Endophytic Xylariaceae from Thai Plants: A Research Review
Keywords:
endophytic fungi, xylariaceae, Thailand, novel metabolitesAbstract
Endophytic fungi are present in all plant species investigated, and members of the Xylariaceae are especially common in tropical plants. There is major interest in endophytic fungi, because of their excellent track record concerning the production of
novel and often bioactive compounds including the anti-cancer drugs taxol and taxane. Studies in Thailand on endophytes over the past 20 years confirm the high presence of the Xylariaceae in many different Thai plants. Species of Xylaria stand out as the most frequent Xylariaceae isolated; although, Daldinia eschscholtzii has also been commonly isolated. DNA technology and chemical profiling have been shown to be invaluable in the identification of xylariaceous isolates which previously could not be identified to species level or even assigned to genera in many cases. Reference is made to those isolates which produce novel compounds or those exhibiting bioactive properties.
References
Adeboya, M., Edwards, R. L., Læssøe, T. & Maitland, D. J. (1995a). Metabolites of the higher fungi. Part 27. Berteric acid, cameronic acid and malaysic acid, three new polysubstoituted fatty acids related to cubensic acid from species of the fungus genus Xylaria. Journal of Chemical Research,Synopses, 9, 356-357.
Adeboya, M., Edwards, R. L., Læssøe, T.,Maitland, D. J. & Whalley, A. J. S. (1995b). Metabolites of the higher fungi. Part 28.Globosic acid and globoscin, a labile acid-lactone system from Xylaria globosa and Xylaria obovata. Journal of the Chemical Society. Perkins Transactions, 1, 2067-2072.
Anderson, J. R., Briant, C. E., Edwards, R. L., Mabelis, R. P., Poyser, J. P., Spencer, H. & Whalley, A. J. S. (1984a). Punctatin A(antibiotic M95464): X-ray crystal structure of a ses- quiterpene alcohol with a new carbon skeleton from the fungus Poronia punctata.Journal of the Chemical Society, Chemical Communications, 405-406.
Anderson, J. R., Edwards, R. L., Freer, A. A.,Mabelis, R. P., Poyser, J. P., Spencer, H. & Whalley, A. J. S. (1984b). Punctatins B and C
(antibiotics M95154 and M951560): further sesquiterpene alcohols from the fungus Poronia punctata. Journal of the Chemical
Society, Chemical Communications, 917-919.
Anderson, J. R., Edwards, R. L. & WhalLey, A. J.S. (1982). Metabolites of the higher fungi. Part 19. Serpenone, 3-methoxy-4-methyl-5 prop-1-
enylfuran-2(5H)-one, a new γ - butyrolactone from the fungus Hypoxylon serpens (Barrons strain)(Persoon ex Fries)Kickx. Journal of the
Chemical Society, Perkins Transactions 1,215-221.
Anderson, J. R., Edwards, R. L. & Whalley, A. J.S. (1983). Metabolites of the higher fungi. Part 21. 3-Methyl-3, 4-dihydroisocoumarins and
related compounds from the ascomycete family Xylariaceae. Journal of the Chemical Society. Perkins Transactions 1, 2185-2192.
Anderson, J. R., Edwards, R. L. & Whalley, A.J. S. (1985). Metabolites of the higher fungi. Part 22. 3-Butyl-3-methylsuccinic acid and a
-hexylidene-3-methylsuccinic acid from xylariaceous fungi. Journal of the Chemical Society. Perkins Transactions 1, 1481-1485.
Bitzer, J., Læssøe, T., Fournier, J., Kummer, V.,Decock, C., Tichy, H. V., Piepenbring, M.,Persoh, D. & Stadler, M. (2008). Affinities of Phylacia and the daldinoid Xylariaceae nferred from chemotypes of cultures and ribosomal DNA sequences. Mycological Research, 112 (2): 251-270
Brunner, F. & Petrini, O. (1992). Taxonomy of some Xylaria species and xylariaceous endo-phytes by isozyme electrophoresis. Mycologi-
cal Research, 96, 723-733.
Bussaban, B., Lumyong, S., Lumyong, P.,McKenzie, E. H. C. & Hyde, K. D. (2001). Endophytic fungi from Amomum siamense. Canadian Journal of Microbiology, 47, 943-948.
Chareprasert, S., Abdelghany, M. T., El-sheikh,H. H., Ahmed, A. F., Khalil, A. M. A, Sharples, G. P., Sihanonth, P., Soliman, H.G., Suwannasai, N., Whalley, A. J. S. & Whalley, M. A. (2012). Xylariaceae on the fringe. In C. Raghukumar (Ed), Biology of Marine Fungi (pp. 229-241). Berlin,
Heidelberg: Springer-Verlag Berlin Heidelberg.
Chareprasert, S., Piapukiew, J., Thienhirun, S.,Whalley, A. J. S. & Sihanonth, P. (2006).Endophytic fungi of teak leaves (Tectona
grandis L. and rain tree leaves Samanea saman Merr. World Journal of Biotechnology and Microbiology, 22(5), 481-486.
Chareprasert, S., Piapukiew, J., Whalley, A. J. S. & Sihanonth P. (2010). Endophytic fungi from selected mangrove plants in Chanthaburi,
Prachuap Kiri Khan and Ranong provinces,their potential as a source of antimicrobial and anticancer compounds. Botanica Marina, 53,
-564.
Daferner, M., Mensch, S., Anke, T. & Sterner, O.(1999). Hypoxysordarin, a new sordarin deri-vative from Hypoxyloncroceum. Zeitschrift für
Naturforschung C, 54(7-8): 474-480.
Edwards, R. L., Maitland, D. J., Scowen, I. A., DeSousa, A. J. T. & Whalley, A. J. S. (2001).Metabolites of the higher fungi. Part 32. Rosnecatrone, a phytotoxic Bicyclo [4.1.0]hept-3-en-2-one from the fungus Rosellinianecatrix Prill. Journal of the Chemical Society, Perkins Transactions 1,
-542.
Edwards, R. L., Maitland, D. J., Poyser, J. P. & Whalley, A. J. S. (1989). Metabolites of the higher fungi. Part 25. Puntaporonin G from the
fungus Poronia punctata (Linneus: Fries) Fries. Journal of the Chemical Society, Perkins Transactions 1, 57-65.
Edwards, R. L., Poyser, J. P. & Whalley, A. J. S.(1988). Metabolites of the higher fungi. Part 23. The puntaporonins. Novel bi-, tri, and
tetra-cyclic sesquiterpenes related to caryophyllene from the fungus Poronia punctata (Linneus:Fries) Fries. Journal of the Chemical Society,
Perkins Transactions 1, 823-831.
Edwards, R. L. & Whalley, A. J. S. (1979). Meta-bolites of the higher fungi. Part 18. 3-butyl-4-methyl furan-2(5H)-one and 3-butyl-4methy-
lenefuran-2(5H)-one. New y-butyrolactones from the fungus Hypoxylon serpens (Persoon ex Fries) Kickx. Journal of the Chemical
Society, Perkins Transactions 1, 803-806.
Edwards, R. L., Maitland, D. J. & Whalley, A. J.S. (1991). Metabolites of the higher fungi. Part 26. Cubensic acid, 3.7.11.15-tetrahydroxy-18-
(hydromethyl)-2,4,6,10,16,20-heptamethyldocosa-4E,8E,12E,16E tetraenomic acid, a novel polysubstituted C22 fatty acid from the fungus Xylaria cubensis (Mont.) Fr. with substituent and substitution pattern similar to the macrolide antibiotics.Journal of the Chemical Society, Perkins Transactions 1, 1411-1417.
Isaka, M., Jaturapat, A., Kladwang, W., Punya, J.,Lertwerawat, Y., Tanticharoen, N. & Theb-taranonth, Y. (2000). Antiplasmodial
compounds from the wood-decayed fungus Xylaria sp. BCC 1067. Planta Medica, 66(5), 473-475.
Lumyong, S., Lumyong, P. & Hyde, K. D. (2004). Endophytes. In E. B. G. Jones, M.Tantichareon & K. D. Hyde ( E d s . ) , Thai
fungal Diversity (pp. 7-35). Bangkok:BIOTEC.
Mekkamol, S. (1998). Endophytic fungi in Tectona grandis L. (Ph.D. Thesis). Liverpool, UK: Liverpool John Moores University.
Mekkamol, S., Jonglaeka, N., Hywel-Jones, N. L.& Whalley, A. J. S. (1997). Endophytic fungi of teak in Thailand: a preliminary account.
BIOTEC News, 3, pp. 4-5.
Okane, I., Srikitikul, P., Toyama, K., Læssøe, T.,Sivichai, S., Hywel-Jones, N., Nakagiri, A.,Potacharoen, W. & Suzuki, K. L. (2008).
Studies of endophytic Xylariaceae in Thailand:diversity and taxonomy inferred from rDNA sequence analyses with saprobes forming fruit
bodies in the field. Mycoscience, 49, 359-372.
Petrini L. E. & Petrini, O. (1985). Xylariaceous fungi as endophytes. Sydowia, 38, 216-234.
Petrini, O. ( 1991). Fungal endophytes of tree leaves. In: Microbial Ecology of Leaves (eds Andrews, J. H. & Hirano, S. S.). : New York.
Springer-Verlag.
Petrini, O., Petrini, L. E. & Rodrigues, K. F.(1995). Xylariaceous endophytes: an exercise in bio-diversity. Fitopatologia Brasileira, 20, 531-
Petrini, L. E. ( 2013). Rosellinia–a world monograph. Stuttgart: J. Cramer.
Pharamat, T., Palaga, T., Piapukiew, J.,Whalley, A. J. S. & Sihanonth, P. (2013).Antimicrobial and anticancer activities of
endophytic fungi from Mitrajyna javanica Koord and Val. African Journal of Microbiological Research, 7, 5565-5572.
Photita, W., Lumyong, S., Lumyong, P. & Hyde,K. D. (2001). Endophytic fungi of wild banana (Musa acuminata) at Doi Suthep Pui National
Park, Thailand. Mycological Research,105(12), 1508-1513.
Phongpaichit, S., Rungjindamai, N.,Rukachaisirikul V. & Sakayaroj, J. (2006).Antimicrobial activity in cultures of endophytic fungi isolated from Garcinia species. FEMS Immunology and Medical Microbiology, 48, 367-372.
Quang, D. N., Stadler, M., Fournier J., Tomita, A. & Hashimoto, T. (2006). Cohaerins C-F, four azaphilones from the xylariaceous fungus
Annulohypoxylon cohaerens. Tetrahedron, 62,6349-6354.
Rodrigues, K. F. (1994). The foliar fungal endo-phytes of the Amazoniam palm Euterpe oleracea. Mycologia, 86, 376-385.
Rodrigues, K. F. & Samuels, G. J. (1990).Preliminary study of endophytic fungi in a tropical palm. Mycological Research, 94,
-830.
Rodrigues, K. F., Leuchtmann, A. & Petrini, O.(1993). Endophytic species of Xylaria:cultural and isozymic studies. Sydowia, 45,
-138.
Ruchikachorn, N. ( 2005). Endophytic fungi of Cassia fistula L. (Ph. D. Thesis). Liverpool,UK: Liverpool John Moores University.
Singh, S. B., D. Zink, J. Polishook, D. Valentino & Shaffee, A. (1999). Structure and absolute stereochemistry of HIV-1 intergrase inhibitor
integric acid. A novel eremophilanesesqui-terpenoid produced by a Xylaria sp.Tetrahedron Letters, 40(50), 8775-8779.Sodngam, S., Sawadsitang, S., Suwannasai, N. & Mongkolthanaruk, W. (2014). Chemicalconstituents, and their cytotoxicity, of the rare wood decay fungus Xylaria humosa. Natural Products Chemistry, 9, 157-158.
Sopalun, M., Strobel, G. A., Hess, W. M. & Worapong, J. (2003). A record of Muscodor albus, an endophyte from Myristica fragransin
Thailand. Mycotaxon, 88, 239-247.
Stadler, M. & Hellwig, V. (2005). Chemotaxono-my of the Xylariaceae and remarkable bio-active compounds from Xylariales and their
associated asexual stages. Recent ResearchDevelopments in Phytochemistry, 9, 1-120.
Stadler, M., Fournier, J., Gardt, S. & Persoh, D.(2010). The phylogenetic position of Rhopalostroma as inferred from a polythetic
approach. Persoonia, 25, 11-21.
Stadler, M., Fournier, J., Laessøe, L., Lechat, C.,Tichy, H. & Piepenbring, M. (2008).Recognition of hypoxyloid and xylarioid Entonaema species and allied Xylaria species from a comparison of holomorphic morphology, HPLC profiles, and ribosomal DNA sequences. Mycological Progress, 7, 53-73.
Stadler, M., Læssøe, T., Fournier, J., Decock, C., Schmieschek, B., Tichy, H. V. & Persoh, D.(2014). A polyphasic taxonomy of Daldinia
(Xylariaceae). Studies in Mycology, 77, 1-143.
Stadler, M., Wollweber, H., Muhlbauer, A.,Henke, T., Asakawa, Y., Hashimoto, T., Rogers J. D., Ju, Y. M., Wetzstein, H. G. & Tichy, H. V. (2001a). Molecular chemotaxonomy of Daldinia and other Xylariaceae. Mycological Research, 105,1190-1205.
Stadler, M., Wollweber, H., Muhlbauer, A.,Henkel, T., Asakawa, Y., Hashimoto, T., Rogers, J. D., Ju, Y.-M., Wetzstein, H. G. & Tichy, H. V. (2001b). Secondary profiles, genetic fingerprints and taxonomy of Daldinia and allies. Mycotaxon, 77, 379-429.
Stierle, A., Strobel, G. A. & Stierle, D. (1993).Taxol and taxane production by Taxomyces andreanae. Science, 260, 214-216.
Strobel, G. (2010). Muscodor species–endophytes with biological promise.Phytochemistry Reviews, 10, 165-172.
Strobel, G. A., Daisy, B., Castillo, U. & Harper,J. (2004). Natural products from endophytic microorganisms. Journal of Natural Products,
, 257-268.
Suwannarach, N., Bussaban, B., Hyde, K. D. & Lumyong, S. (2010). Muscodorc innamomi, a new endophytic species from Cinnamomum
bejolghota. Mycotaxon, 114, 14-23.
Suwannarach, N., Kumla, J., Bussaban, B., Hyde,K. D., Matsui K. & Lumyong S. (2013).Molecular evidence to support four new
species in the genus Muscodor from northern Thailand. Annals of Microbiology, 63, 1341-1351.
Tenguria, R. K., Khan, F. N. & Quereshi, S.(2011). Endophytesmines of pharmacological therapeutics. World Journal of Science and
Technology, 1, 127-149.
Whalley, A. J. S. (1996). The xylariaceous way of life. Mycological Research, 100, 897-922.
Whalley, A. J. S. & Edwards, R. L. ( 1995).Secondary metabolites and systematic arrangement within the Xylariaceae. Canadian
Journal of Botany, 73(Suppl. 1), S802-S810.
Worapong, J., Strobel, G., Ford, E. J., Li, J. Y.,Baird, G. & Hess, W. H. (2001). Muscodor albus anam. gen. et sp. nov. an endophyte
from Cinnamomum zeylandicum. Mycotaxon,79, 67-79