Effects of monoterpenes on Fomes annosus (Fr.) Cooke and its phenol oxidase activity

Fomes annosus was cultivated subject to vapours of monoterpenes. Three monoterpenes were tested separately: α-pinene, β-pinene and 3-carene. The terpenes inhibited the dry matter production of the fungus but extracellular phenol oxidase activity was increased, particularly when the fungus was exposed to vapours of β-pinene and 3-carene.     

红脂大小蠹诱导油松树干挥发性单萜相对含量的变化

使用Porapak Q吸附剂,采用动态顶空的吸附方法,连续抽取11个不同阶段的对照、损伤与虫害油松的挥发物成分.运用GC、GC-MS与图谱峰面积进行挥发物成分定性与单萜相对含量的定量分析.与对照和损伤油松相比,虫害油松含有高比率的(+)-α-蒎烯(超过90％)和月桂烯,但(+)-3-蒈烯,(-)-β-蒎烯,莰烯和柠檬烯含量较低.(+) -3-蒈烯含量对照和损伤油松高于虫害油松(低于4％).(+)-3-蒈烯含量从损伤4天后的最低水平逐渐恢复到对照油松中含量水平.(-)-β-蒎烯和柠檬烯在不同处理的油松中含量相近,但在接入雌雄虫后3个处理间存在显著差异.尽管目前不确定我国的红脂大小蠢是否在危害油松后释放信息素,但研究表明红脂大小蠢可能会利用各种单萜成分细节上的变化作为化学信号,从而实现寄主的选择和种群聚集.本研究对于揭示油松抗性机制,完善红脂大小蠢的监测与防控技术体系具有重要意义.     

Antifungal properties of terpenoids in Picea abies against Heterobasidion parviporum

The antifungal properties of 14 major oleoresin‐constitutive terpenoids of Norway spruce (Picea abies) against Heterobasidion parviporum were evaluated in vitro at three gradient concentrations, 0.1, 0.2 and 0.4 μmol/cm², on potato dextrose agar medium. Eight monoterpene hydrocarbons (+)‐ and (?)‐α‐pinene, (?)‐β‐pinene, (+)‐3‐carene, myrcene, (+)‐ and (?)‐limonene, terpinolene; four oxygenated monoterpenes α‐terpineol, terpinen‐4‐ol, 1,8‐cineole, bornyl acetate; and two resin acids abietic acid and dehydroabietic acid were selected. Abietic and dehydroabietic acids showed the highest antifungal activities at all concentrations. Among oxygenated monoterpenes, bornyl acetate and α‐terpineol showed antifungal activity at the highest concentration. Among monoterpene hydrocarbons, (+)‐α‐pinene showed similar activity to terpinen‐4‐ol and 1,8‐cineole at the highest concentration; however, it was lower than α‐terpineol and bornyl acetate. Other monoterpene hydrocarbons inhibited mycelial growth by <10%. Re‐extraction of medium surfaces after the test period revealed that most α‐terpineol and terpinen‐4‐ol remained unchanged on the surface but monoterpene hydrocarbons completely disappeared. However, notable fungal transformed products were observed on surfaces applied with 1,8‐cineole and bornyl acetate. Thus, mycelial growth inhibition of monoterpenoids might be caused by complex functions such as biodegradation and/or detoxification by interaction between mycelium and compound. These results provide a basis for future studies considering the role of chemodiversity in the comprehensive chemical defence of P. abies.     

Individual variations in monoterpenes released from Cryptomeria japonica and Pinus thunbergii needles

Variations in the compositions of low boiling point (LBP) monoterpenes in needle samples from 99 sugi (Cryptomeria japonica) and 100 kuromatsu (Pinus thunbergii) trees were investigated using a headspace technique. Considerable variations in the proportions of monoterpenes were revealed in both species. In sugi, the proportions of sabinene and α-pinene in the total LBP monoterpenes, ranging from 8.8% to 73.3% and from 14.5% to 73.3%, respectively, showed enormous variations among nine monoterpenes. The proportions of 3-carene and limonene, ranging from 0.1% to 29.5% and from 0.2% to 20.4%, respectively, also showed very specific variations. In kuromatsu, the proportions of β-pinene and α-pinene in the total LBP monoterpenes, ranging from 26.5% to 66.3% and from 18.7% to 46.9%, respectively, showed considerable variations among ten monoterpenes. The proportions of myrcene and 1,8-cineole, ranging from 0.9% to 18.5% and from 0.8% to 12.3%, respectively, also showed specific variations. Part of this article was presented at the 50th Annual Meeting of the Japan Wood Research Society, Kyoto, April, 2000, and the 13th Annual Meeting of the Chugoku Shikoku Branch of the Japan Wood Research Society, Okayama, September 2001     

Growth and spore germination of Cylindrocarpon destructans in associative cultures with bacteria and actinomycetes1

Studies were made on the effect of bacteria and actinomycetes on growth and spore germination of Cylindrocarpon destructans. The effect of bacteria on growth of this fungus as well as on spore germination was statistically not significant. The actinomycetes in general inhibited or had no influence on growth and germination of conidia of C. destructans.     

The growth-promoting activity of terpenoids on wood-decomposing fungi

Linear growth of wood-decomposing fungi on an agar medium was usually retarded, but in some cases enhanced, by terpenoids in gaseous form. Increased dry matter production was demonstrated in some Coniophora, Peniophora, Stereum and Polyporus species exposed to the vapours of longifolene, α-pinene, β-pinene, Δ-3-carene, limonene or a mixture of cuparene and thujopsene. The positive response to longifolene in some cases seemed to involve a more efficient utilisation of the glucose in the medium.     

Electrophysiological responses of <Emphasis Type="Italic">Thaumetopoea pityocampa</Emphasis> females to host volatiles: implications for host selection of active and inactive terpenes

Volatiles from newly cut branches with needles of Pinus sylvestris L. were collected with headspace sampling technique, and then identified and quantified by combined gas chromatographic-mass spectrometry (GC-MS). The response of antennae of the female pine processionary moth, Thaumetopoea pityocampa, to these volatiles was recorded by coupled gas chromatographic-electroantennographic detection (GC-EAD). Surprisingly, the most common and major monoterpene hydrocarbons (MT), α-pinene, 3-carene, and β-pinene were antennally inactive. Female antennae responded strongly only to four minor MT components, myrcene, β-phellandrene, trans-β-ocimene, and terpinolene. Weaker, but repeatable responses were also found to limonene, cis-β-ocimene, and γ-terpinene. Further EAD recordings with two synthetic MT mixtures supported our findings from the natural material. When separating the two enantiomers of limonene by running different synthetic MT mixtures, the EAD response was found only to the(?)-enantiomer, but not to the opposite (+)-enantiomer. EAD-responses were also found to some less volatile compounds, such as sesquiterpenes (SqT), active at ng-levels. The sensitivity and specificity of the antenna to a select number of active host MTs and SqTs suggest that these play a role in the host selection process of T. pityocampa females.     

Neuropharmacological activities of phytoncide released from <Emphasis Type="Italic">Cryptomeria japonica</Emphasis>

Forest-air bathing and walking (shinrin-yoku) is beneficial to human heath. In this study the phytoncide (volatile compounds) released from Cryptomeria japonica plantation forest was characterized by using solid-phase microextraction (SPME) and gas chromatography-mass spectrometry (GC-MS). The main volatile compounds were α-pinene (19.35%), β-myrcene (16.98%), d-limonene (15.21%), and γ-muurolene (7.42%). Furthermore, the neuropharmacological activity of the essential oils from leaves of C. japonica (ECJ) was evaluated by several animal behavior tests. ECJ could prolong the sleeping phase of ICR (imprinting control region) mice in the pentobarbital-induced sleeping time model. Furthermore, both EJC and one of its monoterpenes, d-limonene, possessed potent anxiolytic and analgesic activities based on the results obtained from elevated plus maze and writhing tests. The volatile compounds released from C. japonica provide relaxing and stress-relieving effects on mice, and further study on the effect of phytoncide on humans is worthwhile.     

Studies on ectomycorrhizae of pine

Infection of feeder roots of Pinus echinata by the ectomycorrhizal fungus, Pisolithus tinctorius, resulted in an approximate 40-fold increase in the level of 3-carene, and Ccnococcum graniforme induced an approximate 30-fold increase in β-phellandrene. Vapors of these volatile compounds affected the vegetative growth of different ectomycorrhizal and root pathogenic fungi to different degrees in laboratory experiments.     

Chemical structures of p-menthane monoterpenes with special reference to their effect on seed germination and termite mortality

A series of p-menthane monoterpenes was investigated to confirm any correlation between their bioactivity (effect on seed germination and termite mortality) and chemical structure. The germination percentages of Brassica rapa seeds at a concentration of 0.1 mg/Petri dish of (+)-pulegone, isopulegol, piperitone, (?)-dihydrocarveol, terpinen-4-ol and (?)-menthol were found to be 21.6, 27.3, 27.3, 29.1, 42.9 and 43.4, respectively. The lethal concentration 50 values of carvacrol, (+)-pulegone, thymol, (?)-menthol and (?)-terpinen-4-ol for termites (Reticulitermes speratus) were 0.34, 0.50, 0.65, 0.92 and 1.26 (mg/Petri dish), respectively. Of all the compounds tested, phenols produced the highest levels of termite mortality, with ketones and alcohols also showing bioactivity. An assessment of the bioactivity revealed that the presence of a phenol group was effective for termite mortality, with a carbonyl group also showing strong bioactivity. The presence of an alcohol or isopropyl group in a ring also contributed to the bioactivity, whereas the presence of an isopropenyl group at the same position, however, exhibited an inhibitory effect on seed germination. In conclusion, the bioactivity of the p-menthane monoterpenoids was dependent upon the presence and position of certain functional groups and the degree of saturation in the functional group of the side chain.     

The effect of nitrogen fertilization on fungistatic phenolic compounds in roots of beech (Fagus sylvatica) and Norway spruce (Picea abies)

The effect of nitrogen fertilization on fungistatic phenolic compounds in fine roots of beech and Norway spruce growing in afforestation plots was analysed. The plots were situated at two sites in Switzerland on acidic soil with low base saturation. For 9 years, the trees have been treated with dry ammonium nitrate to give 0, 10, 20, 40, 80, 160 kg N ha^?1 year^?1, respectively. The phenolic compounds responded differently to fertilization. Fine roots of beech showed a significant decrease of (?)‐epicatechin and piceatannol with increasing nitrogen fertilization. The concentration of protocatechuic acid was increased with fertilization. Roots of fertilized Norway spruce showed significantly decreased concentrations of 4‐hydroxyacetophenone and piceatannol. The mycelial growth of three isolates each of Heterobasidion annosum s.l. and Cylindrocarpon destructans was tested on agar media containing various phenolic compounds in concentrations found in fine roots of Norway spruce (Picea abies) and beech (Fagus sylvatica). All three H. annosum isolates were inhibited by p‐coumaric acid and (?)‐epicatechin. Two isolates were inhibited by another four phenolic compounds (p‐hydroxybenzoic acid, 4‐hydroxyacetophenone, piceatannol and protocatechuic acid), one by (+)‐catechin. Two of three C. destructans isolates were inhibited by all phenolic compounds except for (+)‐catechin which affected only one isolate, one isolate did not respond at all.     

Chemical composition,phytotoxic and antifungal activities of <Emphasis Type="Italic">Pinus pinea</Emphasis> essential oil

The chemical composition of essential oils isolated by hydrodistillation from the aerial parts of Tunisian Pinus pinea Linn. was analyzed by GC and GC/MS. Sixty-six compounds were identified, representing 98.5% of total oil, which was found to be rich in monoterpene hydrocarbons (73.1%) particularly limonene (54.1%), α-pinene (7.7%), and β-pinene (3.4%). The yield and the physico-chemical properties were determined. Results of the antifungal activity study by in vitro contact assay showed that P. pinea oil significantly inhibited the growth of ten plant pathogenic fungi. Moreover, herbicidal properties of the oil, tested on Sinapis arvensis L., Lolium rigidum Gaud., and Raphanus raphanistrum L., indicated that the oil completely inhibited the seed germination at a high concentration, while at low doses the oil acted by decreasing and delaying the germination and inhibiting the seedling growth of all tested weeds unlike the commercial herbicide. Our results showed that P. pinea essential oil could be valorized as bioproduct for biocontrol of weeds and fungal plant diseases.     

Analyses of BioVOCs variation related to vegetation predominance in the natural park of ampezzo dolomites, UNESCO world heritage area of dolomites

The determination of emitted Biogenic Volatile Compounds (BioVOCs) profile via Field Air Analysis (FAA) — Solid Phase Micro Extraction (75 μm Carboxen/PDMS portable field sampler) was performed using GC-MS. The six sampling sites located in the Natural Park of Ampezzo Dolomites, part of the UNESCO’s World Heritage List, are characterized by different predominating vegetation. The ubiquitous compound hexanal was chosen as internal standard, in order to compare the amounts of the different compound in the different sites. The main terpenes identified were α-pinene, β-pinene, δ-3-carene and d-limonene, while 1,8 cineole was the highest abundant oxygenated terpene. In the site next the national road a higher amount of benzene derivatives (benzene, toluene, o-xylene, p-xylene and ethylbenzene) were observed. In the site relatively close to the road a marked decrease of benzene derivatives was observed. In the sites close to conifers (i.e. Fir, Pine and Larch) the terpenic content observed was higher than in the site close to the mixed forest (mainly large-leaf and some conifers). Some terpenes were observed also in the high-quote meadow site, although of lower abundance than in the other sites. The highest abundance of terpenes was observed in the Pinus cembra (Swiss Pine) site.     

Effect of (+)-limonene and 1-methoxy-2-propanol on Ips typographus response to pheromone blends

We compared two different strategies to increase the catches of Ips typographus (L.), particularly males, in pheromone-baited traps. The first of these strategies, the barrier approach, used alternating pheromone blends, targeting males and females respectively, in closely-spaced traps forming a barrier around forest stands. The second strategy, the single trap approach, used widely-spaced traps that were all baited with the same lure and intended to trap the highest possible numbers of males without compromising trapping of females. In the blend used for the barrier traps targeting primarily males, with a lower percentage of (4S)-cis-verbenol (cV), the (−)-α-pinene was replaced step wise with (+)-limonene at rates of 0%, 1%, 10%, 35%, 60% and 90%. This replacement had no significant effect on the numbers of responding I. typographus males, but there was a slight effect on the percentage of males caught. In the attractant blend for the barrier traps targeting females, with a higher percentage of cV, the 2-methyl-3-buten-2-ol (MB) was replaced with 1-methoxy-2-propanol (MP) in a similar fashion as for the male-specific blends. The replacement did not significantly affect the catch of females. Thus, it is possible to use the MP in the blend with cV and ipsdienol without significant change in catch efficacy. In the blends for single traps, the (−)-α- pinene was replaced with (+)-limonene and MB with MP. The replacement of (−)-α-pinene had only a slight effect on the percentage of males, but the results suggest that replacing MB with MP in the blend will not significantly reduce trapping efficacy. Foundation project: The research was supported by Slovak Research and Development Agency (APVV-51-P06005 and APVV-27-P05205) and by the Scientific Grant Agency of the Ministry of Education of the Slovak Republic and the Slovak Academy of Sciences (2/6153/26)     

Electroantennogram responses of Dendrolimus superans (Lepidoptera: Lasiocampidae) to six volatiles of Larix gmelinii

Dendrolimus superans is one of the important pests feeding on the needles of Larix gmelinii. Six standard compounds, (1R)-(−)-α-pinene, (1S)-(−)-α-pinene, ocimene, (1S)-(−)-β-pinene, R(−)-α-phellandrene and camphene, the main volatiles of L. gmelinii were used to test the electroantennogram (EAG) responses of moths. The results show that the order of the EAG responses of moths to seven concentrations of these six compounds were as follows: mated females > virgin females > unmated males, except for 0.1 μL/μL R(−)-α-phellandrene, where the order was: virgin females > mated females > unmated males. There are statistically significant differences between the EAG responses of virgin females and unmated males (p < 0.05), and also between mated females with virgin females and mated females and unmated males (p < 0.01), which suggests that the mated females are more sensitive to the volatiles of host plant. The results of EAG responses of the mated females, virgin females and unmated males indicate that they are more sensitive to R(−)-α-phellandrene than to the other volatile components. The active time for the EAG responses of both mated females and unmated males occurs during the night, i.e., from 20:00 to 04:00 hours. This is consistent with their eclosion, mating and oviposition periods. __________ Translated from Scientia Silvae Sinicae, 2007, 43(7): 55–60 [译自:林业科学]     

Effect of an ectomycorrhizal fungus,Laccaria laccata,on Fusarium damping-off in Pinus banksiana seedlings

Damping-off caused by Fusarium oxysporum Schlecht in Pinus banksiana Lamb, was reduced significantly when inoculated with an ectomycorrhizal fungus, Laccaria laccata (Scop. ex Fr.) Berk. and Br. In paired culture, growth of F. oxysporum was significantly reduced by L. laccata. The number of colony forming units of F. oxysporum was reduced significantly in the rhizosphere of P. banksiana seedlings when inoculated with L. laccata. Spore germination and germ tube length of F. oxysporum was inhibited strongly by culture filtrate of L. laccata and root exudate of P. banksiana inoculated with L. laccata. Mycorrhizal seedlings had significantly higher amount of total soluble phenols than nonmycorrhizal ones.     

Allelopathic effects of invasive Eucalyptus camaldulensis on germination and early growth of four native species in the Western Cape,South Africa

Eucalyptus camaldulensis Dehnh. (red river gum; Myrtaceae) is an invasive tree in riparian habitats of the Western Cape, South Africa, where it replaces indigenous vegetation and affects ecosystem functioning. These invasions lead to changes in river geomorphology and reduction in stream flow. The mechanisms that drive these effects are poorly understood. The potential for allelopathic effects of aqueous extracts of E. camaldulensis tissues and of soil and litter collected beneath E. camaldulensis trees on the germination and seedling growth of four selected native plant species was investigated in a greenhouse experiment. Soils collected beneath E. camaldulensis trees were used in three treatments: untreated soils, sterilised soils and sterilised soils overlaid with a eucalypt litter layer. In addition, soils collected from underneath native species were used in two treatments: untreated soils and soils overlaid with a eucalypt litter layer. All soil treatments were watered with three E. camaldulensis leaf, bark and root aqueous treatments. Compounds present in the aqueous extracts and fresh samples were identified using gas chromatography. Soil and aqueous treatments showed varying effects on germination and seedling growth of the four native species. Germination and seedling growth of Olea europaea subsp. africana and Dimorphotheca pluvialis were significantly reduced by E. camaldulensis root and bark aqueous extracts as well as by the soils treatments. The addition of eucalypt litter to native and sterilised soils reduced shoot and root growth of all four native species. Compounds such as -phellandrene, eucalyptol, p-menth-1-en-8-ol and -pinene, which have the potential to inhibit germination and plant growth, were identified in E. camaldulensis aqueous extracts and fresh samples. Although the methods applied in this study had limitations (e.g. lack of control treatment to litter addition), the results provide an additional motivation to prioritise removal of invasive E. camaldulensis stands from riparian ecosystems. Restoration initiatives should target native species that are not negatively affected by allelopathy.     

Association between temperature,relative humidity and concentration of volatile organic compounds from wooden furniture in a model room

Abstract

Emissions of volatile organic compounds (VOCs) from wooden furniture in a child's room were investigated. A model room was set up in a 12?m³ test chamber, and in parallel, a scaled-down version was run in a 1?m³ test chamber. The latter had a steady climate of 23°C/50% relative humidity (RH), while the temperature and humidity conditions were varied in the 12?m³ chamber between 18 and 28°C, and 30 and 80% RH. Compounds found were α-pinene, β-pinene, 3-carene, limonene and hexanal. Variations in the climate showed that there is an association between temperature and room concentrations of all found VOCs. Changes in RH showed effect on hexanal concentration, and all monoterpene concentrations remained unaffected.     

Effects of oleoresins and monoterpenes on in vitro growth of fungi associated with pine decline in the Southern United States

As a means of exploring pine resistance to root disease and declines, the effects of host plant secondary metabolites on the growth of root colonizing fungi associated with three diseases/declines of southern pines – loblolly pine decline, littleleaf disease and annosum root rot were tested. The associated fungi –Leptographium huntii, L. serpens, L. terebrantis, L. procerum, Heterobasidion annosum and Phytophthora cinnamomi– were grown in saturated atmospheres or in direct contact with, pure monoterpenes and crude oleoresin collected from the four southern pines (Pinus taeda, P. eschinata, P. palustris and P. elliotti) for 7 day. Fungal growth was measured at 3, 5 and 7 day. Root‐infecting fungi differed significantly in sensitivity to crude oleoresin and pure monoterpenes. All fungi tested were inhibited, to some extent, by the resins tested. H. annosum and P. cinnamomi were strongly inhibited by all the monoterpenes tested. The ophiostomatoid fungi were significantly less affected by the compounds tested. L. huntii and L. serpens were less inhibited by monoterpenes than either L. terebrantis or L. procerum. These fungal growth studies show that the kind and amount of secondary metabolite produced by the host plant have a profound effect on tree pathogens. Alterations of tree physiology may have implications for defenses against tree pathogens as well as to the ecology and management of forest ecosystems. Difference in incidence of root disease observed in the field may be explained by the ability of the fungus to tolerate these host defense mechanisms.     

(+)-柠檬烯和1-甲氧基-2-丙醇对云杉八齿小蠹虫对信息素混合物反映的影响(英文)

对利用信息素诱捕云杉八齿小蠹的策略进行了对比分析,尤其是雄性小蠹的诱捕。第一种策略是障碍法,在林分的周围密集的布置捕捉陷阱,使用交互式信息素分别诱捕雄性小蠹和雌性小蠹。第二种策略是单一诱捕法,广阔使用投有相同诱饵诱捕陷阱,以捕捉最大数量的雄性小蠹为目的,而不包含雌性小蠹的捕捉。在带有低含量的(4S)一反式马鞭草烯醇诱饵混合物中,用0%,1%,10%,35%,60%and90%的(+)-柠檬烯逐步取代α-蒎烯。这种替换对雄性小蠹的反映数量没有影响,但对雄性小蠹的捕捉量稍有影响。在有高含量(4S)-反式马鞭草烯醇捕捉雌性小蠹的引诱剂混合物中,用1-甲氧基-2-丙醇取代2-甲基-3-丁烯-2-醇,对雌性小蠹的捕捉率没有影响。因而,在具有反式马鞭草烯醇和(4县)-2-甲基-6-甲基-2,7-辛-4-醇的混合物中使用1-甲氧基-2-丙醇,捕捉效果没有明显的变化。在单一捕捉的引诱剂混合物中,用(+)-柠檬烯取代α-蒎烯,用1-甲氧基-2-丙醇取代2-甲基-3-丁烯-2-醇,α-蒎烯被代替后对雄性小蠹的捕捉率轻微的影响,但2-甲基-3-丁烯-2-醇被代替后,将不会没有明显地降低捕捉效果。