Weather Conditions Influence on Hyssop Essential Oil Quality

This paper is a study of the chemical composition of Hyssopus officinalis ssp. officinalis grown during three years (2017–2019) at the Institute of Field and Vegetable Crops Novi Sad (Vojvodina Province, Serbia). Furthermore, comparisons with ISO standards during the years were also investigated, as well as a prediction model of retention indices of compounds from the essential oils. An essential oil obtained by hydrodistillation and analysed by GC-FID and GC-MS was isopinocamphone chemotype. The gathered information about the volatile compounds from H. officinalis was used to classify the samples using the unrooted cluster tree. The correlation analysis was applied to investigate the similarity of different samples, according to GC-MS data. The quantitative structure–retention relationship (QSRR) was also employed to predict the retention indices of the identified compounds. A total of 74 experimentally obtained retention indices were used to build a prediction model. The coefficient of determination for the training cycle was 0.910, indicating that this model could be used for the prediction of retention indices for H. officinalis essential oil compounds.

[1]  D. Adamović,et al.  Composition of Oils of Three Cultivated Forms of Hyssopus officinalis Endemic in Yugoslavia: f. albus Alef., f. cyaneus Alef. and f. ruber Mill. , 2001 .

[2]  L. Pezo,et al.  Factor space differentiation of brick clays according to mineral content: Prediction of final brick product quality , 2015 .

[3]  M. Mohammadhosseini.  Novel PSO-MLR Algorithm to Predict the Chromatographic Retention Behaviors of Natural Compounds , 2013 .

[4]  Alexander Tropsha,et al.  Best Practices for QSAR Model Development, Validation, and Exploitation , 2010, Molecular informatics.

[5]  R. Khavari-Nejad,et al.  Essential oil composition of Hyssop (Hyssopus officinalis L.) under salt stress at flowering stage , 2016 .

[6]  Jie Xu,et al.  Quantitative structure–property relationship study of β-cyclodextrin complexation free energies of organic compounds , 2015 .

[7]  S. Hamedeyazdan,et al.  Phytochemical analysis and antioxidant activity of Hyssopus officinalis L. from Iran. , 2011, Advanced pharmaceutical bulletin.

[8]  G. Zawiślak.  Hyssop herb yield and quality depending on harvest term and plant spacing. , 2011 .

[9]  M. Mohammadhosseini,et al.  QSAR study of VEGFR-2 inhibitors by using genetic algorithm-multiple linear regressions (GA-MLR) and genetic algorithm-support vector machine (GA-SVM): a comparative approach , 2015, Medicinal Chemistry Research.

[10]  E. Stahl-Biskup,et al.  Essential oils and glycosidic bound volatiles from leaves, stems, flowers and roots of Hyssopus officinalis L. (lamiaceae) , 1991 .

[11]  A. Zalacain,et al.  Effects of Agronomic Practices on Volatile Composition of Hyssopus officinalis L. Essential Oils , 2011, Molecules.

[12]  Roberto Todeschini,et al.  Handbook of Molecular Descriptors , 2002 .

[13]  W. Setzer,et al.  Composition and antimicrobial activity of the essential oil of Hyssopus seravschanicus growing wild in Tajikistan , 2012 .

[14]  F. Şahin,et al.  Essential oil composition of Hyssopus officinalis L. subsp. angustifolius (Bieb.) Arcangeli from Turkey , 2005 .

[15]  H. Kallio,et al.  Volatile components and odor intensity of four phenotypes of hyssop (Hyssopus officinalis L.) , 1994 .

[16]  P. Singh,et al.  Composition of the Volatiles of Hyssopus officinalis (L.) and Thymus serpyllum (L.) from Uttarakhand Himalaya , 2012 .

[17]  M. Nicoletti,et al.  A Pinocamphone Poor Oil of Hyssopus officinalis L. var. decumbens from France (Barton) , 1998 .

[18]  I. Atanassov,et al.  Genetic and flower volatile diversity in two natural populations of Hyssopus officinalis L. in Bulgaria , 2020 .

[19]  M. Curini,et al.  Composition and Antifungal Activity of Two Essential Oils of Hyssop (Hyssopus officinalis L.) , 2004 .

[20]  M. Novaković,et al.  Composition, antifungal and antioxidant properties of Hyssopus officinalis L. subsp. pilifer (Pant.) Murb. essential oil and deodorized extracts , 2013 .

[21]  Roman Kaliszan,et al.  QSRR: quantitative structure-(chromatographic) retention relationships. , 2007, Chemical reviews.

[22]  I. Stappen,et al.  Chemical composition and antifungal activity of essential oil of Hyssopus officinalis L. from Bulgaria against clinical isolates of Candida species , 2015 .

[23]  M. Ignjatov,et al.  Chemical composition of hyssop cv. 'Domaći ljubičasti' essential oil and its antimicrobial activity , 2021 .

[24]  Dong-Sheng Cao,et al.  ChemDes: an integrated web-based platform for molecular descriptor and fingerprint computation , 2015, Journal of Cheminformatics.

[25]  Tomislav Tosti,et al.  The chemical, biological and thermal characteristics and gastronomical perspectives of Laurus nobilis essential oil from different geographical origin , 2020 .

[26]  R. Sahraei,et al.  A green ultrasonic-assisted liquid-liquid microextraction based on deep eutectic solvent for the HPLC-UV determination of ferulic, caffeic and cinnamic acid from olive, almond, sesame and cinnamon oil. , 2016, Talanta.

[27]  Predrag S. Kojić,et al.  Predicting hydrodynamic parameters and volumetric gas–liquid mass transfer coefficient in an external-loop airlift reactor by support vector regression , 2017 .

[28]  Aurélien Thomas,et al.  Current approaches and challenges for the metabolite profiling of complex natural extracts. , 2015, Journal of chromatography. A.

[29]  W. Setzer,et al.  A new chemical form of essential oil of Hyssopus officinalis L. (Lamiaceae) from Nigeria , 2011 .

[30]  K. Başer,et al.  Composition of the essential oil of the Hyssopus officinalis L. subsp. angustifolius (Bieb.) Arcangeli , 2016 .

[31]  G. Mazzanti,et al.  Antibacterial and Cytotoxic Activity of Hyssopus officinalis L. Oils , 1999 .

[32]  S. Ketabchi,et al.  Essential Oil Composition and Antibacterial Activity of Hyssopus Officinalis L. Grown in Iran. , 2012 .

[33]  V. Mitić,et al.  Essential oil composition of Hyssopus officinalis L. cultivated in Serbia , 2000 .

[34]  CHUN WEI YAP,et al.  PaDEL‐descriptor: An open source software to calculate molecular descriptors and fingerprints , 2011, J. Comput. Chem..

[35]  K. Héberger.  Quantitative structure-(chromatographic) retention relationships. , 2007, Journal of chromatography. A.

[36]  K. Svoboda,et al.  Agronomical and phytochemical investigation of Hyssopus officinalis , 1993 .

[37]  Reza Aalizadeh,et al.  Quantitative Structure-Retention Relationship Models To Support Nontarget High-Resolution Mass Spectrometric Screening of Emerging Contaminants in Environmental Samples , 2016, J. Chem. Inf. Model..

[38]  Ezgi Demir,et al.  Automated and standard extraction of antioxidant phenolic compounds of Hyssopus officinalis L. ssp. angustifolius , 2013 .

[39]  C. Giuliani,et al.  Essential oil composition, polar compounds, glandular trichomes and biological activity of Hyssopus officinalis subsp. aristatus (Godr.) Nyman from central Italy , 2015 .

[40]  N. Arslan,et al.  Blooming stages of Turkish hyssop (Hyssopus officinalis L.) affect essential oil composition , 2008 .

[41]  Z. Abbas,et al.  Essential Oil Composition of Hyssopus officinalis L . Cultivated in Egypt , 2015 .

[42]  J. Chalchat,et al.  Essential Oil of Hyssopus officinalis L., Lamiaceae of Montenegro Origin , 1995 .

[43]  K. Msaada,et al.  Effect of salinity on the antiparasitic activity of hyssop essential oil , 2020, Journal of Essential Oil Research.

[44]  M. Witting,et al.  QSRR Modeling for Metabolite Standards Analyzed by Two Different Chromatographic Columns Using Multiple Linear Regression , 2017, Metabolites.

[45]  Guangji Wang,et al.  An integral strategy toward the rapid identification of analogous nontarget compounds from complex mixtures. , 2013, Journal of chromatography. A.

[46]  É. Németh-Zámbori,et al.  Effect of genotype and age on essential oil and total phenolics in hyssop ( Hyssopus officinalis L.) , 2017 .

[47]  Z. Aghajani,et al.  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 , 2016 .

[48]  R. Kowalski,et al.  Chemical composition and microbiological evaluation of essential oil from Hyssopus officinalis L. with white and pink flowers , 2018 .

[49]  M. Mahboubi,et al.  Antimicrobial Activity and Chemical Composition of Hyssopus officinalis L. Essential oil , 2011 .

[50]  M. Shokrpour,et al.  Effects of exogenous application of citrulline on prolonged water stress damages in hyssop (Hyssopus officinalis L.): Antioxidant activity, biochemical indices, and essential oils profile. , 2020, Food chemistry.

[51]  R. Croteau,et al.  Hydroxylation of (-)-β-Pinene and (-)-α-Pinene by a Cytochrome P-450 System from Hyssop (Hyssopus Officinalis) , 1992 .

[52]  Youngohc Yoon,et al.  A Comparison of Discriminant Analysis versus Artificial Neural Networks , 1993 .

[53]  Alexander Golbraikh,et al.  Predictive QSAR modeling workflow, model applicability domains, and virtual screening. , 2007, Current pharmaceutical design.

[54]  Y. Marrero-Ponce,et al.  QSRR prediction of gas chromatography retention indices of essential oil components , 2017, Chemical Papers.

[55]  L. Kotyuk.  Hyssop composition depending on age and plants development phases , 2015 .

[56]  H. Karataş,et al.  Chemical composition, antimicrobial and antioxidant activities of hyssop (Hyssopus officinalis L.) essential oil. , 2010 .