Effects of enzyme treatment on volatile and non-volatile compounds in dried green tea leaves.

Green tea contains polyphenols, mainly four catechins, including (-)-epigallocatechin gallate, (-)-epicatechin gallate, (-)-epigallocatechin, and (-)-epicatechin. Enzyme tannase is known to hydrolyze gallated catechins into non-gallated catechins and gallic acid (GA). In this study, dried green tea leaves were treated with tannase to determine changes of volatile and non-volatile compounds by the hydrolysis. The results indicated that (-)-epigallocatechin, (-)-epicatechin, and GA increased, while (-)-epigallocatechin gallate and (-)-epicatechin gallate decreased after the treatment. The GA level increased in the treated samples, which increased titratable acidity significantly, while the pH became lower. Furthermore, the antioxidant activity of the tannase-treated tea leaves increased. The level of glycosidically bound aromas decreased with the concomitant increase of corresponding volatile compounds, while some alcohols derived from fatty acids decreased significantly after the treatment. These results suggest that tannase-treatment influences both volatile and non-volatile compounds in dried green tea leaves.

Synthesis of 3,5-Disubstituted Isoxazoles Containing Privileged Substructures with a Diverse Display of Polar Surface Area.

We designed and synthesized the molecular framework of 3,5-disubstituted isoxazoles containing privileged substructures with various substituents which uniquely display polar surface area in a diverse manner. A library of 3,5-disubstituted isoxazoles were systematically prepared via 1,3-dipolar cycloaddition of alkynes with nitrile oxides prepared by two complementary synthetic routes; method A utilized a halogenating agent with a base and method B utilized a hypervalent iodine reagent. Through the biological evaluation of corresponding isoxazoles via three independent phenotypic assays, the different pattern of biological activities was shown according to the type of privileged substructure and substituent. These results demonstrated the significance of molecular design via introducing privileged substructures and various substituents to make a diverse arrangement of polar surface area within a similar 3-dimensional molecular framework.

Larvicidal activity of naturally occurring naphthalenedione and its structurally related analogs against three mosquito species.

The objective of this study was to determine the larvicidal activity of an active compound isolated from Cercis chinensis heartwood and its structurally related analogs against 4th-stage Aedes aegypti, Culex pipiens pallens, and Ae. togoi. The larvicidal compound of C. chinensis was isolated with the use of various chromatographic techniques and identified as analogs of 1,4-naphthalenedione. Based on the median lethal concentration (LC(50)) values of commercially procured analogs against Ae. aegypti larvae, the most toxic analog was 2-bromo-1,4-naphthalenedione (1.19 µg/ml); followed by 5-hydroxy-1,4-naphthalenedione (1.72 µg/ml); 2-methyl-1,4-naphthalenedione (9.12 µg/ml); 2-hydroxy-1,4-naphthalenedione (10.76 µg/ml); and 2-methoxy-1,4-naphthalenedione (12.50 µg/ml). Similar results were observed against Cx. p. pallens and Ae. togoi larvae with 1,4-naphthalenedione analogs. These results also showed that 1,4-naphthalenedione analogs were less toxic than the organophosphate pirimiphos-methyl. Nonetheless, naturally occurring C. chinensis-derived materials and 1,4-naphthalenedione analogs have potential for development as mosquito larvicidal agents.

Evaluation of benzaldehyde derivatives from Morinda officinalis as anti-mite agents with dual function as acaricide and mite indicator.

Severe fever with thrombocytopenia syndrome (SFTS) is an emerging infectious disease caused by SFTS virus with 12-30% fatality rate. Despite severity of the disease, any medication or treatment for SFTS has not developed yet. One approach to prevent SFTS spreading is to control the arthropod vector carrying SFTS virus. We report that 2-methylbenzaldehyde analogues from M. officinalis have a dual function as acaricide against Dermatophagoides spp. and Haemaphysalis longicornis and indicator (color change) against Dermatophagoides spp. Based on the LD50 values, 2,4,5-trimethylbenzaldehyde (0.21, 0.19, and 0.68 µg/cm(3)) had the highest fumigant activity against D. farinae, D. pteronyssinus, and H. longicornis, followed by 2,3-dimethylbenzaldehyde (0.46, 0.44, and 0.79 µg/cm(3)), 2,4-dimethylbenzaldehyde (0.66, 0.59, and 0.95 µg/cm(3)), 2,5-dimethylbenzaldehyde (0.65, 0.68, and 0.88 µg/cm(3)), 2-methylbenzaldehyde (0.95, 0.87, and 1.28 µg/cm(3)), 3-methylbenzaldehyde (0.99, 0.93, and 1.38 µg/cm(3)), 4-methylbenzaldehyde (1.17, 1.15, and 3.67 µg/cm(3)), and M. officinalis oil (7.05, 7.00, and 19.70 µg/cm(3)). Furthermore, color alteration of Dermatophagoides spp. was shown to be induced, from colorless to dark brown, by the treatment of 2,3-dihydroxybenzaldehyde. These finding indicated that 2-methylbenzaldehyde analogues could be developed as functional agent associated with the arthropod vector of SFTS virus and allergen.

Acaricidal activities against house dust mites of spearmint oil and its constituents.

The aim of this study was to evaluate the acaricidal activities of spearmint oil and carvone derivatives against house dust mites using contact and fumigant toxicity bioassays to replace benzyl benzoate as a synthetic acaricide. Based on the LD50 values, the contact toxicity bioassay revealed that dihydrocarvone (0.95 and 0.88 µg/cm2) was 7.7 and 6.8 times more toxic than benzyl benzoate (7.33 and 6.01 µg/cm2) against Dermatophagoides farinae and Dermatophagoides pteronyssinus, respectively, followed by carvone (3.78 and 3.23 µg/cm2), spearmint oil (5.16 and 4.64 µg/cm2), carveol (6.00 and 5.80 µg/cm2), and dihydrocarveol (8.23 and 7.10 µg/cm2). Results of the fumigant toxicity bioassay showed that dihydrocarvone (2.73 and 2.16 µg/cm2) was approximately 4.0 and 4.8 times more effective than benzyl benzoate (11.00 and 10.27 µg/cm2), followed by carvone (6.63 and 5.78 µg/cm2), carveol (7.58 and 7.24 µg/cm2), spearmint oil (9.55 and 8.10 µg/cm2), and dihydrocarveol (9.79 and 8.14 µg/cm2). Taken together, spearmint oil and carvone derivatives are a likely viable alternative to synthetic acaricides for managing house dust mites.

Antimicrobial potentials of active component isolated from Citrullus colocynthis fruits and structure-activity relationships of its analogues against foodborne bacteria.

BACKGROUND: Synthetic preservatives have been consistently used to maintain the quality of food products. However, the degree of danger to human health cannot be ignored. In this study, the antimicrobial activities of Citrullus colocynthis fruits and 4-methylquinoline analogues were investigated to develop natural preservatives against foodborne bacteria. RESULTS: Antimicrobial activities of the methanol extract and five fractions derived from C. colocynthis fruits were evaluated against five foodborne bacteria. The chloroform fraction possessed strong activities against five foodborne bacteria. 4-Methylquinoline was isolated by chromatographic analyses. To establish the structure-activity relationships, the antimicrobial activities of 4-methylquinoline analogues (2-hydroxyquinoline, 4-hydroxyquinoline, 6-hydroxyquinoline, 2-methylquinoline, 6-methyquinoline, 8-methylquinoline and 2-methyl-8-hydroxyquinoline) were tested against food-borne bacteria. When employing the agar diffusion method, 2-methyl-8-hydroxyquinoline was found to have potent activities against the five foodborne bacteria. In terms of minimum bactericidal concentration or minimum inhibitory concentration, 2-methyl-8-hydroxyquinoline had significantly higher antimicrobial activity against the five foodborne bacteria. CONCLUSION: Citrullus colocynthis fruits and 4-methylquinoline analogues could be useful for the development of eco-friendly food supplemental agents and pharmaceuticals.

Acaricidal activities of ß-caryophyllene oxide and structural analogues derived from Psidium cattleianum oil against house dust mites.

BACKGROUND: This study was to evaluate the acaricidal activities of an active compound isolated from Psidium cattleianum and structural analogues against Dermatophagoides farinae and D. pteronyssinus. ß-Caryophyllene oxide was isolated using chromatographic techniques. RESULTS: Based on the 50% lethal concentration (LD50) values against D. farinae using the fumigant method, ß-caryophyllene oxide (1.36 µg cm(-2)) was ∼ 7.52 times more toxic than benzyl benzoate (10.23 µg cm(-2)), followed by α-caryophyllene (1.75 µg cm(-2)) and ß-caryophyllene (3.13 µg cm(-2)). Against D. pteronyssinus, ß-caryophyllene oxide (1.38 µg cm(-2)) was ∼ 7.22 times more toxic than benzyl benzoate (9.96 µg cm(-2)), followed by α-caryophyllene (1.71 µg cm(-2)) and ß-caryophyllene (3.58 µg cm(-2)). In the contact toxicity method against D. farinae, ß-caryophyllene oxide (0.44 µg cm(-2)) was ∼ 17.27 times more active than benzyl benzoate (7.60 µg cm(-2)), followed by α-caryophyllene (0.67 µg cm(-2)) and ß-caryophyllene (0.91 µg cm(-2)). Against D. pteronyssinus, ß-caryophyllene oxide (0.47 µg cm(-2)) was ∼ 13.06 times more effective than benzyl benzoate (6.14 µg cm(-2)), followed by α-caryophyllene (1.71 µg cm(-2)) and ß-caryophyllene (3.58 µg cm(-2)). CONCLUSION: ß-Caryophyllene oxide and structural analogues have potential for development as preventive agents for the control of house dust mites.

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/cm(2)) was 9.71 times more effective than benzyl benzoate (7.96 µg/cm(2)), followed by (1R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (1.03 µg/cm(2)), (1S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (1.58 µg/cm(2)), and (1R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one oxime (3.05 µg/cm(2)) 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.

Food protective effects of the active constituent isolated from Ostericum praeteritum against the stored food mite, Tyrophagus putrescentiae.

The acaricidal effects of the active constituent isolated from Ostericum praeteritum oil and its derivatives were compared with that of benzyl benzoate using fumigant and contact toxicity bioassays against Tyrophagus putrescentiae mites. The active compound of O. praeteritum was isolated by various chromatographic techniques and was identified as 3-methylphenol (C7H8O). On the basis of 50 % lethal dose values, 3-methylphenol (1.42 µg/cm(2)) was determined to be 9.18 times more effective than benzyl benzoate (13.04 µg/cm(2)), followed by 6-fluoro-3-methylphenol (2.18 µg/cm(2)), 4-isopropyl-3-methylphenol (2.53 µg/ cm(2)), and 6-chloro-3-methylphenol (4.03 µg/cm(2)), against Tyrophagus putrescentiae mites in the fumigant bioassay. In the contact toxicity bioassay, 3-methylphenol (1.03 µg/cm(2)) was the most-toxic compound against T. putrescentiae mites, followed by 6-fluoro-3-methylphenol (2.09 µg/cm(2)), 4-isopropyl-3-methylphenol (2.11 µg/cm(2)), 6-chloro-3-methylphenol (3.78 µg/cm(2)), and benzyl benzoate (10.33 µg/cm(2)). These results indicate that the introduction of chloro, isopropyl, and fluoro functional groups to the 3-methylphenol skeleton increased the acaricidal activity. Therefore, 3-methylphenol and its derivatives could potentially be used as natural acaricides against T. purescentiae.

Larvicidal activity of the active constituent isolated from Tabebuia avellanedae bark and structurally related derivatives against three mosquito species.

Mosquito larvicidal activities of active constituent isolated from Tabebuia avellanedae bark and its structurally related derivatives were examined against the fourth instar larvae of Aedes aegypti, Culex pipiens pallens, and Ochlerotatus togoi. The insecticidal constituent of T. avellanedae bark was isolated by chromatographic techniques and identified as 2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthalenedione. On the basis of the 50% lethal concentration (LC50) values against C. pipiens pallens larvae, the most toxic compound was 1,4-naphthalenedione (1.26 mg/L), followed by 1,2-naphthalenedione (1.43 mg/L), 1,4-naphthalenediol (3.20 mg/L), 2-chloro-3-pyrrolidino-1,4-naphthalenedione (5.11 mg/L), 2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthalenedione (8.30 mg/L), and 2-chloro-3-morpholino-1,4-naphthalenedione (12.98 mg/L). Similar results against A. aegypti and O. togoi larvae were observed for 2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthalenedione and its derivatives. According to the LC50 values against three mosquito species, these compounds were less toxic than pirimiphos-methyl. Nonetheless, naturally occurring T. avaellenedae bark-derived materials could be useful as a natural mosquito control agent.

Acaricidal potentials of active properties isolated from Cynanchum paniculatum and acaricidal changes by introducing functional radicals.

This study evaluated the acaricidal activities of acetophenone and its derivatives for their potentials as natural acaricides using an impregnated fumigant bioassay against Dermatophagoides spp. and Tyrophagus putrescentiae . On the basis of the LD50 values against D. farinae, 3'-methoxyacetophenone (0.41 µg/cm(2)) was 89.9 times more toxic than DEET (36.87 µg/cm(2)), followed by 4'-methoxyacetophenone (0.52 µg/cm(2)), 2'-methoxyacetophenone (0.75 µg/cm(2)), 2'-hydroxy-5'-methoxyacetophenone (1.03 µg/cm(2)), 2'-hydroxy-4'-methoxyacetophenone (1.29 µg/cm(2)), acetophenone (1.48 µg/cm(2)), 2'-hydroxyacetophenone (1.74 µg/cm(2)), 2',5'-dimethoxyacetophenone (1.87 µg/cm(2)), 2',4'-dimethoxyacetophenone (2.10 µg/cm(2)), and benzyl benzoate (9.92 µg/cm(2)). In regard to structure-activity relationships between acaricidal activity and functional radicals (hydroxyl and methoxy groups) on the acetophenone skeleton, a monomethoxy group (2'-, 3'-, and 4'-methoxyacetone) on the acetophenone skeleton was more toxic than were the other groups (2',4'- and 2',5'-dimethoxyacetophenone, 2'- and 4'-hydroxyacetophenone, 2'-hydroxy-4'-methoxyacetophenone, 2'-hydroxy-5'-methoxyacetophenone, and 4'-hydroxy-3'-methoxyacetophenone). These results indicated that acaricidal activity against three mite species changed with the introduction of functional radicals (hydroxyl and methoxy groups) onto the acetophenone skeleton.

Acaricidal toxicities of 1-hydroxynaphthalene from Scutellaria barbata and its derivatives against house dust and storage mites.

The essential oil of Scutellaria barbata was extracted using a steam distillation and then evaluated via fumigant and contact toxicity bioassays against Dermatophagoides farinae, Dermatophagoides pteronyssinus, and Tyrophagus putrescentiae. The acaricidal toxicities of 1-hydroxynaphthalene from S. barbata oil and its derivatives were determined and compared with those of benzyl benzoate. Based on the LD50 values of 1-hydroxynaphthalene derivatives against D. farinae, D. pteronyssinus, and T. putrescentiae, obtained using a fumigant toxicity bioassay, the acaricidal activity of 1-hydroxynaphthalene (2.11, 2.37, and 4.50 µg/cm2) was 4.76, 6.00, and 2.68 times higher than that of benzyl benzoate (10.05, 9.50, and 12.50 µg/cm2) in the corresponding order, which was followed by that of 2-hydroxynaphthalene (9.50, 9.00, and 11.50 µg/cm2). On the contact toxicity bioassay, the acaricidal activity of 1-hydroxynaphthalene (0.79, 0.92, and 2.50 µg/cm2) was 9.49, 6.52, and 3.76 times higher than that of benzyl benzoate (7.50, 6.00, and 9.41 µg/cm2), which was followed by that of 2-hydroxynaphthalene (4.21, 4.80, and 6.50 µg/cm2). In conclusion, our results indicate that S. barbata oil and 1-hydroxynaphthalene derivatives might be effective natural agents for the management of house dust and storage mites.

Effect of pedunculagin investigated by non-invasive evaluation on atopic-like dermatitis in NC/Nga mice.

BACKGROUND/PURPOSE: Atopic dermatitis (AD) is a chronic relapsing inflammatory skin disorder that is becoming increasingly prevalent. Experimental animal models have been an indispensable tool for studying its pathological mechanisms and for in vivo testing of novel therapeutic approaches. AD-like lesions can be induced experimentally in NC/Nga mice. Pedunculagin, an ellagitannin purified from the Manchurian alder, Alnus hirsuta var. microphylla, Betulaceae, is a novel immunomodulator. To evaluate the effect of pedunculagin for AD-like lesions in NC/Nga mice, using clinical and non-invasive methods. METHODS: AD-like lesions were induced in NC/Nga mice using 2,4,6-trinitrochlorobenzene (TNCB). A cream containing 0.1% or 0.5% pedunculagin was applied to the positive treatment group, and the base cream without pedunculagin was applied to the negative treatment group. The control group did not receive any kind of topical agents. We evaluated the therapeutic efficacy of pedunculagin for AD by statistical evaluation of the clinical severity score using non-invasive biomedical engineering tools before treatment, and 1 day, 3 days, 1 week, 2 weeks and 4 weeks afterwards. RESULTS: An AD-like skin rash was successfully induced using TNCB in NC/Nga mice. The group receiving higher concentrations of pedunculagin showed faster and greater improvement. CONCLUSION: Our results suggest that remedies made from natural materials like pedunculagin are now showing promise for medical applications, and many new studies are expected to explore this potential.

Acaricidal activity of triketone analogues derived from Leptospermum scoparium oil against house-dust and stored-food mites.

BACKGROUND: Various attempts to control the populations of house-dust and stored-food mites have been implemented using synthetic chemicals. Although effective, the repeated use of these chemicals has led to resistance owing to the mite's high reproductive potential and short life cycle. Therefore, this study aimed to develop natural acaricides using oils derived from Leptospermum scoparium JR & G Forst., which may affect the overall biological activity of a mite without adverse effects. Results were compared with those from using benzyl benzoate and N,N-diethyl-3-methylbenzamide (DEET). RESULTS: The LD(50) values of L. scoparium oil were 0.54, 0.67 and 1.12 microg cm(-2) against Dermatophagoides farinae (Hughes), D. pteronyssinus (Troussart) and Tyrophagus putrescentiae (Schrank) respectively. The active constituent isolated from L. scoparium was identified as leptospermone (6-isovaleryl-2,2,4,4-tetramethyl-1,3,5-cyclohexanetrione) by spectroscopic analysis. Based on the LD(50) values of leptospermone and its derivatives, the most toxic compound against D. farinae was leptospermone (0.07 microg cm(-2)), followed by 2,2,4,4,6,6-hexamethyl-1,3,5-cyclohexanetrione (1.21 microg cm(-2)), benzyl benzoate (10.03 microg cm(-2)) and DEET (37.12 microg cm(-2)). Furthermore, similar results were observed when the leptospermone and its derivatives were tested against D. pteronyssinus and T. putrescentiae. CONCLUSIONS: These results indicate that L. scoparium oil-derived materials, particularly leptospermone and 2,2,4,4,6,6-hexamethyl-1,3,5-cyclohexanetrione, have potential for development as new agents for the control of three species of mite.

Mite-control activities of active constituents isolated from Pelargonium graveolens against house dust mites.

The mite-control activities of materials obtained from Pelargonium graveolens oil against Dermatophagoides farinae and D. pteronyssinus were examined using an impregnated fabric disk bioassay and were compared with those shown by commercial benzyl benzoate and N,N-diethylm- toluamide (DEET). Purification of the biologically active constituents from P. graveolens oil was done by silica gel chromatography and high performance liquid chromatography. The structures of the active components were analyzed by EI/MS, (1)H-NMR, (13)C-NMR, (1)H-(13)C COSYNMR, and DEPT-NMR spectra, and were identified as geraniol (C(10)H(18)O, MW 154.25, trans-3,7-dimethyl-2,6- octadien-1-ol) and beta-citronellol (C(10)H(20)O, MW 156.27, 3,7-dimethyl-6-octen-1-ol). Based on the LD50 values, the most toxic compound was geraniol (0.26 microg/cm(2)), followed by beta-citronellol (0.28 microg/cm(2)), benzyl benzoate (10.03 microg/ cm(2)), and DEET (37.12 microg/cm(2)) against D. farinae. In the case of D. pteronyssinus, geraniol (0.28 microg/cm(2)) was the most toxic, followed by beta-citronellol (0.29 microg/cm(2)), benzyl benzoate (9.58 microg/cm(2)), and DEET (18.23 microg/cm(2)). These results suggest that D. farinae and D. pteronyssinus may be controlled more effectively by the application of geraniol and beta-citronellol than benzyl benzoate and DEET. Furthermore, geraniol and beta-citronellol isolated from P. graveolens could be useful for managing populations of D. farinae and D. pteronyssinus.