Following the determination of the chemical compositions of leaf, stem bark and root essential oils from Isolona dewevrei (Annonaceae), those of the flowers and fruits are investigated for the first time. Analyses by combination of GC(RI), GC-MS and 13C-NMR techniques led to the identification of fifty-three constituents (97.6-99.4%) and seventy-three compounds (97.7-99.0%) in the flower and fruit oils, respectively. The flower oil is rich in oxygenated sesquiterpenes and monoterpene hydrocarbons (49.8-73.1% and 4.6-32.2%, respectively), with caryophyllene oxide (37.0-52.1%), limonene (10.8-13.2%), p-cymene (9.6-11.1%), terpinen-4-ol (4.1-8.5%), humulene oxide II (5.1-5.7%) and alismol (3.1-6.1%) as main constituents. Monoterpene hydrocarbons (30.6-62.8%), sesquiterpene hydrocarbons (16.1-32.3%) and oxygenated sesquiterpenes (11.5-30.8%) are prevalent in the fruit oil, which is dominated by (E)-beta-ocimene (13.5-28.3%), (Z)-beta-ocimene (5.7-14.9%), sabinene (5.4-12.6%) and germacrene D (2.4-12.5%). Some identified compounds such as (10 beta H)-1 beta,8 beta-oxido-cadina-4-ene, (5 alpha H,10 beta Me)-6,12-oxido-elema-1,3,6,11(12)-tetraene, germacrene D-8-one, (7 alpha H)-germacrene D-8 alpha-ol, cadina-1(10),4-dien-8 beta-ol and (1 beta H,5 beta H)-6,12-oxido-guaia-6,10(14),11(12)-trien-4 alpha-ol, could serve as chemotaxonomic markers of this species.
The present study reports, for the first time, the chemical composition of the leaf essential oil (LEO) from Aspilia rudis as well as its antioxidant and anti-inflammatory activities. Analysis combining GC(RI), GC-MS and 13C-NMR of 36 samples identified 58 compounds representing 96.7-99.3% of the whole composition. Statistical analyses revealed chemical variability in three clusters, each composed of samples from the same sampling site. Cluster I is dominated by germacrene D (27.2 ± 2.7%), α-pinene (24.0 ± 2.9%) and (E)-β-caryophyllene (13.1 ± 1.7%), cluster II by α-pinene (38.9 ± 2.4%) and germacrene D (19.1 ± 3.6%), while the prevalent compound of cluster III is α-pinene (51.9 ± 5.3%), followed by β-pinene (11.7 ± 1.7%) and germacrene D (10.7 ± 2.2%). The oil samples S10, S26 and S36 demonstrated antioxidant activity (DPPH: EC50 = 43.8 ± 1.0, 28.5 ± 1.0 and 38.8 ± 1.0 µg/mL, respectively; ABTS: TEAC = 17.16 ± 0.70, 23.35 ± 1.32 and 18.76 ± 0.64 µmol TE/mg EO, respectively) and anti-inflammatory activity through the LOX inhibition assay (IC50 = 34.9 ± 1.0, 32.1 ± 1.0 and 22.2 ± 1.0 µg/mL, respectively). The activities of A. rudis LEO may be related to its main compounds and thymol, all known for their various pharmacological and biological properties, and probably to synergistic effects.
The leaf and flower essential oils from Cyanthillium cinereum (Asteraceae), growing wild in C & ocirc;te d'Ivoire were investigated, using a combination of chromatographic [CC, GC(RI)] and spectroscopic [MS, 13C-NMR] techniques. A novel sesquiterpene identified as (E)-trans-beta-bergamotenal, was characterized. The oils from both plant parts were found to be rich in sesquiterpene hydrocarbons with concentration ranging from 78.4-87.6% in the flowers, and 72.1-91.8% in the leaves. In total, 43 constituents (91.5-96.7%) and 37 constituents (92.2-96.4%) were identified in the flower, and leaf oils, respectively. Major components of the flower oil were gamma-humulene (17.4-37.4%) and (E)-beta-caryophyllene (19.7-34.1%), followed by trans-beta-bergamotene (3.4-13.1%). The leaf oil composition was dominated by (E)-beta-caryophyllene (40.1-56.8%), with notable amounts of caryophyllene oxide (1.4-17.5%), germacrene D (1.8-11.4%), alpha-humulene (7.1-9.0%), guaia-6,10(14)-diene (3.6-8.9%) and gamma-humulene (0.3-5.9%). The hierarchical clustering analysis showed that flower and leaf essential oils from C & ocirc;te d'Ivoire are grouped in two distinct clusters and differed from samples collected in other countries.
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.
This research work concerns the comparative study of the chemical composition of essential oils from the aerial part of the Acanthospermum hispidium plant collected in three towns in Côte d'Ivoire. The aim of this study is to enhance the value of aromatic and medicinal plants through the chemical analysis of essential oils (EO). The essential oils extracted using a Clevenger-type apparatus were analysed using several analytical methods, including Ir-GPC, MS-GPC and 13C-NMR. The results indicate that the essential oils of Acanthospermum hispidium are largely dominated by hydrocarbon sesquiterpenes (69.2 to 72.9%). The majority compounds identified are (E)-β-caryophyllene (33.3 to 34.9%), α-bisabolol (6.5 to 9.9%), bicyclogermacrene (6, 3 to 9.5%), germacrene D (7.3 to 8.4%), α-pinene (4.6 to 7.9%), β-lemene (3.7 to 4.3%) and α-copaene (2.5 to 3.2%). The co-presence of these compounds with multiple pharmacological properties could justify the use of A. hispidium in traditional medicine in the treatment of various pathologies. Keywords: Acanthospermum hispidium, chemical composition, essential oil, Ivory Coast.
The misuse of synthetic pesticides in agrosystems has led to many problems including insect resistance and environmental pollution. To solve this problem, scientific research is increasingly focused on plants with insecticidal properties. Thus, this study has the general objective of evaluating the effectiveness of the various extracts (crude extract, fraction of extract, and essential oil) of Ocimum gratissimum on termites of the genus Nasutitermes, pests of cocoa trees. The crude extracts were obtained by the maceration of the dried leaf powders; the extract fractions by fractionation of the crude hydro-ethanolic extract and the essential oil by hydrodistillation. The tests, repeated four times, were carried out at the Animal Biology Laboratory of Felix Houphouet-Boigny University. Thus, 50 workers deposited in Petri dishes of termites were exposed to different doses of extracts of this plant and the effect of the extracts on termites as compared to the negative control. The results have shown that all the tested concentrations have scored the highest rate of mortality (100%) after 3 hours of exposure. This toxicity would be linked to the monoterpenes which constitute 80% of the compounds of this extract. However, by fumigation, the essential oil is effective at high concentrations (5 and 10 mg/l). Regarding extracts and fractions of extracts, only the acetate extract fraction showed a toxicity for termites. Nevertheless, this extract acts after 48 hours of exposure and at high concentrations.
The variability of chemical composition of the leaf essential oil (EO) from Neuropeltis acuminata, a climbing liana growing wild in Ivory Coast, was investigated for the first time. The in vitro anti-inflammatory activity was also evaluated. Thirty oil samples were isolated from leaves collected in three forests of the country and analyzed using a combination of Column Chromatography (CC), Gas Chromatography with Retention Indices (GC(FID)), Gas Chromatography-Mass Spectrometry (GC-MS), and 13Carbon-Nuclear Magnetic Resonance (13C-NMR). Fractionation by CC led to the first-time isolation from natural source of δ-cadinen-11-ol, whose structural elucidation by one dimension (1D) and 2D-NMR spectroscopy is reported here. Finally, 103 constituents accounting for 95.7 to 99.6% of the samples’ compositions were identified. As significant variations of the major constituents were observed, the 30 oil compositions were submitted to hierarchical cluster and principal components analyses. Five distinct groups were evidenced: Group I, dominated by (E)-β-caryophyllene, kessane, and δ-cadinene, while the main constituents of Group II were germacrene B, ledol, α-humulene, (E)-γ-bisabolen-12-ol, and γ-elemene. Group III exhibited guaiol, germacrene D, atractylone, (E)-γ-bisabolen-12-ol, δ-cadinene and bulnesol as main compounds. Group IV was dominated by (E)-nerolidol, guaiol, selina-4(15),7(11)-diene and bulnesol, whereas (E)-β-caryophyllene, α-humulene and α-muurolene were the prevalent compounds of Group V. As the harvest took place in the same dry season in the three forests, the observed chemical variability could be related to harvest sites, which includes climatic and pedologic factors, although genetic factors could not be excluded. The leaf oil sample S24 behaved as a high inhibitor of LipOXygenase (LOX) activity (half maximum Inhibitory Concentration, IC50: 0.059 ± 0.001 mg mL−1), suggesting an anti-inflammatory potential.
This work is a contribution to the characterization of aromatic and medicinal plants from Cote d'Ivoire. To date, no phytochemical investigation was reported onIsolona dewevrei. Thus, the aim of this study was to investigate for the first time, the chemical composition of the leaf essential oil fromI dewevrei. Two essential oil samples (S1, S2) were analysed by combination of chromatographic [GC(FID) and GC(RI)] and spectroscopic [MS,C-13-NMR] techniques. As several compounds remained unidentified, particularly in sample S1, this oil was fractionated on silica gel column, leading to the isolation and structural elucidation of four new natural compounds by QTOF-MS, 1D and 2D-NMR analyses. These new natural sesquiterpenes were identified as (5 alpha H,10 beta Me)-6,12-oxido-elema-1,3,6,11(12)-tetraene, 6,12-oxido-germacra-1(10),4,6,11(12)-tetraene, (1 beta H,5 beta H)-6,12-oxido-guaia-6,10(14),11(12)-trien-4 alpha-ol and germacra-1(10),4,7(11)-trien-6,12-gamma-lactone. Finally, sixty-eight constituents were identified in both investigated essential oil samples. They accounted for 96.1 and 97.3%, respectively, of the whole chemical composition of S1 and S2. Leaf essential oil fromIdewevreiis very rich in sesquiterpenes. Indeed, its majority compounds were germacrene B (20.8 and 24.8%), (5 alpha H,10 beta Me)-6,12-oxido-elema-1,3,6,11(12)-tetraene (10.3 and 0.3%, new compound), germacrene D (7.5 and 17.8%), (Z)-beta-ocimene (7.8 and 9.7%),gamma-elemene (6.9 and 7.5%) and (E)-beta-caryophyllene (6.8 and 3.5%). The contents of thermolabile components were assessed by combination of GC(FID) and(13)C-NMR.
The chemical variability and the in vitro anti-inflammatory activity of the leaf essential oil from Ivorian Isolona dewevrei were investigated for the first time. Forty-seven oil samples were analyzed using a combination of CC, GC(RI), GC-MS and 13C-NMR, thus leading to the identification of 113 constituents (90.8–98.9%). As the main components varied drastically from sample to sample, the 47 oil compositions were submitted to hierarchical cluster and principal components analyses. Three distinct groups, each divided into two subgroups, were evidenced. Subgroup I−A was dominated by (Z)-β-ocimene, β-eudesmol, germacrene D and (E)-β-ocimene, while (10βH)-1β,8β-oxido-cadina-4-ene, santalenone, trans-α-bergamotene and trans-β-bergamotene were the main compounds of Subgroup I−B. The prevalent constituents of Subgroup II−A were germacrene B, (E)-β-caryophyllene, (5αH,10βMe)-6,12-oxido-elema-1,3,6,11(12)-tetraene and γ-elemene. Subgroup II−B displayed germacrene B, germacrene D and (Z)-β-ocimene as the majority compounds. Germacrene D was the most abundant constituent of Group III, followed in Subgroup III−A by (E)-β-caryophyllene, (10βH)-1β,8β-oxido-cadina-4-ene, germacrene D-8-one, and then in Subgroup III−B by (Z)-β-ocimene and (E)-β-ocimene. The observed qualitative and quantitative chemical variability was probably due to combined factors, mostly phenology and season, then harvest site to a lesser extent. The lipoxygenase inhibition by a leaf oil sample was also evaluated. The oil IC50 (0.020 ± 0.005 mg/mL) was slightly higher than the non-competitive lipoxygenase inhibitor NDGA IC50 (0.013 ± 0.003 mg/mL), suggesting a significant in vitro anti-inflammatory potential.
The root and stem bark essential oils from Isolona dewevrei (Annonaceae), growing wild in Côte d’Ivoire, were investigated for the first time, using a combination of chromatographic [CC, GC(RI)] and spectroscopic [MS, 13C-NMR] techniques. A new natural germacrone was isolated by repetitive column chromatography carried out on a stem bark oil sample. Its structure was elucidated as germacra-1(10),4(15),5-trien-8-one by 1 D, 2 D-NMR and QTOF-MS. Ninety-six components accounting for 95.5 ± 0.8% and 95.8 ± 1.0%, respectively, for the root and stem bark essential oil samples were identified. The major compounds of root oil were cyperene (19.7 ± 1.6%) and camphene (10.1 ± 2.1%), followed by 5-isopentenylindole (6.4 ± 2.4%), β-elemene (3.9 ± 0.3%), (Z)-α-bisabolene (3.2 ± 1.2%) and γ-gurjunene (3.2 ± 0.3%). The stem bark oil was also dominated by cyperene (29.2 ± 4.1%), followed by β-elemene (6.2 ± 1.1%), (Z)-α-bisabolene (3.8 ± 1.0%), (E)-β-caryophyllene (3.3 ± 0.7%) and α-copaene (2.8 ± 1.1%).
The chemical composition of 44 leaf oil samples of Laggera pterodonta (DC.) Sch.Bip. ex Oliv. (Asteraceae) from Cote d'Ivoire was investigated, using combination of chromatographic (GC-FID) and spectroscopic (GC/MS, C-13-NMR) techniques. Two oil samples chosen according to their chromatographic profiles were submitted to column chromatography and all fractions of CC were analyzed by GC-FID, GC/MS and C-13-NMR. In total, 83 components accounting for 96.5 to 99.4 % of the whole chemical composition were identified. Significant variations were observed within terpene classes: monoterpene hydrocarbons (0.4-22.7 %), oxygenated monoterpenes (32.9-54.9 %), sesquiterpene hydrocarbons (18.6-38.3 %) and oxygenated sesquiterpenes (3.5-38.4 %). Thus, the 44 compositions were subjected to hierarchical cluster analysis (HCA) and principal component analysis (PCA). Two groups were differentiated according to their composition. All the samples contained 2,5-dimethoxy-p-cymene, alpha-humulene and (E)-beta-caryophyllene among the main components. Other components were present at appreciable contents and allowed differentiation of two groups: sabinene and germacrene D for Group I; 10-epi-gamma-eudesmol and eudesm-7(11)-en-4 alpha-ol for Group II. All the samples collected in Eastern Cote d'Ivoire constituted Group I, while samples collected in the Central area of the country constituted Group II.
This study aimed to investigate the chemical composition of the leaf essential oil from Ivoirian Isolona dewevrei. A combination of chromatographic and spectroscopic techniques (GC(RI), GC-MS and 13C-NMR) was used to analyze two oil samples (S1 and S2). Detailed analysis by repetitive column chromatography (CC) of essential oil sample S2 was performed, leading to the isolation of four compounds. Their structures were elucidated by QTOF-MS, 1D and 2D-NMR as (10βH)-1β,8β-oxido-cadin-4-ene (38), 4-methylene-(7αH)-germacra-1(10),5-dien-8β-ol (cis-germacrene D-8-ol) (52), 4-methylene-(7αH)-germacra-1(10),5-dien-8α-ol (trans-germacrene D-8-ol) (53) and cadina-1(10),4-dien-8β-ol (56). Compounds 38, 52 and 53 are new, whereas NMR data of 56 are reported for the first time. Lastly, 57 constituents accounting for 95.5% (S1) and 97.1% (S2) of the whole compositions were identified. Samples S1 and S2 were dominated by germacrene D (23.6 and 20.5%, respectively), followed by germacrene D-8-one (8.9 and 8.7%), (10βH)-1β,8β-oxido-cadin-4-ene (7.3 and 8.7), 4-methylene-(7αH)-germacra-1(10),5-dien-8β-ol (7.8 and 7.4%) and cadina-1(10),4-dien-8β-ol (7.6 and 7.2%). Leaves from I. dewevrei produced sesquiterpene-rich essential oil with an original chemical composition, involving various compounds reported for the first time among the main components. Integrated analysis by GC(RI), GC-MS and 13C-NMR appeared fruitful for the knowledge of such a complex essential oil.
The combination of 13C nuclear magnetic resonance (NMR) spectroscopy, gas chromatography (GC) (retention index), and gas chromatography-mass spectrometry was used to determine the chemical composition of essential oils of Piper guineense and Piper umbellatum from Côte d’Ivoire. Thus, 54 components, accounting for 91.5% to 97.6%, were identified in the essential oil from aerial parts of P. guineense. In P. umbellatum leaf oil, 49 compounds accounting for 92.8% to 98.7% were identified. Both plants oils were dominated by monoterpenes and sesquiterpenes, with α-phellandrene, (2 E,6 E)-farnesol, and linalool as major compounds of P. guineense, whereas the most abundant components of P. umbellatum were linalool and ( E)-β-caryophyllene. (2 E,6 E)-Farnesol, identified for the first time in the essential oil from aerial parts of P. guineense, induced a new chemical composition.
The investigation of the stem essential oil of Laggera pterodonta (DC.) Sch. Bip. ex Oliv. (Asteraceae) from Côte d’Ivoire was carried out, using a combination of chromatographic (GC-RI, CC, pc-GC) and spectroscopic (GC-MS, 13C NMR) techniques. This study led to the identification of fifty constituents of which two new natural compounds 7β,11β-epoxy-eudesman-4α-ol and 7α,11α-epoxy-eudesman-4α-ol. Their structures were elucidated by 1 D and 2 D NMR spectroscopy after pc-GC purifying. Finally, 98.9% of the whole composition of the oil was identified with a high amount of 2,5-dimethoxy-p-cymene (78.9%). The other significant components were α-humulene (6.2%), (E)-β-caryophyllene (1.7%), thymyl methyl oxide (1.7%), α-phellandrene (1.5%), p-cymene (1.2%), (3αH,4βH,6αH,1αMe)-1,6-epoxy-3-hydroxycarvotanacetone angelic acid ester (1.1%) and 10-epi-γ-eudesmol (1.0%).
Root and flower essential oils of Cyanthillium cinereum (L.) H. Rob. (Synonym Vernonia cinerea (L.) Less.) (Asteraceae) collected in Southern Côte d’Ivoire was investigated using a combination of chromatographic and spectroscopic techniques. The root oil composition was dominated by trans–β–bergamotene (20.7%), β–elemene (19.0%), cyperene (10.6%), germacrene A (7.1%) and β–pinene (3.8%), whereas γ–humulene (31.0%), (E)–β–caryophyllene (17.0%), trans–β–bergamotene (7.7%), β–pinene (7.5%) and (E)–β–farnesene (6.0%) were the major components of flower oil. Two new compounds bearing the trans–β–bergamotene framework were identified: trans–β–bergamotenone and (E)–trans–β–bergamotenol.
The leaf essential oil of Laggera pterodonta (DC.) Sch. Bip. ex Oliv. (Asteraceae) collected in the Eastern Côte d’Ivoire was investigated using a combination of chromatographic (GC-RI, CC, pc-GC) and spectroscopic (GC-MS, 13C NMR) techniques. Eighty-three components accounting for 98.0% of the whole composition were identified with 2,5-dimethoxy-p-cymene (43.3%), sabinene (14.1%), α-humulene (9.8%), (E)-β-caryophyllene (7.2%) and germacrene D (5.2%) as major compounds. This study led to the structural elucidation of a new natural compound, (3αH,4βH,6αH,1αMe)-1,6-epoxy-3-hydroxycarvotanacetone, angelic acid ester from the leaf oil by 1D and 2D NMR spectroscopy.
Nine samples of Xylopia rubescens Oliv. (Annonaceae) trunk bark oil have been analyzed by combination of GC(RI) and 13C NMR. The contents of the major components varied substantially from sample to sample: (8Z,11Z,14Z)-heptadeca-8,11–14-trien-2-one (14.7–33.0%), furanoguaia-1,4-diene (0–36.8%) and β-pinene (0.9–29.0%). The content of a few components reached punctually an appreciable amount: α-pinene (up to 10.7%), germacrene D (up to 12.0%), bicyclogermacrene (up to 10.0%) and spathulenol (up to 10.0%). X. rubescens trunk bark oil displayed a fair chemical variability.
The leaves and stem of Zanthoxylum rubescens Planck ex Hook. f. growing in Cote d'Ivoire, were submitted to hydrodistillation using a Clevenger type apparatus. Three different localities have been chosen for our investigations, namely Petit Yapo, Anguededou and Grand-Lahou. The oil obtained was investigated by GC(RI), GC-MS and C-13 NMR. Twenty-nine compounds were identified accounting for 81.8-95.2 % in the oil. The leaves oil composition was dominated by (E)-beta-caryophyllene (39.3-60.3 %), (E)-nerolidol (32.2 %) accompanied with significant contents of thymol, alpha-humulene and beta-sesquiphellandrene. While (E)-nerolidol (39.4 %) added to caryophyllene oxide (6.9 %) and thymol (6.7 %) were the major components of stem oil.
The leaves and stem of Zanthoxylum lepreurii were collected in two localities of Cote d'Ivoire, namely San-Pedro (South-east) and Adzope (South). The collects were submitted to hydrodistillation with the Clevenger apparatus. The oils obtained were investigated by C-13 NMR spectroscopy, GC (RI) and GC-MS. Thus, twenty-eight components accounting for 90.9-96.8 % were identified. Essential oils from leaves and stem bark of Z. leprieurii exhibited the predominance of two acyclic ketones. Undecan-2-one and tridecan-2-one have been identified as the main components. Undecan-2-one was found in abundance in the stem (30.3 %) and the leaves (10.0 %) respectively in Adzope and San-Pedro, while tridecan-2-one characterized all the samples (15.5 %-77.2 %). In addition with monoterpenoids and sesquiterpenoids identified as major components led to the new chemotypes of Z. leprieurii essential oil.