Antifungal activity of cinnamaldehyde and eugenol congeners against wood-rot fungi.

In this study, the antifungal activities of cinnamaldehyde and eugenol congeners against white-rot fungus Lenzites betulina and brown-rot fungus Laetiporus sulphureus were evaluated and the relationships between the antifungal activity and the chemical structures were also examined. Results from antifungal tests revealed that cinnamaldehyde, alpha-methyl cinnamaldehyde, (E)-2-methylcinnamic acid, eugenol and isoeugenol exhibited strong antifungal activity against all fungi tested. Results derived from the chemical structure-antifungal activity relationship study suggested that compounds with an aldehyde group or an acid group, a conjugated double bond and a length of CH chain outside the ring affect their antifungal properties. Furthermore, the presence of the methyl moiety in the ortho position may have a considerable influence on the inhibitory action against L. betulina and L. sulphureus. In addition, the lipophilicity may play, in part, a crucial role in determining the toxicity of phenylpropenes.

[1]  Ju-Yun Liu,et al.  Chemical polymorphism and antifungal activity of essential oils from leaves of different provenances of indigenous cinnamon (Cinnamomum osmophloeum). , 2006, Bioresource technology.

[2]  Shang-Tzen Chang,et al.  Antitermitic activity of leaf essential oils and components from Cinnamomum osmophleum. , 2002, Journal of agricultural and food chemistry.

[3]  D. Wedge,et al.  Fungicidal activity of natural and synthetic sesquiterpene lactone analogs. , 2000, Phytochemistry.

[4]  Y. Kuo,et al.  Comparison of the Antifungal Activity of Cadinane Skeletal Sesquiterpenoids from Taiwania (Taiwania cryptomerioides Hayata) Heartwood , 2000 .

[5]  R. Kondo,et al.  Antifungal compounds in heartwood extractives of hinoki (Chamaecyparis obtusa Endl.) , 1986 .

[6]  P. Rudman,et al.  The Causes of Natural Durability in Timber , 1961 .

[7]  Hyun Kyung Kim,et al.  Acaricidal activity of cinnamaldehyde and its congeners against Tyrophagus putrescentiae (Acari: Acaridae) , 2004 .

[8]  Shang-Tzen Chang,et al.  Antifungal property of the essential oils and their constituents from Cinnamomum osmophloeum leaf against tree pathogenic fungi , 2005 .

[9]  Kun-Hsien Tsai,et al.  Chemical composition and mosquito larvicidal activity of essential oils from leaves of different Cinnamomum osmophloeum provenances. , 2004, Journal of agricultural and food chemistry.

[10]  Shang-Tzen Chang,et al.  Synergistic effects of cinnamaldehyde in combination with eugenol against wood decay fungi. , 2008, Bioresource technology.

[11]  Y. Kuo,et al.  Structure-activity relationships of cadinane-type sesquiterpene derivatives against wood-decay fungi , 2005 .

[12]  Shang-Tzen Chang,et al.  Antifungal activities of essential oils and their constituents from indigenous cinnamon (Cinnamomum osmophloeum) leaves against wood decay fungi. , 2005, Bioresource technology.

[13]  Y. Kuo,et al.  Chemical composition and antifungal activity of essential oil isolated from Chamaecyparis formosensis Matsum. wood , 2005 .

[14]  T. Schultz,et al.  Naturally durable heartwood: evidence for a proposed dual defensive function of the extractives. , 2000, Phytochemistry.

[15]  P. Rudman.  The Causes of Natural Durability in Timber - Pt. XVIII Further Notes on the Fungi Toxicity of Wood Extractives , 1965 .

[16]  S. C. Chang,et al.  Antibacterial activity of leaf essential oils and their constituents from Cinnamomum osmophloeum. , 2001, Journal of ethnopharmacology.

[17]  Y. Kuo,et al.  Antifungal Compounds in the Ethyl Acetate Soluble Fraction of the Extractives of Taiwania (Taiwania cryptomerioides Hayata) Heartwood , 1999 .

[18]  Y. Ahn,et al.  Acaricidal activity of clove bud oil compounds against Dermatophagoides farinae and Dermatophagoides pteronyssinus (Acari: Pyroglyphidae). , 2003, Journal of agricultural and food chemistry.