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Article

Caryophyllene-Rich Essential Oils of Two Species from Southern Côte d’Ivoire: Guibourtia ehie (A. Chev.) J Léonard (Caesalpiniaceae) and Oricia suaveolens (Engl.) Verd. (Rutaceae)

1
Laboratoire de Chimie Bio-Organique et de Substances Naturelles, Université Nangui Abrogoua, Abidjan 02 BP 801, Côte d’Ivoire
2
UPR de Chimie Organique, Département de Mathématiques-Physique-Chimie, Université Péléforo GON COULIBALY, Korhogo BP 1328, Côte d’Ivoire
3
Laboratoire Sciences Pour l’Environnement, Université de Corse—CNRS, UMR 6134 SPE, Route des Sanguinaires, 20000 Ajaccio, France
*
Author to whom correspondence should be addressed.
Compounds 2023, 3(1), 73-82; https://doi.org/10.3390/compounds3010006
Submission received: 16 December 2022 / Revised: 6 January 2023 / Accepted: 10 January 2023 / Published: 12 January 2023

Abstract

:
The essential oils of Oricia suaveolens and Guibourtia ehie from Southern Côte d’Ivoire were extracted by hydrodistillation then analyzed by gas chromatography in combination with retention indices [GC(RI)], gas chromatography coupled with mass spectrometry (GC-MS) and nuclear magnetic resonance of carbone-13 (13C NMR) And described here for the first time. A total of 42 compounds were identified in the essential oils of the leaves of G. ehie while 55, 40 and 23 components were identified in the leaves, stem bark and root bark oils of O. suaveolens, respectively. Essential oils samples were dominated by sesquiterpenes and (E)-β-caryophyllene was the major compound common to all samples: G. ehie leaf oil contained (E)-β-caryophyllene (26.9–40.8%), α-humulene (syn. α-caryophyllene) (6.7–9.7%), β-elemene (5.5–9.5%) and germacrene D (5.6–8.1%); O. suaveolens, leaf oil contained (E)-β-caryophyllene (33.5–39.3%), (E)-β-farnesene (5.9–9,3%), caryophyllene oxide (2.1–7.7%) and α-humulene (4.0–4.6%); stem bark oil contained α-humulene (38.3–45.8%) and (E)-β-caryophyllene (34.7–41.6%); root bark oil contained α-humulene (36.1–47.9%) and (E)-β-caryophyllene (34.3–43.3%). This study highlighted the abundant presence of (E)-β-caryophyllene, a phytocannabinoïd sesquiterpene with countless biological properties, in two plant species: Guibourtia ehie and Oricia suaveolens.

1. Introduction

Guibourtia ehie (A. Chev.) J Léonard and Oricia suaveolens (Engl) are two plant-species growing wild in Côte d’Ivoire.
G. ehie is a tree of the Cesalpiniaceae (Fabaceae) family up to 45–50 m tall, with a straight, cylindrical bole, branchless for up to 25 m. The leaves are spirally arranged, pari-pinnate with a pair of leaflets; the stipules are leaf-like, up to 2 cm long, and often persistent; the petioles are 0.5–1 cm long. The distribution area of G. ehie extends from Guinea and Liberia to Cameroon and Gabon [1,2]. It is a medicinal plant present in Cameroon, Ghana, Liberia, Nigeria and Côte d’Ivoire [3]. It is used for the treatment of gonorrhea wounds [3], ulcers [4], high blood pressure and sexual infections [5]. Very few works in the literature deal with the phytochemistry of the Guibourtia genus. The phytochemical screening made from solvent extracts of G. ehie highlighted the presence of terpenes, sterols, saponins, flavonoids and alkaloids [4]. A dihydrochalcone glucoside, 2′,4-dihydroxy-4′-methoxy-6′-O-β-glucopyranoside dihydro-chalcone, a stilbene glycoside, 3,5-dimethoxy-4′-O-(β-rhamnopyranosyl-(1→6)-β-gluco-pyranoside) stilbene, and pterostilbene were isolated from G. tessmanii [6]. The leaves and trunk of G. ehie contained rhaponticine, 2,6-dimethoxybenzoquinone, lupeol, taraxerol, friedelan-3-one, lanosterol, scopoletine and pilloine [5]. Antioxidant and antibacterial activities are attributed to this plant [3,4,5]. However, no study concerning the chemical composition of the essential oils of G. ehie was mentioned in the literature.
Oricia suaveolens (Rutaceae) is a shrub or tree up to 10 m long. Its leaves are trifoliate, rarely simple, with a long petiole [7]. It is a species used in traditional medicine against toothache, fever and parasites [5]. The literature reports few studies on the phytochemicals identified in the Oricia genus. A furoquinoline alkaloid, 6,7-methylenedioxy-5-hydroxy-8-ethoxy-dictamine, and a flavanone glycoside, 5-hydroxy-4′-methoxy-7-O-[α-l-rhamnopyranosyl (1”→5”)-β-d-apiofuranosyl]-flavanoside, were isolated from O. suaveolens and O. renieri [8]. The root of O. suaveolens contained mainly alkaloids including skimmianine, kokusaginine and montrifoline and triterpenes such as limonine [9], while the leaves and stem contained β-indoloquinazoline alkaloids; orisuaveoline A, orisuaveoline B and furoquinoline alkaloids; quinosuaveoline A, and quinosuaveoline B [10]. No study reports the chemical composition of the essential oil of O. suaveolens.
In the course of our on-going work on the characterization of the aromatic plants of Côte d’Ivoire through the chemical composition of their essential oils [11,12,13,14], the aim of the present work was to i) determine, for the first time, the chemical composition of the essential oil from G. ehie and O. suaveolens, growing wild in Côte d’Ivoire, and ii) highlight the presence of (E)-β-caryophyllene as a major component.
In recent years, many studies have demonstrated the interesting biological properties of (E)-β-caryophyllene: antinociceptive and anti-inflammatory [15]; anticancer [16,17]; antioxidant [16,18]; antimicrobial [16]; analgesic [17]; and antiatherogenic [18]. Essential oils rich in caryophyllene therefore present a particular interest. Previous studies have shown the occurrence of (E)-β-caryophyllene in Ivorian plant species [14,19,20,21,22].

2. Materials and Methods

2.1. Plant Material

Four leaves samples of G. ehie were harvested in Boua M’po, Rubino, Côte d’Ivoire (G1, G2) (6°04′09″ N, 4°18′31″ W) and in Adiopodoumé, Abidjan, Côte d’Ivoire (G3, G4) (5°20’12” N et 4°7’57” W). The plant was authenticated (voucher n° IBAAN REG 00704) in “Centre National de Floristique”, Université Félix Houphouët-Boigny, Abidjan.
Three samples of leaves, four samples of stem bark and five samples of root bark of O. suaveolens were harvested in Petit Yapo Forest (5°43’50.5” N, 4°4’41.9” W), Agboville, Côte d’Ivoire. The organs were conditioned under permanent air conditioning for three days at 18 °C. The identification of the plant has been confirmed (voucher n° LAA 10096) by “Centre National de Floristique”, Université Félix Houphouët-Boigny, Abidjan.

2.2. Essential Oil Isolation

Vegetable material was submitted to hydrodistillation during 3.5 h with a Clevenger-type apparatus. The essential oil samples obtained were dried over anhydrous Na2SO4 and then conserved at 5 °C. The extraction yields were calculated from fresh material (w/w) (Table S1).

2.3. Gas Chromatography and Gas Chromatography–Mass Spectrometry in Electron Impact Mode

GC analyses were performed on a Clarus 500 PerkinElmer Chromatograph (PerkinElmer, Courtaboeuf, France), equipped with a flame ionization detector (FID) and two fused-silica capillary columns (50 m × 0.22 mm, film thickness 0.25 µm), BP-1 (polydimethylsiloxane) 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 (0.8 mL/min); split: 1/60; injected volume: 0.5 µL. Retention indices (RI) were calculated relative to the retention times of a series of n-alkanes (C8–C29) with linear interpolation (« Target Compounds » software from PerkinElmer).
GC/MS analyses were performed on a Clarus SQ8S PerkinElmer TurboMass detector (quadrupole), directly coupled with a Clarus 580 PerkinElmer Autosystem XL (PerkinElmer, Courtaboeuf, France), equipped with a BP-1 (polydimethylsiloxane) fused-silica capillary column (50 m × 0.22 mm i.d., film thickness 0.25 µm). The oven temperature was programmed from 60 to 220 °C at 2°/min and then held isothermal for 20 min; injector temperature, 250 °C; ion-source temperature, 250 °C; carrier gas, Helium (1 mL/min); split ratio, 1:80; injection volume, 0.5 µL; ionization energy, 70 eV. The electron ionization (EI) mass spectra were acquired over the mass range 35–350 Da.

2.4. Nuclear Magnetic Resonance

All nuclear magnetic resonance (NMR) spectra were recorded on a Bruker AVANCE 400 Fourier transform spectrometer (Bruker, Wissembourg, France) operating at 100.623 MHz for 13C, equipped with a 5 mm probe. Solvent used was CDCl3, with all shifts referred to internal tetramethylsilane (TMS). 13C NMR spectra of the oil samples were recorded with the following parameters: pulse width, 4 µs (flip angle 45°); relaxation delay D1, 0.1 s; acquisition time, 2.7 s for a 128K data table with a spectral width of 25,000 Hz (250 ppm); CPD mode decoupling; digital resolution, 0.183 Hz/pt. The number of accumulated scans was 3000 for each sample or fraction (30 mg, in 0.5 mL of CDCl3).

2.5. Identification of Individual Components

Identification of the individual components was carried out as follows: (i) by comparison of their GC retention indices on apolar and polar columns, with those of reference compounds [23,24]; (ii) on computer matching against commercial mass spectral libraries [24,25,26]; (iii) on comparison of the signals in the 13C NMR spectra of the samples with those of reference spectra compiled in the laboratory spectral library, with the help of laboratory-made software [27,28,29]. This method allowed the identification of individual components of the essential oil at content as low as 0.4–0.5%.

3. Results and Discussion

Four essential oils samples of the leaves of G. ehie harvested in two locations in the south of Côte d’Ivoire (Boua M’po and Adiopodoumé), were obtained with low yield (0.01–0.05 %: w/w; calculated on weight basis) (Table S1)
Essential oils of the leaves (three samples), stem bark (four samples) and root bark (five samples) of O. suaveolens harvested in Petit Yapo Forest were obtained with low yields (Table S1) (0.05–0.08%, 0.01–0.03% and 0.01–0.02%: w/w, calculated on weight basis, respectively).
A combination of techniques was applied to the essential oil analysis: GC (associated with retention indices on two columns with different polarity), GC-MS and 13C NMR following a computerized 13C NMR method developed at the University of Corsica [11,29]. Most compounds have been identified through these three techniques.

3.1. Chemical Composition of Leaf Oils of G. ehie

Forty-two compounds were identified in the leaf oil of G. ehie representing 89.9 to 93.8% of the overall composition (Table 1). The chemical compositions of the four oils were dominated by sesquiterpene hydrocarbons; among them, (E)-β-caryophyllene (26.9–40.8%) was the major compound. Other compounds were present in appreciable amounts: β-elemene (5.5–9.5%), α-humulene (6.7–9.7%), germacrene D (5.6–8.1%) and β-elemol (1.6–4.2%). No monoterpene was identified and the total amount of non-terpene linear compounds (0.9–2.9%) and diterpenes (0.5–3.3%) was limited.
The chemical composition of the four oil samples was homogenous and no chemical variability was observed in relation to the location. However, sample G4 was slightly different and exhibited a low amount of (E)-caryophyllene (26.9%) in comparison to the G1-G3 samples whose content is higher than 40%. (E)-Caryophyllene, the main compound of the essential oils of the leaves of G. ehie, is also found as the main component in various species belonging to the same family (Caesalpiniaceae): Copaifera multijuga, 36% [30]; 57.5% [31]; Indigofra microcarpa, 56% [32].

3.2. Chemical Composition of Leaf, Stem and Root Bark Oils of O. suaveolens

Analysis of the essential oils of the leaves, stem and root barks of O. suaveolens allowed the identification of 55, 40 and 23 compounds, accounting for 88.1–93.7%, 94.0–96.0% and 94.3–98.8% of the global composition, respectively (Table 2, Table 3 and Table 4). These essential oils consisted almost exclusively of sesquiterpene hydrocarbons exhibiting (E)-β-caryophyllene and α-humulene as major components. (E)-β-caryophyllene is predominant in the leaf essential oil and associated with α-humulene (α-caryophyllene) in the trunk and root bark oil samples. The percentage of (E)-β-caryophyllene accounted for 33.5–39.3% in the leaf oils (Table 2). (E)-β-Farnesene (5.9–9.3%), caryophyllene oxide (2.1–7.7%) and α-humulene (4.0–4.6%) were present in appreciable content. Non-terpene linear compounds (0.6–6.1%) and diterpenes (1.5–3.9%) were represented in non-negligible amounts while monoterpenes (0.6–1.8%) were weakly represented. Stem bark oils were characterized by close amounts of α-humulene (38.3–45.8%) and (E)-β-caryophyllene (34.7–41.6%) (Table 3). Two oxygenated sesquiterpenes, caryophyllene oxide (2.3–4.1%) and humulene oxide II (2.1–3.7%), were present in non-negligible amounts. Amounts of monoterpenes (0.1–2.0%), diterpenes (0–0.4%), aromatic derivatives (0–1.2%) and non-terpene linear compounds (0.1–0.6%) were low. The same association of α-humulene (36.1–47.9%)/(E)-β-caryophyllene (34.3–43.3%) was also evidenced from root bark oil (Table 4). A sesquiterpene hydrocarbon, geijerene (1.4–5.9%), and three oxygenated sesquiterpenes, caryophyllene oxide (0.6–4%), humulene oxide II (1.1–4.5%) and humulene oxide III (2.4–7.7%), were present in appreciable content while monoterpenes and non-terpene linear compounds were represented in much lower content, 0–1.7% and 0–3.8%, respectively. Whatever the organ of the plant, the chemical variability was very low.
(E)-β-Caryophyllene, a major component of O. suaveolens oils, was also found as a major component in the oils of species belonging to the same family, such as O. suaveolens (Rutaceae); Murraya paniculata, 57.57% [33]; Acronychia pedunculata, 57.63%; Clausena excavata, 55.41% [34]; Bouchardatia neurococca, 38.5% [35]; and Melicope peninsularis, 49% [36], as well as in the Ivorian species Polyalthia oliveri [19].

4. Conclusions

The leaf essential oil of Guibourtia ehie and leaf, stem bark and root bark essential oils of Oricia suaveolens were analyzed by GC(RI), GC-MS and 13C NMR. All of these essential oils were dominated by hydrocarbon sesquiterpenes. The stem and root bark oils of Oricia suaveolens were characterized by the couple α-humulene (α-caryophyllene)T(E)-β-caryophyllene, while the leaf oils of Guibourtia ehie and Oricia suaveolens were dominated by (E)-β-caryophyllene. The essential oils of these two plant species can therefore be considered as natural sources of caryophyllenes.

Supplementary Materials

The following supporting information can be downloaded at: https://www.mdpi.com/article/10.3390/compounds3010006/s1, Table S1: Yields of hydrodistillation.

Author Contributions

Conceptualization, T.A.K., J.A.M.-B., Y.-A.B. and Z.A.O.; methodology, T.A.K., B.A.K. and Z.A.O.; software, Z.A.O., P.T., A.B. and M.P.; validation, A.B., J.A.M.-B., Y.-A.B. and F.T.; formal analysis, T.A.K., D.A.K. and Z.A.O.; essential oil investigation, T.A.K., D.A.K., B.A.K. and Z.A.O.; writing—original draft preparation, T.A.K., Z.A.O., A.B. and F.T.; writing—review and editing, T.A.K., Z.A.O., A.B. and F.T.; visualization, D.A.K., P.T. and M.P.; supervision, F.T. 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.

Data Availability Statement

Data and samples of the essential oils are available from the authors.

Acknowledgments

The authors gratefully acknowledge the University of Corsica for accepting Z.A. Ouattara at “Laboratoire Sciences Pour l’Environnement” for an advanced training course. We acknowledge H. Téhé and Y. Konan for their valuable help in the plant identification.

Conflicts of Interest

The authors declare no conflict of interest.

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Table 1. Chemical composition of leaf oil samples of Guibourtia ehie.
Table 1. Chemical composition of leaf oil samples of Guibourtia ehie.
CompoundsRIaRIpG1G2G3G4Identification
1Undecan-2-one12741591--0.20.2RI, MS
2δ-Elemene133514720.90.31.71.7RI, MS, 13C NMR
3α-Cubebene 134814590.10.20.20.1RI, MS
4α-Ylangene136815800.10.40.10.1RI, MS
5α-Copaene137514931.52.72.51.9RI, MS, 13C NMR
6β-Elemene138715939.05.59.57.7RI, MS, 13C NMR
7(E)-β-Caryophyllene 1417160040.440.440.826.9RI, MS, 13C NMR
8β-Copaene142615800.10.20.31.8RI, MS, 13C NMR
9γ-Elemene14291639-0.10.10.2RI, MS
10(E)-α-Bergamotene 143115871.21.71.30.9RI, MS, 13C NMR
11α-Guaiene 143415911.01.00.80.6RI, MS, 13C NMR
12(E)-β-Farnesene144616690.81.11.00.7RI, MS, 13C NMR
13α-Humulene 144816699.19.79.46.7RI, MS, 13C NMR
14allo-Aromadendrene145716450.50.90.80.9RI, MS, 13C NMR
15γ-Muurolene146916890.50.70.70.8RI, MS, 13C NMR
16Germacrene D147417097.75.67.18.1RI, MS, 13C NMR
17Tridecan-2-one 147618090.40.70.60.5RI, MS, 13C NMR
18β-Selinene148217151.10.81.21.2RI, MS, 13C NMR
19α-Selinene 149217150.11.00.11.2RI, MS, 13C NMR
20α-Burnesene149917181.41.41.11.0RI, MS, 13C NMR
21β-Bisabolene150521900.10.20.2-RI, MS
22γ-Cadinene150817500.10.30.10.2RI, MS
23δ-Cadinene 151515571.21.21.42.1RI, MS, 13C NMR
24Selina-3.7(11)-diene152917910.10.20.20.1RI, MS
25β-Elemol 153320772.61.61.64.2RI, MS, 13C NMR
26(E)-Nerolidol 154720400.50.40.30.8RI, MS, 13C NMR
27Germacrene B154918260.40.20.30.5RI, MS
28Spathulenol 156621190.50.40.20.2RI, MS
29Caryophyllene oxide156917783.33.11.91.4RI, MS, 13C NMR
30Globulol157120610.10.20.20.3RI, MS
31Viridiflorol 158020790.51.80.82.5RI, MS, 13C NMR
32Guiaiol158320860.50.30.30.9RI, MS, 13C NMR
33Cedrol 159221241.31.41.11.3RI, MS, 13C NMR
34Humulene oxide II159820341.31.41.11.3RI, MS, 13C NMR
35τ-Muurolol 162521831.10.70.92.0RI, MS, 13C NMR
36α-Muurolol 1627-0.40.20.30.8RI, MS, 13C NMR
37Cubenol 163020710.1-0.10.2RI, MS
38α-Cadinol 163522272.01.21.62.7RI, MS, 13C NMR
39Nonadec-1-ene 1675-0.50.10.61.3RI, MS
40Heptadecanal 18922247-0.10.20.9RI, MS, 13C NMR
41(E)-Phytol209726080.80.40.82.9RI, MS, 13C NMR
42neo-Abietadiene 213625340.10.10.10.4RI, MS
Sesquiterpene hydrocarbons77.075.680.664.9
Oxygenated sesquiterpenes14.212.710.418.6
Diterpenes0.90.50.93.3
Non-terpenic compounds0.90.91.62.9
Total93.489.993.890.2
Order of elution and percentages on apolar column (BP-1); RIa, RIp: retention indices measured on apolar and polar capillary columns, respectively.
Table 2. Chemical composition of leaf oil samples of Oricia suaveolens.
Table 2. Chemical composition of leaf oil samples of Oricia suaveolens.
Compounds RIaRIpF1F2F3Identification
1(E)-Hex-2-enal 82312252.4--RI, MS, 13C NMR
2(Z)-Hex-3-en-1-ol8381387-1.3-RI, MS, 13C NMR
3(Z)-Hex-2-en-1-ol 84214082.71.4-RI, MS, 13C NMR
4Hexan-1-ol 84513520.90.6-RI, MS, 13C NMR
5α-Pinene 92910200.40.3-RI, MS
6Myrcene 9811165-0.10.1RI, MS
7(E)-Ocimene 103512540.20.10.1RI, MS
8Linalool108315491.10.80.1RI, MS, 13C NMR
9Undecan-2-one12701592-0.10.1RI, MS
10α-Copaene 137514930.10.10.1RI, MS
11β-Bourbonene 138315200.10.20.1RI, MS
12α-Funebrene138615383.33.82.5RI, MS, 13C NMR
13α-Ionone 140018490.10.10.1RI, MS
14(E)-Caryophyllene 1417160039.333.538.7RI, MS, 13C NMR
15β-Copaene14271587-0.20.1RI, MS
16Geranyl acetone142918550.10.10.3RI, MS
17trans-α-Bergamotene 143115871.42.32.3RI, MS, 13C NMR
18α-Sesquisabinene 143416453.43.51.9RI, MS, 13C NMR
19(E)-Farnesene 144616699.38.85.9RI, MS, 13C NMR
20α-Humulene 144816694.04.34.6RI, MS, 13C NMR
21(Z,Z)-α-Farnesene146116910.10.20.1RI, MS
22β-Ionone 14641963-0.20.2RI, MS
23α-Curcumene146917700.20.90.7RI, MS, 13C NMR
24γ-Curcumene 147116910.80.50.2RI, MS, 13C NMR
25Germacrene D147417091.31.71.1RI, MS, 13C NMR
26Tridecan-2-one 148118070.10.70.5RI, MS, 13C NMR
27β-Selinene148517150.10.20.2RI, MS
28Bicyclogermacrene148917330.2--RI, MS
29(Z,E)-Farnesene14901718-0.30.3RI, MS
30(Z)-α-Bisabolene 149117290.71.00.6RI, MS, 13C NMR
31(E,E)-α-Farnesene 149517512.44.63.8RI, MS, 13C NMR
32β-Bisabolene14991727-1.11.3RI, MS, 13C NMR
33β-Curcumene 150017411.80.90.2RI, MS, 13C NMR
34β-Sesquiphellandrene 151317702.62.71.9RI, MS, 13C NMR
35(E)-γ-Bisabolene152117570.20.50.4RI, MS
36trans-Sesquisabinene hydrate 152919921.21.10.8RI, MS, 13C NMR
37β-Elemol 153220802.41.80.8RI, MS, 13C NMR
38(E)-Nerolidol 154720431.11.20.7RI, MS, 13C NMR
39cis-Sesquisabinene hydrate156320861.81.11.6RI, MS, 13C NMR
40Caryophyllene oxide156719812.12.97.7RI, MS, 13C NMR
41cis-7-epi-Sesquisabinene 157421000.50.50.4RI, MS
42Guaiol 158320890.7--RI, MS, 13C NMR
43Globulol15832077-0.70.1RI, MS, 13C NMR
44Humulene oxide II159220370.20.61.3RI, MS, 13C NMR
45Zingiberenol I159821100.20.60.4RI, MS, 13C NMR
46Zingiberenol II161721940.30.40.5RI, MS
47γ-Eudesmol16192164-0.3-RI, MS
48β-Eudesmol163321190.30.20.3RI, MS
49α-Eudesmol163721240.30.30.2RI, MS
50Bulnesol 165122060.20.1-RI, MS
51β-Bisabolol165221510.50.50.8RI, MS, 13C NMR
52α-Bisabolol167522120.10.10.1RI, MS
53iso-Phytol 1940--1.13.2RI, MS
54(Z)-Phytol 209525222.5--RI, MS, 13C NMR
55(E)-Phytol20972608-0.40.7RI, MS, 13C NMR
Monoterpene hydrocarbons0.60.50.2
Oxygenated monoterpenes1.20.90.4
Sesquiterpene hydrocarbon71.471.667.3
Oxygenated sesquiterpenes11.912.415.7
Diterpenes2.51.53.9
Non-terpenic compounds6.14.10.6
Order of elution and percentages on apolar column (BP-1); RIa, RIp: retention indices measured on apolar and polar capillary columns, respectively.
Table 3. Chemical composition of stem bark oil samples of Oricia suaveolens.
Table 3. Chemical composition of stem bark oil samples of Oricia suaveolens.
Compounds RIaRIpT1T2T3T4Identification
1α-Pinene 93110200.10.1-0.1RI, MS
2Sabinene 96611270.10.30.20.3RI, MS
3Myrcene 9811166-0.30.10.1RI, MS
4p-Cymene 10121276-0.1-0.1RI, MS
5Limonene 10221205-0.10.10.1RI, MS
6Nonanal 108313970.10.30.10.1RI, MS
71,3-Dimethoxybenzene 1137--0.20.1-RI, MS
8Decanal 11851501-0.1-0.1RI, MS
9Neral 12161682-0.40.20.3RI, MS
10Geraniol 12351848-0.1-0.1RI, MS
11Geranial12441733-0.70.50.6RI, MS, 13C NMR
12α-Copaene 137414920.20.20.10.8RI, MS, 13C NMR
13β-Elemene 138615920.20.70.31.1RI, MS, 13C NMR
14cis-α-Bergamotene141015690.92.10.41.2RI, MS, 13C NMR
15(E)-β-Caryophyllene 1417160041.634.739.835.2RI, MS, 13C NMR
16α-guiaene14351592-0.40.11.6RI, MS, 13C NMR
17α-Humulene 1448166945.838.544.138.3RI, MS, 13C NMR
18γ-Muurolene147116890.10.30.10.7RI, MS, 13C NMR
19Germacrene D147517080.10.10.10.3RI, MS
20β-Selinene14901718-0.1-0.1RI, MS
21Valencene149217240.20.20.10.7RI, MS, 13C NMR
22(E,E)-α-Farnesene 149517500.60.1-1.9RI, MS, 13C NMR
23α-Bulnesene 14981715-0.5-0.2RI, MS
24α-Muurolene 15011718-0.30.30.2RI, MS
25γ-Cadinene 15051752-0.1-0.3RI, MS
26δ-Cadinene 151317580.10.20.10.4RI, MS
27(E)-γ-Bisabolene 152217570.60.1--RI, MS, 13C NMR
28β-Elemol 15332077-1.4-1.6RI, MS, 13C NMR
29(E)-Nerolidol 15472040-0.1-0.1RI, MS
30Germacrene B155018270.10.2-0.1RI, MS
31Caryophyllene oxide156719812.34.04.13.2RI, MS, 13C NMR
32Humulene oxide I *158320110.20.40.10.2RI, MS
33Guiaol *15832086-0.40.20.6RI, MS, 13C NMR
34Humulene oxide II159220372.13.73.53.2RI, MS, 13C NMR
35Humulene oxide III161520480.30.30.80.4RI, MS
36β-Eudesmol163322280.10.20.10.2RI, MS
37α-Cadinol 163922240.10.3-0.1RI, MS
38α-Eudesmol165222150.10.40.10.4RI, MS
39Benzyl benzoate17222620-1.0--RI, MS, 13C NMR
40(E)-Phytol209726080.10.4-0.3RI, MS
Monoterpene hydrocarbons0.10.80.40.6
Oxygenated monoterpenes01.20.71.0
Sesquiterpene hydrocarbons89.978.785.583.1
Oxygenated sesquiterpenes5.211.28.910.0
Diterpenes0.10.400.3
Non-terpenic compounds0.10.60.10.2
Aromatic derivatives01.20.10
Total96.094.095.795.2
Order of elution and percentages on apolar column (BP-1), except components with an asterisk (*), where percentages are taken on a polar column (BP-20). RIa, RIp: retention indices measured on apolar and polar capillary columns, respectively.
Table 4. Chemical composition of root bark oil samples of Oricia suaveolens.
Table 4. Chemical composition of root bark oil samples of Oricia suaveolens.
Compounds RIaRIpR1R2R3R4R5Identification
1α-Pinene9311020-0.70.10.1-RI, MS, 13C NMR
2Sabinene 9661127---0.1-RI, MS
3Geijerene 113513281.72.01.45.91.4RI, MS
4Geranial12441733-0.10.20.40.1RI, MS
5Undecan-2-one12741592-0.8---RI, MS, 13C NMR
6Pregeijerene127713160.10.10.21.00.1RI, MS
7Myrtenyl acetate13061689-0.9--0.9RI, MS, 13C NMR
8α-Ylangene136714820.2----RI, MS
9Cyclosativene13681483-0.40.31.00.2RI, MS, 13C NMR
10α-Copaene13751493-0.20.10.30.2RI, MS
11β-Elemene13871593-0.10.10.40.1RI, MS
12(E)-β-Caryophyllene 1417160043.335.340.534.334.8RI, MS, 13C NMR
13α-Humulene 1448166947.941.545.036.140.4RI, MS, 13C NMR
14γ-Muurolene14691689-0.20.20.40.1RI, MS
15Tridecan-2-one 14761809-3.0---RI, MS, 13C NMR
16(E,E)-α-Farnesene150017500.50.40.50.40.4RI, MS
17β-Elemol 15332077--0.3-0.7RI, MS, 13C NMR
18Caryophyllene oxide156719810.62.62.02.14.0RI, MS, 13C NMR
19Humulene oxide I158320130.30.60.60.70.9RI, MS, 13C NMR
20Humulene oxide II159220371.13.32.32.84.5RI, MS, 13C NMR
21Humulene oxide III161320512.94.62.47.76.8RI, MS
22τ-Muurolol 16252183-0.20.20.30.3RI, MS
23α-Cadinol 163522270.20.20.20.30.3RI, MS
Monoterpene hydrocarbons00.70.10.20
Oxygenated monoterpenes01.00.20.41.0
Sesquiterpene hydrocarbons93.780.288.379.877.7
Oxygenated sesquiterpenes5.111.58.013.917.5
Non-terpenic compounds03.8000
Total98.897.296.694.396.2
Order of elution and percentages on apolar column (BP-1); RIa, RIp: retention indices measured on apolar and polar capillary columns, respectively.
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Kouao, T.A.; Ouattara, Z.A.; Kambiré, D.A.; Kouamé, B.A.; Mamyrbékova-Békro, J.A.; Tomi, P.; Paoli, M.; Bighelli, A.; Békro, Y.-A.; Tomi, F. Caryophyllene-Rich Essential Oils of Two Species from Southern Côte d’Ivoire: Guibourtia ehie (A. Chev.) J Léonard (Caesalpiniaceae) and Oricia suaveolens (Engl.) Verd. (Rutaceae). Compounds 2023, 3, 73-82. https://doi.org/10.3390/compounds3010006

AMA Style

Kouao TA, Ouattara ZA, Kambiré DA, Kouamé BA, Mamyrbékova-Békro JA, Tomi P, Paoli M, Bighelli A, Békro Y-A, Tomi F. Caryophyllene-Rich Essential Oils of Two Species from Southern Côte d’Ivoire: Guibourtia ehie (A. Chev.) J Léonard (Caesalpiniaceae) and Oricia suaveolens (Engl.) Verd. (Rutaceae). Compounds. 2023; 3(1):73-82. https://doi.org/10.3390/compounds3010006

Chicago/Turabian Style

Kouao, Toffé Alexis, Zana Adama Ouattara, Didjour Albert Kambiré, Bosson Antoine Kouamé, Janat Akhanovna Mamyrbékova-Békro, Pierre Tomi, Mathieu Paoli, Ange Bighelli, Yves-Alain Békro, and Felix Tomi. 2023. "Caryophyllene-Rich Essential Oils of Two Species from Southern Côte d’Ivoire: Guibourtia ehie (A. Chev.) J Léonard (Caesalpiniaceae) and Oricia suaveolens (Engl.) Verd. (Rutaceae)" Compounds 3, no. 1: 73-82. https://doi.org/10.3390/compounds3010006

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