Advertisement

Endophytic Fungi as a Source of Novel Metabolites

  • Fernanda O. Chagas
  • Andrés Mauricio Caraballo-Rodriguez
  • Mônica T. PupoEmail author
Chapter
Part of the Fungal Biology book series (FUNGBIO)

Abstract

Microorganisms inhabiting plant tissues without causing any damage to their host plant are referred to as endophytes and can be fungi or bacteria, including actinobacteria. Due to a direct interaction between plant and endophytes, these microorganisms are an interesting source for biologically active natural products. Here, we reviewed the novel compounds isolated from endophytic fungi from 2012 to April 2014, mentioning their biological activities as well as their biological sources. Only secondary metabolites containing any interesting structural novelty or relevant biological activity were highlighted. The novel metabolites were classified into four major groups based on their biosynthetic pathway, such as polyketide and fatty acid, phenylpropanoid, and terpenoid derivatives as well as N-containing compounds. Taking into account that laboratorial conditions may lead to a minimal or absent production of many interesting microbial metabolites produced by the endophytes while interacting in their natural habitat, some approaches have been applied to the endophytes cultures and some examples of new metabolites obtained by using those strategies are also mentioned.

Keywords

Endophytic fungi Natural products Secondary metabolites Biosynthetic pathway Polyketide Fatty acid Phenylpropanoid Terpenoid Nonribosomal peptide Alkaloid 

References

  1. 1.
    Staniek A, Woerdenbag HJ, Kayser O (2008) Endophytes: exploiting biodiversity for the improvement of natural product-based drug discovery. J Plant Interact 3(2):75–93Google Scholar
  2. 2.
    Kusari S, Hertweck C, Spitellert M (2012) Chemical ecology of endophytic fungi: origins of secondary metabolites. Chem Biol 19(7):792–798PubMedGoogle Scholar
  3. 3.
    Aly AH, Debbab A, Kjer J, Proksch P (2010) Fungal endophytes from higher plants: a prolific source of phytochemicals and other bioactive natural products. Fungal Divers 41(1):1–16Google Scholar
  4. 4.
    Ryan RP, Germaine K, Franks A, Ryan DJ, Dowling DN (2008) Bacterial endophytes: recent developments and applications. FEMS Microbiol Lett 278(1):1–9PubMedGoogle Scholar
  5. 5.
    Kogel K-H, Franken P, Hueckelhoven R (2006) Endophyte or parasite—what decides? Curr Opin Plant Biol 9(4):358–363PubMedGoogle Scholar
  6. 6.
    Gutierrez RMP, Gonzalez AMN, Ramirez AM (2012) Compounds derived from endophytes: a review of phytochemistry and pharmacology. Curr Med Chem 19(18):2992–3030PubMedGoogle Scholar
  7. 7.
    Redecker D, Kodner R, Graham LE (2000) Glomalean fungi from the Ordovician. Science 289(5486):1920–1921PubMedGoogle Scholar
  8. 8.
    Schulz B, Boyle C (2005) The endophytic continuum. Mycol Res 109:661–686PubMedGoogle Scholar
  9. 9.
    Rudgers JA, Koslow JM, Clay K (2004) Endophytic fungi alter relationships between diversity and ecosystem properties. Ecol Lett 7(1):42–51Google Scholar
  10. 10.
    Schardl CL, Leuchtmann A, Spiering MJ (2004) Symbioses of grasses with seedborne fungal endophytes. Annu Rev Plant Biol 55:315–340PubMedGoogle Scholar
  11. 11.
    Muller CB, Krauss J (2005) Symbiosis between grasses and asexual fungal endophytes. Curr Opin Plant Biol 8(4):450–456PubMedGoogle Scholar
  12. 12.
    Saikkonen K, Gundel PE, Helander M (2013) Chemical ecology mediated by fungal endophytes in grasses. J Chem Ecol 39(7):962–968PubMedGoogle Scholar
  13. 13.
    Waller F, Achatz B, Baltruschat H, Fodor J, Becker K, Fischer M et al (2005) The endophytic fungus Piriformospora indica reprograms barley to salt-stress tolerance, disease resistance, and higher yield. Proc Natl Acad Sci U S A 102(38):13386–13391PubMedCentralPubMedGoogle Scholar
  14. 14.
    Zhang HW, Song YC, Tan RX (2006) Biology and chemistry of endophytes. Nat Prod Rep 23(5):753–771PubMedGoogle Scholar
  15. 15.
    Gunatilaka AAL (2006) Natural products from plant-associated microorganisms: distribution, structural diversity, bioactivity, and implications of their occurrence. J Nat Prod 69(3):509–526PubMedCentralPubMedGoogle Scholar
  16. 16.
    Rodriguez R, Redman R (2008) More than 400 million years of evolution and some plants still can’t make it on their own: plant stress tolerance via fungal symbiosis. J Exp Bot 59(5):1109–1114PubMedGoogle Scholar
  17. 17.
    Bae H, Sicher RC, Kim MS, Kim S-H, Strem MD, Melnick RL et al (2009) The beneficial endophyte Trichoderma hamatum isolate dis 219b promotes growth and delays the onset of the drought response in Theobroma cacao. J Exp Bot 60(11):3279–3295PubMedCentralPubMedGoogle Scholar
  18. 18.
    Sabzalian MR, Mirlohi A (2010) Neotyphodium endophytes trigger salt resistance in tall and meadow fescues. J Plant Nutr Soil Sci 173(6):952–957Google Scholar
  19. 19.
    Weyens N, van der Lelie D, Taghavi S, Vangronsveld J (2009) Phytoremediation: plant-endophyte partnerships take the challenge phytoremediation: plant-endophyte partnerships take the challenge. Curr Opin Biotechnol 20(2):248–254PubMedGoogle Scholar
  20. 20.
    Hartley SE, Gange AC (2009) Impacts of plant symbiotic fungi on insect herbivores: mutualism in a multitrophic context. Annu Rev Entomol 54:323–342PubMedGoogle Scholar
  21. 21.
    Rocha ACS, Garcia D, Uetanabaro APT, Carneiro RTO, Araujo IS, Mattos CRR et al (2011) Foliar endophytic fungi from Hevea brasiliensis and their antagonism on Microcyclus ulei. Fungal Divers 47(1):75–84Google Scholar
  22. 22.
    Aly AH, Debbab A, Proksch P (2011) Fungal endophytes: unique plant inhabitants with great promises. Appl Microbiol Biotechnol 90(6):1829–1845PubMedGoogle Scholar
  23. 23.
    Alvin A, Miller KI, Neilan BA (2014) Exploring the potential of endophytes from medicinal plants as sources of antimycobacterial compounds. Microbiol Res 169(7–8):483–495PubMedGoogle Scholar
  24. 24.
    Stierle A, Strobel G, Stierle D. (1993) Taxol and taxane production by taxomyces-andreanae, an endophytic fungus of Pacific yew. Science 260(5105):214–216.PubMedGoogle Scholar
  25. 25.
    Puri SC, Verma V, Amna T, Qazi GN, Spiteller M (2005) An endophytic fungus from Nothapodytes foetida that produces camptothecin. J Nat Prod 68(12):1717–1719PubMedGoogle Scholar
  26. 26.
    Kusari S, Zuehlke S, Spiteller M (2009) An endophytic fungus from Camptotheca acuminata that produces camptothecin and analogues. J Nat Prod 72(1):2–7PubMedGoogle Scholar
  27. 27.
    Kusari S, Zuehlke S, Spiteller M (2011) Effect of artificial reconstitution of the interaction between the plant Camptotheca acuminata and the fungal endophyte Fusarium solani on camptothecin biosynthesis. J Nat Prod 74(4):764–775PubMedGoogle Scholar
  28. 28.
    Shweta S, Zuehlke S, Ramesha BT, Priti V, Kumar PM, Ravikanth G et al (2010) Endophytic fungal strains of Fusarium solani, from Apodytes dimidiata E.. Mey. ex Arn (Icacinaceae) produce camptothecin, 10-hydroxycamptothecin and 9-methoxycamptothecin. Phytochemistry 71(1):117–122PubMedGoogle Scholar
  29. 29.
    Puri SC, Nazir A, Chawla R, Arora R, Riyaz-ul-Hasan S, Amna T et al (2006) The endophytic fungus Trametes hirsuta as a novel alternative source of podophyllotoxin and related aryl tetralin lignans. J Biotechnol 122(4):494–510PubMedGoogle Scholar
  30. 30.
    Eyberger AL, Dondapati R, Porter JR (2006) Endophyte fungal isolates from Podophyllum peltatum produce podophyllotoxin. J Nat Prod 69(8):1121–1124PubMedGoogle Scholar
  31. 31.
    Kusari S, Lamshoeft M, Spiteller M (2009) Aspergillus fumigatus Fresenius, an endophytic fungus from Juniperus communis L. Horstmann as a novel source of the anticancer pro-drug deoxypodophyllotoxin. J Appl Microbiol 107(3):1019–1030PubMedGoogle Scholar
  32. 32.
    Kusari S, Lamshoeft M, Zuehlke S, Spiteller M (2008) An endophytic fungus from hypericum perforatum that produces hypericin. J Nat Prod 71(2):159–162PubMedGoogle Scholar
  33. 33.
    Kusari S, Zuehlke S, Kosuth J, Cellarova E, Spiteller M (2009) Light-independent metabolomics of endophytic Thielavia subthermophila provides insight into microbial hypericin biosynthesis. J Nat Prod 72(10):1825–1835PubMedGoogle Scholar
  34. 34.
    Kusari S, Verma VC, Lamshoeft M, Spiteller M (2012) An endophytic fungus from Azadirachta indica A. Juss. That produces azadirachtin. World J Microbiol Biotechnol 28(3):1287–1294PubMedGoogle Scholar
  35. 35.
    Kusari S, Spiteller M (2011) Are we ready for industrial production of bioactive plant secondary metabolites utilizing endophytes? Nat Prod Rep 28(7):1203–1207PubMedGoogle Scholar
  36. 36.
    Heinig U, Scholz S, Jennewein S (2013) Getting to the bottom of taxol biosynthesis by fungi. Fungal Divers 60(1):161–170Google Scholar
  37. 37.
    Boemke C, Tudzynski B (2009) Diversity, regulation, and evolution of the gibberellin biosynthetic pathway in fungi compared to plants and bacteria. Phytochemistry. 70(15–16):1876–1893Google Scholar
  38. 38.
    Xiong Z-Q, Yang Y-Y, Zhao N, Wang Y (2013) Diversity of endophytic fungi and screening of fungal paclitaxel producer from Anglojap yew, Taxus x media. BMC Microbiol 13:71PubMedCentralPubMedGoogle Scholar
  39. 39.
    Yang Y, Zhao H, Barrero RA, Zhang B, Sun G, Wilson IW et al (2014) Genome sequencing and analysis of the paclitaxel-producing endophytic fungus Penicillium aurantiogriseum NRRL 62431. BMC Genomics 15:69PubMedCentralPubMedGoogle Scholar
  40. 40.
    Valachova M, Muckova M, Sturdikova M (2007) Metabolites of endophytic microorganisms as bioactive compounds. Chem Listy 101(6):486–494Google Scholar
  41. 41.
    Kharwar RN, Mishra A, Gond SK, Stierle A, Stierle D (2011) Anticancer compounds derived from fungal endophytes: their importance and future challenges. Nat Prod Rep 28(7):1208–1228PubMedGoogle Scholar
  42. 42.
    Debbab A, Aly AH, Proksch P (2012) Endophytes and associated marine derived fungi-ecological and chemical perspectives. Fungal Divers 57(1):45–83Google Scholar
  43. 43.
    Kusari S, Pandey SP, Spiteller M (2013) Untapped mutualistic paradigms linking host plant and endophytic fungal production of similar bioactive secondary metabolites. Phytochemistry 91:81–87PubMedGoogle Scholar
  44. 44.
    de Souza JJ, Vieira IJC, Rodrigues E, Braz R (2011) Terpenoids from endophytic fungi. Molecules 16(12):10604–10618 (Review)PubMedGoogle Scholar
  45. 45.
    Debbab A, Aly AH, Proksch P (2011) Bioactive secondary metabolites from endophytes and associated marine derived fungi. Fungal Divers 49(1):1–12 (Review)Google Scholar
  46. 46.
    Debbab A, Aly AH, Proksch P (2013) Mangrove derived fungal endophytes—a chemical and biological perception. Fungal Divers 61(1):1–27Google Scholar
  47. 47.
    Radic N, Strukelj B (2012) Endophytic fungi-the treasure chest of antibacterial substances. Phytomedicine 19(14):1270–1284PubMedGoogle Scholar
  48. 48.
    Wang LW, Zhang YL, Lin FC, Hu YZ, Zhang CL (2011) Natural products with antitumor activity from endophytic fungi. Mini Rev Med Chem 11(12):1056–1074PubMedGoogle Scholar
  49. 49.
    Kaul S, Gupta S, Ahmed M, Dhar MK (2012) Endophytic fungi from medicinal plants: a treasure hunt for bioactive metabolites. Phytochem Rev 11(4):487–505 (Article)Google Scholar
  50. 50.
    Kumar S, Kaushik N (2012) Metabolites of endophytic fungi as novel source of biofungicide: a review. Phytochem Rev 11(4):507–522 (Article)Google Scholar
  51. 51.
    Ebrahim W, Aly AH, Wray V, Proksch P, Debbab A (2013) Unusual octalactones from Corynespora cassiicola, an endophyte of Laguncularia racemosa. Tetrahedron Lett 54(48):6611–6614 (Article)Google Scholar
  52. 52.
    Sommart U, Rukachaisirikul V, Tadpetch K, Sukpondma Y, Phongpaichit S, Hutadilok-Towatana N et al (2012) Modiolin and phthalide derivatives from the endophytic fungus Microsphaeropsis arundinis psu-g18. Tetrahedron 68(48):10005–10010 (Article)Google Scholar
  53. 53.
    El Amrani M, Lai DW, Debbab A, Aly AH, Siems K, Seidel C et al (2014) Protein kinase and hdac inhibitors from the endophytic fungus Epicoccum nigrum. J Nat Prod 77(1):49–56 (Article)PubMedGoogle Scholar
  54. 54.
    Talontsi FM, Douanla-Meli C, Laatsch H (2013) Depsidones from an endophytic fungus Chaetomium sp. associated with Zanthoxylum leprieurii. Zeitschrift Fur Naturforschung (Section B–A Journal of Chemical Sciences) 68(11):1259–1264 (Article)Google Scholar
  55. 55.
    Okoye FBC, Lu S, Nworu CS, Esimone CO, Proksch P, Chadli A et al (2013) Depsidone and diaryl ether derivatives from the fungus Corynespora cassiicola, an endophyte of Gongronema latifolium. Tetrahedron Lett 54(32):4210–4214 (Article)Google Scholar
  56. 56.
    Talontsi FM, Islam MT, Facey P, Douanla-Meli C, von Tiedemann A, Laatsch H (2012) Depsidones and other constituents from Phomopsis sp. caft69 and its host plant Endodesmia calophylloides with potent inhibitory effect on motility of zoospores of grapevine pathogen Plasmopara viticola. Phytochem Lett 5(3):657–664 (Article)Google Scholar
  57. 57.
    Yang SX, Wang HP, Gao JM, Zhang Q, Laatsch H, Kuang Y (2012) Fusaroside, a unique glycolipid from Fusarium sp., an endophytic fungus isolated from melia azedarach. Org Biomol Chem 10(4):819–824 (Article)PubMedGoogle Scholar
  58. 58.
    Ola ARB, Debbab A, Kurtán T, Brötz-Oesterhelt H, Aly AH, Proksch P (2014) Dihydroanthracenone metabolites from the endophytic fungus Diaporthe melonis isolated from Annona squamosa. Tetrahedron Lett 55:3133–3136Google Scholar
  59. 59.
    Klaiklay S, Rukachaisirikul V, Tadpetch K, Sukpondma Y, Phongpaichit S, Buatong J et al (2012) Chlorinated chromone and diphenyl ether derivatives from the mangrove-derived fungus Pestalotiopsis sp. psu-ma69. Tetrahedron 68(10):2299–2305 (Article)Google Scholar
  60. 60.
    Cheng MJ, Wu MD, Yuan GF, Chen YL, Su YS, Hsieh MT et al (2012) Secondary metabolites and cytotoxic activities from the endophytic fungus Annulohypoxylon squamulosum. Phytochem Lett 5(1):219–223 (Article)Google Scholar
  61. 61.
    Macias-Rubalcava ML, Sobrino M, Melendez-Gonzalez C, Hernandez-Ortega S (2014) Naphthoquinone spiroketals and organic extracts from the endophytic fungus Edenia gomezpompae as potential herbicides. J Agri Food Chem 62(16):3553–3562 (Article)Google Scholar
  62. 62.
    Shang Z, Li XM, Li CS, Wang BG (2012) Diverse secondary metabolites produced by marine-derived fungus Nigrospora sp. ma75 on various culture media. Chem Biodivers 9(7):1338–1348 (Article)PubMedGoogle Scholar
  63. 63.
    Araujo FDD, Favaro LCD, Araujo WL, de Oliveira FL, Aparicio R, Marsaioli AJ (2012) Epicolactone—natural product isolated from the sugarcane endophytic fungus Epicoccum nigrum. Eur J Org Chem 2012(27):5225–5230 (Article)Google Scholar
  64. 64.
    Talontsi FM, Dittrich B, Schuffler A, Sun H, Laatsch H (2013) Epicoccolides: antimicrobial and antifungal polyketides from an endophytic fungus Epicoccum sp. associated with Theobroma cacao. Eur J Org Chem 2013(15):3174–3180 (Article)Google Scholar
  65. 65.
    Cheng MJ, Wu MD, Yanai H, Su YS, Chen IS, Yuan GF et al (2012) Secondary metabolites from the endophytic fungus Biscogniauxia formosana and their antimycobacterial activity. Phytochem Lett 5(3):467–472 (Article)Google Scholar
  66. 66.
    Liu L, Li Y, Li L, Cao Y, Guo LD, Liu G et al (2013) Spiroketals of pestalotiopsis fici provide evidence for a biosynthetic hypothesis involving diversified diels-alder reaction cascades. J Org Chem 78(7):2992–3000 (Article)PubMedGoogle Scholar
  67. 67.
    Senadeera SPD, Wiyakrutta S, Mahidol C, Ruchirawat S, Kittakoop P (2012) A novel tricyclic polyketide and its biosynthetic precursor azaphilone derivatives from the endophytic fungus Dothideomycete sp. Org Biomol Chem 10(35):7220–7226 (Article)PubMedGoogle Scholar
  68. 68.
    Ying Y-M, Zheng Z-Z, Zhang L-W, Shan W-G, Wang J-W, Zhan Z-J (2014) Rare c-25 steroids produced by Penicillium chrysogenum p1x, a fungal endophyte of Huperzia serrata. Helvetica Chimica Acta 97(1):95–101Google Scholar
  69. 69.
    Zang LY, Wei W, Guo Y, Wang T, Jiao RH, Ng SW et al (2012) Sesquiterpenoids from the mangrove-derived endophytic fungus Diaporthe sp. J Nat Prod 75(10):1744–1749 (Article)Google Scholar
  70. 70.
    Kawahara T, Itoh M, Izumikawa M, Sakata N, Tsuchida T, Shin-ya K (2013) Three eremophilane derivatives, MBJ-0011, MBJ-0012 and MBJ-0013, from an endophytic fungus Apiognomonia sp. f24023. J Antibiot 66(5):299–302 (Article)PubMedGoogle Scholar
  71. 71.
    Hemberger Y, Xu J, Wray V, Proksch P, Wu J, Bringmann G (2013) Pestalotiopens A and B: stereochemically challenging flexible sesquiterpene-cyclopaldic acid hybrids from Pestalotiopsis sp. Chemistry 19(46):15556–15564 (Article)PubMedGoogle Scholar
  72. 72.
    Huang X, Huang H, Li H, Sun X, Huang H, Lu Y et al (2013) Asperterpenoid A, a new sesterterpenoid as an inhibitor of Mycobacterium tuberculosis protein tyrosine phosphatase B from the culture of Aspergillus sp 16–5c. Org Lett 15(4):721–723PubMedGoogle Scholar
  73. 73.
    Liang H (2008) Sordarin, an antifungal agent with a unique mode of action. Beilstein J Org Chem 4:31PubMedCentralPubMedGoogle Scholar
  74. 74.
    Rukachaisirikul V, Buadam S, Phongpaichit S, Sakayaroj J (2013) Amide, cyclohexenone, and cyclohexenone-sordaricin derivatives from the endophytic fungus Xylaria plebeja PSU-G30. Tetrahedron 69(50):10711–10717 (Article)Google Scholar
  75. 75.
    Xu Y-m, Espinosa-Artiles P, Liu MX, Arnold AE, Gunatilaka AAL (2013) Secoemestrin D, a cytotoxic epitetrathiodioxopiperizine, and emericellenes A–E, five sesterterpenoids from Emericella sp AST0036, a fungal endophyte of Astragalus lentiginosus. J Nat Prod 76(12):2330–2336Google Scholar
  76. 76.
    Haroon MH, Premaratne SR, Choudhry MI, Dharmaratne HRW (2013) A new-glucuronidase inhibiting butyrolactone from the marine endophytic fungus Aspergillus terreus. Nat Prod Res 27(12):1060–1066 (Article)PubMedGoogle Scholar
  77. 77.
    Ebrahim W, Kjer J, El Amrani M, Wray V, Lin W, Ebel R et al (2012) Pullularins E and F, two new peptides from the endophytic fungus Bionectria ochroleuca isolated from the mangrove plant Sonneratia caseolaris. Mar Drugs 10(5):1081–1091PubMedCentralPubMedGoogle Scholar
  78. 78.
    Liu Y-X, Ma S-G, Wang X-J, Zhao N, Qu J, Yu S-S et al (2012) Diketopiperazine alkaloids produced by the endophytic fungus Aspergillus fumigatus from the stem of Erythrophloeum fordii Oliv. Helvetica Chimica Acta 95(8):1401–1408Google Scholar
  79. 79.
    Devi P, Rodrigues C, Naik CG, DʼSouza L (2012) Isolation and characterization of antibacterial compound from a mangrove-endophytic fungus, Penicillium chrysogenum MTCC 5108. Indian J Microbiol 52(4):617–623PubMedCentralPubMedGoogle Scholar
  80. 80.
    Kong F, Wang Y, Liu P, Dong T, Zhu W (2014) Thiodiketopiperazines from the marine-derived fungus Phoma sp OUCMDZ-1847. J Nat Prod 77(1):132–137PubMedGoogle Scholar
  81. 81.
    Gardiner DM, Waring P, Howlett BJ (2005) The epipolythiodioxopiperazine (ETP) class of fungal toxins: distribution, mode of action, functions and biosynthesis. Microbiology-Sgm 151:1021–1032Google Scholar
  82. 82.
    Putri SP, Kinoshita H, Ihara F, Igarashi Y, Nihira T (2009) Farinomalein, a maleimide-bearing compound from the entomopathogenic fungus Paecilomyces farinosus. J Nat Prod 72(8):1544–1546PubMedGoogle Scholar
  83. 83.
    Xu J, Kjer J, Sendker J, Wray V, Guan H, Edrada R et al (2009) Cytosporones, coumarins, and an alkaloid from the endophytic fungus Pestalotiopsis sp. isolated from the chinese mangrove plant Rhizophora mucronata. Bioorg Med Chem 17(20):7362–7367PubMedGoogle Scholar
  84. 84.
    El Amrani M, Debbab A, Aly AH, Wray V, Dobretsov S, Mueller WEG et al (2012) Farinomalein derivatives from an unidentified endophytic fungus isolated from the mangrove plant Avicennia marina. Tetrahedron Lett 53(49):6721–6724Google Scholar
  85. 85.
    Zhang Y, Wang T, Pei YH, Hua HM, Feng BM (2002) Aspergillin PZ, a novel isoindole-alkaloid from Aspergillus awamori. J Antibiot 55(8):693–695PubMedGoogle Scholar
  86. 86.
    Chen L, Liu Y-T, Song B, Zhang H-W, Ding G, Liu X-Z et al (2014) Stereochemical determination of new cytochalasans from the plant endophytic fungus Trichoderma gamsii. Fitoterapia 96:115–122PubMedGoogle Scholar
  87. 87.
    Xue M, Zhang Q, Gao JM, Li H, Tian JM, Pescitelli G (2012) Chaetoglobosin V–B from endophytic Chaetomium globosum: absolute configuration of chaetoglobosins. Chirality 24(8):668–674 (Article)PubMedGoogle Scholar
  88. 88.
    An CY, Li XM, Li CS, Wang MH, Xu GM, Wang BG (2013) Aniquinazolines A–D, four new quinazolinone alkaloids from marine-derived endophytic fungus Aspergillus nidulans. Mar Drugs 11(7):2682–2694 (Article)PubMedCentralPubMedGoogle Scholar
  89. 89.
    Saleem M, Tousif MI, Riaz N, Ahmed I, Schulz B, Ashraf M et al (2013) Cryptosporioptide: a bioactive polyketide produced by an endophytic fungus Cryptosporiopsis sp. Phytochemistry 93:199–202PubMedGoogle Scholar
  90. 90.
    Ortega HE, Graupner PR, Asai Y, TenDyke K, Qiu D, Shen YY et al (2013) Mycoleptodiscins A and B, cytotoxic alkaloids from the endophytic fungus Mycoleptodiscus sp. F0194. J Nat Prod 76(4):741–744PubMedGoogle Scholar
  91. 91.
    El-Neketi M, Ebrahim W, Lin W, Gedara S, Badria F, Saad H-EA et al (2013) Alkaloids and polyketides from Penicillium citrinum, an endophyte isolated from the moroccan plant Ceratonia siliqua. J Nat Prod 76(6):1099–1104PubMedGoogle Scholar
  92. 92.
    Siriwach R, Kinoshita H, Kitani S, Igarashi Y, Pansuksan K, Panbangred W et al (2014) Bipolamides A and B, triene amides isolated from the endophytic fungus Bipolaris sp. MU34. J Antibiot 67(2):167–170PubMedGoogle Scholar
  93. 93.
    Ebrahim W, Aly AH, Wray V, Mandi A, Teiten M-H, Gaascht F et al (2013) Embellicines A and B: absolute configuration and NF-kappa B transcriptional inhibitory activity. J Med Chem 56(7):2991–2999PubMedGoogle Scholar
  94. 94.
    Bode HB, Bethe B, Hofs R, Zeeck A (2002) Big effects from small changes: possible ways to explore natureʼs chemical diversity. Chembiochem 3(7):619–627PubMedGoogle Scholar
  95. 95.
    Cichewicz RH (2010) Epigenome manipulation as a pathway to new natural product scaffolds and their congeners. Nat Prod Rep 27(1):11–22PubMedCentralPubMedGoogle Scholar
  96. 96.
    Pettit RK (2011) Small-molecule elicitation of microbial secondary metabolites. Microb Biotechnol 4(4):471–478PubMedCentralPubMedGoogle Scholar
  97. 97.
    Marmann A, Aly AH, Lin W, Wang B, Proksch P (2014) Co-cultivation-a powerful emerging tool for enhancing the chemical diversity of microorganisms. Mar Drugs 12(2):1043–1065PubMedCentralPubMedGoogle Scholar
  98. 98.
    Bertrand S, Bohni N, Schnee S, Schumpp O, Gindro K, Wolfender J-L (2014) Metabolite induction viamicroorganism co-culture: a potential way to enhance chemical diversity for drug discovery. Biotechnol Adv 32(6):1180–1204 (Epub)PubMedGoogle Scholar
  99. 99.
    Zhang Q, Wang S-Q, Tang H-Y, Li X-J, Zhang L, Xiao J et al (2013) Potential allelopathic indole diketopiperazines produced by the plant endophytic Aspergillus fumigatus using the one strain-many compounds method. J Agri Food Chem 61(47):11447–11452Google Scholar
  100. 100.
    Sun J, Awakawa T, Noguchi H, Abe I (2012) Induced production of mycotoxins in an endophytic fungus from the medicinal plant Datura stramonium l. Bioorg Med Chem Lett 22(20):6397–6400PubMedGoogle Scholar
  101. 101.
    Ul-Hassan SR, Strobel GA, Booth E, Knighton B, Floerchinger C, Sears J (2012) Modulation of volatile organic compound formation in the Mycodiesel-producing endophyte hypoxylon sp. CI-4. Microbiology-Sgm 158:465–473Google Scholar
  102. 102.
    Chagas FO, Dias LG, Pupo MT (2013) A mixed culture of endophytic fungi increases production of antifungal polyketides. J Chem Ecol 39(10):1335–1342PubMedGoogle Scholar
  103. 103.
    Zhu F, Lin Y (2006) Marinamide, a novel alkaloid and its methyl ester produced by the application of mixed fermentation technique to two mangrove endophytic fungi from the South China Sea. Chin Sci Bull 51(12):1426–1430Google Scholar
  104. 104.
    Wang J-p, Lin W, Wray V, Lai D, Proksch P (2013) Induced production of depsipeptides by co-culturing Fusarium tricinctum and Fusarium begoniae. Tetrahedron Lett 54(20):2492–2496Google Scholar
  105. 105.
    Wu B, Wu X, Sun M, Li M (2013) Two novel tyrosinase inhibitory sesquiterpenes induced by CUCL2 from a marine-derived fungus Pestalotiopsis sp. Z233. Mar Drugs 11(8):2713–2721PubMedCentralPubMedGoogle Scholar
  106. 106.
    Chen H, Awakawa T, Sun J, Wakimoto T, Abe I (2013) Epigenetic modifier induced biosynthesis of novel fusaric acid derivatives in endophytic fungi from Datura stramonium l. Nat Prod Bioprospecting 3(1):20–23Google Scholar
  107. 107.
    Asai T, Otsuki S, Sakurai H, Yamashita K, Ozeki T, Oshima Y (2013) Benzophenones from an endophytic fungus, Graphiopsis chlorocephala, from Paeonia lactiflora cultivated in the presence of an NAD(+)-dependent hdac inhibitor. Org Lett 15(8):2058–2061 (Article)PubMedGoogle Scholar
  108. 108.
    Zhu F, Chen G, Wu J, Pan J (2013) Structure revision and cytotoxic activity of marinamide and its methyl ester, novel alkaloids produced by co-cultures of two marine-derived mangrove endophytic fungi. Nat Prod Res 27(21):1960–1964PubMedGoogle Scholar
  109. 109.
    Cao SG, Cryan L, Habeshian KA, Murillo C, Tamayo-Castillo G, Rogers MS et al (2012) Phenolic compounds as antiangiogenic cmg2 inhibitors from Costa rican endophytic fungi. Bioorg Med Chem Lett 22(18):5885–5888 (Article)PubMedCentralPubMedGoogle Scholar
  110. 110.
    Ding G, Qi YX, Liu SC, Guo LD, Chen XL (2012) Photipyrones a and b, new pyrone derivatives from the plant endophytic fungus Pestalotiopsis photiniae. J Antibiot 65(5):271–273 (Article)PubMedGoogle Scholar
  111. 111.
    Hussain H, Krohn K, Ahmed I, Draeger S, Schulz B, Pietro S et al (2012) Phomopsinones a–d: four new pyrenocines from endophytic fungus Phomopsis sp. Eur J Org Chem 2012(9):1783–1789 (Article)Google Scholar
  112. 112.
    Hussain H, Ahmed I, Schulz B, Draeger S, Krohn K (2012) Pyrenocines j–m: four new pyrenocines from the endophytic fungus, Phomopsis sp. Fitoterapia 83(3):523–526 (Article)PubMedGoogle Scholar
  113. 113.
    Hussain H, Krohn K, Schulz B, Draeger S, Nazir M, Saleem M (2012) Two new antimicrobial metabolites from the endophytic fungus, Seimatosporium sp. Nat Prod Commun 7(3):293–294 (Article)PubMedGoogle Scholar
  114. 114.
    Luo DQ, Zhang L, Shi BZ, Song XM (2012) Two new oxysporone derivatives from the fermentation broth of the endophytic plant fungus Pestalotiopsis karstenii isolated from stems of Camellia sasanqua. Molecules 17(7):8554–8560 (Article)Google Scholar
  115. 115.
    Siriwach R, Kinoshita H, Kitani S, Igarashi Y, Pansuksan K, Panbangred W et al (2012) Mycoleptione, a new chromone derivative isolated from the endophytic fungus Mycoleptodiscus sp. mu41. J Antibiot 65(12):627–629 (Article)PubMedGoogle Scholar
  116. 116.
    Tarman K, Palm GJ, Porzel A, Merzweiler K, Arnold N, Wessjohann LA et al (2012) Helicascolide c, a new lactone from an indonesian marine algicolous strain of Daldinia eschscholzii (xylariaceae, ascomycota). Phytochem Lett 5(1):83–86 (Article)Google Scholar
  117. 117.
    Peng W, You F, Li XL, Jia M, Zheng CJ, Han T et al (2013) A new diphenyl ether from the endophytic fungus Verticillium sp. isolated from Rehmannia glutinosa. Chin J Nat Med 11(6):673–675 (Article)PubMedGoogle Scholar
  118. 118.
    Ronsberg D, Debbab A, Mandi A, Wray V, Dai HF, Kurtan T et al (2013) Secondary metabolites from the endophytic fungus pestalotiopsis virgatula isolated from the mangrove plant Sonneratia caseolaris. Tetrahedron Lett 54(25):3256–3259 (Article)Google Scholar
  119. 119.
    Akay S, Ekiz G, Kocabas F, Hames-Kocabas EE, Korkmaz KS, Bedir E (2014) A new 5,6-dihydro-2-pyrone derivative from Phomopsis amygdali, an endophytic fungus isolated from hazelnut (Corylus avellana). Phytochem Lett 7:93–96 (Article)Google Scholar
  120. 120.
    Fang ZF, Yu SS, Zhou WQ, Chen XG, Ma SG, Li Y et al (2012) A new isocoumarin from metabolites of the endophytic fungus Alternaria tenuissima (nees & t. Nees: Fr.) wiltshire. Chin Chem Lett 23(3):317–320 (Article)Google Scholar
  121. 121.
    Li SD, Wei MY, Chen GY, Lin YC (2012) Two new dihydroisocoumarins from the endophytic fungus Aspergillus sp. collected from the South China Sea. Chem Nat Compd 48(3):371–373 (Article)Google Scholar
  122. 122.
    Metwaly AM, Kadry HA, El-Hela AA, Mohammad AEI, Ma GY, Cutler SJ et al (2014) Nigrosphaerin A a new isochromene derivative from the endophytic fungus Nigrospora sphaerica. Phytochem Lett 7:1–5 (Article)Google Scholar
  123. 123.
    Ola ARB, Thomy D, Lai D, Broetz-Oesterhelt H, Prolcsch P (2013) Inducing secondary metabolite production by the endophytic fungus Fusarium tricinctum through coculture with Bacillus subtilis. J Nat Prod 76(11):2094–2099PubMedGoogle Scholar
  124. 124.
    Kumar M, Qadri M, Sharma PR, Kumar A, Andotra SS, Kaur T et al (2013) Tubulin inhibitors from an endophytic fungus isolated from Cedrus deodara. J Nat Prod 6(2):194–199 (Article)Google Scholar
  125. 125.
    Liu SC, Guo LD, Che YS, Liu L (2013) Pestaloficiols q–s from the plant endophytic fungus Pestalotiopsis fici. Fitoterapia 85:114–118 (Article)PubMedGoogle Scholar
  126. 126.
    Jiao Y, Zhang X, Wang L, Li G, Zhou JC, Lou HX (2013) Metabolites from Penicillium sp., an endophytic fungus from the liverwort Riccardia multifida (l.) s. Gray. Phytochem Lett 6(1):14–17 (Article)Google Scholar
  127. 127.
    Jin P, Zuo W, Guo Z, Mei W, Dai H (2013) Metabolites from the endophytic fungus Penicillium sp. Fj-1 of Ceriops tagal. Acta Pharmaceutica Sinica 48(11):1688–1691PubMedGoogle Scholar
  128. 128.
    Rukachaisirikul V, Buadam S, Sukpondma Y, Phongpaichit S, Sakayaroj J, Hutadilok-Towatana N (2013) Indanone and mellein derivatives from the garcinia-derived fungus Xylaria sp. psu-g12. Phytochem Lett 6(1):135–138 (Article)Google Scholar
  129. 129.
    Rukachaisirikul V, Rodglin A, Sukpondma Y, Phongpaichit S, Buatong J, Sakayaroj J (2012) Phthalide and isocoumarin derivatives produced by an Acremonium sp. isolated from a mangrove Rhizophora apiculata. J Nat Prod 75(5):853–858 (Article)PubMedGoogle Scholar
  130. 130.
    Ebrahim W, Aly AH, Mandi A, Wray V, Essassi E, Ouchbani T et al (2013) O-heterocyclic embeurekols from Embellisia eureka, an endophyte of Cladanthus arabicus. Chirality 25(4):250–256 (Article)PubMedGoogle Scholar
  131. 131.
    Song YX, Wang J, Li SW, Cheng B, Li L, Chen B et al (2012) Metabolites of the mangrove fungus Xylaria sp. bl321 from the South China Sea. Planta Medica 78(2):172–176 (Article)PubMedGoogle Scholar
  132. 132.
    Yang JX, Huang RM, Qiu SX, She ZG, Lin YC (2013) A new isobenzofuranone from the mangrove endophytic fungus Penicillium sp. (zh58). Nat Prod Res 27(20):1902–1905 (Article)PubMedGoogle Scholar
  133. 133.
    Xue H, Lu CH, Liang LY, Shen YM (2012) Secondary metabolites of Aspergillus sp. cm9a, an endophytic fungus of Cephalotaxus mannii. Rec Nat Prod 6(1):28–34 (Article)Google Scholar
  134. 134.
    Yan HJ, Li XM, Li CS, Wang BG (2012) Alkaloid and anthraquinone derivatives produced by the marine-derived endophytic fungus Eurotium rubrum. Helv Chim Acta 95(1):163–168 (Article)Google Scholar
  135. 135.
    Ebrahim W, Aly AH, Mandi A, Totzke F, Kubbutat MHG, Wray V et al (2012) Decalactone derivatives from Corynespora cassiicola, an endophytic fungus of the mangrove plant Laguncularia racemosa. Eur J Org Chem 2012(18):3476–3484 (Article)Google Scholar
  136. 136.
    Okoye FBC, Nworu CS, Akah PA, Esimone CO, Debbab A, Proksch P (2013) Inhibition of inflammatory mediators and reactive oxygen and nitrogen species by some depsidones and diaryl ether derivatives isolated from Corynespora cassiicola, an endophytic fungus of Gongronema latifolium leaves. Immunopharmacol Immunotoxicol 35(6):662–668 (Article)PubMedGoogle Scholar
  137. 137.
    Sun HF, Li XM, Meng LH, Cui CM, Gao SS, Li CS et al (2013) Two new secoanthraquinone derivatives from the marine-derived endophytic fungus Aspergillus wentii en-48. Helv Chim Acta 96(3):458–462 (Article)Google Scholar
  138. 138.
    Li X, Li XM, Xu GM, Li CS, Wang BG (2014) Antioxidant metabolites from marine alga-derived fungus Aspergillus wentii en-48. Phytochem Lett 7:120–123 (Article)Google Scholar
  139. 139.
    Baraban EG, Morin JB, Phillips GM, Phillips AJ, Strobel SA, Handelsman J (2013) Xyolide, a bioactive nonenolide from an amazonian endophytic fungus, Xylaria feejeensis. Tetrahedron Lett 54(31):4058–4060 (Article)PubMedCentralPubMedGoogle Scholar
  140. 140.
    Ortega HE, Shen YY, TenDyke K, Ríos N, Cubilla-Ríos L (2014) Polyhydroxylated macrolide isolated from the endophytic fungus Pestalotiopsis mangiferae. Tetrahedron Lett 55:2642–2645Google Scholar
  141. 141.
    Yang SX, Gao JM, Laatsch H, Tian JM, Pescitelli G (2012) Absolute configuration of fusarone, a new azaphilone from the endophytic fungus Fusarium sp. isolated from Melia azedarach, and of related azaphilones. Chirality 24(8):621–627 (Article)PubMedGoogle Scholar
  142. 142.
    Zeng YB, Wang H, Zuo WJ, Zheng B, Yang T, Dai HF et al (2012) A fatty acid glycoside from a marine-derived fungus isolated from mangrove plant Scyphiphora hydrophyllacea. Mar Drugs 10(3):598–603 (Article)PubMedCentralPubMedGoogle Scholar
  143. 143.
    Hawas UW, El-Beih AA, El-Halawany AM (2012) Bioactive anthraquinones from endophytic fungus Aspergillus versicolor isolated from red sea algae. Arch Pharm Res 35(10):1749–1756 (Article)PubMedGoogle Scholar
  144. 144.
    Klaiklay S, Rukachaisirikul V, Phongpaichit S, Pakawatchai C, Saithong S, Buatong J et al (2012) Anthraquinone derivatives from the mangrove-derived fungus Phomopsis sp. psu-ma214. Phytochem Lett 5(4):738–742 (Article)Google Scholar
  145. 145.
    Miao FP, Li XD, Liu XH, Cichewicz RH, Ji NY (2012) Secondary metabolites from an algicolous Aspergillus versicolor strain. Mar Drugs 10(1):131–139 (Article)PubMedCentralPubMedGoogle Scholar
  146. 146.
    Choi JN, Kim J, Ponnusamy K, Lim C, Kim JG, Muthaiya MJ et al (2013) Identification of a new phomoxanthone antibiotic from Phomopsis longicolla and its antimicrobial correlation with other metabolites during fermentation. J Antibiot 66(4):231–233 (Article)PubMedGoogle Scholar
  147. 147.
    Huang ZJ, Yang JX, Lei FH, She ZG, Lin YC (2013) A new xanthone o-glycoside from the mangrove endophytic fungus Phomopsis sp. Chem Nat Compd 49(1):27–30 (Article)Google Scholar
  148. 148.
    Koolen HHF, Menezes LS, Souza MP, Silva FMA, Almeida FGO, de Souza AQL et al (2013) Talaroxanthone, a novel xanthone dimer from the endophytic fungus Talaromyces sp. associated with Duguetia stelechantha (Diels) R. E. Fries. J Braz Chem Soc 24(5):880- + (Article)Google Scholar
  149. 149.
    Calcul L, Waterman C, Ma WS, Lebar MD, Harter C, Mutka T et al (2013) Screening mangrove endophytic fungi for antimalarial natural products. Mar Drugs 11(12):5036–5050 (Article)PubMedCentralPubMedGoogle Scholar
  150. 150.
    Song XQ, Zhang X, Han QJ, Li XB, Li G, Li RJ et al (2013) Xanthone derivatives from Aspergillus sydowii, an endophytic fungus from the liverwort Scapania ciliata s. Lac and their immunosuppressive activities. Phytochem Lett 6(3):318–321 (Article)Google Scholar
  151. 151.
    Cheng MJ, Wu MD, Chen IS, Hsieh SY, Yuan GF (2012) Chemical constituents from the endophytic fungus Annulohypoxylon squamulosum. Chem Nat Compd 48(2):218–220 (Article)Google Scholar
  152. 152.
    Liu HT, Liu SC, Guo LD, Zhang YG, Cui LJ, Ding G (2012) New furanones from the plant endophytic fungus Pestalotiopsis besseyi. Molecules 17(12):14015–14021 (Article)PubMedGoogle Scholar
  153. 153.
    Zhang HQ, Deng ZS, Guo ZY, Tu X, Wang JZ, Zou K (2014) Pestalafuranones f–j, five new furanone analogues from the endophytic fungus Nigrospora sp. bm-2. Molecules 19(1):819–825 (Article)PubMedGoogle Scholar
  154. 154.
    Liu SC, Liu XY, Guo LD, Che YS, Liu L (2013) 2h-pyran-2-one and 2h-furan-2-one derivatives from the plant endophytic fungus Pestalotiopsis fici. Chem Biodivers 10(11):2007–2013 (Article)PubMedGoogle Scholar
  155. 155.
    Chen G, Zhang L, Wang HF, Wu HH, Lu X, Pei YH et al (2013) A new compound along with seven known compounds from an endophytic fungus Aspergillus sp. hs-05. Rec Nat Prod 7(4):320–324 (Article)Google Scholar
  156. 156.
    Wu MD, Cheng MJ, Chen IS, Su YS, Hsieh SY, Chang HS et al (2013) Phytochemical investigation of annulohypoxylon ilanense, an endophytic fungus derived from Cinnamomum species. Chem Biodivers 10(3):493–505 (Article)PubMedGoogle Scholar
  157. 157.
    Cheng MJ, Wu MD, Chen IS, Chen JJ, Hsieh SY, Yuan GF (2013) A new furan-3-one derivative from the endophytic fungus Annulohypoxylon sp. Chem Nat Compd 49(3):446–449 (Article)Google Scholar
  158. 158.
    Wang X, Wang H, Liu T, Xin Z (2014) A pks i gene-based screening approach for the discovery of a new polyketide from Penicillium citrinum salicorn 46. Appl Microbiol Biotechnol (In press). doi:10.1007/s00253-014-5572-3Google Scholar
  159. 159.
    Klaiklay S, Rukachaisirikul V, Phongpaichit S, Buatong J, Preedanon S, Sakayaroj J (2013) Flavodonfuran: a new difuranylmethane derivative from the mangrove endophytic fungus Flavodon flavus psu-ma201. Nat Prod Res 27(19):1722–1726 (Article)PubMedGoogle Scholar
  160. 160.
    Ai HL, Zhang LM, Chen YP, Zi SH, Xiang H, Zhao DK et al (2012) Two new compounds from an endophytic fungus Alternaria solani. J Asian Nat Prod Res 14(12):1144–1148 (Article)PubMedGoogle Scholar
  161. 161.
    Akone SH, El Amrani M, Lin WH, Lai DW, Proksch P (2013) Cytosporins f–k, new epoxyquinols from the endophytic fungus Pestalotiopsis theae. Tetrahedron Lett 54(49):6751–6754 (Article)Google Scholar
  162. 162.
    Wanigesekara W, Wijeratne EMK, Arnold AE, Gunatilaka AAL (2013) 10ʹ-deoxy-10ʹalpha-hydroxyascochlorin, a new cell migration inhibitor and other metabolites from Acremonium sp., a fungal endophyte in Ephedra trifurca. Nat Prod Commun 8(5):601–604 (Article)Google Scholar
  163. 163.
    Asai T, Otsuki S, Taniguchi T, Monde K, Yamashita K, Sakurai H et al (2013) Structures and absolute configurations of short-branched fatty acid dimers from an endophytic fungus of Aloe arborescens. Tetrahedron Lett 54(26):3402–3405 (Article)Google Scholar
  164. 164.
    Ding GZ, Liu J, Wang JM, Fang L, Yu SS (2013) Secondary metabolites from the endophytic fungi Penicillium polonicum and Aspergillus fumigatus. J Asian Nat Prod Res 15(5):446–452 (Article)PubMedGoogle Scholar
  165. 165.
    El-Neketi M, Ebrahim W, Lin WH, Gedara S, Badria F, Saad HEA et al (2013) Alkaloids and polyketides from Penicillium citrinum, an endophyte isolated from the moroccan plant Ceratonia siliqua. J Nat Prod 76(6):1099–1104 (Article)PubMedGoogle Scholar
  166. 166.
    Zheng CJ, Xu LL, Li YY, Han T, Zhang QY, Ming QL et al (2013) Cytotoxic metabolites from the cultures of endophytic fungi from Panax ginseng. Appl Microbiol Biotechnol 97(17):7617–7625 (Article)PubMedGoogle Scholar
  167. 167.
    Zilla MK, Qadri M, Pathania AS, Strobel GA, Nalli Y, Kumar S et al (2013) Bioactive metabolites from an endophytic Cryptosporiopsis sp. inhabiting Clidemia hirta. Phytochemistry 95:291–297PubMedGoogle Scholar
  168. 168.
    Wu Q, Guo Y, Guo ZK, Chu YL, Wang T, Tan RX (2013) Two new cytosporones from the culture of endophytic Phomopsis sp. Chem Nat Compd 48(6):938–941 (Article)Google Scholar
  169. 169.
    Leyte-Lugo M, Gonzalez-Andrade M, Gonzalez MD, Glenn AE, Cerda-Garcia-Rojas CM, Mata R (2012) (+)-ascosalitoxin and vermelhotin, a calmodulin inhibitor, from an endophytic fungus isolated from Hintonia latiflora. J Nat Prod 75(9):1571–1577 (Article)PubMedGoogle Scholar
  170. 170.
    Li JT, Chen QQ, Zeng Y, Wang Q, Zhao PJ (2012) A new phenol compound from endophytic Phomopsis sp. dc01. Nat Prod Res 26(21):2008–2012 (Article)PubMedGoogle Scholar
  171. 171.
    Talontsi FM, Kenla TJN, Dittrich B, Douanla-Meli C, Laatsch H (2012) Paeciloside a, a new antimicrobial and cytotoxic polyketide from Paecilomyces sp. strain caft156. Planta Medica 78(10):1020–1023 (Letter)PubMedGoogle Scholar
  172. 172.
    Wang JF, Lu ZY, Liu PP, Wang Y, Li J, Hong K et al (2012) Cytotoxic polyphenols from the fungus Penicillium expansum 091006 endogenous with the mangrove plant Excoecaria agallocha. Planta Medica 78(17):1861–1866 (Article)PubMedGoogle Scholar
  173. 173.
    Wang LW, Xu BG, Wang JY, Su ZZ, Lin FC, Zhang CL et al (2012) Bioactive metabolites from phoma species, an endophytic fungus from the chinese medicinal plant Arisaema erubescens. Appl Microbiol Biotechnol 93(3):1231–1239 (Article)PubMedGoogle Scholar
  174. 174.
    Sun P, Huo J, Kurtan T, Mandi A, Antus S, Tang H et al (2013) Structural and stereochemical studies of hydroxyanthraquinone derivatives from the endophytic fungus Coniothyrium sp. Chirality 25(2):141–148 (Article)PubMedGoogle Scholar
  175. 175.
    Klaiklay S, Rukachaisirikul V, Sukpondma Y, Phongpaichit S, Buatong J, Bussaban B (2012) Metabolites from the mangrove-derived fungus Xylaria cubensis psu-ma34. Arch Pharm Res 35(7):1127–1131 (Article)PubMedGoogle Scholar
  176. 176.
    Chen R-D, Yan Z, Zou J-H, Wang N, Dai J-G (2014) Rubratoxin c, a new nonadride derivative from an endophytic fungus Penicillium sp. F-14. Chin Chem Lett (In press) (http://dx.doi.org/10.1016/j.cclet.2014.03.040)
  177. 177.
    Wang H, Liu T, Xin Z (2014) A new glucitol from an endophytic fungus Fusarium equiseti salicorn 8. Eur Food Res Technol (In press). doi:10.1007/s00217-014-2230-zGoogle Scholar
  178. 178.
    Ying YM, Shan WG, Zhang LW, Chen Y, Zhan ZJ (2013) Lanostane triterpenes from Ceriporia lacerate hs-zjut-c13a, a fungal endophyte of Huperzia serrata. Helvetica Chimica Acta 96(11):2092–2097 (Article)Google Scholar
  179. 179.
    Ying Y-M, Z.-Z. Z, Zhang L-W, Shan W-G, Wang J-W, Zhan Z-J (2014) Rare c25 steroids produced by Penicillium chrysogenum p1x, a fungal endophyte of Huperzia serrata. Helvetica Chimica Acta 97:95–101Google Scholar
  180. 180.
    Chang DD, Zuo WJ, Mei WL, Dai HF (2012) Metabolites from endophytic fungus a12 of Dracaena cambodiana. J Asian Nat Prod Res 14(6):577–580 (Article)PubMedGoogle Scholar
  181. 181.
    Guo ZK, Yan T, Guo Y, Song YC, Jiao RH, Tan RX et al (2012) P-terphenyl and diterpenoid metabolites from endophytic Aspergillus sp. yxf3. J Nat Prod 75(1):15–21 (Article)PubMedGoogle Scholar
  182. 182.
    Yan T, Guo ZK, Jiang R, Wei W, Wang T, Guo Y et al (2013) New flavonol and diterpenoids from the endophytic fungus Aspergillus sp. yxf3. Planta Medica 79(5):348–352 (Article)PubMedGoogle Scholar
  183. 183.
    Guimaraes DO, Lopes NP, Pupo MT (2012) Meroterpenes isolated from the endophytic fungus Guignardia mangiferae. Phytochem Lett 5(3):519–523 (Article)Google Scholar
  184. 184.
    Mei WL, Zheng B, Zhao YX, Zhong HM, Chen XLW, Zeng YB et al (2012) Meroterpenes from endophytic fungus a1 of mangrove plant Scyphiphora hydrophyllacea. Mar Drugs 10(9):1993–2001 (Article)PubMedCentralPubMedGoogle Scholar
  185. 185.
    Molinar E, Rios N, Spadafora C, Arnold AE, Coley PD, Kursar TA et al (2012) Coibanoles, a new class of meroterpenoids produced by Pycnoporus sanguineus. Tetrahedron Lett 53(8):919–922 (Article)PubMedCentralPubMedGoogle Scholar
  186. 186.
    Liu XH, Miao FP, Li XD, Yin XL, Ji NY (2012) A new sesquiterpene from an endophytic Aspergillus versicolor strain. Nat Prod Commun 7(7):819–820 (Article)PubMedGoogle Scholar
  187. 187.
    Song YX, Wang JJ, Huang HB, Ma L, Wang J, Gu YC et al (2012) Four eremophilane sesquiterpenes from the mangrove endophytic fungus Xylaria sp. bl321. Mar Drugs 10(2):340–348 (Article)PubMedCentralPubMedGoogle Scholar
  188. 188.
    Gubiani JR, Zeraik ML, Oliveira CM, Ximenes VF, Nogueira CR, Fonseca LM et al (2014) Biologically active eremophilane-type sesquiterpenes from Camarops sp., an endophytic fungus isolated from Alibertia macrophylla. J Nat Prod 77(3):668–672 (Article)PubMedGoogle Scholar
  189. 189.
    Deng CM, Huang CH, Wu QL, Pang JY, Lin YC (2013) A new sesquiterpene from the mangrove endophytic fungus Aspergillus terreus (no. Gx7–3b). Nat Prod Res 27(20):1882–1887 (Article)PubMedGoogle Scholar
  190. 190.
    Huang XS, Sun XF, Ding B, Lin M, Liu L, Huang HR et al (2013) A new anti-acetylcholinesterase alpha-pyrone meroterpene, arigsugacin i, from mangrove endophytic fungus Penicillium sp. sk5gw1l of Kandelia candel. Planta Medica 79(16):1572–1575 (Article)PubMedGoogle Scholar
  191. 191.
    Huang XS, Huang HB, Li HX, Sun XF, Huang HR, Lu YJ et al (2013) Asperterpenoid a, a new sesterterpenoid as an inhibitor of Mycobacterium tuberculosis protein tyrosine phosphatase b from the culture of Aspergillus sp. 16–5c. Org Lett 15(4):721–723 (Article)PubMedGoogle Scholar
  192. 192.
    Wu LS, Hu CL, Han T, Zheng CJ, Ma XQ, Rahman K et al (2013) Cytotoxic metabolites from Perenniporia tephropora, an endophytic fungus from Taxus chinensis var. Mairei. Appl Microbiol Biotechnol 97(1):305–315 (Article)PubMedGoogle Scholar
  193. 193.
    Xu YM, Espinosa-Artiles P, Liu MPX, Arnold AE, Gunatilaka AAL (2013) Secoemestrin d, a cytotoxic epitetrathiodioxopiperizine, and emericellenes a-e, five sesterterpenoids from Emericella sp. ast0036, a fungal endophyte of Astragalus lentiginosus. J Nat Prod 76(12):2330–2336 (Article)PubMedCentralPubMedGoogle Scholar
  194. 194.
    Xuan QC, Huang R, Chen YW, Miao CP, Ma KX, Wang T et al (2014) Cyclonerol derivatives from Trichoderma longibrachiatum ym311505. Nat Prod Commun 9(3):313–314 (Article)PubMedGoogle Scholar
  195. 195.
    Zuo WJ, Mn PF, Dong WH, Dai HF, Mei WL (2014) Metabolites from the endophytic fungus hp-1 of Chinese eaglewood. Chin J Nat Med 12(2):151–153 (Article)PubMedGoogle Scholar
  196. 196.
    Wu B, Wu XD, Sun M, Li MH (2013) Two novel tyrosinase inhibitory sesquiterpenes induced by cucl2 from a marine-derived fungus Pestalotiopsis sp. z233. Mar Drugs 11(8):2713–2721 (Article)PubMedCentralPubMedGoogle Scholar
  197. 197.
    Gu W, Qiao C (2012) Furandiones from an endophytic Aspergillus terreus residing in Malus halliana. Chem Pharm Bull 60(11):1474–1477 (Article)PubMedGoogle Scholar
  198. 198.
    Ebrahim W, Kjer J, El Amrani M, Wray V, Lin WH, Ebel R et al (2012) Pullularins e and f, two new peptides from the endophytic fungus Bionectria ochroleuca isolated from the mangrove plant Sonneratia caseolaris. Mar Drugs 10(5):1081–1091 (Article)PubMedCentralPubMedGoogle Scholar
  199. 199.
    Li XJ, Zhang Q, Zhang AL, Gao JM (2012) Metabolites from Aspergillus fumigatus, an endophytic fungus associated with Melia azedarach, and their antifungal, antifeedant, and toxic activities. J Agri Food Chem 60(13):3424–3431 (Article)Google Scholar
  200. 200.
    Liu YX, Ma SG, Wang XJ, Zhao N, Qu J, Yu SS et al (2012) Diketopiperazine alkaloids produced by the endophytic fungus Aspergillus fumigatus from the stem of Erythrophloeum fordii oliv. Helvetica Chimica Acta 95(8):1401–1408 (Article)Google Scholar
  201. 201.
    Kong FD, Wang Y, Liu PP, Dong TH, Zhu WM (2014) Thiodiketopiperazines from the marine-derived fungus Phoma sp. oucmdz-1847. J Nat Prod 77(1):132–137 (Article)PubMedGoogle Scholar
  202. 202.
    Xiao J, Zhang Q, Gao YQ, Tang JJ, Zhang AL, Gao JM (2014) Secondary metabolites from the endophytic Botryosphaeria dothidea of Melia azedarach and their antifungal, antibacterial, antioxidant, and cytotoxic activities. J Agri Food Chem 62(16):3584–3590 (Article)Google Scholar
  203. 203.
    El Amrani M, Debbab A, Aly AH, Wray V, Dobretsov S, Muller WEG et al (2012) Farinomalein derivatives from an unidentified endophytic fungus isolated from the mangrove plant Avicennia marina. Tetrahedron Lett 53(49):6721–6724 (Article)Google Scholar
  204. 204.
    Zhu F, Chen GY, Wu JS, Pan JH (2013) Structure revision and cytotoxic activity of marinamide and its methyl ester, novel alkaloids produced by co-cultures of two marine-derived mangrove endophytic fungi. Nat Prod Res 27(21):1960–1964 (Article)PubMedGoogle Scholar
  205. 205.
    Ding G, Chen L, Chen A, Tian XH, Chen XD, Zhang HW et al (2012) Trichalasins c and d from the plant endophytic fungus Trichoderma gamsii. Fitoterapia 83(3):541–544 (Article)PubMedGoogle Scholar
  206. 206.
    Ortega HE, Graupner PR, Asai Y, TenDyke K, Qiu DY, Shen YYC et al (2013) Mycoleptodiscins a and b, cytotoxic alkaloids from the endophytic fungus Mycoleptodiscus sp. f0194. J Nat Prod 76(4):741–744 (Article)PubMedGoogle Scholar
  207. 207.
    Luo DQ, Chen YP, Zhang J, Shi BZ, Yang ZQ, Chen C (2013) A new glycine derivative and a new indole alkaloid from the fermentation broth of the plant endophytic fungus Pestalotiopsis podocarpi isolated from the Chinese podocarpaceae plant Podocarpus macrophyllus. Helvetica Chimica Acta 96(2):309–312 (Article)Google Scholar
  208. 208.
    Zang L-Y, Wei W, Wang T, Guo Y, Tan R-X, Ge H-M (2012) Isochromophilones from an endophytic fungus Diaporthe sp. Nat Prod Bioprospect 2:117–120>PubMedCentralGoogle Scholar
  209. 209.
    Talontsi FM, Tatong MDK, Dittrich B, Douanla-Meli C, Laatsch H (2013) Structures and absolute configuration of three alpha-pyrones from an endophytic fungus Aspergillus niger. Tetrahedron 69(34):7147–7151 (Article)>Google Scholar
  210. 210.
    Ebrahim W, Aly AH, Wray V, Mandi A, Teiten MH, Gaascht F et al (2013) Embellicines a and b: absolute configuration and nf-kappa b transcriptional inhibitory activity. J Med Chem 56(7):2991–2999 (Article)>PubMedGoogle Scholar
  211. 211.
    Zhou XF, Lin XP, Ma WL, Fang W, Chen ZF, Yang B et al (2014) A new aromatic amine from fungus Pestalotiopsis vaccinii. Phytochem Lett 7:35–37 (Article)>Google Scholar
  212. 212.
    Intaraudom C, Boonyuen N, Suvannakad R, Rachtawee P, Pittayakhajonwut P (2013) Penicolinates a–e from endophytic Penicillium sp. bcc16054. Tetrahedron Lett 54(8):744–748 (Article)Google Scholar

Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • Fernanda O. Chagas
    • 1
  • Andrés Mauricio Caraballo-Rodriguez
    • 1
  • Mônica T. Pupo
    • 1
    Email author
  1. 1.School of Pharmaceutical Sciences of Ribeirão Preto, Department of Pharmaceutical SciencesUniversity of São PauloRibeirão PretoBrazil

Personalised recommendations