Skip to main content

Endophytic Fungi, Occurrence and Metabolites

  • Chapter
  • First Online:
Physiology and Genetics

Part of the book series: The Mycota ((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.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 229.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  • Abdin MZ, Israr M, Rehman RU, Jain SK (2003) Artemisinin, a novel antimalarial drug: biochemical and molecular approaches for enhanced production. Planta Med 69:289–299

    CAS  PubMed  Google Scholar 

  • 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 53:1565–1569

    CAS  PubMed  Google Scholar 

  • Agusta A, Ohashi K, Shibuya H (2006) Bisanthraquinone metabolites produced by the endophytic fungus Diaporthe sp. Chem Pharm Bull 54:579–582

    CAS  PubMed  Google Scholar 

  • 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 9:138–144

    PubMed  Google Scholar 

  • Aktories K, Förstermann U, Hofmann F, Starke K (2005) Allgemeine und spezielle Pharmakologie und Toxikologie. Elsevier, Urban und Fischer, München Jena

    Google Scholar 

  • 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: 972–980

    CAS  PubMed  Google Scholar 

  • Arechavaleta M, Bacon CW, Hoveland CS, Radcliff DE (1989) Effect of the tall fescue endophyte on plant response to environmental stress. Agron J 81:83–90

    Google Scholar 

  • 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 100:15649–15654

    CAS  Google Scholar 

  • Balint GA (2001) Artemisinin and its derivatives; an important new class of antimalarial agents. Pharmacol Ther 90:261–265

    CAS  PubMed  Google Scholar 

  • Bennett JW, Klich M (2003) Mycotoxins. Clin Microbiol Rev 16:497–516

    CAS  PubMed  Google Scholar 

  • 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 20:657–661

    PubMed  Google Scholar 

  • Biswas K, Chattopadhyay I, Banerjee RK, Bandyopadhyay U (2002) Biological activities and medicinal properties of neem (Azadirachata indica). Curr Sci 82:1336–1345

    CAS  Google Scholar 

  • Bonfante P, Perotto S (1995) Strategies of arbuscular mycorrhizal fungi when infecting host plants. New Phytol 130:3–21

    Google Scholar 

  • Bradshaw AD (1959) Population differentiation in Agrostis tenuis Sibth. II The incidence and significance of infection by Epichloe typhina. New Phytol 58:310–315

    Google Scholar 

  • Brady SF, Clardy J (2000) CR377, a new pentaketide antifungal agent isolated from an endophytic fungus. J Nat Prod 63:1447–1448

    CAS  PubMed  Google Scholar 

  • Brady SF, Wagenaar MM, Singh MP, Janso JE, Clardy J (2000a) The cytosporones, new octaketide antibiotics isolated from an endophytic fungus. Org Lett 2:4043–4046

    CAS  Google Scholar 

  • Brady SF, Singh MP, Janso JE, Clardy J (2000b) Cytoskyrins A and B, new BIA active bisanthraquinones isolated from an endophytic fungus. Org Lett 2:4047–4049

    CAS  Google Scholar 

  • Brahmachari G (2004) Neem – an omnipotent plant: a retrospection. Chembiochem 5:408–421

    CAS  PubMed  Google Scholar 

  • Brown MD (1999) Green tea (Camellia sinensis) extract and its possible role in the prevention of cancer. Altern Med Rev 4:360–370

    CAS  PubMed  Google Scholar 

  • Busam L, Habermehl GG (1982) Accumulation of mycotoxins by Baccharis coridifolia: A reason of livestock poisoning. Naturwissenschaften 69:392–393

    CAS  PubMed  Google Scholar 

  • Camarda L, Merlini L, Nasini G (1976) Metabolites of Cercospora taiwapyrone, an α-pyrone of unusual structure from Cercospora taiwanensis. Phytochemistry 15:537–539

    CAS  Google Scholar 

  • Cassady JM, Chan KK, Floss HG, Leistner E (2004) Recent developments in the maytansinoid antitumor agents. Chem Pharm Bull 52:1–26

    CAS  PubMed  Google Scholar 

  • 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 25:211–244

    CAS  PubMed  Google Scholar 

  • Chapela IH (1989) Fungi in healthy stems and branches of American beech and aspen: a comparative study. New Phytol 113:65–75

    Google Scholar 

  • Chapela IH, Boddy L (1988) Fungal colonization of attached beech branches I. Early stages of development of fungal communities. New Phytol 110:39–45

    Google Scholar 

  • Chapela IH, Petrini O, Hagmann L (1991) Monolignol glucosides as specific recognition messengers in fungal/plant symbiosis. Physiol Mol Plant Pathol 39:289–298

    CAS  Google Scholar 

  • 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 97:157–162

    Google Scholar 

  • Chen LG, Yang LL, Wang CC (2008) Anti-inflammatory activity of mangostins from Garcinia mangostana. Food Chem Toxicol 46:688–693

    CAS  PubMed  Google Scholar 

  • 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 56:982–984

    CAS  PubMed  Google Scholar 

  • 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 69:1351–1353

    CAS  Google Scholar 

  • Clavin M, Lorenzen K, Mayer A, Martino V, Anke T (1999) Biological activities in medicinal species of Eupatorium. Acta Hort 501:277–281

    Google Scholar 

  • 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 14:275–277

    CAS  Google Scholar 

  • 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° 16:131–134

    Google Scholar 

  • 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 79–105

    Google Scholar 

  • Clay K (1988b) Fungal endophytes of grasses: a defensive mutualism between plants and fungi. Ecology 69:10–16

    Google Scholar 

  • Claydon N, Grove JF, Pople M (1985) Elm bark beetle boring and feeding deterrents from Phomopsis oblonga. Phytochemistry 24:937–943

    CAS  Google Scholar 

  • 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 2:24

    CAS  PubMed  Google Scholar 

  • 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 15:3498–3506

    Google Scholar 

  • Dalsgaard PW, Larsen TO, Christophersen C (2005) Bioactive cyclic peptides from the psychrotolerant fungus Penicillium algidum. J Antibiot 58:141–144

    CAS  PubMed  Google Scholar 

  • de Bary A (1879) Die Erscheinungen der Symbiose. Verlag von Karl J. Trübner, Strassbourg

    Google Scholar 

  • Descoins C Jr, Bazzocchi IL, Ravelo AG (2002) New sesquiterpenes from Euonymus europaeus (Celastraceae). Chem Pharm Bull 50:199–202

    CAS  PubMed  Google Scholar 

  • Dikshit A, Naqvi AA, Husain A (1986) Schinus molle, a new source of natural fungitoxicant. Appl Environ Microbiol 51:1085–1088

    CAS  PubMed  Google Scholar 

  • 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 69:302–304

    CAS  PubMed  Google Scholar 

  • Ding G, Liu S, Guo L, Zou Y, Che Y (2008) Antifungal metabolites from the plant endophytic fungus Pestalotiopsis foedan. J Nat Prod 71:615–618

    CAS  PubMed  Google Scholar 

  • 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 342:1343–1349

    CAS  Google Scholar 

  • 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 49–80

    Google Scholar 

  • Dugoua JJ, Mills E, Perri D, Koren G (2006) Safety and efficacy of Ginkgo (Ginkgo biloba) during pregnancy and lactation. Can J Clin Pharmacol 13:277–284

    Google Scholar 

  • 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 48:82–92

    PubMed  Google Scholar 

  • Endo A, Hasumi K (1997) Mevinic acids. In: Anke T (ed) Fungal biotechnology. Chapman & Hall, London, pp 162–172

    Google Scholar 

  • Eyberger AL, Dondapati R, Porter JR (2006) Endophyte fungal isolates from Podophyllum peltatum produce podophyllotoxin. J Nat Prod 69:1121–1124

    CAS  PubMed  Google Scholar 

  • 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 36:125–140

    CAS  PubMed  Google Scholar 

  • 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:547–552

    Google Scholar 

  • Freeman EM (1902) The seed fungus of Lolium temulentum, L., the Darnel. Philos Trans R Soc London Bio1:1–27

    Google Scholar 

  • Freeman S, Rodriguez RJ (1993) Genetic conversion of a fungal plant pathogen to a nonpathogenic, endophytic mutualist. Science 260:75–78

    CAS  PubMed  Google Scholar 

  • 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 56:1427–1437

    CAS  PubMed  Google Scholar 

  • 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 69:571–576

    CAS  PubMed  Google Scholar 

  • 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 7:138–148

    PubMed  Google Scholar 

  • Girault L (1987) Kallawaya. Curanderos itinerantes de los Andes. Unicef/OPS/OMS, La Paz, p. 462

    Google Scholar 

  • 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 23:1371–1375

    Google Scholar 

  • Govindachari TR, Ravindranath KR, Viswanathan N (1974) Mappicine, a minor alkaloid from Mappia foetida Miers. J Chem Soc Perkin Trans I 11:2215–1217

    Google Scholar 

  • Grove JF, Pople M (1979) Metabolic products of Fusarium lavarum Fuckel. The fusarentins and the absolute configuration of moncerin. J. C. S. Perkin 1:2048–2051

    Google Scholar 

  • 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 70:114–117

    CAS  PubMed  Google Scholar 

  • Gunatilaka AAL (2006) Natural products from plant-associated microorganisms: Distribution, structural diversity, bioactivity, and implications of their occurence. J Nat Prod 69:509–526

    CAS  PubMed  Google Scholar 

  • Hamilton-Miller JMT (1995) Antimicrobial properties of tea (Camellia sinensis L.). Antimicrob Agents Chemother 39:2375–2377

    CAS  PubMed  Google Scholar 

  • Hamilton-Miller JMT (2001) Anti-carciogenic properties of tea (Camellia sinensis). J Med Microbiol 50:299–302

    CAS  PubMed  Google Scholar 

  • Hashida C, Tanaka N, Kashiwada Y, Ogawa M, Takaishi Y (2008) Prenylated chloroglucinol derivates from Hypericum perforatum var. angustifolium. Chem Pharm Bull 56:1164–1167

    CAS  PubMed  Google Scholar 

  • Hawksworth DL (2001) The magnitude of fungal diversity: the 1.5 million species estimated revisited. Mycol Res 105:1422–1432

    Google Scholar 

  • 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 71:1697–1702

    CAS  PubMed  Google Scholar 

  • 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 55:881–892

    CAS  PubMed  Google Scholar 

  • Hill NS, Belesky DP, Stringer WC (1991) Competitiveness of tall fescue as influenced by Acremonium coenophialum. Crop Sci 31:185–190

    Google Scholar 

  • 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 6:719–721

    PubMed  Google Scholar 

  • 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 23:1253–1263

    CAS  Google Scholar 

  • Iharlegui L, Hurrel J (1992) Asteraceae de interes ethnobotanico de los departamentos de Santa Victoria e Iruya (Salta, Argentinien). Ecognicion 3:3–18

    Google Scholar 

  • 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 64:1015–1018

    CAS  PubMed  Google Scholar 

  • 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 26:1351–1353

    CAS  PubMed  Google Scholar 

  • 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 52:1145–1147

    CAS  PubMed  Google Scholar 

  • Jennewein S, Croteau R (2001) Taxol: biosynthesis, molecular genetics, and biotechnological applications. Appl Microbiol Biotechnol 57:13–19

    CAS  PubMed  Google Scholar 

  • Jiang Y, Tu PF (2009) Analysis of chemical constituents in Cistanche species. J Chromatogr A 1216:1970–1979

    CAS  PubMed  Google Scholar 

  • 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 1:328–337

    CAS  Google Scholar 

  • 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 80:665–658

    Google Scholar 

  • Kang DG, Yin MH, Oh H, Lee DH, Lee HS (2004) Vasorelaxation by amentoflavone isolated from Selaginella tamariscina. Planta Med 70:718–722

    CAS  PubMed  Google Scholar 

  • 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 16:843–848

    CAS  PubMed  Google Scholar 

  • Kimmons CA, Gwinn KD, Bernard EC (1990) Nematode reproduction on endophyte-infected and endophyte-free tall fescue. Plant Dis 74:757–761

    Google Scholar 

  • 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 19:464–470

    CAS  Google Scholar 

  • 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 7:1123–1129

    Google Scholar 

  • 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 219:619–625

    CAS  PubMed  Google Scholar 

  • Kumar DS, Hyde KD (2004) Biodiversity and tissue-recurrence of endophytic fungi in Tripterygium wilfordii. Fungal Divers 17:69–90

    CAS  Google Scholar 

  • Kusari S, Lamshöft M, Zühlke S, Spiteller M (2008) An endophytic fungus from Hypericum perforatum that produces hypericin. J Nat Prod 71:159–162

    CAS  PubMed  Google Scholar 

  • Lambert JD, Yang CS (2003) Mechanisms of cancer prevenion by tea constituents. J Nutr 133:3262–3267

    Google Scholar 

  • Langford SD, Boor PJ (1996) Oleander toxicity: an examination of human and animal toxic exposures. Toxicology 3:1–13

    Google Scholar 

  • 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 71:664–668

    CAS  PubMed  Google Scholar 

  • 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 21:1515–1519

    Google Scholar 

  • 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 23:1037–1040

    Google Scholar 

  • 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 56:217–221

    CAS  Google Scholar 

  • 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 61:81–85

    CAS  Google Scholar 

  • 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 86:657–660

    CAS  Google Scholar 

  • 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 78:241–247

    CAS  PubMed  Google Scholar 

  • 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 41:1186–1190

    CAS  PubMed  Google Scholar 

  • Luper S (1999) A review of plants used in the treatment of liver disease: part two. Altern Med Rev 4:178–188

    CAS  PubMed  Google Scholar 

  • 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 51:1264–1267

    CAS  PubMed  Google Scholar 

  • 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:319–324

    Google Scholar 

  • 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 8:4067–4070

    CAS  PubMed  Google Scholar 

  • 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 62:11–15

    CAS  PubMed  Google Scholar 

  • Meng LH, Liao ZY, Pommier Y (2003) Non-camptothecin DNA topoisomerase I inhibitors in cancer therapy. Curr Top Med Chem 3:305–320

    CAS  PubMed  Google Scholar 

  • Miller AL (1998a) St. John's wort (Hypericum perforatum): clinical effects on depression and other conditions. Altern Med Rev 3:18–26

    CAS  Google Scholar 

  • Miller AL (1998b) Botanical influences on cardiovascular disease. Altern Med Rev 3:422–431

    CAS  Google Scholar 

  • 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 21:93–98

    Google Scholar 

  • Mitscher LA, Gollapudi RSR, Gerlach DC, Drake SD, Veliz EA, Ward JA (1988) Erycristin, a new antimicrobial petrocarpan from Erythrina crista-galli. Phytochemistry 27:381–385

    CAS  Google Scholar 

  • 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 159:245–249

    PubMed  Google Scholar 

  • Nebenführ A, Ritzenthaler C, Robinson DG (2002) Brefeldin A: deciphering an enigmatic inhibitor of secretion. Plant Physiology 130:1102–1108

    PubMed  Google Scholar 

  • Nishikawa W (1933) A metabolic product of Aspergillus melleus Yukawa. J Agric Chem Soc Japan Chem 9:772

    CAS  Google Scholar 

  • Oberlies NH, Kroll DJ (2004) Camptothecin and taxol: historic achievements in natural product research. J Nat Prod 67:129–135

    CAS  PubMed  Google Scholar 

  • Park SH, Ko SK, Chung SH (2005) Euronymus alatus prevents the hyperglycemia and hyperlipidemia induced by high-fat diet in ICR mice. J Ethnopharmacol 102:326–335

    PubMed  Google Scholar 

  • Parker EJ, Scott DB (2004) Indole-diterpene biosynthesis in ascomycetous fungi. In: An Z (ed) Handbook of industrial mycology. Dekker, New York, pp 405–426

    Google Scholar 

  • Pedraza-Chaverri J, Cárdenas-Rodríguez N, Orozo-Ibarra M, Pérez-Rojas JM (2008) Medicinal properties of mangosteen (Garcinia mangostana). Food Chem Toxicol 46:3227–3239

    CAS  PubMed  Google Scholar 

  • 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 5:21–28

    Google Scholar 

  • 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 87–100

    Google Scholar 

  • Petrini O, Petrini LE, Rodrigues KF (1995) Xylariaceous endophytes: an exercise in biodiversity. Fitopatol Bras 20:531–539

    Google Scholar 

  • 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 1–29

    Google Scholar 

  • Pirozynski KA, Malloch DW (1975) The origin of plants: a matter of mycotrophism. Biosystems 6:153–164

    CAS  PubMed  Google Scholar 

  • Poch GK, Gloer JB, Shearer CA (1992) New bioactive metabolites from a freshwater isolate of the fungus Kirschsteiniothelia sp. J Nat Prod 55:1093–1099

    CAS  PubMed  Google Scholar 

  • Pongcharoen W, Rukachaisirikul V, Phongpaichit S, Sakayaroj J (2007) A new didydrobenzofuran derivative from the endophytic fungus Botryosphaeria mamane PSU-M76. Chem Pharm Bull 55:1404–1405

    CAS  PubMed  Google Scholar 

  • 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 29:140–144

    CAS  PubMed  Google Scholar 

  • 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 61:2122–2124

    CAS  Google Scholar 

  • 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 46:313–319

    CAS  Google Scholar 

  • Puri SC, Verma V, Amna T, Qazi GN, Spiteller M (2005) An endophytic fungus from Nothapodytes foedida that produces camptothecin. J Nat Prod 68:1717–1719

    CAS  PubMed  Google Scholar 

  • 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 122:494–510

    CAS  PubMed  Google Scholar 

  • Quiroga EN, Sampietro AR, Vattuone MA (2001) Screening antifungal activities of selected medicinal plants. J Ethnopharmacol 74:89–96

    CAS  PubMed  Google Scholar 

  • Rasadah MA, Khozirah S, Aznie AA, Nik MM (2004) Anti-inflammatory agents from Sandoricum koetjape Merr. Phytomedicine 11:262–263

    Google Scholar 

  • Raviraja NS (2005) Fungal endophytes in five medicinal plant species from Kudremukh Range, Western Ghats of India. J Basic Microbiol 45:230–235

    CAS  PubMed  Google Scholar 

  • Read JC, Camp BJ (1986) The effect of fungal endophyte Acremonium coenophialum in tall fescue on animal performance, toxicity, and stand maintenance. Agron J 78:848–850

    Google Scholar 

  • 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 154:1973–1979

    CAS  PubMed  Google Scholar 

  • Rizzo I, Varsavky E, Haidukowski M, Frade H (1997) Macrocyclic trichothecenes in Baccharis coridifolia plants and endophytes and Baccharis artemisioides plants. Toxicon 35:753–757

    CAS  PubMed  Google Scholar 

  • Rogers JD (1979) The Xylariaceae: Systematic, biological and evolutionary aspects. Mycologia 71:1–42

    Google Scholar 

  • 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 13:514–521

    Google Scholar 

  • Roth L, Daunderer M, Kormann K (1994) Giftpflanzen Pflanzengifte. Nikol, Hamburg

    Google Scholar 

  • 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 55:1383–1384

    CAS  PubMed  Google Scholar 

  • Saikkonen K, Faeth SH, Helander M, Sullivan TJ (1998) Fungal endophytes: a continuum of interactions with host plants. Annu Rev Ecol Syst 29:319–343

    Google Scholar 

  • 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 427–448

    Google Scholar 

  • Schardl CL, Panaccione DG, Tudzynski P (2006) Ergot alkaloids – biology and molecular biology. Alkaloids 63:47–88

    Google Scholar 

  • 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 21:27–32

    CAS  Google Scholar 

  • Schmeda-Hirschmann G, Hormazabal E, Rodriguez JA, Theoduloz C (2008) Cycloaspeptide A and pseurotin A from the endophytic fungus Penicillium janczewskii. Z Naturforsch 63c:383–388

    Google Scholar 

  • 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 71:1470–1475

    CAS  PubMed  Google Scholar 

  • 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 41:721–734

    CAS  PubMed  Google Scholar 

  • Shiono Y, Muranyama T (2005) New eremophilane-type sequiterpenoids, eremoxylarins A and B from xylariaceous endophytic fugus YUA-026. Z Naturforsch 60b:885–890

    Google Scholar 

  • 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 60:309–316

    CAS  PubMed  Google Scholar 

  • Silberstein SD, McCrory DC (2003) Ergotamine and dihydroergotamine: history, pharmacology, and efficacy. Headache 43:411–166

    Google Scholar 

  • 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 67:1964–1969

    CAS  PubMed  Google Scholar 

  • 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 3–29

    Google Scholar 

  • 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 39:567–576

    CAS  Google Scholar 

  • Stierle A, Strobel G, Stierle D (1993) Taxol and taxane production by Taxomyces andreanae, an endophytic fungus of pazific yew. Science 260:214–216

    CAS  PubMed  Google Scholar 

  • 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 389–420

    Google Scholar 

  • Strobel G (2003) Endophytes as sources of bioactive products. Microbes Infect 5:535–544

    CAS  PubMed  Google Scholar 

  • 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 60:179–183

    CAS  PubMed  Google Scholar 

  • Strobel G, Daisy B, Castillo U, Harper J (2004) Natural products from endophytic microorganisms. J Nat Prod 67:257–268

    CAS  PubMed  Google Scholar 

  • 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 51:857–859

    CAS  PubMed  Google Scholar 

  • 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 33:357–374

    CAS  Google Scholar 

  • 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 90:1811–1817

    CAS  Google Scholar 

  • Tan RX, Zou WX (2001) Endophytes: a rich source of functional metabolites. Nat Prod Rep 18:448–459

    CAS  PubMed  Google Scholar 

  • Tan RX, Zheng WF, Tang HQ (1998) Biologically active substances from the genus Artemisia. Planta Med 64:295–302

    CAS  PubMed  Google Scholar 

  • 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 70:1620–1623

    CAS  PubMed  Google Scholar 

  • 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 21:1535–1540

    Google Scholar 

  • Toursarkissian M (1980) Plantas Medicinales de la Argentina. Hemisferio Sur, Buenos Aires, p. 70

    Google Scholar 

  • Uecker FA (1988) A world list of Phomopsis names with notes on nomenclature, morphology and biology. Cramer, Berlin

    Google Scholar 

  • van Eijik GW, Royemans HJ (1978) Naphthoquinone derivatives from the fungus Hendersonula toruloidea. Experientia 34:1257–1258

    Google Scholar 

  • 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 56:407–412

    CAS  PubMed  Google Scholar 

  • Vogl AE (1898) Mehl und die anderen Mehlprodukte der Cerealien und Leguminosen. Nahrungsm Unters Hyg Warenk 12:25–29

    Google Scholar 

  • 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 64:1006–1009

    Google Scholar 

  • Walker K, Croteau R (2001) Molecules of interest. Taxol biosynthetic genes. Phytochemistry 58:1–7

    CAS  PubMed  Google Scholar 

  • 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 88:3888–3890

    CAS  Google Scholar 

  • 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 44:1317–1322

    CAS  PubMed  Google Scholar 

  • 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 55:404–410

    CAS  PubMed  Google Scholar 

  • 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 93:2325–2327

    CAS  PubMed  Google Scholar 

  • Webber J (1981) A natural biological control of dutch elm disease. Nature 292:449–451

    Google Scholar 

  • Weber D (2006) Biologisch aktive Metabolite endophytischer Pilze argentinischer Medizinalpflanzen und anderer Pilze. Dissertation, University of Kaiserslautern

    Google Scholar 

  • 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 57:559–563

    CAS  PubMed  Google Scholar 

  • 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 60:467–477

    CAS  PubMed  Google Scholar 

  • 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, Wallingford

    Google Scholar 

  • 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 108:662–671

    CAS  PubMed  Google Scholar 

  • Webster J, Weber RWS (2004) Teaching techniques for mycology: 23. Eclosion of Hypoxylon fragiforme ascospores as a prelude to germination. Mycologist 18:170–173

    Google Scholar 

  • Wenke J (1993) Isolierung und Charakterisierung neuer Inhibitoren der Chitinsynthase aus höheren Pilzen. Dissertation, University of Kaiserslautern

    Google Scholar 

  • 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 85:264–270

    Google Scholar 

  • Whalley AJS (1996) The xylariaceous way of life. Mycol Res 100:897–922

    Google Scholar 

  • White JF Jr, Cole GT (1985) Endophyte–host associations in forage grasses. III. In vitro inhibition of fungi by Acremonium coenophialum. Mycologia 77:487–489

    Google Scholar 

  • 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 49–62

    Google Scholar 

  • 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 71:218–222

    CAS  PubMed  Google Scholar 

  • Wilson D (2000) Ecology of woody plant endopyhtes. In: Bacon CW, White JF (eds) Microbial endophytes. Dekker, New York, pp 389–420

    Google Scholar 

  • 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 20:265–272

    Google Scholar 

  • Woerdenbag HJ, Lugt CB, Pras N (1990) Artemisia annua L.: a source of novel antimalarial drugs. Pharm Weekbl Sci 19:169–181

    Google Scholar 

  • 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 71:731–734

    CAS  PubMed  Google Scholar 

  • 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 71:1251–1253

    CAS  PubMed  Google Scholar 

  • Yang SF, Prabhu S, Landau J (2001) Prevention of carcinogenesis by tea phenols. Drug Metab Rev 33:237–253

    CAS  PubMed  Google Scholar 

  • 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 110:483–489

    PubMed  Google Scholar 

  • 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 26:5551–5554

    Google Scholar 

  • 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 63:1529–1530

    CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2009 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Weber, D. (2009). Endophytic Fungi, Occurrence and Metabolites. In: Anke, T., Weber, D. (eds) Physiology and Genetics. The Mycota, vol 15. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-00286-1_8

Download citation

Publish with us

Policies and ethics