Antifungal properties of terpenoids in Picea abies against Heterobasidion parviporum

Forest Pathology

Volumn 44, Issue 5, 2014, Pages 353-361

  Kusumoto, N ^a,b   Zhao, T ^b   Swedjemark, G ^c   Ashitani, T ^d   Takahashi, K ^d   Borg Karlson, A K ^b  

^a AKITA PREFECTURAL UNIVERSITY   (Japan)

^b ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

^c THE FORESTRY RESEARCH INSTITUTE OF SWEDEN   (Sweden)

^d YAMAGATA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROBASIDION PARVIPORUM; PICEA ABIES;

EID: 84907930490     PISSN: 14374781     EISSN: 14390329     Source Type: Journal    
DOI: 10.1111/efp.12106     Document Type: Article

References (46)

1. Bendz-Hellgren, M.; Lipponen, K.; Solheim, H.; Thomsen, I. M., 1998: The Nordic countries. In: Heterobasidion annosum: Biology, ecology, impact and control. Ed. by Woodward, S.; Stenlid, J.; Karjalainen, R.; Hutterman, A. Wallingford, UK: CABI, pp. 333-345.
2. Borg-Karlson, A.-K.; Lindström, M.; Norin, T.; Persson, M.; Valterová, I., 1993: Enantiomeric composition of monoterpene hydrocarbons in different tissues of Norway spruce, Picea abies (L.) Karst. A multi-dimensional gas chromatography study. Acta Chem. Scand. 47, 138-144.
3. Cheng, S.-S.; Liu, J.-Y.; Hsui, Y.-R.; Chang, S.-T., 2006: Chemical polymorphism and antifungal activity of essential oils from leaves of different provenances of indigenous cinnamon (Cinnamomum osmophloeum). Bioresour. Technol. 97, 306-312.
4. Cobb, F. W. Jr; Krstic, M.; Zavarin, E.; Barber, H. W. Jr, 1968: Inhibitory effects of volatile oleoresin components on Fomes annosus and four Ceratocystis species. Phytopathology 58, 1199-1324.
5. Dorman, H. J. D.; Deans, S. G., 2000: Antimicrobial agents from plants: antibacterial activity of plant volatile oils. J. Appl. Microbiol. 88, 308-316.
6. Eberhardt, T. L.; Han, J. S.; Micales, J. A.; Young, R. A., 1994: Decay resistance in conifer seed cones: roles of resin acids as inhibitors of decomposition by white-rot fungi. Holzforschung 48, 278-284.
7. Eckhardt, L. G.; Menard, R. D.; Gray, E. D., 2009: Effects of oleoresins and monoterpenes on in vitro growth of fungi associated with pine decline in the Southern United States. Forest Pathol. 39, 157-167.
8. Ekman, R.; Sjoholm, R., 1979: Hydroxylation of dehydroabietic acid by Fomes annosus. Acta Chem. Scand. 33, 76-78.
9. Ekman, R.; von Weissenberg, K., 1981: Association between some silvicultural, physical, and chemical properties of Picea abies and spread of Fomes annosus. Acta Acad. Abo., B 41, 1-22.
10. Enoki, A., 1976: Isomerization and autoxidation of resin acids. Wood Res. 59/60, 49-57.
11. Gershenzon, J.; Dudareva, N., 2007: The function of terpene natural products in the natural world. Nat. Chem. Biol. 3, 408-414.
12. Gibbs, J. N., 1968: Resin and the resistance of conifers to Fomes annosus. Ann. Bot. 32, 649-665.
13. Gref, R.; Hakansson, C.; Henningsson, B.; Hemming, J., 2000: Influence of wood extractives on brown and white rot decay in Scots pine heart-, light- and sapwood. Mater. Organismen 33, 119-128.
14. Häkkinen, S. T.; Lackman, P.; Nygrén, H.; Oksman-Caldentey, K.-M.; Maaheimo, H.; Rischer, H., 2012: Differential patterns of dehydroabietic acid biotransformation by Nicotina tabacum and Catharanthus roseus cells. J. Biotechnol. 157, 287-294.
15. Henriks, M.-L.; Ekman, R.; von Weissenberg, K., 1979: Bioassay of some resin and fatty acids with Fomes annosus. Acta Acad. Abo. B 39, 1-7.
16. Kännaste, A.; Zhao, T.; Lindström, A.; Stattin, E.; Långström, B.; Borg-Karlson, A.-K., 2013: Odors of Norway spruce (Picea abies L.) seedlings: differences due to age and chemotype. Trees 27, 149-159.
17. Karlsson, M.; Hietala, A. M.; Kvaalen, H.; Solheim, H.; Olson, Å.; Stenlid, J.; Fossdal, C. G., 2007: Quantification of host and pathogen DNA and RNA transcripts in the interaction of Norway spruce with Heterobasidion parviporum. Physiol. Mol. Plant Pathol. 70, 99-109.
18. Klepzig, K. D.; Schlyter, F., 1999: Laboratory evaluation of plant-derived antifeedants against the pine weevil Hylobius abietis (Coleoptera: Curculionidae). J. Econ. Entomol. 92, 644-650.
19. Korhonen, K.; Stenlid, J., 1998: Biology of Heterobasidion annosum. In: Heterobasidion annosum: Biology, ecology, impact and control. Ed. by Woodward, S.; Stenlid, J.; Karjalainen, R.; Hutterman, A. Wallingford, UK: CABI, pp. 43-70.
20. Korhonen, K.; Capretti, P.; Karjalainen, R.; Stenlid, J., 1998: Disribution of Heterobasidion annosum intersterility groups in Europe. In: Heterobasidion annosum: Biology, ecology, impact and control. Ed. by Woodward, S.; Stenlid, J.; Karjalainen, R.; Hutterman, A. Wallingford, UK: CABI, pp. 93-104.
21. Kusumoto, N.; Ashitani, T.; Murayama, T.; Ogiyama, K.; Takahashi, K., 2010: Antifungal abietane-type diterpenes from the cones of Taxodium distichum Rich. J. Chem. Ecol. 36, 1381-1386.
22. Martin, V. J. J.; Yu, Z.; Mohn, W. W., 1999: Recent advances in understanding resin acid biodegradation: microbial diversity and metabolism. Arch. Microbiol. 172, 131-138.
23. Martin, D.; Tholl, D.; Gershenzon, J.; Bohlmann, J., 2002: Methyl jasmonate induces traumatic resin ducts, terpenoid resin biosynthesis, and terpenoid accumulation in developing xylem of Norway spruce stems. Plant Physiol. 129, 1003-1018.
24. Martínez-Iñigo, M. J.; Claassen, F. W.; Joseleau, B.; Van Beek, T. A.; Lenon, G.; Sierra-Alvarez, R., 2000: Evaluation of fungal capacity for detoxification of extractives in scots pine sapwood. Environ. Technol. 21, 569-575.
25. Miyazawa, M.; Hashimoto, Y., 2002: Antimicrobial and bactericidal activities of esters of 2-endo-hydroxy-1, 8-cineole as new aroma chemicals. J. Agric. Food Chem. 50, 3522-3526.
26. Miyazawa, M.; Miyasato, Y., 2001: Biotransformation of (+)- and (-)-bornyl acetate using the plant parasitic fungus Glomerella cingulata as a biocatalyst. J. Chem. Technol. Biotechnol. 76, 220-224.
27. Miyazawa, M.; Shindo, M.; Shimada, T., 2001: Oxidation of 1, 8-cineole, the monoterpene cyclic ether originated from Eucalyptus polybractea, by cytochrome P450 3A enzymes in rat and human liver microsomes. Drug Metab. Dispos. 29, 200-205.
28. Nano, G. M.; Binello, A.; Cravotto, G.; Bianco, M. A., 2005: Biotransformation of (-)-bornyl acetate using submerged cultures of Collybia velutipes, Trametes hirsuta and Ganoderma applanatum. J. Chem. Technol. Biotechnol. 80, 657-661.
29. Pastorova, I.; van der Berg, K. J.; Boon, J. J.; Verhoeven, J. W., 1997: Analysis of oxidized diterpenoid acids using thermally assisted methylation with TMAH. J. Anal. Appl. Pyrol. 43, 41-57.
30. Persson, M.; Borg-Karlson, A.-K.; Norin, T., 1993: Enantiomeric composition of six chiral monoterpene hydrocarbons in different tissues of Picea abies. Phytochemistry 33, 303-307.
31. Pettersson, E. M.; Birgersson, G.; Witzgall, P., 2001: Synthetic attractants for the bark beetle parasitoid Coeloides bostrichorum Giraud (Hymenoptera: Braconidae). Naturwissenschaften 88, 88-91.
32. Phillips, M. A.; Croteau, R. B., 1999: Resin-based defenses in conifers. Trends Plant Sci. 4, 184-190.
33. Rennerfelt, E.; Nacht, G., 1955: The fungicidal activity of some constituents from heartwood of conifers. Svensk Bot. Tidskr 49, 419-432.
34. Schewe, H.; Mirata, M. A.; Holtmann, D.; Schrader, J., 2011: Biooxidation of monoterpenes with bacterial monooxygenases. Process Biochem. 46, 1885-1899.
35. Schmidt, A.; Zeneli, G.; Hietala, A. M.; Fossdal, C. G.; Krokene, P.; Christiansen, E.; Gershenzon, J., 2005: Chapter one induced chemical defenses in conifers: biochemical and molecular approaches to studying their function. Recent Adv. Phytochem. 39, 1-28.
36. Staccioli, G.; Sturaro, A.; Parvoli, G.; Menchi, G.; Matteoli, U., 1999: The lipophilic extractives of an interglacial fossil Picea abies from Zeifen (Germany). Holzforschung 53, 391-396.
37. Stenlid, J., 1987: Controlling and predicting the spread of Heterobasidion annosum from infected stumps and trees of Picea abies. Scand. J. For. Res. 2, 187-198.
38. Stenlid, J.; Wästerlund, I., 1986: Estimating the frequency of stem rot in Picea abies using an increment borer. Scand. J. For. Res. 1, 303-308.
39. Suga, T.; Hirata, T., 1990: Biotransformation of exogenous substrates by plant cell cultures. Phytochemistry 29, 2393-2406.
40. Swedjemark, G.; Stenlid, J.; Karlsson, B., 1997: Genetic variation among clones of Picea abies in resistance to growth of Heterobasidion annosum. Silvae Genet. 46, 369-376.
41. Van Beek, T. A.; Claassen, F. W.; Dorado, J.; Godejohann, M.; Sierra-Alvarez, R.; Wijnberg, J. B. P. A., 2007: Fungal biotransformation products of dehydroabietic acid. J. Nat. Prod. 70, 154-159.
42. Yano, S.; Nakamura, T.; Uehara, T.; Furuno, T.; Takahashi, A., 1994: Biotransformation of terpenoids in conifers by microorganisms I. Hydroxylation of dehydroabietic acid by Chaetomium cochliodes. Mokuzai Gakkaishi 40, 1226-1232.
43. Zamponi, L.; Michelozzi, M.; Capretti, P., 2007: Terpene response of Picea abies and Abies alba to infection with Heterobasidion s.l. Forest Pathol. 37, 243-250.
44. Zeneli, G.; Krokene, P.; Christiansen, E.; Krekling, T.; Gershenzon, J., 2006: Methyl jasmonate treatment of mature Norway spruce (Picea abies) trees increases the accumulation of terpenoid resin components and protects against infection by Ceratocystis polonica, a bark beetle-associated fungus. Tree Physiol. 26, 977-988.
45. Zhao, T.; Krokene, P.; Björklund, N.; Långström, B.; Solheim, H.; Christiansen, E.; Borg-Karlson, A.-K., 2010: The influence of Ceratocystis polonica inoculation and methyl jasmonate application on terpene chemistry of Norway spruce, Picea abies. Phytochemistry 71, 1332-1341.
46. Zhao, T.; Krokene, P.; Hu, J.; Christiansen, E.; Björklund, N.; Långström, B.; Solheim, H.; Borg-Karlson, A.-K., 2011: Induced terpene accumulation in Norway spruce inhibits bark beetle colonization in a dose-dependent manner. PLoS ONE 6, e26649.