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Article

Yield and Composition of the Essential Oil of the Opopanax Genus in Turkey

by
Ebru Yüce Babacan
1,
Azize Demirpolat
2,
Uğur Çakılcıoğlu
1,* and
Eyüp Bagcı
3
1
Department of Botany, Pertek Sakine Genç Vocational School, Munzur University, 62000 Tunceli, Turkey
2
Vocational School of Food Agriculture and Livestock, Bingöl University, 12000 Bingöl, Turkey
3
Department of Biology, Faculty of Sciences, Fırat University, 23119 Elazığ, Turkey
*
Author to whom correspondence should be addressed.
Molecules 2023, 28(7), 3055; https://doi.org/10.3390/molecules28073055
Submission received: 25 February 2023 / Revised: 27 March 2023 / Accepted: 27 March 2023 / Published: 29 March 2023
(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)
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Abstract

:
The genus Opopanax W. Koch (Apiaceae) is represented by four species in Turkey. The composition of the essential oil of Opopanax genus members (Apiaceae) growing in Turkey was investigated in this study. GC-MS was used to analyze the composition of Opopanax essential oil samples that were taken from their natural environments. The Clevenger apparatus was used to hydrodistill the plant’s aerial parts, and the yields were determined to be between 0.2% v/w (for O. siifolius) and 0.4% (for O. hispidus, O. chironium, and O. persicus). The results and the chemical data provided some information and clues on the chemotaxonomy of the genus Opopanax. In this study, γ-elemene, butanoic acid octyl ester, and cylopropane were the main compounds identified in the essential oils of O. chironium, O. hispidus, and O. persicus. In particular, hexynyl n-valerate was most abundant in the essential oil of O. chironium, cyclopropane in that of O. hispidus, γ-elemene in that of O. persicus, and n-hexadecanoic acid/palmitic acid in that of O. siifolius. In a chemotaxonomic approach, the essential oil analysis of the Opopanax species revealed that these species conformed in a cluster analysis with their morphological classification. The constituents of the essential oils of all examined in the genus Opopanax were determined in this study, which is the most thorough one to date. This study provides new information about the composition of the essential oils of the investigated species.

1. Introduction

Apiaceae family members are significant plants that have economic importance all over the world. They are used as a vegetable food and as animal feed. Some Apiaceae species are also used as ornamental plants in parks and gardens. Because of the alkaloids and resins they contain, these plants are widely used in the medicine and cosmetics industries as well [1].
Opopanax is a genus within the Apiaceae family that is represented in Flora Iranica by O. persicus Boiss & Held and O. hispidus Griseb. The only species in Siberian flora is O. armeniacum Bordz., whereas Flora Europaea includes O. hispidus and O. chironium W.D.J. Koch [2,3]. The three species identified in Turkey are members of the genus Opopanax, which is spread in the Mediterranean region, Western Asia, and southern Europe. The uncommon monotypic Turkish genus Crenosciadium was recently classified as a synonym for Opopanax. The genus Opopanax is also represented by three species in Turkey [4]. As a result of recent studies, Crenosciadium Boiss. & Heldr. is a genus that has been combined with Opopanax and is represented by four species [5,6]. Bentham & Hooker [7] showed that Crenosciadium is closely related to Opopanax, while Menemen reported that C. siifolium (Boiss et. Heldr) [5] Menemen is a synonym for Opopanax siifolius (Boiss. & Heldr.); however, it differs from Opopanax in that it has a dorsal flat fruit. Özcan et al. studied the molecular characterizations of the nrDNA ITS, cpDNA matK, and trnL-F regions of C. siifolium and Opopanax species and determined that these two genera, although very similar, are different from each other [8]. The mericarp morphology is particularly helpful for separating the genera Opopanax and Crenosciadium, and the mericarp ribs are very significant for separating the two genera [9].
Members of the Opopanax genus have been used as medicine since antiquity and have also been consumed as a perfume for a long period in the past, for thousands of years. Humans may consume it in a variety of ways, such as by combining it with warm water or consuming it as resin [10]. Opopanax hispidus has a wider geographical distribution than other Opopanax members. This species is distributed from Western Europe to the Balkans and western parts of Asia. The stem and leaves of O. hispidus are used as antiseptics in Iranian ethnobotany, while the stem is used to treat infertility in Turkish folk medicine [11]. The root and aerial parts of O. chironium were extensively studied and found to contain various phthalides and C-17 acetylenes. In addition, it has been reported that this species has high antimicrobial and antioxidant activity against Escherichia coli and Listeria monocytogenes because of the phenols and flavonoids it contains [12]. Previous bioactivity and phytochemical studies showed that the genus Opopanax generally produces phenolics, diterpenes, coumarins, phthalides and has diverse biological properties. These compounds provide it with some pharmacological properties such as antioxidant, antimicrobial, and anticancer activities [12,13].
Studies have been conducted on the phytochemistry, conventional use, and pharmacological properties of the Opopanax genus. Additionally, data and chemical indicators that the species of this genus could be used therapeutically have been published. The genus Opopanax primarily produces phenolics, coumarins, phthalides, and diterpenes and possesses a variety of biological and pharmacological characteristics, including antioxidant, anticancer, and antibacterial activities, according to previous phytochemical and bioactivity investigations [14,15].
In phytochemistry and taxonomic studies, applications based on chemotaxonomy, especially predictions to determine the phytochemical content of plants, have gained great importance in recent years. Investigating the phytochemical components of Opopanax species naturally grown in Turkey was the goal of this study. We also aimed to determine the chemotaxonomic relationships between inter and infrageneric means. The results provide important clues on the taxonomic position of the genus members.

2. Results

There were quantitative and qualitative variations in the essential oils of the Opopanax species. In the essential oil composition of the Opopanax genus naturally grown in Turkey forty-one, thirty-two, twenty-three, and thirty components were identified in the essential oils of O. chironium, O. hispidus, O. siifolius, and O. persicus, respectively (Table 1). The identified compounds accounted for 86.9%, 90.8%, 96.4%, and 88.3% of the essential oils of O. chironium, O. hispidus, O. siifolius, and O. persicus species, respectively. The essential oil yields varied between 0.2 and 0.4 mL per 100 g of plant sample.
Hexyl n-valerate was also found to be highly present in O. chironium essential oil (18.5%). The presence of myristicin (16.5%), γ-elemene (16.0%), and butanoic acide-octyl ester (12.0%) was also important. In the oil of O. hispidus, cylopropane was the major compound (24.0%), followed by γ-elemene (14.0%), butanoic acid-octyl ester (11.5%), 1,3-benzodioxole (10.5%), and caryophyllene oxide (5.4%).
The results of the essential oils from the aerial part of O. siifolius analysis indicated n-hexadecanoic acid/palmitic acid (33.3%), stearic acid/n-octadecanoic acid (17.2%), oleic acid/(Z)-9-octadecenoic acid (12.0%) as the major components. The analysis of the essential oil O. persicus indicated that γ-elemene (20.5%), cylopropane (17.6%), and butanoic acide-octyl ester (13.5%) were the major components.

3. Discussion

The composition of the essential oil of Opopanax species in Turkey was compared with those reported in other studies and described in terms of constituents content. The essential oil of hydrodistilled O. chironium aerial parts was reported to contain cembrene (14.6%), angelicin (coumarins) (4.5%), β-caryophyllene (3.2%), E-β-Ionone (3.7%), (E)-β-damascenone (3.7%), and (E)-geranyl-acetone (3.3%) as main compounds (59). The only diterpenes detected in the extracts of O. chironium and O. persicum were coumarins. These species are also endemic to Iran, Turkey, Iraq, and Transcaucasia [57,58,59]. The presence of coumarins, such as columbianadin, eucedanin, diterpene, and gaudichaudin, called peucelinenoxide acetate, was determined in the extract obtained from O. chironium [13,60,61]. In the oil of O. chironium (L.) Koch, E-farnesyl acetate (20.2%) was determined as a major component [62]. In our study, trans-β-farnesene was found at a minor level (0.3%).
In the essential oil from the fruits of O. hispidus, 79 compounds were identified, and geranyl acetate (17.9%), tyrosol (48.8%), incensole acetate (4.3%), and germacrene D (4.0%) were the main components [63]. The content of geranyl acetate was 1.0% and that of germacrene D was 0.5% on the essential oil, and they appeared as minor components in this study. The content of γ-elemene was determined to be 20.5% in our study, and thus, it was found to be a significant chemical. γ-elemene from O. hispidus has shown strong insecticidal activity against the agricultural pest Spodoptera litura and may be beneficial as an environmentally benign biopesticide [64]. O. hispidus, used for the treatment of sclerosis, can also be used as a biopesticide [65]. The other major component of the essential oil from the Opopanax genus determined in this study was cyclopropane, found in the essential oils of O. chironium, O. hispidus, O. persicus in quantities corresponding to 5.5, 24.0, and 17.6%, respectively.
The oils of O. hispidus, O. chironium, and O. persicus were found to contain butanoic acide-octyl ester (content of 11.5%, 12.0%, and 13.5%, respectively. A fatty acid found naturally in plants is butanoic acid octyl ester. It can be found as a fatty acid and a glycol ether. Candida glabrata, a fungus that can infect the skin, has been demonstrated to be resistant to butanoic acid octyl ester. Butanoic acid octyl ester has been used as a dietary supplement to increase the absorption of lipophilic nutrients, such as vitamins A, D, E, and K. There are no documented side effects or toxicity for this substance [66].
In this study, the lowest amount of n hexadecanoic acid (33.3%) was found in the essential oil of O. siifolius. Due to the harmful side effects of synthetic compounds used for chemical protection, the use of substances obtained from plant sources, showing antimicrobial activity, is increasing. Palmitic acid, also known as n-hexadecanoic acid, is a type of saturated fatty acid [67]. It is well known that several fatty acids have antibacterial and antifungal effects [68]. By directly interacting with T cells, fatty acids can influence the immunological responses [69]. By reducing the generation of inflammatory mediators, dietary conjugated linoleic acid has an anti-inflammatory impact [70].
The essential oil analysis performed here showed that all Opopanax species are rich in sesquiterpenes and low in monoterpenes. Especially, O. siifolius contains more common saturated and unsaturated fatty acids. The results demonstrated the occurrence of major compounds in the genus patterns, i.e., the hexynyl n-valerate chemotype in O. chironium, the cyclopropane chemotype in O. hispidus, the γ-element chemotype in O. persicus, the palmitic acid chemotype in O. siifolius, in the eastern Anatolian region of Turkey. The chemical analysis results of O. siifolius showed that this species may be a different group and could be transferred to a genus different from Crenosciadium. As in our previous studies, the chemical analysis results supported the morphological data [71,72].
As shown in Table 1, the essential oil analysis conducted for this study indicated some chemical differences and similarities among the members of the Opopanax genus. The result of the clustering analysis was based on 10 main components in the essential oils of the Opopanax spp. examined, (Figure 1) and revealed that the Opopanax species were chemically as well as morphologically similar. The cluster analysis showed that O. siifolius belongs to the outermost clade according to the main essential oil compounds. Considering the groupings, it was observed that O. chironium, O. hispidus, O. persicus species were connected to each other (big group), and it is said that, chemically, they are closely related species. However, O. siifolius was far from these three species and appeared as a single species. It was concluded that the results are compatible with the morphological appearance of the taxa. The dendrogram showed that O. chironium and O. hispidus are closely related species, and O. persicus is connected with this small cluster and has a high similarity. O. siifolius was found in a different single cluster that combines with this triple cluster at a high level. This chemical grouping of the Opopanax genus members confirmed that O. siifolium may belong to a different genus, as indicated by the morphological analysis [5] and the molecular characterization of the Opopanax and Crenasciadum genera.
The results and the chemical data provided some information and clues on the chemotaxonomy of the genus Opopanax. In this study, γ-elemene, butanoic acid-octyl ester, cylopropane were the main components determined in O. chironium, O. hispidus, O. persicus whereas palmitic acid was the dominant component in O. siifolius. Hexynyl n-valerate (O. chironium), cyclopropane (O. hispidus), γ-elemene (O. persicus), and palmitic acid (O. siifolius) were the most abundant components in the essential oils of the analyzed taxa. Myristicin was detected only in O. chironium, and spatulenol was detected only in O. hispidus. Hexyl n-valerate, γ-elemene, butanoic acid-octyl ester and cyclopropane were among the major components in O. chironium, O. hispidus, and O. persicus oils. On the other hand, the major compounds detected in O. siifolius were different from those identified in the other Opopanax species studied (palmitic, stearic, oleic, linoleic acids and ethillinoleolate) (Table 1).
Based on previously published investigations, multivariate analysis was applied [29]. Both principal component analysis (PCA) and cluster analysis (CA) were used to determine the chemicals in the various samples. Then, using the matrix correlation setup, PCA was carried out using Varimax rotation. PC1 (50.96%) and PC2 (16.76%) were the two primary components of the principal component analysis, respectively. PC1 and PC2 carried a combined load of 67.72%. To investigate the correlation between the variables, the Kaiser–Meyer–Olkin (KMO) approach was used. The KMO value was 0.728, which is a respectable value. For the data set, Barlett’s test of sphericity likewise demonstrated a statistically significant difference at alpha of 0.04. The link between the four Opopanax species and their essential oil concentration was highlighted using PCA analysis, which was carried out using two different groups (PC1 and PC2). Figure 1, Figure 2 and Figure 3 show the results.
A biplot graph was created in this work to establish the multivariate relationships of the chemicals in the essential oils of the four Opopanax species investigated (Figure 3). If the angle between the vectors was less than 90°, the content of that species was better than the average; if the angle was larger than 90°, the content of that species was lower than the average; if the angle was equal to 90°, the content was near the average. Figure 3 shows the values of all components in the examined species and if they properties were positively or negatively associated with one another. The statistical analyses verified the results.
Essential oils have a wide range of beneficial properties. In this work, we isolated the essential oil from species of the Opopanax genus. It is possible to say that it is useful to compare the composition of essential oils and to provide basic data for taxonomic and essential oil evaluations in studies on plant genera. The study of essential oils is important to obtain chemotaxonomical relationships and promote scientific agriculture and product diversity. It is thought that the information on these essential oils will be useful for many industries working with natural products, such as the medical, cosmetics, landscaping, flavor, and food industries.

4. Materials and Methods

4.1. Sample Collection

The location information for the plant samples’ natural habitats is provided in Table 2. The plants were taken from their natural environment during the peak flowering season, which is from June to August, and were air-dried in the shade. The aerial parts of the species were used in the analyses. The Fırat University Herbarium is where the plant specimens are kept (FUH).

4.2. Isolation of Essential Oils and GC-MS Analysis

The plants used in this research were air-dried. The oil from the plants was extracted using the hydrodistillation technique. Using the Clevenger equipment, 3 h of hydrodistillation were performed on 100 g of air-dried aerial plant material. The organic layer in the gathering vial was transferred to the GC/GC-MS FID equipment once the distillation process was accomplished.
GC-MS was used to examine the essential oils [71,72]. The instrument was an HP 6890 model. The mass range was between 40 and 330 m/z, and the ionization energy was 70 eV. Opopanax samples (1 µL) were loaded into a GC (HP 5890 Series) for the analysis. The samples were run on a multi-purpose HP-5 column, 30 m, 0.25 mm, 0.25 µm (catalog number 19091J-313 Agilent, Santa Clara, CA, USA) [73,74].
Helium was used as the carrier gas, with a steady column flow rate of 1 mL/min. The settings for the column oven temperature program were 40 °C and a hold time of 2 min with a temperature rise of 3 °C/min rate until 240 °C (hold time, 2 min.). The flow rate was set to 1 l, and a 3.5 min buffer hold time was applied to the hexane samples. The split mode was chosen (split ratio 1:10 or 1:100). The detector temperature was 250 °C.
The mass spectrometric settings were full scan mode, 20,000 amu/s scan speed, and 50 spectra per sample frequency. The temperature at the contact injector and ion source was 250 °C and 200 °C, respectively.
Alkanes were used as standards to compare the retention indices (RI). By comparing the retention times (RT), mass spectra, and RI of the essential oils to those described in the literature (NIST 20 and Wiley Libraries) and MS libraries (Wiley MS library, New York, NY, USA) [75], the chemical components of the essential oils were identified. Traditional library searches just compare spectra rather than taking the retention parameters into account. In this study, libraries were searched using a combination of storage indexes, which made the compound identification simpler and more accurate. The device’s retention index spectrum libraries were also utilized in this study. The same analytical procedure as that for an identical column provided in the library was applied for better results. Table 1 details the essential oil constituents that were identified.

4.3. Cluster Analysis and PCA (Principal Component Analysis)

Ten significant components (less than 1%) were chosen from the water-distilled essential oil components. For the four Opopanax species, these elements were submitted to cluster analysis using numerical taxonomic techniques. The UPGMA statistical approach and the IBM SPSS Statistics 21.0.0 software were both employed for this investigation. Dendrograms were used to show the findings of these analyses, and the results were assessed in terms of numerical chemotaxonomic connections. The relationships between the species are shown in the cluster analysis tree shown in Figure 1.
To determine the variability’s organizational structure and calculate the distances between groups, multivariate analysis was used. Complete data sets were used for these analyses. To determine the commonalities between each measured unit, the UPGMA (unweighted pair-group average linkage) clustering approach based on Pearson distances was applied (Figure 2). The chemical components of the four Opopanax species’ essential oils served as the dependent variable. The chemicals of various samples were assessed using cluster analysis (CA) and principal component analysis (PCA). The unstandardized statistics were assigned the same weight as that previously reported.
The promax rotation was then used to perform the PCA with the matrix correlation configuration. PCA was then performed in the XLSTAT 2022 software using the matrix type correlation configuration. The species’ proximity and distance from one another based on their essential oils’ content are discussed. “R” (Boston, MA, USA) was used to create biplot graphs (Figure 3).

Author Contributions

Conceptualization, E.Y.B. and A.D.; methodology, E.B.; software, A.D.; validation, E.B.; formal analysis, E.Y.B.; investigation, A.D.; resources, U.Ç.; data curation, E.B.; writing—original draft preparation, A.D.; writing—review and editing, A.D. and U.Ç.; supervision, A.D.; project administration, E.Y.B.; funding acquisition, E.Y.B. All authors have read and agreed to the published version of the manuscript.

Funding

This research received no external funding.

Institutional Review Board Statement

Not applicable.

Informed Consent Statement

Not applicable.

Data Availability Statement

Not applicable.

Conflicts of Interest

The authors declare no conflict of interest.

References

  1. Güner, A.; Aslan, S.; Ekim, T.; Vural, M.; Babaç, M.T. (Eds.) Türkiye Bitkileri Listesi (Damarlı Bitkiler); Nezahat Gökyigit Botanik Bahçesi ve Flora Araştırma Dernegi Yayını: Istanbul, Turkey, 2012. [Google Scholar]
  2. Shishkin, B.K. Opopanax, Flora of the U.S.S.R. Volume 17 (Umbelliflorae); Botanical Institute of the Academy of Sciences of the USSR: Moscow, Russia, 1973. [Google Scholar]
  3. Tutin, T.G. Opopanax L. In Flora Europaea; Tutin, T.G., Heywood, V.H., Burges, N.A., Moore, D.M., Valentine, D.H., Walters, S.M., Webb, D.A., Eds.; Cambridge University Press: Cambridge, UK, 1968; Volume 2, p. 360. [Google Scholar]
  4. Chamberlain, D.F. Opopanax Koch. In Flora of Turkey and the East Aegean Island; Davis, P.H., Ed.; Edinburgh University Press: Edinburgh, UK, 1972; Volume 4, pp. 471–473. [Google Scholar]
  5. Menemen, Y. Opopanax. In Türkiye Bitkileri Listesi (Damarlı Bitkiler); Güner, A., Aslan, S., Ekim, T., Vural, M., Babaç, M.T., Eds.; Nezahat Gökyigit Botanik Bahçesi ve Flora Arastirma Dernegi Yayini: Istanbul, Turkey, 2012; pp. 70–71. [Google Scholar]
  6. Davis, P.H. Flora of Turkey and the East Aegean Islands; Edinburgh University Press: Edinburgh, UK, 1972; p. 12. [Google Scholar]
  7. Bentham, G. Umbelliferae. In Genera Plantarum; Bentham, G., Hooker, J.D., Eds.; Taylor and Francis, Ltd.: London, UK, 1867; Volume 1, pp. 859–893. [Google Scholar]
  8. Özcan, T.; Çetin, Ö.; Çelik, M.; Albayrak, F. Defining phylogenetic relationship between the genera Opopanax and Crenosciadium using nuclear and chloroplast DNA sequence data. BAUN Fen. Bil. Enst. Dergisi 2021, 23, 716–731. [Google Scholar] [CrossRef]
  9. Cetin, O.; Çelik, M. Comparative morphological, anatomical, micromorphological, and palynological studies on the genera Opopanax and Crenosciadium (Apiaceae). Phytotaxa 2018, 372, 35–50. [Google Scholar] [CrossRef]
  10. Rahmani, A.H.; Anwar, S.; Raut, R.; Almatroudi, A.; Babiker, A.Y.; Khan, A.A.; Alsahli, M.A.; Almatroodi, S.A. Therapeutic potential of myrrh, a natural resin, in health management through modulation of oxidative stress, inflammation, and advanced glycation end products formation using in vitro and in silico analysis. Appl. Sci. 2022, 12, 9175. [Google Scholar] [CrossRef]
  11. Amiri, M.S.; Joharchi, M.R. Ethnobotanical knowledge of Apiaceae family in Iran: A review. Avicenna J. Phytomed 2016, 6, 621–635. [Google Scholar] [PubMed]
  12. Gumusok, S.; Yilmaz Sarialtin, S.; Çoban, T.; Kiliç, C. A Preliminary Study On The Antioxidant And Anti- Inflammatory Activities of Opopanax hispidus. J. Ankara Univ. Fac. Pharm. 2021, 45, 577–585. [Google Scholar]
  13. Önder, A.; Nahar, L.; Nath, S.; Sarker, S.D. Phytochemistry, Traditional uses and pharmacological properties of the genus Opopanax W.D.J. Koch: A Mini-Review. Pharm. Sci. 2020, 26, 99–106. [Google Scholar] [CrossRef]
  14. Moradi, H.; Ghavam, M.; Tavili, A. Study of antioxidant activity and some herbal compounds of Dracocephalum kotschyi Boiss. in different ages of growth. Biotech. Rep. 2020, 25, 408. [Google Scholar] [CrossRef]
  15. Balogun, O.S.; Olukayode, R.; Solomon, A.; Adeleke, A.J. Hexahydrofarnesyl acetone-rich extractives from Hildegardia barteri. J. Herbs Spices Med. Plants 2017, 23, 393–400. [Google Scholar] [CrossRef]
  16. Carrapiso, A.I.; Jurado, A.; Timon, M.L.; Garcia, C. Odor-active compounds of Iberian hams with different aroma characteristics. J. Agric. Food Chem. 2002, 50, 6453–6458. [Google Scholar] [CrossRef]
  17. Karagül-Yüceer, Y.; Cadwallader, K.R.; Drake, M.A. Volatile flavor components of stored nonfat dry milk. J. Agric. Food Chem. 2002, 50, 305–312. [Google Scholar] [CrossRef]
  18. Ramos, M.F.S.; Siani, A.C.; Tappin, M.R.R.; Guimaraes, A.C.; Lahoz, J.E.; Ribeiro, J.E.L.S. Essential oils from oleoresins of Protium spp. of the Amazon region. Flavour Fragr. J. 2000, 15, 383–387. [Google Scholar] [CrossRef]
  19. Yu, Y.; Huang, T.; Yang, B.; Liu, X.; Duan, G. Development of gas chromatography-mass spectrometry with microwave distillation and simultaneous solid-phase microextraction for rapid determination of volatile constituents in gingeri. J. Pharm. Biomed. Anal. 2007, 43, 24–31. [Google Scholar] [CrossRef]
  20. Rychlik, M.; Schieberle, P.; Grosch, W. Compilation of odour thresholds, odour qualities and retention indices of key food odorants. Dt. Forschungsanst. Techn. Uni. 1998, 1, 63. [Google Scholar]
  21. Brander, C.F.; Kepner, R.E.; Webb, A.D. Identification of some volatile compounds of wine of Vitis vinifera cultivar pinot noir. Am. J. Enol. Vitic. 1980, 31, 69–75. [Google Scholar] [CrossRef]
  22. Kılıç, Ö. Essential oils composition of two endemic, Umbelliferae herbs growing wild in Turkey. J. Agric. Sci. Technol. 2014, 4, 435–442. [Google Scholar]
  23. Chastrette, M.; Heintz, M.; Druilhe, A.; Lefort, D. Analyse chromatographique d’esters aliphatiques saturés. Relations rétention-structure et prévision de la rétention. Bull. Soc. Chim. Fr. 1974, 9, 1852–1856. [Google Scholar]
  24. Malliaa, S.; Fernandez-Garcia, E.; Bosset, J.O. Comparison of purge and trap and solid phase microextraction techniques for studying the volatile aroma compounds of three European PDO hard cheeses. Int. Dairy J. 2005, 15, 741–758. [Google Scholar] [CrossRef]
  25. Alencar, J.W.; Alves, B.P.; Craveiro, A.A. Pyrolysis of tropical vegetable oils. J. Agric. Food Chem. 1983, 31, 1268–1270. [Google Scholar] [CrossRef]
  26. Ayoub, I.M.; Abdel-Aziz, M.M.; Elhady, S.S.; Bagalagel, A.A.; Malatani, R.T.; Elkady, W.M. Valori-zation of Pimenta racemosa essential oils and extracts: GC-MS and LC-MS Phytochemical profiling and evaluation of Helicobacter pylori inhibitory activity. Molecules 2022, 27, 7965. [Google Scholar] [CrossRef]
  27. Peng, C.T.; Yang, Z.C.; Ding, S.F. Prediction of retention idexes. II. Structure-retention index relationship on polar columns. J. Chromatogr. 1991, 586, 85–112. [Google Scholar] [CrossRef]
  28. Janzanntti, N.S.; Franco, M.R.B.; Lanças, F.M. Identificação de compostos voláteis de maçãs (Malus domestica) cultivar fuji, por cromatografia gasosa-espectrometria de massas. Cienc. Tecnol. Aliment. 2000, 20, 164–171. [Google Scholar] [CrossRef]
  29. Chretien, J.R.; Dubois, J.-E. Topological Analysis: A technique for the physico-chemical exploitation of retention data in gas-liquid chromatography. J. Chromatogr. 1978, 158, 43–56. [Google Scholar] [CrossRef]
  30. Avsar, Y.K.; Karagul-Yuceer, Y.; Drake, M.A.; Singh, T.K.; Yoon, Y.; Cadwallader, K.R. Characterization of nutty flavor in cheddar cheese. J. Dairy Sci. 2004, 87, 1999–2010. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  31. Hively, R.A.; Hinton, R.E. Variation of the retention index with temperature on squalane substrates. J. Gas Chromatogr. 1968, 6, 203–217. [Google Scholar] [CrossRef]
  32. Takeoka, G.R.; Buttery, R.G.; Flath, R.A. Volatile constituents of Asian pear (Pyrus serotina). J. Agric. Food Chem. 1992, 40, 1925–1929. [Google Scholar] [CrossRef]
  33. Frizzo, C.D.; Serafini, L.A.; Dellacassa, E.; Lorenzo, D.; Moyna, P. Essential oil of Baccharis uncinella DC. from Southern Brazil. Flavour Fragr. J. 2001, 16, 286–288. [Google Scholar] [CrossRef]
  34. Engewald, W.; Epsch, K.; Welsch, T.; Graefe, J. Molekülstruktur und Retentionsverhalten. VI. Retentionsverhalten von bicycle[n.m.0]alkanen bei der gas-adsorptions- und gas-verteilungs-chromatographie. J. Chromatogr. 1976, 119, 119–128. [Google Scholar] [CrossRef]
  35. Komárek, K.; Hornová, L.; Horna, A.; Churácek, J. Glass capillary gas chromatography of homologous series of esters. III. Separation of alkyl halogenopropionates and halogenobutyrates on OV-101. J. Chromatogr. 1983, 262, 316–320. [Google Scholar] [CrossRef]
  36. Melkani, A.B.; Dev, V.; Beauchamp, P.S.; Negi, A.; Mehta, S.P.S.; Melkani, K.B. Constituents of the essential oil of a new chemotype of Elsholtzia strobilifera Benth. Biochem. Syst. Ecol. 2005, 33, 419–425. [Google Scholar] [CrossRef]
  37. Spencer, M.D.; Pangborn, R.M.; Jennings, W.G. Gas chromatographic and sensory analysis of volatiles from cling peaches. J. Agric. Food Chem. 1978, 26, 725–732. [Google Scholar] [CrossRef]
  38. Hazzit, M.; Baaliouamer, A.; Faleiro, M.L.; Miguel, M.G. Composition of the essential oils of Thymus and Origanum species from Algeria and their antioxidant and antimicrobial activities. J. Agric. Food Chem. 2006, 54, 6314–6321. [Google Scholar] [CrossRef]
  39. Baharum, S.N.; Bunawan, H.; Ghani, M.A.; Mustapha, W.A.W. Analysis of the chemical composition of the essential oil of Polygonum minus Huds. using two-dimensional gas chromatography-time-of-flight mass spectrometry (GC-TOF-MS). Molecules 2010, 15, 7006–7015. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  40. Chevance, F.F.V.; Farmer, L.J. Identification of major volatile odor compounds in frankfurters. J. Agric. Food Chem. 1999, 47, 5151–5160. [Google Scholar] [CrossRef] [PubMed]
  41. Vujisic, L.; Vuckovic, I.; Tesevic, V.; Dokovic, D.; Ristic, M.S.; Janackovic, P.; Milosavljevic, S. Comparative examination of the essential oils of Anthemis ruthenica and A. arvensis wild-growing in Serbia. Flavour Fragr. J. 2006, 21, 458–461. [Google Scholar] [CrossRef]
  42. Kurashov, E.A.; Mitrukova, G.G.; Krylova, Y.V. Variations in the component composition of essential oil of Ceratophyllum demersum (Ceratophyllaceae) during vegetation (in press). Plant Resour. 2014, 1. [Google Scholar]
  43. Mastelic, J.; Jerkovic, I.; Mesic, M. Volatile constituents from flowers, leaves, bark and wood of Prunus mahaleb L. Flavour Fragr. J. 2006, 21, 306–313. [Google Scholar] [CrossRef]
  44. Demirpolat, A.; Bagci, E.; Dogan, G. Essential oil composition of Scandix iberica Bieb. and Scandix stellata Banks and Sol (Apiaceae) from different parts, a chemotaxonomic approach. Glob. J. Bot. Sci. 2011, 5, 55–62. [Google Scholar] [CrossRef]
  45. Escalona-Arranz, J.C.; Perez-Roses, R.; Jimenez, I.L.; Rodriguez-Amado, J.; Argota-Coello, H.; Canizares-Lay, J.; Morris-Quevedo, H.J.; Sierra-Gonzales, G. Chemical constituents of Tamarindus indica L. leaves. Rev. Cubana Quim. 2010, 22, 65–71. [Google Scholar]
  46. Stojanovic, G.; Palic, R.; Alagic, S.; Zekovic, Z. Chemical composition and antimicrobial activity of the essential oil and CO2 extracts of semi-oriental tobacco, Otlja. Flavour Fragr. J. 2000, 15, 335–338. [Google Scholar] [CrossRef]
  47. Finkelstein, E.E.; Kurbatova, S.V.; Kolosova, E.A. Study of biological activity of structure analogies of adamantane. Proc. Samara State Univ. 2002, 26, 121–128. [Google Scholar]
  48. Bruce, T.J.; Cork, A.C.; Hall, D.R.; Dunkelblum, E. Laboratory and field evaluation of floral odours from African marigold, Tagetes erecta, and sweet pea, Lathyrus odoratus, as kairomones for the cotton bollworm Helicoverpa armigera. OBC Wprs Bull. 2002, 25, 315–322. [Google Scholar]
  49. Sillam-Dussès, D.; Sémon, E.; Moreau, C.; Valterová, I.; Sobotník, J.; Robert, A.; Bordereau, C. Neocembrene A, a major component of the trail-following pheromone in the genus Prorhinotermes (Insecta, Isoptera, Rhinotermitidae). Chemoecology 2005, 15, 1–6. [Google Scholar] [CrossRef]
  50. Schmidt, J.M.; Noletto, J.A.; Vogler, B.; Setzer, W.N. Abaco Bush Medicine: Chemical composition of the essential oils of four aromatic medicinal plants from Abaco Island, Bahamas, J. Herbs. Spices Med. Plants 2006, 12, 43–65. [Google Scholar] [CrossRef]
  51. Demirpolat, A. Chemical Composition of Essential Oils of Seven Polygonum Species from Turkey: A Chemotaxonomic Approach. Molecules 2022, 27, 9053. [Google Scholar] [CrossRef]
  52. Pino, J.A.; Mesa, J.; Munoz, Y.; Marti, M.P.; Marbot, R. Volatile components from mango (Mangifera indica L.) cultivars. J. Agric. Food Chem. 2005, 53, 2213–2223. [Google Scholar] [CrossRef] [PubMed]
  53. Sun, Q.-L.; Hua, S.; Ye, J.-H.; Zheng, X.-Q.; Liang, Y.R. Flavonoids and volatiles in Chrysanthemum morifolium Ramat flower from Tongxiang County in China. Afr. J. Biotechnol. 2010, 9, 3817–3821. [Google Scholar]
  54. Dogan, G.; Bagci, E. Essential oil composition of Papaver rhoeas L. corn poppy Papaveraceae from Turkey. Hacet. J. Biol. Chem. 2014, 42, 545–549. [Google Scholar]
  55. Gauvin, A.; Lecomte, H.; Smadja, J. Comparative investigations of the essential oils of two scented geranium (Pelargonium spp.) cultivars grown on Reunion Island. Flavour Fragr. J. 2004, 19, 455–460. [Google Scholar] [CrossRef]
  56. Andriamaharavo, N.R. Retention Data; NIST Mass Spectrometry Data Center: Gaithersburg, MD, USA, 2014. [Google Scholar]
  57. Appendino, G.; Bianchi, F.A.; Bader, C.; Campagnuolo, E.; Fattorusso, O.; Taglialatela-Scafati, M.; Blanco-Molina, A.; Macho, B.L.; Fiebich, P.; Heinrich, M.; et al. Coumarins from Opopanax chironium. New dihydrofuranocoumarins and differential induction of apoptosis by imperatorin and heraclenin. J. Nat. Prod. 2004, 67, 532–536. [Google Scholar] [CrossRef]
  58. Rajabi, A.; Ebrahimi, S.; Neuburger, M.T.; Wagner, S.; Zimmermann, M.; Quitschau, G.; Amin, M. Phytochemical profiling of Opopanax persicus Boiss. Planta Med. 2011, 77, WS14. [Google Scholar] [CrossRef]
  59. Maggioa, A.; Brunoa, M.; Formisanob, C.; Riganob, D.; Senatoreb, F. Chemical Composition of the Essential Oils of Three Species of Apiaceae Growing Wild in Sicily: Bonannia graeca, Eryngium maritimum and Opopanax chironium. Nat. Prod. Commun. 2013, 8, 6. [Google Scholar] [CrossRef] [Green Version]
  60. Vieira, I.J.C.; Mathias, L.; Monteiro, V.; Braz-Filho, R.; Rodrigues-Filho, E. A New Coumarin from Brosimum gaudichaudii Trecul. Nat. Prod. Lett. 1999, 13, 47–52. [Google Scholar] [CrossRef]
  61. Muckensturm, B.; Boulanger, A.; Ouahabi, S.; Reduron, J.P. A new irregular diterpenoid from Opopanax chironium. Fitoterapia 2005, 6, 768–770. [Google Scholar] [CrossRef] [PubMed]
  62. Evergetis, E.; Haroutounian, S.A. The Umbelliferae (Apiaceae) of Dioscorides annotated in codex neapolitanus graecus. J. Ethnopharmacol. 2015, 175, 549. [Google Scholar] [CrossRef] [PubMed]
  63. Matejic, J.S.; Ristic, M.S.; Randelovic, V.N.; Marin, P.D.; Dzamic, A.M. Chemical composition of the essential oil of Opopanax hispidus. Chem. Nat. Compd. 2018, 54, 1174–1176. [Google Scholar] [CrossRef]
  64. Duke, J. Dr. Duke’s Phytochemical and Ethnobotanical Databases; United States Department of Agriculture, Agricultural Research Service: Washington, DC, USA, 2004.
  65. Hartwell, J.L. Plants used against cancer. A survey. Lloydia 1971, 34, 103–160. [Google Scholar]
  66. Byosynth. Available online: https://www.biosynth.com/p/AAA11039/110-39-4-butanoic-acid-octyl-ester/ (accessed on 28 March 2023).
  67. Eastwood, M. Principles of Human Nutrition; Blackwell Publishing Company: New York, NY, USA, 2003. [Google Scholar]
  68. Agoramoorthy, M.; Chandrasekaran, V.; Venkatesalu, M.J.H. Antibacterial and antifungal activities of fatty acid methyl esters of the blind-your-eye mangrove from India. Braz. J. Microbiol. 2007, 38, 739–742. [Google Scholar] [CrossRef] [Green Version]
  69. Lawrence, J.L.; Eric, G.B.; Robert, B.Z. Treatment of rheumatoid arthritis with gamma linolenic acid. Ann. Intern. Med. 1993, 119, 9. [Google Scholar]
  70. Yu, Y.; Correll, P.H.; Heuvel, J.P.V. Conjugated linoleic acid decreases production of pro-inflammatory products in macrophages: Evidence for a PPAR gamma dependent mechanism. Biochim. Biophys. Acta 2002, 1581, 89–99. [Google Scholar] [CrossRef]
  71. Bagci, E.; Yuce, E. Constituents of the Essential Oils of Two Hypericum capitatum Choisy Varieties (var. capitatum and var. luteum Robson) from Turkey. J. Essent. Oil Bear. Plants 2011, 14, 106–113. [Google Scholar] [CrossRef]
  72. Bagci, E.; Yuce, E. The essential oils of the aerial parts of two Hypericum (H. pseudolaeve Robson and H. thymbrifolium Boiss. & Noe) species from East Anatolian Region of Turkey. J. Essent. Oil Bear. Plants 2013, 13, 390–397. [Google Scholar]
  73. Kumar, A.; Lindley, M.R.; Mastana, S.S. A time efficient adaptation of GC-FID method for the analysis of PBMC lipid composition. J. Biochem. Technol. 2014, 5, 760–764. [Google Scholar]
  74. Rezaei, F.; Jamei, R.; Heidari, R. Evaluation of volatile profile, fatty acids composition and in vitro bioactivity of Tagetes minuta growing wild in Northern Iran. Adv. Pharm. Bull. 2018, 8, 115. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  75. Adams, R.P. Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry; Allured Publishing Corporation: Carol Stream, IL, USA, 2007; Volume 456. [Google Scholar]
Molecules 28 03055 g001 550
Figure 1. Clustering analysis of the Opopanax genus according to oil volatile components.
Figure 1. Clustering analysis of the Opopanax genus according to oil volatile components.
Molecules 28 03055 g001
Molecules 28 03055 g002 550
Figure 2. The composition of the essential oils of Opoponax species was analyzed using principal component analysis (PCA).
Figure 2. The composition of the essential oils of Opoponax species was analyzed using principal component analysis (PCA).
Molecules 28 03055 g002
Molecules 28 03055 g003 550
Figure 3. Biplot (PCA) of the composition of the essential oils of the examined Opopanax species.
Figure 3. Biplot (PCA) of the composition of the essential oils of the examined Opopanax species.
Molecules 28 03055 g003
Table
Table 1. Components of the essential oils from species of the Opopanax genus.
Table 1. Components of the essential oils from species of the Opopanax genus.
No.ComponentsRIRI(lit)Identification
Method		% Concentration
O.
chironium		O.
hispidus		O.
siifolius		O.
persicus
1.Octanal10741023 [16]RI, MS0.7---
2.Isovaleric acid1076872 [17]RI, MS0.1---
3.ο-Cymene10901026 [18]RI, MS0.2-0.1-
4.β-Ocimene10991040 [19]RI, MS0.80.2-0.5
5.Cyclohexane11191027 [20]RI, MS0.3---
6.1-Octanol11271093 [21]RI, MS2.00.5-1.2
7.Butanoic acid11461140 [22]RI, MS0.20.2-0.4
8.n-Amyl-Isovalerate11531125 [23]RI, MS0.50.2-0.3
9.Propanoic acid11801511 [24]RI, MS0.1--1.4
10.Etenilcyclohexane1216825 [25]RI, MS0.13.0--
11.Decanal12201204 [26]RI, MS-0.2-0.1
12.Cyclopropane1224405 [27]RI, MS5.524.0-17.6
13.Hexyl-2-hetylbutanoat12401240 [28]RI, MS-0.5--
14.Hexyl n-Valerate12461247 [29]RI, MS18.50.5-9.5
15.Pentanoic acid12491720 [30]RI, MS1.0---
16.Cis-cyclodecane12581227 [27]RI, MS0.2---
17.Cyclobutane1270455 [31]RI, MS0.2---
18.Acetic acid, decyl ester13031394 [32]RI, MS0.1---
19.n-Octyl İso Butyrate13321372 [32]RI, MS0.50.3-0.6
20.Eugenol13391359 [26]RI, MS0.1---
21.Thujene13581033 [33]RI, MS1.51.5-1.7
22.Bicyclo [4.1.0] heptane1367796 [34]RI, MS1.32.3-2.0
23.Butanoic acid-octyl ester13701372 [35]RI, MS12.011.5-13.5
24.α-Bourbonene13791385 [36]RI, MS0.5---
25.1-Decene13841061 [37]RI, MS1.51.5-1.8
26.Geranyl acetate13871392 [38]RI, MS-1.0-0.2
27.β-Caryophyllene13911392 [22]RI, MS-0.8--
28.Geranyl formate14041400 [22]RI, MS--0.5-
29.trans-β-farnesene14141477 [39]RI, MS0.30.2-0.3
30.cis-α-Bbsabolene14171417 [22]RI, MS0.2---
31.Naphthalene14291429 [22]RI, MS-0.3--
32.Germacrene D14341432 [22]RI, MS0.70.5-0.8
33.β-Gurjunene14421475 [19]RI, MS0.2 -0.5
34.γ-Elemene 14471437 [22]RI, MS16.014.00.920.5
35.1,3-Benzodioxole14581531 [27]RI, MS0.510.50.95.7
36.β-Sesquiphellandrene14601526 [19]RI, MS-1.1--
37.Myristicin14631522 [40]RI, MS16.5---
38.Germacrene B14831482 [22]RI, MS1.20.7-1.2
39.Spatulenol14931495 [22]RI, MS-3.1--
40.Caryophyllene oxide14971497 [22]RI, MS0.51.50.41.8
41.Isospathulenol15251638 [41]RI, MS0.10.5-0.3
42.α-Cadinene15381511 [38]RI, MS1.51.7-1.5
43.Isoaromadendrene epoxide15481594 [41]RI, MS-0.31.00.1
44.σ-Damascone15541456 [42]RI, MS0.3---
45.Farnesol 16251742 [43]RI, MS -3.3-
46.2 -Pentadecanone16291448 [44]RI, MS0.12.51.50.5
47.1,2-Benzenedicarboxylic acid16371643 [45]RI, MS--0.5-
48.Pentacosane16521561 [44]RI, MS--0.9
49.n-Hexadecanoic acid/Palmitic acid16901970 [46]RI, MS0.52.733.31.8
50.Adamantane17121400 [47]RI, MS--1.2-
51.Benzeneacetaldehyde17411640 [48]RI, MS0.1---
52.Cembrene A17471955 [49]RI, MS--3.80.6
53.Methoxsalen17492020 [50]RI, MS0.1
54.2-Hexadecen-1-ol17911420 [51]RI, MS-2.11.5
55.Linoleic acid18052078 [43]RI, MS0.1 5.10.5
56.Oleic acid/(Z)-9-Octadecenoic acid18092141 [52]RI, MS--12.0-
57.Etillinoleolat1812-RI, MS--3.9-
58.3-Cyclohexane-1-methanol18211071 [53]RI, MS--1.7-
59.Stearic acid/n-Octadeca noic acid18262180 [41]RI, MS--17.21.0
60.Cyclooctanone1896-RI, MS--2.0-
61.Tricosane19001902 [54]RI, MS0.10.2--
62.Cis-Sesquicyclo-geraniol19041865 [55]RI, MS--1.9-
63.Trimethylene1918-RI, MS--1.6-
64.Eicosanoic acid19292365 [56]RI, MS--0.80.1
TOTAL 86.990.896.488.3
Table
Table 2. Collection date and locality information for the studied Opopanax species.
Table 2. Collection date and locality information for the studied Opopanax species.
1O. chironiumTekirdağ between Hayrabolu, 10 km from Tekirdağ, wet places along the river, 70 m., 13 June 2015, Paksoy * 2018 N 40.951741, E 27.468926
2O. hispidusMuğla, Turgutreis Aspat region, Aspat castle and around, within the scrubs, 100–150 m, 2 July 2015, Paksoy 2021 N 37.000135, E 27.267143
3O. persicusVan, Near the Hoşap, wet grassy places, 2000 m, 20 June 2016, Paksoy 2049 N 38.317180, E 43.802793
4O. siifoliusAntalya, Akçay, Around the Girdev lake, near the river, 2000 m, 3 August 2015, Paksoy 2024 N 36.664530, E 29.659819
* The samples were collected by Mehmet Yavuz Paksoy.
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Babacan, E.Y.; Demirpolat, A.; Çakılcıoğlu, U.; Bagcı, E. Yield and Composition of the Essential Oil of the Opopanax Genus in Turkey. Molecules 2023, 28, 3055. https://doi.org/10.3390/molecules28073055

AMA Style

Babacan EY, Demirpolat A, Çakılcıoğlu U, Bagcı E. Yield and Composition of the Essential Oil of the Opopanax Genus in Turkey. Molecules. 2023; 28(7):3055. https://doi.org/10.3390/molecules28073055

Chicago/Turabian Style

Babacan, Ebru Yüce, Azize Demirpolat, Uğur Çakılcıoğlu, and Eyüp Bagcı. 2023. "Yield and Composition of the Essential Oil of the Opopanax Genus in Turkey" Molecules 28, no. 7: 3055. https://doi.org/10.3390/molecules28073055

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