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Buchbauer, Gerhard

Antimicrobial Testings and Gas Chromatoaraphic Analysis of Pure Oxygenated Monoterpenes 1.8-Cineole, α-Terpineol, Terpinen-4-ol and Camphor as Well as Target Compounds in Essential Oils of Pine (Pinus pinaster), Rosemary (Rosmarinus officinalis), Tea

Abstract Views :177 | PDF Views:0

Authors

Leopold Jirovetz ¹, Gerhard Buchbauer ¹, Zapriana Denkova ², Albena Stoyanova ², Ivan Murgov ², Erich Schmidt ³, Margit Geissler ⁴

Affiliations
1 Department of Pharmaceutical Chemistry, University of Vienna, Althanstrasse 14, A-1090 Vienna, AT
2 University of Food Technology, Department of Essential Oils, 26 Maritza Boulevard, 4002 Plovdiv, BG
3 Kur Ktitzing GmbH, Hinterm Alten Schloss 21, D-86757 Wallerstein, DE
4 SHIMADZU Germany, Department of GC and GC/MS, Albert-Hahn-Strasse 6-10, D-47269 Duisburg, DE

Source

Scientia Pharmaceutica, Vol 73, No 1 (2005), Pagination: 27-38

Abstract

The oxygenated monoterpenes 1,8-cineole, α-terpineol, terpinen-4-ol and camphor as well as essential oils of pine, rosemary and tea tree, rich in these volatiles, were tested for their antimicrobial activities against some different strains of yeast, Gram-(-)- and Gram-(+)-bacteria by agar diffusion and agar dilution method, respectively. The same was done using the phenolic aroma compound eugenol as a reference-substance. The monoterpene alcohols α-terpineol and terpinen-4-ol were found to be active against all strains used in a wide range. The same result was obtained for the testings of essential oils of pine, rosemary (2 samples) and tea tree. Nearly all aroma chemicals and essential oils did show a significant high antimicrobial activity against Staphylococcus aureus and Pseudomonas aeruginosa. For qualitative and quantitaive investigations of the key aroma compounds and the compositions of the essential oils, gas chromatographic methods (GC-FID and GCMS with columns of different polarities) were used and the results correlated with that of the antimicrobial testings. The obtained data are discussed to get more insight into the influence of pure aroma compounds on antimicrobial activities of essential oils.

Keywords

Essential Pine Oil, Essential Rosemary Oils, Essential Tea Tree Oil, Oxygenated Monoterpenes, Antimicrobial Testing, GC

Full Text

References

Jirovetz, L., 34^th International Symposium on Essential Oils, September 10^th, 2003, Lecture 18, Wuerzburg, Germany.

Jirovetz, L., Buchbauer, G., Stoyanova, A., Denkova, Z., Murgov, I., EURO COSMETICS 12 (1), 30-33 (2004).

Jirovetz, L., Buchbauer, G., Stoyanova, A., Denkova, Z., Murgov, I., Ernaehrung/Nutrition 28 (6), 257-260 (2004).

Jirovetz, L., Buchbauer, G., Stoyanova, A., Denkova, Z., Murgov, I., Schmidt, E., Geissler, M., J. Essent. Oil-Bearing Plants, in press (2004).

Jirovetz, L., Buchbauer, G., Stoyanova, A., Denkova, Z., Murgov, I., Schmidt, E., Geissler, M., III International Symposium Breeding Research on Medicinal and Aromatic Plants (ISMAP), July 5-8, 2004, Poster 136, Campinas, Brasil.

Schmidt, E., Jirovetz, L., Buchbauer, G., Stoyanova, A., Denkova, Z., Murgov, I., Geissler, M., 35^th International Symposium on Essential Oils, September 8-10, 2004, Poster 76, Messina, Italy.

Bauer, K., Garbe, D., Surburg, H. Common Fragrance and Flavor Materials, 3^rd Ed., VCH, Weinheim (1997).

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Osterreichisches Arzneibuch (Pharmacopoae Austriaca) 1981, 1. Nachtrag, 213-215, Aetheroleum Rosmarini, Staatsdruckerei, Wien (1981).

Osterreichisches Anneibuch (Pharmacopoae Austriaca) 1990, 12. Nachtrag, Aetheroleum Terebinthinae rectificatum, Verlag Oesterreich, Wien (2004).

Macchioni, F., Cioni, P.L., Flamini, G., Morelli, I., Maccioni, S., Ansaldi, M., Flavour Fragr. J. 18, 139-143 (2003).

Reichling, J., Harkenthal, M., Dtsche. Apoth.-Ztg. 138 (38), 47-54 (1998).

Boutekedjiret, C., Bentahar, F., Belabbes, R., Bessiere, J.M., Flavour Fragr. J. 18,481-484 (2003).

Salido, S., Altarejos, J., Nogueras, M., Sanchez, A., Luque, P., J. Essent. Oil Res. 15, 10-14 (2003).

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Shellie, R., Marriott, Ph., Zappia, G., Mondello, L., Dugo, G., J. Essent. Oil Res. 15, 305-312 (2003).

Adam, K., Sivropoulou, A,, Kokkini, S., Lanaras, T., Arsenakis, M., J.Agric. Food Chem.46, 1739-1745 (1998).

Baer, B., Analytik und Mikrobiologie des atherischen Ols verschiedener Kamillenarten, Thesis, Freie Universitat Berlin (1995).

Baratta, T., Dorman, S., Deans, S., Figueiredo, A., Barroso, J., Ruberto, G., Flavour Fragr. J. 13, 235-244 (1998).

Boesel, R., Pharmakologische, phytochemische und mikrobiologische Untersuchungen von Quecken wurzelstock Rhizoma Graminis (Erg. -B. 6) (Agropyron repens (L.) PALISOT DE BEAUVOIS, Poaceae), Thesis, Freie Universitaet Berlin (1991).

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Davidson, P., Parish, M., Food Technol. 1989, 148-155.

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Griffin, S., Grant, W., Markham, J., Leach, D., Flavour Fragr.J. 14, 323-332 (1999).

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Hood, J .R., Wilkinson, J.M., Cavangh, M.A., J.Essent.Oil.Res. 15, 428-433 (2003).

Illiev, S., Papanov, G., Malakov, P., Hristeva, P., Tomova, K., University of Plovdiv, Scientific works 21, No. 3, 105-112 (1983).

Janssen, A.M., Scheffer, J.J.C., Baerheim Svendsen, A., Planta Med. 1987, 395-398.

Jirovetz, L., Buchbauer, G., Stoyanova, A.S., Georgiev, E.V., Damianova, St.T., J. Agric. Food Chem. 51, 3854-3857 (2003).

Johnson, T.R., Case, Ch.L., Laboratory Experiments in Microbiology - Brief Edition, 3^rd Ed., 153-155, The Benjamin/Cummings Publishing Company, Inc., Redwood City (1992).

Lis-Balchin, M., Deans, A., Eaglesham, E., Flavour Fragr.J. 13, 98-104 (1998).

Neunaber, E., Phytochemische und mikrobiologische Untersuchungen von Propolis verschiedener Provenienz als Beitrag zur Kenntnis der Wirkprinzipien in Propolis, Thesis, Freie Universitat Berlin (1995).

Paukova, T., Stoichev, I., Shabanova, R., Higher Institute of Flavor and Fragrance Industries, Plovdiv, Scientific works 20, No. 3, 305-314 (1973).

Stendel, H., Seifen-Ole-Fette-Wachse 97, 736-738 (1971).

Zaika, L., J.Food Safety 9, 97-118 (1988).

Arctander, St., Perfume and Flavor Chemicals, Vol. I, II & III, Arctander Publication, Montclair (1969).

Fazzalari, F.A., Compilation of Odor and Taste Threshold Values Data, American Society for Testing and Materials, Philadelphia (1978).

Bauer, K., Garbe, D., Surburg, H., Common Fragrance and Flavor Materials, 3^rd Ed., VCH, Weinheim (1997).

Furia, T.E., Bellanca, N. (Eds.), Fenaroli's Handbook of Flavor Ingredients, 2^nd Edition, Vol. I & II, CRC Press, Cleveland (1975).

Sigma-Aldrich, Flavors & Fragrances, The Essence of Excellence, Sigma-Aldrich Co., Milwaukee (2003).

Medicinal used Plants from India: Analysis of the Essential Oil of Air-Dried Biophytum sensitivum (L.) DC

Abstract Views :218 | PDF Views:0

Authors

Leopold Jirovetz ¹, Gerhard Buchbauer ¹, Andrea Wobus ¹, Mohamed P. Shafi ², Beena Jose ²

Affiliations
1 Department of Pharmaceutical Chemistry, University of Vienna, Althanstrasse 14, A-1090 Vienna, AT
2 Department of Chemistry, Calicut University, Kerala 673 635, IN

Source

Scientia Pharmaceutica, Vol 72, No 1 (2004), Pagination: 87-96

Abstract

The essential oil of the air-dried plant Biophytum sensitivum (L.) DC. (Oxalidaceae) from Southern lndia was investigated by gas chromatographic-spectroscopic (GC-FID and GC-MS) and olfactoric methods to identify compounds responsible for the characteristic odor as well as partly for the folk medicinal use of this plant. Especially benzene derivatives, such as 1,4-dimethoxy benzene (24.9%), 1,2-dimethoxy benzene (10.6%) and 2-methoxy-4-methyl phenol (3.5%), the monoterpenes (Z)-linalool oxide (8.1%), (E)-linalool oxide (5.2%) and linalyl acetate (3.4%) as well as 1-octen-3-ol (9.5%) and isophorone (3.1%) were found to be main constituents (concentrations higher than 3%, calculated as relative %-peak area of GC-FID analysis using an apolar column) of this essential oil, with totally 69 compounds identified. In addition, the odor impression of the sample is described and the possible biological activity of single volatiles discussed.

Keywords

Biophytum Sensitivum (L.) DC.; Oxalidaceae; Essential Oil; Air-Dried Plant; Indian Folk Medicine.

Full Text

References

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Puri D. The insulintropic activity of a Nepalese medicinal plant Biophytum sensitivum: preliminary experimental study. J. Ethnopharmacol. 2001;78:89-93.

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Arctander S, editor. Perfume and Flavor Chemicals. Montclair:Published by the author, 1969.

Bauer K, Garbe D., Surburg, H. Common Fragrance and Flavor Material. Weinheim:VCH-Ver1agsges.m. b. H., 1997.

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Sigma-Aldrich. Flavors & Fragrances, The Essence of Excellence. Milwaukee:Sigma-Aldrich Co., 2001.

Buchbauer G, Jager W, Jirovetz L, llmberger J, Dietrich H. Therapeutic Properties of Essential Oils and Fragrances. In: Bioactive Volatile Compounds from Plants, ACS-Symposium-Series 525, 159-65. Washington:American Chemical Society, 1993.

Buchbauer G, Jirovetz L, Jager W, Plank C, Dietrich H. Fragrance Compounds and Essential Oils with Sedative Effects upon Inhalation. J. Pharm. Sci. 1993;82:660-4.

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Jirovetz L, Buchbauer G, Fleischhacker W, Ngassoum M B, Yonkeu S. Analysis of the Essential Oil of Stems and Leaves of Diplolophium africanum Turcz. from Cameroon. Acta Pharm. Turcica 1998;40:185-8.

Jirovetz L, Buchbauer G, Fleischhacker W. Analysis of the Essential Oil of the Leaves of the Medicinal Plant Chenopodium ambrosioides var. anthelminticum (L.) A. Gray from India. Sci. Pharm. 2000;68:123-8.

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Jirovetz L. Private retention-time listings.

Kondjoyan N, Berdaque J L. A Compilation of Relative Retention Indices for the Analysis of Aromatic Compounds. Saint Genes Champanelle:Edition du Laboratoire Flaveur, 1996.

Adams R P. Identification of essential oil components by gas chromatography/quadrupole mass spectroscopy. Carol Stream:Allured Publishing Corp., 2001.

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Jirovetz L. Private mass spectra libraries.

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Analysis, Chemotype and Quality Control of the Essential Oil of a New Cultivated Basil (Ocimum basilicum L.) Plant from Bulgaria

Abstract Views :203 | PDF Views:0

Authors

Leopold Jirovetz ¹, Gerhard Buchbauer ¹, Albena Stoyanova ², Anastasia Balinova ²

Affiliations
1 Institute of Pharmaceutical Chemistry, University of Vienna, Althanstrasse 14, A-1090 Vienna, AT
2 Higher Institute of Flavour Industries (HIFFI), Department of Essential Oils Maritza 26, 4002 Plovdiv, BG

Source

Scientia Pharmaceutica, Vol 69, No 1 (2001), Pagination: 85-89

Abstract

The essential oil of the spice plant Ocimum basilicum L. (Lamiaceae) from Bulgaria was investigated using gas chromatographic-spectroscopic (GC/FID and GC/MS: polar, non-polar and chiral phases of GC columns) and olfactoric methods. As main compounds of this basil oil sample (R)-(-)-linalool (71.4%), (Z,E)-α-farnesene (6.5%), 1,8-cineole (5.6%), τ-cadinol (2.8%), germacrene D (1.7%), citronellol (1.2%) and bornyl acetate (1.1%) were identified. Ths results show, that the essential basil oil from Bulgaria belongs to the European linalool chemotype. The correlations of olfactoric data (qualitative and quantitative) with the presented analytical ones certificate the good quality of this Bulgarian Ocimum basilicum sample. A possible use of this essential basil oil in medicine, perfumery and foods is discussed.

Keywords

Ocimum basilicum L.; Essential Oil; Volatiles; Composition; Chemotype; Quality Control; Possible Use

Full Text

References

Marotti, M., Piccaglia, R., Giovanelli, E., J. Agric. Food Chem. 44, 3926-3929 (1996).

Hiltunen, R., Holm, Y., Basil - The Genus Ocimum; harwood academic publishers, Amsterdam, The Netherlands (1999).

Yousif, A.N., Scaman, Ch.H., Durance, T.D., Girard, B., J. Agric. Food Chem. 47, 4777-4781 (1999).

BACIS, Volatile Compounds in Food (VCF)-Database, Boelens Aroma Chemical Information Service, Zeist, The Netherlands (1999).

Di Cesare, L.F., Nani, R., Viscardi, D., Brambilla, A., Bertolo, G., Fusari, E.L., Riv. Ital. EPPOS Ventin. 7, 29-37 (2000).

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Schrnaus, G., Thesis, University of Wiirzburg, Germany (1988).

Analysis of the Essential Oil of the Aerial Parts of the Medicinal Plant Aristolochia indica Linn. (Aristolochiaceae) from South-India

Abstract Views :219 | PDF Views:0

Authors

Leopold Jirovetz ¹, Gerhard Buchbauer ¹, Christiane Puschmann ¹, Wilhelm Fleischhacker ¹, P. Mohamed Shafi ², M. K. Rosamma ²

Affiliations
1 Institute of Pharmaceutical Chemistry, University of Vienna, Althanstrasse 14, A-1090 Vienna, AT
2 Department of Chemistry, Calicut University, Kerala 673 635, IN

Source

Scientia Pharmaceutica, Vol 68, No 3 (2000), Pagination: 309-316

Abstract

The essential oil of the aerial parts of Aristolochia indica Linn. (Anstolochiaceae) from South-India was analyzed by gas chromatographic-spectroscopic (GC-FID and GC-MS) and olfactoric methods to identify those compounds responsible for the characteristic odor as well as partly for the folk medicinal use of this plant. Especially sesqui - and monoterpenes were found to be dominating constituents of this essential oil, such as: β-caryophyllene, α-humulene, ishwarone, caryophyllene oxide I, ishwarol, ishwarane and aristolochene as well as linalool and α-terpinolene. The odor impression of the sample is described and the possible biological activity of some single volatiles shortly discussed.

Keywords

Aristolochia indica Linn., Anstolochiaceae, Essential Oil, Aerial Parts, Odor, Indian Folk Medicine.

Full Text

References

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Kondjoyan, N. and Berdaque, J.-L. (1996). A Compilation of Relative Retention Indices for the Analysis of Aromatic Compounds, Edition du Laboratoire Flaveur, Saint Genes Champanelle.

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Seasonal Depending Variations of the Composition and Biological Activities of Douglas Fir (Pseudotsuga menziesii) Essential Oils from Bulgaria

Abstract Views :164 | PDF Views:0

Authors

Leopold Jirovetz ¹, Gerhard Buchbauer ¹, Albena Stoyanova ², Stoyan Metodiev ²

Affiliations
1 Institute of Pharmaceutical Chemistry, University of Vienna Althanstrasse 14, A-1090 Vienna, AT
2 Higher Institute of Food and Flavour Industries, Department of Essential Oils, Maritza 26, 4002 Plovdiv, BG

Source

Scientia Pharmaceutica, Vol 68, No 3 (2000), Pagination: 323-328

Abstract

The seasonal depending variations of the essential oils of the needles with twigs of Bulgarian Douglas fir (Pseudotsuga menziesii, Pinaceae) were analyzed by GC-FID, GC-MS and olfactoric evaluation. In totally 8 investigated essential P. menziesii oils about 60 compounds could be identified with monoterpenes (especially sabinene and β-pinene) as main constituents. The antimicrobial effects against bacteria, fungi and worms of these volatiles as well as their olfactoric properties will be discussed.

Keywords

Pseudotsuga menziesii, Pinaceae, Essential Oil of the Needles With Twigs, GC-FID, GC-MS, Antimicrobial Activity.

Full Text

References

Buchbauer, G., Jirovetz, L., Wasicky, M., Nikiforov, A. (1994), J.Agric. Food Chem. 42: 2852.

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Stojanova, A., Metodiev, S., Karova, E., Posterpresentation (no. MM67) at the First Balcan Conference of Microbiology, Microbiologia Balkanica 99), Plovdiv (Bulgaria), October 5-9, 1999.

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Schrnaus, G. (1988). Thesis: Untersuchungen uber die Zusammensetzung der atherischen Wurzelole verschiedener mittel- und westeuropaischer Peucedanum-Arten (Apiaceae) unter besonderer Berucksichtigung von Peucedanum palustre (L.) Moench wnd Peucedanum lancfolium Lange, University of Wurzburg, Germany.

Analysis of the Essential Oil of the Leaves of the Medicinal Plant Chenopodium ambrosioides var. anthelminticum (L.) A. Gray from India

Abstract Views :172 | PDF Views:0

Authors

Leopold Jirovetz ¹, Gerhard Buchbauer ¹, Wilhelm Fleischhacker ¹, Vijay K. Kaul ²

Affiliations
1 Institute of Pharmaceutical Chemistry, University of Vienna Althanstrasse 14, A-1090 Vienna, AT
2 Institute of Himalayan Bioresource Technology, P.B. No. 6, Palampur (H.P.), 176 061, IN

Source

Scientia Pharmaceutica, Vol 68, No 1 (2000), Pagination: 123-128

Abstract

The composition of the essential oil of <I>Chenopodium ambrosioides var. anthelminticum</I> L. (Chenopodiaceae) leaves (also commonly known as American Wormseed, wormseed goosefood or sweet pig weed) from India (Himalayan area) was analyzed by GC-FID, GC-MS and olfactometry. As main compounds α-terpinene (65.4%) and para-cymene (29.4%) were found. Surprisingly the concentration of ascaridole, the main compound of <I>Chenopodium<I> species from various origin, was very low (0.7%) in this sample. The chromatographic-spectroscopic and olfactoric data as well as a possible influence of the identified volatiles on the reported biological effects will be discussed.

Keywords

Chenopodium ambrosioides var. anthelminticum; Chenopodiaceae; Essential Oil of the Leaves; GC-FID; GC-MS; α-Terpinene; Ascaridole.

Full Text

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Chemical Composition and Antibacterial Activities of the Essential Oils of Plectranthus glandulosus and Cinnumomum zeylrrnicum from Cameroon

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Authors

Leopold Jirovetz ¹, Gerhard Buchbauer ¹, Martin B. Ngassoum ², Jean J. Essia-Ngang ², Leopold N. Tatsadjieu ², Ousman Adjoudji ²

Affiliations
1 Institute of Pharmaceutical Chemistry, University of Vienna, Althanstrasse 13, A-1090 Vienna, AT
2 Department of Applied Chemistry, University of Ngaoundere, Ngaoundere, CM

Source

Scientia Pharmaceutica, Vol 70, No 1 (2002), Pagination: 93-99

Abstract

Two aromatic plants have been selected for chemical investigation on account of their antibacterial activities, Plectranthus glandulosus (fresh leaves) and Cinnamomum zeylanicum (dried leaves). P. glandulosus is used as a medicinal plant, while Cinnamomum zeylunicum is used as a common spice in many recipes in Cameroon. The essential oils of the plants have been obtained by hydrodistillation using a Clevenger type apparatus, the yields of oils are about 0.3% and 2.0% respectively. The essential oil of P. glandulosus contains mainly β-thujone (about 31%), p-cymen-8-ol (about 25%) and neral (about 10%) and the essential oil of C. zeylanicum is characterised by a high percentage of eugenol(85%). These essential oils have been tested against three strains of bacteria, namely Pseudomonas,fluorescens. Escherichia coli and Staphylococcus aureus; qualitative tests (diffusion through solid medium) and quantitative tests (dilution method) have been carried out. P. fluorescens shows a higher resistance to the two oils (MIC values not less than 5000 ppm). E. coli is more sensitive to these oils, while against S. aureus the essential oil of C. zeylanicum still shows a high activity (3500 ppm). The antibacterial activities of the essential oils could be attributed to the components eugenol as the active component of C. zeylanicum and β-thujone and p-cymen-4-ol of the essential oil of P. glandulosus.

Keywords

Plectranthus glandulosus; Cinnamomum zeylanicum; Essential Oils; Antibacterial Activity, Composition.

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Antimicrobial Testinqs, Gas Chromatoqraphic Analysis and Olfactorv Evaluation of an Essential Oil of Hop Cones (Humulus lupulus L.) from Bavaria and some of its main Compounds

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Authors

Leopold Jirovetz ¹, Stefanie Bail ¹, Gerhard Buchbauer ¹, Zapriana Denkova ², Alexander Slavchev ², Albena Stoyanova ³, Erich Schmidt ⁴, Margit Geissler ⁵

Affiliations
1 Department of Clinical Pharmacy and Diagnostics, University of Vienna, Althanstrasse 14, A-1090 Vienna, AT
2 University of Food Technology, Department of Microbiology, 26 Maritza Boulevard, 4002 Plovdiv, BG
3 University of Food Technology, Department of Essential Oils, 26 Maritza Boulevard, 4002 Plovdiv, BG
4 Kurt Kitzing GmbH, Hinterm Alten Schloss 21, D-86757 Wallerstein, DE
5 Department of GC and GC/MS, Albert-Hahn-Strasse 6-10, D-47269 Duisburg, DE

Source

Scientia Pharmaceutica, Vol 74, No 4 (2006), Pagination: 189-201

Abstract

The essential oil of hop cones (Humulus lupulu L.) was analyzed by GC and GC-MS to assess the composition of volatiles and to evaluate olfactorially the principle aroma compounds. Myrcene (45.3%), α-humulene (31.2%) and β-caryophyllene (9.8%) were found to be the main constituents of this H. lupulus sample. The essential hop oil, the 3 main compounds and three minor concentrated constituents, isobutyl isobutyrate, geraniol and β-pinene, were tested for their antimicrobial activities against some different strains of Gram-positive and Gram-negative bacteria as well as the yeast Candida albicans by using agar diffusion and agar dilution method, respectively. The same was done using the phenolic aroma compound eugenol and the synthetic antibiotics ciproxin^R, Lidaprim^R and tetracycline hydrochloride as reference-substance. It was found that the essential H. lupulus oil showed antimicrobial activities against the Gram-positive-bacteria Staphylococcus aureus and Enterococcus faecalis, the Gram-negative-bacteria Escherichia coli and Salmonella sp. as well as the yeast Candida albicans. This result was correlated to the antimicrobial testing of the mentioned main and minor constituents of the essential hop oil as well as of the 4 reference-compounds. The obtained data were discussed to get more insight into the influence of pure aroma compounds on the antimicrobial activities of essential oils.

Keywords

Humulus lupulus L., Cones, Essential Oil, Composition, Antimicrobial Testing, Olfactory Evaluation, GC, GC-MS.

Full Text

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