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Chemical composition, antimicrobial activities and odor descriptions of various Salvia sp. and Thuja sp. essential oilsChemische Zusammensetzung, antimikrobielle Aktivitäten und Geruchsbe-schreibungen von verschiedenen Salvia sp. und Thuja sp. ätherischen Ölen L. JIROVETZ, G. BUCHBAUER, Z. DENKOVA, A. SLAVCHEV, A. STOYANOVA, E. SCHMIDT The chemical composition of various commercially avail- Die chemische Zusammensetzung von verschiedenen kom- able Salvia sp. (S. officinalis (two samples), S. sclarea, S. merziell erhältlichen Salvia sp. (S. officinalis, S. sclarea, S. lavandulifolia) and Thuja sp. (T. plicata, T. occidentalis) es- lavandulifolia) und Thuja sp. (T. plicata, T. occidentalis) äther- sential oils were analyzed by GC and GC/MS. More than fifty ischen Ölen wurden mit GC und GC/MS analysiert. Mehr als volatiles were identified in all samples with the monoter- fünfzig flüchtige Inhaltsstoffe wurden in allen Proben iden- penes camphor, 1,8-cineole, fenchone, linalool, linalyl ace- tifiziert und die Monoterpene Kampfer, 1,8-Cineol, Fenchon, tate, sabinene, sabinyl acetate, α-thujone and β-thujone as Linalool, Linalylacetat, Sabinen, Sabinylacetat, α-Thujon und main compounds. These analytical results were correlated β-Thujon als Hauptkomponenten identifiziert. Diese analy- with olfactoric evaluations for reasons of quality control of tischen Resultate wurden mit olfaktorischen Bewertungen these essential oils. Furthermore, all samples, some higher zur Qualitätskontrolle dieser ätherischen Öle korreliert. concentrated constituents, a phenolic reference compound Weiters wurden alle Proben, einige höher konzentrierte and three classic antibiotics were tested against several mi- Inhaltsstoffe, eine phenolische Vergleichskomponente und croorganisms to get informations about the antimicrobial drei klassische Antibiotika gegen einige Mikroorganismen getestet, um Informationen über die antimikrobielle Aktivität jedes ätherischen Öles zu erhalten.
Essential oils, Salvia sp., Thuja sp., thujones, composition, Ätherische Öle, Salvia sp., Thuja sp., Thujone, Zusam- mensetzung, antimikrobielle Aktivitäten, Geruch ice-creams, candies and baked goods, chewing gums, condiments, meats and pickles [14, 18, 41, 44], the ap- In continuation of an international project in the field plications of these oils in perfumery and cosmetics of combined data interpretation of composition ana- [4, 6] as well as the biological, pharmacological and lysis, odor evaluation and antimicrobial activity tes- toxicological effects as fresh plant, herb, tea, extract tings [14, 23, 24, 43] of various aroma-samples, essen- and essential oil for the treatment of various diseases tial oils of sage (Salvia officinalis L., Lamiaceae) from [3, 7, 12, 14, 15, 17, 20, 31, 34, 41, 42, 46, 50, 51] are Bosnia-Hercegovina and Egypt, Spanish sage (Salvia lavandulifolia Vahl, Lamiaceae), clary sage (Salvia sclarea L., Lamiaceae) from Russia, western red cedar In addition, some data about biology, pharmacology, wood-leaves (Thuja plicata Donn ex D. Don, Cypres- toxicology, odor and use in food-flavorings, perfum- saceae) from Canada and eastern white cedar wood- ery and cosmetics as well as medical applications of leaves (Thuja occidentalis L., Cypressaceae) from the main compounds (e. g. α- and β-thujone, camphor, 1,8-cineole, linalool and linalyl acetate) were pub- Many papers about the composition of Salvia sp. and lished elsewhere [2, 4, 7, 3-16, 18, 23, 24, 31, 33, 41, Thuja sp., their extracts and essential oils [4, 5, 8, 9, 11, 19-21, 27-30, 32, 35-40, 44, 47-50], the use of the Although this immense number of data about sage- essential sage and thuja oils for the flavoring of foods, and thuja-samples exists, to the best of our know- e. g. alcoholic and non-alcoholic beverages, bitters, ledge, up to now no combined interpretation of data from GC and GC/MS analysis, olfactoric evaluation and antimicrobial testings (using agar diffusion and For GC/MS measurements a GC-17A with QP5000 agar dilution method, both), including comparisons (Shimadzu) and Compaq-ProLinea data system with antimicrobial data of some main compounds and (class5k-software), a GC-HP5890 with HP5970-MSD commercial antibiotics, have been done on essential (Hewlett-Packard, USA) and ChemStation software on oils of Salvia sp. and Thuja sp. from various origin.
a Pentium PC (Böhm, Austria), a GCQ (Finnigan-Spec-tronex, Germany-USA) and Gateway-2000-PS75 data system (Siemens-Nixdorf, Germany, GCQ-software) were used. The carrier gas was helium; injector tem- perature at 250 °C; interface-heating at 300 °C, ion- Camphor (W52,660-6), β-caryophyllene (W22,520-7), source-heating at 200 °C, EI-mode was 70 eV, and the 1,8-cineole (W24,650-6), limonene (W26,330-3), linalo- scan-range was 41-450 amu. For other parameters, ol (W26,350-8), linalyl acetate (W26,350-5), α-terpineol see description of GC/FID, above. Mass spectra cor- (W30,452-2), α-thujone (89231), eugenol (W24,670-0) relations were done using Wiley, NBS, NIST and our and tetracycline hydrochloride (achromycine hy- own library as well as published data [1, 22, 25].
drochloride – 25 g, T3383-25G) are products from Sigma-Aldrich Austria Co., Vienna; Salvia officinalis 1 (sage, Lamiaceae) was obtained from Aroma & Fla- The essential oil of sage, the key compounds and the vor Chemistry Department – National Research Cen- reference compound were prepared as 20 % solu- ter Giza (Egypt); terpinen-4-ol (800760), western red tions of ethanol and dissolved in a 0.9 % NaCl solu- cedar wood leaf-oil (800177; Thuja plicata Donn ex D. tion (ratio of 1:10). As test microorganisms (colony- Don, Cypressaceae, Canada; green leaves), eastern forming-units=cfu/cm3), Gram-(+)-bacteria Staphylo- white cedar wood leaf-oil (800914; Thuja occidenta- coccus aureus ATCC 6538P (1x1013) and Enterococcus lis L., Cypressaceae, Balkan-area, green leaves) Sal- faecalis (clinical isolated, 1x1013); Gram-(-)-bacteria via officinalis L. 2 (sage, 801510; Bosnia-Hercegovina, E. coli ATCC 8739 (2x1012), Pseudomonas aeruginosa leaves of flowering top of the plant), Salvia lavandu- G 28 (1.2x109), Klebsiella pneumoniae (clinical isolat- lifolia Vahl (Spanish sage, Lamiaceae, 800283; leaves ed, 1x1013), Proteus vulgaris (clinical isolated, 3x1013) of the flowering top of the plant) and Salvia sclarea and Salmonella sp. (clinical isolated, 3x1012) as well L. syn Salvia sclarea var. turkestaniana Mottet (clary as the yeast Candida albicans ATCC 10231 (1x1011) sage, Lamiaceae, 800738; Russia, leaves of the flow- – all products from the National Bank of Industrial ering top of the plant) were purchased from Kurt Microorganisms and Cell Cultures, Sofia, Bulgaria Kitzing Co., Wallerstein; β-thujone (no product-num- ber given) was delivered from Symrise Co. (former Dragoco Co.), Holzminden; CiproxinR 500 mg-tablettes The antimicrobial activity was studied by two methods: (one tablette = 582 mg ciproflaxoxacine hydrochloride 1. Agar diffusion disc method using 6 mm paper discs /water) bought from Bayer Austria Co., Vienna and and quantities of 6 μL of the sample. After cultiva- LidaprimR-infusion-bottle (250 mg containing 0.8 g tion of the bacteria and the yeast at 37 °C for 24 h the sulfametrol and 0.16 g trimethoprim) from Nycomed diameter of the inhibition zone (IZ) was measured. 2. Agar serial tube dilution method with results as minimum inhibitory concentration (MIC) as follows: The essential oil, pure and reference compounds GC/FID analyses were carried out using a GC-14A with were added to brine, containing 1.0 % (v/v) Tween 80 FID and C-R6A-Chromatopac integrator (Shimadzu, at the appropriate volumes to produce final concen- Japan), a GC-3700 with FID (Varian, Germany) and trations of the samples in the range of 100-1.000 ppm; C-R1B-Chromatopac integrator (Shimadzu). The car- the Petri dishes were inoculated by pipetting 0.1 cm3 rier gas was hydrogen; injector temperature 250 °C; of the desired culture and 0.6 μL of the samples as detector temperature 320 °C. The temperature pro- well as the reference compounds (the tablettes of Cip- gramme was: 40 °C/5 min to 280 °C/5 min, with a heat- roxinR were added as solution in saline at a quantity of ing rate of 6 °C/min. The columns were 30 m x 0.32 300 μg) on paper discs (6 mm) and then incubated at mm bonded FSOT-RSL-200 fused silica, with a film thickness of 0.25 μm (Biorad, Germany) and 30 m x 0.32 mm bonded Stabilwax, with a film thickness of 0.50 μm (Restek, USA). Quantification was achieved All investigated samples were olfactorically evaluated using peak area calculations, and compound identi- by a professional perfumer and two aroma-chemists; fication was carried out partly using correlations bet- the aroma described in Table 1 correlated with odor im- ween retention times [1, 10, 22, 25, 26]. pressions published elsewhere [2, 4, 7, 16, 18, 33, 45].
Component
green-leafy, weak rose-like, sweet-fruity Tab. 1: Composition and olfactoric evaluation§ of the Salvia sp. and Thuja sp. essential oils including their
retention-indices* and percentage#
in accordance to published data elsewhere [2, 4, 7, 16, 18, 33, 45] and private olfactoric evaluation data from pure aroma com- in relative %-peak area using GC with an apolar column (mean value of three analyses) So1 Salvia officinalis (Egypt) and So2 (Bosnia-Hercegovina); Sl3 S. lavandulifolia, Ss4 S. sclarea, Thp5 Thuja plicata and Tho6 (Thuja High antimicrobial activity of both S. officinalis sam-ples and T. occidentalis; Gram-(-)-bacterium E. coli: The essential oils were olfactorically evaluated as fol- Very high activity of S. officinalis from Bosnia-Herce- lows: Salvia officinalis1 (Egypt): Characteristic sage govia and high activity of all other samples excluding odor with a fresh-camphoraceous and rosemary- S. lavandulifolia; Gram-(-)-bacterium Proteus vulgaris: pine-like top-note and herbal-minty thujone-base- Very high activity of T. plicata and high activity of both notes; S. officinalis2 (Bosnia-Hercegovina): Green- S. officinalis samples; Gram-(-)-bacterium Pseudomo- herbal, intense thujone-notes; S. lavandulifolia: nas aeruginosa: Very high activity of S. lavandulifolia Intense fresh-eucalyptus-top-note, camphoraceous and S. sclarea as well as T. plicata; Gram-(-)-bacteri- (direction of spike-lavender), green-fresh-notes from um Salmonella sp.: Very high activity of S. officinalis sage; S. sclarea: Fresh-floral, intense lavender-note from Egypt and S. lavandulifolia; Gram-(-)-bacterium (linalool and linalyl acetate), herbal-spicy-woody in Klebsielle pneumonia: Very high activity of both S. of- the background; Thuja plicata: Intense thujone-note ficinalis samples and S. sclarea; Gram-(+)-bacterium with green-herbal side-notes; T. occidentalis: Fresh- Enterococcus faecalis: Very high activity of S. lavan- spicy, green-herbal thujone-notes, woody-earthy in dulifolia and T. occidentalis; yeast Candida albicans: High activity only of both S. officinalis samples.
By means of gas chromatographic-spectroscopic ana- Correlations with the data of the high antimicrobial ac- lysis (GC/FID and GC/MS) of the essential oils about tive, phenolic compounds eugenol and the synthetic seventy constituents could be identified with the main antibiotics tetracycline hydrochloride and CiproxinR compounds as follows (concentration higher than (these products and LidaprimR are known to have no 3.0 %, calculated as relative %-peak-area using GC- effects against the yeast C. albicans) prove the effec- FID with an apolar column) of the single samples (see tivity of the chosen testing methods, while LidaprimR Table 1): S. officinalis1 (Egypt): Camphor (25.11 %), (no effect against P. aeruginosa and K. pneumoniae) α-thujone (22.19 %), β-thujone (17.70 %), 1,8-cineole was found to have not the antimicrobial activity as (7.45 %), α-humulene (4.51 %), β-elemene (3.71 %) and expected. camphene (3.45 %); S. officinalis 2 (Bosnia-Hercegovi-na): α-Thujone (21.48 %), camphor (18.08 %), 1,8-cin- Antimicrobial testings with the two main compounds eole (9.69 %), β-thujone (8.78 %), camphene (7.09 %), of both sage samples, α-thujone and β-thujone α-pinene (6.48 %), β-caryophyllene (6.18 %) and β-pinene showed high effects against the Gram-(-)-bacteria P. (3.74 %); S. lavandulifolia: Camphor (29.17 %), 1,8-cin- aeruginosa and K. pneumoniae and medium effects eole (25.52 %), camphene (5.59 %), limonene (5.02 %), against St. aureus, E. coli and C. albicans. α-pinene (4.91 %), β-pinene (4.59 %), linalyl acetate (4.17 %) and sabinyl acetate (3.41 %); S. sclarea: Lina- Antimicrobial data of further constituents of the es- lyl acetate (59.95 %), linalool (20.98 %), α-terpineol sential sage and thuja oils, published elsewhere [13, (4.01 %) and geraniol (3.22 %); T. plicata: α-Thujone 23, 24, 43], such as camphor, β-caryophyllene, 1,8-cin- (54.13 %), fenchone (15.12 %), β-thujone (6.83 %) and eole, limonene, linalool, linalyl acetate, terpinen-4-ol sabinene (4.39 %); T. occidentalis: Sabinyl acetate and α-terpineol were correlated to confirm our experi- (16.55 %), fenchone (12.87 %), sabinene (12.14 %), ence from previous studies [13, 23, 24, 43] in the field, β-thujone (9.48 %), α-pinene (3.33 %) and terpinen-4-ol that not only one or two compounds are responsible for antimicrobial activities of essential oils, but the whole composition with alternating synergistic and Using olfactoric data from elsewhere (see references antagonistic effects of each volatile.
cited in Table 1) the characteristic odor of the samples can be correlated to camphene, fenchol, camphor, bor- To compare the analytical and antimicrobial results neol and fenchyl acetate (camphoraceous), limonene of this investigation with reference-data of regula- and 1,8-cineole (fresh), sabinene and sabinyl acetate tion, application and treatment of different samples (fresh-spicy), linalool and linalyl acetate (floral-fresh), (plants, plant parts, herbs, extracts and essential oils) α-pinene, β-pinene and terpinolene (pine-like) as well of Salvia sp. and Thuja sp. as well as the target com- as α-thujone and β-thujone (thujone-like).
pounds α- and β-thujone, we can state that an use of all of these essential oils for flavoring of foods, as Results of antimicrobial testings (agar diffusion and odor component in perfumery and cosmetic products agar dilution method in accordance to [13, 23, 24, 43]) and in medical preparations are possible without any of the different Salvia sp. and Thuja sp. essential oils danger, when not taken excessive and for a longer against various microorganisms were as follows (see period (remember the word of Paracelsus: “the dosis Table 2): Gram-(+)-bacterium Staphyllococcus aureus: Inhibition Zones (IZ) in mm and Minimum Inhibitory Concentrations (MIC) Staphylococcus
Pseudomonas
Escherichia coli /
Klebsiella
Candida
aureus
aeruginosa /
Proteus vulgaris
pneumoniae
albicans
Enterococcus faecalis
Salmonella sp.
Tab. 2: Antimicrobial activities of Salvia sp. and Thuja sp. essential oils and some main as well as reference
compounds
#not tested against the microorganism until now, - no inhibition observed, 1published elsewhere [23], 2published elsewhere [24], 3published elsewhere [43], 4partly published elsewhere [13] Reference
Plant/plant part/compound Data of regulation/application/treatment
Foodstuffs / beverages: 0.5 mg/kg / 0.5 mg/L, alcoholic beverages with more than 25 % volume
of alcohol: 5 mg/kg, alcoholic beverages with not more than 25 % volume of alcohol: 10 mg/kg,
foodstuffs containing preparations on sage: 25 mg/kg, bitters: 35 mg/kg
Flavoring of food with a maximum level of 0.5 mg/kg; oral LD50: 0.25 g/kg
oral-LD50: 0.83 g/kg / 2.6 g/kg
Non-alcoholic beverages: 300 ppm; baked goods: 170 ppm; meats: 1.500 ppm / non-alcoholic
beverages: 3.7 ppm; ice-cream and ice: 16 ppm; candy: 11 ppm; chewing gum: 30 ppm;
condiments: 14 ppm; meats: 110 ppm; pickles: 2.4 ppm
Non-alcoholic beverages: 2.0-11 ppm; ice-cream and ice: 2.0-44 ppm; candy: 20 ppm;
baked goods: 20 ppm; condiments: 50 ppm; meats: 40 ppm
Non-alcoholic beverages: 0.01-0.50 ppm; alcoholic beverages: 16 ppm;
ice cream and ice: 0.01-1.0 ppm; candy: 12 ppm; baked goods: 1.0-20 ppm; meats: 15 ppm
Whole leaf drug / cut leaf drug: 15 mL/kg / 10 mL/kg essential oil (water free drug)
Gastro-intestinal application / inflammation of the mouth-area: max. dosage/day: adults 4-6 g
Inflammation of the mouth-area: children 1-4: 1-3 g, 4-10: 3-4 g, 10-16: 4-6 g
4-6 g/day herb or 0.1-0.3 g essential oil: infections (bacterium, fungus and virus), pharyngosis
2 tea-spoons (3 g) cut herb/cup water: cough, cramp, diarrhea, dysmenorrhea, gastrosis
1-4 mL liquid herb extract: glossosis, inflammationsore throat, tonsilosis
1-4 g leaf, or in tea 3x/day or 1-4 mL liquid leaf extract (1:1 in 45 % ethanol) 3x/day: acne,
infections (bacterium and yeast), cramp, dyspepsia, gingivosis, pharyngosis, stomatosis
2-3 tea-spoons (3.4-5.1 g) leaf in hot tea: angina, catarrh, colic, cough, odontosis, stomatosis
boil 100 g leaf/liter wine two minutes: anorexia, asthma, infections (bacterium, fungus and virus),
bronchitis, cramp, dermatosis, diabetes, diarrhea, enterosis, fever, gastrosis, gingivosis, halitosis,
inflammation, laryngosis, mucosis, mycosis, rhinosis, stomatosis, wound-desinfection
2-4 table-spoons fresh leaf or 3-6 g dry leaf or 4.5 g dry leaf/2 mL alcohol/23 mL water: gas
Tab. 3: Some data of regulation/application/treatment for the use of thujones and thujone-rich drugs, extracts
and essential oils
In conclusion, we can report that the essential oils of [6] Boelens M.H.: Chemical and sensory evaluation various Salvia and Thuja species were found to be es- of three sage oils. Perfum Flavor 1997; 22: 19-40.
pecially rich in camphor, α-thujone, β-thujone, linalyl acetate, linalool, fenchone, sabinene, sabinyl acetate [7] Carta C., Moretti M., Peana A.: Activity of the oil and 1,8-cineole as well as some further monoterpenic of Salvia officinalis L. against Botrytis cinerea. J compounds, which are also responsible for the charac- teristic, especially fresh-camphoraceous, fresh-spicy, [8] Chalchat J., Michet A., Pasquier B.: Study of the floral-fresh, pine- and thujone-like odor of the differ- clones of Salvia officinalis L.: Yields and chemi- ent samples. Also the antimicrobial activities of the cal composition of essential oils. Flavour Fragr J essential sage and cedar wood oils against Gram-(+)-, Gram-(-)-bacteria and yeast are determined by many constituents with synergistic and antagonistic effects [9] Couladis M., Tzakou O., Mimica-Dukic N., Jancic and cannot be correlated to a single compound. An R., Stojanovic D.: Essential oil of Salvia ofiicinalis application of all the samples in foods, medicinal, L. from Serbia and Montenegro. Flavour Fragr J perfumery and cosmetic products is of very low risk, when taken in an appropriate dosage with regards to [10] Davies N.W.: Gas chromatographic retention in- dices of monoterpenes and sesquiterpenes on methyl silicone and Carbowax 20M phases. J [11] Dudai N. et al.: Dynamics of yield components The authors acknowledge the help of Prof. Dr. Ahmad and essential oil production in a commercial hy- Shalaby and Dr. Amr E. Edris, Medicinal & Aromatic brid sage (officinalis x Salvia fruticosa cv. Newe Plant Department, National Research Center Giza, for Ya’ar No. 4). J Agric Food Chem 1999; 47: 4341- the identification and characterization of the plant ma- terial, the reference compounds from Kurt Kitzing Co. and Symrise Co., the olfactoric evaluation of the sam- [12] Duke J.A., Bogenschutz-Godwin M.J., duCellier ples by Wolfgang Höppner (retired chief-perfumer of J., Duke, P.-A.K.: Handbook of Medicinal Herbs, Symrise (former Dragoco) Co., Hamburg) as well as 2nd Ed., 642-643, CRC Press, Boca Raton, 2002.
the valuable discussion about the used antimicrobial [13] Edris A.E., Jirovetz L., Buchbauer G., Denkova Z., testing methods with Prof. Dr. Heinz Schilcher, Emeri- Slavchev A., Stoyanova A.: Chemical composi- tus of the “Freie Universität Berlin”.
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Vizepräsident des OGH Hon.-Prof. Dr. K. Brustbauer [50] Velickovic D.T., Ristic M.S., Randjelovic N.V., Smelcerovic A.A.: Chemical composition and antimicrobial characteristics of the essential oils obtained from flower, leaf and stem of Salvia of- ficinalis L. originated from southern Serbia. J Es- [51] Wichtl M. (ed.): Teedrogen. Wissenschaftliche Verlagsgesellschaft mbH, Stuttgart, 1989.
Oberrat Mag.pharm. Dr. Leopold JirovetzUniv.-Prof. Mag.pharm. Dr. Gerhard Buchbauer AUSTRIAN JOURNAL FOR SCIENCE, TECHNOLOGY, Department of Clinical Pharmacy and DiagnosticsUniversity of Vienna, Pharmacy-Center e-mail: leopold.jirovetz@univie.ac.at WEIN- UND OBSTBRENNEREIEN, FRUCHTSÄFTEUND SEKTERZEUGUNG SOWIE GÄRUNGSESSIGE e-mail: gerhard.buchbauer@univie.ac.at Offizielles Organ des Verbandes der Spirituosenindustrie und des Schutzverbandes Österr. Spirituosen-, Sekt- und Fruchtsafthersteller Dr. Alexander SlavchevUniv.-Prof. Dr. Albena Stoyanova Telefon (01) 715 31 93 Telefax (01) 715 48 19 Layout: Verena MeixnerDie „ernährung“ (nutrition) – ISSN 0250-1554 – erscheint elfmal jährlich.
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