmt. Zum direkten Vergleich wurden drei Antibiotika so- evaluate the antimicrobial activity of the oil as well as these wie eine phenolische Referenzkomponente hinzugezogen. target compounds. In addition, the analytical results were Die analytischen Resultate wurde mit olfaktorischen Bewer- correlated with olfactoric evaluations for reasons of quality tungen zur Qualitätskontrolle dieses ätherischen Majoran- control of the essential marjoram oil.
Essential oil, Origanum majorana L., chemical composition, Ätherisches Öl, Origanum majorana L., chemische Zusam- antimicrobial activities, olfactoric evaluations mensetzung, antimikrobielle Aktivitäten, olfaktorische Beur- 1 Introduction
vouring of foodproducts, the applications of these oils in perfumery and cosmetics as well as the biological, In continuation of an international project in the field of pharmacological and toxicological effects as fresh combined data interpretation of composition analysis, plant, herb, tea, extract and especially essential oil for odour evaluation and antimicrobial activity testings of the treatment of various diseases are available so far various aroma samples [1], an essential oil of marjo- ram (Origanum majorana L., syn. Majorana hortensis Moench., Lamiaceae – common names: English: mar- This immense number of chemical and antimicrobial data joram, sweet marjoram, knotted marjoram; Arabic: is based on different non-commercial marjoram samples. bardagoush, barsagusha, mardqouche, mizunjuske; The aim of this respective study was to analyze an es- Dutch: marjolein; French: marjolaine, origane; German: sential oil of Origanum majorana from Albania produced Gartendost, echter Majoran, Meiran, Wurstkraut [2, 3] under commercial manufacturing conditions by means – from Albania was investigated. Many papers about of GC and GC/MS analysis, olfactory evaluation and anti- the composition of Origanum majorana, its extracts microbial testings, using well-established and optimised and essential oils, its utilisation as spice and for fla- agar diffusion and agar dilution methods [1]. 2 Materials and methods
For other parameters, see description of GC/FID, above. Mass spectra correlations were done using 2.1 Samples and reference compounds
Wiley, NBS, NIST and our own library as well as pub- Sabinene hydrate (purity: 98.1%, product no.: 96573) is a product of Fluka-Riedel-de Haen-Sigma Aldrich
(Buchs, Switzerland); α-terpinene (85.1%, 22,318-2), 2.4 Antimicrobial testings
γ-terpinene (97.2%, 22,319-0), terpinolene (90.2%,
The essential oil of marjoram, the target compounds W30,460-3-K), myrcene (90.0%, 276200), (S)-(-)-limo- and the reference compound were prepared as 20% nene (95.0%, W504505), and tetracycline hydrochlo- solutions of ethanol and dissolved in a 0.9% NaCl so- ride (achromycine hydrochloride – 25g, T3383-25G) lution. As test microorganisms (colony-forming units are products from Sigma-Aldrich Austria Co., Vienna. per cm3 = cfu/cm3), Gram-positive bacteria Staphylo- The essential marjoram oil sample from Albania coccus aureus ATCC 6538P (1.5x1013) and Enterococ- (800522) was obtained by hydrodistillation from the cus faecalis (clinical isolated, 1x1013), Gram-negative flowering tops of Origanum majorana L. with physi- bacteria Escherichia coli ATCC 8739 (1x1011), Pseudo- co-chemical data: rotation +17.7°, density: 0.892, monas aeruginosa G 28 (2x1013), Klebsiella pneumoni- refraction: 1.4754; and the following reference com- ae (clinical isolated, 2x1013), Proteus vulgaris (clinical pounds as terpinen-4-ol (99.1%, 800760), α-terpineol isolated, 6x1013) and Salmonella enterica subsp. en- (82%, 800761), linalool (96%, 800506), linalyl acetate terica (clinical isolated, 3x1013) as well as the yeast (96%, 800507), p-cymene (97.0%, 800613), α-pinene Candida albicans ATCC 10231 (1.9x1010) – all products (97%, 800079), β-pinene (95%, 800140), β-caryophyl- from the National Bank of Industrial Microorganisms lene (97.5%, 800173), eugenol (98.3%, 800316) were and Cell Cultures, Sofia, Bulgaria – were used.
purchased from Kurt Kitzing Co., Wallerstein. Ciprox- The antimicrobial activity was studied by two well- in® 500 mg tablets (1 tablet = 582 mg ciprofloxacine established and optimised methods as follows: agar hydrochloride/water) were bought from Bayer Austria diffusion disc method using 6 mm paper discs and Co., Vienna and Lidaprim® infusion bottle (250 mg quantities of 6.0 μL of the sample. After cultivation of containing 0.8 g sulfametrol and 0.16 g trimethoprim) the bacteria and the yeast at 37 °C for 24 h the diam- eter of the inhibition zone (IZ) was measured. Agar serial tube dilution method results in a minimum in- 2.2 GC analysis
hibitory concentration (MIC) as follows: The essential GC/FID analyses were carried out using a GC-14A with oil, pure and reference compounds were added to a split/splitless injector, FID and C-R6A-Chromatopac in- saline solution (0.5% NaCl in distilled water) contain- tegrator (Shimadzu, Japan), a GC-3700 with FID (Var- ing 1.0% (v/v) Tween 80 at the appropriate volumes ian, Germany) and C-R1B-Chromatopac integrator to produce final concentrations of the samples in (Shimadzu). The carrier gas was hydrogen (flow rate: the range of 1–1000 ppm. Petri dishes were inoculat- 1 mL/min); injector temperature 250 °C; detector tem- ed by pipetting 6.0 μL of the serial diluted samples, perature, 320 °C. The temperature programme was: the reference compounds (the tablets of Ciproxin® 40 °C/5 min to 280 °C/5 min, with a heating rate of were added as solution in saline at a quantity of 6 °C/min. The columns were 30 m x 0.25 mm bonded 300 μg) and 0.1 cm3 of the desired culture on paper DB-5MS fused silica, with a film thickness of 0.50 μm discs (6 mm) and then incubated at 37 °C for 24 h.
(J & W Scientific Corp., USA) and 30 m x 0.32 mm
bonded Stabilwax, with a film thickness of 0.50 μm 2.5 Olfactoric evaluations
(Restek, USA). Quantification was achieved using The essential marjoram oil from Albania was olfac- peak area calculations, and compound identification torily evaluated by a professional perfumer and two was carried out partly using correlations between re- aroma chemists; the aroma described in Tab. 1 corre- lated with odour impressions published [1, 24–29]. 2.3 GC/MS analysis
3 Results and discussions
For GC/MS measurements a GC-17A with QP5050 (Shi-madzu, Japan), split/splitless injector and HP-Com- The essential oil of Origanum majorana L. from Albania paq data system (Hewlett-Packard, USA, Shimadzu was olfactorily evaluated as follows: herbaceous, aromat- GCMSsolution software) and a GC-17A with QP5000 ic-spicy, slightly terpenous, reminding of terpinen-4-ol. (Shimadzu, Japan), split/splitless injector and Pen- By means of gas chromatographic-spectroscopic tium PC data system (HP, USA, Shimadzu class5k analysis (GC/FID and GC/MS) of the essential marjo- software) were used. The carrier gas was helium (flow ram oil 28 constituents were identified. The chemical rate: 1 mL/min); injector temperature 250 °C; interface composition confirms the authenticity of the sample heating at 300 °C, ionsourceheating at 200 °C, EI- by comparing retention indices with those of literature mode was 70 eV, and the scan range was 41–450 amu. data mentioned in Tab. 1 as well as scientific publica- Relative
Proteus vulgaris, Klebsiella la enterica subsp. enterica) * non-polar/polar column# in relative % peak area using GC-FID with a non-polar column (mean value of 3 analyses) § in accordance to published data [1, 24–29] of high antimicrobial active, phenolic compounds euge- Tab. 1: Composition and olfactoric evaluation of the marjoram essential oil from nol and the synthetic antibi-
Tab. 1: Zusammensetzung und olfaktorische Beurteilung des ätherischen Majo- ride and Ciproxin® (these
ranöls aus Albanien.
products and Lidaprim® are known to have no effects tions and own databases. The main compounds were against the yeast C. albicans) prove the effectivity of as follows (concentration higher than 3.0%, calculated the chosen testing methods, while Lidaprim® (no ef- as relative % peak area using GC/FID with a non-polar fects against P. aeruginosa and K. pneumoniae) did not column, see Tab. 1): terpinen-4-ol (21.33%), trans-sabi- show the antimicrobial activity as expected [1]. nene hydrate (15.53%), γ-terpinene (14.00%), α-terpi- Antimicrobial tests with pure compounds, identified as nene (8.88%), sabinene (8.27%), cis-sabinene hydrate main or minor constituents of the essential marjoram (3.80%), α-terpineol (3.26%) and terpinolene (3.20%). oil, such as α- and γ-terpinene, terpinolene, terpinen- Using olfactoric data of previously published refer- 4-ol, α-terpineol, linalool, linalyl acetate, p-cymene, ences (see references cited in Tab. 1) the character- myrcene, limonene, α- and β-pinene, sabinene hy- istic odour of the marjoram sample can be especially drate (mixture of cis- and trans-sabinene hydrate) and correlated to α-thujene, α-terpinene, γ-terpinene and caryophyllene showed the following antimicrobial ac- bicyclogermacrene (herbaceous notes), sabinene, tivity (see Tab. 2): Only the monoterpene alcohols ter- α-phellandrene, β-phellandrene, cis- and trans-sabi- pinen-4-ol, α-terpineol and linalool were moderately nene hydrate, cis-sabinene hydrate acetate, β-caryo- to highly effective against all strains of Gram-positive phyllene, α-humulene, bicyclogermacrene and caryo- and Gram-negative bacteria as well as the yeast, simi- phyllene oxide (aromatic-spicy notes), α- and β-pi- larly to the marjoram sample. Therefore, these three nene, α- and γ-terpinene, terpinolene and terpinen-4-ol constituents are of basic importance for the excellent Staphylo-
enterica subsp.
coccus aureus
1.5x1013 cfu/cm3 1x1013 cfu/cm3 1x1011 cfu/cm3 2x1013 cfu/cm3 6x1013 cfu/cm3 2x1013 cfu/cm3 3x1012 cfu/cm3 1.9x1010 cfu/cm3 Tab. 2: Antimicrobial activities of the essential marjoram oil from Albania, some main and minor compounds
as well as reference compounds.
Tab. 2: Antimikrobielle Aktivität des ätherischen Majoranöls, einiger Haupt- und Nebenkomponenten sowie der
antimicrobial properties of the essential O. majorana Acknowledgement
oil from Albania. All other tested compounds (without The authors acknowledge the valuable help of Prof. γ-terpinene against S. aureus and myrcene against Dr. Heinz Schilcher, Emeritus of the Freie Universität both Gram-positive bacteria) were found to have a Berlin, in the field of antimicrobial test methods.
medium to high effectivity against the Gram-positive bacteria and the yeast C. albicans (only myrcene did References
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