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Article

Composition of Essential Oils from Fruits of Peucedanum longifolium and Rhizomatophora aegopodioides (Apiaceae) with Regard to Other Related Taxa—A Chemometric Approach

by
Ljuboš Ušjak
1,*,
Marjan Niketić
2,3 and
Silvana Petrović
1
1
Department of Pharmacognosy, University of Belgrade—Faculty of Pharmacy, Vojvode Stepe 450, 11221 Belgrade, Serbia
2
Biological Department, Natural History Museum, Njegoševa 51, 11000 Belgrade, Serbia
3
Department of Chemical and Biological Sciences, Serbian Academy of Sciences and Arts, Kneza Mihaila 35, 11000 Belgrade, Serbia
*
Author to whom correspondence should be addressed.
Separations 2024, 11(1), 14; https://doi.org/10.3390/separations11010014
Submission received: 29 November 2023 / Revised: 28 December 2023 / Accepted: 29 December 2023 / Published: 30 December 2023
(This article belongs to the Special Issue Applications of Separation and Purification Techniques for Natural Products Derived from Plants Source)
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Abstract

:
The aim of this work was to investigate the composition of essential oils isolated from fruits of Peucedanum longifolium, and Rhizomatophora aegopodioides (a species which was previously placed in the genus Peucedanum), as well as to compare the obtained results to those available for other previously investigated related species (including taxa which are also, according to some authors, excluded from the genus Peucedanum). Essential oils were obtained via hydrodistillation in a Clevenger-type apparatus and their composition was analyzed using GC-FID and GC-MS. To compare these data to those of previously investigated taxa, a chemometric approach was applied; the data were analyzed using multivariate statistical methods: non-metric multidimensional scaling (nMDS) and hierarchical cluster analysis. The most abundant in P. longifolium essential oil were monoterpenes (79.7%), mostly α-phellandrene (26.2%), β-phellandrene + limonene (21.0%) and myrcene (9.5%), followed by sesquiterpenes (18.3%), mostly germacrene B (9.5%). On the other hand, dominant in R. aegopodioides essential oil were non-terpenic aliphatic hydrocarbons (46.1%), mainly n-undecane (16.5%) and n-nonane (11.3%). In addition, this essential oil also contained a notable quantity of sesquiterpenes (25.1%), with (E)-sesquilavandulol being the most abundant (10.0%). The results of multivariate statistics revealed a clear separation of the essential oil composition of R. aegopodioides and P. longifolium, as well as of P. longifolium and P. officinale. The clustering of the samples of most of the taxa that do not belong to the Peucedanum in the narrow sense (sensu stricto) was also observed, which is in accordance with their recent inclusion in separate genera.

Graphical Abstract

1. Introduction

The genus Peucedanum L. (Apiaceae, Selineae), in the broadest sense (sensu amplo), is taxonomically a very polymorphic and polyphyletic group with 2–3-pinnate leaves and dorsally compressed fruits, and historically 859 specific and intraspecific plant names are attributed to it [1], of which about 100–120 (200) species have been recognized [2,3]. Based on phylogenetic [4], and other studies [5], North American and African genera, as well as Dichoropetalum Fenzl and some Eurasian genera, have been excluded from it nowadays; so, there is a consensus that in a broad sense (sensu lato), this genus includes 74 species distributed in Eurasia and North Africa [6,7]. Phylogenetically, they form a common clade with the type species of the genus, P. officinale L. [4,8]. However, some authors claim that this group actually consists of eight independent genera that differ considerably in the morphology of the vegetative parts, chemistry, etc. [1,4,5,8,9,10,11]. Some of them are mono- or oligotypic and the genus Peucedanum in a narrow sense (sensu stricto) consists of only 12 Eurasian species, and 38 species need to be distributed into other genera [1]. More recently, it has been proven on the basis of molecular analyses [11] that the separation of the monotypic genus Rhizomatophora Pimenov from Peucedanum sensu lato is justified [7,9].
Many Peucedanum taxa, both in a broad sense (sensu lato) and in a narrow sense (sensu stricto), were the subject of previous phytochemical studies. The majority of these studies concerned essential oils and coumarins [12]. Essential oils were rich in monoterpenes, such as those of P. officinale rhizomes, stems, leaves, flowers and fruits [13,14], or in sesquiterpenes, for example, those of P. tauricum M. Bieb. flowers and fruits [15]. Also, in some instances, the essential oils of Peucedanum taxa contained similar amounts of both of these types of terpenes, such as the one of P. verticillare (L.) W.D.J. Koch ex DC. fruits [16]. Regarding coumarins, mainly simple coumarins, furanocoumarins and their dihydro derivatives, as well as dihydropyranocoumarins were identified in different extracts originating from these species. Among other secondary metabolites, flavonoids, phenolic acids, chromones and phenylethanoids were revealed in the polar extracts of these taxa [12].
In this paper, the composition of the essential oils isolated from the fruits of Peucedanum longifolium Waldst. & Kit., as well as Rhizomatophora aegopodioides (Boiss.) Pimenov [=P. aegopodioides (Boiss.) Vandas], was analyzed. Like other species of Peucedanum sensu stricto, P. longifolium has xeromorphic leaves and linear leaf lobes with entire margins, and inhabits rocky places in Southeast Europe and Southwest Asia. In contrast, R. aegopodioides has mesomorphic leaves with ovate to oblong and toothed leaf lobes, and inhabits moist riparian habitats in Southern Italy, Southeast Europe and Southwest Asia [1,7,17].
Previously, essential oils of various aerial parts and organs of P. longifolium, but not of fruits, from Serbia, Montenegro and Turkey were investigated. Also, the root essential oil of the plant collected in Serbia was analyzed [18,19,20,21,22,23]. Furthermore, for the aerial parts’ essential oils (exact plant parts were not defined) from Turkey and Serbia, antioxidant and antibacterial activities, respectively, were demonstrated [18,19]. Also, furanocoumarins peucedanin, oxypeucedanin, oxypeucedanin hydrate and isoimperatorin, and simple coumarin osthole were isolated from the dry ethanol extracts of the roots and fruits of this plant [24].
Rhizomatophora aegopodioides’ essential oil composition was not the subject of former studies. For the dry methanol, ethyl acetate, water and/or acetone extracts of the aerial parts of this plant (investigated under the name Peucedanum aegopodioides), antioxidant (in DPPH and ABTS tests), antibacterial and antifungal activities were demonstrated [25].
The aim of this work was to investigate the composition of the essential oils isolated from the fruits of P. longifolium and R. aegopodioides, as well as to compare these results using multivariate statistics to those available for other previously investigated related species, including taxa which are also, according to some authors, excluded from the genus Peucedanum.

2. Materials and Methods

2.1. Plant Material

Umbels with ripe fruits of 20 individual plants were collected: in the case of P. longifolium from a population on Vis hill in Sićevo Gorge (43.324110° N, 22.087002° E, SE Serbia) on 22 October 2022; and in the case of R. aegopodioides from a population in the vicinity of Pirot, near village Basara (43.157361° N, 22.680775° E, SE Serbia) on 6 September 2022. The plants were identified by Dr. Marjan Niketić, curator/botanist of the Natural History Museum, Belgrade (Serbia). The voucher specimens are deposited in the Herbarium of the Natural History Museum, Belgrade (BEO), under the numbers 4398/01 and 4566/01, respectively. For isolation of essential oils, ripe fruits removed from umbels after drying were used.

2.2. Isolation of Essential Oils

Dried and powdered ripe fruits were hydrodistilled for 2.5 h using a Clevenger-type apparatus, according to a procedure given in European Pharmacopoeia 11.0 [26]; collecting solvent: n-hexane. Essential oils were dried over anhydrous sodium sulfate, n-hexane was evaporated, and the oils were stored at 4 °C until analysis. In the case of both species, essential oils were isolated from 90 g of fruits (three hydrodistillations of 30 g of fruits). The content of essential oils was expressed as the mean ± standard deviation: 0.91 ± 0.008%, w/w (P. longifolium); and 0.02 ± 0.004%, w/w (R. aegopodioides).

2.3. GC-FID and GC-MS Analysis

The composition of the essential oils was analyzed on an Agilent 6890N Gas Chromatograph (Agilent Technologies, Palo Alto, CA, USA), equipped with a split/splitless injector, a capillary column (Agilent HP-5MS 30 m × 0.25 mm, 0.25 μm film thickness) and a flame ionization detector (FID), and coupled to an Agilent 5975C MS detector (GC-FID-MS). Injector temperature: 200 °C. FID temperature: 300 °C. Carrier gas: helium. Carrier gas flow: 1.0 mL/min. The oven temperature program: 60 to 280 °C at 3 °C/min (linear); final temperature held for 10 min. Split ratio: 1:10. Essential oils were dissolved in n-hexane (1.5%, v/v). Injected volume: 1 μL. MSD operated in EI mode at 70 eV. MSD transfer line temperature: 250 °C. MSD ion source temperature: 230 °C. MSD analyzer (single quadrupole) temperature: 150 °C. Range m/z: 35–550. Scan speed: 2.83 scans/sec. The analysis was carried out using the MSD ChemStation E.01.00.237 software. Linear retention indices (RIs) of the essential oils’ components were calculated using the retention times obtained for the homologue series of n-alkanes (C8–C40) (Fluka, Buchs, Switzerland), which were ran under the same GC conditions. The identification of the compounds was based on the comparison of their RIs and mass spectra to those from the NIST/NBS 05, Wiley libraries 8th edition, and the literature [27]. The relative percentages of the essential oils’ components were calculated from the peak areas, which were recorded using FID.

2.4. Statistical Analysis

To compare the chemical composition of the essential oils isolated from the fruits of P. longifolium and R. aegopodioides, as well as of 12 previously investigated related taxa (23 essential oil samples), multivariate statistical methods, non-metric multidimensional scaling (nMDS) and unweighted pair group arithmetic averages clustering (UPGMA) were applied. nMDS was performed to graphically delineate dissimilarities and grouping among taxa, and UPGMA was used for the agglomerative hierarchical cluster analysis. The analyses were based on the Bray–Curtis pairwise distance matrix and included the essential oils’ components that were present in the relative quantities ≥ 1%. In total, 25 samples and 83 variables were assembled. To reduce the large differences between the data (relative percentages), they were coded in the following way [28]: value 1 for 0%, value 2 for quantities ≥ 1% and <2%, value 3 for quantities ≥ 2% and <5%, value 4 for quantities ≥ 5% and <10%, value 5 for quantities ≥ 10% and <20%, value 6 for quantities ≥ 20% and <40%, value 7 for quantities ≥ 40% and <60%, value 8 for quantities ≥ 60% and <80%, and value 9 for quantities ≥ 80%. The analysis was performed using software Statistica 6.0 (Statsoft Inc., Tulsa, OK, USA).

3. Results and Discussion

3.1. Chemical Composition of Peucedanum longifolium and Rhizomatophora aegopodioides Fruit Essential Oils

GC-FID and GC-MS analysis of the essential oils obtained from the fruits of P. longifolium and R. aegopodioides (Table 1) revealed the presence of 46 and 48 components, comprising 98.0 and 90.0% of the total essential oils, respectively.
The P. longifolium fruit essential oil was dominated by monoterpene hydrocarbons (74.4%). The most abundant was α-phellandrene (26.2%), and it was followed by β-phellandrene and limonene (21.0%), which eluted together under applied GC conditions. It should be noted that the co-elution of these two compounds was also observed in several other studies on the essential oils of the fruits of the Peucedanum taxa [29,30,31]. Other monoterpene hydrocarbons present in the investigated P. longifolium fruit essential oil in notable amounts were myrcene (9.5%), p-cymene (7.9%) and sabinene (4.1%). Among sesquiterpene hydrocarbons, which also constituted a prominent portion of this essential oil (17.9%), germacrene B was the only one present in a noteworthy amount (9.5%). All other compounds were detected in quantities below 2.5%.
Essential oils of some other plant parts and organs of P. longifolium were investigated previously. Five of six of these studies investigated essential oils isolated from the aerial parts of this plant. The essential oil of leaves and young stems collected in eastern Serbia (Mt. Tupižnica) was dominated by sesquiterpene β-elemene (24.7%), followed by monoterpene (E)-β-ocimene (11.7%) [20]. A similar composition was observed for the essential oils isolated from the leaves, collected in two phenophases (vegetative and flowering), also in eastern Serbia (Mt. Stara Planina), i.e., β-elemene (44.1 and 22.5%) and (E)-β-ocimene (8.5 and 26.7%) were also the most abundant. On the other hand, the flower essential oil of the plant collected on the same locality was rich in monoterpenes myrcene (23.1%), α-phellandrene (22.5%) and β-phellandrene (16.4%) [21]. Similarly, these three compounds were among the dominant in the fruit essential oil analyzed in our study. However, in the fruit essential oil, α- and β-phellandrene were more abundant than myrcene. In the three remaining studies, the aerial parts were not precisely defined. The essential oil of those collected in eastern Serbia (Mt. Rtanj) was dominated by myrcene (15.9%) and α-phellandrene (11.3%) [19]. The amount of myrcene could indicate that these aerial parts included flowers, but studies on more samples of flowers and fruits are necessary to prove this hypothesis. The essential oil of the aerial parts from Montenegro was also dominated by monoterpenes; however, the most abundant was α-pinene (36.3%) [22], while in the essential oil of the aerial parts from Turkey, the dominant was a sesquiterpene 8-cedren-13-ol (33.7%) [18]. Besides the aerial parts essential oils, in one study, the essential oil of the roots (collected on Mt. Stara Planina in eastern Serbia) was investigated. α-Pinene (60.3%) and sabinene (20.9%) were dominant [23].
In contrast to the P. longifolium fruit essential oil, the most abundant in the R. aegopodioides fruit essential oil were non-terpenic aliphatic hydrocarbons (46.1%), mainly n-undecane (16.5%) and n-nonane (11.3%). This essential oil also contained significant amounts of both non-oxygenated and oxygenated sesquiterpenes (11.4 and 13.6%), with (E)-sesquilavandulol being the most prominent (10.0%). A notable quantity of hexadecanoic acid (9.6%) was also present in R. aegopodioides’ fruit essential oil. Other compounds were detected in amounts below 5.0%.

3.2. Composition of Peucedanum longifolium and Rhizomatophora aegopodioides Fruit Essential Oils with Regard to Related Taxa

To compare the chemical composition of the essential oils obtained from the fruits of P. longifolium and R. aegopodioides, as well as of other related taxa, a chemometric approach was applied. The search for previous studies was performed using Google Scholar on 15.11.2023 using input text “Peucedanum” and “essential oil” and “fruit”. Also, the search was repeated, but using “seed” instead of “fruit”, because some authors incorrectly refer to fruits of the Apiaceae species as seeds. Moreover, a similar query was performed for the genera which are, according to some authors, excluded from Peucedanum, i.e., for Rhizomatophora, Xanthoselinum, Pteroselinum, Cervaria, Dichoropetalum, Oreoselinum, Thysselinum, Leutea, Tommasinia, Agasyllis, Pinacantha, Macroselinum, Paraligusticum, Karatavia, Imperatoria, Dystaenia, Leiotulus, Steganotaenia, Scandia, Annesorhiza, Lomatium, Ducrosia, etc. In these instances, the data on the fruit essential oil composition were found only in the last six genera. However, in this paper, we limited ourselves only to representatives of the Selineae tribe [10] that grow in Europe, with the exception of the Asian genus Leutea (Scandiceae tribe), which was taken as an outgroup. The results of 14 appropriate previous studies (Table 2) were included in multivariate statistical analysis. In total, together with the results of our investigation, 25 fruit essential oil samples obtained from 14 taxa, containing 83 compounds in a quantity above 1%, were included in the analysis. The accepted names of the analyzed taxa (including P. longifolium and R. aegopodioides), according to some authors, are given in Table 2. Of the 14 names, ten belong to Peucedanum in the broad sense (sensu lato), including five from Peucedanum in the narrow sense (sensu stricto). The dominant constituents of the fruit essential oils of these plants are also included in Table 2.
In the statistical analysis (Figure 1 and Figure 2), a clear distinction of R. aegopodioides’ fruit essential oil (aeg sample), dominated by non-terpenic aliphatic hydrocarbons, from that of other analyzed taxa, in which various terpenes were the main fruit essential oils’ components, was demonstrated.
Furthermore, the grouping of the essential oil samples of most of the other taxa (except the ver sample) that also do not belong to the Peucedanum in the narrow sense (sensu stricto) was observed. These essential oils were rich in monoterpene hydrocarbons. In most cases, α-pinene was amongst the dominant constituents (up to as much as 72.8%). Namely, α-pinene (10.7–40.2%), β-phellandrene (12.3–31.5%) and sabinene (15.7–33.9%) were the most abundant in P. alsaticum (now belonging to the genus Xanthoselinum) oil samples, α-pinene (31.3 and 22.3%), sabinene (31.0 and 22.0%) and β-pinene (21.7 and 33.1%) in P. cervaria (now belonging to the genus Cervaria) oil samples, α-pinene (72.8%) and β-pinene (20.4%) in P. chryseum (now belonging to the genus Dichoropetalum) oil sample, and α-pinene (47.3%) and sabinene (45.9%) in P. petiolare (now belonging to the genus Leutea) oil samples [29,30,31,33,38]. In addition, the P. chryseum and P. petiolare fruit essential oils generally had a small number of compounds (i.e., four) in a quantity above 1%, all of which were monoterpenes [33,38]. Further, the P. oreoselinum (now belonging to the genus Oreoselinum) and P. palustre (now belonging to the genus Thysselinum) fruit essential oil samples were also dominated by monoterpenes; however, the dominant one was limonene (17.9–87.5%) [35,36,37]. Regarding amounts of sesquiterpenes in all these essential oil samples, they were notably lower (below 9.0%) [29,30,31,33,35,36,37,38]. Somewhat different were the fruit essential oils of P. austriacum (now belonging to the genus Pteroselinum) and particularly P. verticillare (now belonging to the genus Tommasinia). These two, besides monoterpenes β-phellandrene (45.2%) and α-phellandrene (20.8%), respectively, also contained notable amounts of sesquiterpenes, such as germacrene D (6.4%) and (E)-caryophyllene (24.2%), respectively [16,32].
Within Peucedanum sensu stricto, the P. longifolium and P. officinale fruit essential oils (lon and off samples, respectively) were well separated, which does not support the opinion of some authors that P. longifolium is a subspecies of P. officinale. While the P. longifolium fruit essential oil sample was dominated by monoterpene hydrocarbons, in the P. officinale fruit essential oil sample, oxygenated monoterpene fenchone was the most abundant (32.0%) [14]. Our study represents a good basis for further research in this regard on more P. longifolium and P. officinale essential oil samples. Another oxygenated monoterpene trans-piperitol (51.2%) was the dominant in the fruit essential oil sample of P. dhana [34], which is also a member of Peucedanum sensu stricto. The remaining Peucedanum sensu stricto fruit essential oil samples investigated were dominated by sesquiterpenes: the P. ruthenicum essential oil was dominated by caryophyllene oxide (13.6%) and 8,9-dehydroisolongifolene (11.3%) [39], and the P. tauricum essential oil was dominated by guaia-9,11-diene (28.6%) and guaia-1(10),11-diene (26.1%) [15]. The P. longifolium fruit essential oil also contained a prominent amount of sesquiterpenes, mainly germacrene B.
It seems that small amounts of terpenic compounds in the fruit essential oil, as was the case in the Rhizomatophora sample, support the exclusion of such taxa from the Peucedanum genus. More studies are necessary to test the hypothesis that ratios of monoterpenes and sesquiterpenes, as well as of oxygenated and non-oxygenated terpenes, could also have the same role.

4. Conclusions

In this work, the composition of the essential oils obtained from the fruits of Peucedanum longifolium, as well as Rhizomatophora aegopodioides (which was previously a member of the genus Peucedanum), was investigated.
A multivariate statistical analysis of these results and appropriate literature data for the fruit essential oils of other related taxa was performed. An applied chemometric approach revealed the clustering of the samples of most of the taxa that do not belong to the Peucedanum in the narrow sense (sensu stricto), which is in agreement with their recent inclusion in separate genera. In this regard, significant differences were also revealed between the essential oils of R. aegopodioides and other taxa, including P. longifolium. The chemical composition of the essential oils analyzed also suggested the independent status of P. longifolium in relation to P. officinale.

Author Contributions

Conceptualization, S.P., M.N. and L.U.; methodology, L.U., S.P. and M.N.; investigation, L.U. and M.N.; resources, S.P. and M.N.; writing—original draft preparation, L.U. and M.N.; writing—review and editing, S.P.; visualization, L.U. and M.N.; supervision, S.P.; project administration, S.P.; funding acquisition, S.P. and M.N. All authors have read and agreed to the published version of the manuscript.

Funding

This research was funded by the Ministry of Science, Technological Development and Innovation of the Republic of Serbia, grant number 451-03-47/2023-01/200161.

Data Availability Statement

Data are contained within the article.

Conflicts of Interest

The authors declare no conflicts of interest.

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Separations 11 00014 g001
Figure 1. nMDS analysis of the composition of the fruit essential oils. Peucedanum sensu lato taxa are represented with circles with red outline and those that represent Peucedanum sensu stricto taxa are completely colored in red. Taxa that do not belong to Peucedanum sensu lato are represented with squares with blue outline. Acronyms are given in Table 2. Acronyms of samples investigated in the current work (lon and aeg) are outlined. Analysis was performed using coded values of relative % of the compounds: value 1—not detected, value 2—quantities ≥ 1% and <2%, value 3—quantities ≥ 2% and <5%, value 4—quantities ≥ 5% and <10%, value 5—quantities ≥ 10% and <20%, value 6—quantities ≥ 20% and <40%, value 7—quantities ≥ 40% and <60%, value 8—quantities ≥ 60% and <80%, value 9—quantities ≥80%.
Figure 1. nMDS analysis of the composition of the fruit essential oils. Peucedanum sensu lato taxa are represented with circles with red outline and those that represent Peucedanum sensu stricto taxa are completely colored in red. Taxa that do not belong to Peucedanum sensu lato are represented with squares with blue outline. Acronyms are given in Table 2. Acronyms of samples investigated in the current work (lon and aeg) are outlined. Analysis was performed using coded values of relative % of the compounds: value 1—not detected, value 2—quantities ≥ 1% and <2%, value 3—quantities ≥ 2% and <5%, value 4—quantities ≥ 5% and <10%, value 5—quantities ≥ 10% and <20%, value 6—quantities ≥ 20% and <40%, value 7—quantities ≥ 40% and <60%, value 8—quantities ≥ 60% and <80%, value 9—quantities ≥80%.
Separations 11 00014 g001
Separations 11 00014 g002
Figure 2. UPGMA cluster analysis of the composition of the fruit essential oils. Peucedanum sensu lato taxa are marked with red color and other taxa with blue color. Acronyms are given in Table 2. Acronyms of samples investigated in the current work (lon and aeg) are outlined. Coded values of relative % of the compounds used for analysis are given in Figure 1 caption.
Figure 2. UPGMA cluster analysis of the composition of the fruit essential oils. Peucedanum sensu lato taxa are marked with red color and other taxa with blue color. Acronyms are given in Table 2. Acronyms of samples investigated in the current work (lon and aeg) are outlined. Coded values of relative % of the compounds used for analysis are given in Figure 1 caption.
Separations 11 00014 g002
Table 1. Chemical composition of essential oils of Peucedanum longifolium (PL) and Rhizomatophora aegopodioides (RA) fruits.
Table 1. Chemical composition of essential oils of Peucedanum longifolium (PL) and Rhizomatophora aegopodioides (RA) fruits.
RIexp 1RIlit 2Compound 3PL (% 4)RA (% 4)
900900n-Nonane−11.3
911−Nonene isomer−0.3
926924α-Thujene0.5−
934932α-Pinene1.7−
949946Camphene0.3−
974969Sabinene4.1−
978974β-Pinene2.3−
9909842-Pentyl furan−0.3
991988Myrcene9.5−
10081002α-Phellandrene26.2−
10121008δ-3-Carene0.1−
10171014α-Terpinene0.1−
10261020p-Cymene7.9−
10311024/1025Limonene + β-Phellandrene21.0−
10361032(Z)-β-Ocimene0.1−
10461044(E)-β-Ocimene0.6−
10581054γ-Terpinene0.2−
10671065cis-Sabinene hydrate (IPP vs. OH)0.1−
10731067cis-Linalool oxide (furanoid)2.1tr
10891084trans-Linalool oxide (furanoid)1.3−
1089−Undecene isomer−1.0
1092−Undecene isomer−4.5
109310906,7-Epoxymyrcene0.1−
11001095Linalool0.1−
11001100n-Undecane−16.5
1104−Undecene isomer−0.9
1113−Undecene isomer−3.3
11221119trans-p-Mentha-2,8-dien-1-ol0.1-
11581144(2Z)-Nonen-1-al−0.3
11781174Terpinen-4-ol0.2tr
11871183Cryptone0.3−
1203−Phellandrene epoxide isomer0.8−
12051201n-Decanal−0.2
1238−Phellandrene epoxide isomer0.1−
12711266n-Decanol−0.3
1284−Tridecene isomer−1.0
1291−Tridecene isomer−1.2
12981300n-Tridecane−0.4
13021298Carvacrole0.2−
13751374α-Copaene0.1tr
13851387β-Bourbonene0.2-
139013881-Tetradecene−0.4
13921389β-Elemene0.6-
14071408Dodecanaltr0.4
141414112-epi-β-Funebrene−1.2
14201417(E)-Caryophyllene0.8−
14341434γ-Elemene0.5−
14431440β-Barbatene−1.5
144414426,9-Guaiadiene0.1−
14521453Geranyl acetone−0.4
14541452α-Humulene0.8−
14561454(E)-β-Farnesenetr1.7
14771478γ-Muurolenetr0.6
14821484Germacrene D1.21.2
14871489β-Selinene1.4−
14961498/1500α-Selinene + Bicyclogermacrene0.6−
14981500Pentadecane−0.5
15081502trans-β-Guaiene1.8−
15091500/1505Cuparene + β-Bisabolene−3.9
15241522δ-Cadinene0.10.8
15311533trans-Cadina-1,4-diene−0.5
15601559Germacrene B9.5−
15691565Dodecanoic acid−1.3
15781577Spathulenoltr0.3
15841582Caryophyllene oxide0.2−
16021582Neryl isovalerate−0.6
16101608Humulene epoxide II0.2−
16331631(E)-Sesquilavandulol−10.0
1680−Heptadecene isomer−1.0
16841685α-Bisabolol−1.3
1691−Heptadecene isomer−0.6
17211714(2E,6Z)-Farnesol−0.6
1766−Tetradecanoic acid−1.7
1844−Hexahydrofarnesyl acetone−1.4
1864−Pentadecanoic acid−0.5
19751959Hexadecanoic acid−9.6
2138−Octadecadienoic acid isomer−1.2
2144−Octadecadienoic acid isomer−1.2
2147−Octadecenoic acid isomer−1.0
22962300n-Tricosane−0.5
24972500n-Pentacosane−1.9
26962700n-Heptacosane−0.9
Monoterpene hydrocarbons74.4−
Oxygenated monoterpenes5.41.1
Sesquiterpene hydrocarbons17.911.4
Oxygenated sesquiterpenes0.413.6
Other aliphatic hydrocarbons−46.1
Other oxygenated aliphatic hydrocarbonstr1.4
Fatty acids−16.4
Total identified compounds98.090.0
Number of identified compounds4648
1 RIexp, retention indices on HP-5MS column relative to C8-C40 n-alkanes. 2 RIlit, retention indices obtained from the literature [27]. 3 Constituents listed in the order of elution on HP-5MS column. 4 Relative area percentage of the compounds obtained from FID area percent data; tr, trace (<0.1%); −, not detected.
Table 2. Accepted names of the analyzed taxa according to Plants of the World Online (POWO) [7], and Catalogue of Life (COL) [1], as well as the most abundant constituents (≥5%) of their fruit essential oils.
Table 2. Accepted names of the analyzed taxa according to Plants of the World Online (POWO) [7], and Catalogue of Life (COL) [1], as well as the most abundant constituents (≥5%) of their fruit essential oils.
Name Reported in Cited Article [Acronym]Accepted Name in POWOAccepted Name in COLThe Most Abundant Constituents in the Fruit Essential Oils (%)Reference
Peucedanum alsaticum L. [als1] 1As in cited articleXanthoselinum alsaticum (L.) Schur subsp. alsaticumSabinene (22.0), α-pinene (20.7), limonene + β-phellandrene (18.7), germacrene D (7.9), bornyl acetate (5.6), (E)-caryophyllene (5.5)Skalicka-Woźniak et al. [29]
Peucedanum alsaticum L.
[als2-4] 1		 α-Pinene (10.7–40.2), β-phellandrene (12.3–31.5), sabinene (15.7–33.9), γ-terpinene (2.4–5.8), camphene (1.6–5.7)Chizzola [30]
Peucedanum austriacum (Jacq.) W.D.J. Koch [aus] 1As in cited articlePteroselinum austriacum (Jacq.) Rchb.β-Phellandrene (45.2), α-pinene (10.1), germacrene D (6.4), (E)-caryophyllene (6.1), germacrene B (5.6)Jovanović et al. [32]
Peucedanum cervaria (L.) Lapeyr. [cer1]As in cited articleCervaria rivini Gaertn.α-Pinene (31.3), sabinene (31.0), β-pinene (21.7)Skalicka-Woźniak et al. [31]
Peucedanum cervaria (L.) Lapeyr. [cer2] β-Pinene (33.1), α-pinene (22.3), sabinene (22.0), limonene + β-phellandrene (8.4)Chizzola [30]
Peucedanum chryseum (Boiss. & Heldr.) Chamberlain [chr]Dichoropetalum chryseum (Boiss. & Heldr.) Pimenov & KljuykovDichoropetalum chryseum (Boiss. & Heldr.) Pimenov & Kljuykovα-Pinene (72.8), β-pinene (20.4)Ağalar et al. [33]
Peucedanum dhana Buch.-Ham. ex C.B. Clarke
[dha] 1,2		As in cited articleAs in cited articletrans-Piperitol (51.2), β-pinene (11.7), o-cymene (11.1), γ-terpinene (9.2)Khruengsai et al. [34]
Peucedanum officinale L.
[off] 1,2		As in cited articleAs in cited articleFenchone (32.0), (E)-β-ocimene (17.8), (Z)-β-ocimene (9.4), γ-terpinene (6.8), p-cymene (6.3), α-acorenol (5.0)Jaimand et al. [14]
Peucedanum oreoselinum (L.) Moench [ore1] 1As in cited articleOreoselinum nigrum DelarbreLimonene (17.9), α-pinene (17.7), sabinene (16.5), β-pinene (14.4), (Z)-β-ocimene (12.9)Silva et al. [35]
Peucedanum oreoselinum
(L.) Moench [ore2-8] 1		 Four samples: limonene (44.1–56.6), γ-terpinene (12.2–17.5), β-pinene (8.5–14.5), α-pinene (5.1–8.3), α-phellandrene (3.5–4.1);
two samples: limonene (76.0–82.4), sabinene (4.6–8.0), α-pinene (4.0–6.3)		Motskute & Nivinskene [36]
Peucedanum palustre (L.) Moench [pal] 1As in cited articleThysselinum palustre (L.) Hoffm.Limonene (87.5), γ-terpinene (9.1)Schmaus et al. [37]
Peucedanum petiolare (DC.) Boiss. [pet]Leutea petiolaris (DC.) PimenovLeutea petiolaris (DC.) Pimenovα-Pinene (47.3), sabinene (45.9)Mirza et al. [38]
Peucedanum ruthenicum M.Bieb. [rut] 1,2As in cited articleAs in cited articleCaryophyllene oxide (13.6), 8,9-dehydroisolongifolene (11.3), 1,8-cineole (11.1), (Z)-carveol (6.9), camphor (5.9), carvone (5.6), caryophylla-4(12),8(13)-dien-5-β-ol (5.2)Alavi et al. [39]
Peucedanum tauricum M.Bieb. [tau] 1,2As in cited article Guaia-9,11-diene (28.6), guaia-1(10),11-diene (26.1)Bartnik [15]
Peucedanum verticillare (L.) W.D.J.Koch ex DC. [ver] 1As in cited articleTommasinia altissima (Mill.) Reduron(E)-Caryophyllene (24.2), α-phellandrene (20.8), (Z)-β-farnesene (12.8), β-bisabolene (9.0), β-cubebene (7.5), caryophyllene oxide (6.7), α-trans-bergamotene (5.3), geranyl acetate (5.0)Fraternale et al. [16]
Peucedanum longifolium Waldst. & Kit. [lon] 1,2Peucedanum officinale subsp. longifolium (Waldst. & Kit.) R.FreyAs in current workα-Phellandrene (26.2), β-phellandrene + limonene (21.0), myrcene (9.5), germacrene B (9.5), p-cymene (7.9)Current work
Rhizomatophora aegopodioides (Boiss.) Pimenov [aeg]As in current workAs in current workn-Undecane (16.5), n-nonane (11.3), (E)-sesquilavandulol (10.0), hexadecanoic acid (9.6)Current work
1 Peucedanum in the broad sense (sensu lato). 2 Peucedanum in the narrow sense (sensu stricto).
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Ušjak, L.; Niketić, M.; Petrović, S. Composition of Essential Oils from Fruits of Peucedanum longifolium and Rhizomatophora aegopodioides (Apiaceae) with Regard to Other Related Taxa—A Chemometric Approach. Separations 2024, 11, 14. https://doi.org/10.3390/separations11010014

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Ušjak L, Niketić M, Petrović S. Composition of Essential Oils from Fruits of Peucedanum longifolium and Rhizomatophora aegopodioides (Apiaceae) with Regard to Other Related Taxa—A Chemometric Approach. Separations. 2024; 11(1):14. https://doi.org/10.3390/separations11010014

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Ušjak, Ljuboš, Marjan Niketić, and Silvana Petrović. 2024. "Composition of Essential Oils from Fruits of Peucedanum longifolium and Rhizomatophora aegopodioides (Apiaceae) with Regard to Other Related Taxa—A Chemometric Approach" Separations 11, no. 1: 14. https://doi.org/10.3390/separations11010014

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