Chemical composition and antifungal activity of essential oil isolated from Chamaecyparis formosensis Matsum. wood
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Sheng-Yang Wang
Abstract
The chemical composition of the essential oil of Chamaecyparis formosensis wood has been examined. GC-MS data and retention indices for reference samples were used to identify 32 constituents. α-Eudesmol (18.06%), β-guaiene (8.0%), (–)-β-cadinene (7.89%), γ-costal (7.03%), α-muurolol (6.49%), 4α-hydroxy-4β-methyldihydrocostol (5.52%), σ-selinene (4.78%), santolina triene (4.60%), eremophilene (4.32%), humulene (4.11%), myrtenol (4.11%), and τ-cadinene (3.25%) were the most abundant components. Tests with the typical wood decay fungi, Laetiporus sulphureus and Trametes versicolor, proved the antifungal activity of the oil, as the growth of L. sulphureus and T. versicolor was inhibited at concentrations of 50 and 100 μg ml−1, respectively. The following characteristic volatile compounds were isolated and purified from ethyl acetate fractions: epi-cubenol, chamaecynone, myrtenol, cis-myrtanol, 12-hydroxyisointermedenol and 4α-hydroxy-4β-methyldi-hydrocostol. Chamaecynone possessed the strongest antifungal activity, with an antifungal index of 88.2% and 67.3% for L. sulphureus and T. versicolor at a dose of 50 μg ml−1, respectively.
References
Ahmed, A.A., Mahmoud, A.. (1998). Jasmol, a rare tricyclic eudesmane sesquiterpene and six other new sesquiterpenoids from Jasonia candicans. Tetrahedron54:8141–8152.Suche in Google Scholar
Chang, S.T., Wu, C.L., Wang, S.Y., Su, Y.C., Kuo, Y.H. (1998) Studies on the antifungal compounds in the heartwood extractives of Taiwania (Taiwania cryptomerioides Hayata) (I): isolation and identification of antifungal compounds in hexane soluble fraction (in Chinese with English abstract). For. Prod. Ind.17:287–304.Suche in Google Scholar
Chang, S.T., Wang, S.Y., Wu, C.L., Su, Y.C., Kuo, Y.H. (1999) Antifungal compounds in the ethyl acetate soluble fraction of the extractives of Taiwania (Taiwania cryptomerioides Hayata) heartwood. Holzforschung53:487–490.10.1515/HF.1999.080Suche in Google Scholar
Chang, S.T., Wang, S.Y., Wu, C.L., Chen, P.F., Kuo, Y.H. (2000) Comparison of the antifungal property of cadinane skeletal sesquiterpenoids from Taiwania (Taiwania cryptomerioides Hayata) heartwood. Holzforschung54:241–245.10.1515/HF.2000.041Suche in Google Scholar
Chang, S.T., Cheng, S.S., Wang, S.Y. (2001) Antitermitic property of essential oils and components from Taiwania (Taiwania cryptomerioides). J. Chem. Ecol.27:717–724.10.1023/A:1010397801826Suche in Google Scholar
Deagostino, A., Tivola, P.B., Prandi, C., Venturello, P. (2001) Lithium-potassium superbases as key reagents for the base-catalysed isomerisation of some terpenoids. J. Chem. Soc. Perkin Trans 122:2856–2860.10.1039/b106906cSuche in Google Scholar
Fang, J.M., Lai, L.J., Cheng, Y.S. (1986a) The constituents of the leaves of Chamaecyparis formosensis. J. Chin. Chem. Soc.33:265–266.10.1002/jccs.198600037Suche in Google Scholar
Fang, J.M., Sheu, C.M., Cheng, Y.S. (1986b) A study of the constituents of the bark of Chamaecyparis formosensis. J. Chin. Chem. Soc.33:245–249.10.1002/jccs.198600033Suche in Google Scholar
Flach, A., Gregel, B., Simionatto, E., da Sliva, U.F., Zanatta, N., Morel, A.F., Linares, C.E.B., Alves, S.B. (2002) Chemical analysis and antifungal property of the essential oil of Calea clematidea. Planta Med.68(9):836–838.10.1055/s-2002-34414Suche in Google Scholar
Gallori, S., Bilia, A.R., Mulinacci, N., Biccchi, C., Rubiolo, P., Vincieri, F.F. (2001) Identification of volatile constituents of Tambourissa leptophylla. Planta Med.67(3):290–292.10.1055/s-2001-12001Suche in Google Scholar
Gonzalez, A., Barrera, J.B., Mendez, J.T., Sanchez, M.L., Martinez, J.L.E. (1992) Sesquiterpene alcohols from Gonospermum fructicosum. Phytochemistry31(5):1816–1817.10.1016/0031-9422(92)83155-RSuche in Google Scholar
Harayama, T.H.C., Inubushi, Y. (1977) Total synthesis of DL-chamaecynone, a termiticidal norsesquiterpene. Tetrahedron Lett.37:3273–3276.10.1016/S0040-4039(01)83216-0Suche in Google Scholar
Hsu, K.-C., Fang, J.-M., Cheng, Y.-S. (1995) Diterpenes from pericarps of Chamaecyparis formosensis. J. Nat. Prod.58:1592–1595.10.1021/np50124a019Suche in Google Scholar
Kafuka, K., Ichikawa, N. (1931) The volatile compounds from leaves of Chamaecyparis formosensis. Nippon Kagaku Kaishi52:222–228.10.1246/nikkashi1921.52.222Suche in Google Scholar
Kim, K.Y., Lee, S.G. (1997) Complete assignment of 1H and 13C NMR spectra of trans- and cis-myrtanol. Magn. Reson. Chem.35:451–454.10.1002/(SICI)1097-458X(199707)35:7<451::AID-OMR113>3.0.CO;2-RSuche in Google Scholar
Krauze-Baranowska, M., Mardarowicz, M., Wiwart, M., Poblocka, L., Dynowska, M. (2002) Antifungal property of the essential oils from some species of the genus Pinus. Z. Naturforschung C-A J. of Biosciences57(5–6):478–482.10.1515/znc-2002-5-613Suche in Google Scholar
Kuo, Y.C., Chen, C.H., Chien, S.C., Lin, Y.L. (2002) Five new cadinane-type sesquiterpenes from the heartwood of Chamaecyparis obtuse var. formosana. J. Nat. Prod.65(1):25–28.10.1021/np0101402Suche in Google Scholar
Liu, Y.C., Lu, F.Y., Ou, C.H. (1988) Trees of Taiwan. Monographic Publication No. 7. College of Agriculture, National Chung Hsing University. Taichung, Taiwan. pp. 91–92.Suche in Google Scholar
Nozoe, T., Chen, Y.S., Toda, T. (1966) The structure of chamaecynone – a novel norsesquitenoid from Chamaecyparis formosensis Matsum. Tetrahedron Lett.31:3663–3669.10.1016/S0040-4039(01)99943-5Suche in Google Scholar
Saito, K., Okabe, T., Inamori, Y., Tsujibo, H., Miyake, Y., Hiraoka, Y., Ishida, N. (1996) The biological properties of monoterpenes – hypotensive effects on rats and antifungal activities on plant pathogenic fungi of monoterpenes. Mokuzai Gakkaiishi42(7):677–680.Suche in Google Scholar
Tellez, M.R., Dayan, F.E., Schrader, K.K., Wedge, D.E., Duke, S.O. (2000) Composition and some biological activities of the essential oils of Callicarpa americana. J. Agric. Food Chem.48(7):3008–3012.10.1021/jf991026gSuche in Google Scholar
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Artikel in diesem Heft
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Artikel in diesem Heft
- Molecular dynamics study of lignin constituents in water
- Oxidative cellulose degradation by cellobiose dehydrogenase from Phanerochaete chrysosporium: A model compound study
- Characterization of active oxygen species under oxygen-alkali bleaching conditions
- Erythro/threo ratio of β-O-4-5 structures as an important structural characteristic of lignin. Part 4: Variation in the erythro/threo ratio in softwood and hardwood lignins and its relation to syringyl/guaiacyl ratio
- Stereoisomers of 3,3′-dimethoxy-4,4′-stilbenequinone
- Liquefaction of CCA-treated wood and elimination of metals from the solvent by precipitation
- Condensed tannins from steamed Acacia mearnsii bark
- Chemical composition and antifungal activity of essential oil isolated from Chamaecyparis formosensis Matsum. wood
- Direct measurement of strain distribution along a wood bond line. Part 1: Shear strain concentration in a lap joint specimen by means of electronic speckle pattern interferometry
- Direct measurement of strain distribution along a wood bond line. Part 2: Effects of adhesive penetration on strain distribution
- Rate-independent mechanical behavior of biaxially stressed wood: Experimental observations and constitutive modeling as an orthotropic two-surface elasto-plastic material
- Characterization of sugar maple wood-polymer composites: Monomer retention and polymer retention
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- Wood-water sorption isotherm prediction with artificial neural networks: A preliminary study
- Hygroscopicity of resorcinol-formaldehyde resin and aqueous vinyl polymer-isocyanate resin in high humidity
- Modelling anisotropic maturation strains in wood in relation to fibre boundary conditions, microstructure and maturation kinetics
- Properties of chemically and mechanically isolated fibres of spruce (Picea abies [L.] Karst.). Part 3: Mechanical characterisation
- Resistance of thermo-hygro-mechanically densified wood to colonisation and degradation by brown-rot fungi
- Microbial colonizers of freshly sawn yellow-poplar (Liriodendron tulipifera L.) lumber in two seasons. Part 3: Yeasts
- Efficacy of a copper(II)/oxine copper wood preservative mixture after 69 months of outdoor ground-contact exposure and a proposed mechanism to explain the observed synergism
- Differentiation of indoor wood decay fungi with MALDI-TOF mass spectrometry
- Horst H. Nimz celebrates his 75th birthday on April, 21st, 2005
- Erratum
