Startseite Chemical composition and microbiological evaluation of essential oil from Hyssopus officinalis L. with white and pink flowers
Artikel Open Access

Chemical composition and microbiological evaluation of essential oil from Hyssopus officinalis L. with white and pink flowers

  • Tomasz Baj EMAIL logo , Izabela Korona-Głowniak , Radosław Kowalski und Anna Malm
Veröffentlicht/Copyright: 23. April 2018

Abstract

Hyssopus officinalis L. is a common plant that is most usually found in three color forms - f. cyaneus (blue), f. ruber Mill. (purple/pink) and f. albus Alef (white). In the present work, we evaluated the chemical composition and antimicrobial activity of essential oils obtained from Polish-sourced white- and pink-flowered H. officinalis. Gas chromatography-mass spectrometry analysis of the essential oil has shown that both forms of color have a different content of main components. The principle essential oil component of white-flowered H. officinalis L. was pinocamphone (51%), while pink-flowered H. officinalis L. contained almost equal amounts of pinocamphone (28.8%) and isopinocamphone (21.9%). Of note, the essential oil of the pink form was more active against Grampositive bacteria, especially against Bacillus subtilis.

1 Introduction

Hyssop (Hyssopus officinalis L.), while grown in many countries around the world, is a plant native to southwestern Asia and southern Europe. Due to its camphor aroma and bitter taste, it is often used as a kitchen spice. In both the fresh and the dried state, it is also a supplement to salads, meats, vegetables, cottage cheese and pâté. Moreover, in the production of vermouth and bitter liqueurs (Chartreuse and Benedictine) hyssop supplies the unique spicy taste [1,2].

Hyssop blooms come mainly in three color forms: f. cyaneus Alef. – with blue crown petals (the most popular variety), f. ruber Mill – with purple (pink) crown petals, and f. albus Alef. – with white flowers [3]. The correlation between the chemical composition of the essential oil and the color of hyssop flowers is rarely described [3,4]. However, genotypic variability studies have shown variations between phenotypes [5,6]

Hyssop is an aromatic plant, although the composition of essential oil is not homogeneous. Literature data on the composition of the essential oil of H. officinalis exhibits major differences in the content thereof. As the main ingredient, the authors most often noted reference to isopinocamphone [7,8,9,10,11,12,13,14,15,16,17,18,19,20], pinocamphone [21,22,23], myrtenyl acetate [24], α-pinene [25], 1,8-cineole [26], pinocarvone [27] and linalool [28]. The ISO 9841: 2007 standard for hyssop oil specifies the highest content for: isopinocamphone (25-45%), pinocamphone (8.0-25%) and β-pinene (7.0-20.0%) [29].

The aim of this work was to evaluate the chemical composition and antimicrobial activity of essential oil obtained from Poland white and pink-flowered H. officinalis L. The present work is a continuation of previous research [7,30].

2 Experimental

2.1 Plant material

Flowering shoots (30 cm from the top) in full bloom of H. officinalis were collected from the Botanical Garden of the Department of Pharmacognosy, Medicinal Plant Unit, Medical University of Lublin (22°33’50.868”E, 51°15’22.8312”N, 187 m above sea level) during August, 2013 (Photo 1). The plant material was identified by Dr. Elwira Sieniawska, a Medicinal Plant Unit employee. All raw material was then dried at room temperature. Specimen HOW2013/HOP2013 is deposited above the Department of Pharmacognosy.

Photo 1 Hyssopus officinalis L. with white (A) and pink (B) flowers (Medicinal Plant Unit of Medical University, Lublin, Poland).
Photo 1

Hyssopus officinalis L. with white (A) and pink (B) flowers (Medicinal Plant Unit of Medical University, Lublin, Poland).

2.2 Extraction of essential oils

Essential oil hydro-distillation was carried out using a Deryng apparatus according to the previously described procedure [31]. Herein, 40 g of air-dried plant material plus 500 ml distilled water underwent 3 h distillation. Subsequently, anhydrous sodium sulfate was used to remove the water after extraction. The hyssop essential oils (HEO) were then collected into dark glass bottles and stored in a refrigerator at 4°C. The distillation of the essential oil was repeated 3 times.

2.3 Gas chromatography

Chromatographic analysis was carried out according to the previously described procedure [32]. In so doing, a GC-MS: ITMS Varian 4000 GC-MS/MS (Varian, USA) equipped with a CP-8410 auto-injector and a 30 m × 0.25 mm VF-5ms column (Varian, USA) was used. In this study, film thickness was 0.25 μm, carrier gas was He 0.5 ml/min, injector and detector temperature were, respectively, at 250 and 200°C; split ratio was 1:50; and inject volume was 5 μl. A temperature gradient was first applied (50°C) for 1 minute, then increased by 4°C/min to 250°C, with 250°C held for 10 minutes. The ionization energy was 70 eV;the range recorded was 35-1000 m/z and the scan rate was 0.80 s per scan. Data acquisition and processing, and instrumental control were performed by the Varian MS Workstation Version 6.42.

Subsequently, a GC/FID GC Varian 3800 (Varian, USA) equipped with a CP-8410 auto-injector and a 30 m × 0.25 mm DB-5 column (J&W Scientific, USA) was employed. The film thickness was 0.25 μm, the carrier gas was He 0.5 ml/min, injector and detector FID temperatures were 260°C; split ratio was 1:100; and injection volume was 5 μl. A temperature gradient was then applied (50°C for 1 minute, then increased by 4°C/min to 250°C, with 250°C held for 10 minutes).

Qualitative analysis was carried out via MS spectra, these were compared with the spectra library by means of the NIST MS Search Program (NIST 08, 2005), as well as with the data available in literature [33]. Identity of the compounds was confirmed by their retention indices, wherein the retention indices were determined in relation to a homologous series of n-alkanes (C10–C40 ) under the same operating conditions. Retention indices were also compared with literature data [34,35,36,37]. The percentages of main components of the essential oil were presented assuming that the sum of peak areas for all identified constituents is 100%.

2.4 Antimicrobial activity

Essential oils from the two color forms of H. officinalis were screened for antibacterial and antifungal activities by way of the micro-dilution broth method, using Mueller-Hinton broth either as Mueller-Hinton broth with 5% lysed sheep blood for growth of non-fastidious and fastidious bacteria, respectively, or as Mueller-Hinton broth with 2% glucose for growth of fungi. Minimal inhibitory concentration (MIC) of tested essential oils were evaluated for the panel of the reference microorganisms which belonged to the American Type Culture Collection (ATCC), including Gramnegative bacteria (Escherichia coli ATCC 25922, Klebsiella pneumoniae ATCC 13883, Pseudomonas aeruginosa ATCC 9027, Proteus mirabilis ATCC 12453), Gram-positive bacteria (Staphylococcus aureus ATCC 25923, S. aureusATCC 6538, S. epidermidis ATCC 12228, Bacillus subtilis ATCC 6633, Micrococcus luteus ATCC 10240, Streptococcus pyogenes ATCC19615, S. pneumoniae ATCC49619, S. mutansATCC25175) and fungi (Candida albicans ATCC 10231, C. parapsilosis ATCC 22019).

Stock cultures were maintained at -70oC in Tripticase Soy broth (containing 16% (v/v) glycerol) for bacteria, and Sabouraud dextrose broth (containing 16% (v/v) glycerol) for yeasts, until the study was performed. Before the experiments, each bacterial and yeast strain was passaged onto fresh Mueller-Hinton agar or Mueller-Hinton agar with 5% lysed sheep blood at 35° for 24 h, and onto Sabouraud dextrose agar at 30° for 48 h, respectively.

The essential oils dissolved in dimethylosulfoxide (DMSO), were first diluted to the concentration (10 mg/ml) in the aforementioned and recommended broths for determining the antibacterial and antifungal activity. Subsequently, using the same media, serial two-fold dilutions were made in order to obtain final concentrations of plant extracts ranging from 0.156 to 10 mg/ml. The sterile 96-well polystyrene microtitrate plates (Nunc, Denmark) were prepared by dispensing 200 μl of appropriate dilution of plant material in culture broth per well. The inocula were then prepared with fresh microbial cultures in sterile 0.85% NaCl to match the turbidity of 0.5 McFarland standard, and 2 μl were added to the wells to obtain a final density of 1.5 × 106 CFU/ml and 5 × 104 CFU/ ml for bacteria and yeasts, respectively. After incubation (35°C for 18-24 h), the MICs were assessed visually as the lowest oil concentration showing complete inhibition in the growth of the tested microorganisms. Appropriate DMSO (at a final concentration 10%), a positive control (containing inoculum without plant material) and negative control (containing plant material without inoculum) were included on each microplate. Reference compounds – vancomycin, ciprofloxacin for bacteria and fluconazole for yeasts were purchased from Sigma-Aldrich, (St. Louis, USA).

Minimal bactericidal concentration (MBC) or minimal fungicidal concentration (MFC) was obtained by subculturing 5 μl from each well that showed thorough growth inhibition, from the last positive one and from the growth control onto recommended agar plates. The plates were incubated at 35°C for 24 h and the MBC/MFC was defined as the lowest concentration of essential oil without growth of microorganisms. Each experiment was repeated in triplicate.

2.5 Statistical analysis

The average values of the component contents were calculated using Excel (Microsoft, USA).

Ethical approval: The conducted research is not related to either human or animals use.

3 Results and discussion

The HEO content obtained via hydrodistillation was (on average) 0.7% of total dry weight for white-flowered plants (HWF) and 0.5% of total dry weight for pink-flowered plants (HPF). In the oil of the HWF form, 44 components were identified, and in HPF – 49 components. The percentages of chemical constituents of essential oils are shown in Table 1.

Table 1

Percentage composition of essential oil obtained from white- (HWF) and pink- (HPW) flowered Hyssopus officinalis L.

NoCompoundRI exp.[*]RI lit.[**]HWF[***]HPF[***]
1α-Thujene979979[a]0.50.4
2α-Pinene981981[a]1.00.7
3Camphene986986[a]0.20.2
4Sabinene993993[a]3.02.2
5β-Pinene995994[a]12.49.8
63-Octanone996996[b]0.30.0
7Myrcene997997[b]3.91.7
8α-Terpinene10191019[c]0.10.2
9p-Cymene10261028[d]0.10.0
10Limonene10311031[c]1.41.0
111,8-Cineole10331035[c]7.61.9
12β-Ocimene10451050[d]0.41.0
13γ-Terpinene10581062[d]0.10.1
14cis-Sabinene hydrate10701070[d]0.20.1
15Terpinolene10851085[c]0.10.1
16Linalool10971099[c]0.10.8
17trans-Sabinene hydrate11011102[c]0.10.0
18cis-Thujone11071108[d]tr0.1
19trans-Thujone11191120[d]0.50.4
20cis-p-Menth-2-en-1-ol11261129[c]0.10.0
21trans-Pinocarvel 11451143[a]0.30.1
22trans-p-Menth-2en-1-ol- 11591149[c]8.10.4
23Pinocamphone11671167[d]51.028.8
24Borneol11791176[a]0.10.0
25Isopinocamphorie 11841175[d]1.921.9
26Myrtenol12031196[d]0.64.7
27Myrtenyl acetate13321327[d]-0.1
28Δ-Elemene13421338[d]0.10.1
29α-Copaene13841377[d]0.00.1
30β-Bourbonene13921388[d]0.20.8
31β -Elemene13961391[d]0.10.2
32Methyl eugenol14041402[a]-0.4
33α-Gurjunene14181410[d]-0.1
34β-Caryophyllene14331429[d]1.00.9
35β-Copaene14441432[d]0.00.1
36α-Guaiene14611440[d]0.00.1
37α-Humulene14741455[d]0.20.2
38Alloaromadendreie 14791473[d]0.00.2
39Germacrene D14881495[d]0.00.1
40γ-Amorphene15021506[c]1.75.2
41Bicyclogermacrene 15151507[d]2.03.3
42γ-Cadinene15301514[d]0.00.1
43Elemol15611560[d]-5.4
44Spathulenol15891589[d]0.31.0
45Viridiflorol15981606[a]0.10.8
46Ni.1619-0.00.8
47γ-Eudesmol16481632[d]0.01.3
48epi-alpha-Cadino16571640[d]0.10.6
49A - Eudesmol16751675[c]0.11.6
50Bulnesol16831672[d]-0.2
Total identified99.699.0
Grouped compounds (%)
Monoterpene hydrocarbons23.217.4
Oxygenated monoterpenes70.659.3
Sesquiterpene hydrocarbons4.910.2
Oxygenated sesquiterpenes0.610.9
Other compounds0.31.2
  1. Ni. – unidentified compound.

Main HEO component-content may vary depending on the plant developmental stage, the age of the plant, the manner and place of cultivation and date of harvest, the plant part harvested and way of distillation, as well as the phenotype. During the development of the plant, the main constituents of the essential oil vary: pinocamphone dominates before flowering, and, during flowering, isopinocamphone [37]. Regarding the age of the plant, first year plants exhibit higher pinocamphone content, while isopinocamphone content dominates in three-year-old plants [22]. As to the manner of cultivation, Tavakoli and Aghajani [38] saw that the main ingredients of H. officinalis (pinocamphone or isopinocamphone) varied depending on the degree of irritation. Regarding altitude of cultivation, Fraternale et al. [39], in assessing the influence of climate on the content of the main components, noted that the oil obtained from the raw material growing below the 100 m above sea level contour contained a higher percentage of pinocamphone, while the oil obtained from the 1000 m above sea level contour contained a higher level of isopinocamphone. Moreover, the oil obtained from plants planted below the 100 m contour contained a much lower percentage of linalool and camphor compared to the oil obtained from plants grown at higher altitudes. Regarding the plant parts, the main components of the HEO were isopinocamphone (49.7-57.7%) in all parts of the plant, while β-pinene and pinocarvone concentrations were variable for each organ, and pinocamphone content never exceeded 1.5% [39]. As to place of occurrence, according to literature, the main HEO component content may vary depending on the place of occurrence, even in a small area. In the study of Bernotiene & Butkiene [27], isopinocamphone (33.6 and 16.8%) was the main constituent in two sites, and pinocarvone (21.1 and 28.1%) was the main component in another two sites. Wesolowska et al. [40], when comparing methods of obtaining HEO (hydrodistillation and steam distillation) did not find significant differences in the isopinocamphone content (the main ingredient). This varied, however, from 40.07% to 45.45% depending on the method. With regard to phenotype, the chemical composition of the three forms of H. officinalis growing in Yugoslavia was found to be predominantly pinocamphone, isopinocamphone and pinocarvone [3]. Phenotypic variability in the composition of essential oils was also found in the hyssop growing in Moldova. Herein, the principal HEO components in the examined forms were isopinocamphone and pinocamphone [4]. In the present study, pinocamphone (51%) was the dominating compound in the essential oil of white flowers, while in pink flowers, the content of pinocamphone and isopinocamphone was comparatively 28.7% and 21.9%, respectively.

A comparison of the chemical composition of the essential oils from white- and pink-flowered H. officinalis with literature data suggests that the forms present in Poland are f. albus Alef. and f. ruber Mill. However, further taxonomic studies are needed.

The essential oils from the two cultivars of hyssop growing in Poland, showed moderate activity against Streptococcus pyogenes, S. pneumoniae, S. mutans, Candida albicans and C. parapsilosis, and poor activity against Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Proteus mirabilis, Staphylococcus aureus, S. epidermidis, Bacillus subtilis and Micrococcus luteus (Table 2).

Table 2

Antimicrobial activity of essential oil obtained from white- (HWF) and pink- (HPW) flowered Hyssopus officinalis L. and reference compounds – vancomycin, ciprofloxacin for bacteria and fluconazole for yeasts.

HWFHPFReference compounds
MIC (mg/ml)MBC (mg/ml)MIC (mg/ml)MBC (mg/ml)MIC (μg/ml)MBC (μxg/ml)
Gram-positive bacteriaVancomycin
Staphylococcus aureus ATCC2592310205100.987.81
Staphylococcus epidermidis ATCC122285102.550.980.98
Micrococcus luteus ATCC102402.552.550.120.12
Bacillus subtilis ATCC6633550.6252.50.240.49
Streptococcus pyogenes ATCC196150.6251.250.3120.6250.240.49
Streptococcus pneumoniae ATCC496190.6251.250.3120.6250.240.49
Streptococcus mutans ATCC251751.251.250.6251.250.980.98
Gram-negative bacteriaCiprofloxacin
Escherichia coli ATCC25922510550.0040.004
Proteus mirabilis ATCC124535105100.030.03
Klebsiella pneumoniae ATCC138835105100.120.12
Pseudomonas aeruginosa ATCC90275105100.490.98
YeastFluconazole
Candida albicans ATCC1022310.6252.50.6252.50.981.95
Candida parapsilosis ATCC220191.2550.6251.251.951.95

The essential oils from pink-flowered H. officinalis was more active against bacteria Gram-positive: Staphylococcus aureus, S. epidermidis, Streptococcus pyogenes, S. pneumoniae and S. mutans. Moreover, it reveals exceptional activity against Bacillus subtilis. The activity of the essential oil against bacteria Gram-negative and yeast of the Candida spp. were similar. Tested essential oils showed lower activity compared to the reference components.

The antimicrobial properties of essential oils depend on a whole group of compounds having very different chemical structures, therefore, the essential oil antimicrobial effects can be explained through several diverse mechanisms. Probably the high lipophilicity of essential oils is very significant because it determines the cell and mitochondrial membrane penetrative qualities (considered as ‘good’), the disruption of the structure and functions of the membranes, as well as the enhanced permeability [41]. Furthermore, in studies conducted by Hristova et al. [42], pinocamphnone, isopinocamphone, α- and β-pinene HEO show synergistic effects against Candida spp. The essential oil obtained from the hyssop showed a stronger activity than did pure ingredients.

Dehghanzadeh et al. [43] analyzed the composition and antimicrobial properties of the essential oil obtained from H. officinalis growing in Iran, and found it chemically different from the previously described hyssop oils. GC/MS analysis showed that the main components of this oil were thymol> β-bisabolol> carvacrol. This oil showed high antibacterial activity against Klebsiella sp. and Erwinia amylovora (responsible for the occurrence of fire blight on pear and apple crops) and no activity against Staphylococcus aureus, Escherichia coli, Bacillus subtilis, Xannthomonas axonopodis pv citri, Acidovorax sp. Streptomyces scabies and Pseudomonas florescence. Antibacterial and antioxidant properties of the essential oil obtained from H. officinalis grown in Turkey were studied by Kizil et al. [10]. They showed that the chemotype is rich in isopinocamphone> β-pinene> terpinen-4-ol, and was active against Streptococcus pyogenes, Staphylococcus aureus, Candida albicans and Escherichia coli, while there was no activity against Pseudomonas aeruginosa.

As revealed, hyssop-derived essential oils have different antimicrobial activity. However, the use of pure oil may be limited due to its neurotoxicity [44], and HEO oil is contraindicated in patients with epilepsy and during pregnancy.

4 Conclusions

An analysis of essential oils of the two flower forms of Hyssopus officinalis L. grown in Poland with white and pink flowers showed different chemotypes. A comparison of the obtained results and the literature data indicate that the essential oil from white-flowered plants contains mainly pinocamphone and β-pinene, whereas oil obtained from pink-flowered plants contained almost equal amounts of pinocamphone and isopinocamphone.

  1. Conflict of interest: Authors state no conflict of interest.

References

[1] Hoope HA., Drogenkunde I., Valter de Gruyter Verl. Eds. Berlin-New-York, 1975.Suche in Google Scholar

[2] Charles D.J., Hyssop. In: Antioxidant Properties of Spices, Herbs and Other Sources. Springer, New York, NY, 2012.10.1007/978-1-4614-4310-0_31Suche in Google Scholar

[3] Chalchat J.C., Adamovic D., Gorunovic M.S., Composition of oils of three cultivated forms of Hyssopus officinalis endemic in Yugoslavia: f. albus Alef., f. cyaneus Alef. and f. ruber Mill., J. Essent. Oil Res., 2001, 13(6), 419-421.10.1080/10412905.2001.9699712Suche in Google Scholar

[4] Gonceariuc M., Hyssopus officinalis L. genotypes with different content and composition of essential oil, Buletinul ASM. Stiintele vietii, 2013, 1(319), 86-96.Suche in Google Scholar

[5] Németh-Zámbori É., Rájhart P., Inotai K., Effect of genotype and age on essential oil and total phenolics in hyssop (Hyssopus officinalis L.), J. Appl. Bot. Food Qual., 2017, 90, 25-30.Suche in Google Scholar

[6] Mutu A., Clapco S., Martea R., Port A., Duca, M., Intraspecific genetic variability of Hyssopus officinalis L., Analele Stiintifice ale Universitatii Al. I. Cuza Din Iasi-Serie Noua-Sectiunea II A Genetica si Biologie Moleculara, 2014, 15(3), 1-8.Suche in Google Scholar

[7] Baj T., Kowalski R., Swiatek L., Modzelewska M., Wolski T., Chemical composition and antioxidant activity of the essentials oil of hyssop (Hyssopus officinalis L. ssp. officinalis), Annales UMCS, 2010, 23, 55-62.Suche in Google Scholar

[8] Nikolić M., Marković T., Marković D., Glamoclija J., Ćirić A., Smiljković, M., Soković M., Antimicrobial activity of three Lamiaceae essential oils against common oral pathogens, Balk. J. Dent. Med., 2016, 20(3), 160-167.10.1515/bjdm-2016-0026Suche in Google Scholar

[9] De Martino L., De Feo V., Nazzaro F., Chemical composition and in vitro antimicrobial and mutagenic activities of seven Lamiaceae essential oils, Molecules, 2009, 14(10), 4213-4230.10.3390/molecules14104213Suche in Google Scholar

[10] Kizil S., Hasimi N., Tolan V., Karatas H., Chemical composition, antimicrobial and antioxidant activities of hyssop (Hyssopus officinalis L.) essential oil, Notulae Botanicae Horti Agrobotanici Cluj-Napoca, 2010, 38(3), 99.Suche in Google Scholar

[11] Kizil S., Toncer O., Ipek A., Arslan N., Saglam S., Mahmood Khawar K., Blooming stages of Turkish hyssop (Hyssopus officinalis L.) affect essential oil composition. Acta Agr. Scand. Sect. B Soil Plant Sci., 2008, 58(3), 273-279.10.1080/09064710701647297Suche in Google Scholar

[12] Myadelets M.A., Domrachev D. V., Cheremushkina V.A., A study of the chemical composition of essential oils of some species from the Lamiaceae family cultivated in the Western Siberian Region, Russ. J. Bioorg. Chem., 2013, 39(7), 733-738.10.1134/S1068162013070091Suche in Google Scholar

[13] Said-Al Ahl H.A., Abbas Z.K., Sabra A.S., Tkachenko K.G., Essential oil composition of Hyssopus officinalis L. cultivated in Egypt. Int. J. Plant Sci. Ecol., 2015, 1(2), 49-53.Suche in Google Scholar

[14] Mitic V., Dordevic S., Essential oil composition of Hyssopus officinalis L. cultivated in Serbia, Facta universitatis-series: Physics, Chemistry and Technology, 2000, 2(2), 105-108.Suche in Google Scholar

[15] De Almeida L.F.R., Frei F., Mancini E., De Martino L., De Feo V., Phytotoxic activities of Mediterranean essential oils, Molecules, 2010, 15(6), 4309-4323.10.3390/molecules15064309Suche in Google Scholar

[16] Cvijovic M., Djukic D., Mandic L., Acamovic-Djokovic G., Pesakovic M., Composition and antimicrobial activity of essential oils of some medicinal and spice plants. Chem. Nat. Compd., 2010, 46(3), 481-483.10.1007/s10600-010-9652-zSuche in Google Scholar

[17] Mazzanti G., Battinelli L., Salvatore G., Antimicrobial properties of the linalool-rich essential oil of Hyssopus officinalis L. var. decumbens (Lamiaceae). Flavour Fragr. J., 1998, 13(5), 289-294.10.1002/(SICI)1099-1026(1998090)13:5<289::AID-FFJ750>3.0.CO;2-ASuche in Google Scholar

[18] Jianu C., Golet I., Misca C., Jianu A.M., Pop G., Gruia A.T., Antimicrobial properties and chemical composition of essential oils Isolated from six medicinal plants grown in Romania Against Foodborne Pathogens, Rev. Chim. (Bucharest), 2016, 67(6), 1056-1061.Suche in Google Scholar

[19] Mohan M., Seth R., Singh P., Lohani H., Gupta S., Composition of the volatiles of Hyssopus officinalis (L.) and Thymus serpyllum (L.) from Uttarakhand Himalaya, Natl. Acad. Sci. Lett., 2012, 35(5), 445-448.10.1007/s40009-012-0075-1Suche in Google Scholar

[20] Kizil S., Güler V., Kirici S., Turk, M., Some agronomic characteristics and essential oil composition of hyssop (Hyssopus officinalis L.) under cultivation conditions. Acta Sci Polon-Hort Cultus, 2016, 15(6), 193-207.Suche in Google Scholar

[21] Garg S.N., Naqvi A.A., Singh A., Ram G., Kumar S., Composition of essential oil from an annual crop of Hyssopus officinalis grown in Indian plains. Flavour Fragr. J., 1999, 14(3), 170-172.10.1002/(SICI)1099-1026(199905/06)14:3<170::AID-FFJ808>3.0.CO;2-QSuche in Google Scholar

[22] Kotyuk L.A., Hyssop composition depending on age and plants development phases, Biotechnol. Acta, 2015, 8(5), 55-63.10.15407/biotech8.05.055Suche in Google Scholar

[23] Khan R., Shawl A.S., Tantry M.A., Determination and seasonal variation of chemical constituents of essential oil of Hyssopus officinalis growing in Kashmir valley as incorporated species of Western Himalaya. Chem. Nat. Compd., 2012, 48(3), 502-505.10.1007/s10600-012-0290-5Suche in Google Scholar

[24] Fathiazad F., Mazandarani M., Hamedeyazdan S., Phytochemical analysis and antioxidant activity of Hyssopus officinalis L. from Iran, Adv. Pharm. Bull., 2011, 1(2), 63-67.Suche in Google Scholar

[25] Ogunwande I.A., Flamini G., Alese O.O., Cioni P.L., Ogundajo A., Setzer W.N., A new chemical form of essential oil of Hyssopus officinalis L.(Lamiaceae) from Nigeria. Int. J. Biol. Chem. Sci., 2011, 5(1), 46-55.10.4314/ijbcs.v5i1.68084Suche in Google Scholar

[26] De Elguea-Culebras G.O., Sánchez-Vioque R., Berruga M.I., Herraiz-Peñalver D., González-Coloma A., Andrés M.F., Santana-Méridas O., Biocidal potential and chemical composition of industrial essential oils from Hyssopus officinalis, Lavandula x intermedia var. super and Santolina chamaecyparissus. Chem Biodiversity. 2017, Accepted Author Manuscript. 10.1002/cbdv.201700313Suche in Google Scholar

[27] Bernotiene G., Butkiene R., Essential oils of Hyssopus officinalis L. cultivated in East Lithuania. Chemija, 2010, 21(2-4), 135-138.Suche in Google Scholar

[28] Venditti A., Bianco A., Frezza C., Conti F., Bini L. M., Giuliani C. et al., Essential oil composition, polar compounds, glandular trichomes and biological activity of Hyssopus officinalis subsp. aristatus (Godr.) Nyman from central Italy. Ind. Crops Prod., 2015, 77, 353-363.10.1016/j.indcrop.2015.09.002Suche in Google Scholar

[29] Moro A., Zalacain A., Hurtado de Mendoza J., Carmona M., Effects of agronomic practices on volatile composition of Hyssopus officinalis L. essential oils, Molecules, 2011, 16(5), 4131-4139.10.3390/molecules16054131Suche in Google Scholar

[30] Baj T., Sieniawska E., Kowalski R., Swiatek L., Modzelewska M., Wolski T., Chemical composition and antioxidant activity of the essentials oil of hyssop (Hyssopus officinalis L. ssp. officinalis).Part II. Free radical scavenging properties, Annales UMCS, 2011, 24, 103-109.Suche in Google Scholar

[31] Baj T., Ludwiczuk A., Sieniawska E., Skalicka-Woźniak K., Widelski J., Zieba K., Głowniak K., GC-MS analysis of essential oils from Salvia officinalis L.: comparison of extraction methods of the volatile components, Acta Polon. Pharm., 2013, 70(1), 35-40.Suche in Google Scholar

[32] Kowalski R., Baj T., Kowalska G., Pankiewicz U., Estimation of potential availability of essential oil in some brands of herbal teas and herbal dietary supplements, PloS One, 2015, 10(6), e0130714.10.1371/journal.pone.0130714Suche in Google Scholar

[33] Adams R.P., Identification of essential oil components by gas chromatography/mass spectrometry. 4th edn. Allured Publ. Corp, Carol Stream, 2007.Suche in Google Scholar

[34] Zawislak G., Nurzynska-Wierdlak R., Plant development and chemical composition of essential oil of yarrow (Achillea millefolium L.) cultivated under temperate climate. Annales Hort. 2017, 31-38.Suche in Google Scholar

[35] Nurzynska R., Zawislak G., Chemical composition and antioxidant activity of lavender (Lavandula angustifolia Mill.) aboveground parts. Acta Sci. Pol. Hortorum Cultus, 15(5) 2016, 225-241.Suche in Google Scholar

[36] Marzec M., Polakowski C., Chilczuk R., Kołodziej B., Evaluation of essential oil content, its chemical composition and price of thyme (Thymus vulgaris L.) raw material available in Poland. Herba Pol., 2010, 56(3), 37-52.Suche in Google Scholar

[37] Zawislak G., The chemical composition of essential hyssop oil depending on plant growth stage. Acta Sci. Pol. Hortum Cultus, 2013, 12(3), 161-170.Suche in Google Scholar

[38] Tavakoli M., Aghajani Z., The effects of drought stress on the components of the essential oil of Hyssopus officinalis L. and determining the antioxidative properties of its water extracts. J. Appl. Environ. Biol. Sci., 2016, 6(2), 31-36.Suche in Google Scholar

[39] Fraternale D., Ricci D., Epifano F., Curini M., Composition and antifungal activity of two essential oils of hyssop (Hyssopus officinalis L.). J. Essent. Oil Res., 2004, 16(6), 617-622.10.1080/10412905.2004.9698810Suche in Google Scholar

[40] Wesołowska A., Jadczak D., Grzeszczuk M., Essential oil composition of hyssop (Hyssopus officinalis L.) cultivated in north-western Poland. Herba Pol., 2010, 56(1), 57-65.Suche in Google Scholar

[41] Burt S., Essential oils: their antibacterial properties and potential applications in foods – a review, Int. J. Food Microb., 2004, 94(3), 223-253.10.1016/j.ijfoodmicro.2004.03.022Suche in Google Scholar

[42] Hristova B.Y., Wanner J., Jirovetz L., Stappen I., Iliev I., Gochev V., Chemical composition and antifungal activity of essential oil of Hyssopus officinalis L. from Bulgaria against clinical isolates of Candida species, Biotechnol. Biotechnol. Equip. 2015, 29(3), 592-601.10.1080/13102818.2015.1020341Suche in Google Scholar

[43] Dehghanzadeh N., Ketabchi S., Alizadeh A., Essential oil composition and antibacterial activity of Hyssopus officinalis L. grown in Iran, Asian J. Biol. Sci, 2012, 3(4), 767-771.Suche in Google Scholar

[44] Tisserand R., Essential oil safety II: Metabolism, neurotoxicity, reproductive toxicity., Int. J. Aromather., 1996, 7(4), 26-29.10.1016/S0962-4562(96)80028-2Suche in Google Scholar

Received: 2017-11-22
Accepted: 2018-03-02
Published Online: 2018-04-23

© 2018 Tomasz Baj et al., published by De Gruyter

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

Artikel in diesem Heft

  1. Regular Articles
  2. The effect of CuO modification for a TiO2 nanotube confined CeO2 catalyst on the catalytic combustion of butane
  3. The preparation and antibacterial activity of cellulose/ZnO composite: a review
  4. Linde Type A and nano magnetite/NaA zeolites: cytotoxicity and doxorubicin loading efficiency
  5. Performance and thermal decomposition analysis of foaming agent NPL-10 for use in heavy oil recovery by steam injection
  6. Spectroscopic (FT-IR, FT-Raman, UV, 1H and 13C NMR) insights, electronic profiling and DFT computations on ({(E)-[3-(1H-imidazol-1-yl)-1-phenylpropylidene] amino}oxy)(4-nitrophenyl)methanone, an imidazole-bearing anti-Candida agent
  7. A Simplistic Preliminary Assessment of Ginstling-Brounstein Model for Solid Spherical Particles in the Context of a Diffusion-Controlled Synthesis
  8. M-Polynomials And Topological Indices Of Zigzag And Rhombic Benzenoid Systems
  9. Photochemical Transformation of some 3-benzyloxy-2-(benzo[b]thiophen-2-yl)-4Hchromen-4-ones: A Remote Substituent Effect
  10. Dynamic Changes of Secondary Metabolites and Antioxidant Activity of Ligustrum lucidum During Fruit Growth
  11. Studies on the flammability of polypropylene/ammonium polyphosphate and montmorillonite by using the cone calorimeter test
  12. DSC, FT-IR, NIR, NIR-PCA and NIR-ANOVA for determination of chemical stability of diuretic drugs: impact of excipients
  13. Antioxidant and Hepatoprotective Effects of Methanolic Extracts of Zilla spinosa and Hammada elegans Against Carbon Tetrachlorideinduced Hepatotoxicity in Rats
  14. Prunus cerasifera Ehrh. fabricated ZnO nano falcates and its photocatalytic and dose dependent in vitro bio-activity
  15. Organic biocides hosted in layered double hydroxides: enhancing antimicrobial activity
  16. Experimental study on the regulation of the cholinergic pathway in renal macrophages by microRNA-132 to alleviate inflammatory response
  17. Synthesis, characterization, in-vitro antimicrobial properties, molecular docking and DFT studies of 3-{(E)-[(4,6-dimethylpyrimidin-2-yl)imino]methyl} naphthalen-2-ol and Heteroleptic Mn(II), Co(II), Ni(II) and Zn(II) complexes
  18. M-Polynomials and Topological Indices of Dominating David Derived Networks
  19. Human Health Risk Assessment of Trace Metals in Surface Water Due to Leachate from the Municipal Dumpsite by Pollution Index: A Case Study from Ndawuse River, Abuja, Nigeria
  20. Analysis of Bowel Diseases from Blood Serum by Autofluorescence and Atomic Force Microscopy Techniques
  21. Hydrographic parameters and distribution of dissolved Cu, Ni, Zn and nutrients near Jeddah desalination plant
  22. Relationships between diatoms and environmental variables in industrial water biotopes of Trzuskawica S.A. (Poland)
  23. Optimum Conversion of Major Ginsenoside Rb1 to Minor Ginsenoside Rg3(S) by Pulsed Electric Field-Assisted Acid Hydrolysis Treatment
  24. Antioxidant, Anti-microbial Properties and Chemical Composition of Cumin Essential Oils Extracted by Three Methods
  25. Regulatory mechanism of ulinastatin on autophagy of macrophages and renal tubular epithelial cells
  26. Investigation of the sustained-release mechanism of hydroxypropyl methyl cellulose skeleton type Acipimox tablets
  27. Bio-accumulation of Polycyclic Aromatic Hydrocarbons in the Grey Mangrove (Avicennia marina) along Arabian Gulf, Saudi Coast
  28. Dynamic Change of Secondary Metabolites and spectrum-effect relationship of Malus halliana Koehne flowers during blooming
  29. Lipids constituents from Gardenia aqualla Stapf & Hutch
  30. Effect of using microwaves for catalysts preparation on the catalytic acetalization of glycerol with furfural to obtain fuel additives
  31. Effect of Humic Acid on the Degradation of Methylene Blue by Peroxymonosulfate
  32. Serum containing drugs of Gua Lou Xie Bai decoction (GLXB-D) can inhibit TGF-β1-Induced Epithelial to Mesenchymal Transition (EMT) in A549 Cells
  33. Antiulcer Activity of Different Extracts of Anvillea garcinii and Isolation of Two New Secondary Metabolites
  34. Analysis of Metabolites in Cabernet Sauvignon and Shiraz Dry Red Wines from Shanxi by 1H NMR Spectroscopy Combined with Pattern Recognition Analysis
  35. Can water temperature impact litter decomposition under pollution of copper and zinc mixture
  36. Released from ZrO2/SiO2 coating resveratrol inhibits senescence and oxidative stress of human adipose-derived stem cells (ASC)
  37. Validated thin-layer chromatographic method for alternative and simultaneous determination of two anti-gout agents in their fixed dose combinations
  38. Fast removal of pollutants from vehicle emissions during cold-start stage
  39. Review Article
  40. Catalytic activities of heterogeneous catalysts obtained by copolymerization of metal-containing 2-(acetoacetoxy)ethyl methacrylate
  41. Antibiotic Residue in the Aquatic Environment: Status in Africa
  42. Regular Articles
  43. Mercury fractionation in gypsum using temperature desorption and mass spectrometric detection
  44. Phytosynthetic Ag doped ZnO nanoparticles: Semiconducting green remediators
  45. Epithelial–Mesenchymal Transition Induced by SMAD4 Activation in Invasive Growth Hormone-Secreting Adenomas
  46. Physicochemical properties of stabilized sewage sludge admixtures by modified steel slag
  47. In Vitro Cytotoxic and Antiproliferative Activity of Cydonia oblonga flower petals, leaf and fruit pellet ethanolic extracts. Docking simulation of the active flavonoids on anti-apoptotic protein Bcl-2
  48. Synthesis and Characterization of Pd exchanged MMT Clay for Mizoroki-Heck Reaction
  49. A new selective, and sensitive method for the determination of lixivaptan, a vasopressin 2 (V2)-receptor antagonist, in mouse plasma and its application in a pharmacokinetic study
  50. Anti-EGFL7 antibodies inhibit rat prolactinoma MMQ cells proliferation and PRL secretion
  51. Density functional theory calculations, vibration spectral analysis and molecular docking of the antimicrobial agent 6-(1,3-benzodioxol-5-ylmethyl)-5-ethyl-2-{[2-(morpholin-4-yl)ethyl] sulfanyl}pyrimidin-4(3H)-one
  52. Effect of Nano Zeolite on the Transformation of Cadmium Speciation and Its Uptake by Tobacco in Cadmium-contaminated Soil
  53. Effects and Mechanisms of Jinniu Capsule on Methamphetamine-Induced Conditioned Place Preference in Rats
  54. Calculating the Degree-based Topological Indices of Dendrimers
  55. Efficient optimization and mineralization of UV absorbers: A comparative investigation with Fenton and UV/H2O2
  56. Metabolites of Tryptophane and Phenylalanine as Markers of Small Bowel Ischemia-Reperfusion Injury
  57. Adsorption and determination of polycyclic aromatic hydrocarbons in water through the aggregation of graphene oxide
  58. The role of NR2C2 in the prolactinomas
  59. Chromium removal from industrial wastewater using Phyllostachys pubescens biomass loaded Cu-S nanospheres
  60. Hydrotalcite Anchored Ruthenium Catalyst for CO2 Hydrogenation Reaction
  61. Preparation of Calcium Fluoride using Phosphogypsum by Orthogonal Experiment
  62. The mechanism of antibacterial activity of corylifolinin against three clinical bacteria from Psoralen corylifolia L
  63. 2-formyl-3,6-bis(hydroxymethyl)phenyl benzoate in Electrochemical Dry Cell
  64. Electro-photocatalytic degradation of amoxicillin using calcium titanate
  65. Effect of Malus halliana Koehne Polysaccharides on Functional Constipation
  66. Structural Properties and Nonlinear Optical Responses of Halogenated Compounds: A DFT Investigation on Molecular Modelling
  67. DMFDMA catalyzed synthesis of 2-((Dimethylamino)methylene)-3,4-dihydro-9-arylacridin-1(2H)-ones and their derivatives: in-vitro antifungal, antibacterial and antioxidant evaluations
  68. Production of Methanol as a Fuel Energy from CO2 Present in Polluted Seawater - A Photocatalytic Outlook
  69. Study of different extraction methods on finger print and fatty acid of raw beef fat using fourier transform infrared and gas chromatography-mass spectrometry
  70. Determination of trace fluoroquinolones in water solutions and in medicinal preparations by conventional and synchronous fluorescence spectrometry
  71. Extraction and determination of flavonoids in Carthamus tinctorius
  72. Therapeutic Application of Zinc and Vanadium Complexes against Diabetes Mellitus a Coronary Disease: A review
  73. Study of calcined eggshell as potential catalyst for biodiesel formation using used cooking oil
  74. Manganese oxalates - structure-based Insights
  75. Topological Indices of H-Naphtalenic Nanosheet
  76. Long-Term Dissolution of Glass Fibers in Water Described by Dissolving Cylinder Zero-Order Kinetic Model: Mass Loss and Radius Reduction
  77. Topological study of the para-line graphs of certain pentacene via topological indices
  78. A brief insight into the prediction of water vapor transmissibility in highly impermeable hybrid nanocomposites based on bromobutyl/epichlorohydrin rubber blends
  79. Comparative sulfite assay by voltammetry using Pt electrodes, photometry and titrimetry: Application to cider, vinegar and sugar analysis
  80. MicroRNA delivery mediated by PEGylated polyethylenimine for prostate cancer therapy
  81. Reversible Fluorescent Turn-on Sensors for Fe3+ based on a Receptor Composed of Tri-oxygen Atoms of Amide Groups in Water
  82. Sonocatalytic degradation of methyl orange in aqueous solution using Fe-doped TiO2 nanoparticles under mechanical agitation
  83. Hydrotalcite Anchored Ruthenium Catalyst for CO2 Hydrogenation Reaction
  84. Production and Analysis of Recycled Ammonium Perrhenate from CMSX-4 superalloys
  85. Topical Issue on Agriculture
  86. New phosphorus biofertilizers from renewable raw materials in the aspect of cadmium and lead contents in soil and plants
  87. Survey of content of cadmium, calcium, chromium, copper, iron, lead, magnesium, manganese, mercury, sodium and zinc in chamomile and green tea leaves by electrothermal or flame atomizer atomic absorption spectrometry
  88. Biogas digestate – benefits and risks for soil fertility and crop quality – an evaluation of grain maize response
  89. A numerical analysis of heat transfer in a cross-current heat exchanger with controlled and newly designed air flows
  90. Freshwater green macroalgae as a biosorbent of Cr(III) ions
  91. The main influencing factors of soil mechanical characteristics of the gravity erosion environment in the dry-hot valley of Jinsha river
  92. Free amino acids in Viola tricolor in relation to different habitat conditions
  93. The influence of filler amount on selected properties of new experimental resin dental composite
  94. Effect of poultry wastewater irrigation on nitrogen, phosphorus and carbon contents in farmland soil
  95. Response of spring wheat to NPK and S fertilization. The content and uptake of macronutrients and the value of ionic ratios
  96. The Effect of Macroalgal Extracts and Near Infrared Radiation on Germination of Soybean Seedlings: Preliminary Research Results
  97. Content of Zn, Cd and Pb in purple moor-grass in soils heavily contaminated with heavy metals around a zinc and lead ore tailing landfill
  98. Topical Issue on Research for Natural Bioactive Products
  99. Synthesis of (±)-3,4-dimethoxybenzyl-4-methyloctanoate as a novel internal standard for capsinoid determination by HPLC-ESI-MS/MS(QTOF)
  100. Repellent activity of monoterpenoid esters with neurotransmitter amino acids against yellow fever mosquito, Aedes aegypti
  101. Effect of Flammulina velutipes (golden needle mushroom, eno-kitake) polysaccharides on constipation
  102. Bioassay-directed fractionation of a blood coagulation factor Xa inhibitor, betulinic acid from Lycopus lucidus
  103. Antifungal and repellent activities of the essential oils from three aromatic herbs from western Himalaya
  104. Chemical composition and microbiological evaluation of essential oil from Hyssopus officinalis L. with white and pink flowers
  105. Bioassay-guided isolation and identification of Aedes aegypti larvicidal and biting deterrent compounds from Veratrum lobelianum
  106. α-Terpineol, a natural monoterpene: A review of its biological properties
  107. Utility of essential oils for development of host-based lures for Xyleborus glabratus (Coleoptera: Curculionidae: Scolytinae), vector of laurel wilt
  108. Phenolic composition and antioxidant potential of different organs of Kazakh Crataegus almaatensis Pojark: A comparison with the European Crataegus oxyacantha L. flowers
  109. Isolation of eudesmane type sesquiterpene ketone from Prangos heyniae H.Duman & M.F.Watson essential oil and mosquitocidal activity of the essential oils
  110. Comparative analysis of the polyphenols profiles and the antioxidant and cytotoxicity properties of various blue honeysuckle varieties
  111. Special Issue on ICCESEN 2017
  112. Modelling world energy security data from multinomial distribution by generalized linear model under different cumulative link functions
  113. Pine Cone and Boron Compounds Effect as Reinforcement on Mechanical and Flammability Properties of Polyester Composites
  114. Artificial Neural Network Modelling for Prediction of SNR Effected by Probe Properties on Ultrasonic Inspection of Austenitic Stainless Steel Weldments
  115. Calculation and 3D analyses of ERR in the band crack front contained in a rectangular plate made of multilayered material
  116. Improvement of fuel properties of biodiesel with bioadditive ethyl levulinate
  117. Properties of AlSi9Cu3 metal matrix micro and nano composites produced via stir casting
  118. Investigation of Antibacterial Properties of Ag Doped TiO2 Nanofibers Prepared by Electrospinning Process
  119. Modeling of Total Phenolic contents in Various Tea samples by Experimental Design Methods
  120. Nickel doping effect on the structural and optical properties of indium sulfide thin films by SILAR
  121. The effect mechanism of Ginnalin A as a homeopathic agent on various cancer cell lines
  122. Excitation functions of proton induced reactions of some radioisotopes used in medicine
  123. Oxide ionic conductivity and microstructures of Pr and Sm co-doped CeO2-based systems
  124. Rapid Synthesis of Metallic Reinforced in Situ Intermetallic Composites in Ti-Al-Nb System via Resistive Sintering
  125. Oxidation Behavior of NiCr/YSZ Thermal Barrier Coatings (TBCs)
  126. Clustering Analysis of Normal Strength Concretes Produced with Different Aggregate Types
  127. Magnetic Nano-Sized Solid Acid Catalyst Bearing Sulfonic Acid Groups for Biodiesel Synthesis
  128. The biological activities of Arabis alpina L. subsp. brevifolia (DC.) Cullen against food pathogens
  129. Humidity properties of Schiff base polymers
  130. Free Vibration Analysis of Fiber Metal Laminated Straight Beam
  131. Comparative study of in vitro antioxidant, acetylcholinesterase and butyrylcholinesterase activity of alfalfa (Medicago sativa L.) collected during different growth stages
  132. Isothermal Oxidation Behavior of Gadolinium Zirconate (Gd2Zr2O7) Thermal Barrier Coatings (TBCs) produced by Electron Beam Physical Vapor Deposition (EB-PVD) technique
  133. Optimization of Adsorption Parameters for Ultra-Fine Calcite Using a Box-Behnken Experimental Design
  134. The Microstructural Investigation of Vermiculite-Infiltrated Electron Beam Physical Vapor Deposition Thermal Barrier Coatings
  135. Modelling Porosity Permeability of Ceramic Tiles using Fuzzy Taguchi Method
  136. Experimental and theoretical study of a novel naphthoquinone Schiff base
  137. Physicochemical properties of heat treated sille stone for ceramic industry
  138. Sand Dune Characterization for Preparing Metallurgical Grade Silicon
  139. Catalytic Applications of Large Pore Sulfonic Acid-Functionalized SBA-15 Mesoporous Silica for Esterification
  140. One-photon Absorption Characterizations, Dipole Polarizabilities and Second Hyperpolarizabilities of Chlorophyll a and Crocin
  141. The Optical and Crystallite Characterization of Bilayer TiO2 Films Coated on Different ITO layers
  142. Topical Issue on Bond Activation
  143. Metal-mediated reactions towards the synthesis of a novel deaminolysed bisurea, dicarbamolyamine
  144. The structure of ortho-(trifluoromethyl)phenol in comparison to its homologues – A combined experimental and theoretical study
  145. Heterogeneous catalysis with encapsulated haem and other synthetic porphyrins: Harnessing the power of porphyrins for oxidation reactions
  146. Recent Advances on Mechanistic Studies on C–H Activation Catalyzed by Base Metals
  147. Reactions of the organoplatinum complex [Pt(cod) (neoSi)Cl] (neoSi = trimethylsilylmethyl) with the non-coordinating anions SbF6– and BPh4
  148. Erratum
  149. Investigation on Two Compounds of O, O’-dithiophosphate Derivatives as Corrosion Inhibitors for Q235 Steel in Hydrochloric Acid Solution
Heruntergeladen am 29.11.2025 von https://www.degruyterbrill.com/document/doi/10.1515/chem-2018-0032/html
Button zum nach oben scrollen