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Article

Chemical Composition of the Essential Oils of the Iberian Peninsula Endemic Species Eryngium dilatatum Lam.

by
Jesús Palá-Paúl
1,*,
María José Pérez-Alonso
1,
Ana C. Soria
2 and
Joseph J. Brophy
3
1
Departamento de Biodiversidad, Ecología y Evolución, Facultad de Ciencias Biológicas, Universidad Complutense de Madrid, 28040 Madrid, Spain
2
Instituto de Química Orgánica General (IQOG-CSIC), Juan de la Cierva 3, 28006 Madrid, Spain
3
School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia
*
Author to whom correspondence should be addressed.
Molecules 2024, 29(3), 562; https://doi.org/10.3390/molecules29030562
Submission received: 5 December 2023 / Revised: 8 January 2024 / Accepted: 19 January 2024 / Published: 23 January 2024
(This article belongs to the Collection Essential Oils)
Browse Figure
Versions Notes

Abstract

:
Eryngium dilatatum Lam. is a thorny Iberian Peninsula endemic species belonging to the Apiaceae family that has not been previously analysed from a chemical point of view. Following our studies on this genus, we characterized the chemical composition of the essential oils from the different parts (inflorescences, stems + leaves, and roots) of this species; these parts were gathered in Cádiz (Spain). The specimens were collected in July during the flowering period and air-dried before the oil extraction by hydro-distillation. The essential oils were analysed by gas chromatography and gas chromatography coupled with mass spectrometry. The different parts of the plant yielded low amounts of pale yellow oil, with the roots being the fraction that provided the lowest amount of oil. The chemical characterization of the essential oils showed qualitative and quantitative differences between the fractions examined, but all of them showed the same principal compound, germacrene D (9.1–46.5%). Similarly, all the fractions shared most of their representative constituents, with their percentage compositions being different from one sample to the other: α-cadinol (3.8%), bicyclogermacrene (3.5%), octanal (3.1%), and spathulenol (2.5%) were found in the inflorescences; octanal (8.1%), α-cadinol (3.7%), δ-cadinene (3.6%), (E)-caryophyllene (2.6%), bicyclogermacrene (2.5%), and spathulenol (2.4%) were found in the stems and leaves; and spathulenol (4.6%), α-cadinol (4.4%), khusinol (3.2%), α-muurolol (3.1%), and δ-cadinene (2.6%) were found in the roots. As far as we know, this is the first report about the chemical composition of this endemic species of the Iberian Peninsula. It contributes to the knowledge of this species and to the genus to which it belongs. This species could be considered as a natural source of germacrene D, which is a sesquiterpene hydrocarbon with active properties.

1. Introduction

The genus Eryngium L. belongs to the Apiaceae family and, with about 250 species, has a cosmopolitan distribution. This genus includes annual and perennial herbs with hairless and spiny leaves, which present dome-shaped umbels of steely blue or white flowers with whorls of spiny basal bracts. Only fourteen of the twenty-six species described in Flora Europaea grow wildly in the Iberian Peninsula [1]. Eryngium dilatatum Lam. is a perennial herb (from 5 to 40 cm) with erect stems that are rarely branched; their basal leaves, which are slightly coriaceous and obovate, are persistent. From June to August, it presents bluish inflorescences in pedunculated capitula from 0.5 to 1.5 cm. E. dilatatum is one of the four Eryngium species endemic to the Iberian Peninsula. It grows in dry places in Portugal and Spain with a disjunct distribution (Figure 1).
Despite the high number of species belonging to this genus, only a few of them have previously been investigated. With regard to the species distributed in the Iberian Peninsula, this could be caused by the small size of some species, such as E. tenue Desf. or E. galioides Lam., their spiny leaves that make their recollection and study difficult, or the inaccessible environment where they grow, as in the case of E. glaciale Boiss. or E. bourgatii Gouan. In general, most of the studies related to this genus could be grouped according to their chemistry (flavonoids, phenolic contents, phytochemistry, etc.), genetic diversity, and biological properties (analgesic, antibacterial, anticlastogenic, anti-inflammatory, antimicrobial, antioxidant, cytotoxic activity, larvicidal, long-term memory, molluscicidal, parasiticidal, etc.) [2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19,20,21,22,23,24,25,26,27,28,29,30,31,32,33,34]. The essential oils of the Eryngium genus have not been widely investigated; the majority of the reports addressing their compositions have been published in the last 20 years [35,36,37,38,39,40,41,42,43,44,45,46,47,48,49,50,51,52,53,54,55,56,57,58,59,60,61,62,63,64,65,66,67,68,69,70,71,72,73,74,75,76,77,78,79,80,81,82,83,84,85,86].
The main compounds and the yield, as given by the data that are available, of the essential oils extracted from the species which grow in the Iberian Peninsula are shown in Table 1. It is worth noting that only seven of the fourteen species present in this area have been analysed. According to these results, the Eryngum genus shows low amounts of essential oils with yields varying between 0.1 and 0.82%. Normally, the fraction with the highest amount of oil is the one corresponding to the inflorescences, which could be related to the pollination of the species. However, the species studied to date showed different chemical compositions according to their ecology. We found that the species that grow at high altitudes under hard climatic conditions contain a large amount of diterpenes; these are the compounds that make up the predominant fraction of the oil in Eryngium bourgatii Gouan [73] and E. glaciale Boiss. [74]. In fact, the altitude seems to affect the chemical composition of the Iberian endemic species E. duriaei J. Gay ex Boiss. The populations of this species that grow below 1700 m showed α-neocallitropsene (28–53%), β-betulenal (8.5–15.8%), and 14-hydroxy-β-caryophyllene (5.8–13.7%) as the main compounds, while caryophyllene oxide (47%) and E-caryophyllene (6%) were identified in the analysed population growing above this altitude [56]. E. maritimum L. [81] is a species that grows in sandy places on the coast and contains sesquiterpenes as its principal fraction, while monoterpenes are the largest fraction in the oils of E. corniculatum Lam. [71], which grows on the margins of seasonal lakes. The studies on the chemical composition of E. campestre growing under different soil types have also been reported [69].
Table 1. Main constituents of the essential oils of the Eryngium species growing wild in the Iberian Peninsula.
Table 1. Main constituents of the essential oils of the Eryngium species growing wild in the Iberian Peninsula.
SpeciesMain ComponentsYield (%)Ref.
E. aquifolium Cav.Inflorescence oil: germacrene D (30.3%) and sesquicineole (26.7%)0.81[65]
Stem and leaf oil: germacrene D (46.0%) and myrcene (13.8%)0.41
Root oil: phyllocladene isomer (63.6%)0.18
E. bourgatii GouanInflorescence oil: phyllocladene (37.6%) and bicyclogermacrene (15.1%)0.33[73]
Stem and leaf oil: phyllocladene (20.4%), γ-muurolene (11.8%) and (E)-caryophyllene (10.1%)0.11
Root oil: γ-muurolene (15.4%) and phyllocladene (15.0%)0.20
E. campestre L.Inflorescence oil: germacrene D (30.3–40.3%), β-curcumene (0.7–22.2%), myrcene (3.0–21.7%), (E)-β-farnesene (0.1–19.0%).0.1–0.4[69]
Stem and leaf oil: germacrene D (31.1–42.4%), myrcene (0.5–23.15)0.1–0.2
E. corniculatum Lam.Inflorescence oil: 2,4,6-trimethylbenzaldehyde (50.8%), α-pinene (4.0%)0.82[72]
Stem and leaf oil: 2,4,6-trimethylbenzaldehyde (50.0%), 2,4,5-trimethylbenzaldehyde (3.8%)0.49
Root oil: 2,4,6-trimethylbenzaldehyde (29.8%), phyllocladene isomer (13.0%), (E)-nerolidol (9.4%)0.22
E. duriaei J. Gay ex Boiss.Populations below 1700 m: α-neocallitropsene (28–53%), β-betulenal (8.5–15.8%) and 14-hydroxy-β-caryophyllene (5.8–13.7%)0.2–0.3[56]
Population over 1700 m: caryophyllene oxide (47%) and E-caryophyllene (6%)
E. glaciale Boiss.Inflorescence oil: phyllocladene isomer (43.5%), (E)-caryophyllene (15.2%) and valencene (11.5%)0.16[74]
Stem and leaf oil: phyllocladene isomer (41.3%)0.26
Root oil: phyllocladene isomer (49.4%) and linalool (19.1%).0.30
E. maritimum L.Aerial parts: germacrene D (43.1–42.4%) and 9-muurolen-15-aldehyde (22.4–16.4%)--[81]
Roots: γ-guaiene (40.2%), 2,3,4-trimethylbenzaldehyde (24.5%) and germacrene D (10.6%)--
Nowadays, there is a great concern about biodiversity conservation and the modification of habitats caused by the climatic change, particularly in areas that are susceptible to extended droughts, such as in Spain. One of the best ways to contribute to this conservation is to provide as much knowledge as possible on the ecological valence of species growing wild in these areas. Following our work with other Eryngium species, the aim of this particular study was to analyse the essential oils of the different parts of E. dilatatum and to compare their chemical composition with those of the other Iberian species studied to date. This study contributes to the deepening of the knowledge on the chemical composition of the species of the Eryngium genus. Deepening the knowledge on the variability and wealth of compounds that this genus presents is essential to the understanding of its diversity and adaptation to the different environments where it grows. As far as we know, this is the first report on the volatile components of this species which is endemic to the Iberian Peninsula.

2. Results and Discussion

The different fractions, voucher numbers, locality, and oil yield of the population of E. dilatatum considered in this work are presented in Table 2. According to these results, the aerial fractions showed a similar yield (0.29–0.33%), whereas the roots produced a low amount of oil (0.14%). These results are in agreement with those previously reported for other Iberian species of this genus (Table 1). Usually, the roots are the part of the plant with lowest amount of oil. Most of the Eryngium species are perennial or geophyte plants; so, they can synthesize or accumulate oil in this part of the plant during the winter. In fact, perennial species growing at a high altitude seem to accumulate oils in this part of the plant (E. bourgatii and E. glaciale). As has previously been proposed for this genus [13,56,69,71,77], the type of soil, the climatic conditions, and the water availability could affect the production of essential oil. The species that grow in dry places contain low amounts of oils (0.1–0.33%), while the species that grow close to lakes (e.g., E. corniculatum) show higher amounts of oil (0.22–0.82%) [72]. The available water seems to affect the metabolic route of the terpenoid compounds in this genus, proving the adaptation of the species to the environment where they grow. However, this hypothesis should be confirmed under controlled experimental conditions or by in vitro cultures of each species. Another species of this genus growing in a similar habitat, E. aquifolium [65], showed a yield that was two times higher in the inflorescences, which could contribute to the pollination success. It would be interesting to study the phenology of the essential oils of E. dilatatum to determine their variation during the year and the possible effect of the flowering and fruiting period. Additionally, those phenology studies could also be carried out on different populations to evaluate whether the yield and chemical composition of the essential oils of this species vary according to ecological factors, as has previously been reported for other species of this genus [56,69]. However, the present study was a first contribution to the chemical composition of this species; therefore, it was limited to a single population.
The components identified from the different parts of Eryngium dilatatum, their retention indices, and their percent composition are summarised in Table 3, where all the compounds are arranged in order of their elution on the DB-1 column. The retention indices of these compounds on a DB-Wax column are also listed in brackets in this table. A total of 79 compounds were identified, representing 76.2–97.3% of the total oil obtained from the different parts of the plant studied. As we mentioned above, the root fraction was the source of the lowest amount of oil but, with regard to the chemical composition, few qualitative or quantitative differences in the oil content of the three fractions analysed were observed. Although all the fractions analysed showed the same principal compound, germacrene D (9.1–46.5%), and shared most of their representative constituents, their percentage compositions differed with the plant part considered: α-cadinol (3.8%), bicyclogermacrene (3.5%), octanal (3.1%), spathulenol (2.5%), and α-muurolol (2.5%) were found in the inflorescences; octanal (8.1%), α-cadinol (3.7%), δ-cadinene (3.6%), (E)-caryophyllene (2.6%), bicyclogermacrene (2.5%), and spathulenol (2.4%) were found in the stems and leaves; and spathulenol (4.6%), α-cadinol (4.4%), khusinol (3.2%), α-muurolol (3.1%), δ-cadinene (2.6%), 14-oxy-α-muurolene (2.6%), and carotol (2.5%) were found in the roots. Five compounds could not be identified, and their mass spectral fragmentation patterns are provided at the end of Table 3.
The same main compound was identified in all the analysed fractions. Other species of this genus also shared their major constituents, although each species seems to have plasticity in the chemical composition. To date, the studied species growing in the Iberian Peninsula show two patterns, E. bourgatii, E. campestre, E. corniculatum, E. glaciale, and E. dilatatum share the same principal compounds in their different fractions, while the root fractions of E. aquifolium and E. maritimum do not have the same components (Table 1). It would be interesting to analyse the phenology of the essential oils of this species to check whether the season affects its metabolism and the production of terpenoids and their location in the plant. However, the variability of this genus occurs in other species of the same family, where different fractions either share the main compound [87,88] or do not [89,90,91,92,93,94,95,96].
Table 3. Essential oil composition (%) of the different parts of Eryngium dilatatum Lam. from Spain.
Table 3. Essential oil composition (%) of the different parts of Eryngium dilatatum Lam. from Spain.
CompoundII 1E.d.IE.d.SLE.d.R
1-(1-methyl-2-cyclopenten-1-yl)-ethanone885--0.62.1t
α-Pinene932 (1012)9322.10.50.2
Sabinene963 (1113)969tt0.1
β-Pinene970 (1097)974t1.10.7
Myrcene985 (1160)988t----
Octanal993 (1286)9983.18.11.7
n-Decane10001000t0.20.4
α-Phellandrene1005 (1157)1002t----
Benzene acetaldehyde100910360.10.10.4
α-Terpinene1015 (1173)1014t----
o-Cymene1019 (1268)1022t----
Limonene1026 (1191)10242.31.91.8
β-Phellandrene1027 (1201)1025t----
1,8-Cineole1029 (1204)1026t----
γ-Terpinene1058 (1240)1054t----
Acetophenone10601059tt0.1
Fenchone1074 (1392)10830.10.70.2
2-Nonanone10801087t----
Terpinolene1085 (1277)1086t----
Cryptone1087 (1669)11830.1t0.7
Nonanal10931100t----
Linalool1096 (1549)10951.01.70.2
cis-Thujone11171101tt0.3
Menthone1148 (1468)1148t----
Terpinen-4-ol1175 (1603)1174t----
α-Terpineol1183 (1700)11860.1----
n-Dodecane12001200t0.6--
n.i. 11235--0.10.4--
trans-Chrysanthenyl acetate12411235t----
Carvacrol129812980.1----
(E,Z)-2,4-Decadienal1301 (1229)1292t----
δ-Elemene1333 (1468)13350.10.40.1
α-Cubebene1345 (1455)13450.1t0.2
(Z)-β-Damascenone135413610.10.3t
α-Copaene1366 (1480)13741.01.90.6
β-Bourbonene1376 (1515)13870.71.20.5
β-Cubebene1382 (1535)1387t----
β-Elemene1387 (1587)13890.82.10.4
α-Cedrene1405 (1669)1410tt0.2
α-Gurjunene1406 (1528)1409tt0.2
β-Cedrene14091419tt0.3
(E)-Caryophyllene1410 (1594)14171.42.60.6
β-Gurjunene1426 (1595)14310.20.50.4
α-trans-Bergamotene1432 (1583)14320.1----
Aromadendrene1433 (1605)14390.20.3--
α-Guaiene143414370.40.30.9
α-neo-Clovene144514520.4----
α-Humulene1447 (1667)14521.61.80.8
cis-Muurola-4(14)-5-diene14541465t----
allo-Aromadendrene14661458t----
Germacrene D1476 (1713)148446.538.49.1
α-Selinene1492 (1727)14980.40.21.4
Bicyclogermacrene1493 (1750)15003.52.50.9
α-Muurolene1499 (1924)1500t----
γ-Cadinene1508 (1691)15130.40.70.9
trans-β-Guaiene1511 (1611)1502t----
β-Bisabolene1513 (1727)15050.1t1.6
Cubebol1515 (2068)1514t----
δ-Cadinene1522 (1760)15221.93.62.6
trans-Calamenene152715210.1t0.4
Cadina-1,4-diene1528 (1783)15330.20.50.6
α-Cadinene15391537t----
Elemol1541 (2085)1548t----
β-Calacorene155315640.2t1.2
n.i. 21557--0.70.4--
n.i. 31559--3.33.24.2
Dodecanoic acid1568 (2495)15650.30.40.8
Spathulenol1576 (2133)15772.52.44.6
Caryophyllene oxide1580 (1987)15820.3----
Striatene1582--0.80.41.5
cis-Arteannuic alcohol159215930.1----
Carotol1594 (2026)15940.71.32.5
β-Oploplenone15971607t----
n.i. 41602--1.60.72.0
n.i. 51608--0.71.02.2
β-Bazzanene1610 (1519)15190.71.02.0
Cubenol16331645t----
β-Eudesmol1638 (2239)16490.4t1.4
α-Muurolol1650 (2246)16442.52.13.1
α-Cadinol1651 (2243)16523.83.74.4
Khusinol166516791.81.33.2
Khusimol171617410.4t--
14-Oxy-α-Muurolene1745 (2016)17672.00.52.6
14-Hydroxy-α-Muurolene1757 (2026)17790.3t0.1
Total 97.387.576.2
I = Kováts retention indices on DB-1 column and on DB-Wax column in parenthesis; I 1 = literature linear retention index on DB-5 column [96]; t = traces (% < 0.1); n.i. = not identified; E.d. = Eryngium dilatatum; I = inflorescences; SL = stems and leaves; R = roots; n.i. 1 I = 1235, 136 [M+] (10), 70 (100), 55 (75), 41 (65), 83 (60), 57 (55), 69 (54), 43 (52), 98 (25), 110 (20), 121 (15); n.i. 2 I = 1557, 220 [M+] (10), 123 (100), 131 (75), 109 (43), 91 (40), 146 (39), 163 (27), 187 (9), 202 (5); n.i. 3 I = 1559, 220 [M+] (35), 135 (100), 107 (88), 159 (85), 91 (83), 121 (81), 177 (79), 81 (60), 41 (45), 55 (40), 137 (39), 69 (30), 161 (23), 205 (20), 189 (10); n.i. 4 I = 1602, 220 [M+] (15); 91 (100), 105 (85), 79 (80), 123 (65), 41 (64), 159 (60), 131 (50), 145 (50), 187 (18), 177 (13); n.i. 5 I = 1608, 222 [M+] (5), 109 (100), 81 (50), 93 (48), 41 (45), 161 (35), 67 (30), 55 (28), 119 (25), 135 (20), 204 (18), 177 (18), 189 (15).
The chemical composition of the different species of Eryngium studied to date, are qualitatively and quantitatively different, and they do not share any of the principal compounds (Table 1). Germacrene D is the only compound that appears as the principal component of four of these species (E. dilatatum, E. aquifolium, E. campestre, and E. maritimum). The habitat and climatic conditions seem to affect the chemical composition of the species within this genus; therefore, it is expected that species grown under similar ecological conditions would show similar constituents.
Other species of this genus have been reported to have analgesic, anticonvulsant, antifungal, anti-inflammatory, antimicrobial, antimutagenic, antioxidant, antiviral, cytotoxic, haemolytic, inhibitory, larvicidal, molluscicidal, or parasiticidal properties [8,9,10,11,12,13,15,16,17,19,20,25,26,28,29,30,31,39,40,41,45,46,47,49,50,51,52,53,86]. It would be interesting to check any of these properties or activities in the essential oils of this species. In the present paper, the biological properties of the essential oils from the various fractions of this species were not evaluated due to the limited amount of oil available. However, germacrene D, the major component of these oils is a hydrocarbon sesquiterpene for which a number of bioactivities have previously been reported [97,98,99,100]. It would be interesting to study the phenology of this compound in this species to evaluate the usefulness of E. dilatatum oils for attracting/repelling insects or for allopathic and antimicrobial activities.
The distribution of the terpenoid compounds in the different fractions of E. dilatatum appears at the end of Table 4. All the analysed fractions showed sesquiterpenes as the predominant group, with percentages of 91.6%, 81.6%, and 72.6% for the inflorescences, stems and leaves, and roots, respectively. In the aerial parts, the sesquiterpene hydrocarbons (61.8% and 58.4%) were more abundant than the oxygenated ones (29.8% and 23.2%). In contrast, the roots accumulated a higher amount of oxygenated sesquiterpenes (45.2%) than sesquiterpene hydrocarbons (27.4%). The monoterpene fraction was lower than 5% of the total oil, irrespective of the fraction considered, and was always higher than that of the oxygenated monoterpenes. Most of the Eryngium species studied to date that inhabit open and dry areas have sesquiterpenes as the predominant fraction, whereas the species that grow close to lakes or wet soils have high amounts of monoterpenes [72]. Other species of Eryngium growing under hard climatic conditions exhibited diterpenes as the main components [73,74]. E. campestre seems to modify its chemical composition according to the type of soil [69]. This could also be one of the reasons why none of the compounds described to date for this genus could be used for chemotaxonomy proposes.

3. Materials and Methods

3.1. Plant Material

Several specimens of Eryngium dilatatum were gathered during the summer (15-VII-1999) at flowering in Grazalema, Cádiz (Spain). A voucher specimen (MACB-73213) was lodged at the Herbarium of the Faculty of Biology, Complutense University, Madrid, Spain. More details about the locality and the fractions considered appear in Table 2.

3.2. Isolation of Volatile Oils

The different parts of Eryngium dilatatum, which included the inflorescences (I), stems and leaves (SL), and roots (R), were air-dried. Each one was cut into small pieces (<3 cm) and subjected, separately, to hydro-distillation with cohobation for 8 h according to the method recommended in the Spanish Pharmacopoeia [101] to obtain their essential oils. In brief, each fraction of the inflorescences (I), stems and leaves (SL), and roots (R) was included in a round-bottom flask. The samples were covered with distilled water, and salt (5 g/L) was added to increase the boiling point. The Clevenger apparatus was tightened to the flask, and it was heated to boiling. After 8 h, the oils were measured (mL) and gathered in topaz vials. All the oils were dried over anhydrous magnesium sulphate and stored at 4 °C in the dark. The yields, based on a dried weight basis, of the different parts analysed appear in Table 2.

3.3. Gas Chromatography (GC)

GC analysis was carried out on a Varian 3300 gas chromatograph fitted with a fused silica methyl silicone DB-1 column (50 m × 0.25 mm, 0.25 μm film thickness). The temperature was programmed from 95 °C to 240 °C at 4 °C min−1. Injection was performed at 250 °C in the split mode (1:100). Nitrogen was used as the carrier gas (1.5 mL min−1). Detection was carried out using a flame ionization detector (FID) at 300 °C. The injection volume for all the samples was 0.1 μL of pure oil.

3.4. Gas Chromatography–Mass Spectrometry (GC-MS)

GC-MS analyses were carried out using an Agilent Technologies 6890 gas chromatograph coupled to an HP 5973 mass spectrometry detector. A fused silica SE-30 capillary column (50 m × 0.25 mm, 0.25 μm film thickness) was used for separation. The column temperature was programmed from 70 °C to 220 °C at 4 °C min−1, and helium at 1 mL min−1 was used as a carrier gas. The mass spectra were recorded in the scan mode at 70 eV.
In order to confirm the identification of several compounds, the oil samples were also analysed using a VG Quattro gas chromatograph–mass spectrometer operating at 70 eV ionization energy. The GC column used was a DB-Wax (60 m × 0.32 mm, × 0.25 μm film thickness) programmed from 35 °C to 220 °C at 3 °C min−1 with helium as a carrier gas.

3.5. Qualitative and Quantitative Analyses

Most of the constituents were tentatively identified by GC via a comparison of their retention indices with those of the authentic standards available in the authors’ laboratory or with retention indices from the references [102,103,104,105,106,107,108]. Further confirmation of the identifications was achieved by GC-MS; the fragmentation patterns of the experimental mass spectra were compared with those of the mass spectral data of the WILEY and NIST libraries. The other constituents were either synthesised or identified in oils of known composition.
Semiquantitative analysis (percent data) was carried out directly from peak areas in the GC profile.

4. Conclusions

This contribution aimed to study the chemical composition of the essential oils of E. dilatatum Lam. from the Iberian Peninsula; it represents an advance in the knowledge of this rarely studied species. The different fractions analysed (inflorescences, stems and leaves and roots) yielded low amounts of essential oils. These results seem to be correlated with the environment where this species grows, as other species of this genus that inhabit sandy, dry soils also give rise to low amounts of oil. However, the oil yield of this genus is low in comparison with other tropical species of this genus and other species belonging to the same family that are widely used as culinary herbs.
E. dilatatum Lam. showed only one principal compound, Germacrene D (9.1–46.5%), which was present in all the fractions studied. Although a number of bioactive properties have previously been described for this hydrocarbon sesquiterpene, further research should be carried out to confirm its contribution to the bioactivity of E. dilatatum essential oils.
With regard to the terpenoid compounds, the essential oils of E. dilatatum showed sesquiterpenes as the predominant group in the different fractions analysed: inflorescences, stems and leaves, and roots. As compared to previous studies, it can be concluded that the Iberian Peninsula species of this genus growing under comparable conditions shows similar constituents; so, the ecological conditions seem to affect the chemical composition of this genus to a noticeable extent.

Author Contributions

Conceptualization, J.P.-P., M.J.P.-A., A.C.S. and J.J.B.; Methodology, J.P.-P., M.J.P.-A., A.C.S. and J.J.B.; Formal analysis, J.P.-P., A.C.S. and J.J.B.; Investigation, J.P.-P., M.J.P.-A., A.C.S. and J.J.B.; Resources, J.P.-P.; Writing—original draft, J.P.-P., A.C.S. and J.J.B.; Writing—review & editing, J.P.-P., A.C.S. and J.J.B.; Supervision, J.P.-P., A.C.S. and J.J.B.; Project administration, J.P.-P. 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

Data are contained within the article.

Conflicts of Interest

The authors declare no conflicts of interest.

References

  1. Tutin, T.G.; Heywood, V.H.; Burges, N.A.; Valentine, D.H.; Walters, S.M.; Webb, D.A. Flora Europaea; Cambridge University Press: Cambridge, UK, 1968; Volume 2. [Google Scholar]
  2. Al-Khalil, S. Phytochemistry of Eryngium creticum. Alex. J. Pharm. Sci. 1994, 8, 73–75. [Google Scholar]
  3. Arabpoor, B.; Yousefi, S.; Weisany, W.; Ghasemlou, M. Multifunctional coating composed of Eryngium campestre L. essential oil encapsulated in nano-chitosan to prolong the shelf-life of fresh cherry fruits. Food Hydrocoll. 2021, 111, 106394. [Google Scholar] [CrossRef]
  4. Sadiq, A.; Rashid, U.; Ahmad, S.; Zahoor, M.; AlAjmi, M.F.; Ullah, R.; Noman, O.M.; Ullah, F.; Ayaz, M.; Khan, I.; et al. Treating hyperglycemia from Eryngium caeruleum M. Bieb: In-vitro alpha-glucosidase, antioxidant, in-vivo antidiabetic and molecular docking-based approaches. Front. Chem. 2020, 8, 558641. [Google Scholar] [CrossRef] [PubMed]
  5. Beeby, E.; Magalhaes, M.; Pocas, J.; Collins, T.; Lemos, M.F.L.; Barros, L.; Ferreira, I.C.F.R.; Cabral, C.; Pires, I.M. Secondary metabolites (essential oils) from sand-dune plants induce cytotoxic effects in cancer cells. J. Ethnopharmacol. 2020, 258, 112803. [Google Scholar] [CrossRef] [PubMed]
  6. Minh, P.N. Influence of extraction parameters on total phenolic contents, flavonoids and antioxidant capacity of extract from Eryngium foetidum leaves. Biosci. Res. 2020, 3, 1822–1829. [Google Scholar]
  7. Rosero-Gomez, C.A.; Lorena Zambrano, M.A.; Garcia, K.E.; Viracocha, L.A. Names and uses of the Culantro de Monte (Erygium foetidum L.) in the San Antonio de Padua community, Los Rios-Ecuador. Bol. Latinoam. Caribe Plantas Med. Aromat. 2020, 19, 334–343. [Google Scholar]
  8. Landoulsi, A.; Hennebelle, T.; Bero, J.; Riviere, C.; Sahpaz, S.; Quetin-Leclercq, J.; Neut, C.; Benhamida, J.; Roumy, V. Antimicrobial and Light-Enhanced Antimicrobial Activities, Cytotoxicity and Chemical Variability of All Tunisian Eryngium Species. Chem. Biodivers. 2020, 17, e1900543. [Google Scholar] [CrossRef]
  9. Mirahmadi, S.S.; Aminzare, M.; Azar, H.H.; Kamali, K. Effect of Eryngium caeruleum essential oil on microbial and sensory quality of minced fish and fate of Listeria monocytogenes during the storage at 4 degrees C. J. Food Saf. 2020, 40, e12745. [Google Scholar] [CrossRef]
  10. Daneshzadeh, M.S.; Abbaspour, H.; Amjad, L.; Nafchi, A.M. An investigation on phytochemical, antioxidant and antibacterial properties of extract from Eryngium billardieri F. Delaroche. J. Food Meas. 2020, 14, 708–715. [Google Scholar] [CrossRef]
  11. de Carvalho Augusto, R.; Merad, N.; Rognon, A.; Gourbal, B.; Bertrand, C.; Djabou, N.; Duval, D. Molluscicidal and parasiticidal activities of Eryngium triquetrum essential oil on Schistosoma mansoni and its intermediate snail host Biomphalaria glabrata, a double impact. Parasites Vectors 2020, 13, 486. [Google Scholar] [CrossRef]
  12. Vukic, M.D.; Vukovic, N.L.; Djelic, G.T.; Obradovic, A.; Kacaniova, M.M.; Markovic, S.; Popovic, S.; Baskic, D. Phytochemical analysis, antioxidant, antibacterial and cytotoxic activity of different plant organs of Eryngium serbicum L. Ind. Crop. Prod. 2018, 115, 88–97. [Google Scholar] [CrossRef]
  13. Lajnef, H.B.; Ferioli, F.; Pasini, F.; Politowicz, J.; Khaldi, A.; D’Antuono, F.; Caboni, M.F.; Nasri, N. Chemical composition and antioxidant activity of the volatile fraction extracted from air-dried fruits of Tunisian Eryngium maritimum L. ecotypes. J. Sci. Food Agric. 2017, 98, 635–643. [Google Scholar] [CrossRef]
  14. Raeisi, S.; Ojagh, S.M.; Sharifi-Rad, M.; Sharifi-Rad, J.; Quek, S.Y. Evaluation of Allium paradoxum (MB) G. Don. and Eryngium caucasicum trauve. Extracts on the shelf-life and quality of silver carp (Hypophthalmichthys molitrix) fillets during refrigerated storage. J. Food Safety 2017, 37, e12321. [Google Scholar] [CrossRef]
  15. Fallahzadeh, A.R.; Zarei, M.; Mohammadi, S. Preliminary Phytochemical Screening, Analgesic and Anti-inflammatory effect of Eryngium pyramidale Boiss. & Husson Essential Oil in Male Rat. Entomol. Appl. Sci. Lett. 2016, 3, 140–147. [Google Scholar]
  16. Kikowska, M.; Dworacka, M.; Kedziora, I.; Thiem, B. Eryngium creticum–Ethnopharmacology, phytochemistry and pharmacological activity. A review. Rev. Bras. Farmacogn. 2016, 26, 392–399. [Google Scholar] [CrossRef]
  17. Erdem, S.A.; Nabavi, S.F.; Orhan, I.E.; Daglia, M.; Izadi, M.; Nabavi, S.M. Blessings in disguise: A review of phytochemical composition and antimicrobial activity of plants belonging to the genus Eryngium. DARU J. Pharm. Sci. 2015, 23, 53. [Google Scholar] [CrossRef]
  18. Ozarowski, M.; Thiem, B.; Mikolajczak, P.L.; Piasecka, A.; Kachlicki, P.; Szulc, M.; Kaminska, E.; Bogacz, A.; Kujawski, R.; Bartkowiak-Wieczorek, J.; et al. Improvement in Long-Term Memory following Chronic Administration of Eryngium planum Root Extract in Scopolamine Model: Behavioral and Molecular Study. Evid.-Based Complement. Altern. Med. 2015, 2015, 145140. [Google Scholar] [CrossRef] [PubMed]
  19. Rufino, A.T.; Ferreira, I.; Judas, F.; Salgueiro, L.; Celeste Lopes, M.; Cavaleiro, C.; Mendes, A.F. Differential effects of the essential oils of Lavandula luisieri and Eryngium duriaei subsp. juresianum in cell models of two chronic inflammatory diseases. Pharm. Biol. 2015, 53, 1220–1230. [Google Scholar] [CrossRef]
  20. Sumitha, K.V.; Prajitha, V.; Sandhya, V.N.; Anjana, S.; Thoppil, J.E. Potential Larvicidal Principles in Eryngium foetidum L. (Apiaceae), An Omnipresent Weed, Effective Against Aedes albopictus Skuse. J. Essent. Oil-Bear. Plants 2014, 17, 1279–1286. [Google Scholar] [CrossRef]
  21. Singh, B.K.; Ramakrishna, Y.; Ngachan, S.V. Spiny coriander (Eryngium foetidum L.): A commonly used, neglected spicing-culinary herb of Mizoram, India. Genet. Resour. Crop. Evol. 2014, 61, 1085–1090. [Google Scholar] [CrossRef]
  22. Darriet, F.; Znini, M.; Majidi, L.; Muselli, A.; Hammouti, B.; Bouyanzer, A.; Costa, J. Evaluation of Eryngium maritimum Essential Oil as Environmentally Friendly Corrosion Inhibitor for Mild Steel in Hydrochloric Acid Solution. Int. J. Electrochem. Sci. 2013, 8, 4328–4345. [Google Scholar] [CrossRef]
  23. Promkum, C.; Butryee, C.; Tuntipopipat, S.; Kupradinun, P. Anticlastogenic Effect of Eryngium foetidum L. Assessed by Erythrocyte Micronucleus Assay. Asian Pac. J. Cancer Prev. 2012, 13, 3343–3347. [Google Scholar] [CrossRef] [PubMed]
  24. Paul, J.H.A.; Seaforth, C.E.; Tikasingh, T. Eryngium foetidum L.: A review. Fitoterapia 2011, 82, 302–308. [Google Scholar] [CrossRef] [PubMed]
  25. Çelik, A.; Aydınlık, N.; Arslan, I. Phytochemical constituents and inhibitory activity towards methicillin-resistant Staphylococcus aureus strains of Eryngium species (Apiaceae). Chem. Biodivers. 2011, 8, 454–459. [Google Scholar] [CrossRef] [PubMed]
  26. Khader, M.; Bresgen, N.; Eckl, P.M. Antimutagenic effects of ethanolic extracts from selected Palestinian medicinal plants. J. Ethnopharmacol. 2010, 127, 319–324. [Google Scholar] [CrossRef] [PubMed]
  27. Saeedi, M.; Morteza-Semnani, K. Penetration-Enhancing Effect of the Essential Oil and Methanolic Extract of Eryngium bungei on Percutaneous Absorption of Piroxicam through Rat Skin. J. Essent. Oil-Bear. Plants 2009, 12, 728–741. [Google Scholar] [CrossRef]
  28. Alkofahi, A.; Sallal, A.J.; Disi, A.M. Effect of Eryngium creticum on the haemolytic activities of snake and scorpion venoms. Phytother. Res. 2007, 11, 540–542. [Google Scholar] [CrossRef]
  29. García, M.D.; Saenz, M.T.; Gómez, M.A.; Fernández, M.A. Topical anti-inflamatory activity of phytosterols isolated from Eryngium foetidum on chronic and acute inflammation models. Phytother. Res. 1999, 13, 78–80. [Google Scholar] [CrossRef]
  30. Saenz, M.T.; Fernández, M.A.; García, M.D. Anti-inflammatory and analgesic properties from leaves of Eryngium foetidum L. (Apiaceae). Phytother. Res. 1998, 11, 380–383. [Google Scholar] [CrossRef]
  31. Khademi, S.B.; Aminzare, M.; Azar, H.H.; Mehrasbi, M.R. Eryngium caeruleum essential oil as a promising natural additive: In vitro antioxidant properties and its effect on lipid oxidation of minced rainbow trout meat during storage at refrigeration temperature. Funct. Foods Health Dis. 2021, 11, 11–23. [Google Scholar] [CrossRef]
  32. Cárdenas-Valdovinos, J.G.; García-Ruiz, I.; Angoa-Pérez, M.V.; Mena-Violante, H.G. Ethnobotany, Biological Activities and Phytochemical Compounds of Some Species of the Genus Eryngium (Apiaceae), from the Central-Western Region of Mexico. Molecules 2023, 28, 4094. [Google Scholar] [CrossRef] [PubMed]
  33. Nakurte, I.; Berga, M.; Mežaka, I. Phytochemical Diversity Comparison in Leaves and Roots of Wild and Micropropagated Latvian Sea Holly (Eryngium maritimum L.). Molecules 2023, 28, 3924. [Google Scholar] [CrossRef] [PubMed]
  34. Kikowska, M.; Chanaj-Kaczmarek, J.; Derda, M.; Budzianowska, A.; Thiem, B.; Ekiert, H.; Szopa, A. The Evaluation of Phenolic Acids and Flavonoids Content and Antiprotozoal Activity of Eryngium Species Biomass Produced by Biotechnological Methods. Molecules 2022, 27, 363. [Google Scholar] [CrossRef]
  35. Ekhtiyari, M.S.; Moradkhani, S.; Ebadi, A.; Dastan, D. Chemical Composition of the Essential Oils from the Aerial Parts of Eryngium bornmuelleri. Chem. Nat. Compd. 2020, 56, 1154–1155. [Google Scholar] [CrossRef]
  36. Rodrigues, T.L.M.; Castro, G.L.S.; Viana, R.G.; Gurgel, E.S.C.; Silva, S.G.; de Oliveira, M.S.; de Aguiar Andrade, E.H. Physiological performance and chemical compositions of the Eryngium foetidum L. (Apiaceae) essential oil cultivated with different fertilizer sources. Nat. Prod. Res. 2020, 35, 5544–5548. [Google Scholar] [CrossRef] [PubMed]
  37. Kikowska, M.; Kalemba, D.; Dlugaszewska, J.; Thiem, B. Chemical Composition of Essential Oils from Rare and Endangered Species-Eryngium maritimum L. and E. alpinum L. Plants 2020, 9, 417. [Google Scholar] [CrossRef] [PubMed]
  38. Medbouhi, A.; Benbelaïd, F.; Djabou, N.; Beaufay, C.; Bendahou, M.; Quetin-Leclercq, J.; Tintaru, A.; Costa, J.; Muselli, A. Essential Oil of Algerian Eryngium campestre: Chemical Variability and Evaluation of Biological Activities. Molecules 2019, 24, 2575. [Google Scholar] [CrossRef] [PubMed]
  39. Hamedi, A.; Pasdaran, A.L.; Pasdaran, A. Antimicrobial Activity and Analysis of the Essential Oils of Selected Endemic Edible Apiaceae Plants Root from Caspian Hyrcanian Region (North of Iran). Pharm. Sci. 2019, 5, 138–144. [Google Scholar] [CrossRef]
  40. Tel-Çayan, G.; Duru, M.E. Chemical characterization and antioxidant activity of Eryngium pseudothoriifolium and E. thorifolium essential oils. J. Res. Pharm. 2019, 23, 1106–1114. [Google Scholar] [CrossRef]
  41. Matejić, J.S.; Stojanović-Radić, Z.Z.; Ristić, M.S.; Veselinovic, J.B.; Zlatkovic, B.K.; Marin, P.D.; Dzamic, A.M. Chemical characterization, in vitro biological activity of essential oils and extracts of three Eryngium L. species and molecular docking of selected major compounds. J. Food Sci. Technol. 2018, 55, 2910–2925. [Google Scholar] [CrossRef]
  42. Medbouhi, A.; Merad, N.; Khadir, A.; Bendahou, M.; Djabou, N.; Costa, J.; Muselli, A. Chemical Composition and Biological Investigations of Eryngium triquetrum Essential Oil from Algeria. Chem. Biodivers. 2018, 15, e1700343. [Google Scholar] [CrossRef] [PubMed]
  43. Sodeifian, G.; Sajadian, S.A.; Ardestani, N.S. Experimental optimization and mathematical modeling of the supercritical fluid extraction of essential oil from Eryngium billardieri: Application of simulated annealing (SA) algorithm. J. Supercrit. Fluids 2017, 127, 146–157. [Google Scholar] [CrossRef]
  44. Cianfaglione, K.; Blomme, E.E.; Quassinti, L.; Bramucci, M.; Lupidi, G.; Dall’Acqua, S.; Maggi, F. Cytotoxic Essential Oils from Eryngium campestre and Eryngium amethystinum (Apiaceae) Growing in Central Italy. Chem. Biodivers. 2017, 14, e1700096. [Google Scholar] [CrossRef] [PubMed]
  45. Landoulsi, A.; Roumy, V.; Duhal, N.; Skhiri, F.H.; Rivière, C.; Sahpaz, S.; Neut, C.; Benhamida, J.; Hennebelle, T. Chemical Composition and Antimicrobial Activity of the Essential Oil from Aerial Parts and Roots of Eryngium barrelieri Boiss. and Eryngium glomeratum Lam. from Tunisia. Chem. Biodivers. 2016, 13, 1720–1729. [Google Scholar] [CrossRef] [PubMed]
  46. Casiglia, S.; Bruno, M.; Rosselli, S.; Senatore, F. Chemical Composition and Antimicrobial Activity of the Essential Oil from Flowers of Eryngium triquetrum (Apiaceae) Collected Wild in Sicily. Nat. Prod. Commun. 2016, 11, 1019–1024. [Google Scholar] [CrossRef] [PubMed]
  47. Klein-Júnior, L.C.; dos Santos Passos, C.; Tasso de Souza, T.J.; Gobbi de Bitencourt, F.; Salton, J.; de Loreto Bordignon, S.A.; Henriques, A.T. The monoamine oxidase inhibitory activity of essential oils obtained from Eryngium species and their chemical composition. Pharm. Biol. 2016, 54, 1071–1076. [Google Scholar] [CrossRef] [PubMed]
  48. Chandrika, R.; Saraswathi, K.J.T.; Mallavarapu, G.R. Constituents of the Essential Oils of the Leaf and Root of Eryngium foetidum L. from Two Locations in India. J. Essent. Oil-Bear. Plants 2015, 18, 349–358. [Google Scholar] [CrossRef]
  49. Merghache, D.; Boucherit-Otmani, Z.; Merghache, S.; Chikhi, I.; Selles, C.; Boucherit, K. Chemical composition, antibacterial, antifungal and antioxidant activities of Algerian Eryngium tricuspidatum L. essential oil. Nat. Prod. Res. 2014, 28, 795–807. [Google Scholar] [CrossRef]
  50. Ngang, J.J.E.; Nyegue, M.A.; Ndoye, F.C.; Kamgain, A.D.T.; Kamdem, S.L.S.; Lanciotti, R.; Gardini, F.; Etoa, F.X. Characterization of Mexican Coriander (Eryngium foetidum) Essential Oil and Its Inactivation of Listeria monocytogenes In Vitro and during Mild Thermal Pasteurization of Pineapple Juice. J. Food Prot. 2014, 77, 435–443. [Google Scholar] [CrossRef]
  51. Dehghanzadeh, N.; Ketabchi, S.; Alizadeh, A. Essential oil composition and antibacterial activity of Eryngium caeruleum grown wild in Iran. J. Essent. Oil-Bear. Plants 2014, 17, 486–492. [Google Scholar] [CrossRef]
  52. Marcetic, M.; Petrovic, S.; Milenkovic, M.; Vujisic, L.J.; Tesevic, V.; Niketic, M. Composition and antimicrobial activity of root essential oil of Balkan endemic species Eryngium palmatum. Chem. Nat. Compd. 2014, 49, 11401142. [Google Scholar] [CrossRef]
  53. Darriet, F.; Andreani, S.; De Cian, M.C.; Costa, J.; Muselli, A. Chemical variability and antioxidant activity of Eryngium maritimum L. essential oils from Corsica and Sardinia. Flavour Fragr. J. 2014, 29, 3–13. [Google Scholar] [CrossRef]
  54. Dunkić, V.; Vuko, E.; Bezić, N.; Kremer, D.; Ruščić, M. Composition and Antiviral Activity of the Essential Oils of Eryngium alpinum and E. amethystinum. Chem. Biodiver. 2013, 10, 1894–1902. [Google Scholar] [CrossRef] [PubMed]
  55. Maggio, A.; Bruno, M.; Formisano, C.; Rigano, D.; Senatore, 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, 841–844. [Google Scholar] [CrossRef]
  56. Tavares, A.C.; Loureiro, J.; Cavaleiro, C.; Salgueiro, L.; Canhoto, J.M.; Paiva, J. Characterization and distinction of two subspecies of Eryngium duriaei J. Gay ex Boiss., an Iberian endemic Apiaceae, using flow cytometry and essential oils composition. Plant Syst. Evol. 2013, 299, 611–618. [Google Scholar] [CrossRef]
  57. Mohammadhosseini, M. Hydrodistilled Volatile Oil from Stems of Eryngium creticum Lam. in the Marginal Brackish Regions of Semnan Province by Using Gas Chromatography Combined with Mass Spectrometry. Asian J. Chem. 2013, 25, 390–392. [Google Scholar] [CrossRef]
  58. Mohammadhosseini, M.; Mahdavi, B.; Akhlaghi, H. Characterization and Chemical Composition of the Volatile Oils from Aerial Parts of Eryngium bungei Bioss. (Apiaceae) by Using Traditional Hydrodistillation, Microwave Assisted Hydrodistillation and Head Space Solid Phase Microextraction Methods Prior to GC and GC/MS Analyses: A Comparative Approach. J. Essent. Oil-Bear. Plants 2013, 16, 613–623. [Google Scholar] [CrossRef]
  59. Darriet, F.; Bendahou, M.; Desjobert, J.M.; Costa, J.; Muselli, A. Bicyclo[4.4.0]decane Oxygenated Sesquiterpenes from Eryngium maritimum Essential Oil. Planta Med. 2012, 78, 386–389. [Google Scholar] [CrossRef]
  60. Thiem, B.; Kikowska, M.; Kurowska, A.; Kalemba, D. Essential Oil Composition of the Different Parts and In Vitro Shoot Culture of Eryngium planum L. Molecules 2011, 16, 7115–7124. [Google Scholar] [CrossRef]
  61. Cavaleiro, C.; Gonçalves, M.J.; Serra, D.; Santoro, G.; Tomi, F.; Bighelli, A.; Salgueiro, L.; Casanova, J. Composition of a volatile extract of Eryngium duriaei subsp. juresianum (M. Laínz) M. Laínz, signalised by the antifungal activity. J. Pharm. Biomed. Anal. 2011, 54, 619–622. [Google Scholar] [CrossRef]
  62. Hashemabadi, D.; Kaviani, B. Chemical Constituents of Essential Oils Extracted from the Leaves and Stems of Eryngium caucasicum Trautv. from Iran. J. Essent. Oil-Bear. Plants 2011, 14, 693–698. [Google Scholar] [CrossRef]
  63. Hashemabadi, D.; Kaviani, B.; Erfatpour, M.; Larijani, K. Comparison of essential oils compositions of eryngo (Eryngium caucasicum Trautv.) at different growth phases by hydrodistillation method. Plant Omics 2010, 3, 135–139. [Google Scholar]
  64. Banout, J.; Havlik, J.; Kulik, M.; Kloucek, P.; Lojka, B.; Valterova, I. Effect of Solar Drying on The Composition of Essential Oil of Sacha Culantro (Eryngium Foetidum L.) Grown in The Peruvian Amazon. J. Food Process. Eng. 2010, 33, 83–103. [Google Scholar] [CrossRef]
  65. Palá-Paúl, J.; Usano-Alemany, J.; Brophy, J.J.; Pérez-Alonso, M.J.; Soria, A.C. Essential oil composition of the different parts of Eryngium aquifolium from Spain. Nat. Prod. Commun. 2010, 5, 817–821. [Google Scholar] [CrossRef] [PubMed]
  66. Majid, S.; Katayoun, M.S. Effect of the Essential Oil of Eryngium caeruleum on Percutaneous Absorption of Piroxicam through Rat Skin. J. Essent. Oil-Bear. Plants 2008, 11, 485–495. [Google Scholar] [CrossRef]
  67. Flamini, G.; Tebano, M.; Cioni, P.L. Composition of the essential oils from leafy parts of the shoots, flowers and fruits of Eryngium amethystinum from Amiata Mount (Tuscany, Italy). Food Chem. 2008, 107, 671–674. [Google Scholar] [CrossRef]
  68. Thi, N.D.T.; Anh, T.H.; Thach, L.N. The Essential Oil Composition of Eryngium foetidum L. in South Vietnam Extracted by Hydro distillation under Conventional Heating and Microwave Irradiation. J. Essent. Oil-Bear. Plants 2008, 11, 154–161. [Google Scholar] [CrossRef]
  69. Palá-Paúl, J.; Usano, J.; Soria, A.C.; Pérez-Alonso, M.J.; Brophy, J.J. Essential oil composition of Eryngium campestre L. growing in different soild types. A preliminary study. Nat. Prod. Commun. 2008, 3, 1121–1126. [Google Scholar] [CrossRef]
  70. Palá-Paúl, J.; Copeland, L.M.; Brophy, J.J.; Goldsack, R.J. Analysis by Gas Chromatography-Mass Spectrometry of the essential oil composition of Eryngium paludosum (Moore & Betche) P.W. Michael: An endemic species from eastern Australia. J. Essent. Oil Res. 2008, 20, 416–419. [Google Scholar] [CrossRef]
  71. Capetanos, C.; Saroglour, V.; Marinz, P.; Simic, A.; Skaltsa, H.D. Essential oil analysis of two endemic Eryngium species from Serbia. J. Serb. Chem. Soc. 2007, 72, 961–965. [Google Scholar] [CrossRef]
  72. Palá-Paúl, J.; Brophy, J.J.; Pérez-Alonso, M.J.; Usano, J.; Soria, A.C. Essential oil composition of the different parts of Eryngium corniculatum Lam. (Apiaceae) from Spain. J. Chromatogr. A 2007, 1175, 289–293. [Google Scholar] [CrossRef]
  73. Palá-Paúl, J.; Pérez-Alonso, M.J.; Velasco-Negueruela, A.; Varadé, J.; Villa, A.M.; Sanz, J.; Brophy, J.J. Essential oil composition of the different parts of Eryngium bourgatii Gouan from Spain. J. Chromatogr. A 2005, 1074, 235–239. [Google Scholar] [CrossRef] [PubMed]
  74. Palá-Paúl, J.; Pérez-Alonso, M.J.; Velasco-Negueruela, A.; Varadé, J.; Villa, M.A.; Sanz, J.; Brophy, J.J. Analysis of the essential oil composition of the different parts of Eryngium glaciale Boiss. from Spain. J. Chromatogr. A 2005, 1094, 179–182. [Google Scholar] [CrossRef] [PubMed]
  75. Sefidkon, F.; Dabiri, M.; Alamshahi, A. Chemical composition of the essential oil of Eryngium billardieri F. Delaroche from Iran. J. Essent. Oil Res. 2004, 16, 42–43. [Google Scholar] [CrossRef]
  76. Brophy, J.J.; Goldsack, R.J.; Copeland, L.M.; Palá-Paúl, J. Essential oil of Eryngium L. species from New South Wales (Australia). J. Essent. Oil Res. 2003, 15, 392–397. [Google Scholar] [CrossRef]
  77. Palá-Paúl, J.; Brophy, J.J.; Goldsack, R.J.; Copeland, L.M.; Pérez-Alonso, M.J.; Velasco-Negueruela, A. Essential oil composition of the seasonal heterophyllous leaves of Eryngium vesiculosum from Australia. Aust. J. Bot. 2003, 51, 497–501. [Google Scholar] [CrossRef]
  78. Martins, A.P.; Salgueiro, L.R.; Proença da Cunha, A.; Vila, R.; Cañigueral, S.; Tomi, F.; Casanova, J. Essential oil composition of Eryngium foetidum from S. Tomé e Príncipe. J. Essent. Oil Res. 2003, 15, 93–95. [Google Scholar] [CrossRef]
  79. Ayoub, N.A.; Nawwar, M.A.M.; Kubeczka, K.H. An unique n-propyl sesquiterpene from Eryngium creticum L. (Apiaceae). Pharmazie 2003, 58, 674–676. [Google Scholar] [CrossRef]
  80. Cobos, M.I.; Rodríguez, J.L.; de Petre, A.; Spahn, E.; Casemeiro, J.; López, A.G.; Zygadlo, J.A. Composition of the essential oil of Eryngium paniculatum Cav. J. Essent. Oil Res. 2002, 14, 82–83. [Google Scholar] [CrossRef]
  81. Kubeczka, K.H.; Ayoulo, N.; Grande, M.; Torres, P. Composition of the essential oils from different parts of Eryngium maritimum L. (Apiaceae). In Proceedings of the Poster at the 29th International Symposium on Essential Oils, Frankfurt, Germany, 6–9 September 1998. [Google Scholar]
  82. Pino, J.A.; Rosado, A.; Fuentes, V. Chemical composition of the seed oil of Eryngium foetidum L. from Cuba. J. Essent. Oil Res. 1997, 9, 123–124. [Google Scholar] [CrossRef]
  83. Pino, J.A.; Rosado, A.; Fuentes, V. Composition of the leaf oil of Eryngium foetidum L. from Cuba. J. Essent. Oil Res. 1997, 9, 467–468. [Google Scholar] [CrossRef]
  84. Wong, K.C.; Feng, M.C.; Sam, T.W.; Tan, G.L. Composition of the leaf and root oils of Eryngium foetidum L. J. Essent. Oil Res. 1994, 6, 369–374. [Google Scholar] [CrossRef]
  85. Leclercq, P.A.; Duñg, N.X.; Lô, V.N.; Toanh, N.V. Composition of the essential oil of Eryngium foetidum L. from Vietnam. J. Essent. Oil Res. 1992, 4, 423–424. [Google Scholar] [CrossRef]
  86. Simon, O.R.; Singh, N. Demonstration of anticonvulsant properties of an aqueous extract of Spirit Weed (Eryngium foetidum L.). West Indian Med. J. 1986, 35, 121–125. [Google Scholar] [PubMed]
  87. Demirpolat, A.; Dogan, G.; Bagci, E. Chemical composition of Essential Oils of Four Scandix Species from Different Parts: A Chemotaxonomic Approach. J. Essent. Oil-Bear. Plants 2018, 21, 1660–1668. [Google Scholar] [CrossRef]
  88. Padalia, R.C.; Verma, R.S.; Chauhan, A.; Tiwari, A.; Joshi, N. Variability in essential oil composition of different plant parts of Heracleum candicans Wall. Ex DC from North India. J. Essent. Oil Res. 2018, 30, 293–301. [Google Scholar] [CrossRef]
  89. Wu, Y.; Xu, Z.; Li, H.; Meng, X.; Bao, Y.; Li, Y.X. Components of Essential Oils in Different Parts of Daucus carota L. var. sativa Hoffm1. Chem. Res. Chin. Univ. 2006, 22, 328–334. [Google Scholar] [CrossRef]
  90. Bettaieb, I.; Bourgou, S.; Wannes, W.A.; Hamrouni, I.; Limam, F.; Marzouk, B. Essential oils, phenolics, and antioxidant activities of different parts of cumin (Cuminum cyminum L.). J. Agric. Food Chem. 2010, 58, 10410–10418. [Google Scholar] [CrossRef]
  91. Saraccedil, H.T.; Akin, M.; Demirci, B.; Başer, K.H.C. Chemical composition and antibacterial activity of essential oils from different parts of some Bupleurum L. species. Afr. J. Microbiol. Res. 2012, 6, 2899–2908. [Google Scholar] [CrossRef]
  92. Akιn, M.; Taner Saraçoğlu, H.; Demirci, B.; Başer, K.H.C.; Küçüködük, M. Chemical composition and antibacterial activity of essential oils from different parts of Bupleurum rotundifolium L. Rec. Nat. Prod. 2012, 6, 316–320. [Google Scholar]
  93. Marcetić, M.; Bozić, D.; Milenković, M.; Lakusić, B.; Kovacević, N. Chemical composition and antimicrobial activity of essential oil of different parts of Seseli rigidum. Nat Prod. Commun. 2012, 7, 1091–1094. [Google Scholar] [CrossRef] [PubMed]
  94. Kovacevic, N.N.; Marcetic, M.D.; Lakusic, D.V.; Lakusic, B.S. Composition of the Essential Oils of Different Parts of Seseli annuum L. (Apiaceae). J. Essent. Oil-Bear. Plants 2016, 19, 671–677. [Google Scholar] [CrossRef]
  95. Maggi, F.; Papa, F.; Dall’Acqua, S.; Nicoletti, M. Chemical analysis of essential oils from different parts of Ferula communis L. growing in central Italy. Nat. Prod. Res. 2016, 30, 806–813. [Google Scholar] [CrossRef]
  96. Rahali, F.; Lamine, M.; Rebey, I.; Aidi Wannes, W.; Hammami, M.; Selmi, S.; Mliki, A.; Sellami, I. Biochemical characterization of fennel (Ferula communis L.) different parts through their essential oils, fatty acids and phenolics. Acta Sci. Pol.-Hortorum Cultus 2021, 20, 3–14. [Google Scholar] [CrossRef]
  97. Dosoky, N.S.; Kirpotina, L.N.; Schepetkin, I.A.; Khlebnikov, A.I.; Lisonbee, B.L.; Black, J.L.; Woolf, H.; Thurgood, T.L.; Graf, B.L.; Satyal, P.; et al. Volatile Composition, Antimicrobial Activity, and In Vitro Innate Immunomodulatory Activity of Echinacea purpurea (L.) Moench Essential Oils. Molecules 2023, 28, 7330. [Google Scholar] [CrossRef] [PubMed]
  98. Beltrán, S.B.; Sierra, L.J.; Fernández-Alonso, J.L.; Romero, A.K.; Martínez, J.R.; Stashenko, E.E. Antioxidant Properties and Secondary Metabolites Profile of Hyptis colombiana at Various Phenological Stages. Molecules 2023, 28, 6767. [Google Scholar] [CrossRef] [PubMed]
  99. Rungqu, P.; Oyedeji, O.; Gondwe, M.; Oyedeji, A. Chemical Composition, Analgesic and Anti-Inflammatory Activity of Pelargonium peltatum Essential Oils from Eastern Cape, South Africa. Molecules 2023, 28, 5294. [Google Scholar] [CrossRef]
  100. Pérez Zamora, C.M.; Torres, C.A.; Nuñez, M.B. Antimicrobial Activity and Chemical Composition of Essential Oils from Verbenaceae Species Growing in South America. Molecules 2018, 23, 544. [Google Scholar] [CrossRef]
  101. Real Farmacopea Española, 3rd ed.; Ministerio de Sanidad y Consumo: Madrid, Spain, 2005.
  102. Adams, R.P. Identification of Essential Oils Components by Gas Chromatography/Mass Spectroscopy, 2nd ed.; Allured Publishing Corporation: Carol Stream, IL, USA, 1995. [Google Scholar]
  103. Adams, R.P. Identification of Essential Oils Components by Gas Chromatography/Quadrupole Mass Spectroscopy, 3rd ed.; Allured Publishing Corporation: Carol Stream, IL, USA, 2001. [Google Scholar]
  104. Adams, R.P. Identification of Essential Oil Components by Gas Chromatography—Mass Spectrometry, 4th ed.; Allured Publishing Corporation: Carol Stream, IL, USA, 2007. [Google Scholar]
  105. Stenhagen, E.; Abrahamsson, S.; McLafferty, F.W. Registry of Mass Spectral Data; Wiley: New York, NY, USA, 1974. [Google Scholar]
  106. Heller, S.R.; Milne, G.W.A. EPA/NIH Mass Spectral Data Base; US Government Printing Office: Washington, DC, USA, 1978.
  107. Swigar, A.A.; Silverstein, R.M. Monoterpenes; Aldrich: Milwaukee, WI, USA, 1981. [Google Scholar]
  108. Joulain, D.; König, W.A. The Atlas of Spectral Data of Sesquiterpene Hydrocarbons; E. B.-Verlag: Hamburg, Germany, 1998. [Google Scholar]
Molecules 29 00562 g001
Figure 1. Distribution of Eryngium dilatatum Lam. in the Iberian Peninsula.
Figure 1. Distribution of Eryngium dilatatum Lam. in the Iberian Peninsula.
Molecules 29 00562 g001
Table 2. Oil yield of the different parts of Eryngium dilatatum Lam. from Spain.
Table 2. Oil yield of the different parts of Eryngium dilatatum Lam. from Spain.
SampleVoucher DetailsYield (%)
E.d.IMACB-73213. Road from Grazalema to Zahara (Km 1), Cádiz province (Spain). All the specimens were gathered during the summer season in flowering period. 15-VII-1999. 30STF7871.0.29
E.d.SL0.33
E.d.R0.14
Yield based on dry weight. E.d. = Eryngium dilatatum; I = inflorescences; SL = stems and leaves; R = roots.
Table 4. Distribution of terpenoid compounds in the different fractions of Eryngium dilatatum Lam. from Spain.
Table 4. Distribution of terpenoid compounds in the different fractions of Eryngium dilatatum Lam. from Spain.
Terpenoid/SampleE.d.IE.d.SLE.d.R
Monoterpene hydrocarbons4.43.53.1
Oxygenated monoterpenes1.32.40.5
Sesquiterpene hydrocarbons61.858.427.4
Oxygenated sesquiterpenes29.823.245.2
Total97.387.576.2
E.d. = Eryngium dilatatum; I = inflorescences; SL = stems and leaves; R = roots.
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Palá-Paúl, J.; Pérez-Alonso, M.J.; Soria, A.C.; Brophy, J.J. Chemical Composition of the Essential Oils of the Iberian Peninsula Endemic Species Eryngium dilatatum Lam. Molecules 2024, 29, 562. https://doi.org/10.3390/molecules29030562

AMA Style

Palá-Paúl J, Pérez-Alonso MJ, Soria AC, Brophy JJ. Chemical Composition of the Essential Oils of the Iberian Peninsula Endemic Species Eryngium dilatatum Lam. Molecules. 2024; 29(3):562. https://doi.org/10.3390/molecules29030562

Chicago/Turabian Style

Palá-Paúl, Jesús, María José Pérez-Alonso, Ana C. Soria, and Joseph J. Brophy. 2024. "Chemical Composition of the Essential Oils of the Iberian Peninsula Endemic Species Eryngium dilatatum Lam." Molecules 29, no. 3: 562. https://doi.org/10.3390/molecules29030562

APA Style

Palá-Paúl, J., Pérez-Alonso, M. J., Soria, A. C., & Brophy, J. J. (2024). Chemical Composition of the Essential Oils of the Iberian Peninsula Endemic Species Eryngium dilatatum Lam. Molecules, 29(3), 562. https://doi.org/10.3390/molecules29030562

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