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Article

Comparative Study of the Chemical Composition of Root, Stem and Leaf Essential Oils from Synedrella nodiflora (L.) Gaertn

by
Didjour Albert Kambiré
1,
Kayatou Touré
2,
Thierry Acafou Yapi
2,
Mathieu Paoli
3,
Ange Bighelli
3,
Jean Brice Boti
2 and
Félix Tomi
3,*
1
UPR de Chimie Organique, Département de Mathématiques, Physique et Chimie, UFR des Sciences Biologiques, Université Peleforo Gon Coulibaly, Korhogo BP 1328, Côte d’Ivoire
2
Laboratoire de Constitution et Réaction de la Matière, UFR-SSMT, Université Félix Houphouët-Boigny, Abidjan BP V34, 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 2024, 4(3), 521-533; https://doi.org/10.3390/compounds4030031
Submission received: 17 June 2024 / Revised: 3 August 2024 / Accepted: 13 August 2024 / Published: 20 August 2024
(This article belongs to the Special Issue Feature Papers in Compounds (2024))
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Abstract

:
This study aims at investigating the chemical composition of root, stem and leaf essential oils from Ivorian Synedrella nodiflora, with the root oil being described for the first time. Sixty, fifty-one and forty-nine constituents were, respectively identified in the root, stem and leaf oils using a combination of GC(RI), GC-MS and 13C-NMR analyses. They accounted for 95.6–97.3%, 92.6–97.6% and 93.3–98.8% of the total composition, respectively. The main components of the root oil samples were γ-curcumene, (E)-β-caryophyllene, α-curcumene and curcuphenyl acetate. Three stem oil samples (S1, S2a, S3) were dominated by myrcene and limonene, while the most abundant components of sample S2b were thymol, germacrene D and β-elemene. (E)-β-caryophyllene and germacrene D were the major compounds of the leaf oil. Hierarchical cluster and principal component statistical analyses were performed and confirmed that the location does not influence the chemical composition. Group I consisted of the seven leaf oil samples, group II consisted of four stem oil samples and group III consisted of three root oil samples. The root oil composition differed considerably from the stem and leaf oil composition due to the presence of curcumene derivatives as major constituents. The leaf oil showed significant amounts of (E)-β-caryophyllene and germacrene D, while the stem oil stood out for its high myrcene, limonene and thymol contents.

Graphical Abstract

1. Introduction

Synedrella nodiflora (L.) Gaertn (synonyms Ucacou nodiflorum (L.) Hitchc. and Verbesina nodiflora L.) is a herbaceous, erect, branched, pubescent annual plant belonging to the genus Synedrella, which contains only one species from the Asteraceae family. It grows in ruderal and sometimes humid places and can reach 60 cm to 1 m in height [1]. The leaves have veins and are hairy, glabrous, elliptical or ovate, pinnate, an acuminated apex, are obtuse at the base end and toothed. Native to tropical America, this plant is widely distributed in the humid regions of West Africa [2,3].
The leaves of S. nodiflora are commonly eaten by cattle and humans. S. nodiflora is used in traditional medicine in various therapeutic indications. The sap from leaves is used to treat earaches, headaches and abdominal pain. Leaf infusion is taken orally as a laxative, and root decoction is used against cough. The whole plant is further used against arthritis, rheumatism, oedema, hematoma, leprosy, mycosis, gonorrhea, hemorrhoids, diarrhea, insect pests and to stop bleeding [1,2,3,4,5,6,7]. In tropical regions of the world (Africa, Asia, Caribbean and Latin America) the plant is used as an anti-inflammatory, emmenagogue, diuretic, contraceptive and against varicose ulcers, wounds, leprosy, heart diseases and colds. The aqueous extract is drunk to treat epilepsy, hiccups and as an anti-abortion measure [8].
Investigations into solvent extracts, essential oil composition and the biological activity of S. nodiflora were previously reported. Phytochemical screenings revealed the presence of alkaloids, steroids, triterpenoids, coumarins, tannins and other phenolic compounds [3,4,5,6,7,8,9,10,11]. Antioxidant, anti-inflammatory, insecticidal, antimicrobial and antibacterial activities were also evidenced for some solvent extracts [1,4,6,7,9,10]. The chemical composition of the plant essential oil from India is dominated by farnesene, β-caryophyllene, δ-cadinene and germacrene D [12]. The essential oil of leaves from islands in Fiji showed high amounts of β-caryophyllene followed by β-farnesene, germacrene D and β-cubebene [13], while limonene, α-santalene, n-tetradecane and n-hexadecane are the main compounds of the stem essential oil from Nigeria [14]. In Côte d’Ivoire, the composition of a single sample of leaf oil was previously described, with a predominance of β-caryophyllene, germacrene D, caryophyllene oxide and β-elemene [15].
This study is part of our works on the chemical characterization of essential oils from Côte d’Ivoire [16,17,18,19,20]. We report the determination and the comparison of the chemical composition of the essential oil of three organs (root, stem and leaf) of S. nodiflora in three locations characterized by diverse pedoclimatic conditions, littoral humid forests and wooded savannah. The essential oil composition of the root is being reported here for the first time, to our knowledge.

2. Materials and Methods

2.1. Plant Material and Essential Oil Isolation

The fresh roots, stems and leaves of S. nodiflora were collected from the edge of the following two forests: Adiopodoumé Forest, Region of Lagunes, southern Côte d’Ivoire, geographical coordinates 5°19′57.7″ N and 4°08′02.0″ W (Location 1); Yapo-Abbé Forest, Region of Agneby-Tiassa, southern Côte d’Ivoire, geographical coordinates 5°40′43.1″ N and 4°05′56.0″ W (Location 2); and nearby Korhogo, Region of Poro, northern Côte d’Ivoire, geographical coordinates 9°25′20.7″ N and 5°38′18.3″ W (Location 3). The harvest took place during the dry season (January and February 2021), and plant material was authenticated by botanists from the Centre Suisse de Recherches Scientifiques (CSRS) and the Centre National de Floristique (CNF, Abidjan, Côte d’Ivoire) in accordance with voucher specimens available at the CNF. The fresh leaves, stems and root samples were hydrodistilled for 3 h each using a Clevenger-type apparatus. Essential oil yields were calculated from fresh plant material (w/w) and are reported in Table 1.

2.2. Gas Chromatography

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; the injector temperature was 250 °C; the detector temperature was 250 °C; the carrier gas was hydrogen (0.8 mL/min); the split was 1/60; and the injected volume was 0.5 µL. Retention indices (RI) were determined relative to the retention times of a series of n-alkanes (C8–C29) with linear interpolation (“Target Compounds” software 2013 from PerkinElmer). The quantification of the volatile compounds was obtained using a relative response factor (RRF) and calculated according to the International Organization of the Flavor Industry (IOFI). The relative proportion of each compound (expressed in g/100 g) was calculated using the weight of the essential oil and reference (methyl octanoate), the peak area and relative response factors [21].

2.3. Gas Chromatography–Mass Spectrometry in Electron Impact Mode

The essential oil samples were analyzed with 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 (60 m × 0.22 mm i.d., film thickness 0.25 µm). The oven temperature was programmed from 60 to 230 °C at 2°/min and then held isothermal for 45 min. Additionally, the injector temperature was 250 °C; the ion-source temperature was 250 °C; the carrier gas was He (1 mL/min); the split ratio was 1:80; the injection volume was 0.2 µL; and the ionization energy was 70 eV. The electron ionization (EI) mass spectra were acquired over the mass range 35–350 Da.

2.4. Nuclear Magnetic Resonance

The 13C-NMR spectra of 14 samples (root, stem, leaf) 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, in CDCl3, with all shifts referring to the internal TMS. The following parameters were used: pulse width = 4 µs (flip angle 45°); relaxation delay D1 = 0.1 s, acquisition time = 2.7 s for 128 K 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 (40 mg, when available, in 0.5 mL of CDCl3).
A laboratory-made software compares the chemical shift of every carbon in the experimental spectrum with the spectra of pure compounds listed in our in-house data library [22,23]. Each compound was identified taking into account the following:
-
The number of observed carbons with respect to the number of expected signals;
-
The number of overlapped signals of carbons which possess fortuitously the same chemical shift;
-
The difference of chemical shift of each signal in the mixture spectrum and in the reference.
These three parameters are directly available from the computer program. A compound was considered as identified when at least 50% of its signals belonging solely to that molecule and 70% of all its signals was observed.

2.5. Identification of Individual Components

Identification of the individual components was achieved as follows: (i) by comparison of their GC retention indices (RI) on apolar and polar columns with those of reference compounds [24,25,26]; (ii) through computer matching against digital mass spectral libraries [24,27,28]; (iii) through 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 [22,23]. This method allowed for the identification of individual components of the essential oil at contents as low as 0.4–0.5%.

2.6. Statistical Analysis

The chemical compositions of the 14 essential oil samples from S. nodiflora were submitted to hierarchical cluster analysis (HCA) and principal component analysis (PCA) using XLSTAT 2016 software (Addinsoft, Paris, France) [29]. Only constituents in a concentration of 1.0% and higher were used as variables for the PCA analysis. The XLSTATS-3DPlot module was used to afford 3D PCA using the principal factors F1, F2 and F3. The aptitude of the complete correlation matrix was checked by the Kaiser–Meyer–Olkin criterion. The HCA and dendrogram were made with dissimilarity matrices calculated through the Euclidean distance, and the average link was the aggregation method systematically chosen.

3. Results and Discussion

The chemical compositions of the essential oils from three organs of S. nodiflora growing wild in Côte d’Ivoire were determined. Essential oils were isolated by hydrodistillation of fresh plant material collected from the edge of the Yapo-Abbé and the Adiopodoumé forests, both in Southern Côte d’Ivoire and nearby Korhogo (north of the country). The oil extraction yields calculated on a weight (w/w) basis varied poorly at 0.040–0.050% (root oil samples), 0.016–0.023% (stem oil samples) and 0.011–0.040% (leaf oil samples). A combination of GC(RI)(non-polar and polar columns), GC-MS (non-polar column) and 13C-NMR, following a computerized method developed at the University of Corsica [22,23], was used to analyze the oil samples.

3.1. Chemical Composition of the Root’s Essential Oil

The root essential oil from S. nodiflora is characterized for the first time. The analysis of three oil samples led to the identification of 60 compounds, accounting for 95.6–97.3% of the whole chemical composition. They primarily consist of hydrocarbon sesquiterpenes (59.4–72.3%) followed by oxygenated sesquiterpenes (13.3–18.7%). Hydrocarbon monoterpenes and oxygenated monoterpenes accounted for 2.7–11.5% and 3.3–10.2%, respectively. Rich in curcumene derivatives, this essential oil is dominated by γ-curcumene (22.2–24.8%), (E)-β-caryophyllene (11.7–22.2%), α-curcumene (11.6–12.4%) and curcuphenyl acetate (5.6–10.7%). The majority of compounds are followed by xanthorrhizyl acetate (1.3–6.2%) and neryl isovalerate (1.2–6.2%). Other compounds are also present in significant proportions, such as β-pinene (1.0–4.6%), α-pinene (1.0–4.4%), cyclosativene (2.1–3.6%) and cyperene (1.0–3.5%) (Table 2). The harvest sites have a negligible influence on the chemical composition of the root essential oil from S. nodiflora due to the geographic areas (littoral humid forests and wooded savannah) of the three harvest sites being distant (around 550 km).

3.2. Chemical Composition of Stem Essential Oil

The chemical composition of the stem essential oil from S. nodiflora is dominated by hydrocarbon monoterpenes (23.2–61.1%) and hydrocarbon sesquiterpenes (22.9–49.5%). Fifty-one constituents representing 92.6–97.6% of the chemical composition were identified. Samples S1, S2a and S3 are rich in myrcene (19.6–22.6%) and limonene (18.3–22.1%), followed by β-pinene (5.1–11.5%), germacrene D (0.2–10.5%), β-elemene (7.6–9.2%), (E)-β-caryophyllene (7.1–8.1%), α-pinene (2.5–4.5%) and bicyclogermacrene (0.3–4.0%). As for sample S2b, the main constituents are thymol (12.7%), germacrene D (12.2%), β-elemene (11.8%), limonene (9.0%), (E)-β-caryophyllene (9.0%), myrcene (8.5%) and bicyclogermacrene (7.6%) (Table 3). Thus, two chemical compositions appear for the stem essential oil, differing by the presence of thymol in appreciable content in one of the four oil samples. This difference could be related to the vegetative stage of the plant, since samples S2a and S2b from the same location do not have the same composition.
The stem essential oil sample from Nigeria, dominated by limonene (14.9%), α-santalene (9.0%), n-hexadecane (3.0%) and n-tetradecane (3.0%), differs from those of the present study [14]. Indeed, α-santalene, n-hexadecane and n-tetradecane are absent from our samples, while, in the Nigerian oil sample, thymol, β-pinene, germacrene D, β-elemene, bicyclogermacrene and α-pinene were not detected; additionally, there was a relatively low content of myrcene (1.5%) and (E)-β-caryophyllene (1.5%). Thus, the stem essential oil from S. nodiflora of an Ivorian origin showed original chemical compositions.

3.3. Chemical Composition of Leaf Essential Oil

Forty-nine compounds, accounting for 93.3–98.8% of the whole chemical composition of the seven leaf essential oil samples, were identified. This essential oil mainly consists of hydrocarbon sesquiterpenes (59.1–86.1%) and lower contents of hydrocarbon monoterpenes (3.4–27.1%). (E)-β-caryophyllene (20.0–30.3%) and Germacrene D (7.7–33.6%) are the predominant compounds, followed by bicyclogermacrene (2.4–7.2%), β-cubebene (2.7–7.2%) and β-elemene (3.3–5.2%). However, only samples L1a and L1b from Adiopodoumé Forest contain thianthrene (2.8 and 0.6%, respectively). They also have an interesting amount of α-isocomene (6.7 and 1.1%, respectively), while L2a, L2b and L2c from Yapo-Abbé Forest exhibit appreciable thymol contents (3.0–8.7%). Sample L2c exhibited significant proportions of limonene (12.1%) and myrcene (8.0%). Samples L3a and L3b from Korhogo showed a relatively low content of germacrene D (10.0 and 7.7%, respectively vs. 21.2–33.6% for L1a-L2c). Significant amounts of (E)-phytol, a diterpene, have also been identified in samples L2a, L2c, L3a and L3b (2.2, 3.6, 4.7 and 5.1%, respectively) (Table 4). Hence, despite the predominance of (E)-β-caryophyllene and Germacrene D, quantitative differences are observable between the samples. The harvest sites and vegetative stage of the plant could be possible factors in this chemical variation.
Although a previous study conducted in Côte d’Ivoire on a single sample of leaf essential oil reported similar chemical composition with β-caryophyllene (19.5%), germacrene D (17.63%), caryophyllene oxide (10.5%) and β-elemene (9.80%) as major compounds, notable quantitative and qualitative variations are observable. Indeed, there is a low proportion of caryophyllene oxide in our samples (0.7–4.2%) compared to the previous study (10.5%). Qualitatively, some compounds that featured significantly in our samples, such as myrcene, thymol, α-isocomene, precocene, benzyl benzoate, thianthrene and (E)-phytol, were not detected in the previous study [15]. These quantitative and qualitative variations could be explained by differences in harvest sites and seasons. Moreover, the leaf essential oil from Côte d’Ivoire differs from those of Fiji and India. Germacrene D (21.2–33.6% in our samples) accounted only for 7.6 and 1.27% in oils from Fiji and India, respectively, whereas (E)-β-farnesene (11.9 and 22.75%, respectively Fiji and India) did not exceed 1.2% in our samples. Also, qualitative variations were observable through many compounds detected in our samples but absent from the Fiji and India chemical compositions, and conversely [12,13]. Combined factors, like differences in climate, vegetation, relief and harvest season, could be responsible for the observed variations.

3.4. Discussion about Statistical Analyses

Statistical analyses were carried out on the 14 essential oil compositions through hierarchical cluster analysis (HCA) and principal component analysis (PCA) to confirm the observed chemical variability. The dendrogram from the HCA displayed three distinct chemical compositions within the 14 investigated oil samples, as follows: group I (seven leaf oil samples and stem oil sample S2b), group II (three stem oil samples) and group III (three root oil samples). The first and second principal factors of the PCA (F1: 47.40% and F2: 35.16%, respectively) accounted for 82.56% of the total variance of the chemical composition. The PCA map relative to the principal axes F1 and F2 confirmed the three groups observed in the dendrogram (Figure 1). Groups II and III are more homogenous than group I. However, considering the third main factor (F3: 9.17%), in a 3D PCA projection, principal axes F1, F2 and F3 account then for 91.74% of the total variance of the chemical composition, and stem oil sample S2b fits well into group II (Figure 2).
The mean contents (M) and the standard deviation (SD) of the major compounds of the different groups are reported on Table 5. The chemical composition of each organ is homogeneous and appears to be not deeply influenced by the location. However, Korhogo leaf oil samples L3a and L3b and the Yapo-Abbé forest stem oil sample S2b exhibited slightly different chemical compositions.
Group I, consisting of the seven leaf oil samples, is dominated by (E)-β-caryophyllene (26.0 ± 3.4%) and germacrene D (22.6 ± 10.1%), followed by bicyclogermacrene (5.0 ± 1.8%). The four stem oil samples (group II) are characterized by monoterpene hydrocarbons such as myrcene (18.0 ± 6.4%), limonene (17.7 ± 6.1%) and β-pinene (7.4 ± 3.9%). In contrast, the root oil samples (group III) are characterized by the presence of γ-curcumene (23.5 ± 1.9%) and α-curcumene (12.0 ± 0.6). Other compounds, such as curcuphenyl acetate (7.6 ± 2.7%), xanthorrhizyl acetate (3.6 ± 2.5%) and neryl isovalerate (3.3 ± 2.6%), are present in significant amounts. Apart from neryl isovalerate, all these compounds were not detected in leaf oil samples.

4. Conclusions

The chemical compositions of the root, stem and leaf essential oils from S. nodiflora were investigated, with the root oil composition being reported for the first time. A combination of GC(RI), GC-MS and 13C-NMR was used for the identification and quantification of the constituents, and different chemical profiles were observed for the three organs of the plant. The location did not deeply influence the chemical composition. Leaf oil samples were dominated by sesquiterpene hydrocarbons such as (E)-β-caryophyllene and germacrene D, while stem oil samples showed monoterpene hydrocarbons, myrcene and limonene as being the most abundant constituents. The root oil samples were characterized by the high amounts of γ-curcumene and α-curcumene.

Author Contributions

Conceptualization, D.A.K., T.A.Y. and F.T.; methodology, D.A.K., K.T. and F.T.; software, D.A.K. and M.P.; validation, J.B.B., A.B. and F.T.; formal analysis, D.A.K. and K.T.; data analysis, D.A.K., T.A.Y. and F.T.; essential oil investigation, D.A.K. and K.T.; writing—original draft preparation, D.A.K. and F.T.; writing—review and editing, D.A.K., T.A.Y., J.B.B. and F.T.; visualization, D.A.K. and M.P.; supervision, T.A.Y., A.B. and F.T. All authors have read and agreed to the published version of the manuscript.

Funding

This research received no external funding.

Data Availability Statement

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

Acknowledgments

The authors gratefully acknowledge H. Téré for his valuable help in the plant identification.

Conflicts of Interest

The authors declare no conflicts of interest.

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Compounds 04 00031 g001
Figure 1. HCA dendrogram and PCA map of the 14 oil samples from S. nodiflora. (a) Hierarchical Cluster Analysis (HCA); (b) Principal Component Analysis (PCA) and biplot.
Figure 1. HCA dendrogram and PCA map of the 14 oil samples from S. nodiflora. (a) Hierarchical Cluster Analysis (HCA); (b) Principal Component Analysis (PCA) and biplot.
Compounds 04 00031 g001
Compounds 04 00031 g002
Figure 2. 3D PCA map of the 14 oil samples from S. nodiflora.
Figure 2. 3D PCA map of the 14 oil samples from S. nodiflora.
Compounds 04 00031 g002
Table 1. Plant material and essential oil extraction data.
Table 1. Plant material and essential oil extraction data.
SampleHarvest Site
Elevation (m)		OrganWeight (g)Yield (%)
Plant MaterialEssential Oil
R1Adiopodoumé Forest:
littoral humid forest 32 		Roots109.70.04430.040
S1Stems462.40.08690.019
L1aLeaves628.10.06920.011
L1b612.70.08570.014
R2Yapo-Abbé Forest:
littoral humid forest 80 		Roots459.30.22970.050
S2aStems911.40.14580.016
S2b898.00.21040.023
L2aLeaves840.80.33350.040
L2b835.90.19760.024
L2c877.20.25430.029
R3Korhogo:
wooded savannah 376		Roots428.70.18390.043
S3Stems926.10.20390.022
L3aLeaves812.40.30050.037
L3b817.00.28610.035
Table 2. Chemical composition of root essential oil from Synedrella nodiflora.
Table 2. Chemical composition of root essential oil from Synedrella nodiflora.
N°CompoundsRIaLRIaRIpRRFA (%)Y-A (%)K (%)Identification
R1R2R3
1α-Pinene93493110200.7654.41.71.0RI, MS, 13C-NMR
2Camphene94794510710.7650.10.2trRI, MS
3Sabinene96896611270.7650.10.20.1RI, MS
4β-Pinene97397111160.7652.24.61.0RI, MS, 13C-NMR
5Myrcene98398111660.7650.42.40.3RI, MS, 13C-NMR
6α-Phellandrene99999811700.7650.10.1-RI, MS
7p-Cymene1015101212760.6980.1trtrRI, MS
8β-Phellandrene *1021102212150.7650.20.30.1RI, MS
9Limonene *1024102212060.7650.51.70.2RI, MS, 13C-NMR
10(E)-β-Ocimene1038103512540.765-0.3-RI, MS
11α-Terpineol1175117416970.8090.10.1trRI, MS
12Neral1220121516820.817--0.2RI, MS
13Geraniol1238123618480.8090.1tr0.2RI, MS
14Geranial1247124417320.817--0.3RI, MS
15Thymol1271126821880.7550.70.10.4RI, MS, 13C-NMR
16Bornyl acetate1270127015820.8490.80.50.3RI, MS, 13C-NMR
17α-Cubebene1352135014580.751tr-0.2RI, MS
18Longicyclene1371136614890.7510.20.30.2RI, MS
19Cyclosativene1368136914830.7512.13.63.1RI, MS, 13C-NMR
20α-Copaene1375137514930.7510.40.70.6RI, MS, 13C-NMR
21β-Elemene1388138715910.7510.81.90.4RI, MS, 13C-NMR
22Cyperene1398139915280.7513.53.31.0RI, MS, 13C-NMR
23α-Gurjunene1405140915310.7510.40.60.5RI, MS, 13C-NMR
24cis-α-Bergamotene1410141115730.7510.10.10.1RI, MS
25(E)-β-Caryophyllene1419141715980.75111.717.122.2RI, MS, 13C-NMR
26Precocene1428143320700.8150.20.30.3RI, MS
27α-Guaiene1442143516080.7510.10.1trRI, MS
28(E)-β-Farnesene1449144616690.7510.60.50.5RI, MS, 13C-NMR
29α-Humulene1449144916690.7510.91.11.2RI, MS, 13C-NMR
30α-Curcumene1471147017760.70711.612.411.9RI, MS, 13C-NMR
31γ-Curcumene1472147216940.75124.822.223.6RI, MS, 13C-NMR
32Germacrene D1476147417090.7510.51.00.2RI, MS, 13C-NMR
33β-Selinene1481147817190.7510.10.33.9RI, MS, 13C-NMR
34γ-Humulene1483148117280.7510.10.10.1RI, MS
354-epi-Cubebol1489148518810.7870.10.10.1RI, MS
36α-Selinene1489149017230.7510.30.50.2RI, MS, 13C-NMR
37α-Muurolene1491149217320.7510.10.20.3RI, MS
38β-Bisabolene1500150017270.7510.20.40.7RI, MS, 13C-NMR
39γ-Cadinene1506150617610.7510.20.10.3RI, MS
40δ-Cadinene1514151317570.7510.50.80.8RI, MS, 13C-NMR
41Italicene oxide1525152118580.7910.10.10.2RI, MS
42Geranyl 2-methylbutyrate1562155818610.8191.70.90.4RI, MS, 13C-NMR
43Spathulenol1566156321200.7910.10.10.1RI, MS
44Neryl isovalerate1568156418810.8196.22.61.2RI, MS, 13C-NMR
45Caryophyllene oxide1570156919780.7911.41.12.9RI, MS, 13C-NMR
46Globulol1578157320610.7810.10.30.2RI, MS
47Viridiflorol1580159120800.7810.10.40.8RI, MS, 13C-NMR
48neo-Intermedeol1601160321450.781tr0.1trRI, MS
491,10-diepi-Cubenol1605161020540.7810.10.10.1RI, MS
50Intermedeol1636163722470.7810.20.30.3RI, MS
51Geranyl tiglate1649164720700.8290.20.10.2RI, MS
52Neryl tiglate1652165620910.8290.40.20.1RI, MS
53α-Bisabolol1668166522130.7810.50.30.7RI, MS, 13C-NMR
54Curcuphenol1684167626000.7461.91.31.2RI, MS, 13C-NMR
55Curcuphenyl acetate1694169026260.7816.45.610.7RI, MS, 13C-NMR
56Pentadecanal1695169420410.764-0.20.2RI, MS
57Xanthorrhizol17281737-0.7460.50.20.1RI, MS, 13C-NMR
58Xanthorrhizyl acetate17671743-0.7816.23.31.3RI, MS, 13C-NMR
59Falcarinol20001983-0.797-0.2-RI, MS
60(E)-Phytol2099209726140.7480.2-0.1RI, MS
Hydrocarbon monoterpenes 8.111.52.7
Oxygenated monoterpenes 10.24.53.3
Hydrocarbon sesquiterpenes 59.467.672.3
Oxygenated sesquiterpenes 17.713.318.7
Other compounds 0.20.40.3
Total identified 95.697.397.3
Order of elution and percentages are given on an apolar column (BP-1), except components with an asterisk (*), where percentages are taken on a polar column (BP-20). RIaL: apolar column retention indices from the literature [24,25,26]; RIa, RIp: retention indices measured on an apolar and polar capillary column, respectively. RRF: relative response factors calculated using methyl octanoate as internal standard. The relative proportions of constituent are expressed in g/100 g. tr: traces level (<0.05%). A: Adiopodoumé Forest; Y-A: Yapo-Abbé Forest; K: Korhogo.; (-): not detected.
Table 3. Chemical composition of stem essential oil from Synedrella nodiflora.
Table 3. Chemical composition of stem essential oil from Synedrella nodiflora.
N°CompoundsRIaLRIaRIpRRFA (%)Y-A (%)K (%)Identification
S1S2aS2bS3
1α-Pinene93493110200.7654.52.90.52.5RI, MS, 13C-NMR
2Camphene94794510710.7650.40.30.10.2RI, MS
3Sabinene96896611270.7650.60.80.20.5RI, MS, 13C-NMR
4β-Pinene97397111160.7659.911.53.25.1RI, MS, 13C-NMR
5Myrcene98398111660.76522.619.68.521.2RI, MS, 13C-NMR
6α-Phellandrene99999811700.7650.10.1tr-RI, MS
7α-Terpinene1010101011860.765-0.10.3-RI, MS
8p-Cymene1015101212760.698--0.40.4RI, MS
9β-Phellandrene *1021102212150.7651.21.40.71.8RI, MS, 13C-NMR
10Limonene *1024102212060.76521.518.39.022.1RI, MS, 13C-NMR
11(E)-β-Ocimene1038103512540.7650.20.20.10.4RI, MS
12γ-Terpinene1050104912500.765-tr0.2-RI, MS
13Terpinolene1079107912780.7650.1--0.4RI, MS
14Terpinen-4-ol1164116316030.809-0.10.30.4RI, MS
15α-Terpineol1175117416970.809-0.10.20.2RI, MS
16Nerol1216120917930.809--tr0.3RI, MS
17Neral1220121516820.817--0.12.5RI, MS, 13C-NMR
18Geraniol1238123618480.809--0.20.3RI, MS
19Geranial1247124317320.817--0.12.9RI, MS, 13C-NMR
20Thymol1271126821880.755-0.212.70.2RI, MS, 13C-NMR
21Bornyl acetate1270127015820.8490.40.3-0.1RI, MS
22Bicycloelemene1336133414820.751-0.10.30.5RI, MS, 13C-NMR
23α-Cubebene1352134814590.751-tr0.20.2RI, MS
24Cyclosativene1368136914830.751-0.6tr-RI, MS, 13C-NMR
25α-Copaene1375137514930.7510.60.20.20.2RI, MS, 13C-NMR
26β-Cubebene *1383138715400.7510.60.40.40.8RI, MS, 13C-NMR
27β-Elemene *1388138715910.7519.28.011.87.6RI, MS, 13C-NMR
28α-Isocomene1388138915360.751trtr-0.6RI, MS, 13C-NMR
29Cyperene1398139915280.751-0.5tr-RI, MS, 13C-NMR
30α-Gurjunene1405140915310.751-0.10.1-RI, MS
31(E)-β-Caryophyllene1419141715980.7517.17.19.08.7RI, MS, 13C-NMR
32Precocene1428143320700.815-0.60.3trRI, MS, 13C-NMR
33(E)-β-Farnesene1449144616690.751-0.20.20.5RI, MS, 13C-NMR
34α-Humulene1449144916690.7510.80.71.00.6RI, MS, 13C-NMR
35α-Curcumene1471147017760.707-1.80.70.3RI, MS, 13C-NMR
36γ-Curcumene1472147216940.7510.43.90.80.7RI, MS, 13C-NMR
37Germacrene D1476147417090.75110.56.312.20.2RI, MS, 13C-NMR
38β-Selinene1481148117190.7510.60.41.60.5RI, MS, 13C-NMR
394-epi-Cubebol1489148518810.787-0.10.10.1RI, MS
40Bicyclogermacrene1490149117330.7514.04.07.60.3RI, MS, 13C-NMR
41β-Bisabolene1500150017270.7511.51.22.31.1RI, MS, 13C-NMR
42δ-Cadinene1514151317570.7510.20.40.80.1RI, MS, 13C-NMR
43β-Elemol1536153420770.781--0.6trRI, MS, 13C-NMR
44Spathulenol1566156321190.791-0.40.73.4RI, MS, 13C-NMR
45Neryl isovalerate1568156418810.819-0.5-0.9RI, MS, 13C-NMR
46Caryophyllene oxide1570156919780.791-0.30.75.0RI, MS, 13C-NMR
47Intermedeol1636163722470.7810.60.61.21.0RI, MS, 13C-NMR
48Curcuphenyl acetate1694169026260.781-1.60.30.1RI, MS, 13C-NMR
49Benzyl benzoate1733172226200.770-tr2.00.2RI, MS, 13C-NMR
50Xanthorrhizyl acetate17671743-0.781trtrtr1.0RI, MS, 13C-NMR
51(E)-Phytol2099209726140.748-0.20.71.3RI, MS, 13C-NMR
Hydrocarbon monoterpenes 61.155.223.254.6
Oxygenated monoterpenes 0.41.213.67.8
Hydrocarbon sesquiterpenes 35.536.549.522.9
Oxygenated sesquiterpenes 0.63.03.610.6
Other compounds 0.00.22.71.5
Total identified 97.696.192.697.4
Order of elution and percentages are given on an apolar column (BP-1), except components with an asterisk (*), where percentages are taken on a polar column (BP-20). RIaL: apolar column retention indices from the literature [24,25,26]; RIa, RIp: retention indices measured on an apolar and polar capillary column, respectively. RRF: relative response factors calculated using methyl octanoate as the internal standard. The relative proportions of constituent are expressed in g/100 g. tr: traces level (<0.05%). A: Adiopodoumé Forest; Y-A: Yapo-Abbé Forest; K: Korhogo; (-): not detected.
Table 4. Chemical composition of leaf essential oil from Synedrella nodiflora.
Table 4. Chemical composition of leaf essential oil from Synedrella nodiflora.
N°CompoundsRIaLRIaRIpRRFA (%)Y-A (%)K (%)Identification
L1aL1bL2aL2bL2cL3aL3b
1α-Pinene93493110200.7650.20.60.20.21.70.81.4RI, MS, 13C-NMR
2Camphene94794510710.765-0.3trtr0.30.10.2RI, MS
3Sabinene96896611270.765-0.20.1tr0.40.20.2RI, MS, 13C-NMR
4β-Pinene97397111160.7650.41.40.70.53.61.01.8RI, MS, 13C-NMR
5Myrcene98398111660.7651.63.62.01.18.04.46.0RI, MS, 13C-NMR
6p-Cymene1015101212760.698--0.10.10.10.10.2RI, MS
7β-Phellandrene *1021102212150.7650.10.30.20.10.80.80.5RI, MS, 13C-NMR
8Limonene *1024102212060.7652.05.12.21.412.14.44.8RI, MS, 13C-NMR
9(E)-β-Ocimene1038103512540.765-trtr-0.1-0.1RI, MS
10Terpinolene1079107912780.7652.30.4tr--0.20.1RI, MS, 13C-NMR
11Nerol12161 21017930.809----0.10.1-RI, MS
12Neral12201 21516820.817--trtr0.31.7trRI, MS, 13C-NMR
13Geraniol1238123418490.809--0.10.10.30.50.1RI, MS, 13C-NMR
14Geranial1247124217310.817--trtr0.52.7-RI, MS, 13C-NMR
15Thymol1271126821880.7550.50.28.74.83.00.20.2RI, MS, 13C-NMR
16Bornyl acetate1270127015820.8490.20.3-0.10.60.10.1RI, MS, 13C-NMR
17Bicycloelemene1336133414820.751-0.20.30.40.20.10.1RI, MS
18α-Cubebene1352134714720.7511.50.20.10.10.10.10.1RI, MS, 13C-NMR
19α-Copaene1375137514930.7511.00.90.60.60.50.91.7RI, MS, 13C-NMR
20β-Bourbonene1381138515200.7510.80.80.91.10.33.72.9RI, MS, 13C-NMR
21β-Cubebene *1383138715400.7514.04.63.94.52.77.23.9RI, MS, 13C-NMR
22β-Elemene *1388138715910.7515.24.33.94.33.33.53.6RI, MS, 13C-NMR
23α-Isocomene1388138915360.7516.71.1---0.1trRI, MS, 13C-NMR
24α-Gurjunene1405140915310.7513.20.50.20.20.10.20.4RI, MS, 13C-NMR
25(E)-β-Caryophyllene1419141715980.75124.326.025.230.320.026.929.4RI, MS, 13C-NMR
26β-Copaene 1427142815820.7510.20.30.30.40.20.70.7RI, MS, 13C-NMR
27Precocene1428143320700.8151.30.40.20.31.91.50.8RI, MS, 13C-NMR
28(E)-β-Farnesene1449144616690.7510.91.20.70.80.70.90.7RI, MS, 13C-NMR
29α-Humulene1449144916690.7512.92.92.53.12.22.63.1RI, MS, 13C-NMR
30Germacrene D1476147417090.75128.133.627.729.721.210.07.7RI, MS, 13C-NMR
31β-Selinene1481148117190.751---0.30.30.20.6RI, MS, 13C-NMR
324-epi-Cubebol1489148518810.787--0.20.30.20.31.0RI, MS, 13C-NMR
33Bicyclogermacrene1490149117330.7515.26.46.47.24.52.43.2RI, MS, 13C-NMR
34α-Muurolene1491149217320.751---0.40.30.20.6RI, MS, 13C-NMR
35(E,E)-α-Farnesene1496149817510.7510.40.50.40.2tr0.20.2RI, MS, 13C-NMR
36β-Bisabolene1500150017270.751--0.40.30.20.71.0RI, MS, 13C-NMR
37δ-Cadinene1514151317570.7510.40.40.50.70.40.53.1RI, MS, 13C-NMR
38β-Elemol1536153420770.781--0.40.30.10.40.5RI, MS, 13C-NMR
39Spathulenol1566156321190.7910.40.10.60.10.61.21.1RI, MS, 13C-NMR
40Neryl isovalerate1568156618820.819trtr0.10.10.10.90.9RI, MS, 13C-NMR
41Caryophyllene oxide1570156919780.7910.80.70.80.90.84.14.2RI, MS, 13C-NMR
42Isospathulenol1625161921950.791--0.20.10.10.30.3RI, MS
43τ-Cadinol1626162621670.781--0.30.2trtr0.6RI, MS, 13C-NMR
44Curcuphenol1684167726000.746--0.20.1-1.11.0RI, MS, 13C-NMR
45Benzyl benzoate1733172226200.770--1.21.0-0.1trRI, MS, 13C-NMR
46Thianthrene18831876-0.8902.80.6-----RI, MS, 13C-NMR
47Cembrene A1959195422450.744--0.60.30.10.30.2RI, MS, 13C-NMR
48Falcarinol20001983-0.797--0.5tr---RI, MS
49(E)-Phytol2099209726140.7480.80.72.20.53.64.75.1RI, MS, 13C-NMR
Hydrocarbon monoterpenes 6.611.95.53.427.112.015.3
Oxygenated monoterpenes 0.70.58.95.14.96.21.3
Hydrocarbon sesquiterpenes 86.184.374.284.959.162.663.8
Oxygenated sesquiterpenes 1.20.82.72.01.87.48.7
Other compounds 3.61.34.51.83.75.15.3
Total identified 98.298.895.897.296.693.394.4
Order of elution and percentages are given on an apolar column (BP-1), except components with an asterisk (*), where percentages are taken on a polar column (BP-20). RIaL: apolar column retention indices from the literature [24,25,26]; RIa, RIp: retention indices measured on an apolar and polar capillary column, respectively. RRF: relative response factors calculated using methyl octanoate as the internal standard. The relative proportions of constituent are expressed in g/100 g. tr: traces level (<0.05%). A: Adiopodoumé Forest; Y-A: Yapo-Abbé Forest; K: Korhogo; (-): not detected.
Table 5. Main compounds of the three groups related to the three organs of S. nodiflora.
Table 5. Main compounds of the three groups related to the three organs of S. nodiflora.
Group IGroup IIGroup III
Component [a]M% ± SDMinMaxM% ± SDMinMaxM% ± SDMinMax
α-Pinene0.7 ± 0.60.21.72.6 ± 1.60.54.52.4 ± 1.81.04.4
β-Pinene1.3 ± 1.10.43.67.4 ± 3.93.211.52.6 ± 1.81.04.6
Myrcene3.8 ± 2.51.18.018.0 ± 6.48.522.61.0 ± 1.20.32.4
Limonene4.6 ± 3.61.412.117.7 ± 6.19.022.10.8 ± 0.80.21.7
Thymol2.5 ± 3.30.28.73.3 ± 6.3-12.70.4 ± 0.30.10.7
β-Cubebene *4.4 ± 1.42.77.20.6 ± 0.20.40.8---
β-Elemene *4.0 ± 0.63.35.29.2 ± 1.97.611.81.0 ± 0.80.41.9
(E)-β-Caryophyllene26.0 ± 3.420.030.38.0 ± 1.07.19.017.0 ± 5.311.722.2
α-Curcumene---0.7 ± 0.8-1.812.0 ± 0.411.612.4
γ-Curcumene---1.5 ± 1.60.43.923.5 ± 1.322.224.8
Germacrene D22.6 ± 10.17.733.67.3 ± 5.30.212.20.6 ± 0.40.21.0
Bicyclogermacrene5.0 ± 1.82.47.24.0 ± 3.00.37.6---
Neryl isovalerate0.3 ± 0.4-0.90.4 ± 0.4-0.93.3 ± 2.61.26.2
Curcuphenyl acetate---0.5 ± 0.7-1.67.6 ± 2.75.610.7
Xanthorrhizyl acetate---0.3 ± 0.5tr1.03.6 ± 2.51.36.2
(E)-Phytol2.5 ± 2.00.55.10.6 ± 0.6-1.30.1 ± 0.1-0.2
[a] Order of elution and percentages on apolar column (BP-1), except components with an asterisk (*), percentages on polar column (BP-20); M% ± SD: mean percentage and standard deviation; tr: traces level (<0.05%); (-): not detected.
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Kambiré, D.A.; Touré, K.; Yapi, T.A.; Paoli, M.; Bighelli, A.; Boti, J.B.; Tomi, F. Comparative Study of the Chemical Composition of Root, Stem and Leaf Essential Oils from Synedrella nodiflora (L.) Gaertn. Compounds 2024, 4, 521-533. https://doi.org/10.3390/compounds4030031

AMA Style

Kambiré DA, Touré K, Yapi TA, Paoli M, Bighelli A, Boti JB, Tomi F. Comparative Study of the Chemical Composition of Root, Stem and Leaf Essential Oils from Synedrella nodiflora (L.) Gaertn. Compounds. 2024; 4(3):521-533. https://doi.org/10.3390/compounds4030031

Chicago/Turabian Style

Kambiré, Didjour Albert, Kayatou Touré, Thierry Acafou Yapi, Mathieu Paoli, Ange Bighelli, Jean Brice Boti, and Félix Tomi. 2024. "Comparative Study of the Chemical Composition of Root, Stem and Leaf Essential Oils from Synedrella nodiflora (L.) Gaertn" Compounds 4, no. 3: 521-533. https://doi.org/10.3390/compounds4030031

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