Antifungal Sesquiterpenoids from Michelia formosana Leaf Essential Oil against Wood-Rotting Fungi.

Michelia formosana (Kanehira) Masamune is a broad-leaved species widespread in East Asia; the wood extract and its constituents possess antifungal activity against wood-decay fungi. Antifungal activities of leaf essential oil and its constituents from M. formosana were investigated in the present study. Bioassay-guided isolation was applied to isolate the phytochemicals from leaf essential oil. 1D and 2D NMR, FTIR, and MS spectroscopic analyses were applied to elucidate the chemical structures of isolated compounds. Leaf essential oil displayed antifungal activity against wood decay fungi and was further separated into 11 fractions by column chromatography. Four sesquiterpenoids were isolated and identified from the active fractions of leaf essential oil through bioassay-guided isolation. Among these sesquiterpenoids, guaiol, bulnesol, and ß-elemol have higher antifungal activity against brown-rot fungus Laetiporus sulphureus and white-rot fungus Lenzites betulina. Leaf essential oil and active compounds showed better antifungal activity against L. sulphureus than against L. betulina. The molecular structure of active sesquiterpenoids all contain the hydroxyisopropyl group. Antifungal sesquiterpenoids from M. formosana leaf essential oil show potential as natural fungicides for decay control of lignocellulosic materials.

Thermal Degradation of Linalool-Chemotype Cinnamomum osmophloeum Leaf Essential Oil and Its Stabilization by Microencapsulation with ß-Cyclodextrin.

The thermal degradation of linalool-chemotype Cinnamomum osmophloeum leaf essential oil and the stability effect of microencapsulation of leaf essential oil with ß-cyclodextrin were studied. After thermal degradation of linalool-chemotype leaf essential oil, degraded compounds including ß-myrcene, cis-ocimene and trans-ocimene, were formed through the dehydroxylation of linalool; and ene cyclization also occurs to linalool and its dehydroxylated products to form the compounds such as limonene, terpinolene and α-terpinene. The optimal microencapsulation conditions of leaf essential oil microcapsules were at a leaf essential oil to the ß-cyclodextrin ratio of 15:85 and with a solvent ratio (ethanol to water) of 1:5. The maximum yield of leaf essential oil microencapsulated with ß-cyclodextrin was 96.5%. According to results from the accelerated dry-heat aging test, ß-cyclodextrin was fairly stable at 105 °C, and microencapsulation with ß-cyclodextrin can efficiently slow down the emission of linalool-chemotype C. osmophloeum leaf essential oil.

Evaluation of Motor Coordination and Antidepressant Activities of Cinnamomum osmophloeum ct. Linalool Leaf Oil in Rodent Model.

Cinnamomum plants (Lauraceae) are a woody species native to South and Southeast Asia forests, and are widely used as food flavors and traditional medicines. This study aims to evaluate the chemical constituents of Cinnamomum osmophloeum ct. linalool leaf oil, and its antidepressant and motor coordination activities and the other behavioral evaluations in a rodent animal model. The major component of leaf oil is linalool, confirmed by GC-MS analysis. Leaf oil would not induce the extra body weight gain compared to the control mice at the examined doses after 6 weeks of oral administration. The present results provide the first evidence for motor coordination and antidepressant effects present in leaf oil. According to hypnotic, locomotor behavioral, and motor coordination evaluations, leaf oil would not cause side effects, including weight gain, drowsiness and a diminishment in the motor functions, at the examined doses. In summary, these results revealed C. osmophloeum ct. linalool leaf essential oil is of high potential as a therapeutic supplement for minor/medium depressive syndromes.

Xanthine Oxidase Inhibitory Activity and Thermostability of Cinnamaldehyde-Chemotype Leaf Oil of Cinnamomum osmophloeum Microencapsulated with ß-Cyclodextrin.

The xanthine oxidase inhibitory activity and thermostability of Cinnamomum osmophloeum leaf oil microencapsulated with ß-cyclodextrin were evaluated in this study. The yield of leaf oil microcapsules was 86.3% using the optimal reaction conditions at the leaf oil to ß-cyclodextrin ratio of 15:85 and ethanol to water ratio ranging from 1:3 to 1:5. Based on the FTIR analysis, the characteristic absorption bands of major constituent, trans-cinnamaldehyde, were confirmed in the spectra of leaf oil microcapsules. According to the dry-heat aging test, ß-cyclodextrin was thermostable under the high temperature conditions, and it was beneficial to reduce the emission of C. osmophloeum leaf oil. Leaf oil microcapsules exhibited high xanthine oxidase inhibitory activity, with an IC50 value of 83.3 µg/mL. It is concluded that the lifetime of C. osmophloeum leaf oil can be effectively improved by microencapsulation, and leaf oil microcapsules possess superior xanthine oxidase inhibitory activity.

Correction: Chan, Y.-Y., et al. The Constituents of Michelia compressa var. formosana and Their Bioactivities. Int. J. Mol. Sci. 2014, 15, 10926-10935.

The authors wish to make two changes to their published paper [1]. [...].

Effect of maternal use of chewing gums containing xylitol on transmission of mutans streptococci in children: a meta-analysis of randomized controlled trials.

BACKGROUND: Mutans streptococci (MS) are the major causative bacteria involved in human dental decay. Habitual consumption of xylitol has been proved to reduce MS levels in saliva and plaque. AIM: To evaluate the effect of the maternal use of xylitol gum on MS reduction in infants. DESIGN: A structured literature review and meta-analysis. A random effects model was used to assess the relative risks of the incidence of MS in the saliva or plaque of children who were 6, 9, 12, 18, and 24 months old. RESULTS: We reviewed 11 RCTs derived from 5 research teams that included 601 mothers. Our results indicated that the incidence of MS in the saliva or plaque of the infants was significantly reduced in the xylitol group (risk ratio: 0.54; 95% confidence interval: 0.39-0.73, at 12-18 months) and (risk ratio: 0.56; 95% confidence interval: 0.40-0.79, at 36 months) compared with the control groups. The long-term effect of maternal xylitol gum exposure on their children's dental caries was controversial. CONCLUSION: Habitual xylitol consumption by mothers with high MS levels was associated with a significant reduction in the mother-child transmission of salivary MS.

The constituents of Michelia compressa var. formosana and their bioactivities.

Phytochemical investigation of the heartwood of Michelia compressa afforded forty-four compounds, which were identified by comparison of experimental and literature analytical and spectroscopic data. Some compounds were evaluated for their anti-inflammatory and anticancer bioactivities. The result showed that soemerine (1) and cyathisterol (2) exhibited significant nitric oxide (NO) inhibition, with IC50 values of 8.5±0.3 and 9.6±0.5 µg/mL, respectively. In addition, liriodenine (3) and oliveroline (4) exhibited cytotoxicity to human nasopharyngeal carcinoma (NPC-TW01), non-small cell lung carcinoma (NCI-H226), T cell leukemia (Jurkat), renal carcinoma (A498), lung carcinoma (A549) and fibrosarcoma (HT1080) cell lines with IC50 values in the range of 15.7-3.68 µM.

In Vitro and In Vivo Antimelanogenesis Effects of Leaf Essential Oil from Agathis dammara.

Agathis species are widely distributed around Southeast Asia, Australasia, South Pacific islands, and etc. Traditionally, Agathis species have been used as the folk medicines, the common ethnopharmacological uses of Agathis genus are the treatments of headache and myalgia. This study aims to investigate the chemical composition of Agathis dammara (Lamb.) Rich. leaf essential oil and to explore its antimelanogenesis effect. The chemical constituents of leaf essential oil are analyzed using gas chromatography-mass spectrometry (GC-MS), the major constituents of leaf essential oil are sesquiterpenoids. The major constituents are δ-cadinene (16.12%), followed by γ-gurjunene (15.57%), 16-kaurene (12.43%), ß-caryophyllene (8.58%), germacrene D (8.53%), and γ-cadinene (5.33%). As for the in vitro antityrosinase activity, leaf essential oil inhibit the tyrosinase activity of mushroom when the substrate is 3,4-dihydroxyphenylalanine (L-DOPA). Leaf essential oil prevents tyrosinase from acting as diphenolase and catalyzing L-DOPA to dopaquinone, and converting into dark melanin pigments. A. dammara leaf essential oil also exhibits the in vivo antimelanogenesis effect, leaf essential oil reduces 43.48% of melanin formation in zebrafish embryos at the concentration of 50 µg/mL. Results reveal A. dammara leaf essential oil has the potential for developing the skin whitening drug and depigmentation ingredient for hyperpigmentary disorders.

Cytotoxicity and Apoptosis Induction of 6,7-Dehydroroyleanone from Taiwania cryptomerioides Bark Essential Oil in Hepatocellular Carcinoma Cells.

The objective of the present study is to evaluate the cytotoxicity of Taiwania cryptomerioides essential oil and its phytochemical on the Hep G2 cell line (human hepatocellular carcinoma). Bark essential oil has significant cytotoxicity to Hep G2 cells, and S3 fraction is the most active fraction in cytotoxicity to Hep G2 cells among the six fractions. The diterpenoid quinone, 6,7-dehydroroyleanone, was isolated from the active S3 fraction by bioassay-guided isolation. 6,7-Dehydroroyleanone exhibited significant cytotoxicity in Hep G2 cells, and the efficacy of 6,7-dehydroroyleanone was better than the positive control, etoposide. Apoptosis analysis of Hep G2 cells with different treatments was characterized via flow cytometry to confirm the cell death situation. Etoposide and 6,7-dehydroroyleanone could induce the apoptosis in Hep G2 cells using flow cytometric assay. Results revealed 6,7-dehydroroyleanone from T. cryptomerioides bark essential oil can be a potential phytochemical to develop the anticancer chemotherapeutic agent for the treatment of the human hepatocellular carcinoma.

Xanthine Oxidase Inhibitory Activity and Chemical Composition of Pistacia chinensis Leaf Essential Oil.

Gout is a common metabolic disease caused by abnormal purine metabolism that promotes the formation and deposition of monosodium urate crystals within joints that causes acute arthritis and can seriously affect the daily life of patients. Pistacia chinensis is one of the traditional medicinal plants of the Anacardiaceae family, and there have been many studies on its biological activity, including anti-inflammatory, antidepressant, antibacterial, antioxidant, and hypoglycemic activities. The aim of this study was to evaluate the antigout effect of P. chinensis leaf essential oil and its constituents through xanthine oxidase inhibition. Leaf essential oil showed good xanthine oxidase inhibitory activity for both substrates, hypoxanthine and xanthine. Six fractions were obtained from open column chromatography, and fraction E1 exhibited the best activity. The constituents of leaf essential oil and fraction E1 were analyzed by GC-MS. The main constituents of both leaf essential oil and fraction E1 were limonene and 3-carene; limonene showed a higher inhibitory effect on xanthine oxidase. Based on the enzyme kinetic investigation, limonene was the mixed-type inhibitor against xanthine oxidase. The results revealed that Pistacia chinensis leaf essential oil and limonene have the potential to act as natural remedies for the treatment of gout.

Investigation of optimal conditions needed for the production of indigo and subsequent dyeing using CO2/O2 sensors and a cellphone camera.

An investigation of the process involved in the production of and dyeing with indigo based on a CO2/O2 sensor device and a cellphone-camera is reported. The former involves transforming indican to indigo, and the latter the process by which indigo and indigo-white are produced. During the process of indigo production, a clear and positive correlation can be observed between the concentration of gas levels (either the production of CO2 or the consumption of O2) and the final yield. The authors found that for the first time that the change in the concentration levels of CO2/O2 can be used as important parameters for indigo dyeing. The optimal time required to produce indigo can be decided by the change of CO2/O2 concentration level. It is no long should depending on the experience of a craftsperson. Furthermore, the optimal time needed to produce indigo also can be decided by the concentration levels of glucose. The color analysis of indigo dyeing can be performed by using a camera and by calculating the RGB and HSV (hue, saturation, value) values.

Antimelanogenesis Effects of Leaf Extract and Phytochemicals from Ceylon Olive (Elaeocarpus serratus) in Zebrafish Model.

The melanogenesis inhibition effect in zebrafish (Danio rerio) and antityrosinase activity of the ethanolic extract and its phytochemicals from Ceylon olive (Elaeocarpus serratus Linn.) leaves were investigated in this study. Among the leaf extract and four soluble fractions, the ethyl acetate soluble fraction exhibits the best antityrosinase and antimelanogenesis activities. One phenolic acid, gallic acid, and two flavonoids, myricetin and mearnsetin, are isolated from the active subfractions through the bioassay-guided isolation; their structures are elucidated based on the 1D and 2D NMR, FTIR, UV, and MS spectroscopic analyses. These compounds have significant antityrosinase activity whether using l-tyrosine or l-DOPA as the substrate; mearnsetin shows the optimal activity. In the enzyme kinetic investigation, both gallic acid and mearnsetin are the competitive-type inhibitors against mushroom tyrosinase, and myricetin acts as a mixed-type tyrosinase inhibitor. Leaf extract and an ethyl acetate soluble fraction show effective performance in the inhibition of melanin formation in zebrafish embryos. Mearnsetin also possesses a promising antimelanogenesis effect, which is superior to the positive control, arbutin. Results reveal that the Ceylon olive leaf extract and its phytochemicals, especially mearnsetin, have the potential to be used as antimelanogenesis and skin-whitening ingredients.

Methylglyoxal and D-lactate in cisplatin-induced acute kidney injury: Investigation of the potential mechanism via fluorogenic derivatization liquid chromatography-tandem mass spectrometry (FD-LC-MS/MS) proteomic analysis.

Nephrotoxicity severely limits the chemotherapeutic efficacy of cisplatin (CDDP). Oxidative stress is associated with CDDP-induced acute kidney injury (AKI). Methylglyoxal (MG) forms advanced glycation end products that elevate oxidative stress. We aimed to explore the role of MG and its metabolite D-lactate and identify the proteins involved in CDDP-induced AKI. Six-week-old female BALB/c mice were intraperitoneally administered CDDP (5 mg/kg/day) for 3 or 5 days. Blood urea nitrogen (42.6 ± 7.4 vs. 18.3 ± 2.5; p < 0.05) and urinary N-acetyl-ß-D-glucosaminide (NAG; 4.89 ± 0.61 vs. 2.43 ± 0.31 U/L; p < 0.05) were significantly elevated in the CDDP 5-day group compared to control mice. Histological analysis confirmed AKI was successfully induced. Confocal microscopy revealed TNF-α was significantly increased in the CDDP 5-day group. Fluorogenic derivatized liquid chromatography-tandem mass spectrometry (FD-LC-MS/MS) showed the kidney MG (36.25 ± 1.68 vs. 18.95 ± 2.24 mg/g protein, p < 0.05) and D-lactate (1.78 ± 0.29 vs. 1.12 ± 0.06 mol/g protein, p < 0.05) contents were significantly higher in the CDDP 5-day group than control group. FD-LC-MS/MS proteomics identified 33 and nine altered peaks in the CDDP 3-day group and CDDP 5-day group (vs. control group); of the 35 proteins identified using the MOSCOT database, 11 were antioxidant-related. Western blotting confirmed that superoxide dismutase 1 (SOD-1) and parkinson disease protein 7 (DJ-1) are upregulated and may participate with MG in CDDP-induced AKI. This study demonstrates TNF-α, MG, SOD-1 and DJ-1 play crucial roles in CDDP-induced AKI.

Methyl-CpG-binding PCR of bloodspots for confirmation of fragile X syndrome in males.

This study demonstrates that methyl-CpG-binding PCR (MB-PCR) is a rapid and simple method for detecting fragile X syndrome (FXS) in males, which is performed by verifying the methylation status of the FMR1 promoter in bloodspots. Proteins containing methyl-CpG-binding (MB) domains can be freeze-stored and used as stocks, and the entire test requires only a few hours. The minimum amount of DNA required for the test is 0.5 ng. At this amount, detection sensitivity is not hampered, even mixing with excess unmethylated alleles up to 320 folds. We examined bloodspots from 100 males, including 24 with FXS, in a blinded manner. The results revealed that the ability of MB-PCR to detect FMR1 promoter methylation was the same as that of Southern blot hybridization. Since individuals with 2 or more X chromosomes generally have methylated FMR1 alleles, MB-PCR cannot be used to detect FXS in females.

Insecticidal activities of leaf and twig essential oils from Clausena excavata against Aedes aegypti and Aedes albopictus larvae.

BACKGROUND: The current study investigates, for the first time, the mosquito larvicidal activities of leaf and twig essential oils from Clausena excavata Burm. f. and their individual constituents against Aedes aegypti L. and Aedes albopictus Skuse larvae. The yields of essential oils obtained from hydrodistillation were compared, and their constituents were determined by GC-MS analyses. RESULTS: The LC(50) values of leaf and twig essential oils against fourth-instar larvae of Ae. aegypti and Ae. albopictus were 37.1-40.1 microg mL(-1) and 41.1-41.2 microg mL(-1) respectively. This study demonstrated that C. excavata leaf and twig essential oils possess mosquito larvicidal activity, inhibiting the growth of mosquito larvae for both species at a low concentration. In addition, results of larvicidal assays showed that the effective constituents in leaf and twig essential oils were limonene, gamma-terpinene, terpinolene, beta-myrcene, 3-carene and p-cymene. The LC(50) values of these constituents against both mosquito larvae were below 50 microg mL(-1). Among these effective constituents, limonene had the best mosquito larvicidal activity, with LC(50) of 19.4 microg mL(-1) and 15.0 microg mL(-1) against Ae. aegypti and Ae. albopictus larvae respectively. CONCLUSION: The findings suggested that the essential oils from Clausena excavata leaf and twig and their effective constituents may be explored as a potential natural larvicide.

Characterizing the conservation effect of clear coatings on photodegradation of wood.

Photodiscoloration of clear-coated wood may be caused by the yellowing of both clear coating film and underlying wood, or either of them. Wood specimens covered with two types of free polyurethane films with/without light stabilizer were used to simulate the photodiscoloration of clear-coated wood. Percent UV transmission of aromatic polyurethane (PU) films decreased after irradiation, whereas aliphatic polyurethane (PUA) films significantly increased with irradiation time resulting in further photoyellowing of wood beneath the PUA film. A light reflection model was used to elucidate discoloration caused separately by the clear coating film and the underlying wood. After 24 days of light irradiation, clear coating and the underlying wood contributed respectively, 40.70% and 59.30% discoloration of PU-coated specimens, and the corresponding values for PUA-coated specimens were 5.15% and 94.85%. PU film with light stabilizer reduced lignin degradation and generation of carbonyl derivatives in the underlying wood.

Antifungal properties of ethanolic extract and its active compounds from Calocedrus macrolepis var. formosana (Florin) heartwood.

The ethanolic extract of Calocedrus macrolepis var. formosana heartwood was screened for antifungal compounds by agar dilution assay and liquid chromatography. Two compounds, beta-thujaplicin and gamma-thujaplicin, responsible for the antifungal property of C. macrolepis var. formosana heartwood were isolated by high performance liquid chromatography (HPLC), and identified by 1H NMR and 13C NMR. The antifungal activities of these two compounds were further evaluated against total 15 fungi, including wood decay fungi, tree pathogenic fungi and molds. The hexane soluble fraction showed the strongest antifungal activities among all fractions. beta-Thujaplicin and gamma-thujaplicin exhibited not only very strong antifungal activity, but also broad antifungal spectrum. The MIC values of beta-thujaplicin and gamma-thujaplicin were in the range of 5.0-50.0 microg/ml. In addition, scanning electron microscopy (SEM) was carried out to study the structural change of fungal hyphae induced by beta-thujaplicin. Strong cell wall shrinkage indicated the fungicidal effect could be attributed to the combined actions of metal chelating and cytoplasm leakage. It also suggests that the role of metal chelating is indispensable in the design of environmental-friendly fungicides.

Antifungal activity of essential oil and its constituents from Calocedrus macrolepis var. formosana Florin leaf against plant pathogenic fungi.

Resistance to conventional fungicides causes the poor disease control of agriculture. Natural products from plants have great potential as novel fungicide sources for controlling pathogenic fungi. In this study antipathogenic activity of the leaf essential oil and its constituents from Calocedrus macrolepis var. formosana Florin were evaluated in vitro against six plant pathogenic fungi. Chemical analysis of leaf oil by GC/MS allowed identification of alpha-pinene (44.2%), limonene (21.6%), beta-myrcene (8.9%), beta-caryophyllene (8.2%), caryophyllene oxide (2.4%), alpha-cadinol (1.6%), beta-pinene (1.2%), and T-muurolol (1.1%) as main components. Sesquiterpenoid components of the oil were more effective than monoterpenoid components of the oil. In particular, T-muurolol and alpha-cadinol strongly inhibited the growth of Rhizoctonia solani and Fusarium oxysporum, with the IC(50) values < 50 microg ml(-1). These compounds also efficiently inhibited the mycelial growths of Colletotrichum gloeosporioides, P. funerea, Ganoderma australe and F. solani. These results showed that T-muurolol and alpha-cadinol possess antifungal activities against a broad spectrum of tested plant pathogenic fungi and could be used as potential antifungal agents for the control of fungal diseases in plants.

Evaluation of antifungal properties of octyl gallate and its synergy with cinnamaldehyde.

The objective of this study was to investigate the possibility of using octyl gallate alone or with organic biocides as a preservative against wood decay fungi. Antifungal activities of three antioxidants, propyl gallate, octyl gallate and butylated hydroxyltoluene (BHT) were tested against four wood decay fungi, Lenzites betulina, Trametes versicolor, Gloeophyllum trabeum and Laetiporus sulphureus. Octyl gallate was found to be the only active compound with IC50 values of 0.47, 0.16, 0.24 and 0.04 mM against L. betulina, T. versicolor, G. trabeum and L. sulphureus, respectively. A synergistic effect was also found when octyl gallate was combined with cinnamaldehyde. Results obtained herein demonstrated that octyl gallate by itself exhibited an excellent antifungal property and enhanced protection was further observed by combining it with cinnamaldehyde.

Anti-termitic activities of essential oils from coniferous trees against Coptotermes formosanus.

In this study, the anti-termitic activities of 11 essential oils from three species of coniferous tree against Coptotermes formosanus Shiraki were investigated using direct contact application. Results demonstrated that at the dosage of 10 mg/g, the heartwood and sapwood essential oils of Calocedrus macrolepis var. formosana and Cryptomeria japonica and the leaf essential oil of Chamaecyparis obtusa var. formosana had 100% mortality after 5 d of test. Among the tested essential oils, the heartwood essential oil of C. macrolepis var. formosana killed all termites after 1 d of test, with an LC(50) value of 2.6 mg/g, exhibiting the strongest termiticidal property. The termiticidal effect of heartwood essential oil was due to its toxicity and its repellent action.