Endophytic Fungi, Occurrence and Metabolites

  • Daniela Weber
Chapter
Part of the The Mycota book series (MYCOTA, volume 15)

Abstract

The chapter will start with the definition of endophytic fungi, a taxonomic survey and their importance for the host plants. Metabolites of endophytic fungi isolated from various sources including medicinal plants will be summarized. The diversity of the chemical structures and their different biological activities will be discussed. Finally, the ecological role of the endophytic fungi and their metabolites will be reviewed.

References

  1. Abdin MZ, Israr M, Rehman RU, Jain SK (2003) Artemisinin, a novel antimalarial drug: biochemical and molecular approaches for enhanced production. Planta Med 69:289–299PubMedGoogle Scholar
  2. Agusta A, Maehara S, Ohashi K, Simanjuntak P, Shibuya H (2005) Stereoselective oxidation at C-4 of flavans by the endophytic fungus Diaporthe sp. isolated from a tea plant. Chem Pharm Bull 53:1565–1569PubMedGoogle Scholar
  3. Agusta A, Ohashi K, Shibuya H (2006) Bisanthraquinone metabolites produced by the endophytic fungus Diaporthe sp. Chem Pharm Bull 54:579–582PubMedGoogle Scholar
  4. Ahn SH, Mun YJ, Lee SW, Kwak S, Choi MK, Baik SK, Kim YM, Woo WH (2006) Selaginellla tamariscina induces apoptosis via a caspase-3-mediated mechanism in human promyelocytic leukema cells. J Med Food 9:138–144PubMedGoogle Scholar
  5. Aktories K, Förstermann U, Hofmann F, Starke K (2005) Allgemeine und spezielle Pharmakologie und Toxikologie. Elsevier, Urban und Fischer, München JenaGoogle Scholar
  6. Aly AH, Edrada-Ebel R, Indriani ID, Wray V, Müller WEG, Totzke F, Zirrgiebel U, Schächtele C, Kubbutat MHG, Lin WH, Proksch P, Ebel R (2008) Cytotoxic metabolites from the fungal endophyte Alternaria sp. and their subsequent detectionin its host plant. J Nat Prod 71: 972–980PubMedGoogle Scholar
  7. Arechavaleta M, Bacon CW, Hoveland CS, Radcliff DE (1989) Effect of the tall fescue endophyte on plant response to environmental stress. Agron J 81:83–90Google Scholar
  8. Arnold AE, Mejia LC, Kyllo D, Rojas EI, Maynard Z, Robbins N, Herren EA (2003) Fungal endophytes limit pathogen damage in a tropical tree. Ecology 100:15649–15654Google Scholar
  9. Balint GA (2001) Artemisinin and its derivatives; an important new class of antimalarial agents. Pharmacol Ther 90:261–265PubMedGoogle Scholar
  10. Bennett JW, Klich M (2003) Mycotoxins. Clin Microbiol Rev 16:497–516PubMedGoogle Scholar
  11. Bent S, Goldberg H, Padula A, Avins AL (2005) Spontaneous Bleeding associated with Ginkgo biloba: A case report and systematic review of the literatur. J Gen Intern Med 20:657–661PubMedGoogle Scholar
  12. Biswas K, Chattopadhyay I, Banerjee RK, Bandyopadhyay U (2002) Biological activities and medicinal properties of neem (Azadirachata indica). Curr Sci 82:1336–1345Google Scholar
  13. Bonfante P, Perotto S (1995) Strategies of arbuscular mycorrhizal fungi when infecting host plants. New Phytol 130:3–21Google Scholar
  14. Bradshaw AD (1959) Population differentiation in Agrostis tenuis Sibth. II The incidence and significance of infection by Epichloe typhina. New Phytol 58:310–315Google Scholar
  15. Brady SF, Clardy J (2000) CR377, a new pentaketide antifungal agent isolated from an endophytic fungus. J Nat Prod 63:1447–1448PubMedGoogle Scholar
  16. Brady SF, Wagenaar MM, Singh MP, Janso JE, Clardy J (2000a) The cytosporones, new octaketide antibiotics isolated from an endophytic fungus. Org Lett 2:4043–4046Google Scholar
  17. Brady SF, Singh MP, Janso JE, Clardy J (2000b) Cytoskyrins A and B, new BIA active bisanthraquinones isolated from an endophytic fungus. Org Lett 2:4047–4049Google Scholar
  18. Brahmachari G (2004) Neem – an omnipotent plant: a retrospection. Chembiochem 5:408–421PubMedGoogle Scholar
  19. Brown MD (1999) Green tea (Camellia sinensis) extract and its possible role in the prevention of cancer. Altern Med Rev 4:360–370PubMedGoogle Scholar
  20. Busam L, Habermehl GG (1982) Accumulation of mycotoxins by Baccharis coridifolia: A reason of livestock poisoning. Naturwissenschaften 69:392–393PubMedGoogle Scholar
  21. Camarda L, Merlini L, Nasini G (1976) Metabolites of Cercospora taiwapyrone, an α-pyrone of unusual structure from Cercospora taiwanensis. Phytochemistry 15:537–539Google Scholar
  22. Cassady JM, Chan KK, Floss HG, Leistner E (2004) Recent developments in the maytansinoid antitumor agents. Chem Pharm Bull 52:1–26PubMedGoogle Scholar
  23. Chan PC, Xia Q, Fu PP (2007) Ginkgo biloba leave extract: biological, medicinal, and toxicological effects. J Environ Sci Health C Environ Carcinog Ecotoxicol Rev 25:211–244PubMedGoogle Scholar
  24. Chapela IH (1989) Fungi in healthy stems and branches of American beech and aspen: a comparative study. New Phytol 113:65–75Google Scholar
  25. Chapela IH, Boddy L (1988) Fungal colonization of attached beech branches I. Early stages of development of fungal communities. New Phytol 110:39–45Google Scholar
  26. Chapela IH, Petrini O, Hagmann L (1991) Monolignol glucosides as specific recognition messengers in fungal/plant symbiosis. Physiol Mol Plant Pathol 39:289–298Google Scholar
  27. Chapela IH, Petrini O, Biesle G (1993) The physiology of ascospore eclosion in Hypoxylon fragiforme; mechanisms in the early recognition and establishment of an endophytic symbiosis. Mycol Res 97:157–162Google Scholar
  28. Chen LG, Yang LL, Wang CC (2008) Anti-inflammatory activity of mangostins from Garcinia mangostana. Food Chem Toxicol 46:688–693PubMedGoogle Scholar
  29. Cheng XL, Ma SC, Yu JD, Yang SY, Xiao XY, Hu JY, Lu Y, Shaw PC, But PPH, Lin RC (2008) Selaginellin A and B, two novel natural pigments isolated from Selaginella tamariscina. Chem Pharm Bull 56:982–984PubMedGoogle Scholar
  30. Chomcheon P, Sriubolmas N, Wiyakrutta S, Ngamrojanavanich N, Chaicit N, Mahidol C, Ruchirawat S, Kittakoop P (2006) Cyclopentenones, scaffolds for organic syntheses produced by the endophytic fungus mitosporic Dothideomycete sp. LRUB20. J Nat Prod 69:1351–1353Google Scholar
  31. Clavin M, Lorenzen K, Mayer A, Martino V, Anke T (1999) Biological activities in medicinal species of Eupatorium. Acta Hort 501:277–281Google Scholar
  32. Clavin M, Gorzalczany S, Mino J, Kadarian C, Martino V, Ferraro G, Acevedo C (2000a) Antinociceptive effect of some Argentine medicinal species of Eupatorium. Phytother Res 14:275–277Google Scholar
  33. Clavin M, Ferraro G, Coussio J, Martino V, Garcia G, Campos R (2000b) Actividad antiherpetic “in vitro” en extractos de 5 especies de Eupatorium. Anales de Saipa N° 16:131–134Google Scholar
  34. Clay K (1988a) Clavicipitaceous fungal endophytes of grasses: Coevolution and the change from parasitism to mutualism. In: Pirozynski KA, Hawksworth DL (eds) Coevolution of fungi with plants and animals, Academic Press, London. pp 79–105Google Scholar
  35. Clay K (1988b) Fungal endophytes of grasses: a defensive mutualism between plants and fungi. Ecology 69:10–16Google Scholar
  36. Claydon N, Grove JF, Pople M (1985) Elm bark beetle boring and feeding deterrents from Phomopsis oblonga. Phytochemistry 24:937–943Google Scholar
  37. Dahdouh-Guebas F, Collin S, Seen DL, Rönnbäck P, Depommier D, Ravishankar T, Koedam N (2006) Analysing ethnobotanical and fishery-related importance of mangroves of the East-Godavari Delta (Andhhra Pradesh, India) for conservation and management purposes. J Ethnobiol Ethnomed 2:24PubMedGoogle Scholar
  38. Dai J, Krohn K, Flörke U, Draeger S, Schulz B, Kiss-Szikszai A, Antus S, Kurtán T, van Ree T (2006) Metabolites from the endophytic fungus Nodulisporium sp. from Juniperus cedre. Eur J Org Chem 15:3498–3506Google Scholar
  39. Dalsgaard PW, Larsen TO, Christophersen C (2005) Bioactive cyclic peptides from the psychrotolerant fungus Penicillium algidum. J Antibiot 58:141–144PubMedGoogle Scholar
  40. de Bary A (1879) Die Erscheinungen der Symbiose. Verlag von Karl J. Trübner, StrassbourgGoogle Scholar
  41. Descoins C Jr, Bazzocchi IL, Ravelo AG (2002) New sesquiterpenes from Euonymus europaeus (Celastraceae). Chem Pharm Bull 50:199–202PubMedGoogle Scholar
  42. Dikshit A, Naqvi AA, Husain A (1986) Schinus molle, a new source of natural fungitoxicant. Appl Environ Microbiol 51:1085–1088PubMedGoogle Scholar
  43. Ding G, Song YC, Chen JR, Xu C, Ge HM, Wang XT, Tan RX (2006) Chaetoglobosin U, a cytochalasan alkaloid from endophytic Chaetomium globosum IFB-E019. J Nat Prod 69:302–304PubMedGoogle Scholar
  44. Ding G, Liu S, Guo L, Zou Y, Che Y (2008) Antifungal metabolites from the plant endophytic fungus Pestalotiopsis foedan. J Nat Prod 71:615–618PubMedGoogle Scholar
  45. Dong Q, Jao J, Fang JN, Ding K (2007) Structural characterization and immunological activity of two cold-water extractable polysaccharides from Cistanche deserticola Y. C. Ma. Carbohydr Res 342:1343–1349Google Scholar
  46. Dreyfuss MM, Chapela IH (1994) Potential of fungi in the discovery of novel, low-molecular weight pharmaceuticals. In: Gullo VP (ed) The discovery of natural products with therapeuthic potential. Butterworth–Heinemann, London, pp 49–80Google Scholar
  47. Dugoua JJ, Mills E, Perri D, Koren G (2006) Safety and efficacy of Ginkgo (Ginkgo biloba) during pregnancy and lactation. Can J Clin Pharmacol 13:277–284Google Scholar
  48. El-Zayat SA, Nassar MSM, El-Hissy FT, Abdel-Motaal FF, Ito SI (2008) Mycoflora associated with Hyoscyamus muticus growing under an extremely arid desert environment (Aswan region, Egypt). J Basic Microbiol 48:82–92PubMedGoogle Scholar
  49. Endo A, Hasumi K (1997) Mevinic acids. In: Anke T (ed) Fungal biotechnology. Chapman & Hall, London, pp 162–172Google Scholar
  50. Eyberger AL, Dondapati R, Porter JR (2006) Endophyte fungal isolates from Podophyllum peltatum produce podophyllotoxin. J Nat Prod 69:1121–1124PubMedGoogle Scholar
  51. Fang XK, Gao Y, Yang HY, Lang SM, Wang QJ, Yu BY, Zhu DN (2008) Alleviating effects of active fraction of Euonymus alatus abundant in flavonoids on diabetic mice. Am J Chin Med 36:125–140PubMedGoogle Scholar
  52. Filip P, Weber RWS, Sterner O, Anke T (2003) Hormonemate, a new cytotoxic and apoptosis-inducing compound from the endophytic fungus Hormonema dematioides. I. Identification of the producing strain, and isolation and biological properties of hormonemate. Z Naturforsch 58c:547–552Google Scholar
  53. Freeman EM (1902) The seed fungus of Lolium temulentum, L., the Darnel. Philos Trans R Soc London Bio1:1–27Google Scholar
  54. Freeman S, Rodriguez RJ (1993) Genetic conversion of a fungal plant pathogen to a nonpathogenic, endophytic mutualist. Science 260:75–78PubMedGoogle Scholar
  55. Frisvad JC, Larsen TO, Dalsgaard PW, Seifert KA, Louis-Seize G, Lyhne EK, Jarvis BB, Fettinger JC, Overy DP (2006) Four psychrotolerant species with high chemical diversity consistently producing cycloaspeptide A, Penicillium jamesonlandense sp. nov., Penicillim ribium sp. nov., Penicillium soppii and Penicillium lanosum. Int J Syst Evol Microbiol 56:1427–1437PubMedGoogle Scholar
  56. Ge HM, Shen Y, Zhu HC, Tan SH, Ding H, Song YS, Tan RX (2008) Penicidones A-C, three cytotoxic alkaloidal metabolites of an endophytic Penicillium sp. Phytochemistry 69:571–576PubMedGoogle Scholar
  57. Gianotti RL, Bomblies A, Dafalla M, Issa-Arzika I, Duchemin JB, Eltahir EAB (2008) Efficacy of local neem exracts for sustainable malaria vector control in an African village. Malar J 7:138–148PubMedGoogle Scholar
  58. Girault L (1987) Kallawaya. Curanderos itinerantes de los Andes. Unicef/OPS/OMS, La Paz, p. 462Google Scholar
  59. Gond SK, Verma VC, Kumar A, Kumar V, Kharwar RN (2007) Study of endophytic fungal community from different parts of Aegle marmelos Correae (Rutaceae) from Varanasi (India). World J Microbiol Biotechnol 23:1371–1375Google Scholar
  60. Govindachari TR, Ravindranath KR, Viswanathan N (1974) Mappicine, a minor alkaloid from Mappia foetida Miers. J Chem Soc Perkin Trans I 11:2215–1217Google Scholar
  61. Grove JF, Pople M (1979) Metabolic products of Fusarium lavarum Fuckel. The fusarentins and the absolute configuration of moncerin. J. C. S. Perkin 1:2048–2051Google Scholar
  62. Gu W, Ge M, Song YM, Ding H, Zhu HL, Zhao XA, Tan RX (2007) Cytotoxic benzo[j]fluoranthene metabolites from Hypoxylon truncatum IFB-18, an endophyte of Artemisia annua. J Nat Prod 70:114–117PubMedGoogle Scholar
  63. Gunatilaka AAL (2006) Natural products from plant-associated microorganisms: Distribution, structural diversity, bioactivity, and implications of their occurence. J Nat Prod 69:509–526PubMedGoogle Scholar
  64. Hamilton-Miller JMT (1995) Antimicrobial properties of tea (Camellia sinensis L.). Antimicrob Agents Chemother 39:2375–2377PubMedGoogle Scholar
  65. Hamilton-Miller JMT (2001) Anti-carciogenic properties of tea (Camellia sinensis). J Med Microbiol 50:299–302PubMedGoogle Scholar
  66. Hashida C, Tanaka N, Kashiwada Y, Ogawa M, Takaishi Y (2008) Prenylated chloroglucinol derivates from Hypericum perforatum var. angustifolium. Chem Pharm Bull 56:1164–1167PubMedGoogle Scholar
  67. Hawksworth DL (2001) The magnitude of fungal diversity: the 1.5 million species estimated revisited. Mycol Res 105:1422–1432Google Scholar
  68. Hayashi A, Fujioka S, Nukina M, Kawano T, Shimada A, Kimura Y (2007) Fumiquinones A and B, nematicidal quinones produced by Aspergillus fumigatus. Biosci Biotechnol Biochem 71:1697–1702PubMedGoogle Scholar
  69. Hellwig V, Grothe T, Mayer-Bartschmid A, Endermann R, Geschke FU, Henkel T, Stadler M (2002) Altersetin, a new antibiotic from cultures of endophytic Alternaria spp. Taxonomy, fermentation, isolation, structure elucidation and biologic activities. J Antibiot 55:881–892PubMedGoogle Scholar
  70. Hill NS, Belesky DP, Stringer WC (1991) Competitiveness of tall fescue as influenced by Acremonium coenophialum. Crop Sci 31:185–190Google Scholar
  71. Hu HJ, Wang KW, Wu B, Sun CR, Pan YJ (2005) Chemical shift assignments of two oleanane triterpenes from Euronymus hederaceus. J Zhejiang Univ Sci B 6:719–721PubMedGoogle Scholar
  72. Huang WY, Cai YZ, Hyde KD, Corke H, Sun MEI (2007) Endophytic fungi from Nerium oleander L (Apocynaceae): main constituents and antioxidant activity. World J Microbiol Biotechnol 23:1253–1263Google Scholar
  73. Iharlegui L, Hurrel J (1992) Asteraceae de interes ethnobotanico de los departamentos de Santa Victoria e Iruya (Salta, Argentinien). Ecognicion 3:3–18Google Scholar
  74. Isaka M, Jaturapat A, Rukseree K, Danwisetkanjana K, Tanticharoen M, Thebtaranonth Y (2001) Phomaxanthones A and B, novel xanthone dimers from the endophytic fungus Phomopsis species. J Nat Prod 64:1015–1018PubMedGoogle Scholar
  75. Ismail IS, Ito H, Mukainaka T, Higashihara H, Enja F, Tokuda H, Nishina H, Yoshida T (2003) Ichthyotoxic and anticarcinogenic effects of triterpenoids from Sandoricum koetjape Bark. Biol Pharm Bull 26:1351–1353PubMedGoogle Scholar
  76. Ismail IS, Ito H, Hatano T, Taniguchi S, Yoshida T (2004) Two new analogues of trijugin-type limonoids from the leaves of Sandoricum koetjape. Chem Pharm Bull 52:1145–1147PubMedGoogle Scholar
  77. Jennewein S, Croteau R (2001) Taxol: biosynthesis, molecular genetics, and biotechnological applications. Appl Microbiol Biotechnol 57:13–19PubMedGoogle Scholar
  78. Jiang Y, Tu PF (2009) Analysis of chemical constituents in Cistanche species. J Chromatogr A 1216:1970–1979PubMedGoogle Scholar
  79. Johnston D, Couché E, Edmonds DJ, Muir KW, Procter DJ (2003) The first synthetic studies on pestalotiopsis A. A stereocontrolled approach to the functionalised bicyclic core. Org Biol Chem 1:328–337Google Scholar
  80. Kackley KE, Grybauskas AP, Dernoeden PH, Hill RL (1990) Role of drought stress in the development of summer patch in field-inoculated Kentucky bluegrass. Phytopathology 80:665–658Google Scholar
  81. Kang DG, Yin MH, Oh H, Lee DH, Lee HS (2004) Vasorelaxation by amentoflavone isolated from Selaginella tamariscina. Planta Med 70:718–722PubMedGoogle Scholar
  82. Kim CH, Kim DI, Kwon CN, Kang SK, Jin UH, Suh SJ, Lee TK, Lee IS (2006) Euonymus alatus (Thunb.) Sieb induces apoptosis via mitochondrial pathway as prooxidant in human uterine leiomyomal smooth muscle cells. Int J Gynecol Cancer 16:843–848PubMedGoogle Scholar
  83. Kimmons CA, Gwinn KD, Bernard EC (1990) Nematode reproduction on endophyte-infected and endophyte-free tall fescue. Plant Dis 74:757–761Google Scholar
  84. Krohn K, Ullah Z, Hussain H, Flörke U, Schulz B, Draeger S, Pescitelli G, Salvadori P, Antus S, Kurtán T (2007a) Massarilactones E-G, new metabolites from the endophytic fungus Coniothyrium sp., associated with the plant Artemisia maritima. Chirality 19:464–470Google Scholar
  85. Krohn K, Kock I, Elsässer B, Flörke U, Schulz B, Draeger S, Pescitelli G, Antus S, Kurtán T (2007b) Bioactive natural products from the endophyic fungus Ascochyta sp. from Meliotus dentatus – configurational assignment by solid-state CD and TDDFT calculations. Eur J Org Chem 7:1123–1129Google Scholar
  86. Kucht S, Groß J, Hussein Y, Grothe T, Keller U, Basar S, König WA, Steiner U, Leistner E (2004) Elimination of ergoline alkaloids following treatment of Ipomoea asarifolia (Convolvulaceae) with fungicides. Planta 219:619–625PubMedGoogle Scholar
  87. Kumar DS, Hyde KD (2004) Biodiversity and tissue-recurrence of endophytic fungi in Tripterygium wilfordii. Fungal Divers 17:69–90Google Scholar
  88. Kusari S, Lamshöft M, Zühlke S, Spiteller M (2008) An endophytic fungus from Hypericum perforatum that produces hypericin. J Nat Prod 71:159–162PubMedGoogle Scholar
  89. Lambert JD, Yang CS (2003) Mechanisms of cancer prevenion by tea constituents. J Nutr 133:3262–3267Google Scholar
  90. Langford SD, Boor PJ (1996) Oleander toxicity: an examination of human and animal toxic exposures. Toxicology 3:1–13Google Scholar
  91. Li E, Tian R, Liu S, Chen X, Guo L, Che Y (2008) Pestalotheols A-D, bioactive metabolites from the plant endophytic fungus Pestalotiopsis theae. J Nat Prod 71:664–668PubMedGoogle Scholar
  92. Li H, Qing C, Zhang Y, Zhao Z (2005) Screening for endophytic fungi with antitumour and antifungal activities from Chinese medicinal plants. World J Microbiol Biotechnol 21:1515–1519Google Scholar
  93. Lin X, Lu C, Huang Y, Zheng Z, Su W, Shen Y (2007) Endophytic fungi from a pharmaceutical plant, Camptotheca acuminata: isolation, identification and bioactivity. Worl J Microbiol Biotechnol 23:1037–1040Google Scholar
  94. Lin ZJ, Lu ZY, Zhu TJ, Fang YC, Gu QQ, Zhu WM (2008a) Penicillenols from Penicillium sp. GQ-7, an endophytic fungus associated with Aegiceras corniculatum. Chem Pharm Bull 56:217–221Google Scholar
  95. Lin ZJ, Wen JG, Zhu TJ, Fang YC, Gu QQ, Zhu WM (2008b) Chrysogenamide A from an endophytic fungus associated with Cistanche deserticola and its neuroprotective effect on SH-SY5Y cells. J Antibiot 61:81–85Google Scholar
  96. Liu JY, Liu CH, Zou WX, Tan RX (2003) Leptosphaeric acid, a metabolite with a novel carbon skeleton from Leptosphaeria sp. IV403, an endophytic fungus in Artemisia annua. Helv Chim Acta 86:657–660Google Scholar
  97. Liu X, Dong M, Chen X, Jiang M, Lv X, Zou J (2008) Antimicrobial activity of an endophytic Xylaria sp. YX-28 and identification of its antimicrobial compound 7-amino-4-methylcoumarin. Appl Microbiol Biotechnol 78:241–247PubMedGoogle Scholar
  98. Lu YH, Liu ZY, Wang ZT, Wei DZ (2006) Quality evaluation of Platycladus orientalis (L.) Franco through simultaneous determination of four bioactive flavonoids by high-performance liquid chromatography. J Pharm Biomed Anal 41:1186–1190PubMedGoogle Scholar
  99. Luper S (1999) A review of plants used in the treatment of liver disease: part two. Altern Med Rev 4:178–188PubMedGoogle Scholar
  100. Ma LY, Ma SC, Wei F, Lin RC, But PPH, Lee SHS, Lee SF (2003) Uncinoside A and B, two new antiviral chormone glycosides from Selaginalla uncinata. Chem Pharm Bull 51:1264–1267PubMedGoogle Scholar
  101. Magnani RF, Rodigues-Fo E, Daolio C, Ferreira AG, de Souza AQL (2003) Three highly oxygenated caryophyllene sequiterpenes from Pestalotiopsis sp., a fungus isolated from bark of Pinus taeda. Z Naturforsch 58c:319–324Google Scholar
  102. Maloney N, Hao W, Xu J, Gibbons J, Hucul J, Roll D, Brady SF, Schroeder FC, Clardy J (2006) Phaeosphaeride A, an inhibitor o STAT3-dependent signalling isolated from an endophytic fungus. Org Lett 8:4067–4070PubMedGoogle Scholar
  103. Meister J, Weber D, Martino V, Sterner O, Anke T (2007) Phomopsidone, a novel depsidone from an endophyte of the medicinal plant Eupatorium arnottianum. Z Naturforsch C 62:11–15PubMedGoogle Scholar
  104. Meng LH, Liao ZY, Pommier Y (2003) Non-camptothecin DNA topoisomerase I inhibitors in cancer therapy. Curr Top Med Chem 3:305–320PubMedGoogle Scholar
  105. Miller AL (1998a) St. John's wort (Hypericum perforatum): clinical effects on depression and other conditions. Altern Med Rev 3:18–26Google Scholar
  106. Miller AL (1998b) Botanical influences on cardiovascular disease. Altern Med Rev 3:422–431Google Scholar
  107. Miño J, Gorzalczany S, Moscatelli V, Ferraro G, Acevedo C, Hnatyszyn O (2002) Actividad antinociceptiva y antinflamatoria de Erythrina crista-galli (Ceibo). Acta Farm Bonaerense 21:93–98Google Scholar
  108. Mitscher LA, Gollapudi RSR, Gerlach DC, Drake SD, Veliz EA, Ward JA (1988) Erycristin, a new antimicrobial petrocarpan from Erythrina crista-galli. Phytochemistry 27:381–385Google Scholar
  109. Nalini MS, Madesh B, Tejesvi MV, Prakash HS, Subbaiah V, Kini KR, Shetty HS (2005) Fungal endophytes from the three-leaved caper, Crataeva magna (Lour.) DC. (Capparidaceae). Mycopathologia 159:245–249PubMedGoogle Scholar
  110. Nebenführ A, Ritzenthaler C, Robinson DG (2002) Brefeldin A: deciphering an enigmatic inhibitor of secretion. Plant Physiology 130:1102–1108PubMedGoogle Scholar
  111. Nishikawa W (1933) A metabolic product of Aspergillus melleus Yukawa. J Agric Chem Soc Japan Chem 9:772Google Scholar
  112. Oberlies NH, Kroll DJ (2004) Camptothecin and taxol: historic achievements in natural product research. J Nat Prod 67:129–135PubMedGoogle Scholar
  113. Park SH, Ko SK, Chung SH (2005) Euronymus alatus prevents the hyperglycemia and hyperlipidemia induced by high-fat diet in ICR mice. J Ethnopharmacol 102:326–335PubMedGoogle Scholar
  114. Parker EJ, Scott DB (2004) Indole-diterpene biosynthesis in ascomycetous fungi. In: An Z (ed) Handbook of industrial mycology. Dekker, New York, pp 405–426Google Scholar
  115. Pedraza-Chaverri J, Cárdenas-Rodríguez N, Orozo-Ibarra M, Pérez-Rojas JM (2008) Medicinal properties of mangosteen (Garcinia mangostana). Food Chem Toxicol 46:3227–3239PubMedGoogle Scholar
  116. Penna C, Marino S, Gutkind G, Clavin M, Ferraro G, Martino V (1997) Antimicrobial activity of Eupatorium species growing in Argentina. J Herbs Spices Med Plants 5:21–28Google Scholar
  117. Petrini O (1996) Ecological and physiological aspects of host-specificity in endophytic fungi. In: Redlin SC, Carris LM (eds) Endophytic funig in grasses and woody plants. Systematics, ecology, and evolution. APS, St Paul, pp 87–100Google Scholar
  118. Petrini O, Petrini LE, Rodrigues KF (1995) Xylariaceous endophytes: an exercise in biodiversity. Fitopatol Bras 20:531–539Google Scholar
  119. Pirozynski KA, Hawksworth DL (1988) Coevolution of fungi with plants and animals: Introduction and overview. In: Pirozynski KA, Hawksworth DL (eds.) Coevolution of Fungi with Plants and Animals. Academic Press, London, pp 1–29Google Scholar
  120. Pirozynski KA, Malloch DW (1975) The origin of plants: a matter of mycotrophism. Biosystems 6:153–164PubMedGoogle Scholar
  121. Poch GK, Gloer JB, Shearer CA (1992) New bioactive metabolites from a freshwater isolate of the fungus Kirschsteiniothelia sp. J Nat Prod 55:1093–1099PubMedGoogle Scholar
  122. Pongcharoen W, Rukachaisirikul V, Phongpaichit S, Sakayaroj J (2007) A new didydrobenzofuran derivative from the endophytic fungus Botryosphaeria mamane PSU-M76. Chem Pharm Bull 55:1404–1405PubMedGoogle Scholar
  123. Pornpakakul S, Liangsakul J, Ngamrojanavanich N, Roengsumran S, Sihanonth P, Piapukiew J, Sangvichien E, Puthong S, Petsom A (2006) Cytotoxic activity of four xanthones from Emericella variecolor, an endophytic fungus isolated from Croton oblongifolius. Arch Pharm Res 29:140–144PubMedGoogle Scholar
  124. Pulici M, Sugawara F, Koshino H, Uzawa J, Yoshida S (1996) Pestalotiopsins A and B: new caryophyllenes from an endophytic fungus of Taxus brevifolia. J Org Chem 61:2122–2124Google Scholar
  125. Pulici M, Sugawara F, Koshino H, Okada G, Esumi Y, Uzawa J, Yoshida S (1997) Metabolites of Pestalotiopsis spp., endophytic fungi of Taxis brevifolia. Phytochemistry 46:313–319Google Scholar
  126. Puri SC, Verma V, Amna T, Qazi GN, Spiteller M (2005) An endophytic fungus from Nothapodytes foedida that produces camptothecin. J Nat Prod 68:1717–1719PubMedGoogle Scholar
  127. Puri SC, Nazir A, Chawia R, Arora R, Riyaz-ul-Hasan S, Amna T, Ahmed B, Verma V, Singh S, Sagar R, Sharma A, Kumar R, Sharma RK, Oazi GN (2006) The endophytic fungus Trametes hirsuta as a novel alternative source of podophyllotoxin and related aryl tetralin lignans. J Biotechnol 122:494–510PubMedGoogle Scholar
  128. Quiroga EN, Sampietro AR, Vattuone MA (2001) Screening antifungal activities of selected medicinal plants. J Ethnopharmacol 74:89–96PubMedGoogle Scholar
  129. Rasadah MA, Khozirah S, Aznie AA, Nik MM (2004) Anti-inflammatory agents from Sandoricum koetjape Merr. Phytomedicine 11:262–263Google Scholar
  130. Raviraja NS (2005) Fungal endophytes in five medicinal plant species from Kudremukh Range, Western Ghats of India. J Basic Microbiol 45:230–235PubMedGoogle Scholar
  131. Read JC, Camp BJ (1986) The effect of fungal endophyte Acremonium coenophialum in tall fescue on animal performance, toxicity, and stand maintenance. Agron J 78:848–850Google Scholar
  132. Ren Y, Strobel GA, Graff JC, Jutila M, Park SG, Gosh S, Teplow D, Condrom M, Pang E, Hess WM, Moore E (2008) Colutellin A, an immunosuppressive peptide from Colletotrichum dematium. Microbiology 154:1973–1979PubMedGoogle Scholar
  133. Rizzo I, Varsavky E, Haidukowski M, Frade H (1997) Macrocyclic trichothecenes in Baccharis coridifolia plants and endophytes and Baccharis artemisioides plants. Toxicon 35:753–757PubMedGoogle Scholar
  134. Rogers JD (1979) The Xylariaceae: Systematic, biological and evolutionary aspects. Mycologia 71:1–42Google Scholar
  135. Roome T, Dar A, Ali S, Naqvi S, Choudhary MI (2008) A study on antioxidant, free radical scavenging, anti-inflammatory and hepatoprotective actions of Aegiceras corniculatum (stem) extracts. J Ethnopharmacol 13:514–521Google Scholar
  136. Roth L, Daunderer M, Kormann K (1994) Giftpflanzen Pflanzengifte. Nikol, HamburgGoogle Scholar
  137. Rukachaisirikul V, Kaeobamrung J, Panwiriyarat W, Saitai P, Sukpondma Y, Phongpaichit S, Sakayaroj J (2007) A new pyrone derivative from the endophytic fungus Penicillium paxilli PSU-A71. Chem Pharm Bull 55:1383–1384PubMedGoogle Scholar
  138. Saikkonen K, Faeth SH, Helander M, Sullivan TJ (1998) Fungal endophytes: a continuum of interactions with host plants. Annu Rev Ecol Syst 29:319–343Google Scholar
  139. Schardl CL, Blankenship JD, Spiering MJ, Machado C (2004) Loline and ergot alkaloids in grass endophytes. In: An Z (ed) Handbook of industrial mycology. Dekker, New York, pp 427–448Google Scholar
  140. Schardl CL, Panaccione DG, Tudzynski P (2006) Ergot alkaloids – biology and molecular biology. Alkaloids 63:47–88Google Scholar
  141. Schmeda-Hirschmann G, Hormazabal E, Astudillo L, Rodriguez J, Theoduloz C (2005) Secondary metabolites from endophytic fungi isolated from the Chilean gymnosperm Prumnopitys andina (Lleuque). World J Microbiol Biotechnol 21:27–32Google Scholar
  142. Schmeda-Hirschmann G, Hormazabal E, Rodriguez JA, Theoduloz C (2008) Cycloaspeptide A and pseurotin A from the endophytic fungus Penicillium janczewskii. Z Naturforsch 63c:383–388Google Scholar
  143. Seto Y, Takahashi K, Matsuura H, Kogami Y, Yada H, Yoshihara T, Nabeta K (2007) Novel cyclic peptide, epichlicin, from the endophytic fungus, Epichloe typhina. Biosci Biotechnol Biochem 71:1470–1475PubMedGoogle Scholar
  144. Seymour FA, Cresswell JE, Fisher PJ, Lappin-Scott HM, Haag H, Talbot NJ (2004) The influence of genotypic variation of two endophytic fungal species. Fungal Genet Biol 41:721–734PubMedGoogle Scholar
  145. Shiono Y, Muranyama T (2005) New eremophilane-type sequiterpenoids, eremoxylarins A and B from xylariaceous endophytic fugus YUA-026. Z Naturforsch 60b:885–890Google Scholar
  146. Shiono Y, Tsuchinari M, Shimanuki K, Miyajima T, Murayama T, Koseki T, Laatsch H, Funakoshi T, Takanami K, Suzuki K (2007) Fusaristatins A and B, two new cyclic lipopeptides from an endophytic Fusarium sp. J Antibiot 60:309–316PubMedGoogle Scholar
  147. Silberstein SD, McCrory DC (2003) Ergotamine and dihydroergotamine: history, pharmacology, and efficacy. Headache 43:411–166Google Scholar
  148. Silva GH, Teles HL, Zanardi LM, Marx Young MC, Eberlin MN, Hadad R, Pfenning LH, Costa-Neto CM, Castro-Gamboa I, da Silva Bolzani V, Araújo AR (2006) Cadinane sesquiterpenoids of Phomopsis cassiae an endophytic fungus associated with Cassia spectabilis (Leguminosae). Phytochemistry 67:1964–1969PubMedGoogle Scholar
  149. Sinclair JB, Cerkauskas RF (1996) Latent infection vs endophytic colonization by fungi. In: Redlin SC, Carris LM (eds) Endophytic fungi in grasses and woody plants. systematics, ecology, and evolution. APS, St. Paul, pp 3–29Google Scholar
  150. Soliman HSM, Simon A, Toth G, Duddeck H (2001) Identification and structure determination of four triterpene saponins from some Middle-East plants. Magn Reson Chem 39:567–576Google Scholar
  151. Stierle A, Strobel G, Stierle D (1993) Taxol and taxane production by Taxomyces andreanae, an endophytic fungus of pazific yew. Science 260:214–216PubMedGoogle Scholar
  152. Stone JK, Bacon CW, White JF Jr (2000) An overview of endophytic microbes: endophytism defined. In: Bacon CW, White JF (eds) Microbial endophytes. Dekker, New York, pp 389–420Google Scholar
  153. Strobel G (2003) Endophytes as sources of bioactive products. Microbes Infect 5:535–544PubMedGoogle Scholar
  154. Strobel G, Ford E, Worapong J, Harper JK, Arif AM, Grant DM, Fung PCW, Chau RMW (2002) Isopestacin, an isobenzofuranone from Pestalotiopsis microspora, possessing antifungal and antioxidant activities. Phytochemistry 60:179–183PubMedGoogle Scholar
  155. Strobel G, Daisy B, Castillo U, Harper J (2004) Natural products from endophytic microorganisms. J Nat Prod 67:257–268PubMedGoogle Scholar
  156. Suksamrarn S, Suwannapoch N, Phakhodee W, Thanuhiranlert J, Ratananukul P, Chimnoi N, Suksamrarn A (2003) Antimycobacterial activity of prenylated xanthones from the fruits of Garcinia mangostana. Chem Pharm Bull 51:857–859PubMedGoogle Scholar
  157. Takeuchi N, Goto K, Sasaki Y, Fujeta T, Okazaki K, Kamata K, Tobinaga S (1992) Synthesis of (+)- and (−)-mellein utilizing an annelation reaction of isoxazoles with dimethyl-3-oxoglutarate. Heterocycles 33:357–374Google Scholar
  158. Tan Q, Yan X, Lin X, Huang Y, Zheng Z, Song S, Lu C, Shen Y (2007) Chemical constituents of the endophytic fungal strain Phomopsis sp. NXZ-05 of Camptotheca acuminata. Helv Chim Acta 90:1811–1817Google Scholar
  159. Tan RX, Zou WX (2001) Endophytes: a rich source of functional metabolites. Nat Prod Rep 18:448–459PubMedGoogle Scholar
  160. Tan RX, Zheng WF, Tang HQ (1998) Biologically active substances from the genus Artemisia. Planta Med 64:295–302PubMedGoogle Scholar
  161. Tansuwan S, Pornpakakul S, Roengsumran S, Petsom A, Muangsin N, Sihanonta P, Chaichit N (2007) Antimalarial benzoquinones from an endophytic fungus Xylaria sp. J Nat Prod 70:1620–1623PubMedGoogle Scholar
  162. Tejesvi MV, Madesh B, Nalini MS, Prakash HS, Kini KR, Subbiah V, Shetty HS (2005) Endophytic fungal assemblages from inner bark and twig of Terminalia arjuna W. & A. (Combretaceae). World J Microbiol Biotechnol 21:1535–1540Google Scholar
  163. Toursarkissian M (1980) Plantas Medicinales de la Argentina. Hemisferio Sur, Buenos Aires, p. 70Google Scholar
  164. Uecker FA (1988) A world list of Phomopsis names with notes on nomenclature, morphology and biology. Cramer, BerlinGoogle Scholar
  165. van Eijik GW, Royemans HJ (1978) Naphthoquinone derivatives from the fungus Hendersonula toruloidea. Experientia 34:1257–1258Google Scholar
  166. Viegas C Jr, Alexandre-Moreira MS, Fraga CAM, Barreiro EJ, da Silva Bolzani V, de Miranda ALP (2008) Antinociceptive profile of 2,3,6-trisubstituted piperidine alkaloids: 3-O-acetyl-spectaline and semi-synthetic derivatives of (−)-spectaline. Chem Pharm Bull 56:407–412PubMedGoogle Scholar
  167. Vogl AE (1898) Mehl und die anderen Mehlprodukte der Cerealien und Leguminosen. Nahrungsm Unters Hyg Warenk 12:25–29Google Scholar
  168. Wagennaar MM, Clardy J (2001) Dicerandrols, new antibiotic and cytotoxic dimers produced by the fungus Phomopsis longicolla isolated from an endangered mint. J Nat Prod 64:1006–1009Google Scholar
  169. Walker K, Croteau R (2001) Molecules of interest. Taxol biosynthetic genes. Phytochemistry 58:1–7PubMedGoogle Scholar
  170. Wall ME, Wani MC, Cook CE, Palmer KH, McPhail AT, Sim GA (1966) Plant antitumor agents. I The isolation and structure of camptothecin, a novel alkaloid leukemia and tumor inhibitor from Camptotheca acuminata. J Am Chem Soc 88:3888–3890Google Scholar
  171. Wallner BM, Booth NH, Robbins JD, Bacon CW, Porter JK, Kiser TE, Wilson RW, Johnson B (1983) Effect of an endophytic fungus isolated from toxic pasture grass on serum prolactin concentrations in the lactation cow. Am J Vet Res 44:1317–1322PubMedGoogle Scholar
  172. Wang C, Wu J, Mei X (2001) Enhancement of taxol production and excretion in Taxus chinensis cell culture by fungal elicitation and medium renewal. Appl Microbiol Biotechnol 55:404–410PubMedGoogle Scholar
  173. Wani MC, Taylor HL, Wall ME, Coggon P, McPhail AT (1971) Plant antitumor agents. VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. J Am Chem Soc 93:2325–2327PubMedGoogle Scholar
  174. Webber J (1981) A natural biological control of dutch elm disease. Nature 292:449–451Google Scholar
  175. Weber D (2006) Biologisch aktive Metabolite endophytischer Pilze argentinischer Medizinalpflanzen und anderer Pilze. Dissertation, University of KaiserslauternGoogle Scholar
  176. Weber D, Sterner O, Anke T, Gorzalczancy S, Martino V, Acevedo C (2004) Phomol, a new antiinflammatory metabolite from an endophyte of the medicinal plant Erythrina crista-galli. J Antibiot 57:559–563PubMedGoogle Scholar
  177. Weber D, Gorzalczany S, Martino V, Acevedo C, Sterner O, Anke T (2005) Metabolites from endophytes of the medicinal plant Erythrina crista-galli. Z Naturforsch C 60:467–477PubMedGoogle Scholar
  178. Weber RWS, Anke H (2006) Effects of endophytes on colonisation by leaf surface microbiota. In: Bailey MS, Lilley AK, Timms-Wilson TM, Spencer-Phillips PT (eds) Microbial ecology of plant surfaces. CABI, WallingfordGoogle Scholar
  179. Weber RWS, Stenger E, Meffert A, Hahn M (2004) Brefeldin A productiuon by Phoma medicaginis in dead pre-colonized plant tissue: a strategy for habitat conquest? Mycol Res 108:662–671PubMedGoogle Scholar
  180. Webster J, Weber RWS (2004) Teaching techniques for mycology: 23. Eclosion of Hypoxylon fragiforme ascospores as a prelude to germination. Mycologist 18:170–173Google Scholar
  181. Wenke J (1993) Isolierung und Charakterisierung neuer Inhibitoren der Chitinsynthase aus höheren Pilzen. Dissertation, University of KaiserslauternGoogle Scholar
  182. West CP, Izekor E, Turner KE, Elmi AA (1993) Endophytes effects on growth and persistence of tall fescue along a water-supply gradient. Agron J 85:264–270Google Scholar
  183. Whalley AJS (1996) The xylariaceous way of life. Mycol Res 100:897–922Google Scholar
  184. White JF Jr, Cole GT (1985) Endophyte–host associations in forage grasses. III. In vitro inhibition of fungi by Acremonium coenophialum. Mycologia 77:487–489Google Scholar
  185. White JF Jr, Reddy PV, Bacon CW (2000) Biotrophic endophytes of grasses: A systematic appraisal. In: Bacon CW, White JF (eds) Microbial endophytes. Dekker, New York, pp 49–62Google Scholar
  186. Wijeratne EMK, Paranagama PA, Marron MT, Gunatilaka MK, Arnold AE, Gunatilaka AAL (2008) Sesquiterpene quinines and related metabolites from Phyllosticta spinarum, a fungal strain endophytic in Platycladus orientalis of the Sonoran Dessert. J Nat Prod 71:218–222PubMedGoogle Scholar
  187. Wilson D (2000) Ecology of woody plant endopyhtes. In: Bacon CW, White JF (eds) Microbial endophytes. Dekker, New York, pp 389–420Google Scholar
  188. Wiyakrutta S, Sriubolmas N, Panphut W, Thongon N, Danwiset-kanjana K, Ruangrungsi N, Meevootisom V (2004) Endophytic fungi with anti-microbial, anti-cancer and anti-malarial activities isolated from Thai medicinal plants. World J Microbiol Biotechnol 20:265–272Google Scholar
  189. Woerdenbag HJ, Lugt CB, Pras N (1990) Artemisia annua L.: a source of novel antimalarial drugs. Pharm Weekbl Sci 19:169–181Google Scholar
  190. Wu SH, Chen YW, Shao SC, Wang LD, Li ZY, Yang LY, Li SL, Huang R (2008) Ten-membered lactones from Phomopsis sp, an endophytic fungus of Azadirachta indica. J Nat Prod 71:731–734PubMedGoogle Scholar
  191. Xu F, Zhang Y, Wang J, Pang J, Huang C, Wu X, She Z, Vrijmoed LLP, Jones EBG, Lin Y (2008) Benzofuran derivatives from the mangrove endophytic fungus Xylaria sp. (#2508). J Nat Prod 71:1251–1253PubMedGoogle Scholar
  192. Yang SF, Prabhu S, Landau J (2001) Prevention of carcinogenesis by tea phenols. Drug Metab Rev 33:237–253PubMedGoogle Scholar
  193. Yang SF, Chu SC, Liu SJ, Chen YC, Chang YZ, Hsieh YS (2007) Antimetastatic activities of Salaginella tamariscina (Beauv.) on lung cancer cells in vitro and in vivo. J Ethnopharmacol 110:483–489PubMedGoogle Scholar
  194. Yshihara T, Togiya S, Koshino H, Sakamura S, Shimanuki T, Sato T, Tajimi A (1985) Three fungitoxic sesquiterpenes from stromata of Epichloe typhina. Tetrahedron Lett 26:5551–5554Google Scholar
  195. Zou WX, Meng JC, Lu H, Chen GX, Shi GX, Zhang TY, Tan RX (2000) Metabolites of Colletotrichum gloeosporioides, an endophytic fungus in Artemisia mongolica. J Nat Prod 63:1529–1530PubMedGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2009

Authors and Affiliations

  • Daniela Weber
    • 1
    • 2
  1. 1.Institute of Biotechnology and Drug ResearchKaiserslauternGermany
  2. 2.MIP International Pharma Research GmbHSt. IngbertGermany

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