# Chemical Variability of the Leaf Essential Oil of Two Subspecies of Juniperus oxycedrus L. From Northwestern Algeria

Charaf Eddine Watheq Malti, Chahrazed Bekhechi, Khadidja Salhi, Brahim Babali, Joseph Casanova, Mathieu Paoli, Félix Tomi

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Charaf Eddine Watheq Malti, Chahrazed Bekhechi, Khadidja Salhi, Brahim Babali, Joseph Casanova, et al.. Chemical Variability of the Leaf Essential Oil of Two Subspecies of Juniperus oxycedrus L. From Northwestern Algeria. Chemistry and Biodiversity, 2024, 22 (2), 10.1002/cbdv.202401584. hal-05034554

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# Chemical Variability of the Leaf Essential Oil of Two Subspecies of *Juniperus oxycedrus* L. From Northwestern Algeria

Charaf Eddine Watheq Malti,[a, b] Chahrazed Bekhechi,[b] Khadidja Salhi,[b] Brahim Babali,[c] Joseph Casanova,[d] Mathieu Paoli,[d] and Félix Tomi*[d]

Thirty-seven essential oil samples have been isolated from leaves of individual plants of *Juniperus oxycedrus* (subspecies *oxycedrus* and *macrocarpa*) growing wild in Tlemcen and Aïn Témouchent provinces (Northwestern Algeria). Analysis of eight selected oil samples by GC(RI), GC/MS and ¹³C NMR, allowed the identification of 88 components that accounted for 84.4–99.5% of the whole compositions. The 37 compositions were subjected to statistical analysis which suggested the existence of

groups and sub-groups I, IIA and IIB. Group I, the most important group with 24 oil samples out of 37, differed from sub-groups IIA and IIB, essentially by the high content of α-pinene (mean value, 69.2%; SD 6.24). Sub-groups IIA and IIB were differentiated by their content of α-pinene (Mean values, 49.7% and 27.3%, respectively) as well as δ-3-carene (10.3%, sub-group IIA), sabinene and (Z)-6-pentadecen-2-one (8.7% and 4.9%, respectively, sub-group IIB).

## Introduction

*Juniperus oxycedrus* L. (Cupressaceae family) chiefly a Mediterranean species, is an evergreen dioecious shrub. In the flora of Algeria, it is recognized three subspecies, including: subsp. *badia* (H. Gay) Deb., subsp. *macrocarpa* (S. & Sm.) Ball. and subsp. *oxycedrus* [Syn. subsp. *rufescens* (Link) Deb.]. [1,2] *J. oxycedrus* commonly known in Algeria as "Taga", [1] grows from North Africa (Morocco, Algeria and Tunisia), into Portugal, Spain, France, Italy, Greece, the Balkans, Turkey and eastward into Iran. [3]

Cade oil (empyreumatic oil) prepared by the destructive distillation of dry wood of *J. oxycedrus*, was largely employed as an antiparasitic and antiseptic for skin diseases, psoriasis and chronic eczema. [4] This plant is widely used as traditional

medicine. It is recommended against diabetes, diarrhea, dermatitis, rheumatism and eye infections.[5-7]

Oils of *J. oxycedrus* have many biological activities such as antibacterial,[8-11] antifungal,[8] antibiofilm,[11] anti-quorum sensing,[12] antioxidant,[12-14] anti-tyrosinase and anti-cholinesterase.[13]

The composition of essential oil isolated from berries (fruits) of Algerian *J. oxycedrus* has been investigated. Most studies reported on the composition of a unique oil sample and concerned the subsp. *oxycedrus*. [12,15-17] α-Pinene (56.4–88.4%) was the major component in three out of four reported compositions; followed by myrcene (6.7–10.4%) and germa-crene D (14.2%) or α-amorphene (9.0%). The chemical composition of the fourth sample was dominated by germa-crene D (38.3%) and α-pinene (17.7%). More informative was the work recently published by our groups. Indeed, the chemical composition of 33 oil samples isolated from the berries of individual trees of two subspecies of *J. oxycedrus* L., collected in Northwestern Algeria, was investigated and submitted to statistical analysis. Groups and sub-groups were distinguished with respect to their contents of α-pinene, germacrene D, myrcene and manoyl oxide.[18]

In contrast, the composition of essential oil isolated from aerial parts (generally leaves and eventually stems) of Algerian *J. oxycedrus* subsp. *oxycedrus* and/or subsp. *macrocarpa* has been widely investigated although every report concerned only one oil sample.[9,11-14,19-26]

In six oil samples out of nine belonging to the *oxycedrus* subspecies, α-pinene was the major component although its content varied drastically from 23.6% to 56.1%. Other components present at appreciable content were very different from sample to sample: β-phellandrene,[11] sabinene and terpinen-4-ol,[14] δ-3-carene,[19] germacrene D,[20] bulnesol,[13] epi-manoyl oxide and (E,E)-farnesol,[14] abietadiene.[12,13] The last three oil samples of the *oxycedrus* subspecies displayed very different

<footnote>[a] C. E. W. Malti
Faculté des Sciences et Technologies, Université Ahmed Zabana, Cité Bourmadia, 48000 Relizane, Algérie</footnote>

<footnote>[b] C. E. W. Malti, C. Bekhechi, K. Salhi
Laboratoire des Produits Naturels, Département de Biologie, Université Abou Bekr Belkaïd, Imama, 13000 Tlemcen, Algérie</footnote>

<footnote>[c] B. Babali
Laboratoire d'Ecologie et Gestion des Ecosystèmes Naturels, Département d'Ecologie et Environnement, Université Abou Bekr Belkaïd, Imama, 13000 Tlemcen, Algérie.</footnote>

<footnote>[d] J. Casanova, M. Paoli, F. Tomi
Université de Corse-CNRS, UMR 6134 SPE, Route des Sanguinaires, 20000 Ajaccio, France
E-mail: tomi_f@univ-corse.fr</footnote>

<footnote>Supporting information for this article is available on the WWW under
https://doi.org/10.1002/cbdv.202401584</footnote>

<footnote>© 2024 The Author(s). Chemistry & Biodiversity published by Wiley-VHCA AG. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.</footnote>
compositions. The monoterpane-rich oil sample from Mostaganem contained mainly terpinen-4-ol (17.48%), α-pinene (14.85%) and sabinene (14.93%).[21] One oil sample from Tiaret Forest displayed germacrene D (27.41%) δ-3-carene (24.73%) and myrcene (13.85%) as major components.[22] In an oil sample from Tébessa various oxygenated pinane derivatives were detected, trans-pinocarveol (7.0%), cis-verbenol (6.3%), pinocarvone (5.1%).[23]

Otherwise, α-pinene (29.1%), β-pinene (17.6%) and β-copaene (19.3%) were the major components of an essential oil isolated from leaves and fruits of *J. oxycedrus* ssp. *oxycedrus* harvested in Tiaret Forest.[24] In contrast, another oil sample isolated from leaves, stems and fruits harvested in the Aures contained mainly manoyl oxide (23.4%) beside (Z)-pentadec-6-en-2-one (12.6%).[25]

The composition of two oil samples of the subspecies *macrocarpa* has also been investigated. The composition of the former from El Kala) was dominated by germacrene D (21.3%), followed by (Z,Z)-farnesol (10.9%).[26] The major component of the sample from Oum El Bouaghi was the uncommon 5-(Z)-tetradecen-1-yl acetate (12.9%).[9]

In a recent study, we evidenced a variability in the chemical composition of essential oils isolated from berries of *J. oxycedrus* (*oxycedrus* and *macrocarpa* subspecies) growing wild in provinces of Tlemcen and Aïn Témouchent, Northwestern Algeria.[18] Statistical analyses suggested the existence of two groups which were distinguished on the basis of α-pinene content. According to the amounts of α-pinene, germacrene D and myrcene, as well as manoyl oxide, group II was divided into two sub-groups. The chemical composition of the essential oils belonging to subsp. *oxycedrus* was dominated by monoterpenes. The main constituents were α-pinene (23.7–63.2%) with appreciable contents of germacrene D (4.5–25.4%). In contrast, germacrene D (4.4–30.0%) was the major component in oil samples of subsp. *macrocarpa*, accompanied by a lower content of α-pinene (10.0–24.3%) and a significant amount of manoyl oxide (4.3–9.9%).[18]

The chemical variability of *J. oxycedrus* essential oil has been evidenced in a few countries and in a Mediterranean island:

- For instance, regarding essential oils isolated from 60 individual trees growing in Tunisia, the content of the major components varied substantially from sample to sample: α-pinene (24.32–58.03%), geranyl acetone (1.96–8.80%), 13-epi-manoyl oxide (1.35–6.95%). Hierarchical clustering and principal component analysis (PCA) allowed to establish four groups; one group being divided into two sub-groups. The oils of the population from the continental site were clearly distinguished from those of the littoral localities[27]:

- The essential oil samples of *J. oxycedrus* collected among 20 populations across Bulgaria contained mainly α-pinene, limonene, α-curcumene, γ-cadinene, δ-cadinene, germacrene D, β-caryophyllene, α-caryophyllene, caryophyllene oxide and manoyl oxide, and they were grouped in eight chemotypes using advanced statistical methods[28],

- The composition of 54 samples of leaf oil of *Juniperus oxycedrus* ssp. *oxycedrus* from Corsica was investigated. The main constituents were α-pinene, β-phellandrene and δ-3-

carene. Principal component analysis, allowed the distinction of two compositions differentiated by the contents of α-pinene, β-phellandrene and δ-3-carene. In parallel, the chemical compositions of 18 leaf oil samples of *J. oxycedrus* ssp. *macrocarpa* have been investigated. The contents of the main components varied drastically from sample to sample: α-pinene (28.7–76.4%), δ-3-carene (up to 17.3%), β-phellandrene (up to 12.3%), manoyl oxide (up to 8.1%). Principal component analysis, as well as k-means partition suggested a unique group, with few atypical samples. In the main group, α-pinene (43.3–63.8%) was accompanied by β-phellandrene (up to 11.9%), δ-3-carene (up to 7.5%) and manoyl oxide (up to 4.5%).[30]

Obviously, it appears from literature data that essential oil samples isolated from leaves (or aerial parts) of *Juniperus oxycedrus* displayed substantially different compositions. So, the aim of this study was to characterize the yield and the chemical composition of the essential oil from the leaves of *Juniperus oxycedrus* subsp. *oxycedrus* and subsp. *macrocarpa*, growing wild in Tlemcen and Aïn Témouchent provinces, Northwestern Algeria.

Firstly, we will report on the detailed analysis of eight essential oil samples, by combination of chromatographic and spectroscopic techniques. Secondly, the compositions of 37 leaf oil samples isolated from individual plants, were submitted to statistical analysis in order to evidence homogeneity or an eventual chemical variability.

## Results and Discussion

Leaves of 37 individual plants from *Juniperus oxycedrus* have been harvested in two provinces of Northwestern Algeria, Tlemcen (three locations, Ouled Mimoun, Terny and Aïn Fezza) and Aïn Témouchent (one location, Béni Saf) (Figure 1); two subspecies, subsp. *oxycedrus* (28 individuals) and subsp. *macrocarpa* (9 individuals). Leaves of individual plants have been hydrodistilled using a Clevenger-type apparatus, yielding colorless essential oil samples. We will report first on the yield of essential oil depending of the subspecies and the location of harvest, then, on the detailed analysis of eight oil samples, selected on the basis of their chromatographic profiles, by GC in combination with retention indices on two chromatographic columns of different polarity, by GC/MS and by ¹³C NMR,

<figure><img src="image_5.png" /><figcaption>**Figure 1.** Sampling provinces of *Juniperus oxycedrus* from Northwestern of Algeria.</figcaption></figure>
<table><caption>**Table 1.** Yields (%) of the essential oils isolated from leaves of two subspecies of *Juniperus oxycedrus*.</caption><thead><tr><th>Locations of harvest</th><th>samples</th><th>Mean ± SD<sup>[a]</sup> (%)</th><th>Min<sup>[b]</sup></th><th>Max<sup>[c]</sup></th><th>Subspecies</th></tr></thead><tbody><tr><td>Ouled Mimoun</td><td>9</td><td>0.09 ± 0.05</td><td>0.04</td><td>0.19</td><td>oxycedrus</td></tr><tr><td>Terny</td><td>9</td><td>0.11 ± 0.07</td><td>0.01</td><td>0.20</td><td>oxycedrus</td></tr><tr><td>Aïn Fezza</td><td>10</td><td>0.06 ± 0.03</td><td>0.03</td><td>0.12</td><td>oxycedrus</td></tr><tr><td>Béni Saf</td><td>9</td><td>0.08 ± 0.04</td><td>0.02</td><td>0.16</td><td>macrocarpa</td></tr></tbody></table>

[a] Standard deviation (SD); [b] Minimum (Min); [c] Maximum (Max)

without isolation of the individual components,[31,32] lastly, on the statistical analysis of the 37 compositions.

(2.5% vs. 0.3–2.2%) and diterpenes, namely abietadiene (5.4% vs. 0.2–1.8%) and manoyl oxide (3.1% vs. 0.0–0.9%).

## Essential Oil Yield

The yields of *J. oxycedrus* leaf essential oil (LEO) (w/w vs. dry material) varied substantially from sample to sample, even within subspecies, ranging between 0.01 to 0.20% for the *oxycedrus* subspecies (28 samples) and from 0.02% to 0.16% for the *macrocarpa* subspecies (9 samples) (Table 1). The highest yields (0.11 ± 0.07%) were observed for the plants collected in Terny and the lowest (0.06 ± 0.03%) were observed for the plants harvested in Aïn Fezza, while similar yield mean values (0.09% and 0.08%) have been calculated for the plants harvested in Ouled Mimoun (*oxycedrus* subspecies) and Béni Saf (*macrocarpa* subspecies), respectively.

## Chemical Composition of Selected Oil Samples

Eight oil samples, six of the subspecies *oxycedrus* and two of the subspecies *macrocarpa*, selected on the basis of their chromatographic profile, were submitted to gas chromatography (GC), in combination with retention indices (RIs) on two columns of different polarity, gas chromatography mass spectroscopy (GC/MS) and ¹³C nuclear magnetic resonance (NMR), following a computerized method developed at University of Corsica.[31,32] The detailed analyses of those eight samples were reported in Table 2. In total, 88 compounds were identified, accounting for 84.4–99.5% of the whole compositions, which were largely dominated by monoterpane hydrocarbons (68.6–83.9%), sample S15 excepted (36.2%). In seven oil samples, α-pinene (43.7–72.1%) was by far the major component followed by δ-3-carene (up to 12.8%) and β-phellandrene (up to 11.0%). Myrcene (1.4–7.8%), β-pinene (0.9–4.1%), sabinene (0.1–3.4%) and *p*-cymene (0.2–3.1%) were found to be the other monoterpane hydrocarbons present at appreciable contents. Germacrene D (0.9–7.2%) was the only sesquiterpene hydrocarbon present in a significant amount, beside γ-cadinene (0.3–1.8%), (*E*)-β-caryophyllene (0.2–1.1%), δ-cadinene (0.1–1.0%) and α-humulene (0.0–1.0%). The occurrence of (Z)-6-pentadecen-2-one (0.1–1.8%) could be highlighted. Conversely, the main components of sample S15 were α-pinene (28.1%) and germacrene D (15.7%), followed by oxygenated sesquiterpenes, namely: 2,3-dihydrofarnesol (3.6% vs. 0.0–1.1%), (2E,6E)-farnesol

## Chemical Variability

Thirty-seven essential oil samples were obtained by hydro-distillation of leaves collected from individual trees of *J. oxycedrus* in four locations of Northwestern of Algeria: Ouled Mimoun, Terny and Aïn Fezza (Tlemcen province, *oxycedrus* subspecies, 28 samples) and Béni Saf (Aïn Témouchent province, *macrocarpa* subspecies, 9 samples) (Figure 1).

The 37 compositions were subjected to statistical analysis in order to distinguish clusters. The combination of hierarchical clustering dendrogram (HCA, Figure 2), and principal component analysis (PCA; Figure 3), for which the two axes (F1 and F3) accounted for 85.7% of the total variance of the population, suggested the existence of two principal groups, one of these being subdivided into two sub groups IIA and IIB.

Group I, by far the most important group with 24 oil samples out of 37, differed from sub-groups IIA and IIB, essentially by the content of α-pinene (69.2%, mean value, SD 6.24; vs. 49.7%, SD 7.27 and 27.3%, SD 7.89) (Table 3).

<figure><img src="image_6.png" /><figcaption>**Figure 2.** Hierarchical Cluster Analysis of the compositions of the 37 LEO of two subspecies of *Juniperus oxycedrus*.</figcaption></figure>
<table><caption>**Table 2.** Chemical composition of LEO of two subspecies of *J. oxycedrus*.</caption><thead><tr><th></th><th>Compounds<sup>[a]</sup></th><th>Rla<sup>[b]</sup></th><th>Rlp<sup>[b]</sup></th><th>RlaL<sup>[c]</sup></th><th>RlpL<sup>[c]</sup></th><th>S24<sup>[d]</sup></th><th>S19<sup>[d]</sup></th><th>S5<sup>[d]</sup></th><th>S10<sup>[d]</sup></th><th>S1<sup>[d]</sup></th><th>S15<sup>[d]</sup></th><th>S29<sup>[e]</sup></th><th>S33<sup>[e]</sup></th><th>Identification</th></tr></thead><tbody><tr><td>1</td><td>Hexanal</td><td>772</td><td>1081</td><td>777</td><td>1082</td><td>0.2</td><td>0.2</td><td>0.6</td><td>0.1</td><td>1.3</td><td>0.4</td><td>0.2</td><td>-</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>2</td><td>(E)-Hex-2-enal</td><td>823</td><td>1221</td><td>827</td><td>1216</td><td>0.2</td><td>0.1</td><td>0.3</td><td>0.1</td><td>1.3</td><td>0.3</td><td>0.5</td><td>0.2</td><td>RI, MS</td></tr><tr><td>3</td><td>Hexan-1-ol</td><td>846</td><td>1347</td><td>855</td><td>1351</td><td>Tr</td><td>-</td><td>0.1</td><td>-</td><td>0.4</td><td>-</td><td>0.2</td><td>0.3</td><td>RI, MS</td></tr><tr><td>4</td><td>Tricyclene</td><td>919</td><td>nd</td><td>922</td><td>1012</td><td>0.2</td><td>0.2</td><td>0.3</td><td>0.2</td><td>0.1</td><td>0.1</td><td>0.2</td><td>0.1</td><td>RI, MS</td></tr><tr><td>5</td><td>α-Thujene</td><td>921</td><td>1014</td><td>926</td><td>1027</td><td>0.1</td><td>Tr</td><td>0.1</td><td>Tr</td><td>Tr</td><td>0.1</td><td>0.8</td><td>0.5</td><td>RI, MS</td></tr><tr><td>6</td><td>α-Pinene</td><td>930</td><td>1014</td><td>935</td><td>1025</td><td>72.1</td><td>62.3</td><td>61.7</td><td>57.4</td><td>48.8</td><td>28.1</td><td>67.0</td><td>43.7</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>7</td><td>α-Fenchene</td><td>940</td><td>1050</td><td>945</td><td>1061</td><td>0.1</td><td>Tr</td><td>0.7</td><td>Tr</td><td>Tr</td><td>0.1</td><td>0.1</td><td>0.5</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>8</td><td>Camphene</td><td>942</td><td>1062</td><td>947</td><td>1069</td><td>0.4</td><td>0.3</td><td>0.3</td><td>0.3</td><td>0.4</td><td>0.1</td><td>0.3</td><td>0.2</td><td>RI, MS</td></tr><tr><td>9</td><td>Verbenene</td><td>945</td><td>1124</td><td>946</td><td>1124</td><td>0.2</td><td>0.3</td><td>0.5</td><td>0.2</td><td>0.2</td><td>0.1</td><td>0.1</td><td>0.3</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>10</td><td>1-Octen-3-ol</td><td>959</td><td>1444</td><td>966</td><td>1444</td><td>0.2</td><td>0.2</td><td>0.7</td><td>0.1</td><td>0.1</td><td>0.2</td><td>0.3</td><td>2.0</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>11</td><td>Sabinene</td><td>963</td><td>1119</td><td>968</td><td>1122</td><td>0.3</td><td>0.2</td><td>0.2</td><td>0.2</td><td>0.1</td><td>0.3</td><td>2.7</td><td>3.4</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>12</td><td>β-Pinene</td><td>969</td><td>1109</td><td>973</td><td>1110</td><td>1.7</td><td>1.6</td><td>1.4</td><td>2.3</td><td>4.1</td><td>0.8</td><td>0.9</td><td>1.2</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>13</td><td>Myrcene</td><td>979</td><td>1158</td><td>983</td><td>1161</td><td>1.5</td><td>1.4</td><td>1.4</td><td>2.3</td><td>3.7</td><td>0.7</td><td>7.8</td><td>2.1</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>14</td><td>2-Carene</td><td>994</td><td>1128</td><td>998</td><td>1134</td><td>0.1</td><td>0.4</td><td>0.2</td><td>0.6</td><td>0.5</td><td>0.1</td><td>0.1</td><td>0.1</td><td>RI, SM, <sup>13</sup>C NMR</td></tr><tr><td>15</td><td>α-Phellandrene</td><td>996</td><td>1162</td><td>999</td><td>1168</td><td>Tr</td><td>-</td><td>0.3</td><td>0.4</td><td>0.7</td><td>0.1</td><td>-</td><td>0.1</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>16</td><td>δ-3-Carene</td><td>1004</td><td>1145</td><td>1007</td><td>1147</td><td>0.1</td><td>Tr</td><td>8.2</td><td>-</td><td>Tr</td><td>3.0</td><td>0.6</td><td>12.8</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>17</td><td>α-Terpinene</td><td>1008</td><td>1177</td><td>1011</td><td>1178</td><td>Tr</td><td>-</td><td>Tr</td><td>-</td><td>-</td><td>0.1</td><td>0.2</td><td>0.3</td><td>RI, MS</td></tr><tr><td>18</td><td>p-Cymene</td><td>1011</td><td>1268</td><td>1015</td><td>1270</td><td>0.6</td><td>0.2</td><td>1.3</td><td>1.6</td><td>3.1</td><td>0.9</td><td>0.8</td><td>1.5</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>19</td><td>Limonene*</td><td>1020</td><td>1198</td><td>1024</td><td>1198</td><td>1.0</td><td>1.3</td><td>1.0</td><td>1.7</td><td>1.9</td><td>0.5</td><td>1.4</td><td>1.1</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>20</td><td>β-Phellandrene*</td><td>1020</td><td>1208</td><td>1021</td><td>1209</td><td>1.6</td><td>0.3</td><td>3.5</td><td>6.3</td><td>11.0</td><td>0.6</td><td>0.1</td><td>1.2</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>21</td><td>γ-Terpinene</td><td>1047</td><td>1242</td><td>1050</td><td>1245</td><td>-</td><td>-</td><td>Tr</td><td>-</td><td>-</td><td>0.1</td><td>0.4</td><td>0.5</td><td>RI, MS</td></tr><tr><td>22</td><td>1-Octanol</td><td>1051</td><td>1552</td><td>1057</td><td>1552</td><td>0.1</td><td>0.1</td><td>Tr</td><td>0.1</td><td>Tr</td><td>0.1</td><td>0.1</td><td>0.5</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>23</td><td>p-Cymenene</td><td>1071</td><td>1435</td><td>1074</td><td>1438</td><td>0.1</td><td>0.1</td><td>0.1</td><td>0.1</td><td>0.1</td><td>0.1</td><td>Tr</td><td>0.1</td><td>RI, MS</td></tr><tr><td>24</td><td>Terpinolene</td><td>1077</td><td>1280</td><td>1079</td><td>1282</td><td>-</td><td>-</td><td>0.3</td><td>0.3</td><td>0.2</td><td>0.3</td><td>0.4</td><td>1.4</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>25</td><td>Linalool*</td><td>1082</td><td>1542</td><td>1086</td><td>1543</td><td>0.5</td><td>0.3</td><td>0.2</td><td>0.1</td><td>0.3</td><td>0.3</td><td>Tr</td><td>0.2</td><td>RI, MS</td></tr><tr><td>26</td><td>α-Pinene oxide*</td><td>1082</td><td>1374</td><td>1085</td><td>1364</td><td>Tr</td><td>Tr</td><td>-</td><td>Tr</td><td>Tr</td><td>Tr</td><td>0.1</td><td>-</td><td>RI, MS</td></tr><tr><td>27</td><td>α-Campholenal</td><td>1103</td><td>1487</td><td>1107</td><td>1496</td><td>0.2</td><td>0.4</td><td>0.6</td><td>0.2</td><td>0.2</td><td>0.2</td><td>0.2</td><td>0.3</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>28</td><td>Fenchol*</td><td>1103</td><td>1583</td><td>1101</td><td>1570</td><td>0.2</td><td>0.2</td><td>0.1</td><td>0.2</td><td>0.1</td><td>0.1</td><td>0.2</td><td>0.3</td><td>RI, MS</td></tr><tr><td>29</td><td>Camphor</td><td>1118</td><td>1512</td><td>1125</td><td>1515</td><td>Tr</td><td>0.1</td><td>Tr</td><td>Tr</td><td>0.1</td><td>-</td><td>-</td><td>0.1</td><td>RI, MS</td></tr><tr><td>30</td><td>trans-Pinocarveol</td><td>1121</td><td>1650</td><td>1126</td><td>1661</td><td>0.5</td><td>1.3</td><td>1.2</td><td>0.4</td><td>0.5</td><td>0.3</td><td>0.3</td><td>0.7</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>31</td><td>cis-Verbenol</td><td>1123</td><td>1650</td><td>1126</td><td>1660</td><td>-</td><td>0.3</td><td>0.1</td><td>-</td><td>-</td><td>0.1</td><td>-</td><td>0.3</td><td>RI, MS</td></tr><tr><td>32</td><td>trans-Verbenol</td><td>1127</td><td>1673</td><td>1134</td><td>1680</td><td>0.3</td><td>1.2</td><td>0.7</td><td>0.3</td><td>0.2</td><td>0.2</td><td>0.2</td><td>1.3</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>33</td><td>p-Menth-3-en-8-ol</td><td>1133</td><td>1597</td><td>1140<sup>f</sup></td><td>1600<sup>f</sup></td><td>-</td><td>-</td><td>Tr</td><td>-</td><td>-</td><td>Tr</td><td>-</td><td>-</td><td>RI, MS</td></tr><tr><td>34</td><td>trans-Pinocamphone*</td><td>1137</td><td>1511</td><td>1144</td><td>1523</td><td>0.1</td><td>0.6</td><td>0.5</td><td>Tr</td><td>0.7</td><td>0.1</td><td>0.3</td><td>0.4</td><td>RI, MS, <sup>13</sup>C NMR</td></tr></tbody></table>
<table><caption>**Table 2. continued**</caption><thead><tr><th></th><th>Compounds<sup>[a]</sup></th><th>Rla<sup>[b]</sup></th><th>Rlp<sup>[b]</sup></th><th>RlaL<sup>[c]</sup></th><th>RlpL<sup>[c]</sup></th><th>S24<sup>[d]</sup></th><th>S19<sup>[d]</sup></th><th>S5<sup>[d]</sup></th><th>S10<sup>[d]</sup></th><th>S1<sup>[d]</sup></th><th>S15<sup>[d]</sup></th><th>S29<sup>[e]</sup></th><th>S33<sup>[e]</sup></th><th>Identification</th></tr></thead><tbody><tr><td>35</td><td>Pinocarvone*</td><td>1137</td><td>1564</td><td>1140</td><td>1576</td><td>0.1</td><td>0.3</td><td>0.4</td><td>0.2</td><td>0.2</td><td>0.1</td><td>Tr</td><td>Tr</td><td>RI, MS</td></tr><tr><td>36</td><td>p-Mentha-1,5-dien-8-ol</td><td>1144</td><td>1721</td><td>1149</td><td>1725</td><td>0.1</td><td>0.1</td><td>0.3</td><td>0.1</td><td>0.1</td><td>0.1</td><td>0.1</td><td>0.4</td><td>RI, MS,</td></tr><tr><td>37</td><td>Borneol</td><td>1147</td><td>1695</td><td>1153</td><td>1700</td><td>-</td><td>-</td><td>0.1</td><td>Tr</td><td>0.1</td><td>-</td><td>0.1</td><td>0.2</td><td>RI, MS</td></tr><tr><td>38</td><td>Cryptone</td><td>1154</td><td>1661</td><td>1157</td><td>1675</td><td>0.1</td><td>-</td><td>0.4</td><td>0.4</td><td>0.5</td><td>Tr</td><td>-</td><td>0.2</td><td>RI, MS</td></tr><tr><td>39</td><td>p-Cymene-8-ol</td><td>1158</td><td>1844</td><td>1165</td><td>1848</td><td>-</td><td>-</td><td>0.4</td><td>0.2</td><td>0.1</td><td>0.1</td><td>0.1</td><td>0.4</td><td>RI, MS</td></tr><tr><td>40</td><td>Terpinen-4-ol</td><td>1160</td><td>1597</td><td>1165</td><td>1601</td><td>0.2</td><td>0.2</td><td>0.1</td><td>0.1</td><td>Tr</td><td>0.2</td><td>1.4</td><td>1.8</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>41</td><td>Myrtenal</td><td>1168</td><td>1623</td><td>1171</td><td>1632</td><td>0.1</td><td>0.3</td><td>0.4</td><td>0.1</td><td>0.1</td><td>0.1</td><td>0.1</td><td>0.3</td><td>RI, MS,</td></tr><tr><td>42</td><td>α-Terpineol</td><td>1170</td><td>1692</td><td>1176</td><td>1694</td><td>0.2</td><td>0.1</td><td>0.2</td><td>0.1</td><td>0.3</td><td>0.2</td><td>0.5</td><td>0.4</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>43</td><td>Myrtenol</td><td>1177</td><td>1786</td><td>1182</td><td>1790</td><td>0.1</td><td>0.3</td><td>0.3</td><td>0.2</td><td>0.1</td><td>0.1</td><td>0.1</td><td>0.3</td><td>RI, MS</td></tr><tr><td>44</td><td>Verbenone</td><td>1183</td><td>1715</td><td>1184</td><td>1721</td><td>Tr</td><td>-</td><td>0.1</td><td>-</td><td>0.2</td><td>-</td><td>Tr</td><td>0.1</td><td>RI, MS</td></tr><tr><td>45</td><td>trans-Carveol</td><td>1195</td><td>1829</td><td>1201</td><td>1836</td><td>0.1</td><td>0.3</td><td>0.3</td><td>0.1</td><td>0.1</td><td>0.1</td><td>0.1</td><td>0.2</td><td>RI, MS</td></tr><tr><td>46</td><td>cis-Carveol</td><td>1212</td><td>1865</td><td>1206</td><td>1854</td><td>0.1</td><td>0.1</td><td>0.1</td><td>0.3</td><td>0.2</td><td>Tr</td><td>0.1</td><td>0.1</td><td>RI, MS</td></tr><tr><td>47</td><td>Bornyl acetate</td><td>1267</td><td>1575</td><td>1270</td><td>1579</td><td>-</td><td>-</td><td>Tr</td><td>-</td><td>0.3</td><td>0.3</td><td>0.1</td><td>0.3</td><td>RI, MS</td></tr><tr><td>48</td><td>α-Terpinyll acetate</td><td>1329</td><td>1680</td><td>1333</td><td>1695</td><td>0.1</td><td>0.1</td><td>0.1</td><td>0.1</td><td>0.5</td><td>0.1</td><td>0.1</td><td>0.1</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>49</td><td>α-Cubebene</td><td>1345</td><td>1450</td><td>1352</td><td>1460</td><td>0.1</td><td>-</td><td>Tr</td><td>Tr</td><td>Tr</td><td>0.1</td><td>0.1</td><td>0.1</td><td>RI, MS</td></tr><tr><td>50</td><td>α-Ylangene</td><td>1367</td><td>1476</td><td>1370</td><td>1484</td><td>-</td><td>-</td><td>-</td><td>-</td><td>Tr</td><td>0.1</td><td>Tr</td><td>-</td><td>RI, MS</td></tr><tr><td>51</td><td>α-Copaene</td><td>1371</td><td>1484</td><td>1376</td><td>1491</td><td>0.1</td><td>-</td><td>-</td><td>0.1</td><td>Tr</td><td>0.1</td><td>0.1</td><td>Tr</td><td>RI, MS</td></tr><tr><td>52</td><td>β-Elemene</td><td>1384</td><td>1583</td><td>1388</td><td>1591</td><td>Tr</td><td>0.1</td><td>Tr</td><td>0.2</td><td>0.1</td><td>0.2</td><td>0.1</td><td>0.2</td><td>RI, MS</td></tr><tr><td>53</td><td>(E)-β-Caryophyllene</td><td>1413</td><td>1589</td><td>1419</td><td>1599</td><td>0.6</td><td>0.9</td><td>0.2</td><td>1.1</td><td>0.6</td><td>1.7</td><td>0.4</td><td>0.2</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>54</td><td>β-Coapene</td><td>1422</td><td>1583</td><td>1427</td><td>1580</td><td>0.1</td><td>0.1</td><td>Tr</td><td>0.1</td><td>0.1</td><td>0.2</td><td>0.1</td><td>0.1</td><td>RI, MS</td></tr><tr><td>55</td><td>(E)-β-Farnesene</td><td>1443</td><td>1661</td><td>1449</td><td>1664</td><td>-</td><td>-</td><td>0.1</td><td>0.1</td><td>0.1</td><td>-</td><td>0.1</td><td>-</td><td>RI, MS</td></tr><tr><td>56</td><td>α-Humulene</td><td>1446</td><td>1661</td><td>1449</td><td>1667</td><td>0.6</td><td>0.9</td><td>-</td><td>1.0</td><td>0.4</td><td>1.4</td><td>0.4</td><td>0.1</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>57</td><td>γ-Muurolene</td><td>1467</td><td>1679</td><td>1473</td><td>1690</td><td>0.5</td><td>0.4</td><td>0.1</td><td>0.7</td><td>0.3</td><td>0.7</td><td>0.5</td><td>0.2</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>58</td><td>Germacrene D</td><td>1472</td><td>1701</td><td>1476</td><td>1708</td><td>2.2</td><td>5.7</td><td>0.9</td><td>7.2</td><td>2.1</td><td>15.7</td><td>4.2</td><td>4.1</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>59</td><td>2-Tridecanone</td><td>1471</td><td>1801</td><td>1479</td><td>1808</td><td>0.6</td><td>0.4</td><td>0.2</td><td>0.2</td><td>0.2</td><td>-</td><td>-</td><td>0.1</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>60</td><td>β-Selinene</td><td>1477</td><td>1710</td><td>1481</td><td>1717</td><td>Tr</td><td>-</td><td>-</td><td>-</td><td>Tr</td><td>Tr</td><td>Tr</td><td>Tr</td><td>RI, MS</td></tr><tr><td>61</td><td>α-Muurolene</td><td>1489</td><td>1715</td><td>1491</td><td>1723</td><td>0.2</td><td>0.3</td><td>0.1</td><td>-</td><td>0.2</td><td>0.5</td><td>0.2</td><td>0.2</td><td>RI, MS</td></tr><tr><td>62</td><td>β-Bisabolene</td><td>1496</td><td>1719</td><td>1500</td><td>1728</td><td>Tr</td><td>-</td><td>-</td><td>Tr</td><td>0.1</td><td>0.2</td><td>-</td><td>0.1</td><td>RI, MS</td></tr><tr><td>63</td><td>γ-Cadinene</td><td>1501</td><td>1749</td><td>1506</td><td>1763</td><td>0.3</td><td>0.5</td><td>0.5</td><td>1.8</td><td>1.1</td><td>0.6</td><td>0.3</td><td>0.3</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>64</td><td>Calamenene<sup>[g]</sup></td><td>1505</td><td>1824</td><td>1510</td><td>1835</td><td>0.1</td><td>Tr</td><td>-</td><td>0.1</td><td>Tr</td><td>0.1</td><td>Tr</td><td>Tr</td><td>RI, MS</td></tr><tr><td>65</td><td>δ-Cadinene</td><td>1510</td><td>1749</td><td>1514</td><td>1756</td><td>0.7</td><td>0.6</td><td>0.1</td><td>0.7</td><td>0.3</td><td>1.5</td><td>0.8</td><td>1.0</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>66</td><td>α-Calacorene</td><td>1523</td><td>1907</td><td>1530</td><td>1921</td><td>-</td><td>-</td><td>-</td><td>-</td><td>Tr</td><td>Tr</td><td>Tr</td><td>0.1</td><td>RI, MS</td></tr><tr><td>67</td><td>α-Cadinene</td><td>1526</td><td>1783</td><td>1527</td><td>1769</td><td>Tr</td><td>Tr</td><td>Tr</td><td>0.1</td><td>0.1</td><td>Tr</td><td>Tr</td><td>0.1</td><td>RI, MS</td></tr><tr><td>68</td><td>β-Elemol</td><td>1530</td><td>2071</td><td>1537</td><td>2088</td><td>Tr</td><td>-</td><td>-</td><td>-</td><td>-</td><td>0.1</td><td>-</td><td>0.4</td><td>RI, MS</td></tr><tr><td>69</td><td>Salviadienol</td><td>1534</td><td>2103</td><td>1545<sup>[h]</sup></td><td>2110<sup>[h]</sup></td><td>0.3</td><td>0.6</td><td>0.3</td><td>0.3</td><td>0.3</td><td>0.5</td><td>0.3</td><td>0.2</td><td>RI, MS</td></tr><tr><td>70</td><td>(E)-Nerolidol</td><td>1546</td><td>2035</td><td>1550</td><td>2036</td><td>-</td><td>-</td><td>-</td><td>-</td><td>Tr</td><td>-</td><td>-</td><td>0.2</td><td>RI, MS</td></tr><tr><td>71</td><td>Caryophyllene oxide</td><td>1566</td><td>1972</td><td>1570</td><td>1986</td><td>0.3</td><td>0.6</td><td>0.3</td><td>0.2</td><td>0.3</td><td>0.4</td><td>0.1</td><td>Tr</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>72</td><td>Salvial-4(14)-en-1-one</td><td>1573</td><td>1997</td><td>1585</td><td>2036</td><td>0.1</td><td>0.2</td><td>0.1</td><td>0.1</td><td>0.1</td><td>0.1</td><td>0.1</td><td>0.1</td><td>RI, MS</td></tr></tbody></table>
<table><caption>**Table 2. continued**</caption><thead><tr><th></th><th>Compounds<sup>[a]</sup></th><th>Rla<sup>[b]</sup></th><th>Rlp<sup>[b]</sup></th><th>RlaL<sup>[c]</sup></th><th>RlpL<sup>[c]</sup></th><th>S24<sup>[d]</sup></th><th>S19<sup>[d]</sup></th><th>S5<sup>[d]</sup></th><th>S10<sup>[d]</sup></th><th>S1<sup>[d]</sup></th><th>S15<sup>[d]</sup></th><th>S29<sup>[e]</sup></th><th>S33<sup>[e]</sup></th><th>Identification</th></tr></thead><tbody><tr><td>73</td><td>cis-Guai-6-en-10-ol</td><td>1590</td><td>1988</td><td>1575<sup>[i]</sup></td><td>2000<sup>[i]</sup></td><td>0.4</td><td>0.9</td><td>0.3</td><td>0.4</td><td>0.4</td><td>0.7</td><td>0.3</td><td>0.2</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>74</td><td>1,10-di-epi-Cubenol</td><td>1610</td><td>2051</td><td>1606</td><td>2074</td><td>0.1</td><td>0.1</td><td>0.1</td><td>0.7</td><td>0.8</td><td>0.1</td><td>Tr</td><td>0.1</td><td>RI, MS</td></tr><tr><td>75</td><td>γ-Eudesmol</td><td>1617</td><td>2163</td><td>1617</td><td>2176</td><td>Tr</td><td>0.2</td><td>0.1</td><td>Tr</td><td>0.1</td><td>0.1</td><td>0.1</td><td>Tr</td><td>RI, MS</td></tr><tr><td>76</td><td>τ-Murolol*</td><td>1620</td><td>2177</td><td>1631</td><td>2186</td><td>0.1</td><td>0.2</td><td>Tr</td><td>0.2</td><td>Tr</td><td>0.3</td><td>0.1</td><td>0.2</td><td>RI, MS</td></tr><tr><td>77</td><td>τ-Cadinol*</td><td>1620</td><td>2160</td><td>1626</td><td>2170</td><td>Tr</td><td>0.1</td><td>0.1</td><td>Tr</td><td>0.2</td><td>0.1</td><td>0.1</td><td>0.1</td><td>RI, MS</td></tr><tr><td>78</td><td>β-Eudesmol</td><td>1631</td><td>2219</td><td>1634</td><td>2223</td><td>-</td><td>0.4</td><td>0.1</td><td>0.1</td><td>0.1</td><td>0.6</td><td>0.2</td><td>0.1</td><td>RI, MS</td></tr><tr><td>79</td><td>α-Cadinol</td><td>1633</td><td>2221</td><td>1640</td><td>2227</td><td>0.2</td><td>0.4</td><td>Tr</td><td>Tr</td><td>0.1</td><td>0.4</td><td>0.3</td><td>0.7</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>80</td><td>(Z)-6-Pentadecen-2-one</td><td>1647</td><td>2027</td><td>1647<sup>[j]</sup></td><td>2030<sup>[j]</sup></td><td>1.7</td><td>1.8</td><td>0.9</td><td>1.6</td><td>1.3</td><td>0.1</td><td>0.1</td><td>0.5</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>81</td><td>Eudesma-4(15),7-dien-1-ol</td><td>1664</td><td>2345</td><td>1676</td><td>2371</td><td>0.1</td><td>0.1</td><td>0.1</td><td>0.1</td><td>0.2</td><td>0.3</td><td>0.2</td><td>0.1</td><td>RI, MS</td></tr><tr><td>82</td><td>2,3-Dihydrofarnesol</td><td>1668</td><td>2260</td><td>1668<sup>[k]</sup></td><td>2262<sup>[l]</sup></td><td>0.5</td><td>1.1</td><td>0.3</td><td>0.3</td><td>0.6</td><td>3.6</td><td>-</td><td>0.3</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>83</td><td>(2Z,6E)-Farnesal</td><td>1685</td><td>2310</td><td>1688<sup>[m]</sup></td><td>2219<sup>[m]</sup></td><td>0.1</td><td>0.2</td><td>0.1</td><td>0.2</td><td>0.1</td><td>0.6</td><td>-</td><td>0.1</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>84</td><td>(2E,6E)-Farnesol</td><td>1697</td><td>2355</td><td>1710</td><td>2366</td><td>0.4</td><td>2.2</td><td>0.3</td><td>0.5</td><td>0.9</td><td>2.5</td><td>0.5</td><td>0.6</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>85</td><td>(2E,6E)-Farnesal</td><td>1711</td><td>2257</td><td>1715<sup>[n]</sup></td><td>2264<sup>[n]</sup></td><td>0.2</td><td>0.4</td><td>0.1</td><td>0.3</td><td>0.1</td><td>0.9</td><td>-</td><td>0.2</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>86</td><td>Manoyl oxide</td><td>1976</td><td>2329</td><td>1990</td><td>2376</td><td>-</td><td>0.3</td><td>0.9</td><td>0.9</td><td>0.1</td><td>3.1</td><td>0.2</td><td>0.3</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>87</td><td>Abietatriene</td><td>2028</td><td>2478</td><td>2033</td><td>2506</td><td>0.4</td><td>0.6</td><td>0.3</td><td>0.3</td><td>0.9</td><td>1.5</td><td>0.1</td><td>0.5</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td>88</td><td>Abietadiene</td><td>2064</td><td>2441</td><td>2062</td><td>2450</td><td>0.4</td><td>0.7</td><td>0.3</td><td>0.5</td><td>0.9</td><td>5.4</td><td>0.2</td><td>1.8</td><td>RI, MS, <sup>13</sup>C NMR</td></tr><tr><td></td><td>Monoterpene hydrocarbons</td><td></td><td></td><td></td><td></td><td>80.1</td><td>68.6</td><td>81.5</td><td>73.9</td><td>74.9</td><td>36.2</td><td>83.9</td><td>71.1</td><td></td></tr><tr><td></td><td>Oxygenated monoterpenes</td><td></td><td></td><td></td><td></td><td>3.0</td><td>6.2</td><td>6.6</td><td>3.1</td><td>4.9</td><td>2.7</td><td>4.1</td><td>8.4</td><td></td></tr><tr><td></td><td>Sesquiterpene hydrocarbons</td><td></td><td></td><td></td><td></td><td>6.1</td><td>9.9</td><td>2.2</td><td>13.4</td><td>5.7</td><td>23.1</td><td>7.3</td><td>6.9</td><td></td></tr><tr><td></td><td>Oxygenated sesquiterpenes</td><td></td><td></td><td></td><td></td><td>2.8</td><td>7.7</td><td>2.3</td><td>3.4</td><td>4.3</td><td>11.3</td><td>2.3</td><td>3.6</td><td></td></tr><tr><td></td><td>Diterpene hydrocarbons</td><td></td><td></td><td></td><td></td><td>0.8</td><td>1.3</td><td>0.6</td><td>0.8</td><td>1.8</td><td>6.9</td><td>0.3</td><td>2.3</td><td></td></tr><tr><td></td><td>Oxygenated diterpenes</td><td></td><td></td><td></td><td></td><td>0.0</td><td>0.3</td><td>0.9</td><td>0.9</td><td>0.1</td><td>3.1</td><td>0.2</td><td>0.3</td><td></td></tr><tr><td></td><td>Others</td><td></td><td></td><td></td><td></td><td>2.4</td><td>2.4</td><td>2.6</td><td>2.0</td><td>4.4</td><td>1.1</td><td>1.4</td><td>3.5</td><td></td></tr><tr><td></td><td>Total (%)</td><td></td><td></td><td></td><td></td><td>95.2</td><td>96.4</td><td>96.7</td><td>97.5</td><td>96.1</td><td>84.4</td><td>99.5</td><td>96.1</td><td></td></tr></tbody></table>

[a] Components have been listed following their order of elution on apolar column (BP-1); Percentages on apolar column, except those with an asterisk, % on polar column (BP-20); [b] Rla, Rlp: Retention indices on apolar and polar columns, respectively; [c] RlaL, RlpL: Retention indices from literature, on apolar and polar columns, respectively; Babushok *et al.*, [33] otherwise stated; [d] Subsp. *oxycedrus*; [e] Subsp. *macrocarpa*; <sup>13</sup>C NMR: Compound identified by <sup>13</sup>C NMR, at least in one oil sample; nd: Not determined; Tr: Traces; [f] ref [34]; [g] Isomer not determined; [h] ref [35]; [i] ref [36]; [j] ref [29], [k] ref [37]; [l] ref [38]; [m] ref [39]; [n] ref [40]

Otherwise, regarding major components of group I, α-pinene was followed by germacrene D (M = 4.2%, SD 2.39).

Based on the contents of α-pinene, sabinene, δ-3-carene, β-phellandrene, terpinen-4-ol as well as 2-tridecanone, (Z)-6-pentadecen-2-one, abietadiene and manoyl oxide, the samples

of group II could be divided into two sub-groups, IIA and IIB (Figure 3, Table 3).

Sub-group IIA contained higher amount of α-pinene (M = 49.7%, SD7.27) than sub-group IIB (M = 27.3%, SD 7.89). Both sub-groups differed mainly by their contents of sabinene (1.0
<figure><img src="image_7.png" /><figcaption>**Figure 3.** Discriminant analysis scatterplot of the oil constituents of 37 LEO of two subspecies of *Juniperus oxycedrus*.</figcaption></figure>

vs. 8.7%), δ-3-carene (10.3 vs. 1.4%) and (Z)-6-pentadecen-2-one (1.7 vs. 4.9%).

It could be highlighted that all the samples from Aïn Fezza (S19-S28, *oxycedrus* subspecies) belonged to group I. The nine

samples from Ouled Mimoun (S1-S9, *oxycedrus* subspecies) were equally reparted between group I and sub-group IIA. The nine samples from Terny (S10-S18, *oxycedrus* subspecies) were reparted between group I and sub-group IIB, a last sample belonged to sub-group IIA. Lastly, the nine samples from Béni Saf, *macrocarpa* subspecies, are mainly found in group I (5 samples) beside sub-groups IIA (2 samples) and IIB (2 samples). The chemical variability appeared not related to the subspecies.

Comparing with previous results relative to the composition of *J. oxycedrus* leaf oil from Algeria, reported in the literature:

- an α-pinene-rich essential oil (92.2%) was reported from National Park of Djurdjura, Bouira (Northern Central Algeria). This composition is clearly related to group I (highest content in α-pinene) [17];

- an essential oil sample from Batna, (Northeastern Algeria) containing α-pinene, 56.1% may be associated to sub-group IIA, although it differed by a high content of β-phellandrene (17.9%) [11];

- a composition from Tébessa, East Algeria with α-pinene 42.2% may be also associated to group IIA, although it differed by a high content of abietadiene (7.3%) [12];

- an oil sample from Laghouat (Central North Algeria) displayed a content of α-pinene (37.6%) similar to those of

<table><caption>**Table 3.** Chemical variability of *Juniperus oxycedrus* LEO.</caption><thead><tr><th rowspan="2">Groups/samples<br>Sub-groups/samples</th><th colspan="4">Group I/24</th><th colspan="4">Group II/13<br>IIA/8</th><th colspan="4">IIB/5</th></tr><tr><th>M<sup>[b]</sup></th><th>SD<sup>[c]</sup></th><th>Min<sup>[d]</sup></th><th>Max<sup>[e]</sup></th><th>M<sup>[b]</sup></th><th>SD<sup>[c]</sup></th><th>Min<sup>[d]</sup></th><th>Max<sup>[e]</sup></th><th>M<sup>[b]</sup></th><th>SD<sup>[c]</sup></th><th>Min<sup>[d]</sup></th><th>Max<sup>[e]</sup></th></tr></thead><tbody><tr><td>Components<sup>[a]</sup></td><td></td><td></td><td></td><td></td><td></td><td></td><td></td><td></td><td></td><td></td><td></td><td></td></tr><tr><td>α-Thujene</td><td>0.2</td><td>0.34</td><td>Tr</td><td>0.9</td><td>0.2</td><td>0.26</td><td>Tr</td><td>0.7</td><td>1.5</td><td>2.04</td><td>0.0</td><td>4.1</td></tr><tr><td>α-Pinene</td><td>69.2</td><td>6.24</td><td>57.4</td><td>80.9</td><td>49.7</td><td>7.27</td><td>39.4</td><td>61.7</td><td>27.3</td><td>7.89</td><td>14.3</td><td>35.4</td></tr><tr><td>Oct-1-en-3-ol</td><td>0.2</td><td>0.14</td><td>0.0</td><td>0.5</td><td>0.8</td><td>0.59</td><td>0.1</td><td>2.0</td><td>0.3</td><td>0.17</td><td>0.2</td><td>0.6</td></tr><tr><td>Sabinene</td><td>0.9</td><td>1.40</td><td>0.2</td><td>5.3</td><td>1.0</td><td>1.52</td><td>0.1</td><td>3.5</td><td>8.7</td><td>11.94</td><td>0.1</td><td>25.2</td></tr><tr><td>β-Pinene</td><td>1.6</td><td>0.42</td><td>0.9</td><td>2.4</td><td>1.7</td><td>0.98</td><td>1.2</td><td>4.1</td><td>0.9</td><td>0.10</td><td>0.8</td><td>1.1</td></tr><tr><td>Myrcene</td><td>1.9</td><td>1.33</td><td>0.7</td><td>7.8</td><td>1.9</td><td>0.83</td><td>1.1</td><td>3.7</td><td>1.3</td><td>0.74</td><td>0.7</td><td>2.4</td></tr><tr><td>δ-3-Carene</td><td>0.9</td><td>2.32</td><td>0.0</td><td>9.3</td><td>10.3</td><td>4.69</td><td>Tr</td><td>14.6</td><td>1.4</td><td>1.06</td><td>0.3</td><td>3.0</td></tr><tr><td>α-Terpinene</td><td>0.1</td><td>0.18</td><td>0.0</td><td>0.7</td><td>0.1</td><td>0.11</td><td>0.0</td><td>0.3</td><td>0.7</td><td>0.99</td><td>Tr</td><td>2.2</td></tr><tr><td>p-Cymene</td><td>0.5</td><td>0.41</td><td>0.1</td><td>1.6</td><td>1.5</td><td>1.00</td><td>0.1</td><td>3.1</td><td>2.8</td><td>2.82</td><td>0.6</td><td>4.6</td></tr><tr><td>Limonene</td><td>1.0</td><td>0.35</td><td>Tr</td><td>1.7</td><td>1.2</td><td>0.44</td><td>0.9</td><td>1.9</td><td>1.8</td><td>1.41</td><td>0.5</td><td>3.4</td></tr><tr><td>β-Phellandrene</td><td>1.2</td><td>1.73</td><td>0.1</td><td>6.3</td><td>3.3</td><td>3.72</td><td>0.1</td><td>11.0</td><td>1.1</td><td>0.02</td><td>0.4</td><td>2.8</td></tr><tr><td>γ-Terpinene</td><td>0.2</td><td>0.35</td><td>0.0</td><td>1.3</td><td>0.1</td><td>0.18</td><td>0.0</td><td>0.5</td><td>1.6</td><td>2.10</td><td>0.0</td><td>4.3</td></tr><tr><td>Terpinen-4-ol</td><td>0.5</td><td>0.78</td><td>Tr</td><td>2.8</td><td>0.6</td><td>1.00</td><td>Tr</td><td>2.6</td><td>4.2</td><td>5.42</td><td>0.2</td><td>11.6</td></tr><tr><td>Germacrene D</td><td>4.2</td><td>2.39</td><td>Tr</td><td>10.2</td><td>3.3</td><td>3.38</td><td>0.4</td><td>11.1</td><td>4.9</td><td>6.15</td><td>0.9</td><td>15.7</td></tr><tr><td>2-Tridecanone</td><td>0.2</td><td>0.18</td><td>0.0</td><td>0.6</td><td>0.3</td><td>0.20</td><td>0.0</td><td>0.6</td><td>1.4</td><td>1.58</td><td>0.0</td><td>3.7</td></tr><tr><td>γ-Cadinene</td><td>0.6</td><td>0.46</td><td>0.1</td><td>1.8</td><td>0.8</td><td>0.62</td><td>0.2</td><td>1.9</td><td>0.9</td><td>0.97</td><td>0.1</td><td>2.4</td></tr><tr><td>(E)-Nerolidol</td><td>Tr</td><td>0.01</td><td>0.0</td><td>Tr</td><td>0.5</td><td>1.30</td><td>0.0</td><td>3.7</td><td>0.0</td><td>0.01</td><td>0.0</td><td>Tr</td></tr><tr><td>(Z)-6-Pentadecen-2-one</td><td>1.1</td><td>0.76</td><td>0.1</td><td>2.8</td><td>1.7</td><td>0.93</td><td>0.5</td><td>2.9</td><td>4.9</td><td>6.09</td><td>0.1</td><td>12.0</td></tr><tr><td>2,3-Dihydrofarnesol</td><td>0.3</td><td>0.24</td><td>0.0</td><td>1.1</td><td>0.5</td><td>0.36</td><td>0.2</td><td>1.2</td><td>1.5</td><td>1.48</td><td>0.1</td><td>3.6</td></tr><tr><td>(2E,6E)-Farnesol</td><td>0.8</td><td>0.66</td><td>Tr</td><td>2.5</td><td>0.7</td><td>0.46</td><td>0.2</td><td>1.7</td><td>1.9</td><td>0.73</td><td>1.1</td><td>2.7</td></tr><tr><td>Manoyl oxide</td><td>0.3</td><td>0.32</td><td>0.0</td><td>1.0</td><td>0.5</td><td>0.25</td><td>0.1</td><td>0.9</td><td>2.2</td><td>0.80</td><td>0.9</td><td>3.1</td></tr><tr><td>Abietadiene</td><td>0.5</td><td>0.43</td><td>0.0</td><td>1.9</td><td>1.0</td><td>0.81</td><td>0.1</td><td>2.5</td><td>2.4</td><td>2.06</td><td>0.7</td><td>5.4</td></tr></tbody></table>

[a] Percentages are given on apolar column (BP-1); [b] Mean (M); [c] Standard deviation (SD); [d] Minimum content (Min); [e] Maximum content (Max); Tr: Traces.
some oil samples of sub-group IIA, however with higher
content of abietadiene (8.3%) and bulnesol (7.2%, scarcely
reported in *J. oxycedrus* essential oils)[13];

- In parallel, a sample from Bouira (Central Algeria) contained α-pinene (36.7%) and it belongs to sub-group IIA, taking into account the appreciable content of δ-3-carene (10.6%)[19];

- Most in the South, at Founassa, near Aïn Sefra, an essential oil sample contained fair amount of α-pinene (33.4%). However, the high content of germacrene D (23.7%) differentiated this sample from ours of sub-group IIB[20];

- A first sample from Mostaganem (Northwestern Algeria), that contained α-pinene as major component (23.6%), followed with sabinene (10.8%) may be associated to sub-group IIB, although it contained fair amounts of farnesol (8.5%) and epi-manoyl oxide (11.5%), reported for the first time in *J. oxycedrus* essential oils[14];

- Another sample from Mostaganem, containing similar amounts of α-pinene (14.9%) and sabinene (14.9%) could be also associated to sub-group IIB, however, it differed by the content of terpinen-4-ol (17.5%)[21];

Lastly, the compositions of two other Algerian *J. oxycedrus*
oil samples look atypical with respect to those observed in
Tlemcen and Aïn Témouchent provinces, reported here and
they cannot be introduced in any of the groups and sub-
groups. For instance, the composition of an oil sample from
Tiaret Forest (Northwestern Algeria), was dominated by germa-
crene D (27.4%), δ-3-carene (24.7%), accompanied by myrcene
(13.9%) beside α-pinene (4.1%).[22] A sample from Tébessa
(Eastern Algeria) contained mainly oxygenated pinane deriva-
tives, *trans*-pinocarveol (7.0%), *cis*-verbenol (6.3%), pinocarvone
(5.1%), verbenone (3.6%) while α-pinene accounted for 0.2%
only.[23]

Concerning leaf oils from the subspecies macrocarpa, they
could not associate with our groups and sub-groups. Indeed,
the first one from El Kala, contained mainly germacrene D
(21.3%), (Z,Z)-farnesol (10.9%) and 8,13-epoxy-14,15-dinorlab-
dane (8.8%).[26] The second sample from Oum El Bouaghi,
exhibited a very unusual composition dominated by (Z)-5-
tetradecen-1-yl acetate (12.9%) and γ-muurolene (9.1%).[9]

Comparing the present results with previous studies that
included statistical analysis, the compositions of essential oil
samples from group I (α-pinene M=69.2%, SD 6.24) and sub-
group IIA (α-pinene M=49.7%, SD 7.27) resembled to those of
essential oils from Corsica (subspecies *oxycedrus*) with α-pinene
M=73.3%, SD 5.8 (group I) and M=56.1%, SD 5.7 (group II).[29]
Otherwise, we noticed that the nine samples from Béni Saf,
*macrocarpa* subspecies, are present in the three groups and
sub-groups. Similarly, the chemical compositions of 18 leaf oil
samples of *J. oxycedrus* ssp. *macrocarpa* from Corsica, varied
substantially from sample to sample.[30]

Regarding the compositions of essential oils isolated from
individual trees growing in Tunisia, α-pinene was always the
major component although its content varied substantially
(24.32–58.03%) as observed in the present study (14.3–80.9%).
α-Pinene was accompanied by various compounds not present
in our samples, β-bourbonene (up to 14.28%), 10-epi-α-
muurolol (up to 11.13%), geranyl acetone (up to 8.80%), 13-

epi-manoyl oxide (up to 6.95%). Four groups were distin-
guished, however, the mean value of every component in each
group was not given.[27]

The essential oil samples of *J. oxycedrus* collected among 20 populations across Bulgaria contained various components with low to medium content: α-pinene (6.5–24.8%, much lower content than in our samples), manoyl oxide (4.9–18.4%), limonene (1.8–16.7%), caryophyllene oxide (0.7–13.2%), β-caryophyllene (0.1–12.5%), δ-cadinene (0.4–11.9%), germacrene D (0.0–11.7%). Samples were grouped in eight chemotypes (however, the mean percentage of every compound with respect to the chemotype, was not given).[28]

Conclusions

Thirty-seven essential oil samples have been isolated from
leaves of *J. oxycedrus* (subspecies *oxycedrus* and *macrocarpa*)
growing wild in Tlemcen and Aïn Témouchent provinces
(Northwestern Algeria). Analysis by combination of chromatо-
graphic and spectroscopic techniques of eight selected oil
samples allowed the identification of 88 components that
accounted for 84.4–99.5% of the whole compositions. α-Pinene
was the major component although its percentage varied
substantially. The 37 compositions were subjected to statistical
analysis which suggested the existence of two principal groups
I and II, one of these being subdivided into two sub-groups IIA
and IIB. Group I, the most important group with 24 oil samples
out of 37, differed from sub-groups IIA and IIB, essentially by
the high content of α-pinene (mean value, 69.2%; SD 6.24).
Sub-groups IIA and IIB were differentiated by their content of
α-pinene (Mean values, 49.7% and 27.3%, respectively) as well as
δ-3-carene (10.3%, sub-group IIA) and sabinene (8.7%, sub
group IIB). The fair content of (Z)-6-pentadecen-2-one in sub-
group IIB (Mean value 4.9%) could be noticed. The composi-
tions of *J. oxycedrus* essential oils from Algeria, previously
reported, were discussed with respect to groups and sub-
groups of the present study.

**Experimental Part**

**Plant Material**

Leaves from 37 individual plants of two subspecies of *Juniperus oxycedrus* were collected during December 2018 to March 2019 in two localities of Northwestern of Algeria (Figure 1). Twenty-eight samples of *J. oxycedrus* subsp. *oxycedrus* were sampled at Tlemcen province (Ouled Mimoun: S1-S9; Terny: S10-S18; Aïn Fezza: S19-S28) and nine samples of *J. oxycedrus* subsp. *macrocarpa* were collected at Aïn Témouchent province (Béni Saf: S29-S37).

Identification of the plants was performed by Dr. B. Babali and Prof. F. Hassani (Laboratory of Ecology and Management of Natural Ecosystems, University of Tlemcen, Algeria). A voucher specimen has been deposited at the Laboratory of Natural Products (Department of Biology, University of Tlemcen) under the accession N°C. 48.
<figure><img src="image_8.png" /></figure>

## Essential Oil Distillation

The leaves were dried for a week, in the shade, and then submitted (452–546 g) to hydrodistillation for 2 h using a Clevenger-type apparatus. Yields have been calculated from dry material (w/w).

## Analytical GC

GC analyses were performed on a Perkin-Elmer Clarus 500 gas chromatograph (FID) equipped two fused silica capillary columns (50 m×0.22 mm, 0.25 µm film thickness), BP-1 (polydimethyl siloxane) and BP-20 (polyethylene glycol). The oven temperature was programmed from 60°C to 220°C at 2°C/min and then held isothermal at 220°C for 20 min, injector temperature: 250°C; detector temperature: 250°C; carrier gas: hydrogen (1.0 mL/min); split: 1/60.

The relative proportions of the oil constituents were expressed as percentages obtained by peak area normalization, without using correcting factors. Retention indices (RI) were determined relative to the retention times of a series of *n*-alkanes with linear interpolation ("Target Compounds" software from Perkin-Elmer).

## GC/MS Analysis

The essential oils were analyzed with a Perkin-Elmer TurboMass detector (quadrupole), directly coupled to a Perkin-Elmer Autosystem XL, equipped with a fused-silica capillary column (50 m×0.22 mm i.d., film thickness 0.25 µm), BP-1 (dimethylpolysiloxane). Carrier gas, helium at 0.8 mL/min; split, 1/60; injection volume, 0.5 µL; injector temperature, 250°C; oven temperature programmed from 60°C to 220°C at 2°C/min and then held isothermal (20 min); Ion source temperature, 250°C; energy ionization, 70 eV; electron ionization mass spectra were acquired over the mass range 40–400 Da.

## ¹³C NMR Analyses

¹³C NMR analysis was performed on a Bruker AVANCE 400 Fourier Transform spectrometer operating at 100.623 MHz for ¹³C, equipped with a 5 mm probe, in deuterated chloroform (CDCl₃), with all shifts referred to internal tetramethylsilane (TMS). ¹³C NMR spectra were recorded with the following parameters: pulse width (PW), 4 µs (flip angle 45°); acquisition time, 2.73 s for 128 K data table with a spectral width (SW) of 220 000 Hz (220 ppm); CPD mode decoupling; digital resolution 0.183 Hz/pt. The number of accumulated scans ranged 2 000–3 000 for each sample (around 40 mg of oil in 0.5 mL of CDCl₃). Exponential line broadening multiplication (1.0 Hz) of the free induction decay was applied before Fourier Transform.

## Identification of Components

Identification of the components was based on:

- comparison of their GC retention indices (RI) on polar and apolar columns, determined relative to the retention times of a series of *n*-alkanes with linear interpolation (Target Compounds software of Perkin-Elmer), with those of authentic compounds and with reference data[³³];

- computer matching against commercial mass spectral libraries[⁴¹⁻⁴³];

- comparison of the signals in the ¹³C NMR spectra of essential oils with those of reference spectra compiled in the laboratory spectral library, with the help of a laboratory-made

software.[³¹,³²,⁴⁴] In the investigated samples individual components were identified by NMR at contents as low as 0.4–0.5%.

## Data Analysis

Principal Components Analysis (PCA) and Hierarchical clustering (Ward's method) were performed by Xlstat (Adinsoft, France).[⁴⁵]

## Author Contributions

Conceptualization: C.B., J.C. and F.T.; methodology: C.B. and F.T., sampling and extraction: C.E.W.M. and K.S. plant identification: B.B.; investigation: formal analysis, C.B. and M.P.; original draft preparation: C.B., J.C. and F.T., writing review: C.B. and J.C.

## Acknowledgements

The authors gratefully acknowledge Prof. S. Ghalem and H. Allali (Laboratory of Natural and Bioactive Substances, University of Tlemcen), for their help in the extraction of essential oils.

## Conflict of Interests

The authors declare no conflict of interest.

## Data Availability Statement

The data that support the findings of this study are available from the corresponding author upon reasonable request.

**Keywords:** *Juniperus oxycedrus* · Northwestern Algeria · Leaf essential oil · Chemical composition · Statistical analysis

[1] P. Quézel, F. Médail, 'Nouvelle flore de l'Algérie et des régions désertiques méridionales', Edition CNRS, Tome II, Paris, France, 1962, 1169.

[2] A. Dobignard, C. Chatelain, 'Index synonymique de la flore d'Afrique du nord: Pteridophyta, Gymnospermae, Monocotyledoneae', éditions des conservatoire et jardinbotaniques, Vol. 1, Genève, Suisse, 2010, 455.

[3] A. Farjon, 'A Handbook of the World's Conifers', Koninklijke Brill NV, Leiden, Vol. 2, Boston, The Netherlands, 2010.

[4] IUCN, 'A guide to medicinal plants in North Africa', IUCN Centre for Mediterranean cooperation Editor, Malaga, Spain, 2005, 256 p.

[5] J. Bellakhdar, 'La pharmacopée marocaine traditionnelle: Médecine arabe ancienne et savoirs populaires', Ibis Press, Eds. Le Fennec, Paris, France, 1997, 764.

[6] L. El Rhaffari, A. Zaid, 'Pratique de la phytothérapie dans le sud-est du Maroc (Tafilalet): Un savoir empirique pour une pharmacopée rénovée', Proceedings of the 4th European Congress on Ethnopharmacology, "From the sources of knowledge to the medicines of the future", Metz (France), 2000/05/11-13, IRD Editions, 2002, 468 p. ISBN 2-7099-1504-9.

[7] A. Boudjelal, C. Henchiri, M. Sari, D. Sarri, N. Hendel, A. Benkhaled, G. Ruberto, *J. Ethnopharmacol.* **2013**, *148*(2), 395–402

[8] S. Menad, D. Achour, M. Brada, *Int. J. Biosci.* **2018**, *13*, 98–103.

[9] N. Basa, H. Djebaili, M. Mokrani, M. M. Senoussi, S. Boulehbal, A. Zellagui, *J. Pharm. Res. Int.* **2022**, *34*, 1–7.

[10] A. H. A. Boukhaloua, M. Berrayah, F. Bennabi, A. Ayache, F. Abdeldjebar, *Ukr. J. Ecol.* **2022**, *12*, 31–39.
[11] A. Zatout, R. Djibaoui, G. Flamini, R. Ascrizzi, C. Benbrahim, H. E. Mazari, F. Benkredda, S. Mechaala, A. Kassah-Laouar, *Afr. J. Clin. Exper. Microbiol.* **2022**, *23*, 278–289.

[12] S. Boudiba, A. Ngenge Tamfu, B. Berka, K. Hanini, S. Hioun, K. Allaf, L. Boudiba *Nat. Prod. Commun.* **2021**, *16*, 1–11.

[13] K. Cheraif, B. Bakchiche, A. Gherib, S. K. Bardaweel, M. Çol Ayvaz, G. Flamini, R. Ascrizzi, M. A. Ghareeb, *Molecules* **2020**, *25*, 1710.

[14] S. Menad, D. Achour, M. Brada, *South Asian J. Exp. Biol.* **2022**, *12*, 492–498.

[15] C. Zahaf, D. Achour, M. Mokhtar, M. Brada, *South Asian J. Exp. Biol.* **2017**, *7*, 74–83.

[16] F. Bachiri, F. Benouaklil, F. Hamaidi-Chergui, F. Saidi, *J. Essent. Oil-Bear. Plants* **2022**, *25*, 1–10.

[17] Y. Foudil-Cherif, N. Yassaa, *Food Chem.* **2012**, *135*, 1796–1800.

[18] M. Boussaïd, C. Bekhechi, A. Bouayed, F. Hassani, J. Casanova, M. Paoli, F. Tomi, *Chem. Biodiversity*, **2024**, *21*, e202400862 Doi: 10.1002/cbdv.202400862.

[19] D. Dahmane, T. Dob, C. Chelghoum, *J. Mater. Environ. Sci.* **2015**, *6*, 3159–3167.

[20] A. Bouyahyaoui, ‘Contribution à la valorisation des substances naturelles: Etude des huiles essentielles des Cupressacées de la région de l’Atlas algérien’, *Thèse de doctorat en Sciences, Filière: Biologie, Option: Microbiologie*, 2017, Université Abdelhamid Ibn Badis de Mostaganem, Algeria.

[21] S. Menad, D. Achour, M. Brada, *Int. J. Biosci.* **2018**, *13*, 98–103.

[22] S. Guerroudj, M. Maatoug, K. Naceur, R. Chaibi, M. Khene, A. Boualem, *Ukr. J. Ecol.* **2021**, *11*, 105–111.

[23] T. Dob, D. Dahmane, C. Chelghoum, *Pharm. Biol.* **2006**, *44*, 1–6.

[24] A. H. A. Boukhaloua, M. Berrayah, F. Bennabi, A. Ayache, F. Abdeldjebar, *Ukr. J. Ecol.* **2022**, *12*, 31–39.

[25] H. Fadel, F. Benayache, J. C. Chalchat, G. Figueredo, P. Chalard, H. Hazmoune, S. Benayache, *Nat Prod. Res.* **2021**, *35*, 2616–2620 https://doi.org/10.1080/14786419.2019.1687473.

[26] H. Djebaili, A. Zellagui, N. Gherraf, *J. Nat. Prod. Plant Resour.* **2013**, *3*, 40–44.

[27] H. Medini, A. Elaissi, M. L. Khouja, I. Chraief, F. Farhat, M. Hammami, R. Chemli, F. Harzallah-Skhiri, *Chem. Biodiversity* **2010**, *7*, 1250–1266.

[28] I. B. Semerjieva, V. D. Zheljazkov, I. Dincheva, T. Astatkie, M. Kačániová, *Ind. Crops Prod.* **2020**, *158*, 113005.

[29] J. B. Boti, A. Bighelli, C. Cavaleiro, L. Salgueiro, J. Casanova, *Flavour Fragr. J.* **2006**, *21*, 268–273.

[30] J. Ottavioli, A. Bighelli, J. Casanova, F. Tomi, *Nat. Prod. Commun.* **2018**, *13*, 213–216.

[31] F. Tomi, P. Bradesi, A. Bighelli, J. Casanova, *J. Magn. Reson. Anal.* **1995**, *1*, 25–34.

[32] Z. A. Ouattara, J. B. Boti, A. C. Ahibo, S. Sutour, J. Casanova, F. Tomi, A. Bighelli, *Flavour Fragr. J.* **2014**, *29*, 371–379.

[33] V. I. Babushok, P. J. Linstrom, I. G. Zenkevich, *J. Phys. Chem. Ref. Data.* **2011**, *40*(043101), 1–47.

[34] P. Salehi, A. Sonboli, F. Eftekhar, S. Nejad-Ebrahimi, M. Yousef Zadi, *Biol. Pharm. Bull* **2005**, *28*,1892–1896.

[35] K. H. C. Baser, G. Özek, T. Özek, A. Duran, H. Duman, *Flavour Fragr. J.* **2006**, *21*, 650–655.

[36] P. Weyerstahl, H. Marchall, U. Splittgerber, D. Wolf, *Flavour Fragr. J.* **2000**, *15*, 153–173.

[37] J. A. Pino, R. Marbot, *J. Agric. Food Chem.* **2001**, *49*(12), 5880–5882.

[38] J. Leдаuphin, J. F. Saint-Clair, O. Lablanquie, H. Guichard, N. Founier, E. Guichard, D. Barillier, *J. Agric. Food Chem.* **2004**, *52*, 5124–5134.

[39] M. Gonny, P. Bradesi, J. Casanova, *Flavour Fragr. J.* **2004**, *19*, 424–433.

[40] M. Gonny, C. Cavaleiro, L. Salgueiro, J. Casanova, *Flavour Fragr. J.* **2006**, *21*, 99–106.

[41] W. A. Konig, D. H. Hochmuth, D. Joulain, ‘Terpenoids and Related Constituents of Essential Oils’, Library of Mass Finder 2.1, Institute of Organic Chemistry, Hamburg, **2001**.

[42] R. P. Adams, ‘Identification of Essential Oils Components by Gas Chromatography/Mass Spectroscopy’, **2017**, ed. 4.1, 30 Jan. 2017, ISBN 978-1-932633-21-4.

[43] National Institute of Standards and Technology, PC Version of the NIST/EPA/NIH Mass Spectral Library; NIST: Gaithersburg, MD, USA, **2008**.

[44] O. Bazzali, T. H. Thai, T. M. Hoi, N. S. Khang, N. T. Hien, J. Casanova, A. Bighelli, F. Tomi, *Molecules*, **2016**, *21*, 840–851.

[45] P. Legendre, L. Legendre, ‘Numerical Ecology’, 2nd Edn, Elsevier Science, Amsterdam, **1998**.