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1.
Nat Prod Res ; 33(9): 1383-1386, 2019 May.
Article in English | MEDLINE | ID: mdl-29783892

ABSTRACT

A chemical study of the volatile components obtained by applying the hydrodistillation and reflux processes to Pentadiplandra brazzeana roots was performed by GC-FID and GC-MS. The hydrodistillation process showed a total yield of 0.97% with 0.11% of essential oil and 0.86% of volatile compounds from the aqueous reaction medium; in the reflux process, the volatile extract yield was 1.03%. Benzylic-type isothiocyanates were the major degradation products of glucosinolates in the essential oil (95.0%); the CH2Cl2 extracts obtained from the aqueous solutions were characterised by alcohols and amines in both processes. This study has shown that during hydrodistillation, only 10% of the glucosinolate degradation products are recovered in the essential oil whereas 90% remain in the aqueous medium, being converted into alcohols and amines. The relative percentages of the different chemical classes recovered in our experimental conditions are discussed in relation with the glucosinolate composition in the raw material.


Subject(s)
Distillation/methods , Magnoliopsida/chemistry , Oils, Volatile/isolation & purification , Plant Roots/chemistry , Gas Chromatography-Mass Spectrometry , Glucosinolates/chemistry , Isothiocyanates/analysis , Isothiocyanates/chemistry , Oils, Volatile/chemistry , Plant Extracts/analysis , Plant Extracts/chemistry
2.
Nat Prod Res ; 31(3): 308-313, 2017 Feb.
Article in English | MEDLINE | ID: mdl-27858487

ABSTRACT

Drypetes euryodes (Hiern) Hutch., Drypetes gossweileri S. Moore, Drypetes laciniata Hutch. (Putranjivaceae), Rinorea subintegrifolia O. Ktze, and Rinorea woermanniana (Büttner) Engl. (Violaceae) from Gabon were probed for the presence of glucosinolates (GLs). When present, the GLs were identified and quantified by HPLC analysis. 2-Hydroxy-2-methyl GL (1) was the major GL in the cork of D. euryodes. Moreover, 4-hydroxybenzyl GL (2) was the major GL in the seed of D. gossweileri whereas the bark contained 2 as the minor GL and benzyl GL (3) was the major one. In addition, 4-methoxybenzyl GL (4), 3-methoxybenzyl GL (5), and 3 were found in the root of R. subintegrifolia. However, no GL was detected in D. laciniata (leaf and stem), D. euryodes (leaf and stem), and R. woermanniana (leaf and stem-branch). Our results support the hypothesis of the existence of GLs in plants of the Putranjivaceae and Violaceae families (order Malpighiales).


Subject(s)
Glucosinolates/analysis , Magnoliopsida/chemistry , Chromatography, High Pressure Liquid/methods , Gabon , Glucosinolates/chemistry , Glucosinolates/isolation & purification , Plant Bark/chemistry , Plant Extracts/chemistry , Plant Leaves/chemistry , Plant Roots/chemistry , Seeds/chemistry
3.
J Ethnopharmacol ; 194: 587-594, 2016 Dec 24.
Article in English | MEDLINE | ID: mdl-27765608

ABSTRACT

ETHNOPHARMACOLOGICAL RELEVANCE: Lippia multiflora is a plant with nutritional and pharmaco-therapeutic properties that is native to central and occidental Africa. The potential effects of plants on health are associated with their chemical composition. Therefore, the present study aimed to identify chemical variations in essential oils of Lippia multiflora as a function of geographic origin and time of annual harvest to determine optimal chemical profiles for ethno-pharmacotherapeutic applications. MATERIALS AND METHODS: Experimental plants were cultivated at Abidjan (LPA), Toumodi (LPT) and Bondoukou (LPB). Natural Lippia multiflora seeds were sourced to produce standardized plants over a period of six months. Standard plants (n=40) were re-introduced into natural plots, cultivated for 12 months and leaves were sampled monthly in a standardized fashion. Essentials oils (n=36) were then extracted from these samples by hydro-distillation according to the European Pharmacopoeia and qualitatively and quantitatively analyzed using GC/FID and GC/MS. These data were then analyzed using Principal Component Analysis (PCA). Anti-inflammatory properties were also assessed against activated macrophages in vitro. RESULTS: The results indicated that chemical profiles and essential oil yields vary according to the location where the plants were cultivated. One essential oil chemotype corresponded to the LPA and LPT sites and one corresponded to the LPB site. Statistical analysis of the chemical profiles and monthly evolution of the three sites over a period of one year allowed assessment of variations in composition and the subsequent choice of the optimal harvest time for ethnopharmacological applications. Anti-inflammatory activity apparently correlated with chemical profiles of essential oils and the geographic origins of the plants. CONCLUSION: The optimal harvest time was associated with the maximum yield of pharmacological compounds with the most potential interest for health.


Subject(s)
Anti-Inflammatory Agents/pharmacology , Geography , Lippia/chemistry , Oils, Volatile/pharmacology , Plant Leaves/chemistry , Seasons , Animals , Cell Line
4.
BMC Complement Altern Med ; 16: 71, 2016 Feb 22.
Article in English | MEDLINE | ID: mdl-26906899

ABSTRACT

BACKGROUND: Diabetes mellitus is a metabolic disorder which is rising globally in rich and developing countries. In the African region this rate is the highest, with 20 million diagnosed diabetics. Despite a noticeable progress in the treatment of diabetes mellitus by synthetic drugs, the search for new natural anti-diabetic agents is going on. Nauclea diderrichii (De Wild.) Merr. (ND) and Sarcocephalus pobeguinii Hua ex Pellegr. (SP) are used as traditional medicines in Gabon for the treatment of different diseases, especially in the case of diabetes. The aim of this study was to evaluate the antidiabetic potential of these two medicinal plants traditionally used in Gabon. METHODS: Pharmacological (inhibitory action on α and ß-glucosidases) and toxicological (effect on human T cell proliferation) studies were conducted on aqueous extracts of ND (leaves and bark) and SP (bark) collected in Gabon. All raw extracts were analyzed by HPTLC and their content in phenolic compounds was determined by using standard method. The most active extracts were submitted to preparative HPLC in order to evidence the most efficient subfractions by biological evaluation. RESULTS: The results showed that two extracts from ND were potent α-glucosidase inhibitors, the leaf extract being more active that the bark extract: the first one was more than 60 fold more active than Acarbose, which is an oral medication used to treat type 2 diabetes; the extract from SP bark was less efficient. The HPLC subfractions of the extracts of ND leaves and SP bark were tested in the same experimental conditions. In each case, the most active subfractions still show very potent inhibitory effect on α-glucosidase (80-90% inhibition at 0.1 mg/mL). The most efficient extract, from ND leaves, was also characterized by the highest percentage of phenolic compounds, which suggests a relationship between its inhibitory potential on α-glucosidase and its content in phenolic compounds. Conversely, only a moderate inhibitory activity of the three extracts was observed on ß-glucosidase. CONCLUSION: These results clearly indicated that active compounds present in N. diderrichii and S. pobeguinii leaves or/and bark were selective and highly potent inhibitors of α-glucosidase and validate their popular use for the treatment of diabetes.


Subject(s)
Diabetes Mellitus/metabolism , Glycoside Hydrolase Inhibitors/pharmacology , Hypoglycemic Agents/pharmacology , Phenols/pharmacology , Plant Extracts/pharmacology , Rubiaceae/chemistry , alpha-Glucosidases/metabolism , Chromatography, High Pressure Liquid , Diabetes Mellitus/drug therapy , Gabon , Glycoside Hydrolase Inhibitors/therapeutic use , Humans , Hypoglycemic Agents/therapeutic use , Medicine, African Traditional , Phenols/therapeutic use , Phytotherapy , Plant Bark , Plant Extracts/therapeutic use , Plant Leaves
5.
Food Chem ; 197(Pt A): 965-71, 2016 Apr 15.
Article in English | MEDLINE | ID: mdl-26617041

ABSTRACT

The role of 1-pyrroline was studied via feeding experiments using rice calli cultures to gain further insight into the key steps of 2-acetyl-1-pyrroline (2AP) biosynthesis in rice. The origin of the acetyl donor was also studied through stable isotope labelled substrates. Incubation of fresh calli from a fragrant rice variety (Aychade) and a non-fragrant variety (Gladio×Fidji K2) with 1-pyrroline led to a significant increase in 2AP in both varieties. Importantly, the amount of 2AP in the non-fragrant variety could be greatly enhanced by this supplementation. When rice calli were fed with increasing levels of 1-pyrroline, 2AP levels increased accordingly. Our data show that 1-pyrroline is a limiting factor for 2AP synthesis in rice. Heat treatment of calli suggested that 1-pyrroline might be enzymatically acetylated. The presence of labelled 2AP in calli supplemented with [U-(13)C]glucose, sodium acetate (1,2-(13)C2) and sodium octanoate (1,2,3,4-(13)C4) suggested that these compounds are possible candidates for acetyl group-donors of 2AP, predominately in the form of intact labelled (13)C2-units.


Subject(s)
Oryza/metabolism , Plant Extracts/metabolism , Pyrroles/metabolism , Odorants/analysis
6.
Pest Manag Sci ; 72(1): 179-89, 2016 Jan.
Article in English | MEDLINE | ID: mdl-25641934

ABSTRACT

BACKGROUND: In tropical countries, netting is an effective sustainable tool for protecting horticultural crops against Lepidoptera, although not against small pests such as Bemisia tabaci, while smaller mesh netting can be used in temperate regions. A solution is to combine a net with a repellent. Previously we identified repellent essential oils: lemongrass (Cymbopogon citratus), cinnamon (Cinnamomum zeylanicum), cumin (Cuminum cyminum) and citronella (Cymbopogon winternarius). The present study was designed to identify the active compounds of these essential oils, characterise their biological activity and examine their potential for coating nets. We investigated the efficiency and toxicity of nets dipped in different solutions. We then studied the repellent effect with an olfactometer and the irritant effect by videotracking. RESULTS: Geraniol and citronellol were the most promising net coatings owing to their repellent effect. The repellency, irritancy or toxicity varied with the product and concentration, and these features were independent, indicating that the repellent and the irritant/toxic mechanisms were not the same. The combined effects of these different compounds account for the bioactivity of the mixture, suggesting interactions between the compounds. CONCLUSION: This new sustainable strategy for protecting vegetable crops against whiteflies is discussed, in addition to the use of companion plants that could produce such bioactive compounds.


Subject(s)
Cinnamomum zeylanicum/chemistry , Cuminum/chemistry , Cymbopogon/chemistry , Hemiptera , Insect Repellents , Oils, Volatile , Animals , Female , Male
7.
Chem Biodivers ; 12(12): 1848-61, 2015 Dec.
Article in English | MEDLINE | ID: mdl-26663838

ABSTRACT

Plant secondary metabolites can be useful chemosystematic markers to distinguish species at different taxonomy levels. For example, sesquiterpenes and diterpenes show specific distribution patterns within conifers and so provide especially precious information about the diversity and evolutionary relationships of this group. The aim of the present study was to provide a first insight into the terpene diversity of endemic Podocarpaceae from New Caledonia. The leaf essential oils of Dacrydium araucarioides Brongn. & Gris, Dacrydium balansae Brongn. & Gris, Dacrydium guillauminii J.Buchholz, Dacrydium lycopodioides Brongn. & Gris, Falcatifolium taxoides (Brongn. & Gris) de Laub., and Acmopyle pancheri (Brongn. & Gris) Pilg. from New Caledonia were characterized by GC/FID and GC/MS analyses, and the chemotaxonomic relationships of these species were determined by comparison of their terpene compositions. Cluster analysis based on the biosynthetic origin of their volatile terpenes led to the description of three distinct groups of essential oils and showed close relationships between those of D. araucarioides and D. balansae as well as between those of A. pancheri and F. taxoides.


Subject(s)
Oils, Volatile/chemistry , Plant Leaves/chemistry , Tracheophyta/chemistry , Molecular Structure , New Caledonia , Oils, Volatile/isolation & purification , Species Specificity , Terpenes/chemistry , Tracheophyta/classification
8.
J Econ Entomol ; 108(4): 1890-901, 2015 Aug.
Article in English | MEDLINE | ID: mdl-26470332

ABSTRACT

In the Mediterranean region, the use of small-mesh netting to protect horticultural crops is an effective sustainable tool against pests. But in tropical regions, because of high humidity under the net favoring fungal development, netting with a larger mesh size has to be used, protecting crops against lepidopteran pests but not against small pests such as hemipterans, thrips, and phytophagous mites. A combination of netting with a repellent or irritant product is one possible solution, but the desire to reduce the use of synthetic chemicals and mitigate resistance issues calls for a natural alternative. The objective of this study was to evaluate the repellent, irritant, and toxic effects of nets dipped in 20 different plant extracts on Bemisia tabaci (Gennadius) adults. The repellent effect of volatile compounds was evaluated using a still-air olfactometer. The irritant effect and toxicity were evaluated with a no-choice test in tubes separated into two parts by an impregnated net. Our results showed the seven most irritant and toxic products against B. tabaci were aframomum, cinnamon, geranium, dill, citronella, litsea, and savory. The most repellent were aframomum and lemongrass, although cinnamon, geranium, and savory were also repellent at higher doses. Effects varied with the plant extract and the concentration, and effects were independent of one another, i.e., an essential oil can be irritant but not repellent, suggesting that the repellent mechanism and that behind the irritant or toxic effects is not the same. The use of repellent compounds in combination with netting as new pest control strategy is discussed.


Subject(s)
Hemiptera/drug effects , Insect Repellents/pharmacology , Insecticides/pharmacology , Plant Extracts/pharmacology , Animals , Chemotaxis , Female , Hemiptera/physiology , Male
9.
Parasit Vectors ; 8: 316, 2015 Jun 11.
Article in English | MEDLINE | ID: mdl-26063119

ABSTRACT

BACKGROUND: Laboratory and field studies showed that repellent, irritant and toxic actions of common public health insecticides reduce human-vector contact and thereby interrupt disease transmission. One of the more effective strategies to reduce disease risk involves the use of long-lasting treated bednets. However, development of insecticide resistance in mosquito populations makes it imperative to find alternatives to these insecticides. Our previous study identified four essential oils as alternatives to pyrethroids: Thymus vulgaris, Cymbopogon winterianus, Cuminum cyminum, Cinnamomum zeylanicum. The objectives of this study were to identify active compounds of these essential oils, to characterize their biological activity, and to examine their potential as a treatment for bednets. METHODS: We evaluated the electrophysiological, behavioural (repellency, irritancy) and toxic effects of the major compounds of these oils against Anopheles gambiae strain 'Kisumu'. RESULTS: Aldehydes elicited the strongest responses and monoterpenes the weakest responses in electroantennogram (EAG) trials. However, EAG responses did not correlate consistently with results of behavioral assays. In behavioral and toxicity studies, several of the single compounds did exhibit repellency, irritancy or toxicity in An. gambiae; however, the activity of essential oils did not always correlate with activity expected from the major components. On the contrary, the biological activity of essential oils appeared complex, suggesting interactions between individual compounds and the insect under study. Data also indicated that the three effects appeared independent, suggesting that repellency mechanism(s) may differ from mechanisms of irritancy and toxicity. CONCLUSIONS: Based on the bioassays reported here, some of the compounds merit consideration as alternative bednet treatments.


Subject(s)
Anopheles/drug effects , Cinnamomum zeylanicum/chemistry , Cuminum/chemistry , Cymbopogon/chemistry , Insecticides/pharmacology , Oils, Volatile/pharmacology , Plant Oils/pharmacology , Thymus Plant/chemistry , Animals , Anopheles/physiology , Behavior, Animal/drug effects , Insect Control/instrumentation , Insect Control/methods , Insecticide-Treated Bednets , Insecticides/chemistry , Oils, Volatile/chemistry , Plant Oils/chemistry
10.
Nat Prod Commun ; 9(2): 261-4, 2014 Feb.
Article in English | MEDLINE | ID: mdl-24689305

ABSTRACT

This study aimed to compare the chemical composition of volatile extracts obtained by hydrodistillation of leaves, stems, bark and roots of Uvariodendron angustifolium (Engl. & Diels) R. E. Fries. The essential oils, obtained with yields between 0.12 and 0.66%, were analyzed by GC/FID and GC/MS. A great variability in the chemical composition was observed depending on the plant part treated. The essential oils obtained from leaves and stems contained mainly neral (29.7-30.5%) and geranial (42.9-47.3%), while methyl eugenol was the major component of the volatile extracts from bark (68.3%) and roots (85.3%). Interesting cytotoxic properties of these essential oils on human breast cancer cells MCF-7 were demonstrated.


Subject(s)
Annonaceae/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Oils, Volatile/analysis , Oils, Volatile/pharmacology , Benin , Gas Chromatography-Mass Spectrometry , Humans , MCF-7 Cells , Plant Extracts/analysis
11.
BMC Complement Altern Med ; 14: 125, 2014 Apr 04.
Article in English | MEDLINE | ID: mdl-24708588

ABSTRACT

BACKGROUND: Cancer has become a global public health problem and the search for new control measures is urgent. Investigation of plant products such as essential oils from Monodora myristica, Xylopia aethiopica and Xylopia parviflora might lead to new anticancer therapy. In this study, we have investigated the antineoplastic activity of essential oils from fruits of these plants growing in Chad and Cameroon. METHODS: The essential oils obtained by hydrodistillation of fruits of Monodora myristica, Xylopia aethiopica and Xylopia parviflora collected in Chad and Cameroon were analyzed by GC-FID and GC-MS and investigated for their antiproliferative activity against the breast cancer cell line (MCF7). RESULTS: Overall, monoterpenes were mostly found in the six essential oils. Oils from X. aethiopica and X. parviflora from Chad and Cameroon mainly contain ß-pinene at 24.6%, 28.2%, 35.7% and 32.9% respectively. Monodora myristica oils from both origins contain mainly α-phellandrene at 52.7% and 67.1% respectively. The plant origin did not significantly influence the chemical composition of oils. The six essential oils exerted cytotoxic activity against cancer (MCF-7) and normal cell lines (ARPE-19), with more pronounced effect on neoplastic cells in the majority of cases. The highest selectivity was obtained with the essential oils of X. parviflora from Chad and Cameroon (5.87 and 5.54) which were more cytotoxic against MCF-7 than against normal cell line (ARPE-19) with IC50 values of 0.155 µL/mL and 0.166 µL/mL respectively. CONCLUSIONS: Essential oils from fruits of Monodora myristica, Xylopia aethiopica and Xylopia parviflora have shown acceptable antineoplastic potency, and might be investigated further in this regard.


Subject(s)
Annonaceae/chemistry , Antineoplastic Agents, Phytogenic/therapeutic use , Breast Neoplasms/drug therapy , Oils, Volatile/therapeutic use , Phytotherapy , Plant Extracts/therapeutic use , Xylopia/chemistry , Antineoplastic Agents, Phytogenic/analysis , Antineoplastic Agents, Phytogenic/pharmacology , Bicyclic Monoterpenes , Bridged Bicyclo Compounds/analysis , Bridged Bicyclo Compounds/pharmacology , Bridged Bicyclo Compounds/therapeutic use , Cameroon , Cell Line , Chad , Cyclohexane Monoterpenes , Fruit , Humans , MCF-7 Cells , Monoterpenes/analysis , Monoterpenes/pharmacology , Monoterpenes/therapeutic use , Oils, Volatile/chemistry , Oils, Volatile/pharmacology , Plant Extracts/chemistry , Plant Extracts/pharmacology
12.
Chem Biodivers ; 11(2): 323-31, 2014 Feb.
Article in English | MEDLINE | ID: mdl-24591320

ABSTRACT

The effect of the distillation time on the yield and chemical composition of the bark essential oil of Cedrelopsis grevei Baill. was investigated. Distillation kinetics were determined for three batches of bark sampled from two sites, i.e., Itampolo (batches IT1 and IT2) and Salary (SAL), located in a region in the south of Madagascar with characteristically large populations of C. grevei. The bark samples were subjected to steam distillation, and the essential oil was collected at 3-h intervals. The total yield (calculated after 14 h of distillation) varied from 0.9 to 1.7%, according to the batch tested. Moreover, the essential oils obtained were characterized by GC-FID and GC/MS analyses. During the course of the distillation, the relative percentages of the most volatile components (monoterpenes and sesquiterpene hydrocarbons) diminished progressively, whereas the least volatile ones (oxygenated derivatives) increased at a consistent rate. Principal component analysis (PCA) and agglomerative hierarchical clustering analysis (AHC) of the results, performed on 13 principal components, allowed distinguishing three chemical groups, corresponding to the three batches, irrespective of the distillation time. This indicated that the chemical variability currently observed with commercial samples is not mainly linked to the experimental conditions of the extraction process, as the distillation time did not significantly alter the chemical composition of the essential oils.


Subject(s)
Oils, Volatile/chemistry , Plant Bark/chemistry , Rutaceae/chemistry , Madagascar , Oils, Volatile/isolation & purification , Principal Component Analysis
13.
PLoS One ; 8(12): e82103, 2013.
Article in English | MEDLINE | ID: mdl-24376515

ABSTRACT

Pyrethroid insecticides induce an excito-repellent effect that reduces contact between humans and mosquitoes. Insecticide use is expected to lower the risk of pathogen transmission, particularly when impregnated on long-lasting treated bednets. When applied at low doses, pyrethroids have a toxic effect, however the development of pyrethroid resistance in several mosquito species may jeopardize these beneficial effects. The need to find additional compounds, either to kill disease-carrying mosquitoes or to prevent mosquito contact with humans, therefore arises. In laboratory conditions, the effects (i.e., repellent, irritant and toxic) of 20 plant extracts, mainly essential oils, were assessed on adults of Anopheles gambiae, a primary vector of malaria. Their effects were compared to those of DEET and permethrin, used as positive controls. Most plant extracts had irritant, repellent and/or toxic effects on An. gambiae adults. The most promising extracts, i.e. those combining the three types of effects, were from Cymbopogon winterianus, Cinnamomum zeylanicum and Thymus vulgaris. The irritant, repellent and toxic effects occurred apparently independently of each other, and the behavioural response of adult An. gambiae was significantly influenced by the concentration of the plant extracts. Mechanisms underlying repellency might, therefore, differ from those underlying irritancy and toxicity. The utility of the efficient plant extracts for vector control as an alternative to pyrethroids may thus be envisaged.


Subject(s)
Anopheles/drug effects , Anopheles/growth & development , Insect Repellents/toxicity , Insect Vectors/drug effects , Irritants/toxicity , Plant Extracts/toxicity , Aging/drug effects , Animals , Feeding Behavior/drug effects , Female , Insect Vectors/growth & development , Malaria/parasitology , Toxicity Tests
14.
Parasitol Res ; 112(4): 1379-84, 2013 Apr.
Article in English | MEDLINE | ID: mdl-23371495

ABSTRACT

The aim of the present study was to demonstrate acaricidal activity on the cattle tick Rhipicephalus (Boophilus) microplus of essential oils from endemic conifers of New Caledonia in the context of the development of natural alternatives. Acaricidal activity of essential oils extracted from resin and heartwood of five endemic conifers of New Caledonia (Araucaria columnaris, Agathis moorei, Agathis ovata, Callitris sulcata, and Neocallitropsis pancheri) was evaluated on 14- to 21-day-old Rhipicephalus microplus tick larvae using the Larval Packal Test bioassay. A first screening with 5% dilute solution was carried out and the oils with 100% of mortality at this rate were diluted until no activity was shown. The heartwood oils of the two Cupressaceae were the most active with LC50 value of 0.65% for C. sulcata and 0.55% for N. pancheri while resin oil of A. columnaris (LC50=1.62%) was the most active of the Araucariaceae family. Negative control (ethanol) was not toxic to the larvae. The chemical composition of essential oil from resin of A. columnaris was analyzed by gas chromatography-mass spectrometry. The essential oil was characterized by high level of sesquiterpene hydrocarbons and oxygenated sesquiterpenes and was composed mainly of aromadendrene (23.1%) and bicyclogermacrene (16.0%). In order to compare different plant resources in a sustainable program of natural acaricide, an "essential oil efficiency EOE" can be measured as the ratio between the yield of extraction and LC50 value. This study shows that A. columnaris (EOE=2.36) and N. pancheri (EOE=3.51) could provide valuable and effective natural acaricides for control of the cattle tick R. microplus.


Subject(s)
Acaricides/pharmacology , Oils, Volatile/pharmacology , Rhipicephalus/drug effects , Tracheophyta/chemistry , Acaricides/chemistry , Acaricides/isolation & purification , Animals , Biological Assay , Female , Gas Chromatography-Mass Spectrometry , Larva/drug effects , New Caledonia , Oils, Volatile/chemistry , Oils, Volatile/isolation & purification , Sesquiterpenes/analysis , Survival Analysis
15.
J Agric Food Chem ; 61(1): 137-42, 2013 Jan 09.
Article in English | MEDLINE | ID: mdl-23214966

ABSTRACT

Pentadiplandra brazzeana Baillon (Pentadiplandraceae) is known to contain benzyl-, 3-methoxybenzyl-, 4-methoxybenzyl-, 3,4-dimethoxybenzyl-, and indole-type glucosinolates, and the essential oil obtained from its roots is mainly constituted of benzyl isothiocyanate and benzyl cyanide. In a previous study by the authors, it was surmised that partial hydrolytic degradation of 4-methoxybenzyl isothiocyanate, one major expected compound, occurred during the hydrodistillation process of essential oil preparation. To probe this hypothesis, a selection of diversely substituted benzylic-type isothiocyanates was submitted to standard hydrodistillation-mimicking conditions. After extraction with dichloromethane, the reaction mixtures were analyzed using GC-MS. The aqueous phases resulting from liquid-liquid extraction were analyzed by HPLC and GC-MS. 2-Methoxybenzyl, 4-methoxybenzyl, 3,4-dimethoxybenzyl, and 3,4,5-trimethoxybenzyl isothiocyanates underwent conversion into 2-methoxybenzyl, 4-methoxybenzyl, 3,4-dimethoxybenzyl, and 3,4,5-trimethoxybenzyl alcohols, respectively, whereas benzyl, 3-methoxybenzyl, and 4-chlorobenzyl isothiocyanates were converted into the corresponding benzylamines.


Subject(s)
Isothiocyanates/chemistry , Chromatography, High Pressure Liquid , Gas Chromatography-Mass Spectrometry , Liquid-Liquid Extraction , Spectrum Analysis
16.
Phytochemistry ; 73(1): 51-6, 2012 Jan.
Article in English | MEDLINE | ID: mdl-21993210

ABSTRACT

Glucosinolates (GLs) present in root, seed, and leaf extracts of Pentadiplandra brazzeana Baillon were characterized and quantified according to the ISO 9167-1 method based on the HPLC analysis of desulfo-GLs. The analyses were complemented by GC-MS analyses of the isothiocyanates (ITCs) generated from GL degradation by myrosinase. Glucotropaeolin (1a), glucolimnanthin (2a), and glucoaubrietin (3a) were shown to be present in the root extract, whereas the seed mainly contained 3a. 3,4-Dimethoxybenzyl GL (4a), glucobrassicin (5a) and traces of 1a were detected in the leaf extract. The products were fully characterized as their desulfo-counterparts by spectroscopic techniques.


Subject(s)
Brassicaceae/chemistry , Glucosinolates/analysis , Indoles/chemistry , Isothiocyanates/chemistry , Cameroon , Chromatography, High Pressure Liquid , Glucosinolates/chemistry , Glucosinolates/metabolism , Indoles/analysis , Isothiocyanates/analysis , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Plant Leaves/chemistry , Plant Roots/chemistry , Seeds/chemistry
17.
Nat Prod Commun ; 6(8): 1183-8, 2011 Aug.
Article in English | MEDLINE | ID: mdl-21922931

ABSTRACT

Essential oils of aromatic plants with insecticidal properties are nowadays considered as alternative insecticides to protect cultures from attack by insect pest. The aims of the present work were to evaluate the toxicity of the essential oils vapors of two aromatic plants (Lippia multiflora Mold. and Aframomum latifolium K. Schum) against Bemisia tabaci and to characterize their chemical composition. The highest fumigant toxicity against B. tabaci adults was observed with the L. multiflora oil: by exposure to 0.4 microL/L air, the lethal time inducing 90% mortality (LT90) was below 2 hours for this essential oil whereas it reached 15 h in the case of the A. latifolium oil. Both oils were analyzed by GC-FID and GC-MS on two capillary columns. The oil of L. multiflora contained a majority of oxygenated terpenoids mainly represented by the two acyclic components linalool (46.6%) and (E)-nerolidol (16.5%); the oil of A. latifolium was dominated by hydrocarbonated terpenoids among them beta-pinene (51.6%) and beta-caryophyllene (12.3%) were the two major components.


Subject(s)
Hemiptera/drug effects , Insecticides/chemistry , Insecticides/pharmacology , Lippia/chemistry , Oils, Volatile/pharmacology , Zingiberaceae/chemistry , Animals , Cote d'Ivoire , Oils, Volatile/chemistry , Plant Oils/chemistry , Plant Oils/pharmacology
18.
Nat Prod Commun ; 6(9): 1367-71, 2011 Sep.
Article in English | MEDLINE | ID: mdl-21941917

ABSTRACT

Investigations were conducted to determine the chemical composition, antifungal and antiradical activities of the essential oil extracted from the fresh leaves of Clausena anisata (Willd.) Hook. F. ex Benth (from Cameroon) against Aspergillus flavus, A. niger, A. parasiticus and Fusarium moniliforme. The essential oil obtained by hydrodistillation was analysed by GC and GC/MS. The disc diffusion method was used to evaluate the fungal growth inhibition at various concentrations of the oil while the antiradical activity of the essential oil was studied by the DPPH (diphenyl picryl hydrazyl) method. The main components obtained were E-ocimenone (15.1%), Z-ocimenone (11.5%), gamma-terpinene (11.4%) and germacrene D (10.9%). After 10 days of incubation on essential oil supplemented medium, the growth of A. flavus, A. niger, A. parasiticus and F. moniliforme were totally inhibited by 4, 5, 5 and 5 mg/mL of C. anisata essential oil, respectively. The antiradical activity of C. anisata essential oil (SC50 = 5.1 g/L) was less than that of butylated hydroxyl toluene (BHT), which was used as the reference compound (SC50 = 0.007 g/L). Results obtained in the present study indicate the possibility of exploiting C. anisata essential oil to fight strains of A. flavus, A. niger, A. parasiticus and F. moniliforme responsible for biodeterioration of stored food products.


Subject(s)
Clausena/chemistry , Food Microbiology , Free Radical Scavengers/pharmacology , Fungi/drug effects , Oils, Volatile/pharmacology , Plant Oils/pharmacology , Antifungal Agents/chemistry , Antifungal Agents/pharmacology , Cameroon , Free Radical Scavengers/chemistry , Oils, Volatile/chemistry , Plant Oils/chemistry
19.
Nat Prod Commun ; 6(3): 409-16, 2011 Mar.
Article in English | MEDLINE | ID: mdl-21485283

ABSTRACT

Water distilled essential oils from leaves of Plectranthus tenuicaulis (Hook. f.) J. K. Morton collected in Gabon were analyzed using GC-FID and GC-MS. The main constituent, unusual within the genus Plectranthus, was isolated and formally identified as being the (+)-(R)-enantiomer of (E)-6,7-epoxyocimene [(E)-myroxide]. This enantiomer, which represents about 75% of the essential oil, has been previously identified as a pheromone emitted by the male fruit-spotting bug Amblypelta nitida; this insect is responsible of destruction of most fruit crops in tropical and subtropical areas. The potential application of P. tenuicaulis essential oil in crop protection programs is discussed and the atypical chemical profile of the gabonese essential oil is compared with those previously reported in the genus Plectranthus (or Coleus).


Subject(s)
Alkenes/chemistry , Oils, Volatile/chemistry , Plectranthus/chemistry , Chromatography, Liquid , Gabon , Gas Chromatography-Mass Spectrometry , Magnetic Resonance Spectroscopy , Plant Leaves/chemistry , Plectranthus/classification , Species Specificity
20.
Parasitol Res ; 108(5): 1211-7, 2011 May.
Article in English | MEDLINE | ID: mdl-21107862

ABSTRACT

In a search for alternative treatment for malaria, plant-derived essential oils extracted from the stem barks and leaves of Cleistopholis patens and Uvariastrum pierreanum (Annonaceae) were evaluated in vitro for antiplasmodial activity against the W2 strain of Plasmodium falciparum. The oils were obtained from 500 g each of stem barks and leaves, respectively, by hydrodistillation, using a Clevenger-type apparatus with the following yields: 0.23% and 0.19% for C. patens and 0.1% and 0.3% for U. pierreanum (w/w relative to dried material weight). Analysis of 10% (v/v) oil in hexane by gas chromatography and mass spectrometry identified only terpenoids in the oils, with over 81% sesquiterpene hydrocarbons in C. patens extracts and U. pierreanum stem bark oil, while the leaf oil from the latter species was found to contain a majority of monoterpenes. For C. patens, the major components were α-copaene, δ-cadinene, and germacrene D for the stem bark oil and ß-caryophyllene, germacrene D, and germacrene B for the leaf oil. The stem bark oil of U. pierreanum was found to contain mainly ß-bisabolene and α-bisabolol, while α- and ß-pinenes were more abundant in the leaf extract. Concentrations of oils obtained by diluting 1-mg/mL stock solutions were tested against P. falciparum in culture. The oils were active, with IC(50) values of 9.19 and 15.19 µg/mL for the stem bark and leaf oils, respectively, of C. patens and 6.08 and 13.96 µg/mL, respectively, for those from U. pierreanum. These results indicate that essential oils may offer a promising alternative for the development of new antimalarials.


Subject(s)
Annonaceae/chemistry , Antimalarials/pharmacology , Oils, Volatile/pharmacology , Plant Extracts/pharmacology , Plasmodium falciparum/drug effects , Antimalarials/chemistry , Antimalarials/isolation & purification , Cameroon , Gas Chromatography-Mass Spectrometry , Inhibitory Concentration 50 , Oils, Volatile/chemistry , Oils, Volatile/isolation & purification , Parasitic Sensitivity Tests , Plant Bark/chemistry , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Plant Leaves/chemistry
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