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The Essential Oil Composition of Dictamnus albus from Turkey

  • Medicinal Plant, Drug and Scientific Research and Application Center (AUBIBAM), Eskisehir, Turkey

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Semi-dried, flowering leafy branches were subjected to water distillation: three days after collection (A), and after fully drying for one year (B). The oils were separately analysed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC/MS) techniques. Twenty-one components were identified making up 97.87 % (A) and 94.70% (B) of both oils (Table 1). The main components in the oils were identified as dictagymnin [1-allyl-4-(3-methyl-3-butenyloxy)-benzene] (1), feniculin [l-(3-methyl-2-butenyloxy)-4-propylbenzene] (2), methylchavi-col (= estragole) (3), and frans-anethol (4). The amounts of dictagymnin and feniculin in oil from dried plant material analysed one year after collection were greater than in oil from semi-dried plant material, while the percentage amounts of methylchavicol and £ra/zs-anethol were lower. Dictagymnin was previously isolated only from the essential oil of the aerial parts of Caucasian D. gymnostylis Stev. with a 0.24% yield (6). Feniculin was previously characterized from Foeniculum vulgare Mill, (fennel) (7) and was identified in the oil of Illicium verum Hooker f. (star anis) (8). Dictagymnin and feniculin are prenyl ethers of chavicol and anol, respectively. Since authentic samples of dictagymnin and feniculin were not available for comparison, their identities were proven by a simple chemical experiment. The essential oil was sealed in a glass ampoule and left to stand at 260 °C for 1/2 hour. The subsequent GC/MS analysis of the oil revealed, as expected , the complete conversion of dictagymnin and feni-culin to chavicol (p-allylphenol) and anol (p-propenyl-phenol), respectively, due to cleavage of the prenyl side chain in both compounds.
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... [70] Aegle marmelos also contains limonene, α-phellandrene, β-ocimene, α-pinene, (E)-caryophyllene, β-elemene, and germacrene; [71] sesquiterpene hydrocarbons, germacrene D, and (E)-caryophyllene from Casimiroa edulis; [72] E-ocimenone, Z-ocimenone, gamma-terpinene, and germacrene D from Clausena anisata; [73] 2-tridecanone, betacaryophyllene, 2-pentadecanone, caryophyllene oxide, and germacrene D from Pilocarpus microphyllus. [74] Limonene from Pilocarpus spicatus; [75] β-myrcene, (Z)-β-guaiene, (Z)-β-ocimene, β-caryophyllene, bicyclogermacrene, α-terpinyl acetate, geijerene, and β-copaene-4α-ol from Boenninghausenia albiflora; [76] dictagymnin and feniculin estragole from Dictamnus albus; [77] Agathosma betulina limonene, pulegone, α-pinene, β-pinene, p-cymene, and linalool act as feeding deterrent in termites. ...
... Burning bush Dictagymnin, Feniculin, Estragole Reticulitermes speratus [77] 20. ...
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This review article explains the use of various plant essential oils (EOs) and its formulations in termite control. Plant EOs and its components show multiple deleterious effects such as toxic, antifeedant, repellent, growth, and reproductive inhibitory activity in number of insect pest species. These active components delay egg maturation and development in insects. Plant EOs constituents display contact and systemic action and primarily used as poison baits to control soil termite. This article points out the importance of the use of plant origin termiticides/ biopesticides and botanical methods to control termite menace. These alternate methods could be used to minimize the risk of poisoning of food chain, soil, and aqueous environment. This article also suggests wider use of EO-based multicomponent low-cost anti-termite formulations/methods to replace highly toxic synthetic pesticides.
... The genus Dictamnus L. (Rutaceae) is represented in the flora of Turkey by a single species, D. albus L. (3). The plant is rich in flavonoids (4), quinoline alkaloids (5), psoralens as coumarins (6) and essential oils (7). The main psoralens in D. albus are 5-methoxypsoralen and 8-methoxypsoralen (6), whereas the main components in the essential oil are dictagymnin, feniculin, methylchavicol and trans-anethol (7). ...
... The plant is rich in flavonoids (4), quinoline alkaloids (5), psoralens as coumarins (6) and essential oils (7). The main psoralens in D. albus are 5-methoxypsoralen and 8-methoxypsoralen (6), whereas the main components in the essential oil are dictagymnin, feniculin, methylchavicol and trans-anethol (7). In Indian folk medicine, Dictamnus albus has been used as an emmenagogue and abortive agent (8,9). ...
Purpose of the present study was to investigate pharmacological and toxicological effects of gas plant. Aqueous extracts prepared from its leaves and fruits were tested on the guinea-pig skin by comparing with 2,4-dinitrochlorobenzene. When histopathological examination was made on guinea-pig skin injected with the extracts, there was no change observed in mast cells, but acute exudative inflammation and infiltration of polymorphonuclear leukocytes were noticed in the hypodermis. Their edema forming activities were also tested in the rat paw experiment and their effects were compared to those induced by formalin. In vivo bronchial tone/blood pressure and isolated ileum experiments in guinea-pigs were performed. Aqueous extracts prepared from this plant were found to cause bronchoconstriction and hypotension, which were not dose-dependent. They also elicited concentration-dependent contractions of the isolated guinea-pig ileum, which were not abolished by chlorpheniramine, ketotifen and dexamethasone. D. albus extracts had no significant effect on the mouse pain threshold in "Tail-clip" experiments. Their effects on the central nervous system were examined by using swimming endurance test and observational screening on mice. In this case, a sedative activity was observed. It was concluded that aqueous macerates from leaves and fruits of D. albus causes an acute phase inflammatory response. Akgiritotu (Dictamnus albus L.)'nun Farmakolojik ve Toksikolojik Etkileri Bu çalışmanın amacı Akgiritotu'nun farmakolojik ve toksikolojik etkilerini araştırmaktır. Yaprak ve meyvalarından hazırlanan sulu ekstreler kobay derisi üzerinde 2,4-dinitrobenzen ile karşılaştırmalı olarak test edilmiştir.
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The present review article emphasizes anti-termite efficacy of various plant natural products for control of Indian white termite and its associating species. The Indian white termite, Odontotermes obesus (Rambur) (Isoptera: Odontotermitidae), is highly destructive polyphagous insect pest in Eastern Uttar Pradesh. It damages commercial wood, food crops, orchard plants and house hold articles. Though, several methods have been used to control this termite species in field, but present article explains most recent developments happened in termite control. Present article clarifies seasonal cycle of termite species and suggests use of natural plant products as termiticides to replace synthetic pesticides. As there are reports that residues of synthetic pesticide persist for longer duration in soil system and in aquatic habitat. These enter into the food chain and kill non target organisms. This article found plant essential oils from the family Rutaceae as new alternatives of synthetic pesticides if used in blends or with other natural products. Essential oils are highly volatile at a very low temperature and could be used as fumigants to control household termite population mainly reside inside tunnels, crevices, wood spaces and holes. Plant essential oils and its constituents are safe for the environment and medium. They inhibit metabolism in termites and kill them due to anti-feedant, repellent and toxic action. This article also explains cultural, behavioral, microbial, genetical and biological control of termites to minimize the use of synthetic pesticides so as to save the ecological food chains from poisoning.
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The leaf oils of Clausena anisata Hook. f. collected from Pokuase, Ghana, were found to contain (E)-foeniculin as a major constituent (>78%) in 17 of 19 samples. (E)-anethole was the major constituent of the two other samples (57% and 67%) with (E)-foeniculin as the second most important compound (38% and 29%). The identity of the new natural product (Z)-foeniculin, present in small amounts (0.2-1.4%), was based on a comparison of retention indices and mass spectra with those of a synthesized sample whose spectroscopic data, reported here for the first time, are in agreement with the proposed structure. Two other minor constituents were identified as the rarely encountered natural products dictagymnin (1-20%) and 4-(3-methyl-2-butenyl)oxybenzaldehyde (0-0.2%).
The oils from the leaves and flowers of Dictamnus albus L. grown and harvested in Italy were analyzed by GC/MS. The major components in the oil from leaves were germacrene D (38.1%), and phytol (28.9%), while in the oil from the flowers the major components were limonene (19.1%), γ-terpinene (11.1%) and citronellol (10.8%).
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The purpose of this study was to investigate chemical composition of the essential oil of Dictamnus albus L. The analyses of the oil of Serbian origin were performed using GC-FID and GC-MS systems. Among 56 of registered constituents, 47 were identified. The content of identified monoterpenes was 3.1 percent (citronellol and geraniol as the major constituents), sesquiterpenes 40.3 percent (germacrene D 21.1 percent and bicyclogermacrene 8.1 percent), diterpenes 20.6 percent (phytol 10.2 percent), triterpenes (squalene 0.3 percent). In addition, the results showed presence of non-terpenic hydrocarbons (19.3 percent) and acids and esters (5.3 percent). Generally, besides germacrene D, bicyclogermacrene and phytol as dominant compounds, other main ones were (3E)-cemberene A (7.0 percent), n-pentacosane (7.0 percent) and ethyl hexadecanoate (4.7 percent). On that basis and other literature data, it could be discussed about different chemotypes of Dictamnus albus L.
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Essential oil from the flowers, bracts and leaves of Tilia platyphyllos Scop., T. rubra DC. and T. argentea Desf. ex DC. growing in Turkey were examined by GC/MS. The composition of the essential oils showed differences. The essential oils from the flowers of T. platyphyllos and T. rubra were characterized by a high percentage of hydrocarbons (47.5–66.5%), whereas T. argentea flowers were rich in esters (34.8%). Esters were also in high amount in the bracts of T. argentea (27.0%). The high content of aliphatic acids were found in the all parts of T. platyphyllos (28.3–37.1%), T. argentea (29.4–41.0%) and bracts of T. rubra(30.M). Kaur-l6-ene (29.3% and 41.9%) was the major constituent in the leaf oils of T. rubra and Tplatyphyllos, respectively. It was also the main constituent of the bract oil of the latter (25.8%). Hexadecanoic acid, 2-phenethyl benzoate, β-ionone, geranyl acetone, farnesyl acetone and hexahydrofarnesyl acetone were characterized as the main oxygenated constituents.
The composition of the essential oil of Dictamnus hispanicus Webb ex. Willk. collected in eastern Spain was analyzed by GC and GC/MS. The main constituents identified were methyl chavicol (79%) and limonene (7%). The high oil yield (72.0% fresh plant material) and the proportion of the main compounds support the consideration of D. hispanicus as a separate species of the S. and CS. Europe as D. albus aggregate or as a new chemotype of the polymorphic D. albus.
The detailed study of volatiles of Dictamnus gymnostylis Steven. (Dictamnus albus L., original polymorphic species) considered by many to be the Burning Bush of the Bible, was conducted. In addition to methyl chavicol (~15%), (E)-anethole (~7%) and psoralen (~7%), the presence of over 60% of 1-allyl-4- (3-methyl-2-butenyloxy) benzene (dictagymnin) was confirmed. It was shown that this chemical rather easily decomposes into chavicol and very flammable hydrocarbon 2-methyl-1,3-butadiene = isoprene (b.p. 34°C). The secretion of isoprene, which can be especially intense on hot windless days, leads to formation of the isoprene cloud that may inflame without any harm to the source plant.
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