Novel detection of formylated phloroglucinol compounds (FPCs) in the wound wood of Eucalyptus globulus and E. nitens

Journal of Chemical Ecology

Volumn 29, Issue 4, 2003, Pages 881-898

  Eyles, Alieta ^a,b   Davies, Noel W ^c   Mohammed, Caroline ^a,b,d  

^a Co operative Res Ctr S P Forest ^*  (Australia)

^b UNIVERSITY OF TASMANIA   (Australia)

^c UNIVERSITY OF TASMANIA   (Australia)

^d CSIRO   (Australia)

Author keywords

Antimicrobial; Antioxidant; Eucalyptus; HPLC; Negative ion electrospray mass spectrometry; Wood extractives

Indexed keywords

FLAVANONE DERIVATIVE; GLYCOSIDE; MACROCARPAL A; MACROCARPAL B; PHLOROGLUCINOL DERIVATIVE; PLANT EXTRACT; POLYPHENOL DERIVATIVE; PROANTHOCYANIDIN DERIVATIVE; SIDEROXYLONAL A; SIDEROXYLONAL B; STILBENE DERIVATIVE; TANNIN DERIVATIVE; UNCLASSIFIED DRUG;

FUNGUS; HOST-PATHOGEN INTERACTION; INOCULATION; PHYSIOLOGICAL RESPONSE; PHYTOCHEMISTRY; WOUNDING;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; BASIDIOMYCETES; BIOASSAY; CHEMICAL ANALYSIS; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; CONTROLLED STUDY; EUCALYPTUS; EUCALYPTUS GLOBULUS; EUCALYPTUS NITENS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HOST PATHOGEN INTERACTION; IN VITRO STUDY; INOCULATION; MASS SPECTROMETRY; NONHUMAN; TREE; WOOD; WOUND;

BASIDIOMYCOTA; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; EUCALYPTUS; MASS SPECTROMETRY; PHLOROGLUCINOL; PLANT EXTRACTS;

BACTERIA (MICROORGANISMS); BASIDIOMYCOTA; EUCALYPTUS; EUCALYPTUS GLOBULUS; EUCALYPTUS NITENS; FUNGI;

EID: 0242584486     PISSN: 00980331     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1022979632281     Document Type: Article

References (37)

1. AKANO, T., KOMIYA, T., HORI, M., and GOTO, M. 1981. Isolation and characterization of euglobals from Eucalyptus globulus Labill. by preparative reversed phase liquid chromatography. J. Chromatogr. 13:347-355.
2. BARRY, K. M. 2001. Antimicrobial defence in Eucalyptus nitens sapwood. PhD dissertation. University of Tasmania. Australia.
3. BARRY, K. M., PEARCE, R. B., and MOHAMMED, C. M. 2000. Properties of reaction zones associated with decay from pruning wounds in plantation-grown Eucalyptus nitens. For. Pathol. 30:233-245.
4. BARRY, K. M., DAVIES, N. W., and MOHAMMED, C. M. 2001. Identification of hydrolysable tannins in the reaction zone of Eucalyptus nitens wood by high performance liquid chromatography-electrospray ionisation mass spectrometry. Phytochem. Anal. 12:120-127.
5. BAUER, A. W., KIRBY, W. M. M., SHERRIS, J. C., and TURCK, M. 1966. Antibiotic susceptibility test by a standardised single disk method. Am. J. Clin. Pathol. 45:493-496.
6. BAUM, S. and SCHWARZE, F. W. M. R. 2002. Large-leaved lime (Tilia platyphyllos) has a low ability to compartmentalize decay fungi via reaction zone formation. New Phytol. 154:481-490.
7. CADAHIA, E., CONDE, E., GARCIA VALLEJO, M. C., and Fernandez De Simon, B. 1997. "Tannin composition of Eucalyptus camaldulensis, E. globulus and E. rudis: wood." Holzforschung 51:119-124.
8. CLOSE, D. C., DAVIES, N. W., and BEADLE, C. L. 2001. Temporal variation of tannins (galloylglucoses), flavonols and anthocyanins in leaves of Eucalyptus nitens seedlings: implications for light attenuation and antioxidant activities. Ajust. J. Plant Physiol. 28:269-278.
9. DELORME, L. and LIEUTIER, F. 1990. Monoterpene composition of the preformed and induced resins of Scots pine, and their effect on bark beetles and associated fungi. Eur. J. For. Pathol. 20:304-316.
10. ESCHLER, B. M. and FOLEY, W. J. 1999. A new sideroxylonal from Eucalyptus melliodora foliage. Aust. J. Chem. 52:541-556.
11. ESCHLER, B. M., PASS, D. M., WILLIS, R., and FOLEY, W. J. 2000. Distribution of foliar formylated phloroglucinol derivatives amongst Eucalyptus species. Biochem. Syst. Ecol. 28:813-824.
12. GHISALBERTI, E. L. 1996. Bioactive acylphloroglucinol derivatives from Eucalyptus species. Phytochemistry 41:7-22.
13. HARBORNE, J. B. and WILLIAMS, C. A. 2000. Advances in flavonoid research since 1992. Phytochemistry 55:481-504.
14. HILLIS, W. E. and YAZAKI, Y. 1975. Kinos of Eucalyptus species and their acid degradation products. Phytochemistry 13:495-498.
15. HIRANO, T., TANAKA, H., and ENOKI, A. 1997. Relationship between production of hyroxyl radicals and degradation of wood by the brown not fungus, Tyromyces palustris. Holzforschung 51:389-395.
16. KIM, J. P., LEE, I. K., YUN, B. S., CHUNG, S. H., SHIM, G. S., KOSHINO, H., and YOO, I. D. 2000. Ellagic acid rhamnosides from the stem bark of Eucalyptus globulus. Phytochemistry 57:587-591.
17. LAWLER, I. R., ESCHLER, B. M., SCHLIEBS, D. M., and FOLEY, W. J. 1999. Relationship between chemical functional groups on Eucalyptus secondary metabolites and their effectiveness as marsupial antifeediants. J. Chem. Ecol. 25:2561-2573.
18. LAWLER, I. R., FOLEY, W. J., and ESCHLER, B. M. 2000. Foliar concentration of a single toxin creates habitat patchiness for a marsupial folivore. Ecology 81:1327-1338.
19. LIESE, W. and DUJESIEFKEN, D. 1990. Principles of compartmentalisation in trees. Third Euro African Regional Wood Anatomy Symposium organized by the Wood Science and Technology Laboratories of the ETH. IAWA Bulletin 11:129-130.
20. OSAWA, K., YASUDA, H., MORITA, H., TAKEYA, K., and ITOKAWA, H. 1996. Macrocarpals H, I, and J from the leaves of Eucalyptus globulus. J. Nat. Prod. 59:823-827.
21. PEARCE, R. B. 1990. Occurrence of decay-associated xylem suberization in a range of woody species. Eur. J. For. Pathol. 20:275-289.
22. PEARCE R. B. 1996. Tansley Review No. 87. Antimicrobial defences in the wood of living trees. New Phytol. 132:203-233.
23. RAFFA, K. F., BERRYMAN, A. A., SIMASKO, J., TEAL, W., and WONG, B. L. 1985. Effects of grand fir monoterpenes on the fir engraver, Scolytus vertralis (Coleoptera: Scolytidae), and its symbiotic fungus. Environ. Entomol. 14:552-556.
24. SATOH, H., ETOH, H., WATANABE, N., KAWAGISHI, H., ARAI, K., and INA, K. 1992. Structures of sideroxylonals from Eucalyptus sideroxylon. Chem. Lett. 10:1917-1920.
25. SCHWARZE, F. ENGELS, J., and MATTECK, C. 1999. Fungal Strategies of Wood Decay in Trees. Springer-Verlag. Berlin, 185 pp.
26. SHIGO, A. L. and MARX, H. G. 1977. Compartmentalization of decay in trees. Agriculture Information Bulletin No. 405. United States Department of Agriculture Forest Service, Washington, D.C.
27. SINGH, I. P. and ETOH, H. 1997. Biological activities of phloroglucinol derivatives from Eucalyptus spp. Nat. Prod. Sci. 30:1-7.
28. STAPLEY, J., FOLEY, W. J., CUNNINGHAM, R., and ESCHLER, B. 2000. How well can common brushtail possums regulate their intake of Eucalyptus toxins? J. Comp. Physiol. B 170:211-218.
29. TAKASAKI, M., KONOSHIMA, T., KOZUKA, M., HARUNA, M., ITO, K., and SHINGU, T. 1994a. Structures of euglobals-G1, -G2, -G3, -G4 and -G5 from Eucalyptus grandis. Chem. Pharm. Bull. 42:2591-2597.
30. TAKASAKI, M., KONOSHIMA, T., KOZUKA, M., HARUNA, M., ITO, K., and YOSHIDA, S. 1994b. Four euglobals from Eucalyptus blakelyi. Chem. Pharm. Bull. 42:2177-2179.
31. TURNBALL, J. W. 2000. Economics and social importance of eucalypts. pp. 1-9, in P. J. Keane, G. A. Kile, F. D. Podger, and B. N. Brown (eds.). Diseases and Pathogens of Eucalypts. CSIRO Publishing. Australia.
32. VAN DOORSLAER, S., DEDONDER, A., DE BLOCK, M., and CALLENS, F. 1999. Oxidative stress in plants. EPR monitoring in DMPO-DMSO based extracts. J. Plant Physiol. 154:132-136.
33. WARDLAW, T. J., KILE, G. A., and DIANESE, J. C. 2000. Diseases of eucalypts associated with viruses, phytoplasmas, bacteria and nematodes, pp. 103-119, in P. J. Keane, G. A. Kile, F. D. Podger, and B. N. Brown (eds.). Diseases and Pathogens of Eucalypts. CSIRO Publishing, Melbourne, Australia.
34. WHITE, D. A., BEADLE, C. L., WORLEDGE, D., HONEYSETT, J. L., and CHERRY, M. L. 1998. The influence of drought on the relationship between leaf and conducting sapwood area in Eucalyptus globulus and Eucalyptus nitens. Trees Struc. Funct. 12:406-414.
35. WILKES, J. 1986. Host attributes affecting patterns of decay in a regrowth eucalypt. V. Barrier zones. Holzforschung 40:37-42.
36. YAMAMDA, T. 2001. Defence mechanisms in the sapwood of living trees against microbial infection. J. For. Res. 6:127-137.
37. YAMAKOSHI, Y., MURATA, M., SHIMIZU, A., and HOMMA, S. 1992. Isolation and characterization of macrocarpals B-G. Biosci. Biotech. Biochem. 56:1570-1576.