Skip to content
Licensed Unlicensed Requires Authentication Published by De Gruyter July 5, 2005

Chemical composition and antifungal activity of essential oil isolated from Chamaecyparis formosensis Matsum. wood

  • Sheng-Yang Wang , Chi-Lin Wu , Fang-Hua Chu , Shih-Chang Chien , Yueh-Hsiung Kuo , Lie-Fen Shyur and Shang-Tzen Chang
From the journal Holzforschung

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.

:

Corresponding author. School of Forestry and Resource Conservation, National Taiwan University, No. 1, Section 4 Roosevelt Road, Taipei 115, Taiwan Tel.: +886-2-23630231-3196 Fax: +886-2-33664626 E-mail:
Corresponding author. School of Forestry and Resource Conservation, National Taiwan University, No. 1, Section 4 Roosevelt Road, Taipei 115, Taiwan Tel.: +886-2-23630231-3196 Fax: +886-2-33664626 E-mail:

References

Ahmed, A.A., Mahmoud, A.. (1998). Jasmol, a rare tricyclic eudesmane sesquiterpene and six other new sesquiterpenoids from Jasonia candicans. Tetrahedron54:8141–8152.Search 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.Search 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.1999.080Search 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.2000.041Search 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:1010397801826Search 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/b106906cSearch 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.198600037Search 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.198600033Search 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-2002-34414Search 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-2001-12001Search 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-RSearch 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)83216-0Search 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/np50124a019Search in Google Scholar

Kafuka, K., Ichikawa, N. (1931) The volatile compounds from leaves of Chamaecyparis formosensis. Nippon Kagaku Kaishi52:222–228.10.1246/nikkashi1921.52.222Search 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-RSearch 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-2002-5-613Search 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/np0101402Search 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.Search 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)99943-5Search 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.Search 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/jf991026gSearch in Google Scholar

Published Online: 2005-07-05
Published in Print: 2005-05-01

© by Walter de Gruyter Berlin New York

Downloaded on 25.4.2024 from https://www.degruyter.com/document/doi/10.1515/HF.2005.049/html
Scroll to top button