Shang-Tzen Chang

ANTIBACTERIAL ACTIVITY OF LEAF ESSENTIAL OILS AND THEIR CONSTITUENTS FROM CINNAMOMUM OSMOPHLOEUM

The antibacterial activities of the essential oils from leaves of two Cinnamomum osmophloeum clones (A and B) and their chemical constituents were investigated in this study. The nine strains of bacteria, including Escherichia coli, Pseudomonas aeruginosa, Enterococcus faecalis, Staphylococcus aureus, Staphylococcus epidermidis, methicillin-resistant Staphylococcus aureus (MRSA), Klebsiella pneumoniae, Salmonella sp., and Vibrio parahemolyticus, were used in the antibacterial tests. Results from the antibacterial tests demonstrated that the indigenous cinnamon B leaf essential oils had an excellent inhibitory effect. The MICs (minimum inhibitory concentrations) of the B leaf oil were 500 microg/ml against both K. pneumoniae and Salmonella sp. and 250 microg/ml against the other seven strains of bacteria. Cinnamaldehyde possessed the strongest antibacterial activity compared to the other constituents of the essential oils. The MICs of cinnamaldehyde against the E. coli, P. aeruginosa, E. faecalis, S. aureus, S. epidermidis, MRSA, K. pneumoniae, Salmonella sp., and V. parahemolyticus were 500, 1000, 250, 250, 250, 250, 1000, 500, and 250 microg/ml, respectively. These results suggest that C. osmophloeum leaf essential oil and cinnamaldehyde are beneficial to human health, having the potential to be used for medical purposes and to be utilized as anti-bacterial additives in making paper products.

Chemical compositions and larvicidal activities of leaf essential oils from two eucalyptus species.

In the current study, the mosquito larvicidal activity of leaf essential oils and their constituents from two eucalyptus species (Eucalyptus camaldulensis and Eucalyptus urophylla) against two mosquito species, Aedes aegypti and Aedes albopictus, was investigated. In addition, the chemical compositions of the leaf essential oils were analyzed using gas chromatography-mass spectrometry. Results from the larvicidal tests revealed that essential oil from the leaves of E. camaldulensis had an excellent inhibitory effect against both A. aegypti and A. albopictus larvae. The 12 pure constituents extracted from the two eucalyptus leaf essential oils were also tested individually against two mosquito larvae. Among the six effective constituents, alpha-terpinene exhibits the best larvicidal effect against both A. aegypti and A. albopictus larvae. Results of this study show that the leaf essential oil of E. camaldulensis and its effective constituents might be considered as a potent source for the production of fine natural larvicides.

Bioactivity of selected plant essential oils against the yellow fever mosquito Aedes aegypti larvae.

The bioactivity of 14 essential oils from five plants has been studied using the brine shrimp lethality test and the Aedes aegypti larvicidal assay. All essential oils screened had LC50 values smaller than 200 microg/ml, showing significant lethality against brine shrimp. In addition, nine of the 14 essential oils tested showed toxicity against the fourth-instar A. aegypti larvae in 24 h (LC50<100 microg/ml). Of these, the leaf and bark essential oils of Cryptomeria japonica demonstrated high larvicidal activity, the most active being the leaf essential oil of C. japonica, with a LC50=37.6 microg/ml (LC90=71.9 microg/ml), followed by the bark essential oil of C. japonica also showing high activity against A. aegypti larvae, with a LC50=48.1 microg/ml (LC90=130.3 microg/ml). The results obtained from this study suggest that the leaf and bark essential oils of C. japonica are promising as larvicides against A. aegypti larvae and could be useful in the search for new natural larvicidal compounds.

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.

Comparisons of the photostability of esterified wood

Abstract The light stability of wood panel treated with acetic anhydride, succinic anhydride, maleic anhydride, and phthalic anhydride was compared. Results from the solid state CP/MAS 13 C NMR analyses revealed that the esterification of holocelluloses occurred mainly at the C-6 position in the amorphous cellulose component. After lightfastness testing, the change in the color of wood treated with phthalic anhydride was greater than that subject to the other treatments. The color difference and yellowness index of acetylated wood after irradiation were significantly less than controls, indicating that acetylation inhibited the photoyellowing of wood. In addition, results obtained from diffuse reflectance UV-VIS spectral analyses clearly demonstrated that the amount of chromophores generated in wood treated with phthalic anhydride was more than that of the untreated control after photodegradation, and that the amount of chromophores on the irradiated acetylated wood surfaces was much less than that of the others. Acetylation reduced the formation of colored derivatives on the wood surfaces and consequently inhibited the photodiscoloration of wood.

Variations in insecticidal activity and chemical compositions of leaf essential oils from Cryptomeria japonica at different ages

The larvicidal effects of the essential oils extracted from the leaves of Cryptomeria japonica at different ages (58, 42, and 26 years old) against 2 mosquito species, Aedes aegypti and Aedes albopictus, were studied. The analysis of major constituents of these essential oils was also investigated. Results obtained from the larvicidal tests, using essential oil from the leaves of 58-year-old C. japonica was found to be most effective against both A. aegypti and A. albopictus larvae, indicating tree age has significant influence on mosquito larvicidal activity. In addition, the eleven pure constituents from C. japonica leaf essential oil were also tested individually against the two mosquito larvae. Among them, alpha-terpinene, gamma-terpinene, p-cymene, 3-carene, terpinolene, and beta-myrcene shows strong larvicidal effect against the two mosquito larvae. Among these pure constituents, 3-carene exhibits the best larvicidal effect against A. aegypti and terpinolene shows an excellent inhibitory action against A. albopictus larvae. The results of this study show that the leaf essential oil and its effective constituents might be considered as a potent source for the production of fine natural larvicides.

Comparison of the antifungal activity of cadinane skeletal sesquiterpenoids from Taiwania (Taiwania cryptomerioides Hayata) heartwood.

Summary The antifungal activity of cadinane skeletal sesquiterpenoids from Taiwania (Taiwania cryptomerioides Hayata) heartwood is demonstrated. Using spectral analyses, the absolute structures of three main cadinanes, T-cadinol, T-muurolol, and α-cadinol, all isolated from Taiwania with HPLC, were identified. The amount of these cadinanes was also quantified using GC. The results showed that the total amount of cadinanes extracted from heartwood with n-C6H14 was 6.49 mg per kg of wood. This was much more than the essential oils collected by water distillation from leaves (0.04 mg/kg), sapwood (0.36 mg/kg), or heartwood (1.77 mg/kg). Moreover, results obtained from the antifungal assays demonstrated that αcadinol exhibited the highest antifungal index for both Coriolus versicolor and Laetiporus sulphureus, followed by T-cadinol and T-muurolol. As a matter of fact, α-cadinol completely inhibited the growth of C. versicolor and L. sulphureus at the level as low as 100 ppm. Further comparison of the molecular configuration of these cadinanes reveals that cadinane skeletal sesquiterpenoids with an equatorial hydroxyl group at C-9 and a trans configuration at the ring junction, such as the case for α-cadinol, exhibited the strongest antifungal activity.

Antitermitic and antifungal activities of essential oil of Calocedrus formosana leaf and its composition.

Calocedrus formosana Florin (Cupressaceae) is an endemic tree species in Taiwan; its timber is recognized for natural decay resistance. To examine the antitermitic and antifungal activities of leaf essential oil and its main constituents, C. formosana leaves were extracted and the essential oils analyzed by GC-MS. Bioactivity tests against the termite Coptotermes formosanus demonstrate that the LC50 value of leaf essential oil is 27.6 mg/g. Furthermore, exposure to T-muurolol caused 100% mortality at a dosage of 5 mg/g after 14 d. Leaf oil constituents displayed activity against four fungi, Lenzites betulina, Pycnoporus coccineus, Trametes versicolor, and Laetiporus sulphureus. Two compounds, α-cadinol and T-muurolol, exhibited the strongest antifungal activity. The LC50 values of α-cadinol against L. sulphureus, L. betulina, and T. versicolor are 9.9, 28.6, and 30.4 μ g/ml, respectively.

Insecticidal activities of leaf essential oils from Cinnamomum osmophloeum against three mosquito species.

The larvicidal activities of leaf essential oils and their constituents from six chemotypes of indigenous cinnamon (Cinnamomum osmophloeum Kaneh.) trees were evaluated against three mosquito species. Results of larvicidal tests demonstrated that the leaf essential oils of cinnamaldehyde type and cinnamaldehyde/cinnamyl acetate type had an excellent inhibitory effect against Aedes albopictus larvae, and their LC(50) values in 24h were 40.8 microg/ml (LC(90)=81.7 microg/ml) and 46.5 microg/ml (LC(90)=83.3 microg/ml), respectively. Results of the 24-h mosquito larvicidal assays also showed that the effective constituents in leaf essential oils were trans-cinnamaldehyde and benzaldehyde and that the LC(50) values of these constituents against A. albopictus larvae were below 50 mug/ml. In addition, cinnamaldehyde type leaf essential oil and trans-cinnamaldehyde have also exhibited great larvicidal performance against Culex quinquefasciatus and Armigeres subalbatus larvae. Comparisons of mosquito larvicidal activity of trans-cinnamaldehyde congeners revealed that alpha-methyl cinnamaldehyde, benzaldehyde, and trans-cinnamaldehyde exhibited strong mosquito larvicidal activity.

Online RP-HPLC-DPPH screening method for detection of radical-scavenging phytochemicals from flowers of Acacia confusa.

Acacia confusa is traditionally used as a medicinal plant in Taiwan. In this study, phytochemicals and antioxidant activities of extracts from flowers of A. confusa were investigated for the first time. In addition, a rapid screening method, online RP-HPLC-DPPH system, for individual antioxidants in complex matrices was developed. Accordingly, six antioxidants including gallic acid ( 1), myricetin 3-rhamnoside ( 2), quercetin 3-rhamnoside ( 3), kaempferol 3-rhamnoside ( 4), europetin 3-rhamnoside ( 5), and rhamnetin 3-rhamnoside ( 6) were detected using the developed screening method. Of these, compounds 2, 3, and 5 were found to be major bioactive phytochemicals, and their contents were determined as 11.3, 6.7, and 8.7 mg/g of crude extract, respectively. By comparison with quercetin, a well-known antioxidant, these compounds had the order of compound 2 > compound 5 > quercetin > compound 3 for DPPH radical-scavenging activity. Their IC 50 values were 3.0, 3.2, 4.5, and 7.4 microM, respectively. Moreover, the same order was observed for superoxide radical-scavenging activity, and their IC50 values were 2.6, 2.7, 4.3, and 5.3 microM, respectively. However, for lipid peroxidation, quercetin, an aglycon, showed the best inhibitory activity. The IC50 values of quercetin, compound 2, compound 5, and compound 3 were 46.7, 88.5, 90.7, and 124.6 microM, respectively. These results indicated that a rhamnoside at the C3 position of flavonoids had a negative effect on radical-scavenging activity and antilipid peroxidation. In contrast, the number of hydroxyl groups on the B-ring exhibited a positive relationship with their inhibitory activities.