Changes in the Composition of the Essential Oil of Marjoram during Storage

The composition of volatile components of the essential oil of marjoram plants (Majorana hortensis M.) and its stability during storage were studied by capillary gas chromatography and gas chromatography/mass spectrometry. Storage in the dark for 1 year was associated with insignificant changes in the composition of the essential oil, and its organoleptic characteristics remained largely unaffected. Storage in the light produced considerable changes in the composition of the oil, due to chemical transformations of terpenoids.     

Selective herbivory by Christmas beetles in response to intraspecific variation in Eucalyptus terpenoids

Between-tree variation in the terpenoid composition in the foliage of six species of Eucalyptus was investigated in relation to its effects on herbivory by Christmas beetles (Anoplognathus spp.). All six eucalypt species showed considerable intraspecific variation in terpenoid composition; the cineole content ranged from 13% to 78% of the total oil in different E. melliodora trees, from 0% to 67% in E. conica, 3% to 79% in E. sideroxylon, 1% to 76% in E. camaldulensis, 3% to 60% in E. rubida and 20% to 79% in E. blakelyi. Levels of defoliation by Christmas beetles of nine E. melliodora and eight E. conica trees were quantified from frass traps placed under each tree, and were used to confirm the reliability of visual ratings of defoliation. Defoliation was assessed visually for all six species and was found to be unrelated to the total amount of terpenoids in the foliage of each tree, but strongly associated with the percentage of cineole in the terpenoid mixture. Levels of most terpenoid components were significantly inter-correlated, so it was not possible to determine which components directly affected defoliation. The dominant Christmas beetle at all sites was A. montanus.     

Foliar terpenoids in Tsuga species and the fecundity of scale insects

Summary The relationship between the reproductive success of two Japanese scale insects, Fiorinia externa Ferris and Nuculaspis tsugae (Marlatt) (Homoptera: Diaspididae) and the concentrations of 15 terpenoids in needles of Tsuga sieboldii, the Japanese host, and T. canadensis, the North American host, was investigated during 1981 and 1982 in a field plot of 8-year-old trees in New Haven, CT, USA. Both scales produced significantly more eggs per female on T. sieboldii than on T. canadensis. Stepwise multiple regression analyses indicated that the variation in fecundity within both scales was strongly associated with variation in the terpenoid profile between tree species.General patterns of phytochemical variation between the two Tsuga species based on differences in the concentration of terpenoids having similar chemical structures were revealed by the multivariate statistical technique, principal components analysis. The volatile leaf oil profile of T. sieboldii was relatively richer in terpene alcohols, while that of T. canadensis was relatively richer in terpene hydrocarbons and terpene acetates. The individual terpenoids were then assigned to one of five groups based on chemical structure and regression analyses were repeated; fecundity of both scales increased with increasing concentration of terpenoid alcohols. Fecundity of F. externa was negatively associated with the relative concentration of acyclic terpenes but the opposite was true for N. tsugae. Analysis of foliar terpenoids may provide a basis for predicting the relative susceptibility of Tsuga species to attack by F. externa and N. tsugae.     

A comparison of the volatile oils of mature versus young leaves of Juniperus scopulorum: Chemosystematic significance

The volatile oils of leaves of clonal, greenhouse grown trees of J. scopulorum cv. platinum were examined from young (juvenile or whip leaves) and mature (adult or scale leaves) foliage. Of 36 compounds subjected to analysis of variance, 19 showed significant differences between young and old leaves. In general, the hydrocarbon terpenoids were higher in concentration in new leaves while the oxygenated compounds were higher in the older leaves. This same pattern has been reported in several other gymnosperms. Numerical taxonomy using data on the volatile oils from young and mature leaves yielded the same relative similarities among the five trees examined. Surprisingly, the plants were more similar in the volatile oil from the young leaves than from the mature leaves. The mixing of different ages of leaves in samples for chemosystematic studies is, however, to be discouraged     

Changes in the composition of the essential oil in stored marjoram

The composition of volatile components of the essential oil of marjoram plants (Majorana hortensis M.) and its stability during storage were studied by capillary gas chromatography and gas chromatography/mass spectrometry. Storage in the dark for 1 year was associated with insignificant changes in the composition of the essential oil, and its organoleptic characteristics remained largely unaffected. Storage in the light produced considerable changes in the composition of the oil, due to chemical transformation of terpenoids.     

Volatile compounds from the symbiotic system Azolla filiculoides‐Anabaena azollae bacteria

Abstract

Azolla filiculoides is an aquatic pteridophyte that may be used as animal food, biofertilizer and phytoremediation. Its volatile composition was never studied although several phytochemical analyses were performed. The volatile composition of A. filiculoides grown outdoors in a pond at the Botanical Garden of Lisbon University (BGLU) or in culture conditions as well as the effect of different harvesting times and the storage type were evaluated. The volatiles isolated by hydrodistillation and distillation‐extraction were analysed by gas chromatography and gas chromatography‐mass spectrometry. The oil of all the A. filiculoides samples studied affords a yellowish colour and an unpleasant odour in a yield of 0.01% (v/fw). Alcohols, aldehydes, alkanes and ketones dominated the culture samples, while aldehydes, alcohols, terpenoids and alkanes represented the main volatiles of the BGLU samples. Some quantitative differences were detected in seasonal and type of storage (fresh, dry or frozen at ?20°C) studies of A. filiculoides from the BGLU. The BGLU and culture volatiles showed qualitative differences: 2‐ethyl‐1‐hexanol was only identified in the fern culture, whereas acetophenone, pentylfuran, acetylpyridine and 2‐octanone were only detected in BGLU samples. The dendrogram showed two distinct clusters (culture and BGLU samples). The possible biological origin and bioactivity of some of the volatile compounds is discussed.

Abbreviations: FID, flame ionization detector; i.d., internal diameter; v/fw, volume by fresh weight; GC, gas chromatography; GC‐MS, gas chromatography‐mass spectrometry; u, unified atomic mass unit     

Morphological, chemical and genetic differentiation of two subspecies of Cistus creticus L. (C. creticus subsp. eriocephalus and C. creticus subsp. corsicus)

Cistus creticus L., an aromatic species from the Mediterranean area, contains various diterpenes bearing the labdane skeleton. The production of essential oil from this species has potential economic value, but so far, it has not been optimized. In order to contribute to a better knowledge of this species and to its differentiation, the morphological characters, volatile chemical composition and genetic data of two subspecies (C. creticus subsp. eriocephalus and C. creticus subsp. corsicus) were investigated. The leaf trichomes were studied using scanning electron microscopy. The chemical composition of Corsican essential oil (C. creticus subsp. corsicus) has been reported using GC, GC/MS and ¹³C NMR; the main constituents were oxygenated labdane diterpenes (33.9%) such as 13-epi-manoyl oxide (18.5%). Using plant material (54 samples) collected from 18 geographically distinct areas of the islands of Corsica and Sardinia, the basis of variation in the headspace solid-phase microextraction volatile fraction and an inter-simple sequence repeat genetic analysis were also examined. It was shown that the two subspecies of C. creticus differed in morphology, essential oil production, volatile fraction composition and genetic data.     

Traumatic oil glands induced by pruning in the wound-associated phloem of Eucalyptus globulus: chemistry and histology

The natural occurrence of oil glands in various organs such as bark and leaves is well established as a characteristic of Eucalyptus, but this is the first reported case of traumatic oil glands induced in response to wounding. The new phloem enveloping the wound, which had developed within the 2 years following branch pruning in 5-year-old Eucalyptus globulus Labill., was morphologically distinct from healthy stem phloem. Histological examinations revealed this wound-associated phloem to be largely composed of secretory cavities similar in appearance to oil glands. Subsequent analysis of the wound-associated phloem extracts by GC-MS confirmed the presence of volatile terpenes and phenols. The total extracted oil content determined for wound-associated phloem extracts was significantly higher (>4 times) than for healthy stem phloem extracts. A comparison of the relative abundances of ten individual terpenoids from wound-associated phloem and healthy phloem revealed a number of significant differences in terpene composition. Implications of the role of terpenes as inducible secondary metabolites in tree wound responses are discussed.     

Effects of dietary lipid sources on flavour volatile compounds of brown trout (Salmo trutta L.) fillet

The high cost and unpredictable availability of fish meal and fish oil (FO) forced feed mill companies to look for alternative ingredients for aquafeeds. In this study, the effects of alternative dietary lipid sources [FO as control, canola oil (CO), oleine oil (OO), poultry fat (PF) and pork lard (PL)] in trout feed on flavour volatile compounds occurring in brown trout (Salmo trutta L.) fillet were evaluated after 70 days of feeding (rearing temperature 14.6°C). Total amounts of volatile compounds identified were higher for fillets of fish fed diets containing only FO as lipid sources. Total amount of alcohols and aldehydes of the fillets were linearly directly related to the percentage content of polyunsaturated fatty acids (PUFA) n‐3 of brown trout flesh. The use of alternative dietary lipid sources, modifying the fillet fatty acids composition, affect the total amount of volatile compounds and, changing the relative amount of each volatile compound, affect the flavour of the fish flesh.     

北京地区侧柏和垂柳释放有益挥发性有机物组分日动态变化特征

以侧柏(Platycladus orientalis)和垂柳(Salix babylonica)为研究对象,采用动态顶空套袋采集法和自动热脱附-气相色谱/质谱联用技术来分析这些植物释放的挥发性有机物(VOCs)的组成和释放模式。选择不同的时间和天气条件下的样本进行采集,并记录相关信息。通过对原始数据的分析,确定有益挥发性有机物(BVOCs)的成分和相对百分含量。研究结果显示,侧柏和垂柳在不同季节释放的BVOCs成分主要包括醇类、醛类、烯烃类等其他类化合物,这些有益BVOCs在植物的生理和生态功能中扮演着重要的角色,对于深入了解植物与环境之间的相互作用具有重要意义。侧柏和垂柳释放BVOCs成分在不同季节会有所变化。其次,研究分析了侧柏和垂柳在不同季节中有益BVOCs成分的含量和变动趋势。侧柏在不同季节的释放模式呈现出明显的差异。春季的释放模式呈现出“单峰单谷”曲线,夏季的释放模式呈现出“单峰”曲线,而秋季的释放模式呈现出“双峰单谷”曲线。这表明侧柏在不同季节中的挥发物释放存在明显的季节性变化。相比之下,垂柳的释放模式在不同季节中相对稳定,呈现出一致的“单峰型”曲线。这说明垂柳的挥发物释放...     

A comparative study of ×Cupressocyparis leylandii clones (Cupressaceae) by gas chromatographic analysis of their leaf oils*

The essential oils isolated from foliage of various clones of x Cupressocyparis leylandzi were analyzed by gas chromatography to determine whether the oils could be used as aids in clonal identification. Several botanical gardens supplied foliage which was submitted to hydrodistillation. The oils were isolated under standardized conditions and then analyzed. Comparison of the oil components (mostly monoterpene hydrocarbons) revealed that it is possible to identify, on the basis of the composition of the monoterpene hydrocarbon mixture, clones 1–6 as a group and clones 10 and 11 individually. The composition of the oils from foliage of the widely propagated clones 1,2, 10 and 11 is given in more detail.     

Monoterpenoid accumulation in Melaleuca alternifolia seedlings

Individual leaves of the commercial terpinen-4-ol type of Melaleuca alternifolia were examined both quantitatively and qualitatively for volatile constituents from the emergence of the first true leaves, through to 6-week-old tenth leaf set material. A GC internal standard addition method was used to measure changes in oil composition and the accumulation of volatile constituents expressed on a dry weight, unit leaf area and whole leaf basis. In the early stages of seedling growth, leaves contained higher concentrations of terpinolene, alpha-pinene and beta-pinene and lower concentrations of terpinen-4-ol, sabinene and cis-sabinene hydrate than mature leaf. Concentrations of the former constituents fell and the latter rose by the time leaf set 10 was 6 weeks old. Key constituent, 1,8-cineole remained in similar concentration throughout ontogeny. The variation in concentration of other key constituents during early stages of seedling development suggests that caution is required in extrapolating seedling leaf data to mature tree oil quality.     

Quantifying intra-plant variation of volatile terpenoids in carrot

Comparisons were made of Daucus carota root volatile terpenoids obtained by headspace sampling, direct solvent extraction, and simultaneous distillation-extraction methods. Differences in the relative quantities of individual compounds were observed, but the total volatile terpenoid amount extracted was approximately the same for the direct extraction and distillation methods. The headspace method yielded less of the low and high boiling terpenoids. Using the direct extraction method, variation in terpenoid content of different plant parts was observed. Foliage generally had higher volatile terpenoid concentrations than root phloem, which in turn had more than root xylem.     

仙人掌超微粉挥发性成分研究

目的：研究仙人掌中的挥发性成分。方法：利用水蒸气蒸馏法提取经超微粉碎后的仙人掌[Opuntia dillenii（Ker-Gaw.）Haw]挥发油,用GC-MS进行测定,结合计算机检索技术对分离的化合物进行结构鉴定,应用色谱峰面积归一化法计算各成分的相对百分含量。结果：共分离鉴定出32个化学成分,占总成分的98.097%,其中相对百分含量大于2%的分别确定为异丁基邻苯二甲酸酯（Isobutyl phthalate）27.492%,棕榈酸（Palmitic acid）16.716%,丁基邻苯二甲酸酯（Butyl phthalate）11.257%,薄荷脑（Menthol）6.722%,亚油酸（Linoleic acid）5.995%,壬醛（Nonanal）4.594%,乙醛（Hexanal）3.614%,十二酸（Dodecanic acid）3.244%。结论：通过对仙人掌超微粉挥发性成分的分析鉴定及相对含量测定,为综合利用仙人掌植物资源等提供科学依据。     

Association of Pollinators of Different Species of Oil Palm with the Metabolic Profiling of Volatile Organic Compounds

The development of studies on emissions of volatile organic compounds (VOCs) by inflorescence of oil palms deserves a special attention regarding the importance to reproduction success and for increase of production. This study aimed to evaluate metabolic profiling of VOCs expelled by male and female inflorescences of different oil palm species (African oil palm, Amazonian Caiaué and the interspecific hybrid BRS‐Manicoré), associating the composition variability with main pollinators to improve the comprehension of the plant?insect relationship. The phenylpropanoids, terpenoids and the aliphatic hydrocarbons were predominant classes detected in inflorescences of oil palms and the major compound was estragole. This result may be correlated with attraction of Elaidobius pollinators, since these insects were not attracted by Caiaué, which emitted estragole only in trace amounts. However, Caiaué and the hybrid species were visited by other native species whose frequencies were low and their success as pollinators could not be expected.     

Seasonal respiration of foliage, fine roots, and woody tissues in relation to growth, tissue N, and photosynthesis

Autotrophic respiration may regulate how ecosystem productivity responds to changes in temperature, atmospheric [CO₂] and N deposition. Estimates of autotrophic respiration are difficult for forest ecosystems, because of the large amount of biomass, different metabolic rates among tissues, and seasonal variation in respiration rates. We examined spatial and seasonal patterns in autotrophic respiration in a Pinus strobus ecosystem, and hypothesized that seasonal patterns in respiration rates at a common temperature would vary with [N] for fully expanded foliage and fine roots, with photosynthesis for foliage, and with growth for woody tissues (stems, branches, and coarse roots). We also hypothesized that differences in [N] would largely explain differences in maintenance or dormant‐season respiration among tissues. For April–November, mean respiration at 15 °C varied from 1.5 to 2.8 μmol kg^?1 s^?1 for fully expanded foliage, 1.7–3.0 for growing foliage, 0.8–1.6 for fine roots, 0.6–1.1 (sapwood) for stems, 0.5–1.8 (sapwood) for branches, and 0.2–1.5 (sapwood) for coarse roots. Growing season variation in respiration for foliage produced the prior year was strongly related to [N] (r² = 0.94), but fine root respiration was not related to [N]. For current‐year needles, respiration did not covary with [N]. Night‐time foliar respiration did not vary in concert with previous‐day photosynthesis for either growing or fully expanded needles. Stem growth explained about one‐third of the seasonal variation in stem respiration (r² = 0.38), and also variation among trees (r² = 0.43). We did not determine the cause of seasonal variation in branch and coarse root respiration, but it is unlikely to be directly related to growth, as the pattern of respiration in coarse roots and branches was not synchronized with stem growth. Seasonal variations in temperature‐corrected respiration rates were not synchronized among tissues, except foliage and branches. Spatial variability in dormant‐season respiration rates was significantly related to tissue N content in foliage (r² = 0.67), stems (r² = 0.45), coarse roots (r² = 0.36), and all tissues combined (r² = 0.83), but not for fine roots and branches. Per unit N, rates for P. strobus varied from 0.22 to 3.4 μmol molN^?1 s^?1 at 15 °C, comparable to those found for other conifers. Accurate estimates of annual autotrophic respiration should reflect seasonal and spatial variation in respiration rates of individual tissues.     

(Chemotaxonomic) Implications of Postharvest/Storage‐Induced Changes in Plant Volatile Profiles – the Case of Artemisia absinthium L. Essential Oil

The plant volatile profile and the essential‐oil chemical composition change during the storage of plant material. The objective of this study was to develop a mathematical model able to predict, explain, and quantify these changes. Mathematical equations, derived under the assumption that the essential oil contained within plant material could be treated as an ideal solution (Raoult's law), were applied for tracking of postharvest changes in the volatile profile of Artemisia absinthium L. (the essential oils were analyzed by GC‐FID and GC/MS). Starting from a specific chemical composition of an essential‐oil sample obtained from plant material after a short drying period (typically 5–10 d), and by using the equations derived from this model, one could easily predict evaporation‐induced changes in the volatile profile of the plant material. Based on the composition of the essential‐oil sample obtained after a given storage time t, it is possible to identify those components that were involved in chemical reactions, both as reactants and possible products. The established model even allowed the recognition of pairs of transformation, i.e., ‘daughter’ products and their ‘parent’ compounds. The obtained results highlight that the essential‐oil composition is highly dependent on the storage period of any plant material and urges caution in different types of phytochemical studies, especially chemotaxonomic ones, or practical application.     

Breeding Phenology of Birds: Mechanisms Underlying Seasonal Declines in the Risk of Nest Predation

Seasonal declines in avian clutch size are well documented, but seasonal variation in other reproductive parameters has received less attention. For example, the probability of complete brood mortality typically explains much of the variation in reproductive success and often varies seasonally, but we know little about the underlying cause of that variation. This oversight is surprising given that nest predation influences many other life-history traits and varies throughout the breeding season in many songbirds. To determine the underlying causes of observed seasonal decreases in risk of nest predation, we modeled nest predation of Dusky Flycatchers (Empidonax oberholseri) in northern California as a function of foliage phenology, energetic demand, developmental stage, conspecific nest density, food availability for nest predators, and nest predator abundance. Seasonal variation in the risk of nest predation was not associated with seasonal changes in energetic demand, conspecific nest density, or predator abundance. Instead, seasonal variation in the risk of nest predation was associated with foliage density (early, but not late, in the breeding season) and seasonal changes in food available to nest predators. Supplemental food provided to nest predators resulted in a numerical response by nest predators, increasing the risk of nest predation at nests that were near supplemental feeders. Our results suggest that seasonal changes in foliage density and factors associated with changes in food availability for nest predators are important drivers of temporal patterns in risk of avian nest predation.     

PHYTOTOXIC VOLATILES FROM TRICHOSTEMA LANCEOLATUM (LABIATAE)

Trichostema lanceolatum Benth. (vinegar weed), an annual herb of the California grassland, contains 2.9 ml of volatile essential oil per 100 g of fresh foliage. Vapors from leaves and extracted oil inhibited growth of other plants in laboratory tests. Volatiles from 0.12–0.15 g green Trichostema leaf caused a 50% reduction in radicle elongation of Bromus mollis L. and Hordeum vulgare L. seeds in petri dishes. Vapors from 1.5 and 3.2 μl essential oil in sealed and non-sealed dishes, respectively, had a similar effect on Hordeum seeds. Exposure of dry Bromus seeds for 1 day, and dry Hordeum seeds for 3 days, to volatiles from Trichostema foliage inhibited growth when the seeds were later moistened. The toxic volatiles had a high affinity for vegetable oil and were not readily removed from seeds by rinsing with water. The major volatile inhibitor from Trichostema was terpinen-4-ol. This monoterpene alcohol was about 0.3 and 1.9 times as inhibitory as camphor and 1,8-cineole, terpenes that have previously been shown to influence vegetation patterning near Salvia leucophylla Greene shrubs. These results suggest Trichostema lanceolatum may also have allelopathic potential.     

Photosynthetic gas exchange and the stable isotope composition of leaf water: comparison of a xylem-tapping mistletoe and its host

Photosynthetic gas exchange and the stable isotopic composition of foliage water were measured for a xylem tapping mistletoe, Phoradendron juniperinum, and its host tree, Juniperus osteosperma, growing in southern Utah. The observed isotopic composition of water extracted from foliage was compared to predictions of the Craig-Gordon model of isotopic enrichment at evaporative sites within leaves. Assimilation rates of juniper were higher and stomatal conductance was lower than the values observed for the mistletoe. This resulted in lower intercellular/ ambient CO₂ values in the juniper tree relative to its mistletoe parasite. For mistletoe, the observed foliage water hydrogen and oxygen isotopic enrichment was less than that predicted by the model. In juniper, foliage water hydrogen isotopic enrichment was also lower than that predicted by the evaporative enrichment model. In contrast, the oxygen isotopic enrichment in juniper foliage water was slightly greater than that predicted for the evaporative sites within leaves. Hydrogen isotopic enrichment in mistletoe foliage shows systematic variation with stem segment, being highest near the tips of the youngest stems and decreasing toward the base of the mistletoe, where isotopic composition is close to that of stem water in the host tree. In a correlated pattern, mid-day stomatal conductance declined abruptly in mistletoe foliage of increasing age.