Eudesmanolides from Artemisia judaica

The aerial parts of Artemisia judaica afforded in addition to known compounds a hydroperoxide corresponding to vulgarin as well as an isomer of the latter. The configurations of these lactones have been established by NOE difference spectroscopy.     

Genetic diversity of Artemisia populations in central and north Saudi Arabia based on morphological variation and RAPD polymorphism

The analysis of morphological variation and RAPD polymorphism distinguished populations of A. herba alba from populations of A. judaica and A. monosperma. Higher morphological diversity is found in A. herba alba compared to the other two species, but molecular data derived from RAPD polymorphism also indicated that A. herba alba is more polymorphic than the other two species. However, RAPD fingerprinting also indicated sharp polymorphism among populations of both A. judaica and A. monosperma. Geographic and local ecological variations related to elevation of the sites of the examined populations may be regarded to have played a role in the genetic diversity of the examined populations of Artemisia species in the study area. The results are important for future plans for sustainable conservation of medicinal plants in Saudi Arabia. However, extensive sampling of the examined Artemisia species populations is required, and more regional data should be obtained from other distribution areas.     

Flavonoid glycosides of Artemisia monosperma and A. herba-alba

Ten flavonoid glycosides were isolated and identified from Artemisia monosperma: vicenin-2, lucenin-2, acacetin 7-glucoside, acacetin 7-rutinoside, the 3-glucosides and 3-rutinosides of quercetin and patuletin, and the 5-glucosides of quercetin and isorhamnetin. From Artemisia herba-alba eight flavonoid glycosides were isolated and identified: isovitexin, vicenin-2, schaftoside, isoschaftoside and the 3-glucosides and 3-rutinosides of quercetin and patuletin.     

An insecticidal diacetylene from artemisia monosperma

The essential oil of Artemisia monosperma obtained by steam distillation of the aerial parts of the plant was shown to have insecticidal activity against house fly, cotton leaf worm and the rice weevil. The chemical structure of the active ingredient from the steam distillate was shown to be 3-methyl, 3-phenyl-1,4-pentadiyne.     

Flavonoids of Artemisia judaica,A. Monosperma and A. herba-alba

Seventeen flavonoid glycosides were isolated and identified from Artemisia judaica: the 7-glucoside, 7-glucuronide, 4′-glucoside, 7-gentiobioside     

Phytochemical and toxicological studies of Artemisia L. (Compositae) essential oil against some insect pests

Abstract

Artemisia herba-alba (Asso) and Artemisia monosperma (Delile) essential oils were tested against three sucking insect pests under laboratory and greenhouse conditions. These pests included Bemisia tabaci (Gennadius), Aphis gossypii (Glover) and Thrips tabaci (Lindman). Laboratory results showed that the LC₅₀ of A. herba-alba and A. monosperma were 0.042, 0.186% for eggs and 0.074, 0.075% for immature stages of B. tabaci. Also, both oils gave a high toxicity on A. gossypii with LC₅₀ 0.023 and 0.085%. Artemisia herba-alba and A. monosperma were more toxic on T. tabaci and A. gossypii than B. tabaci in the laboratory test. In contrast T. tabaci was sensitive for both oils (LC₅₀ 0.011 and 0.038%). These oils were efficient for controlling tested insects on cucumber plants at greenhouses. This treatment caused 85.41, 83.57% reduction in the population of B. tabaci, 90.44, 88.00% for Aphis gossypii and 87.45, 84.45% for T. tabaci. Chemical analysis of A. herba-alba and A. monosperma oils detected the presence of hydrocarbon terpenes, oxygenated terpenes, hydrocarbon sesquiterpenes and oxygenated sesquiterpenes represented about 16.38%, 58.91%, 21.61%, 2.74% and 21.53%, 57.17%, 19.32%, 1.70%, of the oil content, respectively.     

Evaluation of in vitro shoots of <Emphasis Type="Italic">Artemisia judaica</Emphasis> for allelopathic potential

Allelopathic performance of in vitro fresh green shoot, green, and brown shoot extracts including dry shoot powders of Artemisia judaica was evaluated through bioassay-guided studies using lettuce under laboratory conditions. The dry powders caused strong germination and growth inhibition of the lettuce seed tested. The green and brown shoot crude extracts of A. judaica also produced a strong germination and growth inhibition. The magnitude of inhibition in experiments with the brown shoot extracts was higher than that with the green shoot extracts. The lettuce seed incubated together with the fresh green shoots showed that the growth of lettuce was stimulated, while the germination of seed was delayed. The results show that there are different allelochemicals present in the exudates and volatiles of A. judaica. The shoot extracts under assay conditions showed a dose-dependent free radical scavenging effect of DPHH and a dose-dependent reduction of chlorophyll content from lettuce leaves. The antioxidant potential and total chlorophyll content of the lettuce leaf declined in all the shoot extract treatments. These results clearly indicate that the in vitro shoot of A. judaica contains some strong biologically active allelochemicals that are involved in plant growth regulation.     

Composition and infraspecific variability of Artemisia herba-alba from southern Spain

The composition of the essential oils of 16 individual plants of Artemisia herba-alba Asso ssp. valentina (Lam.) Marcl. (at the full bloom stage) growing wild in four different locations from southern Spain were investigated by capillary GC and GC–MS in combination with retention indices. Among the 60 identified constituents (accounting for 80.6–95.0% of the oils), 33 have been reported for the first time in Spanish A. herba-alba oil and 17 of them have not been previously described in A. herba-alba oil. From the analysis of the oil samples, it could be deduced that a noticeable chemical polymorphism typified this taxon. Four groups of essential oils exhibited a single compound with percentages near 30% or higher: davanone, 1,8-cineole, chrysanthenone and cis-chrysanthenol. Two further oil types showed p-cymene and cis-chrysanthenyl acetate as major components in moderate amounts (ca. 20%). All of these types of essential oils have not been previously found in A. herba-alba from Spain and the appearance of such considerable amount of p-cymene is described here for the first time in A. herba-alba.     

Chemical Composition and Insecticidal Activity of Artemisia scoparia Essential Oil against Three Coleopteran Stored-Product Insects

Chemical composition of the essential oil from Artemisia scoparia Waldst et Kit, and its fumigant and repellent activity were investigated against three stored product insects, Callosobruchus maculatus (Fab.), Sitophilus oryzae (L.), and Tribolium castaneum (Herbst). Dry ground leaves were subjected to hydrodistillation using a modified clevenger-type apparatus and the chemical composition of the volatile oil was studied by GC-MS. Nineteen components (99.51% of the total composition) were identified. β-Pinene (19.01%), capillin (17.45%), limonene (15.11%), myrcene (10.95) were found to be the major constituents of the oil. The mortality of 1-7 day old adults of the insect pests increased with concentration from 37 to 926 μL per L air and with exposure time from 3 to 24 h. A concentration of 37 μL per L air and exposure time of 24 h was sufficient to obtain 100% kill of the insects. Callosobruchus maculatus was more susceptible than S. oryzae and T. castaneum. A second more detailed bioassay gave estimates for the LC₅₀ of C. maculatus as 1.46 μL per L air, S. oryzae 1.87 μL per L air and T. castaneum 2.05 μL per L air. Also, the essential oil was significantly more repellent to T. castaneum and S. oryzae than C. maculatus. However, half-life time of the oil for C. maculatus was longer than S. oryzae and T. castaneum. These results show the efficacy of A. scoparia oil for use in organic food protection.     

Composition of essential oil of <Emphasis Type="Italic">Artemisia scoparia</Emphasis> Waldst. et Kit. from Buryatia and Mongolia

Essential oil from the epigeal portion of Artemisia scoparia Waldst. et Kit. collected in different regions of Buryatia and Mongolia has been isolated using steam distillation. The yield of essential oil from the stems and leaves of A. scoparia collected in different regions of Buryatia and in the Selenga aymag of Mongolia ranged from 0.06 to 0.40%, that is, the variation was rather high. The composition of the oil was analyzed using chromatography with mass spectrometric detection on a gas chromatography device Agilent Packard HP 6890 N with a quadrupole mass spectrometric detector HP MSD 5973. The total number of compounds detected exceeded 100. The major components of Artemisia scoparia oil were the following: p-cymene (0.6–15.2%), limonene (0.1–6.3%), α-pinene (0.2–10.1%), β-pinene (0.4–8.9%), trans-β-ocimene (0.3–5.4%), caryophyllene (4.6–13.8%), germacrene D (11.5–40.3%), spathulenol (4.0–11.7%), and caryophyllene oxide (4.3–15.6%). Several chemotypes of essential oil from A. scoparia were identified according to the nature of the major components: 1) oil that contained acetylene hydrocarbons (from plants collected in Gilan, Mazandaran, Kashan, and Tigran provinces of Iran, Tajikistan, and the European part of the CIS); 2) oil that contained monoterpenes and aromatic compounds (from plants collected in the Khorasan province of Iran, India, and South Korea); and 3) oil that contained monoterpenes or aromatic and sesquiterpene compounds (from plants collected in Kazakhstan and Mongolia). The major components of A. scoparia essential oil obtained from Buryatian plants belonged to the classes of mono- and sesquiterpene compounds, and thus the oil can be assigned to the third chemotype characteristic of A. scoparia from geographically close regions.     

A glandular trichome-specific monoterpene alcohol dehydrogenase from Artemisia annua

The major components of the isoprenoid-rich essential oil of Artemisia annua L. accumulate in the subcuticular sac of glandular secretory trichomes. As part of an effort to understand isoprenoid biosynthesis in A. annua, an expressed sequence tag (EST) collection was investigated for evidence of genes encoding trichome-specific enzymes. This analysis established that a gene denoted Adh2, encodes an alcohol dehydrogenase and shows a high expression level in glandular trichomes relative to other tissues. The gene product, ADH2, has up to 61% amino acid identity to members of the short chain alcohol dehydrogenase/reductase (SDR) superfamily, including Forsythia × intermedia secoisolariciresinol dehydrogenase (49.8% identity). Through in vitro biochemical analysis, ADH2 was found to show a strong preference for monoterpenoid secondary alcohols including carveol, borneol and artemisia alcohol. These results indicate a role for ADH2 in monoterpenoid ketone biosynthesis in A. annua glandular trichomes.     

Ecological variations and role of heat shock protein in Artemisia judaica L. in response to temperature regimes of Tabuk,Saudi Arabia

Artemisia judaica L. (Compositae) are shrubby herbs growing wildly in Tabuk region and distributed in the desert regions. This region is characterized by extremely variable environmental conditions where the temperature varies from extreme low to extreme high. These temperature regimes have a profound effect on morphology, growth physiology and biochemistry of the plants. The plant samples were collected from Tabuk–Jordan road (760 m above sea level) in the month of January, April, July and October 2013 to evaluate the effect of temperature dynamics on A. judaica L. in four different seasons. Physiological, biochemical alterations and heat shock proteins (HSPs) were studied during these seasons in order to evaluate the environmental adaptation and stress tolerance in response to temperature variations. Plant growth parameters showed a significant increase in height, fresh and dry matter accumulation, total chlorophyll, nitrogen, phosphorus, potassium, artemisinin and leaf relative water contents investigated in the month of April and October. Growth of plant was suppressed and an active role of carbonic anhydrase (CA), catalase (CAT), peroxidase (POD) and superoxide dismutase (SOD) was observed to cope with the extreme low temperature in January and extreme high temperature in July 2013. However, the plants collected in October and April did not show a statistical difference. Inductions in the expression of HSP90 were recorded in all the plants collected during April and October 2013 with no statistically significant difference. Therefore, based on the results it is recommended that during April and October the environmental conditions are best suitable for growth, development and medicinal use of Artemisia.     

Variation in terpene composition of Artemisia alba in relation to environmental conditions

The essential oil from inflorescences of Artemisia alba Turra (Compositae) was analysed by GLC; 33 different components were detected, 21 of which were identified by GC-MS. The composition of the extract changes with environmental and climatic conditions of the sites of collection (Adriatic area-NE Italy). Artemisia alba produces mainly sesquiterpene hydrocarbons when growing in thermophytic plant communities and mostly oxygenated monoterpenes in mesophytic plant communities. The results of ordination and cluster analysis performed on chemical data allowed the identification of four chemical types of A. alba.     

香叶蒿挥发油化学成分研究

为了分析香叶蒿挥发油的化学成分和进一步开发利用香叶蒿提供科学依据,本文采用水蒸气蒸馏法提取,运用气相色谱-质谱联用法对香叶蒿挥发油化学成分进行了分析,用气相色谱面积归一化法测定了各成分的相对百分含量。经毛细管色谱分离出56个峰,并鉴定出各峰所对应的化合物.其主要化学成分为桉树醇(Euca-lyptol),樟脑(Camphor),孟烯醇-4(Menthen-4-ol),异丁酮-2-基-苯(2-Butanone,3-phenyl),对异丁基苯酚(Phe-nol,4-(2-methylpropyl)等。香叶蒿挥发油中化合物含量丰富,且药用,及香料工业用的化合物含量较高,因此香叶蒿有很好的开发利用价值。     

Chemical composition,aphicidal and antiacetylcholinesterase activities of essential oils against Aphis nerii Boyer de Fonscolombe (Hemiptera: Aphididae)

Aphids are important sucking insects that attack many crops and cause huge economic loss. Essential oils have been proposed to be appropriate alternative to synthetic insecticides due to their low impact on environment and human health. In this work, the chemical compositions of eight essential oils extracted from plants growing in Egypt were determined by gas chromatography/mass spectrometry (GC–MS). The aphicidal activities of the isolated oils were examined against the adults of oleander aphid, Aphis nerii by a leaf-dipping assay. The inhibitory effect of essential oils on acetylcholinesterase (AChE) activity was also tested in vitro. Chemical analyses showed the essential oils consisted mainly of monoterpene hydrocarbons, oxygenated monoterpenes, sesquiterpene hydrocarbons and oxygenated sesquiterpenes except the oil of Artemisia monosperma which contained high content of benzenes. The results of toxicity assay showed that the oils of A. monosperma and Citrus sinensis were the most potent toxicants displaying LC₅₀ value of 0.06 mg/L. The oils of Callistemon viminals, Schinus terebinthifolius and Schinus molle were also highly effective against aphid as their LC₅₀ values were lower than 1 mg/L. In addition, the highest inhibitory effect on AChE was recorded by 0.5 mg/L C. sinensis with inhibition of 49.33%, while 0.1 mg/L Citrus lemon oil recorded the lowest inhibitory effect with inhibition of 0.4%. In general, six of tested essential oils showed high toxicity against A. nerii and they might be applied in the IPM programs for this insect.     

Screening of potential cytotoxic activities of some medicinal plants of Saudi Arabia

Phytochemicals from plant extracts belong to an important source of natural products which have demonstrated excellent cytotoxic activities. However, plants of different origins exhibit diverse chemical composition and bioactivities. Therefore, discovery of plants based new anticancer agents from different parts of the world is always challenging. In this study, methanolic extracts of different parts of 11 plants from Saudi Arabia have been tested in vitro for their anticancer potential on human liver cancer cell line (HepG2). Particularly, for this study, plants from Asteraceae, Resedaceae and Polygonaceae families were chosen on the basis of locally available ethnobotanical data and their medicinal properties. Among 12 tested extract samples, three samples obtained from Artemisia monosperma stem, Ochradenus baccatus aerial parts and Pulicaria glutinosa stem have demonstrated interesting cytotoxic activities with a cell viability of 29.3%, 28.4% and 24.2%, respectively. Whereas, four plant extracts including Calendula arvensis aerial parts, Scorzonera musilii whole plant, A. monosperma leaves show moderate anticancer properties bearing a cell viability ranging from 11.9 to 16.7%. The remaining extracts have shown poor cytotoxic activities. Subsequently, GC-MS analysis of methanolic extracts of four most active plants extracts such as C. comosum, O. baccatus, P. glutinosa and A. monosperma detected the presence of 41 phytomolecules. Among which 3-(4-hydroxyphenyl) propionitrile (1), 8,11-octadecadiynoic acid methyl ester (2), 6,7-dimethoxycoumarin (3) and 1-(2-hydroxyphenyl) ethenone (4) were found to be the lead compounds of C. comosum, O. baccatus P. glutinosa and A. monosperma, respectively.     

Physiological Conjunction of Allelochemicals and Desert Plants

Plants exchange signals with other physical and biological entities in their habitat, a form of communication termed allelopathy. The underlying principles of allelopathy and secondary-metabolite production are still poorly understood, especially in desert plants. The coordination and role of secondary metabolites were examined as a cause of allelopathy in plants thriving under arid and semiarid soil conditions. Desert plant species, Origanum dayi, Artemisia sieberi and Artemisia judaica from two different sources (cultivar cuttings and wild seeds) were studied in their natural habitats. Growth rate, relative water content, osmotic potential, photochemical efficiency, volatile composition and vital factors of allelopathy were analyzed at regular intervals along four seasons with winter showing optimum soil water content and summer showing water deficit conditions. A comprehensive analysis of the volatile composition of the leaves, ambient air and soil in the biological niche of the plants under study was carried out to determine the effects of soil water conditions and sample plants on the surrounding flora. Significant morpho-physiological changes were observed across the seasons and along different soil water content. Metabolic analysis showed that water deficit was the key for driving selective metabolomic shifts. A. judaica showed the least metabolic shifts, while A. sieberi showed the highest shifts. All the species exhibited high allelopathic effects; A. judaica displayed relatively higher growth-inhibition effects, while O. dayi showed comparatively higher germination-inhibition effects in germination assays. The current study may help in understanding plant behavior, mechanisms underlying secondary-metabolite production in water deficit conditions and metabolite-physiological interrelationship with allelopathy in desert plants, and can help cull economic benefits from the produced volatiles.     

艾叶挥发油化学成分研究进展

艾叶挥发油是艾叶发挥药理作用的主要活性成分,由100余种化学成分组成,主要含单萜及其衍生物、倍半萜及其衍生物,也有少量的醛、酮、酚类化合物。本文对近十年艾叶挥发油化学成分研究的相关文献进行了分析与总结,发现产地、提取方法和采收期对艾叶挥发油化学成分数量和含量的测定结果均有较大影响,进而影响对艾叶药材的质量评价和应用。因此建议根据不同的药用目的选择采用不同产地的艾叶药材和相应的挥发油提取方法,为艾叶挥发油化学成分的进一步研究和临床应用提供参考。     

The Accumulation of Volatile Oils in Whole Plants and Cell Cultures of Tarragon (Artemisia dracunculus)

Two important factors thought to be involved in determiningproduct yields in plant cell cultures are the genotype of theexplant material and the level of cell and/or tissue differentiationexhibited. Cell culture of A. dracunculus is reported for thefirst time and the accumulation of volatile oils in differentgenotypes and at various levels of differentiation are examined.The quantity and quality of oils accumulated varied markedlybetween plants of different types and with the level of anatomicaldifferentiation, both in planta and in vitro. The phenylpropene,allylanisole, the major component of commercial tarragon oil,is reported for the first time in disorganized cultures. Key words: Artemisia dracunculus, tarragon, tissue culture, essential oil, phenylpropenes, allylanisole