Seasonal and diel variations in scent composition of ephemeral Murraya paniculata (Linn.) Jack flowers are contributed by separate volatile components

Scent profile of the ephemeral nocturnal floral species Murraya paniculata was characterized to assess diel and seasonal variability. The floral fragrance was found to constitute a characteristic set of 15 major volatile organic compounds (VOCs) dominated by benzenoids, terpenoids and phenylethanoids. Strong diel variability was detected due to dominantly endogenous regulation of 2-phenylethanol and (E)-β-ocimene emission levels, along with temperature-correlated emission rates of 2-phenylethanal, methyl benzoate, methyl anthranilate and germacrene D, resulting in high diurnal contents of the former two VOCs and high nocturnal contents of the latter four VOCs in the fragrance. Significant seasonal variation was contributed by a separate suite of VOCs including linalool, nonanal, decanal, methyl salicylate and methyl palmitate. Higher abundances of these components in certain seasons were found to add subtle variations in the strong diurnal/nocturnal division in the scent profile. Emission rate of linalool is endogenously regulated on a seasonal scale, but that of (E,E)-α-farnesene was maintained at consistent proportions even if correlated to temperature variations. It was concluded that the two sub-sets of major scent compounds, each comprising six VOCs, are adaptive responses such that the strong day/night component of variation in maintained along with necessary physiological adjustments to changing seasons. The varying effects of climatic factors on the 15 major VOCs indicated different regulating mechanisms comprising environmental and endogenous mechanisms in different degrees.     

Fragrance chemistry and pollinator affinities in Nyctaginaceae

We present results of dynamic head-space collections and GC-MS analyses of floral and vegetative fragrances for 20 species in three genera of Nyctaginaceae: Acleisanthes, Mirabilis and Selinocarpus. Most of the species included in this study are either hawkmoth or noctuid moth-pollinated. A wide variety of compounds were observed, including mono- and sesquiterpenoids, aromatics (both benzenoids and phenylpropanoids), aliphatic compounds, lactones, and nitrogen-bearing compounds. Intraspecific variation in fragrance profiles was significantly lower than interspecific variation. Each species had a unique blend of volatiles, and the fragrance of many species contained species-specific compounds. The fragrance profiles presented here are generally consistent with previous studies of fragrance in a variety of moth-pollinated angiosperms.     

Variations in lipophilic and vacuolar flavonoids among European Pulicaria species

Four European Pulicaria species, P. odora, P. paludosa, P. sicula and P. vulgare, were analysed for their surface and vacuolar constituents for comparison with previous data obtained for P. dysenterica. Each species had a distinct flavonoid pattern with notable differences between leaf and inflorescence. 6-Hydroxyflavonols were the major lipophilic components in all of the species and tissues except in the leaves of P. paludosa and P. vulgare, where scutellarein 6-methyl ether was the main constituent. In the leaves of P. sicula a more unusual flavone, 6-hydroxyluteolin 5,6,7,3',4'-pentamethyl ether, was a major component. Pulicaria odora was distinguished by the presence of a series of methylated 6-hydroxykaempferol derivatives including a 3,5,6,7,4'-pentamethyl ether. Quercetagetin hexamethyl ether occurred in both tissues of P. sicula together with the 3,7,3,4'-tetra methyl ether and other quercetagetin derivatives, which were 5-methylated. Quercetagetin 3,7,3'-methyl ether was present in all species except P. odora. Flavonol glucuronides were characteristic vacuolar constituents of all the taxa studied. Two rare glycosides, patuletin and 6-hydroxykaempferol 6-methyl ether 7-glucuronides were identified in the inflorescence of P. odora. Pulicaria vulgaris, a rare plant of southern England, had the vacuolar flavonoid profile most similar to the other more abundant British plant, P. dysenterica.     

Emitted and endogenous floral scent compounds of Prunus mume and hybrids

Prunus mume is the only species of Prunus known to produce a strong floral fragrance. Most interspecific hybrids between P. mume and other species of Prunus lack the fragrance. The analysis of variations in emitted and endogenous compounds among genetically close cultivars is a powerful approach for revealing the mechanisms underlying floral scent emission. Compounds emitted by flowers from five cultivars were collected using the static headspace method, and endogenous compounds in the flowers were extracted with ethyl acetate. Samples were analysed quantitatively and qualitatively using gas chromatography-mass spectrometry. The result showed that benzenoids were the dominant compounds, of which benzyl acetate was the principal component contributing to the floral scent of P. mume. A clustering analysis of the floral volatiles from the different cultivars suggested that the scent traits of hybrids are related to the taxonomic relationship between their parents. The correlations between the amount of the endogenous and emitted compounds revealed that benzyl acetate had a stronger tendency to be volatile than the other compounds and the volatilisation rate of volatile compounds varied greatly among different cultivars. The importance of the biosynthetic pathway and the function of benzaldehyde are discussed.     

The systematic utility of floral and vegetative fragrance in two genera of nyctaginaceae

We examined relationships between fragrance and phylogeny using a number of approaches to coding fragrance data and comparing the hierarchical information in fragrance data with the phylogenetic signal in a DNA sequence data set. We first used distance analyses to determine which coding method(s) best distinguishes species while grouping conspecifics. Results suggest that interspecific differences in fragrance composition were maximized by coding as presence/absence of fragrance compounds and biosynthetic pathways rather than when quantitative information was also included. Useful systematic information came from both compounds and pathways and from fragrance emitted by both floral and vegetative tissues. The coding methods that emerged from the distance analyses as best distinguishing species were then adapted for use in phylogenetic analysis. Although hierarchical signal among fragrance data sets was congruent, this signal was highly incongruent with the phylogenetic signal in the DNA sequence data. Notably, topologies inferred from fragrance data sets were congruent with the DNA topology only in the most distal portions (e.g., sister group pairs or closely related species that had similar fragrance profiles were often recovered by analyses of fragrance). Examination of consistency and retention indices for individual fragrance compounds and pathways as optimized onto one of the most-parsimonious trees inferred from DNA data revealed that although most compounds were homoplastic, some compounds were perfectly congruent with the DNA phylogeny. In particular, compounds and pathways found in a few taxa were less homoplastic than those found in many taxa. Pathways that synthesize few volatiles also seem to have lower homoplasy than those that produce many. Although fragrance data as a whole may not be useful in phylogeny reconstruction, these data can provide additional support for clades reconstructed with other types of characters. Factors other than phylogeny, including pollinator interactions, also likely influence fragrance composition.     

Antioxidative activity of sulfur-containing compounds in Allium species for human LDL oxidation in vitro

Sulfur-containing compounds contributing to health promotion in Allium species are produced via enzymic and thermochemical reactions. Sulfur-containing amino acids and volatile organosulfur compounds were prepared for an antioxidative assay. The inhibitory activity of S-alk(en)yl-L-cysteines and their sulfoxides, volatile alk(en)yl disulfides and trisulfides, and vinyldithiins in Allium species against lipid hydroperoxide (LOOH) formation in human low-density lipoprotein (LDL) was examined. It was elucidated that the alk(en)yl substituents (methyl, propyl, and allyl) and the number of sulfur atoms in the compounds were important for the antioxidative activity. 3,4-Dihydro-3-vinyl-1,2-dithiin, which is produced by a thermochemical reaction of allyl 2-propenethiosulfinate, exhibited the highest antioxidative activity of human LDL among sulfur-containing compounds.     

Exudation of low molecular weight compounds (thiobismethane, methyl isocyanide, and methyl isothiocyanate) as a possible chemical defense mechanism in the marine sponge Ircinia felix

The volatile constituents of the marine sponge Ircinia felix were obtained by dynamic headspace extraction and analyzed by HRGC, HRGC-MS and HRGC-Odor at sniffing port. Fifty-nine volatiles were identified for the first time in the odor of this sponge. Hydrocarbons (32.9%), alcohols (17.8%) and carbonyl compounds (16.0%) predominated in the sponge volatile profile, followed by esters (11.6%), halogen compounds (8.6%), ethers (7.7%), nitrogen and/or sulfur compounds (4.6%) and carboxylic acids (0.8%). Among the identified volatiles, thiobismethane (commonly known as dimethylsulfide), methyl isocyanide and methyl isothiocyanate were found to be responsible for the nauseating and toxic smell emitted by the sponge and for the antimicrobial activity detected in the volatile extract. Exudation experiments in aquarium and in situ conditions revealed that thiobismethane, methyl isocyanide and methyl isothiocyanate are continuously released by the sponge. Upon injury, the concentration of these volatiles increased strongly. Hence, these substances form a chemical protective barrier which may help these sponges avoid fouling, compete for space, prevent infection in the short term, and/or signal generalist predators regarding the existence of other toxic substances in the internal tissues.     

基于 HS-SPME/GC-MS 分析山茶品种‘克瑞墨大牡丹’花器官香气成分简

采用顶空固相微萃取法（HS-SPME）提取了山茶品种‘克瑞墨大牡丹’不同花器官自然挥发的花香挥发油,并用气相色谱—质谱联用仪（GC-MS）分析了花香成分。分别从整花、花瓣、雄蕊中检测到了89、80、21种化合物。花香成分主要由萜类、芳香族化合物、脂肪族化合物等组成,其中以单萜中的芳樟醇相对含量最高,以下依次为顺式氧化芳樟醇、水杨酸甲酯、十四烷等。花瓣和雄蕊中花香成分有较大差别,芳樟醇在花瓣和雄蕊中均占首位,相对含量分别为15.12%和63.97%,雄蕊缺乏烷烃和芳香烃。同一朵花所有花瓣的花香绝对挥发量是所有雄蕊的3倍以上,但质量相同时雄蕊的挥发量却明显高于花瓣,表明花瓣和雄蕊对‘克瑞墨大牡丹’的花香具有同样重要的贡献。     

江西中南部观光木种群及所在群落特征研究

采用样地调查法,对赣中南观光木种群及群落特征进行了研究。结果表明:观光木种群分布格局呈集群分布,径级结构为衰退型。观光木所在群落有维管植物60科94属112种,植物生活型以高位芽植物为主,占总种数的69.64%。植物区系起源古老,成分复杂,具有明显的热带性质。群落除Pielou指数较高外,其它各种多样性指数偏低,各样地间多样性指数有一定的差异;测度观光木所在群落物种多样性时,4种多样性指数未表现出相同的趋势,Simpson指数和Pielou指数在群落不同层次的变化规律为:灌木层>草本层>乔木层,Shannon-wiener指数和物种丰富度指数在群落不同层次的变化规律为:灌木层>乔木层>草本层。观光木本身的生物学特性和人类掠夺式的破坏是导致观光木种群濒危的主要原因。     

Taxonomic implications of volatile secondary metabolites emitted from birch (Betula L.) buds

The volatile secondary metabolites emitted from the buds of 22 different species and two varieties of birch were analyzed using headspace solid-phase microextraction and gas chromatography-mass spectrometry (HS-SPME/GC-MS) methods. The volatile compositions of 21 birch buds are reported for the first time, to our knowledge. Both the mass spectral data and the calculated retention indices were used to identify the compounds. 273 different components were found and the structures of 200 compounds were precisely identified. An additional 46 compounds were classified according to their group. The terpenes were the biggest group of volatile compounds secreted by birch buds, including 13 monoterpenes, 10 C13 norterpenes, 12 norsesquiterpenes and 108 sesquiterpenes. Among the volatiles of the birch buds, 79 aliphatic compounds, 13 aromatics and six furan derivatives were also detected. Based on our chemical analyses, three different groups of birches were separated. Specific features of the first group included the presence of C13 norterpenes and norsesquiterpenes. Meanwhile, buds of the second group of birches were relatively abundant in sesquiterpenes while they did not emit C13 norterpenes or norsesquiterpenes. Buds from the third group of birches were rich in methyl and ethyl salicylates. Some characteristic features were also found for the eight other birch species that were not classified into either of the three groups. The study of the volatile secondary metabolites emitted by birch buds provided information useful for Betula genus chemotaxonomy.     

Mutagenic action of methyl 2-cyanoacrylate vapor

Alkyl 2-cyanoacrylate adhesives were tested for mutagenicity in Salmonella typhimurium strains TA98, TA100, TA1535 and TA1538. Both a normal spot test and a spot test specially designed to test volatile compounds were used. The adhesives were also tested in the plate incorporation assay. These investigations showed that methyl 2-cyanoacrylate adhesives are mutagenic in strain TA100. The spot test for volatile compounds showed that it is the vapors from the methyl 2-cyanoacrylate monomer that are responsible for the mutagenic effect. One can conclude that working with methyl 2-cyanoacrylate adhesives entails exposure to vapors with a mutagenic effect and may therefore pose a carcinogenic hazard. Because the adhesives are used in industry, their mutagenic effect has a special importance in work environment.     

The Fragrance Components of the Jasrninnm sambac (L.) Alton collected by Simultaneous Steam Distillation and Solvent Extraction

The volatile fragrance components of Jasminum sambac (L.) Aiton flower were collected by a modified simultaneous steam distillation and solvent extraction apparatus (SDE). The obtained extract was concentrated to 100 μL by the gas entrainment method in which the extract was distilled under reduced pressure with the influence of a steam of nitrogen. The concentrate was analyzed by GC-MS with PEG-20 M capillary column, and the Kovats indexes were determined at the same time whereby the nalkanes were added into extract. 28 compounds were identified. The major components were: linalool, benzyl acetate, ciscaryophyllene, cis-3-benzyl benzoate, methyl anthranilate and indole. These results show the components of the extract have no qualitative difference from absolute oil. The advantages of the above procedure were discussed in detail.     

Can chemical signals,responsible for mutualistic partner encounter,promote the specific exploitation of nursery pollination mutualisms? – The case of figs and fig wasps

In nursery pollination mutualisms, where pollinators reproduce within the inflorescence they pollinate, floral scents often play a major role in advertizing host location and rewards for the pollinator. However, chemical messages emitted by the plant that are responsible for the encounter of mutualist partners can also be used by parasites of these mutualisms to locate their host. Each species of Ficus (Moraceae) is involved in an obligatory nursery pollination mutualism with usually one pollinating fig wasp (Hymenoptera: Chalcidoidea: Agaonidae). In this interaction, volatile compounds emitted by receptive figs are responsible for the attraction of their specific pollinator. However, a large and diverse community of non-pollinating chalcidoid wasps can also parasitize this mutualism. We investigated whether the chemical message emitted by figs to attract their pollinator can promote the host specificity of non-pollinating fig wasps. We analysed the volatile compounds emitted by receptive figs of three sympatric Ficus species, namely, Ficus hispida L., Ficus racemosa L., and Ficus tinctoria G. Forster, and tested the attraction of the pollinator of F. hispida ( Ceratosolen solmsi marchali Mayr), and of one species of non-pollinating fig wasp [ Philotrypesis pilosa Mayr (Hymenoptera: Chalcidoidea: Pteromalidae)] to scents emitted by receptive figs of these three Ficus species. Analysis of the volatile compounds emitted by receptive figs revealed that the three Ficus species could be clearly distinguished by their chemical composition. Behavioural bioassays performed in a Y-tube olfactometer showed that both pollinator and parasite were attracted only by the specific odour of F. hispida . These results suggest that the use by non-pollinating fig wasps of a specific chemical message produced by figs could limit host shifts by non-pollinating fig wasps.     

Early discrimination of fungal species responsible of ochratoxin A contamination of wine and other grape products using an electronic nose

An electronic nose (e-nose) system using an array of metal oxide sensors (Fox 3000, Alpha MOS) was used to detect and discriminate two ochratoxigenic fungal species, Aspergillus carbonarius (Bain.) Thom and A. niger Van Tieghem, that are responsible for the contamination of wine and other wine grape products, using their volatile production patterns. Two well-known ochratoxigenic strains were used in this study: A. carbonarius A941 and A. niger A75. These strains were grown on three culture media, Czapek Dox modified (CDm) agar, yeast extract sucrose (YES) agar and white grape juice (WGJ) agar, and the volatile organic compounds produced in the headspace by these species were evaluated over periods of 48–120 h. The e-nose system was able to differentiate between the two species within 48 h of growth on YES and WGJ agar using principal component analysis (PCA), which accounted for 99.9% and 97.2% of the data respectively, in principal components 1 and 2, based on the qualitative volatile profiles. This differentiation was confirmed by cluster analysis of data. However, it was not possible to separate these species on CDm agar. Our results show that the two closely related ochratoxigenic species responsible for the contamination of wine and other wine grape products can be discriminated by the use of qualitative volatile fingerprints. This approach could have potential for rapid identification of A. carbonarius and A. niger on wine grape samples, thereby significantly reducing the time of detection of these ochratoxin A producing species.     

慈竹叶精油化学成分研究

首次报道了贵州省慈竹叶精油化学成分的研究。竹叶精油提取率为 0 2 %。用气相色谱 -质谱 (GC/MS)联用仪分离出 87个化合物 ,确认了其中 2 4个 ,主要芳香物质为C5～C8的含氧化合物。     

Fragrances, male display and mating behaviour of Euglossa hemichlora: a flight cage experiment

Abstract. Male euglossine bees (Apidae: Euglossini) collect volatile substances (fragrances) from floral and nonfloral sources and store them in hair‐filled cavities in their hind tibiae. Over time, males accumulate large quantities of complex and species‐specific blends of fragrances. Various hypotheses have been put forward to explain this behaviour, including the idea that fragrance stores reflect the genetic quality of individual males and have evolved through sexual selection and female choice. Clear support of this hypothesis is lacking, largely because male–female interactions are both rare and difficult to observe in nature. Here, we report a flight cage experiment performed in Panama that permitted mating between virgin females (raised from brood cells) and males captured in the forest at fragrance baits. In the cage, eight individually marked males defended small territories around vertical perch sites and showed a characteristic display, which included a previously unreported ‘leg‐crossing’ movement, possibly related to fragrance release. A total of six copulations and three copulatory attempts by Euglossa hemichlora were observed and partly recorded on video. The copulations, all of which were initiated by the female landing on a male perch, were short (4–10 s) and showed no signs of the transfer of chemical substances from male to female. In some cases, the male hovered directly over the female before descending to mount her, possibly facilitating fragrance evaluation by the female. After the experiment, the contents of the males' hind legs were analysed by gas chromatography‐mass spectroscopy, which detected complex mixtures of terpenoids and aromatics (totalling 70 different compounds) dominated by hexahydrofarnesyl acetone, farnesene epoxide, ocimene and p‐dimethoxy benzene. Individual total amounts of fragrances were neither related to display activity or perch occupancy by given males, nor to the frequency of matings achieved. Display activity was the only positive correlate of mating frequency. Generally, individuals had uniformly large amounts of stored fragrances in comparison to a previous study of three other species of Panamanian Euglossa.     

Different regulation of leaf respiration between Spinacia oleracea, a sun species, and Alocasia odora, a shade species

Mature leaves of shade species exhibit lower respiratory rates than those of sun species. To elucidate the mechanism underlying different respiratory rates between sun and shade species, we examined respiratory properties of leaves in Spinacia oleracea L., a sun species, and Alocasia odora (Lodd.) Spach, a shade species, with special reference to changes in the respiratory rate throughout the night. In S. oleracea , rates of both CO₂ efflux and O₂ uptake decreased with time during the night, whereas in A. odora both rates were virtually constant at lower levels. The rates of O₂ uptake in S . oleracea increased upon addition of sucrose, and the rates attained were virtually identical throughout the night. However, the addition of an uncoupler [carbonyl cyanide p -(trifluoromethoxy)-phenylhydrazone; FCCP] did not alter the rates. In contrast, the rates of O₂ uptake in A. odora were enhanced by the addition of FCCP, but not by sucrose. The concentrations of carbohydrates in the tissue decreased throughout the night in both species and the ATP/ADP ratio was always greater in A. odora. These results indicate that, in S. oleracea , the availability of respiratory substrate determines the respiratory rate, while the low respiratory rate in A. odora is ascribed to its low demand for ATP.     

Study of the volatile compounds produced by Debaryomyces hansenii NRRL Y-7426 during the fermentation of detoxified concentrated distilled grape marc hemicellulosic hydrolysates

The volatile compounds produced by Debaryomyces hansenii NRRL Y-7426 during the fermentation of detoxified concentrated distilled grape marc hemicellulosic hydrolysates was analysed by GC?CMS. Thirty-five compounds corresponding to ten groups of volatile compounds: terpenes, higher alcohols, C₆ alcohols, aldehydes, volatile acids, acetates, ethyl esters, volatile phenols, sulphur compounds and hydrocarbons were identified. The supplementation with commercial nutrients increased the concentration of 2-phenylethanol, a commercial flavour and fragrance compound, with a rose-like odour, employed in cosmetics and food industries; and other positive compounds to the aroma such as terpenes and ethyl esters. Non-supplemented media produced the highest content in higher alcohols, volatile acids, sulphur compounds and in the majority of hydrocarbons detected, meanwhile supplementation with vinasses hardly produced volatile compounds. Only four volatile compounds contributed directly to the aroma according to the OAVs values higher than 1. Finally, a PCA analysis allowed accounting for 100?% of the variance.     

Bacterial mutagenicity of some methyl 2-cyanoacrylates and methyl 2-cyano-3-phenylacrylates

The mutagenic potential of three alkyl 2-cyanoacrylate adhesives, three commercial alkyl 2-cyanoacrylate adhesives and three methyl 2-cyano-3-phenylacrylates, was assessed using the Salmonella/microsome mutagenicity assay. Compounds were tested with and without Aroclor 1254-induced rat-liver homogenate (S9 mix). The methyl 2-cyanoacrylate adhesives were mutagenic in the standard plate test with S. typhimurium strain TA100 with and without S9 activation. Methyl 2-cyano-3-(2-bromophenyl)acrylate revealed a direct mutagenic action to S. typhimurium strain TA1535. The compounds most toxic towards the bacterium S. typhimurium, were the methyl 2-cyanoacrylate adhesives (greater than 500 micrograms/plate). All alkyl 2-cyanoacrylate adhesives were tested in a modified spot test for volatile compounds with tester strain TA100. Mutagenic and toxic effects were observed with the three methyl 2-cyanoacrylate adhesives. It can be concluded from the results that the bacterial toxicity and mutagenicity of methyl 2-cyanoacrylate adhesives may be due to the methyl 2-cyanoacrylate monomer.