Skip to main content

Advertisement

SpringerLink
Log in

Chemical Diversity of Secondary Metabolites Produced by Brazilian Endophytic Fungi

  • Review Article
  • Published:
Current Microbiology Aims and scope Submit manuscript

Abstract

Endophytes are microorganisms that live inside vegetal tissues without causing any loss to the host plant. They display wide biosynthetic capacity when producing several bioactive secondary metabolites, whose induction could be related to activation of genes, which might be silent or expressed depending on the geographic characteristics from where the endophytic was isolated. The extraordinary richness of the Brazilian biodiversity has encouraged several research groups in the endophytic bioprospecting. This review covers natural products reported by studies on from the Brazilian endophytic fungi cultures and classified them into three chemical classes (terpenes, phenolic, and nitrogen-containing compounds). For discussion purposes, Principal Component Analysis (PCA) was used as an unsupervised explorative method to evaluate the chemical variation in the Brazilian endophyte dataset. In addition, the dendrogram from the Hierarchical Clustering Analysis (HCA) confirmed the PCA results, and HCA could identify some main endophytic clusters. Our analysis clarified how the secondary metabolites were distributed in the different Brazilian endophyte strains, and this information will be a reliable guide that will support researchers to design microbial culture strategies.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Fig. 13
Fig. 14
Fig. 15

Similar content being viewed by others

References

  1. Newman DJ, Cragg GM (2012) Natural products as sources of new drugs over the 30 years from 1981 to 2010. J Nat Prod 75:311–335

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Rajamanikyam M, Vadlapudi V, Amanchy R, Upadhyayula SM (2017) Endophytic fungi as novel resources of natural therapeutics. Brazilian Arch Biol Technol 60:1–26

    Article  CAS  Google Scholar 

  3. Bary A de (1866) Morphologie und physiologie der pilze, flechten, und myxomyceten. In: Hofmeister’s handbook of physiological botany. Leipzig, Germany, pp 1831–1888.

  4. Bacon CW, White JF (2000) Microbial endophytes. Marcel Dekker, New York, USA

    Book  Google Scholar 

  5. Schulz B, Boyle C, Draeger S et al (2002) Endophytic fungi: a source of novel biologically active secondary metabolites. Mycol Res 106:996–1004

    Article  CAS  Google Scholar 

  6. Kaul S, Gupta S, Ahmed M, Dhar MK (2012) Endophytic fungi from medicinal plants: a treasure hunt for bioactive metabolites. Phytochem Rev 11:487–505

    Article  CAS  Google Scholar 

  7. Zhang HW, Song YC, Tan RX (2006) Biology and chemistry of endophytes. Nat Prod Rep 23:753–771

    Article  CAS  PubMed  Google Scholar 

  8. Saikkonen K, Wäli P, Helander M, Faeth SH (2004) Evolution of endophyte-plant symbioses. Trends Plant Sci 9:275–280

    Article  CAS  PubMed  Google Scholar 

  9. Rodriguez RJ, White JF Jr, Arnold AE, Redman RS (2009) Fungal endophytes: diversity and functional roles. New Phytol 182:314–330

    Article  CAS  PubMed  Google Scholar 

  10. Panaccione DG, Beaulieu WT, Cook D (2014) Bioactive alkaloids in vertically transmitted fungal endophytes. Funct Ecol 28:299–314

    Article  Google Scholar 

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

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. Robinson T, Singh D, Nigam P (2001) Solid-state fermentation: a promising microbial technology for secondary metabolite production. Microbiol Biotechnol 55:284–289

    Article  CAS  Google Scholar 

  13. Vaz ABM, Fonseca PLC, Badotti F et al (2018) A multiscale study of fungal endophyte communities of the foliar endosphere of native rubber trees in eastern amazon. Sci Rep 8:16151

    Article  PubMed  PubMed Central  CAS  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  15. Smith D, Fritze D, Stackebrandt E (2013) Public service collections and biological resource centers of microorganisms. The prokaryotes. Springer Berlin Heidelberg, Berlin, pp 267–304

    Chapter  Google Scholar 

  16. Stackebrandt E, Smith D, Casaregola S et al (2014) Deposit of microbial strains in public service collections as part of the publication process to underpin good practice in science. Springerplus 3:208–212

    Article  PubMed  PubMed Central  Google Scholar 

  17. Kliebenstein DJ (2004) Secondary metabolites and plant/environment interactions: a view through Arabidopsis thaliana tinged glasses. Plant Cell Environ 27:675–684

    Article  CAS  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  19. Cota BB, Rosa LH, Caligiorne RB et al (2008) Altenusin, a biphenyl isolated from the endophytic fungus Alternaria sp., inhibits trypanothione reductase from trypanosoma cruzi. FEMS Microbiol Lett 285:177–182

    Article  CAS  PubMed  Google Scholar 

  20. Chagas FO, Dias LG, Pupo MT (2016) New perylenequinone derivatives from the endophytic fungus Alternaria tenuissima SS77. Tetrahedron Lett 57:3185–3189

    Article  CAS  Google Scholar 

  21. Maciel OMC, Tavares RSN, Caluz DRE et al (2018) Photoprotective potential of metabolites isolated from algae-associated fungi Annulohypoxylon stygium. J Photochem Photobiol B Biol 178:316–322

    Article  CAS  Google Scholar 

  22. De AMR, Somensi A, Araujo AR et al (2016) Compounds of Anthostomella brabeji, an endophytic fungus isolated from Paepalanthus planifolius (Eriocaulaceae). J Braz Chem Soc 27:1048–1054

    Google Scholar 

  23. Feitosa AO, Dias AC, Ramos GC et al (2016) Lethality of cytochalasin B and other compounds isolated from fungus Aspergillus sp. (Trichocomaceae) endophyte of Bauhinia guianensis (Fabaceae). Rev Argent Microbiol 48:259–263

    PubMed  Google Scholar 

  24. Pinheiro EAA, Carvalho JM, Dos Santos DCP et al (2013) Antibacterial activity of alkaloids produced by endophytic fungus Aspergillus sp. EJC08 isolated from medical plant Bauhinia guianensis. Nat Prod Res 27:1633–1638

    Article  CAS  PubMed  Google Scholar 

  25. da Silva IP, Brissow E, Kellner Filho LC et al (2017) Bioactive compounds of Aspergillus terreus-F7, an endophytic fungus from Hyptis suaveolens (L.) Poit. World J Microbiol Biotechnol 33:62–72

    Article  PubMed  CAS  Google Scholar 

  26. Gubiani JR, Teles HL, Silva GH et al (2017) Cyclo-(trp-phe) diketopiperazines from the endophytic fungus Aspergillus versicolor isolated from Piper aduncum. Quim Nova 40:138–142

    CAS  Google Scholar 

  27. Gubiani JR, Habeck TR, Chapla VM et al (2016) One strain-many compounds (OSMAC) method for production of phenolic compounds using Camarops sp., an endophytic fungus from Alibertia macrophylla (Rubiaceae). Quim Nova 39:1221–1224

    CAS  Google Scholar 

  28. Gubiani JR, Nogueira CR, Pereira MDP et al (2016) Rearranged sesquiterpenes and branched polyketides produced by the endophyte Camarops sp. Phytochem Lett 17:251–257

    Article  CAS  Google Scholar 

  29. Gubiani JR, Zeraik ML, Oliveira CM et al (2014) Biologically active eremophilane-type sesquiterpenes from Camarops sp., an endophytic fungus isolated from Alibertia macrophylla. J Nat Prod 77:668–672

    Article  CAS  PubMed  Google Scholar 

  30. De OCM, Silva GH, Regasini LO et al (2011) Xylarenones C–E and an unprecedented dihydrofuran derivative from an endophytic fungus isolated from Alibertia macrophylla (Rubiaceae). J Nat Prod 74:1353–1357

    Article  CAS  Google Scholar 

  31. De Medeiros LS, Murgu M, De Souza AQL, Rodrigues-Fo E (2011) Antimicrobial depsides produced by cladosporium uredinicola, an endophytic fungus isolated from Psidium guajava fruits. Helv Chim Acta 94:1077–1084

    Article  CAS  Google Scholar 

  32. de Medeiros LS, Sampaio OM, Silva MF, das GF da, et al (2012) Evaluation of herbicidal potential of depsides from Cladosporium uredinicola, an endophytic fungus found in guava fruit. J Braz Chem Soc 23:1551–1557

    Article  Google Scholar 

  33. Campos FF, Rosa LH, Cota BB et al (2008) Leishmanicidal metabolites from Cochliobolus sp., an endophytic fungus isolated from Piptadenia adiantoides (Fabaceae). PLoS Negl Trop Dis 2:1–11

    Article  CAS  Google Scholar 

  34. Chagas FO, Dias LG, Pupo MT (2013) A mixed culture of endophytic fungi increases production of antifungal polyketides. J Chem Ecol 39:1335–1342

    Article  CAS  PubMed  Google Scholar 

  35. Chagas FO, Pupo MT (2018) Chemical interaction of endophytic fungi and actinobacteria from Lychnophora ericoides in co-cultures. Microbiol Res 212–213:10–16

    Article  PubMed  CAS  Google Scholar 

  36. Chagas FO, Caraballo-Rodríguez AM, Dorrestein PC, Pupo MT (2017) Expanding the chemical repertoire of the endophyte Streptomyces albospinus RLe7 reveals amphotericin B as an inducer of a fungal phenotype. J Nat Prod 80:1302–1309

    Article  CAS  PubMed  Google Scholar 

  37. Chapla VM, Zeraik ML, Cafeu MC et al (2018) Griseofulvin, diketopiperazines and cytochalasins from endophytic fungi Colletotrichum crassipes and Xylaria sp., and their antifungal, antioxidant and anticholinesterase activities. J Braz Chem Soc 29:1707–1713

    CAS  Google Scholar 

  38. Chapla VM, Zeraik ML, Leptokarydis IH et al (2014) Antifungal compounds produced by Colletotrichum gloeosporioides, an endophytic fungus from Michelia champaca. Molecules 19:19243–19252

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  39. Carvalho JM, da Paixão LKO, Dolabela MF et al (2016) Phytosterols isolated from endophytic fungus Colletotrichum gloeosporioides (Melanconiaceae). Acta Amaz 46:69–72

    Article  CAS  Google Scholar 

  40. Guimarães DO, Borges WS, Vieira NJ et al (2010) Diketopiperazines produced by endophytic fungi found in association with two asteraceae species. Phytochemistry 71:1423–1429

    Article  PubMed  CAS  Google Scholar 

  41. Teles HL, Silva GH, Castro-Gamboa I et al (2005) Benzopyrans from Curvularia sp., an endophytic fungus associated with Ocotea corymbosa (Lauraceae). Phytochemistry 66:2363–2367

    Article  CAS  PubMed  Google Scholar 

  42. Abreu LM, Phipps RK, Pfenning LH et al (2010) Cytosporones O, P and Q from an endophytic Cytospora sp. Tetrahedron Lett 51:1803–1805

    Article  CAS  Google Scholar 

  43. Polonio JC, dos Ribeiro MA, S, Rhoden SA, et al (2016) 3-Nitropropionic acid production by the endophytic Diaporthe citri: molecular taxonomy, chemical characterization, and quantification under pH variation. Fungal Biol 120:1600–1608

    Article  CAS  PubMed  Google Scholar 

  44. Specian V, Sarragiotto MH, Pamphile JA, Clemente E (2012) Chemical characterization of bioactive compounds from the endophytic fungus Diaporthe helianthi isolated from luehea divaricata. Brazilian J Microbiol 43:1174–1182

    Article  CAS  Google Scholar 

  45. Brissow ER, da Silva IP, de Siqueira KA et al (2017) 18-Des-hydroxy cytochalasin: an antiparasitic compound of Diaporthe phaseolorum-92C, an endophytic fungus isolated from Combretum lanceolatum pohl ex eichler. Parasitol Res 116:1823–1830

    Article  PubMed  Google Scholar 

  46. Sebastianes FLS, Cabedo N, El AN et al (2012) 3-Hydroxypropionic acid as an antibacterial agent from endophytic fungi Diaporthe phaseolorum. Curr Microbiol 65:622–632

    Article  CAS  PubMed  Google Scholar 

  47. Mandavid H, Rodrigues AMS, Espindola LS et al (2015) Secondary metabolites isolated from the amazonian endophytic fungus Diaporthe sp. SNB-GSS10. J Nat Prod 78:1735–1739

    Article  CAS  PubMed  Google Scholar 

  48. de Medeiros AG, Savi DC, Mitra P et al (2018) Bioprospecting of Diaporthe terebinthifolii LGMF907 for antimicrobial compounds. Folia Microbiol 63:499–505

    Article  CAS  Google Scholar 

  49. Da Silva Araújo FD, De Lima Fávaro LC, Araújo WL et al (2012) Epicolactone-natural product isolated from the sugarcane endophytic fungus Epicoccum nigrum. Eur J Org Chem 27:5225–5230

    Article  CAS  Google Scholar 

  50. Proença Barros FA, Rodrigues-Filho E (2005) Four spiroquinazoline alkaloids from Eupenicillium sp. isolated as an endophytic fungus from leaves of Murraya paniculata (Rutaceae). Biochem Syst Ecol 33:257–268

    Article  CAS  Google Scholar 

  51. Souza ADL, Rodrigues-Filho E, Souza AQL et al (2008a) A new guaiane mannoside from a eutypa-like fungus isolated from Murraya paniculata in Brazil. J Braz Chem Soc 19:1321–1325

    Article  CAS  Google Scholar 

  52. Pinheiro EAA, Pina JRS, Feitosa AO et al (2017) Bioprospecting of antimicrobial activity of extracts of endophytic fungi from Bauhinia guianensis. Rev Argent Microbiol 49:3–6

    PubMed  Google Scholar 

  53. Nascimento AM, do, Conti R, Turatti ICC, et al (2012) Bioactive extracts and chemical constituents of two endophytic strains of Fusarium oxysporum. Brazilian J Pharmacogn 22:1276–1281

    Article  CAS  Google Scholar 

  54. Campos FF, Sales Junior PA, Romanha AJ et al (2015) Bioactive endophytic fungi isolated from Caesalpinia echinata Lam. (Brazilwood) and identification of beauvericin as a trypanocidal metabolite from Fusarium sp. Mem Inst Oswaldo Cruz 110:65–74

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  55. Campos FF, Johann S, Cota BB et al (2011) Antifungal activity of trichothecenes from Fusarium sp. against clinical isolates of Paracoccidioides brasiliensis. Mycoses 54:122–129

    Article  Google Scholar 

  56. Guimarães DO, Borges WS, Kawano CY et al (2008) Biological activities from extracts of endophytic fungi isolated from Viguiera arenaria and Tithonia diversifolia. FEMS Immunol Med Microbiol 52:134–144

    Article  PubMed  CAS  Google Scholar 

  57. Guimarães DO, Lopes NP, Pupo MT (2012) Meroterpenes isolated from the endophytic fungus Guignardia mangiferae. Phytochem Lett 5:519–523

    Article  CAS  Google Scholar 

  58. Rodrigues-Heerklotz KF, Drandarov K, Heerklotz J et al (2001) Guignardic acid, a novel type of secondary metabolite produced by the endophytic fungus Guignardia sp.: isolation, structure elucidation, and asymmetric synthesis. Helv Chim Acta 84:3766–3772

    Article  CAS  Google Scholar 

  59. Savi DC, Shaaban KA, Vargas N et al (2014) Microbispora sp. LGMB259 endophytic actinomycete isolated from Vochysia divergens (Pantanal, Brazil) producing β-carbolines and indoles with biological activity. Curr Microbiol 70:345–354

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  60. Andrioli WJ, Silva TM, Da Silva VB et al (2012) The fungal metabolite eugenitin as additive for Aspergillus niveus glucoamylase activation. J Mol Catal B Enzym 74:156–161

    Article  CAS  Google Scholar 

  61. Cota BB, Tunes LG, Maia DNB et al (2018) Leishmanicidal compounds of nectria pseudotrichia, an endophytic fungus isolated from the plant Caesalpinia echinata (Brazilwood). Mem Inst Oswaldo Cruz 113:102–110

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  62. Gallo MBC, Chagas FO, Almeida MO et al (2009) Endophytic fungi found in association with Smallanthus sonchifolius (Asteraceae) as resourceful producers of cytotoxic bioactive natural products. J Basic Microbiol 49:142–151

    Article  CAS  PubMed  Google Scholar 

  63. Fill TP, Asenha HBR, Marques AS et al (2013) Time course production of indole alkaloids by an endophytic strain of Penicillium brasilianum cultivated in rice. Nat Prod Res 27:967–974

    Article  CAS  PubMed  Google Scholar 

  64. Fill TP, dos Santos RMG, Barisson A et al (2009) Co-Production of bisphenylpropanoid amides and meroterpenes by an endophytic Penicillium brasilianum found in the root bark of melia azedarach. Zeitschrift fur Naturforsch 64:355–360

    Article  CAS  Google Scholar 

  65. Da Silva JV, Fill TP, Lotufo LV et al (2014) Biosynthesis of bromoroquefortines in a high saline medium by Penicillium chrysogenum, a terrestrial endophyte collected from Coffea arabica. Helv Chim Acta 97:1345–1353

    Article  CAS  Google Scholar 

  66. Valente AMMP, Ferreira AG, Daolio C et al (2013) Production of 5-hydroxy-7-methoxy-4-methylphthalide in a culture of Penicillium crustosum. An Acad Bras Cienc 85:487–496

    Article  CAS  PubMed  Google Scholar 

  67. Da Silva JV, Fill TP, Da Silva BF, Rodrigues-Fo E (2013) Diclavatol and tetronic acids from Penicillium griseoroseum. Nat Prod Res 27:9–16

    Article  PubMed  CAS  Google Scholar 

  68. Marinho AM, do R, Marinho PSB, Filho ER, (2009) Esteroides produzidos por Penicillium herquei, um fungo endofítico isolado dos frutos de Melia azedarach (Meliaceae). Quim Nova 32:1710–1712

    Article  CAS  Google Scholar 

  69. Marinho AM, do R, Rodrigues-Filho E, Moitinho M da LR, Santos LS, (2005) Biologically active polyketides produced by Penicillium janthinellum isolated as an endophytic fungus from fruits of Melia azedarach. J Braz Chem Soc 16:280–283

    Article  Google Scholar 

  70. Pastre R, Marinho AMR, Rodrigues-Filho E et al (2007) Diversidade de policetídeos produzidos por espécies de Penicillium isoladas de Melia azedarach e Murraya paniculata. Quim Nova 30:1867–1871

    Article  CAS  Google Scholar 

  71. Koolen HHF, Soares ER, da Silva FMA et al (2012) An antimicrobial alkaloid and other metabolites produced by Penicillium sp. an endophytic fungus isolated from Mauritia flexuosa L. f. Quim Nova 35:771–774

    Article  CAS  Google Scholar 

  72. Fill TP, Pereira GK, dos Santos RMG, Rodrigues E (2007) Four additional meroterpenes produced by Penicillium sp. found in association with Melia azedarach. Possible biosynthetic intermediates to austin. Verlag der Zeitschrift für Naturforsch 62(8):1035–1044

    Article  CAS  Google Scholar 

  73. Oliveira CM, Silva GH, Regasini L et al (2009) Bioactive metabolites produced by Penicillium sp.1 and sp.2, two endophytes associated with Alibertia macrophylla (Rubiaceae). Zeitschrift für Naturforsch 64:824–830

    Article  CAS  Google Scholar 

  74. Teles HL, Sordi R, Silva GH et al (2006) Aromatic compounds produced by Periconia atropurpurea, an endophytic fungus associated with Xylopia aromatica. Phytochemistry 67:2686–2690

    Article  CAS  PubMed  Google Scholar 

  75. Oliveira MN, Santos LS, Guilhon GMSP et al (2011) Novel anthraquinone derivatives produced by Pestalotiopsis guepinii, an endophytic of the medicinal plant Virola michelii (Myristicaceae). J Braz Chem Soc 22:993–996

    Article  CAS  Google Scholar 

  76. De Souza EMC, Da Silva EL, Marinho AMR, Marinho PSB (2016) (4S)-4, 8-dihydroxy-1-tetralone and other chemical constituents from Pestalotiopsis sp. EJC07, endophytic from Bauhinia guianensis. An Acad Bras Cienc 88:29–33

    Article  PubMed  CAS  Google Scholar 

  77. Silva GH, Zeraik ML, De Oliveira CM et al (2017) Lactone derivatives produced by a Phaeoacremonium sp., an endophytic fungus from Senna spectabilis. J Nat Prod 80:1674–1678

    Article  CAS  PubMed  Google Scholar 

  78. de Borges W, S, Pupo MT, (2006) Novel anthraquinone derivatives produced by Phoma sorghina, an endophyte found in association with the medicinal plant Tithonia diversifolia (Asteraceae). J Braz Chem Soc 17:929–934

    Article  CAS  Google Scholar 

  79. Silva GH, Teles HL, Trevisan HC et al (2005) New bioactive metabolites produced by Phomopsis cassiae. J Brazilian Chem Soc 16:1463–1466

    Article  CAS  Google Scholar 

  80. Silva GH, Teles HL, Zanardi LM et al (2006) Cadinane sesquiterpenoids of Phomopsis cassiae, an endophytic fungus associated with cassia spectabilis (Leguminosae). Phytochemistry 67:1964–1969

    Article  CAS  PubMed  Google Scholar 

  81. Zanardi LM, da Bolzani V, S, Cavalheiro AJ, et al (2012) Sesquiterpenos produzidos pelo fungo endofítico Phomopsis cassiae com atividade antifúngica e inibidora de acetilcolinesterase. Quim Nova 35:2233–2236

    Article  CAS  Google Scholar 

  82. Pavão GB, Venâncio VP, de Oliveira ALL et al (2016) Differential genotoxicity and cytotoxicity of phomoxanthone a isolated from the fungus Phomopsis longicolla in HL60 cells and peripheral blood lymphocytes. Toxicol Vitr 37:211–217

    Article  CAS  Google Scholar 

  83. Erbert C, Lopes AA, Yokoya NS et al (2012) Antibacterial compound from the endophytic fungus Phomopsis longicolla isolated from the tropical red seaweed Bostrychia radicans. Bot Mar 55:435–440

    Article  CAS  Google Scholar 

  84. Flores AC, Pamphile JA, Sarragiotto MH, Clemente E (2013) Production of 3-nitropropionic acid by endophytic fungus Phomopsis longicolla isolated from Trichilia elegans A. JUSS ssp. elegans and evaluation of biological activity. World J Microbiol Biotechnol 29:923–932

    Article  CAS  PubMed  Google Scholar 

  85. Chapla VM, Zeraik ML, Ximenes VF et al (2014) Bioactive secondary metabolites from Phomopsis sp., an endophytic fungus from Senna spectabilis. Molecules 19:6597–6608

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  86. Morandini LMB, Neto AT, Pedroso M et al (2016) Lanostane-type triterpenes from the fungal endophyte Scleroderma UFSMSc1 (Persoon) fries. Bioorganic Med Chem Lett 26:1173–1176

    Article  CAS  Google Scholar 

  87. De Medeiros LS, Abreu LM, Nielsen A et al (2015) Dereplication-guided isolation of depsides thielavins S-T and lecanorins D-F from the endophytic fungus Setophoma sp. Phytochemistry 111:154–162

    Article  PubMed  CAS  Google Scholar 

  88. Koolen HHF, Souza MP, Silva FMA et al (2013) Talaroxanthone, a novel xanthone dimer from the endophytic fungus Talaromyces sp. associated with Duguetia stelechantha (Diels) R. E. Fries Hector J Braz Chem Soc 24:880–883

    CAS  Google Scholar 

  89. Da Silva PHF, De Souza MP, Bianco EA et al (2018) Antifungal polyketides and other compounds from amazonian endophytic Talaromyces fungi. J Braz Chem Soc 29:622–630

    Article  CAS  Google Scholar 

  90. do Nascimento JS, Silva FM, Magallanes-Noguera CA, et al (2020) Natural trypanocidal product produced by endophytic fungi through co-culturing. Folia Microbiol 65:323–328

    Article  CAS  Google Scholar 

  91. Souza ADL, Rodrigues-Filho E, Souza AQL et al (2008b) Koninginins, phospholipase A2 inhibitors from endophytic fungus Trichoderma koningii. Toxicon 51:240–250

    Article  CAS  PubMed  Google Scholar 

  92. Caraballo-Rodríguez AM, Mayor CA, Chagas FO, Pupo MT (2017) Amphotericin B as an inducer of griseofulvin-containing guttate in the endophytic fungus Xylaria cubensis FLe9. Chemoecology 27:177–185

    Article  CAS  Google Scholar 

  93. Amaral LS, Rodrigues-Filho E (2010) Two novel eremophilane sesquiterpenes from an endophytic Xylariaceous fungus isolated from leaves of Cupressus lusitanica. J Braz Chem Soc 21:1446–1450

    Article  CAS  Google Scholar 

  94. Cafêu MC, Silva GH, Teles HL et al (2005) Substâncias antifúngicas de Xylaria sp., um fungo endofítico isolado de Palicourea marcgravii (Rubiaceae). Quim Nova 28:991–995

    Article  Google Scholar 

  95. Silva GH, de Oliveira CM, Teles HL et al (2010) Citocalasinas produzidas por Xylaria sp., um fungo endofítico de Piper aduncum (Piperaceae). Quim Nova 33:2038–2041

    Article  CAS  Google Scholar 

  96. Silva GH, De Oliveira CM, Teles HL et al (2010) Sesquiterpenes from Xylaria sp., an endophytic fungus associated with Piper aduncum (Piperaceae). Phytochem Lett 3:164–167

    Article  CAS  Google Scholar 

  97. Oliveira CM, Regasini LO, Silva GH et al (2011) Dihydroisocoumarins produced by Xylaria sp. and Penicillium sp., endophytic fungi associated with Piper aduncum and Alibertia macrophylla. Phytochem Lett 4:93–96

    Article  CAS  Google Scholar 

  98. Elias LM, Fortkamp D, Sartori SB et al (2018) The potential of compounds isolated from Xylaria spp. as antifungal agents against anthracnose. Brazilian J Microbiol 49(4):4–11

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by “Conselho Nacional de Desenvolvimento Científico e Tecnológico” (Grant 406413/2018-5).

Author information

Authors and Affiliations

  1. Department of Organic Chemistry, Chemistry Institute, Federal University of Bahia, Barão de Jeremoabo 147, Salvador, BA, 40170-115, Brazil

    Bruno A. Ribeiro & Eliane O. Silva

  2. Department of Analytical Chemistry, Chemistry Institute, Federal University of Bahia, Barão de Jeremoabo 147, Salvador, BA, 40170-115, Brazil

    Thiara B. da Mata & Gisele A. B. Canuto

Authors
  1. Bruno A. Ribeiro
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Thiara B. da Mata
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Gisele A. B. Canuto
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Eliane O. Silva
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

BAR was responsible for revision of literature and data compilation. TBM and GABC made the statistical analysis. EOS designed the study and wrote the paper.

Corresponding author

Correspondence to Eliane O. Silva.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ribeiro, B.A., da Mata, T.B., Canuto, G.A.B. et al. Chemical Diversity of Secondary Metabolites Produced by Brazilian Endophytic Fungi. Curr Microbiol 78, 33–54 (2021). https://doi.org/10.1007/s00284-020-02264-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00284-020-02264-0

Search

Navigation