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The genus Diaporthe: a rich source of diverse and bioactive metabolites

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Abstract

The genus Diaporthe (asexual state: Phomopsis) comprises pathogenic, endophytic and saprobic species with both temperate and tropical distributions. Although species of Diaporthe have in the past chiefly been distinguished based on host association, studies have confirmed several taxa to have wide host ranges, suggesting that they move freely between hosts, frequently co-colonizing diseased or dead tissue, while some species are known to be host-specific. They are also very frequently isolated as endophytes of seed plants. Due to their importance as plant pathogens, the genus has been thoroughly investigated for secondary metabolites, including during screening programs aimed at the discovery of novel bioactive natural products, but the respective information has never been compiled. Therefore, we have examined the relevant literature to explore and highlight the major classes of metabolites of Diaporthe and their Phomopsis conidial states. These fungi predominantly produce a large number of polyketides, but cytochalasins and other types of commonly encountered fungal secondary metabolites are also predominant in some species. Interestingly, not a single metabolite which is also known from the host plant has ever been isolated as a major component from an endophytic Diaporthe strain, despite the fact that many of the recent studies were targeting endophytic fungi of medicinal plants.

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References

  • Abreu LM, Costa SS, Pfennig LH, Takahashi JA, Larsen TO, Andersen B (2012) Chemical and molecular characterization of Phomopsis and cytospora-like endophytes from different host plants in Brazil. Fungal Biol 116(2):249–260

    Article  CAS  PubMed  Google Scholar 

  • Adelin E, Servy C, Cortial S, Lévaique H, Martin M, Retailleau P, Goff GL, Bussaban, Lumyong BS, Ouazzan J (2011) Isolation, structure elucidation and biological activity of metabolites from Sch-642305-producing endophytic fungus Phomopsis sp. CMU-LMA. Phytochemistry 72:2406–2412

    Article  CAS  PubMed  Google Scholar 

  • Adelin E, Martin M, Cortial S, Retailleau P, Lumyong S, Ouazzani J (2013) Bioactive polyketides isolated from agar-supported fermentation of Phomopsis sp. CMU-LMA, taking advantage of the scale-up device, Platotex. Phytochemistry 93:170–175

    Article  CAS  PubMed  Google Scholar 

  • Agusta A, Ohashi K, Shibuya H (2006) bisanthraquinone metabolites produced by the endophytic fungus Diaporthe sp. Chem Pharm Bull 54(4):579–582

    Article  CAS  PubMed  Google Scholar 

  • Ahmed I, Hussain H, Schulz B, Draeger S, Padula D, Pescitelli G, van Ree T, Krohn K (2011) Three new antimicrobial metabolites from the endophytic fungus Phomopsis sp. Eur J Org Chem 15:2867–2873

    Article  CAS  Google Scholar 

  • Anupam B, Shamima A, Nikoleta B, Marjorie P (2011) Triterpenoids as potential agents for the chemoprevention and therapy of breast cancer. Front Biosci 16:980–996

    Article  Google Scholar 

  • Arai I, Shiomi K, Tomoda H, Tabata N, Yang DY, Masuma R, Kawakubo T, Omura S (1995) Mophilones III - VI, inhibitors of Acyl-CoA : cholesterol acyltransferase produced by Penicillium multicolor FO-3216. J Antibiot 48:696–702

    Article  CAS  PubMed  Google Scholar 

  • Avantaggiato G, Solfrizzo M, Tosi L, Zazzerini A, Fanizzi FP, Visconti A (1999) Isolation and characterization of phytotoxic compounds produced by Phomopsis helianthi. Nat Toxins 7(3):119–127

    Article  CAS  PubMed  Google Scholar 

  • Botella L, Diez JJ (2011) Phylogenic diversity of fungal endophytes in Spanish stands of Pinus halepensis. Fungal Divers 47:9–18

    Article  Google Scholar 

  • Brady SF, Singh MP, Janso JE, Clardy J (2000) Cytoskyrins A and B, new BIA active bisanthraquinones isolated from an endophytic fungus. Org Lett 2(25):4047–4049

    Article  CAS  PubMed  Google Scholar 

  • Brenner SL, Korn ED (1980) The effects of cytochalasins on actin polymerization and actin ATPase provide insights into the mechanism of polymerization. J Biol Chem 255(3):841–844

    CAS  PubMed  Google Scholar 

  • Brown SG, Jansma MJ, Hoye TR (2012) Case study of empirical and computational chemical shift analyses: reassignment of the relative configuration of phomopsichalasin to that of diaporthichalasin. J Nat Prod 75(7):1326–1331

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Bungihan ME, Tan MA, Kitajima M, Kogure N, Franzblau SG, dela Cruz DEE, Takayama H, Nonato GM (2011) Bioactive metabolites of Diaporthe sp. P133, an endophytic fungus isolated from Pandanus amaryllifolius. J Nat Med 65(3):606–609

    Article  CAS  PubMed  Google Scholar 

  • Bunyapaiboonsri T, Yoiprommarat S, Srikitikulchai P, Srichomthong K, Lumyong S (2010) Oblongolides from the endophytic fungus Phomopsis sp. BCC 9789. J Nat Prod 73:55–59

    Article  CAS  PubMed  Google Scholar 

  • Cai P, Smith D, Cunningham B, Brown-Shimer S, Katz B, Pearce C, Venables D, Houck D (2012) Epolones: novel sesquiterpene-tropolones from fungus OS-F69284 that induce erythropoietin in human cells. J Nat Prod 61:791–795

    Article  Google Scholar 

  • Calcul L, Waterman C, Ma WS, Lebar MD, Harter C, Mutka T, Morton L, Maignan P, Olphen A, Kyle DE, Vrijmoed L, Pang K, Pearce C, Baker B (2013) Screening mangrove endophytic fungi for antimalarial natural products. Mar Drugs 11(12):5036–5050

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Chen Y, Pan J, Xu F, Liu F, Yang J, Huang C, Xu C, Lu Y, Cai X, She Z, Lin (2010) A new indene derivative from the marine fungus Phomopsis sp. (No. GX7-4A). Chem Nat Compd 46:230–232

    Article  CAS  Google Scholar 

  • Choi JN, Kim J, Ponnusamy K, Lim C, Kim JG, Muthaiya MJ, Lee C (2013a) Identification of a new phomoxanthone antibiotic from Phomopsis longicolla and its antimicrobial correlation with other metabolites during fermentation. J Antibiot 66:231–233

    Article  CAS  PubMed  Google Scholar 

  • Choi JN, Kim J, Ponnusamy K, Lim C, Kim JG, Muthaiya MJ, Lee C (2013b) Metabolic changes of Phomopsis longicolla fermentation and its effect on antimicrobial activity against Xanthomonas oryzae. J Microbiol Biotechnol 23(2):177–183

    Article  CAS  PubMed  Google Scholar 

  • Christian OE, Compton J, Christian KR, Mooberry SL, Valeriote FA, Crews P (2005) Using jasplakinolide to turn on pathways that enable the isolation of new chaetoglobosins from Phomopsis asparagi. J Nat Prod 68:1592–1597

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Cimmino A, Andolfi A, Zonno AC, Troise C, Santini A, Tuzi A, Vurro M, Ash G, Evidente A (2012) Phomentrioloxin: a phytotoxic pentasubstituted geranylcyclohexentriol produced by Phomopsis sp., a potential mycoherbicide for Carthamus lanatus biocontrol. J Nat Prod 75:1130–1137

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  Google Scholar 

  • Convert O, Jellal A, Correia I, Dardoize F, Mernguy L, Cherton JC (1994) A novel mycotoxin: the chaetoglobosin N from infested maize by Phomopsis leptostromiformis. II: Structure elucidation by 1H and 13C NMR. Analysis 22:217–221

    CAS  Google Scholar 

  • Dai D, Carté BK, Sidebottom PJ, Yew ALS, Siew-Bee N, Huang Y, Butler MS (2001) Circumdatin G, a new alkaloid from the fungus Aspergillus ochraceus. J Nat Prod 64:125–126

    Article  CAS  PubMed  Google Scholar 

  • Dai J, Krohn K, Flörke U, Gehle D, Aust H, Draeger S, Schulz B, Rheinheimer J (2005a) Novel highly substituted biraryl ethers, phomosines D–G, isolated from the endophytic fungus Phomopsis sp. from Adenocarpus foliolosus. Eur J Org Chem 23:5100–5105

    Article  CAS  Google Scholar 

  • Dai J, Krohn K, Gehle D, Kock I, Flörke U, Aust H, Draeger S, Schulz B, Rheinheimer J (2005b) New oblongolides isolated from the endophytic fungus Phomopsis sp. from Melilotus dentata from the shores of the Baltic Sea. Eur J Org Chem 18:4009–4016

    Article  CAS  Google Scholar 

  • Dayarathne MC, Boonmee S, Braun U, Crous PW, Daranagama DA, Dissanayake AJ, Ekanayaka H, Jayawardena R, Jones EBG, Maharachchikumbura SSN, Perera RH, Phillips AJL, Stadler M, Thambugala KM, Wanasinghe DN, Zhao Q, Hyde KD, Jeewon R (2016) Taxonomic utility of old names in current fungal classification and nomenclature: Conflicts, confusion & clarifications. Mycosphere 7(11):1622–1648

    Google Scholar 

  • Dettrakul S, Kittakoop P, Isaka M, Nopichai S, Suyarnsestakorn C, Tanticharoen, Thebtaranontha MY (2003) Antimycobacterial pimarane diterpenes from the fungus Diaporthe sp. Bioorg Med Chem Lett 13:1253–1255

    Article  CAS  PubMed  Google Scholar 

  • Ding B, Yuan J, Huang X, Wen W, Zhu X, Liu Y, Li H, Lu Y, He L, Tan H, She Z (2013) New dimeric members of the phomoxanthone family: phomolactonexanthones A, B and deacetylphomoxanthone C isolated from the fungus Phomopsis sp. Mar Drugs 11:4961–4972

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Dissanayake AJ, Liu M, Zhang W, Chen Z, Udayanga D, Chukeatirote E, Li X, Yan J, Hyde KD (2015) Morphological and molecular characterisation of Diaporthe species associated with grapevine trunk disease in China. Fungal Biol 119:283–294

    Article  CAS  PubMed  Google Scholar 

  • Du X, Lu C, Li Y, Zheng Z, Su W, Shen Y (2008) Three new antimicrobial metabolites of Phomopsis sp. J Antibiot 61(4):250–253

    Article  CAS  PubMed  Google Scholar 

  • Erincik O, Madden LV (2001) Effect of growth stage on susceptibility of grape berry and rachis tissues to infection by Phomopsis viticola. Plant Dis 85:517–520

    Article  Google Scholar 

  • Evidente A, Rodeva R, Andolfi A, Stoyanova Z, Perrone C, Motta A (2011) Phytotoxic polyketides produced by Phomopsis foeniculi, a strain isolated from diseased Bulgarian fennel. Eur J Plant Pathol 130:173–182

    Article  CAS  Google Scholar 

  • Frisvad JC (2015) Fungal chemotaxonomy. In: Zeilinger S, Martín J-F, García-Estrada C (eds) Biosynthesis and molecular genetics of fungal secondary metabolites, vol 2, Springer, New York, pp 103–121

  • Gao JM, Yang SX, Qin JC (2013) Azaphilones: chemistry and biology. Chem Rev 113:4755–4811

    Article  CAS  PubMed  Google Scholar 

  • Garcia-Reyne A, López-Medrano F, Morales JM, Esteban CG, Martín I, Eraña I, Meije Y, Lalueza A, Alastruey-Izquierdo A, Rodríguez-Tudela JL, Aguado JM (2011) Cutaneous infection by Phomopsis longicolla in a renal transplant recipient from Guinea: first report of human infection by this fungus. Transpl Infect Dis 13:204–207

    Article  CAS  PubMed  Google Scholar 

  • Goddard M, Mottier N, Jeanneret-Gris J, Christen D, Tabacchi R, Abou-Mansour E (2014) Differential production of phytotoxins from Phomopsis sp. from grapevine plants showing esca symptoms. J Agric Food Chem 62:8602–8607

    Article  CAS  PubMed  Google Scholar 

  • Gomes RR, Glienke C, Videira SIR, Lombard L, Groenewald J, Crous PW (2013) Diaporthe: a genus of endophytic, saprobic and plant pathogenic fungi. Persoonia 31:1–41

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Hemtasin C, Kanokmedhakul S, Kanokmedhakul K, Hahnvajanawong C, Soytong K, Prabpai S, Kongsaeree P (2011) cytotoxic pentacyclic and tetracyclic aromatic sesquiterpenes from Phomopsis archeri. J Nat Prod 74:609–613

    Article  CAS  PubMed  Google Scholar 

  • Hirose T, Izawa Y, Koyoma K, Natori S, Iid K, Yahara I, Shimaoka S, Maruyama K (1990) The Effects of New Cytochalasins from Phomopsis sp. and the derivatives on cellular structure and actin polymerization. Chem Pharm Bull 38:971–974

    Article  CAS  PubMed  Google Scholar 

  • Horn WS, Simmonds MSJ, Schwartz RE, Blaney WM (1995) Phomopsichalasin, a novel antimicrobial agent from an endophytic Phomopsis sp. Tetrahedron 51:3969–3978

    Article  CAS  Google Scholar 

  • Hsiao C, Hsiao S, Chen W, Guh J, Hsiao G, Chan Y, Lee T, Chung C (2012) Pycnidione, a fungus-derived agent, induces cell cycle arrest and apoptosis in A549 human lung cancer cells. Chem Biol Interact 197:23–30

    Article  CAS  PubMed  Google Scholar 

  • Huang Z, Cai X, Shao C, She Z, Xia X, Chen Y, Yang J, Zhou S, Lin Y (2008) Chemistry and weak antimicrobial activities of phomopsins produced by mangrove endophytic fungus Phomopsis sp. ZSU-H76. Phytochemistry 69(7):1604–1608

    Article  CAS  PubMed  Google Scholar 

  • Huang Z, Guo Z, Yang R, Yin X, Li X, Luo W, She Z, Lin Y (2009) Chemistry and cytotoxic activities of polyketides produced by the mangrove endophytic fungus Phomopsis SP. ZSU-H76. Chem Nat Compd 45:625–628

    Article  CAS  Google Scholar 

  • Huang H, Yang R, Yin X, She Z, Lin Y (2010a) Structure elucidation and NMR assignments for two xanthones derivatives from a mangrove endophytic fungus Phomopsis sp. (No. ZH19. Magn Reson Chem 48:80–82

    CAS  PubMed  Google Scholar 

  • Huang Z, Yang GZ, She Z, Lin Y (2010b) A new naphtho-γ-pyrone from mangrove endophytic fungus ZSU-H26. Chem Nat Compd 46:15–18

    Article  CAS  Google Scholar 

  • Hussain H, Akhtar N, Draeger S, Schulz B, Pescitelli G, Salvadori P, Antus S, Kurtán T (2009) New bioactive 2,3-epoxycyclohexenes and isocoumarins from the endophytic fungus Phomopsis sp. from Laurus azorica. Eur J Org Chem 5:749–756

    Article  CAS  Google Scholar 

  • Hussain H, Ahmed I, Schulz B, Draeger S, Krohn K (2010) Pyrenocines J–M: Four new pyrenocines from the endophytic fungus, Phomopsis sp. Fitoterapia 83:523–526

    Article  CAS  Google Scholar 

  • Hussain H, Tchimene MK, Ahmed I, Meier K, Steinert M, Draeger S, Schulz B, Krohn K (2011) Antimicrobial chemical constituents from the endophytic fungus Phomopsis sp. from Notobasis syriaca. Nat Prod Commun 6:1905–1906

    CAS  PubMed  Google Scholar 

  • Hussain H, Krohn K, Ahmed I, Draeger S, Schulz B, Pietro SD, Pescitelli G (2012) Phomopsinones A–D: four new pyrenocines from endophytic fungus Phomopsis sp. Eur J Org Chem 9:1783–1789

    Article  CAS  Google Scholar 

  • Isaka M, Jaturapat A, Rukseree K, Danwisetkanjana K, Tanticharoen M, Thebtaranonth Y (2001) Phomoxanthones A and B, novel xanthone dimers from the endophytic fungus Phomopsis species. J Nat Prod 64:1015–1018

    Article  CAS  PubMed  Google Scholar 

  • Ito A, Maeda H, Tonouchi A, Hashimoto M (2015) Relative and absolute structure of phomolide C. Biosci Biotechn Biochem 79:1067–1069

    Article  CAS  Google Scholar 

  • Izawa Y, Hirose T, Shimizu , Koyama K, Natori S (1989) Six new 10-pheynl-[11]cytochalasans, cytochalasins N - S from Phomopsis sp. Tetrahedron 452323–2335

  • Jansen N, Ohlendorf B, Erhard A, Bruhn T, Bringmann G, Imhoff JF (2013) Helicusin E, isochromophilone X and isochromophilone XI: new chloroazaphilones produced by the fungus Bartalinia robillardoides Strain LF550. Mar Drugs 11:800–816

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Khamthong N, Rukachaisirikul V, Phongpaichit S, Preedanon S, Sakayaroj J (2014) An antibacterial cytochalasin derivative from the marine-derived fungus Diaporthaceae sp. PSU-SP2/4. Phytochem Lett 10:5–9

    Article  CAS  Google Scholar 

  • Klaiklay S, Rukachaisirikul V, Phongpaichit S, Pakawatchai C, Saithong S, Buatong J, Preedanon S, Sakayaroj J (2012) Anthraquinone derivatives from the mangrove-derived fungus Phomopsis sp. PSU-MA214. Phytochem Lett 5:738–742

    Article  CAS  Google Scholar 

  • Kobayashia H, Megurob S, Yoshimotob T, Namikoshib M (2003) Absolute structure, biosynthesis, and anti-microtubule activity of phomopsidin, isolated from a marine-derived fungus Phomopsis sp. Tetrahedron 59:455–459

    Article  Google Scholar 

  • Krohn K, Michel A, Roemer E, Flörke U, Aust HJ, Draeger S, Schulz B, Wray V (1995) Biologically active metabolites from fungi 61; Phomosines A-C three new biaryl ethers from Phomopsis sp. Nat Prod Lett 6:309–314

    Article  CAS  Google Scholar 

  • Krohn K, Farooq U, Hussain H, Ahmed I, Rheinheimer J, Draeger S, Schulz B, van Ree T (2011) Phomosines H-J, novel highly substituted biaryl ethers, isolated from the endophytic fungus Phomopsis sp. from Ligustrum vulgare. Nat Pro Commun 6(12):1907–1912

    CAS  Google Scholar 

  • Kuhnert E, Sir EB, Lambert C, Hyde KD, Hladki AI, Romero AI, Rohde M, Stadler M (2016) Phylogenetic and chemotaxonomic resolution of the genus Annulohypoxylon (Xylariaceae) including four new species. Fungal Divers, in press (DOI: 10.1007/s13225-016-0377-6)

  • Li Y, Wang M, Huang J, Shen M (2010) TMYC secondary metabolites from Phomopsis sp. A123. Mycology 1:254–261

    Article  CAS  Google Scholar 

  • Li C, Wang J, Luo C, Ding W, Cox DG (2014) A new cyclopeptide with antifungal activity from the co-culture broth of two marine mangrove fungi. Nat Prod Res 28:616–621

    Article  CAS  PubMed  Google Scholar 

  • Lim C, Kim J, Choi JN, Ponnusamy K, Jeon Y, Kim SU, Kim JG, Lee C (2010) Identification, fermentation, and bioactivity against Xanthomonas oryzae of antimicrobial metabolites isolated from Phomopsis longicolla S1B4. J Microbiol Biotechnol 20:494–500

    CAS  PubMed  Google Scholar 

  • Lin X, Huang Y, Fang M, Wang J, Zheng Z, Su W (2005) Cytotoxic and antimicrobial metabolites from marine lignicolous fungi, Diaporthe sp. FEMS Microbiol Lett 251(1):53–58

    Article  CAS  PubMed  Google Scholar 

  • Lin X, Lu C, Shen Y (2008) One new ten-membered lactone from Phomopsis sp. B27, an endophytic fungus of Annona squamosa. Chin J Nat Med 6:391–394

    Article  CAS  Google Scholar 

  • Lin T, Lin X, Lu C, Hu Z, Huang W, Huang Y, Shen Y (2009) Secondary metabolites of Phomopsis sp. XZ-26, an endophytic fungus from Camptotheca acuminate. Eur J Org Chem 18:2975–2982

    Article  CAS  Google Scholar 

  • Liu Y, Hu Z, Lin X, Lu C, Shen Y (2013) A new polyketide from Diaporthe sp. SXZ-19, an endophytic fungal strain of Camptotheca acuminata. Nat Prod Res 27:2100–2104

    Article  CAS  PubMed  Google Scholar 

  • Masango MG, Ellis CE, Botha CJ (2014) Cytotoxicity of diplodiatoxin, dipmatol and diplonine, metabolites synthesized by Stenocarpella maydis. Toxicon 82:26–29

    Article  CAS  PubMed  Google Scholar 

  • Masango MG, Ellis CE, Botha CJ (2015) Characterization of cell death caused by diplodiatoxin and dipmatol, toxic metabolites of Stenocarpella maydis. Toxicon 102:14–24

    Article  CAS  PubMed  Google Scholar 

  • Meza A, Santos EA, Gomes RS, de Lima DP, Beatriz A (2015) Cytosporones and related compounds, a review: isolation, biosynthesis, synthesis and biological activity of promising fungal resorcinolic lipids. Curr Org Synth 12(5):618–638

    Article  CAS  Google Scholar 

  • Mostert L, Crous PW, Kang JC, Phillips AJL (2001) Species of Phomopsis and a Libertella sp. occurring on grapevines with specific reference to South Africa: morphological, cultural, molecular and pathological characterization. Mycologia 93:146–167

    Article  Google Scholar 

  • Murali TS, Suryanarayanan TS, Geeta R (2006) Endophytic Phomopsis species: host range and implications for diversity estimates. Can J Microbiol 52:673–680

    Article  CAS  PubMed  Google Scholar 

  • Nair MSR, Carey ST (1975) Metabolites of pyrenomycetes II: nectriapyrone, an antibiotic monoterpenoid. Tetrahedron Lett 16:1655–1658

    Google Scholar 

  • Namikoshi M, Kobayashi H, Yoshimoto T, Hosoya T (1997) Phomopsidin, a new inhibitor of microtubule assembly produced by Phomopsis sp. isolated from coral reef in Pohnpei. J Antibiot 50:890–892

    Article  CAS  PubMed  Google Scholar 

  • Ola ARB, Debbab A, Kurtán T, Brötz-Oesterhelt H, Amal H (2014) Dihydroanthracenone metabolites from the endophytic fungus Diaporthe melonis isolated from Annona squamosa L. Tetrahedron Lett 55:3147–3150

    Article  CAS  Google Scholar 

  • Pornpakakul S, Roengsumran S, Deechangvipart S, Petsom A, Muangsin N, Ngamrojnavanich N, Sriubolmas N, Chaichit N, Ohta T (2007) Diaporthichalasin, a novel CYP3A4 inhibitor from an endophytic Diaporthe sp. Tetrahedron Lett 48:651–655

    Article  CAS  Google Scholar 

  • Prachya S, Wiyakrutta S, Sriubolmas N, Ngamrojanavanich N, Mahidol S, Ruchirawat C, Kittakoop P (2007) Cytotoxic mycoepoxydiene derivatives from an endophytic fungus Phomopsis sp. isolated from Hydnocarpus anthelminthicus. Planta Med 73(13):1418–1420

    Article  CAS  PubMed  Google Scholar 

  • Raja HA, Miller AN, Pearce CJ, Oberlies NH (2017) Fungal identification using molecular tools: a primer for the natural products research community. J Nat Prod doi:10.1021/acs.jnatprod.6b01085

  • Rönsberg D, Debbab A, Mandi A, Vasylyeva V, Böhler P, Stork B, Engelke L, Hamacher A, Sawadogo R, Diederich M, Wray V, Lin W, Kassack MU, Janiak C, Scheu S, Wesselborg S, Kurtan T, Aly AH, Proksch P (2013) Pro-apoptotic and immunostimulatory tetrahydroxanthone dimers from the endophytic fungus Phomopsis longicolla. J Org Chem 78(24):12409–12425

    Article  PubMed  CAS  Google Scholar 

  • Rossman AY, Adams GC, Cannon PF, Castlebury LA, Crous PW, Gryzenhout M, Jaklitsch WM, Mejia LC, Stoykov D, Udayanga D, Voglmayr H (2015) Recommendations of generic names in Diaporthales competing for protection or use. IMA Fungus 6:145–154

    Article  PubMed  PubMed Central  Google Scholar 

  • Rukachaisirikul V, Sommart U, Phongpaichit L, Sakayaroj J, Kirtikara K (2008) Metabolites from the endophytic fungus Phomopsis sp. PSU-D15. Phytochemistry 69(3):783–787

    Article  CAS  PubMed  Google Scholar 

  • Santos JM, Vrandečić K, Ćosić J, Duvnjak T, Phillips AJL (2011) Resolving the Diaporthe species occurring on soybean in Croatia. Persoonia 27:9–19

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Sommart U, Rukachaisirikul V, Sukpondma Y, Phongpaichit S, Towatana NH, Graidist P, Hajiwangoh Z, Sakayaroj J (2009) A cyclohexenone derivative from diaporthaceous fungus PSU-H2. Arch Pharmacol Res 32(9):1227–1231

    Article  CAS  Google Scholar 

  • Stadler M (2011) Importance of secondary metabolites in the Xylariaceae as parameters for assessment of their taxonomy, phylogeny, and functional biodiversity. Curr Res Envion Appl Mycol 1:75–133

    Article  Google Scholar 

  • Stadler M, Læssøe T, Fournier J, Decock C, Schmieschek B, Tichy HV, Peršoh D (2014) A polyphasic taxonomy of Daldinia (Xylariaceae). Stud Mycol 77:1–143

    Article  PubMed  PubMed Central  Google Scholar 

  • Sutton DA, Timm WD, Morgan-Jones G, Rinaldi MG (1999) Human phaeohyphomycotic osteomyelitis caused by the coelomycete Phomopsis Saccardo 1905: criteria for identification, case history, and therapy. J Clin Microbiol 37:807–811

    CAS  PubMed  PubMed Central  Google Scholar 

  • Talontsi FM, Islam T, Facey P, Douanla-Meli C, 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 5:657–664

    Article  CAS  Google Scholar 

  • Tao Y, Mou M, Zeng X, Xu F, Cai JJ, She Z, Zhou S, Lin Y (2008) 1H and 13C NMR assignments of two new diaryl ethers phomopsides A and B from the mangrove endophytic fungus (ZZF08). Magn Reson Chem 46:761–764

    Article  CAS  PubMed  Google Scholar 

  • Thines E, Anke H (1998) Scytalols A, B, C, and D and other modulators of melanin biosynthesis from Scytalidium sp. 36-93. J Antibiot 51:387–393

    Article  CAS  PubMed  Google Scholar 

  • Thompson SM, Tan YP, Young AJ, Neate SM, Aitken EA, Shivas RG (2011) Stem cankers on sunflower (Helianthus annuus) in Australia reveal a complex of pathogenic Diaporthe (Phomopsis) species. Persoonia 27:80–89

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Tomoda H, Namatame I, Si S, Kawaguchi K, Masuma R, Namikoshi M, Omura S (1999) Phenochalasins, inhibitors of lipid droplet formation in mouse macrophages, produced by Phomopsis sp. FT-0211. J Antibiot 52:857–861

    Article  CAS  PubMed  Google Scholar 

  • Tsantrizos YS, Ogilvie KK (1992) Phytotoxic metabolites of Phomopsis convolvulus, a host-specific pathogen of field bindweed. Can J Chem 70:2276–2284

    Article  CAS  Google Scholar 

  • Udayanga D, Liu X, McKenzie EHC, Chukeatirote E, Bahkali AHA, Hyde KD (2011) The genus Phomopsis: biology, applications, species concepts and names of common pathogens. Fungal Divers 50:189–225

    Article  Google Scholar 

  • Udayanga D, Castlebury LA, Rossman AY, Chukeatirote E, Hyde KD (2014) Insights into the genus Diaporthe: phylogenetic species delimitation in the D. eres species complex. Fungal Divers 67:203–229

    Article  Google Scholar 

  • van Rensburg JCJ, Lamprecht SC, Groenewald JZ, Castlebury LA, Crous PW (2006) Characterization of Phomopsis spp. associated with die-back of rooibos (Aspalathus linearis) in South Africa. Stud Mycol 55:65–74

    Article  PubMed  PubMed Central  Google Scholar 

  • Van Warmelo KT, Marasas WFO (1972) Phomopsis leptostromiformis: the causal fungus of lupinosis, a mycotoxicosis, in sheep. Mycologia 64:316–324

    Article  PubMed  Google Scholar 

  • Venekar SA, Mishra BD, Sreekumar ES, Deshmukh SK, Fiebig H, Kelter G, Maier A (2014) Anticancer activity of new depsipeptide compound isolated from an endophytic fungus. J Antibiot 67:697–701

    Article  CAS  Google Scholar 

  • Wagenaar 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

    Article  CAS  PubMed  Google Scholar 

  • Wang W, Zhao B, Zhang W, Wua X, Wang R, Huang Y, Chen D, Park K, Weimer BC, Shen Y (2010) Mycoepoxydiene, a fungal polyketide, induces cell cycle arrest at the g2/m phase and apoptosis in HeLa cells. Bioorg Med Chem Lett 20(23):7054–7058

    Article  CAS  PubMed  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 cristangalli. J Antibiot 57:559–563

    Article  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

    Article  CAS  PubMed  Google Scholar 

  • Wheeler MM, Wheeler DMS, Peterson GW (1995) Anthraquinone pigments from the phytopathogen Phomopsis juniperovora Hahn. Phytochemistry 14:288–289

    Article  Google Scholar 

  • 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 48:938–941

    Article  CAS  Google Scholar 

  • Wu HC, Ge HM, Zang LY, Bei YC, Niu ZY, Wei WA, Feng XJ, Ding S, Weng S, Shen PP, Tan RX (2014) Diaporine, a novel endophyte-derived regulator of macrophage differentiation. Org Biomol Chem 12:6545–6548

    Article  CAS  PubMed  Google Scholar 

  • Yang J, Xu F, Huang C, Li J, She Z, Pei Z, Lin Y (2010) Metabolites from the mangrove endophytic fungus Phomopsis sp. (#zsu-H76). Eur J Org Chem 19:3692–3695

    Article  CAS  Google Scholar 

  • Yang JX, Chen Y, Huang C, She Z, Lin Y (2011) A new isocroman derivative from the marine fungus Phomopsis sp. ZH-111. Chem Nat Compd 47:13–16

    Article  CAS  Google Scholar 

  • Yang H, Gao Y, Niu D, Yang L, Gao X, Du G, Hu Q (2013a) Xanthone derivatives from the fermentation products of an endophytic fungus Phomopsis sp. Fitoterapia 91:189–193

    Article  CAS  PubMed  Google Scholar 

  • Yang JX, Qiu SX, She Z, Lin Y (2013b) A new xanthone derivative from the marine fungus Phomopsis sp. No. SK7RN3G1. Chem Nat Compd 49:246–248

    Article  CAS  Google Scholar 

  • Yang Z, Ding J, Ding K, Chen D, Cen S, Ge M (2013c) Phomonaphthalenone A: A novel dihydronaphthalenone with anti-HIV activity from Phomopsis sp. HCCB04730. Phytochem Lett 6:257–260

    Article  CAS  Google Scholar 

  • Yang JX, Qiu SX, She Z, Lin Y (2014) A new isochroman derivative from the marine fungus Phomopsis sp. (No. Gx-4). Chem Nat Compd 50:424–426

    Article  CAS  Google Scholar 

  • Yin L, Hlsayoshi K, Yoshiyuki T, Yuichi H, Shigeo I (1992) Binding selectivity of rhizoxin, phomopsin A, vinblastine, and ansamitocin P-3 to fungal tubulins: Differential interactions of these antimitotic agents with brain and fungal tubulins. Biochem Biophys Res Commun 187:722–729

    Article  Google Scholar 

  • Yuan L, Lin X, Zhao P, Ma J, Huang Y, Shen Y (2009) new polyketides from endophytic Diaporthe sp. XZ-07. Helv Chim Acta 92:1184–1190

    Article  CAS  Google Scholar 

  • Yuan L, Huang W, Du G, Gao X, Yang H, Hu Q, Ma Y (2015) Isolation of xanthones from fermentation products o endophytic fungus Phomopsis amygdali. Chem Nat Compd 51:460–463

    Article  CAS  Google Scholar 

  • Zang L, Wie W, Wang T, Guo Y, Tan R, Ge H (2012a) Isochromophilones from an endophytic fungus Diaporthe sp. Nat Prod Bioprospect 2:117–120

    Article  CAS  PubMed Central  Google Scholar 

  • Zang Y, Wie W, Guo Y, Wang T, Jiao RU, Wenig S, Tan RX, Ge HM (2012b) Sesquiterpenoids from the mangrove-derived endophytic fungus Diaporthe sp. J Nat Prod 75:1744–1749

    Article  CAS  Google Scholar 

  • Zhan F, Li X, Wu L, Yang T, Han Y, Li G (2013) Cytochalasins from endophytic fungus from Phomopsis sp. cib-109. Chem Nat Compd 49:696–698

    Article  CAS  Google Scholar 

  • Zhang C, Ondeyka JG, Herath KB, Guan Z, Collado J, Platas G, Pelaez F, Leavitt PS, Gurnett A, Nare B, Liberator P, Singh SB (2005) Tenellones A and B from a Diaporthe sp.: two highly substituted benzophenone inhibitors of parasite cGMP-dependent protein kinase activity. J Nat Prod 68:611–613

    Article  CAS  PubMed  Google Scholar 

  • Zhang W, Xu L, Yang L, Huang Y, Li S, Shen Y (2014) Phomopsidone A, a novel depsidone metabolite from the mangrove endophytic fungus Phomopsis sp. A123. Fitoterapia 96:146–151

    Article  CAS  PubMed  Google Scholar 

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Acknowledgements

A personal PhD stipend by German Academic Exchange Service (DAAD) and the Kenya National Council for Science and Technology (NACOSTI) to C.C. is gratefully acknowledged. We are deeply indebted to Ms. Asha J. Dissanayake, Institute of Plant and Environment Protection, Beijing Academy of Agriculture and Forestry Sciences, for providing the images in Fig. 1.

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Authors and Affiliations

  1. Department Microbial Drugs, Helmholtz Centre for Infection Research GmbH (HZI), Inhoffenstraße 7, 38124, Braunschweig, Germany

    Clara Chepkirui & Marc Stadler

  2. Partner Site Hannover-Braunschweig, German Centre for Infection Reseach Association (DZIF), Inhoffenstraße 7, 38124, Braunschweig, Germany

    Clara Chepkirui & Marc Stadler

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  1. Clara Chepkirui
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  2. Marc Stadler
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Correspondence to Marc Stadler.

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Chepkirui, C., Stadler, M. The genus Diaporthe: a rich source of diverse and bioactive metabolites. Mycol Progress 16, 477–494 (2017). https://doi.org/10.1007/s11557-017-1288-y

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