Chemical Composition and Antimicrobial Activity of the Volatile Fractions from Leaves and Flowers of the Wild Iraqi Kurdish Plant Prangos peucedanifolia Fenzl

The volatile fractions isolated from Prangos peucedanifolia Fenzl leaves and flowers were investigated for their phytochemical composition and biological properties. Flower and leaf hydrodistillation afforded 3.14 and 0.49 g of yellowish oils in 1.25 and 0.41% yields, respectively, from dry vegetable materials. According to the GC‐FID and GC/MS analyses, 36 (99.35% of the total oil composition) and 26 compounds (89.12%) were identified in the two oils, respectively. The major constituents in the flower volatile fraction were β‐pinene (35.58%), α‐pinene (22.13%), and β‐phellandrene (12.54%), while m‐cresol (50.38%) was the main constituent of the leaf volatile fraction. The antimicrobial activity was evaluated against several bacterial and fungal strains, on the basis of the minimum inhibitory concentration (MIC) by the micro‐ and macrodilution methods. The two volatile fractions showed moderate antifungal and antibacterial activities, especially against Trichophyton rubrum (MIC of 2×10³ μg/ml), Streptococcus mutans, Streptococcus pyogenes, and Staphylococcus aureus (MIC≤1.9×10³ μg/ml for all).     

Silene vulgaris subsp. macrocarpa leaves and roots from Morocco: assessment of the efficiency of different extraction techniques and solvents on their antioxidant capacity,brine shrimp toxicity and phenolic characterization

Abstract

This study was undertaken to investigate the effect of various solvents and techniques on the extractability of antioxidant compounds, particularly phenolics, from leaves and roots of Silene vulgaris subsp. macrocarpa grown wild in Morocco. Maceration and hot extraction with methanol or water and Soxhlet ethanol extraction were utilized. Aimed at establishing the potential safety of the extracts, Artemia salina lethality bioassay was performed. All the extracts were found to be non-toxic, except for the leaf Soxhlet ethanol. The antioxidant potential of the extracts was evaluated in vitro by DPPH, reducing power, and ferrous ions chelating activity assays. The leaf extracts displayed noticeable radical scavenging and chelating activities, and maceration with methanol (Mac-MeOH) resulted the most suitable extraction method for an effective recovery of antioxidants; further, the root Mac-MeOH extract demonstrated good chelating properties (IC₅₀ = 335.49?±?0.70?µg/mL). Thus, leaf and root Mac-MeOH extracts were subjected to phytochemical investigations. The total phenolic, flavonoid and condensed tannin content was determined spectrophotometrically. Thirteen polyphenolic compounds were positively identified, by HPLC-PDA-ESI-MS, in the leaf extract for the first time, with p-coumaric acid derivatives being the most abundant ones (81%), whereas only catechin and procyanidin B1 were found in the root extract.     

罗汉果叶片挥发性成分与访花昆虫: 雌雄株差异及其生态影响

为探究罗汉果(Siraitia grosvenorii)自然授粉不良的形成原因,该文以罗汉果品种“大地二号”的种苗为材料,采用定点定时方法调查罗汉果雌雄株访花昆虫,同时利用GC-MS对雌雄株叶片的挥发性成分进行比较分析。结果表明:在雄株上观察到访花昆虫102种,分属于8目29科,其中包括蜜蜂科、眼蝶科、夜蛾科和天蛾科等传粉昆虫类群; 在雌株上观察到访花昆虫69种,分属于7目16科,但未观察到上述传粉昆虫类群。雄株访花昆虫的物种丰富度、多度和Shannon-Wiener多样性均显著高于雌株(P<0.05),Jaccard相似性分析显示,雌株和雄株访花昆虫达到中等不相似水平。在雄株叶片中鉴定出挥发性成分17种,优势成分为萜烯类化合物,占总含量的67.31%; 在雌株叶片中鉴定出挥发性成分12种,优势成分为烷烃类化合物,占总含量的44.27%。雄株具有较多特有成分,包括7种萜烯类和3种酯类成分,占总体成分的45.45%; 雌株的特有成分较少,包括4种烷烃类和1种酯类成分,占总体成分种类的22.72%。Jaccard相似性分析显示,雌株和雄株的挥发性成分总体上达到中等不相似水平,其中萜烯类和酯类的相似度更低,达到极不相似水平。进一步分析表明,在罗汉果雌雄株之间,由于挥发性化合物在优势成分上的重要差异,以及特有成分的大量存在,可能导致了它们访花昆虫类群的显著差异,进而影响了罗汉果的自然传粉过程。     

Phenolic compounds and antioxidants from Eucalyptus camaldulensis as affected by some extraction conditions,a preparative optimization for GC-MS analysis

Abstract

Four organic solvents along with water were applied for the conventional extraction of Eucalyptus camaldulensis (Myrtaceae), phenolic contents and antioxidant activities were investigated through variable protocols and correlation coefficients were considered, the phenolic composition was also characterized by Gas chromatography-mass spectrometry (GC-MS). Using solvents with dissimilar polarities affected the phenolic yields extracted from E. camaldulensis and their related antioxidant activities varied significantly among the four investigated plant organs. The leaf extract of acetone 70% contained the highest amount of phenolic compounds (46.56?mg/g dry weight); while the bud-water boiled extract maintained the maximum value of tannins (45.68?mg/g dry weight). Correlation coefficients indicated that phenolic compounds were mostly accountable for the phosphomolybednum antioxidant potentials (0.520), followed by tannins (0.460). Also, both the reducing power activities and hydrogen peroxide scavenging of E. camaldulensis extracts positively correlated with tannins, but at different significance degrees. However, the GC-MS analysis revealed that most of the detected phenolic constituents were more abundant in the plant seed. So, the existence of some other compounds such as organic acids, along with phenolics, may have increased the antioxidant potentials of leaf and bud. Undeniably, the optimization of extraction conditions could stimulate the antioxidant capabilities of the plant extracts of E. camaldulensis.     

Phenolic composition and antioxidant activities of two Phlomis species: A correlation study

Two traditional Chinese medicines (Phlomis umbrosa Turcz. and Phlomis megalantha Diels), as well as five pure phenolic compounds (protocatechic, chlorogenic, benzoic, rosmarinic acid, and rutin) have been studied for antioxidant activities in acetone and methanol extracts from leaves. An HPLC method was developed to quantify the amounts of 14 phenolic compounds in the leaf extracts. The antioxidant capacities of the studied species are high. Almost all samples were capable of directly scavenging DPPH and superoxide free radicals, inhibiting linoleic acid oxidation, acting as reducing agents, and reducing plasmid DNA damage induced by hydroxyl radicals. Among different extracts, the acetone extract of P. megalantha exhibited the highest antioxidant activity. The major phenolic compounds identified were protocatechic, chlorogenic, caffeic, rosmarinic acid, and (−)-epicatechin. Antioxidant activities of pure compounds and correlation analysis indicated that protocatechic and rosmarinic acids were the major contributors to the observed antioxidant activities of the investigated Phlomis extracts. To cite this article: Y. Zhang, Z.-z. Wang, C. R. Biologies 332 (2009).     

Isolation, Identification and Study of Antimicrobial Property of a Bioactive Compound in an Indian Medicinal Plant Acalypha indica (Indian-Nettle)

Summary Fresh, dried and powdered samples of leaf, stem and root of Acalypha indica were subjected to fractional distillation in a soxhlet apparatus using solvents such as hexane, chloroform, acetone and methanol. The plant extracts and a synthetic antifungal compound, Clotrimazole (authentic standard) were subjected to TLC and HPLC analyses. The R_f (relative front) value of Clotrimazole was 0.371. The plant’s leaf, root and stem extracts also gave distinct spots respectively at R_f value of 0.371 ± 0.0009. In HPLC, the TLC-separated active compound and Clotrimazole resolved at 1.90 ± 0.2 min (retention time). The amounts of active compound present in root, leaf and stem extracts were 538, 415 and 171 μg/g respectively. From the results of our study, we infer that the active compound isolated from Acalypha indica is more potent in controlling Candida albicans, Aspergillus niger and Escherichia coli. The Active compound present in the plant had more than 100% activity when compared to standard Clotrimazole.     

Volatiles released from bean plants in response to agromyzid flies

Liriomyza sativae Blanchard and Liriomyza huidobrensis (Blanchard) (Diptera: Agromyzidae) are two invasive flies in China that have caused economical damage on vegetables and ornamental plants. In this article, we report the profiles of emitted volatiles from healthy, mechanically damaged, and leafminer-damaged bean, Phaseolus vulgaris L., plants. Among 25 emitted volatiles identified, (E)-2-hexen-1-al, (3E)-4,8-dimethyl-1,3,7-nonatriene (DMNT), (Z)-3-hexenyl acetate, (Z)-3-hexen-1-ol, (syn)- and (anti)-2-methylpropanal oxime, (syn)-2-methylbutanal oxime, linalool, and (E,E)-α-farnesene were consistently released from damaged bean plants. Combined amounts of these nine compounds made up more than 70% of the total volatiles emitted from each treatment. No qualitative differences in volatile emission were found between bean plants damaged by the two fly species; however, amounts of several major compounds induced by L. huidobrensis damage were significantly higher than those from plants damaged by L. sativae. The mechanically damaged plants released a higher proportion of green leaf volatiles than plants in the other treatments, whereas leafminer-damaged plants produced more terpenoids and oximes. Furthermore, the volatile profiles emitted from plants, damaged by adult leafminers, by second instar larvae, and even the plants with empty mines left by leafminer larvae (the pupal stage) were significantly different. The identification of volatile oximes released from damaged plants was confirmed and is discussed in a behavioral and biological control context.Electronic Supplementary Material Supplementary material is available for this article at and is accessible for authorized users.     

Chemosensory attraction of fig wasps to substances produced by receptive figs

In the mutualism between figs (Ficus spp., Moraceae) and their species-specific fig wasp pollinators (Hymenoptera: Agaonidae), location of a receptive host tree by the adult insect is a critical step. The adult female wasp lives only a few days, and must usually fly to a different tree than her natal tree to locate receptive figs. Trees in receptive phase often occur at very low densities. Reproductive success of both fig and wasp depends on trasmission of a very strong signal by the plant. Some evidence exists for the role of olfaction in location of receptive hosts by fig wasps, but very little work has been done on the chemical ecology of host location and host specificity. Here the first experimental evidence is presented for long-distance olfactory attraction of wasps by volatile substances produced by receptive figs, and for short-distance or contact chemostimulation by host volatiles that elicit entry of the wasp into the fig. In studies usingFicus carica L., pentane extracts of receptive-phase figs attract the pollinatorBlastophaga psenes L. from distances of at least 5 m in the field. Short-distance chemostimulation was demonstrated in laboratory bioassays. Pentane extracts of receptive figs, when painted onto the ostiole of non-receptive figs, elicit entry of pollinator wasps. Figs emit volatile compounds attractive to pollinating wasps only during the period of receptivity; pentane extracts of non-receptive figs are not attractive. A simple reliable procedure is described to compare the attractivity of different types of extracts (total, internal, and external extracts) and of different fractions, in the first step towards identifying attractant substances.     

狭叶红景天幼苗对水分及遮阴的生长及生理生化响应

研究植物对水分和遮阴胁迫的响应及其生理机制对制定合理的栽培管理措施十分必要。以红景天属植物为研究对象,设置土壤含水量分别为田间持水量的80%(过湿水分)、70%(正常水分)、60%(轻度干旱)、40%(中度干旱)、20%(重度干旱)5个水分梯度;设置2个遮阴处理,以全光照(遮阴率为0)为对照、黑色遮阴网遮阴(遮阴率为85%),研究狭叶红景天生长及生理生化指标的变化特征。结果表明:在不同水分处理下,与对照相比,叶绿素含量、茎干重和茎重比(SMR)显著增加(P0.05),株高、总生物量、叶面积、叶干重、叶重比(LMR)、比叶面积(SLA)、叶面积比(LAR)和叶面积根干重比(LARMR)增加,根冠比和根重比(RMR)减少;随着干旱程度加剧,丙二醛(MDA)、脯氨酸(Pro)和可溶性糖(Ss)含量增加,超氧化物歧化酶(SOD)活性总体呈先增加后减小的趋势。在遮阴处理下,株高、SMR、SLA、LAR和LARMR显著增加(P0.05),叶绿素SPAD值和叶面积增加,总生物量、根干重、根冠比和LMR显著减少(P0.05),茎干重和叶干重减少,MDA含量显著增加,Pro含量略有下降,Ss含量减少。在水分胁迫下,狭叶红景天中度干旱时通过增加酶活性抵御伤害,重度干旱超过其阈值,SOD活性下降,植物体受到伤害,Ss可能是主要的渗透调节物质。在遮阴处理下,狭叶红景天通过增加SLA避免遮阴伤害。狭叶红景天在受到环境胁迫时会通过形态改变、调节MDA含量、抗氧化酶活性和渗透调节物质来保证自身正常的生长发育。     

Hydrolysis products of glucosinolates in Brassica napus tissues as inhibitors of seed germination

Enzymatic hydrolysis of glucosinolates, a class of compounds found in Brassica species, results in a number of products with potential to inhibit seed germination. To investigate the impact of both volatile and water-soluble allelochemicals, germination bioassays using Lactuca sativa seeds were conducted with root and combined leaf and stem tissues of Brassica napus. Tissues in which glucosinolates were hydrolyzed to remove volatile glucosinolate degradation products were compared with intact tissues and water controls. Only tissues containing glucosinolates produced volatiles that inhibited germination. Volatiles were trapped and identified using GC-MS. Volatiles produced in greater quanitity from intact tissues than from tissues without glucosinolates were almost exclusively glucosinolate hydrolysis products. Water-soluble components also inhibited germination. Chemical analysis of extracts confirmed the presence of glucosinolate hydrolysis products, but indicated the involvement of additional allelochemicals, especially in leaf and stem tissues. Results support the proposal that glucosinolate-containing plant tissues may contribute to reductions in synthetic pesticide use if weed seeds are targeted.Abbreviations ITC isothiocyanates - CN organic cyanides - OZT oxazolidinethione - iRoot intact root tissue - iL&S intact leaf and stem tissue - hRoot hydrolyzed root tissue - hL&S hydrolyzed leaf and stem tissue     

Antioxidant activities of the volatile oils and methanol extracts from olive stems

This study was designed to examine the chemical composition and antioxidant activities of the volatile oils and methanol extracts of Olea europaea L. (cvs) chemlali and neb jmel stems. GC and GC–MS analyses of the volatile oils resulted in the identification of 38 and 35 compounds, representing 91.1 and 87.4 % of the volatile oils. Phenylethyl alcohol was found in the volatile oil of each cultivar, which was also the major volatile component of cv. chemlali and cv. neb jmel stems. Besides benzyl alcohol, methyl salicylate and 3-ethenylpyridine were the main volatile compounds of cv. chemlali, while nonanal, 3-ethenylpyridine and benzyl alcohol of cv. neb jmel stems were also the main constituents. Significant differences were also found in total tannin contents among two cultivars, representing 8.10 mg CEQ/g DW in cv. chemlali and 20.47 mg CEQ/g DW in cv. neb jmel. The highest contents of total phenols and o-diphenols were observed in stems extracts of cv. neb jmel (78.26, and 9.56 mg/100 g, respectively). The HPLC profiles for methanol extracts from stems of cv. chemlali and cv. neb jmel showed that oleuropein, vanillic acid and gallic acid were the predominant free phenolic compounds. Antioxidant activities of the volatile oils and the methanolic extract from stems parts were evaluated by DPPH and ABTS⁺ radical-scavenging activity assays. In all tests, methanolic extracts obtained from stems parts showed better antioxidant activity than volatile oils. Principal components analysis of the phenolics content and antioxidant activities showed discrimination between methanol extracts of the two cultivars.     

Phytochemical evaluation and in vitro antifungal activities of Melaleuca styphelioides leaves: comparison between volatile and non-volatile extracts

Abstract

Melaleuca styphelioides is considered as medicinal plant. This study was carried out to evaluate for the first time the phytochemical composition and to compare the antifungal activities of essential oil (EOs), methanol and aqueous extracts of M. styphelioides Sm. leaves against three fungi (Aspergillus niger, Rhizopus nigricans and Penicillium digitatum). A total of 10 components of the EO were identified, with the principal compound being methyl eugenol (87.2%). Results of the phytochemical analysis of leaves extract exhibited the presence of different phytoconstituents (phenolic compounds, flavonoids, tannins and anthocyanins). Volatile and non-volatile extracts were found to express dose-dependent inhibition against all tested fungi. Indeed, the EO oil showed significant inhibition of fungal growth and the IC₅₀ was 2.08?µL/mL for A. niger indicating that M. styphelioides leaf EO was particularly effective against this pathogen. The most susceptible species for the aqueous extract was P. digitatum (IC₅₀= 9.54?mg/mL) whereas R. nigricans was found to be more susceptible to the methanolic extract (IC₅₀= 8.31?mg/mL). Thus, the EO and aqueous as well as methanol extracts of M. styphelioides leaves possess antifungal activity and hence, it can be suggested for use in the food or pharmaceutical industries as an alternative to chemical preservatives.     

Biogeneration of volatile organic compounds produced by <Emphasis Type="Italic">Phormidium autumnale</Emphasis> in heterotrophic bioreactor

The objective of this study was to investigate the volatile organic compounds (VOCs) produced from heterotrophic cultivation of the cyanobacterium Phormidium autumnale with different sources of monosaccharides. The volatiles were isolated by headspace solid-phase micro-extraction in different residence times, separated by gas chromatography, and identified by mass spectrometry (SPME-GC/MS). The profile of volatiles contained a total of 44 volatile compounds when P. autumnale was grown heterotrophically on glucose and 35 when grown on fructose. A combined total of 68 compounds was identified and 11 volatiles were common to both extracts. The compound 3-methyl-butanol was identified among the major volatile compounds formed, reaching a concentration of 141.5 μg mg^?1 dry weight for the glucose-grown cultures and 69.5 μg mg^?1 for the fructose-grown cultures after 144 h. Many of the compounds detected during heterotrophic cultivation originated from terpenoids (β-ionone, β-cyclocitral, and 5,6-epoxy-β-ionone), fatty acids (hexanol, hexanal), or the 2-keto acid pathway (3-methyl-butanol, propanol, butanol).     

Emission of volatile organic compounds by apple trees under spider mite attack and attraction of predatory mites

Emission rates of volatile organic compounds (VOCs) from Pirus malus L. subsp. mitis (Wallr.) var. Golden Delicious and var. Starking attacked by the phytophagous mite Panonychus ulmi Koch, and their attractiveness to the predatory mites Amblyseius andersoni Chant and Amblyseius californicus McGregor, were studied during three years. A large variability was found in the emission of individual VOCs depending on the infestation, the apple tree variety and the date. There were larger total VOC emission rates and larger total VOC leaf concentrations in apple trees attacked by phytophagous mites, especially in the var. Starking. In infested trees of this variety, there were also more predatory mites. An olfactometer assay showed that predatory mites preferentially chose branches infested by Panonychus ulmi (85% went to infested branches vs 15% to uninfested control branches) indicating that volatiles may be used as cues to find their prey.     

Metabolism of phenolic compounds in <Emphasis Type="Italic">Vitis riparia</Emphasis> seeds during stratification and during germination under optimal and low temperature stress conditions

We studied the alterations in phenolic compounds in grape seeds during their stratification and germination under optimal conditions (+25 °C) and at low temperature (+10 °C). Biological materials in the study were seeds of Vitis riparia. Phenolic compounds were extracted from defatted seeds using 80 % methanol or 80 % acetone. The content of total phenolics was determined with the Folin-Ciocalteau reagent, while the content of tannins was determined by vanillin assay and the protein (BSA) precipitation method. The RP-HPLC method was used to determine phenolic compounds (phenolic acids, catechins) in the extracts. High amounts of tannins, catechins, gallic acid and lesser amounts of p-coumaric acid were found in the seeds. The content of total phenolics in acetone extracts was higher than that obtained using methanol. The amounts of phenolic acids and tannins found in V. riparia seeds after stratification were much lower. It may confirm a possible role of these compounds in dormancy of V. riparia seeds. After 72 h of low temperature treatment, inhibition of grape root growth and biochemical changes in seeds were detected. The chilling stimulated increased accumulation of some phenolic compounds (free gallic acid and catechins) in the seeds. These substances can protect plants against some abiotic stressors.     

Discovery and characterization of chemical signals for citrus root weevil, Diaprepes abbreviatus

The tropical root weevil Diaprepes abbreviatus (L. 1758) (Coleoptera: Curculionidae) is a polyphagous insect from the Caribbean Islands and an invasive insect in the southern part of the United States where it is pest of citrus crops and ornamental trees. Adults feed upon foliage where aggregation, mating and oviposition take place. Here, the headspace volatiles from Citrus macrophylla Wester (Rutaceae), D. abbreviatus adults feeding on this plant, adults alone and adult feces, were collected by aeration and solid-phase microextraction (SPME) for analysis by gas chromatography-linked mass spectrometry (GC-MS). Electrophysiological responses of weevil antennal receptors to volatile headspace extracts and synthetic analogues were recorded by gas chromatography-linked electroantennographic detection (GC-EAD) and electroantennograms (EAGs). Antennal responses were recorded to the monoterpenes (R)-(−)-linalool, citronellal, nerol, citral, and geraniol; all present in the headspace of C. macrophylla. Antennal responses were also recorded to carvacrol, present in the headspace of adults and adult feces. The green leaf volatiles cis-3-hexen-1-ol and trans-2-hexen-1-ol, produced by other host plants, elicited reliable responses on the D. abbreviatus antenna. When comparing EAGs between (±)-linalool and (R)-(−)-linalool, no significant difference was found; responses to (R)-(+)-citronellal were larger than for (S)-(−)-citronellal. Among the individual compounds and blends tested using an open T-track dual choice olfactometer, only the blend of (±)-linalool, cis-3-hexen-1-ol and carvacrol (source dose 25:25:2.5 μg) elicited significant attraction of females, the same blend was repellent for males. The biologically active compounds found here likely play a role in host finding by D. abbreviatus and other interactions of the insect with its hostplant. Handling editor: Sam Cook     

Leaf yield loss assessment due to Macrophomina root rot disease in mulberry gardens of south India

Abstract

Leaf yield loss in mulberry due to Macrophomina root rot disease was assessed in three different states of south India at field level. The highest leaf yield loss recorded was in V-1 variety (34.74%), whereas the lowest leaf yield loss was in K-2 variety (28.54%). However, the leaf yields losses in other varieties viz., MR-2 (32.90%), S-36 (32.06%), RFS-175 (31.75%) and S-13 (29.0%) recorded were medium. The average leaf yield loss was 31.49% due to root rot disease caused by M. phaseolina in mulberry.     

Differential Accumulation of Volatile Organic Compounds by Leaves and Roots of Two Guianese Philodendron Species,P. fragrantissimum Kunth and P. melinonii Brongn.

Leaf and root essential oils of two closely related but ecologically distant Philodendron species were extracted in natural conditions in French Guiana and analysed by GC/MS to i) describe the blends of volatile organic compounds (VOCs) produced by those species and ii) analyse species and environment‐based variations in extracts composition. A total of 135 VOCs were detected with a majority of aliphatic sesquiterpenes. P. fragrantissimum produced mainly β‐bisabolene (on average 29.12% of the extract) as well as α‐ and β‐selinene (14.52% and 17.50%, respectively) while in P. melinonii, four aliphatic sesquiterpenes could alternatively be the main component: (E)‐β‐farnesene (up to 91.42% of the extract), germacrene‐D (73.74%), β‐caryophyllene (51.63%) and trans‐α‐bergamotene (41.26%). A significant effect of species and organs on extracts composition was observed while the environment (sun exposure) only affected the relative proportions of monoterpenes and sesquiterpenes in roots of P. melinonii. These results are discussed in the light of the potential role of leaf and root terpenes in Philodendron species.     

Effect of irradiance during growth of Glycine max on photosynthetic capacity and percent activation of ribulose 1,5-bisphosphate carboxylase

The initial (in vivo) and total (activity present after preincubation with CO₂ and Mg²⁺) activities of ribulose bisphosphate carboxylase were both assayed in extracts of leaves of soybean (Glycine max) plants which had been grown under 4 different irradiance levels. The total carboxylase activity per unit leaf area decreased with decreased irradiance during growth but was not different on a dry weight basis. The initial activity as a percentage of the total activity was unchanged (approximately 95%) except in leaves of plants grown at the lowest irradiance (74%). When the plants grown at the lowest irradiance were exposed to high irradiance, the initial activity was increased to 93% of the total. Light saturated rates of photosynthesis per unit leaf area were lower and saturated at lower irradiance for plants grown at lower irradiances. Initial carboxylase activity was correlated closely (r²=0.84) with leaf photosynthesis rate on a dry weight basis.