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Article

Chemical Characterization of the Essential Oil Compositions of Mentha spicata and M. longifolia ssp. cyprica from the Mediterranean Basin and Multivariate Statistical Analyses

by
Hasan İsfendiyaroğlu
1,*,
Azmi Hanoğlu
2,
Duygu Yiğit Hanoğlu
3,
Fehmi B. Alkaş
4,
Kemal Hüsnü Can Başer
2 and
Dudu Özkum Yavuz
3
1
Department of Phytotherapy, Faculty of Pharmacy, Near East University, Nicosia 99138, Cyprus
2
Department of Pharmacognosy, Faculty of Pharmacy, Near East University, Nicosia 99138, Cyprus
3
Department of Pharmaceutical Botany, Faculty of Pharmacy, Near East University, Nicosia 99138, Cyprus
4
Department of Toxicology, Faculty of Pharmacy, Near East University, Nicosia 99138, Cyprus
*
Author to whom correspondence should be addressed.
Molecules 2024, 29(9), 1970; https://doi.org/10.3390/molecules29091970
Submission received: 5 April 2024 / Revised: 22 April 2024 / Accepted: 23 April 2024 / Published: 25 April 2024
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Abstract

:
This present study aims to characterize the essential oil compositions of the aerial parts of M. spicata L. and endemic M. longifolia ssp. cyprica (Heinr. Braun) Harley by using GC-FID and GC/MS analyses simultaneously. In addition, it aims to perform multivariate statistical analysis by comparing with the existing literature, emphasizing the literature published within the last two decades, conducted on both species growing within the Mediterranean Basin. The major essential oil components of M. spicata were determined as carvone (67.8%) and limonene (10.6%), while the major compounds of M. longifolia ssp. cyprica essential oil were pulegone (64.8%) and 1,8-cineole (10.0%). As a result of statistical analysis, three clades were determined for M. spicata: a carvone-rich chemotype, a carvone/trans-carveol chemotype, and a pulegone/menthone chemotype, with the present study result belonging to the carvone-rich chemotype. Carvone was a primary determinant of chemotype, along with menthone, pulegone, and trans-carveol. In M. longifolia, the primary determinants of chemotype were identified as pulegone and menthone, with three chemotype clades being pulegone-rich, combined menthone/pulegone, and combined menthone/pulegone with caryophyllene enrichment. The primary determinants of chemotype were menthone, pulegone, and caryophyllene. The present study result belongs to pulegone-rich chemotype.

Graphical Abstract

1. Introduction

Lamiaceae, the sixth largest family among the angiosperms consisting of 236 genera with over 7000 species, is composed of conventionally used medicinal plants [1]. Lamioideae and Nepetoideae are two of the most prevalent subfamilies among the total of 11 subfamilies of the Lamiaceae family [2]. The genus Mentha L., belonging to the Nepetoideae subfamily, consists of 24 accepted species worldwide [3,4]. Mentha spp., well known as “mint”, is reported to have anti-inflammatory, sedative, antioxidant, antibacterial, and antifungal effects along with several traditional uses [5]. One of the popular plants in this genus is M. spicata L., which is used worldwide for medicinal and culinary purposes [6]. In Cyprus, the family Lamiaceae is represented by 32 genera, and the genus Mentha is represented by four species; M. aquatica L., M. pulegium L., M. spicata L., and M. longifolia (L.) Huds [7,8].
The essential oil components of M. spicata have been extensively reviewed [6,9,10]. The essential oil composition studies have shown a variety of the major compounds in oils of M. spicata collected from the Mediterranean region [11,12,13,14,15,16,17,18,19,20]. Previously, M. spicata ssp. spicata oils from Turkey have been reported as rich in menthone/isomenthone, trans-sabinene hydrate/carvone/terpinen-4-ol, and 1,8-cineole/linalool/carvone, respectively. It was also summarized in the same article that the chemotypes of M. spicata growing in the Mediterranean basin until that day were piperitone oxide-rich, piperitenone oxide-rich, carvone and/or dihydrocarvone-rich, dihydrocarveol-rich, linalool-rich, and pulegone/menthone/isomenthone-rich oils [11]. There is only one report on the essential oil composition of M. spicata from Cyprus. The main compounds reported are carvone (71.3%) and limonene (12.5%) [12]. However, there exists a general lack of comprehensive chemotaxonomic studies using the existing literature, with previous reviews reporting the essential oil compositions of their sampling volume, but no classifications were made between the samples apart from the original classifications made by the source literature utilized in each review study [6,9,10].
The essential oil compositions of M. longifolia were also previously reported, revealing that in the reported literature, there exists discrepancies and variations in the reported major components of essential oils. Among those reported as major compounds of M. longifolia essential oil are mainly pulegone, 1,8-cineole, menthone, menthol, carvone, limonene, piperitone, piperitenone oxide [16,21,22,23,24,25,26,27]. Chemotaxonomic research on this species is not forthcoming, with there existing only three studies with relatively large sample numbers in the previous literature, with none subjecting the samples to extensive analyses to solidify chemotaxonomic classification onto a statistical foundation [11,28,29]. This is exacerbated by the fact that M. longifolia appears to exhibit heterogeneous essential oil composition, with significant numbers of chemotypes being identified in each previous study. However, these chemotype identifications rely on personal observational deductions from the raw data of the researchers, and, as such, they are highly subjective. An objective, statistical method is more reliable for high-fidelity, high-accuracy determination of chemotypes than any subjective measure. A recent review has concatenated and summarized these chemotypes, stressing the lack of phytochemical studies on the essential oil composition of M. longifolia [30]. There is only one report on the essential oil composition of M. longifolia ssp. cyprica with pulegone (71.5%), 1,8-cineole (9.5%), menthone (5.0%), and limonene (3.4%) as major components [26].
There exists a large number of subspecies and variations in the essential oil composition among Mentha species in the Mediterranean Basin. Therefore, it is reasonable to think that there exist distinct chemotypes that can be identified with large-scale data processing, by employing statistical methods. This present study aims to characterize the essential oil composition of the aerial parts of M. spicata and M. longifolia ssp. cyprica, and to perform multivariate statistical analysis, principal component (PCA) and hierarchical cluster analyses (HCA), by comparing with the existing literature, emphasizing the literature published within the last two decades, conducted on both species growing within the Mediterranean Basin. Due to the endemic nature of M. longifolia ssp. cyprica, it was compared with M. longifolia. This study, therefore, uses statistical methods, for the first time as far as the authors know, to identify and establish chemotypes at a higher precision in the Mediterranean Basin.

2. Results and Discussion

The essential oils of M. spicata and M. longifolia ssp. cyprica were isolated by hydrodistillation and analyzed for chemical characterization using simultaneous GC-FID and GC/MS. The yields of the essential oils were calculated on a dry weight basis as 4.0% and 3.0%, respectively. Overall, 32 and 22 identified compounds were detected, comprising the total of essential oils. The major compounds of M. spicata were determined as carvone (67.8%) and limonene (10.6%), while M. longifolia ssp. cyprica contained pulegone (64.8%), and 1,8-cineole (10.0%), respectively. Table 1 shows the detailed essential oil compositions of the aerial parts of M. spicata and the endemic M. longifolia ssp. cyprica from Northern Cyprus.
The HCA results of the essential oils analyses from the present study and related studies of Mentha spicata from within the Mediterranean region are given in Figure 1. The results indicate the presence of three major clades (given as red squares A–C). A linalool-rich chemotype (ranging between 86.7% and 93.9%) from Greece was composed of the same population sampled at different times [17]. Another outlier is also from Greece, with an unusual piperitone epoxide and piperitenone oxide (23.0% and 41.0% of total essential oil, respectively) dominant chemotype [34]. The single sample comprising another outlier was a cis-carvone oxide (44.1%) chemotype, with dihydrocarvone also present at 8.9% [15].
The three major clades are A–C, with A and C being closer in chemical makeup to each other than B. A and C are both carvone-bearing chemotypes, with the former containing it at an average of 60.3% and the latter at 20.8%. Clade A, which was populated with the highest number of samples, was composed of a total of 36 samples [12,13,14,15,19,34,36,37,38,39,40,43,44,45,46,47,48,49,50,51,52,53,54,55,56,57]. Clade B was composed of a total of 4 samples [13,14,42] and clade C was composed of a total of 10 samples [14,20,35,41]. Clades A and C differ from each other in not only carvone, but other constituents as well, primarily with trans-carveol, which is present in significantly higher concentrations in C at approximately 37.0% than it is in A, at 11.2%. Therefore, the two clades are differentiated from each other by reduced carvone and increased trans-carveol in C compared to A. Clade B is a combined menthone/pulegone/menthol chemotype, with average composition of 23.6% menthone and 19.6% pulegone, along with 7.16% menthol.
The M. spicata essential oil sample obtained from the present study was placed in Clade A, indicating that it belongs to the carvone-rich chemotype dominated by this compound. The other study from Cyprus that also characterized M. spicata essential oil [17] was placed into the same clade, with low Euclidean distancing, indicating that they belong to the same chemotype and are of similar composition to the present study.
The three major clades (A, B, and C) were also subjected to ANOVA to determine statistically significant differences in essential oil content. Isolated samples were not considered for ANOVA due to limited sample sizes. The distinguishing feature of the three clades was found to be the carvone content, with clade A having the greatest concentration, followed by C, and the least carvone being present in B (p < 0.001). Therefore, carvone concentration in essential oil can be considered to be a major determinant in the distinction of these clades from each other. It was determined that 1,8-cineole and limonene contents were not significantly different among the three groups (p > 0.05) and, therefore, are not significant determinants of chemotype among these three clades.
Pulegone, cis-isopulegone, menthol, and menthone content of the essential oil were both determined to be a statistically significant determinant of chemotype, with A and C being similar to each other (p > 0.05), but B being significantly different from either (p < 0.001). All of these phytochemicals were present in higher concentrations in essential oils obtained from samples in B, compared to those in A or C.
A statistically significant increase was observed in the concentration of the essential oil of 2-hydroxy-3-(3-methyl-2-butenyl)-3-cyclopenten-1-one in C compared to A (p < 0.001) at an average concentration of 7.2% in C compared to an average of 0.1% in A, providing another differentiating characteristic between the two clades [14]. However, the identification of this compound was determined to be irrelevant since it was not reported from any natural source in M. spicata in the previous literature.
In light of these statistical analyses, as explained above, it can be suggested that three definitive and four isolated samples can be associated with M. spicata. The isolated samples are putative chemotypes due to the presence of a single sample in each category; therefore, no definitive assertions can be made concerning their chemotypic uniqueness. However, much more definitive deductions can be made about clades A–C, which, according to the PCA, HCA, and ANOVA discussed herein, can be divided into three chemotypes: a carvone-rich chemotype with a simple majority of carvone associated with clade A, a carvone-poor chemotype that also features enrichment in menthol, menthone, pulegone, and cis-isopulegone, associated with clade B, and a carvone-rich chemotype that is not as rich in carvone as clade A but containing higher concentrations of trans-carveol (Table 2).
The results indicate that among the M. spicata essential oil samples obtained from references, as well as the current study, there exists a significant variation in the essential oil composition, with certain possible clusterings (Figure 2). Among these, linalool, carvone, pulegone, and menthone appear to be significant components contributing to essential oil variation, with some others, such as limonene and 1,8-cineole, contributing to a lesser degree (Table 2).
The samples within M. longifolia were divided into three definitive clades and two putative clades, made of single members. The putative clades were disregarded for further statistical analyses. The definitive clades were named X, Y, and Z (Figure 3). Clade X was composed of a total of seven samples [21,22,25,27]. Clade Y was composed of a total of four samples [28]. Clade Z was composed of a total of three samples [24,26,27].
Clade X corresponds to a pulegone-rich clade with strong enrichment in pulegone (56.9% averaged), and low menthone content at approximately 6.3%. The current study sample is in clade X, with 64.8% pulegone and 7.6% menthone content. Clade Y corresponds to a menthone/pulegone chemotype that displays reduced pulegone (14.4% on average) but also displays enrichment in menthone (25.2% on average). Clade Z is characterized by a combined menthone/pulegone chemotype (12.6% and 18.3%, respectively) and slight caryophyllene enrichment (2.8% on average) (Table 3).
ANOVA revealed that menthone was a major determinant of chemotype, with clades X and Z on one hand and Y on the other, being significantly different in menthone concentrations of their essential oils (p < 0.05). X and Z did not have a significant difference in menthone concentration (p > 0.05). On the other hand, clade X was differentiated from Y and Z with a significant difference in pulegone concentration (p < 0.05), whereas Y and Z did not have a significant difference in pulegone content. Finally, there existed a statistically significant difference in the caryophyllene concentration in clade Z compared to clades X and Y (p < 0.05). Clades X and Y did not have significantly different caryophyllene content (p > 0.05). These findings were corroborated by the PCA conducted on M. longifolia, which indicated menthone, pulegone, and caryophyllene as significant contributors to variation among samples. Terpinen-4-ol and piperitone oxide could not be determined, due to inability to establish homogeneity of variances as a prerequisite for ANOVA (Table 3, Figure 4).
The present study results demonstrate the utility of multivariate statistical analysis of essential oil for the determination of chemotypic taxonomy. These novel methods, with their higher discretionary power, allow for more reliable classification of samples into existing chemotypes. Such applications are important when, for example, cultivating plants for medicinal or industrial purposes, so that the essential oil composition, and therefore the utility of plants from a medicinal or industrial standpoint, can be more definitively ascertained, increasing safety for the former, and yield, and efficiency for the latter. As an example, a recent study, also utilizing the principles of HCA and PCA to compare their samples, discovered previously undescribed chemotypes of Mentha sp. [58].
The statistical determination of chemotype Is also highly important in chemotaxonomy from a purely scientific perspective. In the present study, the present sample was chemotaxonomically classified purely on the basis of the HCA classification. While such a result could also be obtained from a subjective determination of the chemotype, there may always be confounding factors that a scientist may ignore or miss. For example, the M. longifolia analysis in this study indicated that the slight enrichment in caryophyllene is a determining factor in clade Z, despite the caryophyllene concentration not exceeding 3%. It, thus, demonstrates that different compounds can be strong determinants of chemotype even in small concentration differences, which may not necessarily be all that obvious to a subjective determination by a human. This chemotaxonomy determination based on statistical differences, regardless of the concentration scale in question, opens a new dimensionality to chemotype determination, and allows for the distinction between chemotypes that are superficially similar in the composition of the major substances, but may exhibit subtle differences in their composition, therefore comprising two different, albeit closely related, chemotypes.
These differences in composition are especially important in the medicinal and industrial cultivation of such plants, where the toxicological profile, which depends on not only the concentration, but also the specific toxicity of the compounds in question, chemotypic differences between a chemotype that does not contain any toxic compounds above threshold limits, and a chemotype that has a slightly higher concentration of a highly toxic compound, becomes crucial from a safety perspective, thus requiring the distinction of chemotypes based on chemical composition.

3. Materials and Methods

3.1. Plant Material

The collected plant materials were identified by K.H.C. Başer and D. Özkum Yavuz, according to the Flora of Cyprus [13]. Aerial parts of the cultivated M. spicata (Flowering period: July–November), and natural M. longifolia ssp. cyprica (flowering period: June–November) were collected from Cengizköy-Lefka/Northern Cyprus on 1 July 2022 during the flowering stage. They were separately air-dried in the shade. Voucher specimens are kept at the Herbarium of the Near East University, Turkish Republic of Northern Cyprus (NEUN) with the voucher numbers NEUN 20001 and 20002.

3.2. Isolation of Essential Oils

One hundred grams of air-dried samples were separately distilled for 3 h using a Clevenger-type apparatus by hydrodistillation. The resulting essential oil was stored at 4 °C until further analyses. The oil yields were calculated as v/w on a dry weight basis.

3.3. Selection of Mentha spicata and M. longifolia Essential Oils for Multivariate Analyses

The samples for comparison were selected from previous research conducted on Mentha spicata and M. longifolia within the Mediterranean Basin. All samples were restricted to the Mediterranean Basin to prevent inevitable divergence in plant physiology due to divergent edaphic and environmental factors. Previous research was also limited to approximately the last 20 years so that differences in available technological tools and research methodologies could be minimized. Studies that indicated raw percentile values were taken into account, with those that gave mean ± SD also excluded from analysis.

3.4. GC-FID Analysis

The GC/MS analysis was carried out with an Agilent 5977B GC-MSD system (Santa Clara, CA, USA). Innowax FSC column (Agilent, 60 m × 0.25 mm, 0.25 mm film thickness) was used with helium as carrier gas (0.8 mL/min). GC oven temperature was kept at 60 °C for 10 min and programmed to 220 °C at a rate of 4 °C/min, and kept constant at 220 °C for 10 min and then programmed to 240 °C at a rate of 1 °C/min. Split ratio was adjusted at 40:1. The injector temperature was set at 250 °C. Mass spectra were recorded at 70 eV. Mass range was from m/z 35 to 450. FID results were used to report the characterized compounds’ relative percentages (%) [59].

3.5. GC/MS Analysis

The analysis was carried out using an Agilent 7890B GC system. The integrated FID detector temperature was 300 °C. To obtain the same elution order with GC/MS, simultaneous auto-injection was performed on a duplicate of the same column applying the same operational conditions. Relative percentage amounts of the separated compounds were calculated from FID chromatograms. Identification of the essential oil components was carried out by comparison of their relative retention times (RRT) with those of authentic samples or by comparison of their linear retention index (LRI) to a series of n-alkanes. Computer matching against commercial (Wiley GC/MS Library, NIST Library) and in-house “Başer Library of Essential Oil Constituents” built up by genuine compounds and components of known oils, as well as MS literature data, was used for the identification [59].

3.6. Statistical Analysis

All relevant data were imported to IBM SPSS Statistics v27.0 (International Business Machines (IBM) Corporation, Armonk, NY, USA). Principal component analysis (PCA) was performed using the correlation matrix method with sequential eigenvalues selected based on the introduction of “kinks” in the scree plot. The varimax rotation method was employed to improve the correlation between chemical constituents and principal components. Correlation matrices were employed to ascertain the effect of different constituents on chemotypes. Hierarchical cluster analysis (HCA) was performed using the squared Euclidean distance between-groups linkage method using agglomeration schedules. The dendrograms were produced from the HCA using this data. Only components that were deemed major by the authors of at least one of the references cited herein were included in the PCA and HCA. Previous studies from the Mediterranean Basin were included in the present study as references, with those outside of the Mediterranean Basin excluded from the study. The clades as determined by HCA were subjected to one-way analysis of variance (ANOVA) to confirm chemotypic differences, with Levene’s test employed to test for homogeneity of variances, and Bonferroni’s post hoc test was utilized to ascertain differences between identified clades.

4. Conclusions

The essential oil composition of M. spicata growing in Northern Cyprus revealed that the major components were carvone (67.8%) and limonene (10.6%), while the major compounds of M. longifolia ssp. cyprica essential oil were pulegone (64.8%) and 1,8-cineole (10.0%), respectively. The multivariate analysis showed the existence of three major clades within the M. spicata growing in Mediterranean region, with a carvone-rich chemotype, a carvone/trans-carveol chemotype, and a pulegone/menthone chemotype, with the present study belonging to the carvone-rich chemotype. It was determined that carvone was a primary determinant of chemotype, along with menthone, pulegone, and trans-carveol. It was also determined that 1,8-cineole was not an important determinant of chemotype.
In M. longifolia growing in Mediterranean region, it was determined that the primary determinants of chemotype were pulegone and menthone, with three chemotypes being identified as pulegone-rich, combined menthone/pulegone, and combined menthone/pulegone with caryophyllene enrichment. The Cyprus endemic, M. longifolia ssp. Cyprica, sample analyzed in the current study is in the pulegone-rich clade.
HCA, PCA, and ANOVA all demonstrate that the Mentha species within the Mediterranean Basin display remarkable biodiversity. To the extent of the authors’ knowledge, this study is the first of its kind to establish the biodiversity of Mentha species in the Mediterranean Basin at a statistical level; therefore, the present study has pioneering value. This is especially true in consideration of the fact that Mentha species display remarkable diversity in essential oil composition even when the edaphic factors are highly convergent, in stable climatic conditions such as that within the Mediterranean Basin, displaying that Mentha is a remarkably biodiverse genus.

Author Contributions

Writing—original draft, H.İ., A.H., D.Y.H. and F.B.A.; writing—review and editing, K.H.C.B. and D.Ö.Y. 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

The data used to support the findings of this study are included within the article. For further data, they are available from the corresponding author upon request.

Conflicts of Interest

The authors declare no conflicts of interest.

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Molecules 29 01970 g001
Figure 1. Hierarchical cluster analysis (HCA) of essential oil compositions of M. spicata from the Mediterranean Basin. A, B, and C refer to the clades identified by HCA (PS: present study, RX.Y refers to X: reference used, Y: sample within reference), references: R1 [15], R2 [35], R3 [36], R4 [20], R5 [16], R6 [17], R7 [34], R8 [37], R9 [38], R10 [13], R11 [39], R12 [40], R13 [41], R14 [42], R15 [43], R16 [44], R17 [45], R18 [46], R19 [47], R20 [20], R21 [48], R22 [49], R23 [50], R24 [51], R25 [52], R26 [53], R27 [54], R28 [55], R29 [56], R30 [12], R31 [57], R32 [19], R33 [14].
Figure 1. Hierarchical cluster analysis (HCA) of essential oil compositions of M. spicata from the Mediterranean Basin. A, B, and C refer to the clades identified by HCA (PS: present study, RX.Y refers to X: reference used, Y: sample within reference), references: R1 [15], R2 [35], R3 [36], R4 [20], R5 [16], R6 [17], R7 [34], R8 [37], R9 [38], R10 [13], R11 [39], R12 [40], R13 [41], R14 [42], R15 [43], R16 [44], R17 [45], R18 [46], R19 [47], R20 [20], R21 [48], R22 [49], R23 [50], R24 [51], R25 [52], R26 [53], R27 [54], R28 [55], R29 [56], R30 [12], R31 [57], R32 [19], R33 [14].
Molecules 29 01970 g001
Molecules 29 01970 g002
Figure 2. Principal component 3D graph for Component 1 (PC1), Component 2 (PC2), and Component 3 (PC3) in Mentha spicata. Eucalyptol = 1,8-cineole, Corylone = 2-Hydroxy-3-(3-methyl-2-butenyl)-3-cyclopenten-1-one.
Figure 2. Principal component 3D graph for Component 1 (PC1), Component 2 (PC2), and Component 3 (PC3) in Mentha spicata. Eucalyptol = 1,8-cineole, Corylone = 2-Hydroxy-3-(3-methyl-2-butenyl)-3-cyclopenten-1-one.
Molecules 29 01970 g002
Molecules 29 01970 g003
Figure 3. Hierarchical cluster analysis (HCA) of essential oil compositions of Mentha longifolia from the Mediterranean Basin. X, Y, and Z refer to the clades identified by HCA. (PS: present study, Ra.b refers to a: reference used, b: sample within reference), references: R1 [23], R2 [24], R3 [16], R4 [26], R5 [25], R6 [22], R7 [21], R8 [27].
Figure 3. Hierarchical cluster analysis (HCA) of essential oil compositions of Mentha longifolia from the Mediterranean Basin. X, Y, and Z refer to the clades identified by HCA. (PS: present study, Ra.b refers to a: reference used, b: sample within reference), references: R1 [23], R2 [24], R3 [16], R4 [26], R5 [25], R6 [22], R7 [21], R8 [27].
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Molecules 29 01970 g004
Figure 4. Principal component 3D graph for Component 1 (PC1), Component 2 (PC2), and Component 3 (PC3) in Mentha longifolia.
Figure 4. Principal component 3D graph for Component 1 (PC1), Component 2 (PC2), and Component 3 (PC3) in Mentha longifolia.
Molecules 29 01970 g004
Table 1. The essential oil compositions of the aerial parts of cultivated M. spicata and natural M. longifolia ssp. cyprica from Northern Cyprus.
Table 1. The essential oil compositions of the aerial parts of cultivated M. spicata and natural M. longifolia ssp. cyprica from Northern Cyprus.
KILRICompound NameM. spicataM. longifolia ssp. cyprica
Relative Percentages (%)
1008–1039 b993α-Pinene1.00.9
1012–1039 b997α-Thujene0.1-
10172,5-Diethyltetrahydrofuran0.1-
1085–1130 b1089β-Pinene1.21.7
1098–1140 b1104Sabinene0.61.0
1140–1175 b1143Myrcene0.71.1
1178–1219 b1180Limonene10.63.9
1198–1234 a11931,8-Cineole4.810.0
1211–1251 b1212(Ζ)-β-Ocimene-0.4
1357–1417 a13673-Octanol0.3-
1438–1474 a1444trans-Sabinene hydrate0.5-
1440–1492 a1454Menthone-7.6
1453–1525 a1481Isomenthone-0.3
1495–1546 a1497β-Bourbonene0.8-
1556–1600 a1567β-Elemene0.6-
1583 a1568cis-Isopulegone-0.5
1587–1597 a1577trans-Isopulegone-0.4
1570–1617 a1579β-Caryophyllene0.91.7
1564–1630 b1585Terpinen-4-ol0.4-
1602–1650 b1601trans-Dihydrocarvone1.1-
1631–1665 b1641Pulegone1.164.8
1657–1700 c1651Dihydrocarvyl acetate1.0-
1656–1690 a1660α-Humulene0.60.4
1664–1694 a1662trans-Verbenol-0.1
1646–1741 a1676α-Terpineol-0.8
1677–1731 a1677α-Terpinyl acetate0.2-
1675–1723 a1684Borneol0.3-
1665–1746 a1692Germacrene D0.50.9
1703Neodihydrocarveol0.4-
1699–1769 a1717Bicyclogermacrene0.40.7
1696–1748 a1725Piperitone-0.4
1713–1763 a1734Carvone67.8-
1710–1782 a1751cis-Carvyl acetate0.8-
1800–1836 a1814Calamenene0.6-
1833Carvone-1,2-oxide0.2-
1819–1881 a1845cis-Carveol1.7-
1918–1956 a1928Piperitenone0.21.5
1983–1984 a1958Piperitenone oxide-0.8
2034–2090 a2043Cubenol0.3-
2090–2153 a2110Spathulenol0.10.2
2175–2259 a2216α-Cadinol0.2-
Monoterpene hydrocarbons14.29.0
Oxygenated monoterpenes80.587.2
Sesquiterpene hydrocarbons4.43.7
Oxygenated sesquiterpenes0.60.2
Others0.4-
Total100.0100.0
KI: from literature [31] a, [32] b, [33] c, LRI (linear retention index) calculated against n-alkanes series; % calculated from FID data.
Table 2. The rotated component (loadings) matrix of the essential oil compositions of Mentha spicata in the Mediterranean Basin.
Table 2. The rotated component (loadings) matrix of the essential oil compositions of Mentha spicata in the Mediterranean Basin.
CompoundsComponents
1234
Menthol0.973
Pulegone0.9600.101
Menthone0.6960.622
cis-Isopulegone0.1450.925 −0.151
β-Pinene 0.733 0.104
Eucalyptol (=1,8-Cineole) 0.502
cis-Carvone oxide 0.916
trans-Carveol 0.886
cis-Carveol 0.814
β-Caryophyllene 0.1510.865
Germacrene D0.110 0.773
Linalool 0.623
Dihydrocarvone−0.219 −0.2390.541
p-Cymene
Myrcene−0.136
α-Pinene 0.420 −0.159
Corylone (=2-Hydroxy-3-(3-methyl-2-butenyl)-3-cyclopenten-1-one)−0.117
α-Cadinol0.1560.606 −0.121
Carvone−0.470−0.369 −0.237
Sabinene hydrate−0.140 −0.110
Dihydrocarveol −0.1040.167−0.120
Piperitenone oxide −0.130
Terpinen-4-ol−0.137−0.143
Limonene−0.338 −0.259
Neoiso-Dihydrocarveol acetate−0.156−0.111−0.132−0.127
Table 3. The rotated component (loadings) matrix of the essential oil compositions of Mentha longifolia in the Mediterranean Basin.
Table 3. The rotated component (loadings) matrix of the essential oil compositions of Mentha longifolia in the Mediterranean Basin.
Components
123456
Terpinen-4-ol0.954
Menthol0.944 −0.100 −0.106
Menthone0.8210.359−0.234−0.214−0.151
Piperitone oxide0.735
Pulegone−0.549−0.368−0.533−0.447 −0.134
Dihydrocarvone−0.1680.962 0.102
Piperitone0.2690.945−0.132
Germacrene D0.1690.8510.204 −0.311−0.135
Piperitenone−0.1170.490 0.4600.478−0.244
trans-Piperitone epoxide−0.131 0.968 −0.125
Piperitenone oxide−0.157 0.963−0.101 0.129
Caryophyllene−0.4640.4680.5030.2500.4200.127
Carvone 0.978
Limonene−0.2530.146−0.1670.898−0.214
Isomenthone −0.130 −0.1130.9450.183
Borneol−0.197−0.174−0.152−0.1510.774
cis-Piperitone epoxide 0.263 0.1440.893
Eucalyptol (=1,8-cineole) −0.1060.523−0.309 −0.713
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İsfendiyaroğlu, H.; Hanoğlu, A.; Yiğit Hanoğlu, D.; Alkaş, F.B.; Başer, K.H.C.; Özkum Yavuz, D. Chemical Characterization of the Essential Oil Compositions of Mentha spicata and M. longifolia ssp. cyprica from the Mediterranean Basin and Multivariate Statistical Analyses. Molecules 2024, 29, 1970. https://doi.org/10.3390/molecules29091970

AMA Style

İsfendiyaroğlu H, Hanoğlu A, Yiğit Hanoğlu D, Alkaş FB, Başer KHC, Özkum Yavuz D. Chemical Characterization of the Essential Oil Compositions of Mentha spicata and M. longifolia ssp. cyprica from the Mediterranean Basin and Multivariate Statistical Analyses. Molecules. 2024; 29(9):1970. https://doi.org/10.3390/molecules29091970

Chicago/Turabian Style

İsfendiyaroğlu, Hasan, Azmi Hanoğlu, Duygu Yiğit Hanoğlu, Fehmi B. Alkaş, Kemal Hüsnü Can Başer, and Dudu Özkum Yavuz. 2024. "Chemical Characterization of the Essential Oil Compositions of Mentha spicata and M. longifolia ssp. cyprica from the Mediterranean Basin and Multivariate Statistical Analyses" Molecules 29, no. 9: 1970. https://doi.org/10.3390/molecules29091970

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