Acaricidal effects of quinone and its congeners and color alteration of Dermatophagoides spp. with quinone

Acaricidal activity of the active constituent derived from Pyrus ussuriensis fruits against Dermatophagoides farinae and D. pteronyssinus was examined and compared with that of the commercial benzyl benzoate. The LD50 value of the ethyl acetate fraction obtained from the aqueous extract of P ussuriensis fruits was 9.51 and 8.59 microg/cm3 against D. farinae and D. pteronyssinus, respectively. The active constituent was identified as quinone by spectroscopic analyses. On the basis of LD50 values with quinone and its congeners, the compound most toxic against D. farinae was quinone (1.19 microg/cm3), followed by quinaldine (1.46), benzyl benzoate (9.32), 4-quinolinol (86.55), quinine (89.16), and 2-quinolinol (91.13). Against D. pteronyssinus, these were quinone (1.02 microg/ cm3), followed by quinaldine (1.29), benzyl benzoate (8.54), 4-quinolinol (78.63), quinine (82.33), and 2-quinolinol (86.24). These results indicate that the acaricidal activity of the aqueous extracts can be mostly attributed to quinone. Quinone was about 7.8 and 8.4 times more toxic than benzyl benzoate against D. farinae and D. pteronyssinus. Additionally, quinaldine was about 6.4 and 6.6 times more toxic than benzyl benzoate against D. farinae and D. pteronyssinus, respectively. Furthermore, the skin color of the dust mites was changed from colorless-transparent to dark brown-black by the treatment of quinone. These results indicate that quinone can be very useful as potential control agents, lead compounds, or the indicator of house dust mites.     

Acaricidal activity and function of mite indicator using plumbagin and its derivatives isolated from Diospyros kaki Thunb. roots (Ebenaceae)

Acaricidal effects of materials derived from Diospyros kaki roots against Dermatophagoides farinae and D. pteronyssinus were assessed using impregnated fabric disk bioassay and compared with that of the commercial benzyl benzoate. The observed responses varied according to dosage and mite species. The LD50 values of the chloroform extract of Diospyros kaki roots were 1.66 and 0.96 microg/cm2 against D. farinae and D. pteronyssinus. The chloroform extract of Diospyros kaki roots was approximately 15.2 more toxic than benzyl benzoate against D. farinae, and 7.6 times more toxic against D. pteronyssinus. Purification of the biologically active constituent from D. kaki roots was done by using silica gel chromatography and high-performance liquid chromatography. The structure of the acaricidal component was analyzed by GCMS, 1H-NMR, 13C-NMR, 1H-13C COSY-NMR, and DEPTNMR spectra, and identified as plumbagin. The acaricidal activity of plumbagin and its derivatives (naphthazarin, dichlon, 2,3-dibromo-1,4-naphthoquinone, and 2-bromo-1,4- naphthoquinone) was examined. On the basis of LD50 values, the most toxic compound against D. farinae was naphthazarin (0.011 microg/cm2) followed by plumbagin (0.019 microg/cm2), 2- bromo-1,4-naphthoquinone (0.079 microg/cm2), dichlon (0.422 microg/ cm2), and benzyl benzoate (9.14 microg/cm2). Additionally, the skin color of the dust mites was changed from colorless-transparent to dark brown-black by the treatment of plumbagin. Similar results have been exhibited in its derivatives (naphthazarin, dichlon, and 2-bromo-1,4-naphthoquinone). In contrast, little or no discoloration was observed for benzyl benzoate. From this point of view, plumbagin and its derivatives can be very useful for the potential control agents, lead compounds, and indicator of house dust mites.     

Microbial transformation of geraniol and nerol by Botrytis cinerea

Summary Biotransformation of geraniol 1A and nerol 1B was studied with four strains of Botrytis cinerea and three growth media. Using grape must predominant conversion of 1A/1B to E-3,7-dimethyl-2-octen-1,8-diol 5 and 2Z,6E-3,7-dimethyl-2,6-octadien-1,8-diol 16B was observed. However, with one strain and 1A, E-2-methyl-2-hepten-6-one-1-ol 2B, 7-hydroxy-6-methyl-2-heptanone 3 and p-menth-1-ene-9-ol 7 were identified as major metabolites. As further fungal bioconversion products of 1A/1B were detected: Z-2-methyl-2-hepten-6-one-1-ol 2A, 2E,6Z-, 2E,6E-and 2Z,6Z-3,7-dimethyl-2,6-octadien-1,8-diol 4A/4B/16A, Z-3,7-dimethyl-2-octen-1,8-diol 17, 3,7-dimethyl-1,8-octandiol 6, 2E,6E-8-hydroxy-2,6-dimethyl-2,6-octadienal 8, geranial and neral 9, 18, citronellol 10, Z- and E-2,6-dimethyl-2,7-octadien-1,6-diol 13A/13B, 6-hydroxy-2,6-dimethyl-2,7-octadienal 14 as well as 2,6-dimethyl-7-octen-1,6-diol 15. Using synthetic growth medium again -hydroxylation reactions were observed, but 2-methyl-2-hepten-6-one 11 and 7 were also identified as major bioconversion products of 1A and 1B, respectively. Additionally, 2-methyl-2-hepten-6-ol 12 was detected and, using 1B, also traces of 2Z,6E-8-hydroxy-2,6-dimethyl-2,6-octadienal 19 and two 3,9-epoxy-p-menth-1-ene isomers 20A/20B were found. Addition of small amounts of grape must to the synthetic medium (1:700 to 5:700) influenced both the yields of metabolites and their qualitative and quantitative distribution. Identifications of biotransformation products of 1A/1B were performed by capillary gas chromatography (HRGC) and coupled HRGC techniques, i.2. on-line-mass spectrometry (HRGC-MS) and-Fourier transform infrared spectroscopy (HRGC-FTIR) after extractive sample preparation.     

Decrease in DEET repellency caused by nitric oxide in Rhodnius prolixus

N,N-diethyl-3-methylbenzamide (DEET) is widely used as an insect repellent; however, little is known about its mode of action. On the other hand, nitric oxide (NO) participates in the olfaction transduction pathway of insects. In this work, nitroso-acetyl-cysteine (SNAC), a nitric oxide donor, or dibutyril-cyclic-GMP (db-cGMP), the cyclic nucleotide analog, were applied on fifth instar nymphs of Rhodnius prolixus before exposing them to DEET, to obtain information about the possible role of NO/cGMP system in the olfaction process. In the first place, we exposed the nymphs to several DEET concentrations (70, 700, 1,750, and 3,500 microg/cm2). All these concentrations produced a repellent effect. A decrease in repellency during the course of the experiment was observed when the nymphs were exposed to high concentrations of DEET (700 and 1,750 microg/cm2), suggesting an adaptation phenomenon. The pre-treatment of the insects with 15 microg /insect of SNAC or 2 microg/insect of db-cGMP produced a reduction of the repellency. An increase in locomotor activity was observed in insects exposed to 350 or 700 microg/cm2 DEET. Although exposure to 70 microg/cm2 DEET produced a high repellency response, it did not modify the insects' locomotor activity. Insects treated with two doses of SNAC before being exposed to 350 microg/cm2 of DEET showed no differences in locomotor activity compared to controls.     

The in vitro substrate regiospecificity of recombinant UGT85B1, the cyanohydrin glucosyltransferase from Sorghum bicolor

The in vitro substrate specificity of UDP-glucose:p-hydroxymandelonitrile-O-glucosyltransferase from Sorghum bicolor (UGT85B1) was examined using a range of potential acceptor molecules, including cyanohydrins, terpenoids, phenolics, hexanol derivatives and plant hormones. Qualitative enzyme activity assays employing 20 different putative substrates were performed and 15 proved to be glucosylated using recombinant UGT85B1 isolated from Escherichia coli. K(m) and k(cat) values were determined for nine of these substrates including mandelonitrile, geraniol, nerol and beta-citronellol, 2-hydroxy-3-methoxybenzyl alcohol, 1-hexanol, cis-3-hexen-1-ol, 3-methyl-3-buten-1-ol and 3-methyl-2-buten-1-ol. UGT85B1 has a rather broad substrate specificity in vitro but shows regiospecificity, demanding the presence of a sterically unhindered hydroxyl group e.g. as part of a cyanohydrin function, as a primary alcohol or as a phenolic hydroxyl group and being influenced by the stereochemistry and/or interactive chemistry of the substituents on the hydroxyl-bearing carbon atom.     

山西省晋中市及周边地区螨虫分布状况和优势螨种的研究

目的 研究山西省晋中市及周边地区的尘螨种类和优势螨种.方法 以就诊于晋中市第一人民医院耳鼻喉科门诊的尘螨过敏患者为研究对象,从2009年12月至2011年10月对居住在晋中市及周边地区的30户家庭进行入户采集调查.采集尘样后经过分离,制片,最后进行鉴定.结果 共采集尘样196份,户尘螨占成螨总数的60.1％,粉尘螨占39.8％.通过对不同采集地点的调查结果显示,楼房的样本阳性率为35.8％,平房的样本阳性率为21.8％.通过对不同环境样本中螨密度的统计,枕头的螨密度最高,为166.7头/g.平均螨密度在全年有2个高峰期,分别是7-8月份和12～2月.结论 晋中市及周边地区的主要螨种为麦食螨科的户尘螨和粉尘螨,户尘螨为优势螨种.     

Studies on the Aroma Constituents of Fuiien Ti Kuan Yin Tea,Se Chung Tea,Wu-I Shui Hsien Tea and Wu-I Chi Chung Tea in China

This paper reports, for the first time, the aroma constituents of the famous Fujian Oolong tea—Ti kuan Yin Tea, Se Chung Tea, Wu-I Shut Hsien Tea and Wu-I Chi Chung Tea. 70 aroma concentrates of tea samples were identified by the use of (IC-MS, SCOT capillary coumn GC standard sample addition method and IR. Among which benzyl alcohol, translinalooloxide (furanoid), cis-linalooloxide (fuconoid), 3,7-dimeihy-l,5, 7-octatrien-3-ol, β-phenylethanol, translinalooloxide (pyranoid), geraniol, indole, eisjasmone, pasmine laetone, nerolidol and mthyl jasmonate are the typical character the aroma constituents. Consequently the aroma is varied by different varieties of the tea, different regions of their growth and different processing.     

Degradation of the methyl substituted alkene, citronellol, by Pseudomonas aeruginosa, wild type and mutant strains

Pseudomonas aeruginosa W51D used citronellol (3,7-dimethyl-6-octen-1-ol) as sole source of carbon and oxidized it to citronellal, citronellic acid and finally to geranic acid. A mutant derived from this strain was isolated as unable to degrade citronellol and had diminished (93%) citronellal dehydrogenase activity.     

茶梢和茶花主要挥发物对门氏食蚜蝇和大草蛉引诱效应

用Y形嗅觉仪进行的生测表明茶二叉蚜和蚜害茶梢复合体挥发物显著引诱门氏食蚜蝇和大草蛉．剂量为10^-4g·ml^-1时,在味源和空气对照之间,食蚜蝇对源于复合体的香叶醇和水杨酸甲酯、源于完整茶梢的正辛醇、源于茶花的橙花醇有极显著趋性(P<0．01),对源于复合体的反-2-己烯-1-醇、反-2-己烯醛、罗勒烯和芳樟醇有显著趋性(P<0．05);大草蛉则显著趋向源于完整茶梢的正辛醇和己醛(P<0．05)．剂量为10^-2g·ml^-1时,食蚜蝇对己醛、橙花醇及源于复合体的苯甲醛有显著趋性,大草蛉显著趋向于苯甲醛、己醛、香叶醇和反-2-己烯-1-醇．结果表明,除了醛类和水杨酸甲酯外,香叶醇、正辛醇和反-2-己烯-1-醇等也有显著引诱效应。2种天敌对信息物的反应是有阈值的,两种剂量的己醛均显著引诱大草蛉,橙花醇是引导食蚜蝇朝茶花定向的信息物。     

Evidence for geraniol as an obligatory precursor of isothujone

Isothujone (trans-thujan-3-one) was formed from MVA-[¹⁴C, ³H] in Tanacetum vulgare with retention of the pro-(4R) hydrogen of precursor, but with loss of the pro-(4S) hydrogen and of one hydrogen from C-5. Cell-free extracts could not sustain the formation of isothujone from MVA but yielded geraniol and nerol (3,7-dimethylocta-trans-2,6-dien-1-ol and its cis isomer) with retention of the pro-(4R) and loss of the pro-(4S) hydrogen in each case: no hydrogen was lost from C-5 of MVA in formation of geraniol, but one such atom was lost in the formation of nerol. These results support the sequence: geraniol → nerol → isothujone: in which the first two compounds (or their biogenetic equivalents) are interconverted by a redox process involving their derived aldehydes. They are not consistent with a direct pathway to nerol from C₅ intermediates or with routes involving cyclisation of linalol (3,7-dimethylocta-1,6-dien-3-ol) formed directly from the C₅ compounds or from geraniol. The cell-free preparations could not interconvert geraniol and nerol, their phosphates or pyrophosphates. This may be due to the inability of a prenyltransferase-isomerase multi-enzyme system to accept exogenously-supplied intermediates under these (in vitro) conditions.     

羽叶鬼灯檠中的单萜二糖苷

从羽叶鬼灯檠 (RodgersiapinnataFranch .)的根茎中分离得到 6个单萜二糖苷 ,它们的结构通过波谱方法分别鉴定为 :(E ) 3,7 dimethyl 1 O [α L rhamnopyranosyl (1→ 6 ) β D glu copyranosyl] oct 2 en 7 ol (1) ,(E ) 3,7 dimethyl 1 O [α L arabinofuranosyl (1→ 6 ) β D glucopy ranosyl] oct 2 en 7 ol (2 ) ,geranyl 1 O α L arabinofuranosyl (1→ 6 ) β D glucopyranoside (3) ,gera nyl 1 O α L rhamnopyranosyl (1→ 6 ) β D glucopyranoside (4 ) ,geranyl 1 O β D xylopyranosyl (1→6 ) β D glucopyranoside (5 ) ,geranyl 1 O α L arabinopyranosyl (1→ 6 ) β D glucopyranoside (6 )。其中化合物 1为新化合物 ,单萜二糖苷类化合物系首次在该属中发现。     

Clinical Significance of Skin Reactions to Mite Extracts in Children with Asthma

The mite Dermatophagoides pteronyssinus has been identified in dust from the houses of children in Birmingham suffering from asthma. Skin tests were carried out on 150 asthmatic children with extracts of D. pteronyssinus, of the related species D. farinae, of other mites found in house dust, and of crude house dust. Though positive reactions to D. pteronyssinus were obtained more frequently and were of greater size than those to the other extracts, it was considered that D. farinae is a suitable substitute for D. pteronyssinus for skin testing.In further tests on 302 asthmatic children with mite extracts and with extracts of allergens obtained commercially reactions to the former extracts were much more common than reactions to the latter.Major skin reactions (weals with diameter of 5 mm. or more) were present in 77% of children with a history of perennial asthma and house-dust sensitivity. Hence allergy to house-dust mites, particularly D. pteronyssinus, is of considerable importance in childhood asthma, and further study of the ecology and control of the mites in dust is desirable.     

Acaricidal activities of bicyclic monoterpene ketones from Artemisia iwayomogi against Dermatophagoides spp.

The acaricidal properties of 1,7,7-trimethylbicyclo[2.2.1]heptan-2-one isolated from Artemisia iwayomogi and its structural analogues were evaluated against Dermatophagoides farinae and D. pteronyssinus, and their effects were compared with that of the commercial acaricide benzyl benzoate. Based on the 50 % lethal dose (LD₅₀) values against D. farinae, 1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (0.82 μg/cm²) was 9.71 times more effective than benzyl benzoate (7.96 μg/cm²), followed by (1R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (1.03 μg/cm²), (1S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (1.58 μg/cm²), and (1R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one oxime (3.05 μg/cm²) in a filter paper bioassay. The acaricidal activities of 1,7,7-trimethylbicyclo[2.2.1]heptan-2-one and its structural analogues against D. pteronyssinus were similar to those against D. farinae. These results demonstrate that naturally occurring A. iwayomogi-isolated 1,7,7-trimethylbicyclo[2.2.1]heptan-2-one and its structural analogues are suitable for the production of natural acaricides against house dust mites.     

Chemoenzymatic synthesis of (E)-3,7-dimethyl-2-octene-1,8-diol isolated from the hairpencils of male Danaus chrysippus (African Monarch)

The synthesis of (E)-3,7-dimethyl-2-octene-1,8-diol (1), which was isolated from the hairpencils of male Danaus chrysippus (African Monarch), was investigated. The key step of the sequence involves asymmetric desymmetrization of the 1,3-propanediol 7 with lipase, in which high enantioselectivity was observed. Total synthesis afforded (S)-1 in 12 steps and 26% overall yield from readily available geraniol.     

Biosynthetic origin of the gem-methyls of geraniol

Degradation of geraniol (3,7-dimethylocta-trans-2,6-dien-1-ol) biosynthesized in Rosa dilecta has proved that C-10 is exclusively derived from C-2 of mevalonate. This verifies the generally accepted but hitherto unproven view of the origin of the gem-methyls in this compound and of the corresponding groups in other terpenoids.     

海南木莲叶挥发油化学成分研究

目的：分析海南木莲叶的挥发油成分。方法：采用水蒸气法提取挥发油,气相色谱-质谱-计算机联用技术分析。结果：共鉴定出49种化合物,占挥发油总量的99．99％,其中主要成分是橙花叔醇（16．44％）;3,7-二甲基-2,6-辛二烯-1-醇（5.27％）;3,7-二甲基1,6-辛二烯-3-醇（5．12％）;α-丁香烯（4．97％）和丁香烯（4．48％）。     

Repellency of essential oils and their components to the human body louse, Pediculus humanus humanus

Five essential oils and nine of their components were compared to diethyl toluamide (DEET) for their repellent activity against the human body louse, Pediculus humanus humanus. The absolute or intrinsic repellency of the compounds was tested by applying the repellent to corduroy patches and comparing them with untreated patches. It was found that the most effective repellents were DEET and citronella, whose activity lasted at least 29 days. The activity of rosemary lasted at least 18 days and that of eucalyptus more than 8 days. The repellent activity of the oil components such as citronellal and geraniol lasted more than 15 and 8 days, respectively. DEET remained effective at a dilution of 1:32, geraniol at 1:8, citronella at 1:4 and rosemary and citronellal at 1:1. The comparative or standard repellency of the candidate repellents was examined with the aid of a new screening technique using hairs treated with ammonium bicarbonate which is attractive to lice. Using this technique it could be shown that the repellent activity of citronella and geraniol lasted 2 days and that of rosemary and citronellal for only one day. DEET was active for less than one day. Serial dilutions of these substances also revealed that citronella was the most potent repellent for lice, followed by citronellal, rosemary, geraniol and DEET. The differences however, were not significant.     

Acaricidal effects of herb essential oils against Dermatophagoides farinae and D. pteronyssinus (Acari: Pyroglyphidae) and qualitative analysis of a herb Mentha pulegium(pennyroyal)

This experiment was undertaken to screen the acaricidal effects of herb essential oils (pennyroyal, ylang ylang, citronella, lemon grass, tea tree, and rosemary) at different doses (0.1, 0.05, 0.025, 0.0125, and 0.00625 microliter/cm(2)) and exposure times (5, 10, 20, 20, 30 and 60 min) on house dust mites Dermatophgoides farinae and D. pteronyssinus. The most effective acaricidal components of pennyroyal (Mentha pulegium) were analyzed using a gas chromatography-mass spectrometer (GC-MS). Of these essential oils, the most effective was pennyroyal, which is composed essentially of pulegone (> 99%), at a dose of 0.025 microliter/cm(2), which at an exposure time of 5 min killed more than 98% of house dust mites. In the pennyroyal fumigation test, the closed method was more effective than the open method and maximum acaricidal effect was 100% at 0.025 microliter/cm(2), 60 min. The results show that herb essential oils, in particular, pennyroyal was proved to have potent acaricidal activity.     

本姜子属及山胡椒属的平行演化

本文阐述樟科木姜子属及山胡椒属两者在形态、分布、起源及演化等方面有许多共同之处,不仅在属内具有平行演化的情况,而且各自平行演化成单花木姜子属 Dodecade－nia和单花山胡椒属Iteadaphne。同时两者又分别自4药室的拟擦术属Parasassafras和2药室的黄脉擦术属 sinosassafras演化而来。本文将单花木姜子亚属 Litsea subg．Uniflos Yang et P．H．Huang归人单花木姜子属,并把 Litsea monantha Yang et P．H．Hu－ang一种作为单花木姜子（原变种）Dodecadenia grandiflora Nees var．grandiflora的新异名,恢复了单花山胡椒属Iteadaphne Bl.,并将香面叶Lindera caudata（Nees）Hook·f．重新组合归入该属为Ⅰ．caudata（Nees）H．W．Li,comb．nov。此外,本文还发表了一个新属即黄脉擦木屑 Sinosassafras H．W．Li,gen．nov.,它具有2药室花药而不同于其平行演化的拟擦本属。     

Antifungal effects of herbal essential oils alone and in combination with ketoconazole against Trichophyton spp

AIMS: To determine the effects of herbal essential oils on Trichophyton spp. growth and to evaluate the effects of Pelargonium graveolens oil and its main components citronellol and geraniol combined with ketoconazole against Trichophyton spp. METHODS AND RESULTS: Growth inhibition of six Trichophyton spp. by herbal essential oils was accessed and the combined effects of P. graveolens oil and its main components citronellol and geraniol were evaluated using a checkerboard microtitre assay against T. schoenleinii, T. erinacei and T. soudanense. The essential oil fraction of P. graveolens and its main components, geraniol and citronellol, exhibited strong synergism with ketoconazole against T. schoenleinii and T. soudanense, with fractional inhibitory concentration (FIC) indices in the range of 0.18-0.38. CONCLUSIONS: The antifungal effects of ketoconazole against Trichophyton spp. are enhanced significantly by administering it in combination with the essential oil fraction of P. graveolens or its main components, because of strong synergism, especially against T. soudanense and T. schoenleinii. SIGNIFICANCE AND IMPACT OF THE STUDY: The combination of ketoconazole and the essential oil fraction from P. graveolens or its main components for treatment of infections caused by Trichophyton species may reduce the minimum effective dose of ketoconazole, and thus minimize the side-effects of ketoconazole.