Abstract
Weeds represent one of the most challenging biotic factors for the agricultural sector, responsible for causing significant losses in important agricultural crops. Traditional herbicides have managed to keep weeds at bay, but overuse has resulted in negative environmental and toxicological impacts, including the increase of herbicide-resistant species. Within this context, the use of biologically derived (bio-)herbicides represents a promising solution because they are able to provide the desired phytotoxic effects while causing less toxic environmental damage. In recent years, bioactive secondary metabolites, in particular those bio-synthesized by endophytic fungi, have been shown to be promising sources of novel compounds that can be exploited in agriculture, including their use in weed control. Endophytic fungi have the ability to produce volatile and nonvolatile compounds with broad phytotoxic activity. In addition, as a result of the beneficial relationships they establish with their host plants, they are part of the colonization mechanism and can provide protection for their hosts. As such, endophytic fungi can be exploited as bioherbicides and as research tools. In this review, we cover 100 nonvolatile secondary metabolites with phytotoxic activity and more than 20 volatile organic compounds in a mixture, produced by 28 isolates of endophytic fungi from 21 host plant families, collected in 8 countries. This information can form the basis for the application of endophytic fungal compounds in weed control.
Key points
• Endophytic fungi produce a wide variety of secondary metabolites with unique and complex structures.
• Fungal endophytes produce volatile and nonvolatile compounds with promising phytotoxic activity.
• Endophytic fungi are a promising source of useful bioherbicides.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Adnan M, Alshammari E, Ashraf SA, Patel K, Lad K, Patel M (2018) Physiological and molecular characterization of biosurfactant producing endophytic fungi Xylaria regalis from the cones of thuja plicata as a potent plant growth promoter with its potential application. BioMed Res Int 2018:1–11. https://doi.org/10.1155/2018/7362148
Agrios G (2005) Plant pathology. Florida, USA https://doi.org/10.1016/C2009-0-02037-6
Bani M, Rispail N, Evidente A, Rubiales D, Cimmino A (2014) Identification of the main toxins isolated from Fusarium oxysporum f. sp. pisi race 2 and their relation with isolates’ pathogenicity. J Agric Food Chem 62:2574–2580. https://doi.org/10.1021/jf405530g
Bashiri S, Abdollahzadeh J, Di Lecce R, Alioto D, Górecki M, Pescitelli G, Masi M, Evidente A (2020) Rabenchromenone and rabenzophenone, phytotoxic tetrasubstituted chromenone and hexasubstituted benzophenone constituents produced by the oak-decline-associated fungus Fimetariella rabenhorstii. J Nat Prod 83:447–452. https://doi.org/10.1021/acs.jnatprod.9b01017
Betina V (1992) Biological effects of the antibiotic brefeldin A (decumbin, cyanein, ascotoxin, synergisidin): a retrospective. Folia Microbiol 37:3–11. https://doi.org/10.1007/bf02814572
Biasetto CR, Somensi A, de Abdalla CPV, de Abreu ML, Gualtieri CJS, Pfenning HL, da Bolzani SV, Araujo RA (2019) Phytotoxic constituents from endophytic fungus Xylaria cubensis associated with Eugenia brasiliensis. Quim Nova Vol. XY No. 00 1-4. https://doi.org/10.21577/0100-4042.20170367
Briggs DE (1966) Gibberellin-like activity of helminthosporol and helminthosporic acid. Nature 210:418–419. https://doi.org/10.1038/210418b0
Briquet M, Vilret D, Goblet P, Mesa M, Eloy M-C (1998) Plant cell membranes as biochemical targets of the phytotoxin helminthosporol. J Bioenerg Biomembr 30:285–295. https://doi.org/10.1023/a:1020553005293
Busi R, Powles SB, Beckie HJ, Renton M (2019) Rotations and mixtures of soil-applied herbicides delay resistance. Pest Manag Sci. https://doi.org/10.1002/ps.5534
Cantrell CL, Dayan FE, Duke SO (2012) Natural products as sources for new pesticides. J Nat Prod 75:1231–1242. https://doi.org/10.1021/np300024u
Capasso R, Evidente A, Cutignano A, Vurro M, Chiara Zonno M, Bottalico A (1996) Fusaric and 9,10-dehydrofusaric acids and their methyl esters from Fusarium Nygamai. Phytochemistry 41:1035–1039
Cimmino A, Masi M, Evidente M, Superchi S, Evidente A (2015) Fungal phytotoxins with potential herbicidal activity: chemical and biological characterization. Nat Prod Rep 32:1629–1653. https://doi.org/10.1039/c5np00081e
Délye C, Jasieniuk M, Le Corre V (2013) Deciphering the evolution of herbicide resistance in weeds. Trends genet 29:649–658. https://doi.org/10.1016/j.tig.2013.06.001
Demain AL (2014) Valuable secondary metabolites from fungi. biosynthesis and molecular genetics of fungal secondary metabolites 1–15. https://doi.org/10.1007/978-1-4939-1191-2_1
Devine GJ, Furlong MJ (2007) Insecticide use: contexts and ecological consequences. Agric Human Values 24:281–306. https://doi.org/10.1007/s10460-007-9067-z
Erfandoust R, Habibipour R, Soltani J (2020) Antifungal activity of endophytic fungi from Cupressaceae against human pathogenic Aspergillus fumigatus and Aspergillus niger. J Mycol Med 30:100987. https://doi.org/10.1016/j.mycmed.2020.100987
Fernández-Aparicio M, Delavault P, Timko MP (2020) Management of infection by parasitic weeds: a review. Plants 9:1184. https://doi.org/10.3390/plants9091184
Flores-Reséndiz M, Lappe-Oliveras P, Macías-Rubalcava ML (2021) Mitochondrial damage produced by phytotoxic chromenone and chromanone derivatives from endophytic fungus Daldinia eschscholtzii strain GsE13. Appl Microbiol Biotechnol 105:4225–4239. https://doi.org/10.1007/s00253-021-11318-7
Food and agriculture organization of the united nations, FAO (2021) https://www.fao.org/home/en Retrieved November 1, 2021
Gao F, Dai CC, Liu X (2010) Mechanisms of fungal endophytes in plant protection against pathogens. Afr J Microbiol Res 4:1346–1351 http://www.academicjournals.org/ajmr
García-Méndez MC, Macías-Ruvalcaba NA, Lappe-Oliveras P, Hernández-Ortega S, Macías-Rubalcava ML (2016) Phytotoxic potential of secondary metabolites and semisynthetic compounds from endophytic fungus Xylaria feejeensis strain SM3e-1b isolated from Sapium macrocarpum. J Agric Food Chem 64:4255–4263. https://doi.org/10.1021/acs.jafc.6b01111
Gharde Y, Singh PK, Dubey RP, Gupta PK (2018) Assessment of yield and economic losses in agriculture due to weeds in India. Crop Prot 107:12–18. https://doi.org/10.1016/j.cropro.2018.01.007
González MC, Anaya AL, Glenn AE, Macías-Rubalcava ML, Hernández-Bautista BE, Hanlin RT (2009) Muscodor yucatanensis, a new endophytic ascomycete from Mexican chakah, Bursera simaruba. Mycotaxon 110:363–372. https://doi.org/10.5248/110.363
González MC, Anaya AL, Glenn AE, Saucedo-García A, Macías-Rubalcava ML, Hanlin RT (2007) A new endophytic ascomycete from El Eden Ecological Reserve, Quintana Roo, Mexico. Mycotaxon 101:251–260
Hao S-H, Wei Y, Wang J, Zhou Y-M (2015) Allelopathy and the active metabolites of the endophytic fungus, Alternaria J46, from Platycladus orientalis. Weed Biol Manag 15:95–101. https://doi.org/10.1111/wbm.12072
Harding DP, Raizada MN (2015) Controlling weeds with fungi, bacteria and viruses: a review. Front Plant Sci 6:659. https://doi.org/10.3389/fpls.2015.00659
Hashimoto T, Sakurai A, Tamura S (1967) Physiological activities of helminthosporol and helminthosporic acid. Plant Cell Physiol 8:23–34
Hawksworth DL (1991) The fungal dimension of biodiversity: magnitude, significance, and conservation. J mycol res 95:641–655. https://doi.org/10.1016/S0953-7562(09)80810-1
Hsieh H-M, Lin C-R, Fang M-J, Rogers JD, Fournier J, Lechat C, Ju Y-M (2010) Phylogenetic status of Xylaria subgenus Pseudoxylaria among taxa of the subfamily Xylarioideae (Xylariaceae) and phylogeny of the taxa involved in the subfamily. Mol Phylogenet Evol 54:957–969. https://doi.org/10.1016/j.ympev.2009.12.015
Hummadi EH, Dearden A, Generalovic T, Clunie B, Harrott A, Cetin Y, Demirbek M, Khoja S, Eastwood D, Dubley E, Hazir S, Touray M, Ulug D, Gulsen SH, Cimen H, Butt T (2021) Volatile organic compounds of Metarhizium brunneum influence the efficacy of entomopathogenic nematodes in insect control. Biol Control 155:104527. https://doi.org/10.1016/j.biocontrol.2020.104527
Ichihara A, Katayama K, Teshima H, Oikawa H, Sakamura S (1996) Chaetoglobosin O and other phytotoxic metabolites from Cylindrocladium floridanum, a causal fungus of alfalfa black rot disease. Biosci Biotechnol Biochem 60:60–361. https://doi.org/10.1271/bbb.60.360
Kaddes A, Fauconnier M-L, Sassi K, Nasraoui B, Jijakli M-H (2019) Endophytic fungal volatile compounds as solution for sustainable agriculture. Molecules 24:1065. https://doi.org/10.3390/molecules24061065
Khan AL, Hamayun M, Hussain J, Kang S-M, Lee I-J (2012) The newly isolated endophytic fungus Paraconiothyrium sp. LK1 produces ascotoxin. Molecules 17:1103–1112. https://doi.org/10.3390/molecules17011103
Kusari S, Hertweck C, Spiteller M (2012) Chemical ecology of endophytic fungi: origins of secondary metabolites. Chem Biol 19:792–798. https://doi.org/10.1016/j.chembiol.2012.06.004
Lamichhane JR, Devos Y, Beckie HJ, Owen MDK, Tillie P, Messéan A, Kudsk P (2016) Integrated weed management systems with herbicide-tolerant crops in the European Union: lessons learnt from home and abroad. Crit Rev Biotechnol 37:459–475. https://doi.org/10.1080/07388551.2016.1180588
Li H, Xiao J, Gao Y-Q, Tang J-J, Zhang A-L, Gao J-M (2014) Chaetoglobosins from Chaetomium globosum, an endophytic fungus in Ginkgo biloba, and their phytotoxic and cytotoxic activities. J Agric Food Chem 62:3734–3741. https://doi.org/10.1021/jf500390h
Li Y-Y, Tan X-M, Wang Y-D, Yang J, Zhang Y-G, Sun B-D, Gong T, Guo L-P, Ding G (2020) Bioactive seco-sativene sesquiterpenoids from an Artemisia desertorum endophytic fungus, Cochliobolus sativus. J Nat Prod 83:1488–1494. https://doi.org/10.1021/acs.jnatprod.9b01148
Liu J, Liu G (2018) Analysis of secondary metabolites from plant endophytic fungi. Plant pathogenic fungi and oomycetes 1848:25–38. https://doi.org/10.1007/978-1-4939-8724-5_3
Liu S, Dai H, Orfali RS, Lin W, Liu Z, Proksch P (2016) New fusaric acid derivatives from the endophytic fungus Fusarium oxysporum and their phytotoxicity to barley leaves. J Agric Food Chem 64:3127–3132. https://doi.org/10.1021/acs.jafc.6b00219
Liu X, Zhou Z-Y, Cui J-L, Wang M-L, Wang J-H (2021) Biotransformation ability of endophytic fungi: from species evolution to industrial applications. Appl Microbiol Biotechnol 105:7095–7113. https://doi.org/10.1007/s00253-021-11554-x
Ma K-L, Wei W-J, Li H-Y, Song Q-Y, Dong S-H, Gao K (2019) Meroterpenoids with diverse ring systems and dioxolanone-type secondary metabolites from Phyllosticta capitalensis and their phytotoxic activity. Tetrahedron 75:4611–4619. https://doi.org/10.1016/j.tet.2019.07.003
Macías-Rubalcava ML, García-Méndez MC, King-Díaz B, Macías-Ruvalcaba NA (2017) Effect of phytotoxic secondary metabolites and semisynthetic compounds from endophytic fungus Xylaria feejeensis strain SM3e-1b on spinach chloroplast photosynthesis. J Photochem Photobiol B Biol 166:35–43. https://doi.org/10.1016/j.jphotobiol.2016.11.002
Macías-Rubalcava ML, Hernández-Bautista BE, Jiménez-Estrada M, González MC, Glenn AE, Hanlin RT, Hernández-Ortega S, Saucedo-García A, Muria-González JM, Anaya AL (2008) Naphthoquinone spiroketal with allelochemical activity from the newly discovered endophytic fungus Edenia gomezpompae. Phytochemistry 69:1185–1196. https://doi.org/10.1016/j.phytochem.2007.12.006
Macías-Rubalcava ML, Hernández-Bautista BE, Oropeza F, Duarte G, González MC, Glenn AE, Hanlin RT, Anaya AL (2010) Allelochemical effects of volatile compounds and organic extracts from Muscodor yucatanensis, a tropical endophytic fungus from Bursera simaruba. J Chem Ecol 36:1122–1131. https://doi.org/10.1007/s10886-010-9848-5
Macías-Rubalcava ML, Ruiz-Velasco Sobrino ME, Meléndez-González C, King-Díaz B, Lotina-Hennsen B (2014a) Selected phytotoxins and organic extracts from endophytic fungus Edenia gomezpompae as light reaction of photosynthesis inhibitors. J Photochem Photobiol B Biol 138:17–26. https://doi.org/10.1016/j.jphotobiol.2014.05.003
Macías-Rubalcava ML, Ruiz-Velasco Sobrino ME, Meléndez-González C, Hernández-Ortega S (2014b) Naphthoquinone spiroketals and organic extracts from the endophytic fungus Edenia gomezpompae as potential herbicides. J Agric Food Chem 62(16):3553–3562. https://doi.org/10.1021/jf500965k
Macías-Rubalcava ML, Sánchez-Fernández RE (2017) Secondary metabolites of endophytic Xylaria species with potential applications in medicine and agriculture. World. J Microbiol Biotechnol 33:15. https://doi.org/10.1007/s11274-016-2174-5
Macías-Rubalcava ML, Sánchez-Fernández RE, Roque-Flores G, Lappe-Oliveras P, Medina-Romero YM (2018) Volatile organic compounds from Hypoxylon anthochroum endophytic strains as postharvest mycofumigation alternative for cherry tomatoes. Food Microbiol 76:363–373. https://doi.org/10.1016/j.fm.2018.06.014
Manganyi MC, Ateba CN (2020) Untapped potentials of endophytic fungi: a review of novel bioactive compounds with biological applications. Microorganisms 8:1934. https://doi.org/10.3390/microorganisms8121934
Masteling R, Lombard L, de Boer W, Raaijmakers JM, Dini-Andreote F (2019) Harnessing the microbiome to control plant parasitic weeds. Curr Opin Microbiol 49:26–33. https://doi.org/10.1016/j.mib.2019.09.006
Mishra S, Sahu PK, Agarwal V, Singh N (2021) Exploiting endophytic microbes as micro-factories for plant secondary metabolite production. Appl Microbiol Biotechnol 105:6579–6596. https://doi.org/10.1007/s00253-021-11527-0
Newman DJ, Cragg M (2020) Natural products as sources of new drugs over the nearly four decades from 01/1981 to 09/2019. J Nat Prod 83:770–803. https://doi.org/10.1021/acs.jnatprod.9b01285
Oerke E-C (2006) Crop losses to pests. J Agric Sci 144:31. https://doi.org/10.1017/s0021859605005708
Pakdaman B, Goltapeh E (2018) Weeds, herbicides and plant disease management. sustainable agriculture Reviews 31:41–178. https://doi.org/10.1007/978-3-319-94232-2_3
Patil RH, Patil MP, Maheshwari VL (2016) Bioactive secondary metabolites from endophytic fungi. A review of biotechnological production and their potential applications. Stud Nat Prod Chem 49:189–205. https://doi.org/10.1016/b978-0-444-63601-0.00005-3
Pena LC, Jungklaus GH, Savi DC, Ferreira-Maba L, Servienski A, Maia BHLNS, Annies V, Galli-Terasawa LV, Glienke C, Kava V (2019) Muscodor brasiliensis sp. nov. produces volatile organic compounds with activity against Penicillium digitatum. Microbiol Res 221:28-35. https://doi.org/10.1016/j.micres.2019.01.002
Petrini O (1991) Fungal endo phytes of tree leaves. Microbial Ecology of Leaves 179–197. https://doi.org/10.1007/978-1-4612-3168-4_9
Piyasena KGNP, Wickramarachchi WART, Kumar NS, Jayasinghe L, Fujimoto Y (2015) Two phytotoxic azaphilone derivatives from Chaetomium globosum, a fungal endophyte isolated from Amaranthus viridis leaves. Mycol 6(3-4):158–160. https://doi.org/10.1080/21501203.2015.1089332
Popp J, Pető K, Nagy J (2012) Pesticide productivity and food security. Agron Sustain Dev 33:243–255. https://doi.org/10.1007/s13593-012-0105-x
Qader MM, Kumar NS, Jayasinghe L, Araya H, Fujimoto Y (2017) Bioactive sesquiterpenes from an endophytic fungus Bipolaris sorokiniana isolated from a popular medicinal plant Costus speciosus. Mycol 8:17–20. https://doi.org/10.1080/21501203.2016.1269844
Radhakrishnan R, Alqarawi AA, Abd Allah EF (2018) Bioherbicides: current knowledge on weed control mechanism. Ecotoxicol Environ Saf 158:131–138. https://doi.org/10.1016/j.ecoenv.2018.04.018
Reichert Júnior FW, Scariot MA, Forte CT, Pandolfi L, Dil JM, Weirich S, Carezia C, Mulinari J, Mazutti MA, Fongaro G, Galon L, Treichel H, Mossi AJ (2019) New perspectives for weeds control using autochthonous fungi with selective bioherbicide potential. Heliyon 5:e01676. https://doi.org/10.1016/j.heliyon.2019.e01676
Ren-Yi G, Lei X, Yi K, III Ming C, Jian-Chun Q, Li L, Sheng-Xiang Y, Li-Chun Z (2015) Chaetominine, (+)-alantrypinone, questin, isorhodoptilometrin, and 4-hydroxybenzaldehyde produced by the endophytic fungus Aspergillussp. YL-6 inhibit wheat (Triticum aestivum) and radish (Raphanus sativus) germination. J Plant Interact 10:87–92. https://doi.org/10.1080/17429145.2015.1019742
Reveglia P, Cinelli T, Cimmino A, Masi M, Evidente A (2018) The main phytotoxic metabolite produced by a strain of Fusarium oxysporum inducing grapevine plant declining in Italy. Nat Prod Res 32(20):2398–2407. https://doi.org/10.1080/14786419.2017.1415897
Ritzenthaler C, Nebenführ A, Movafeghi A, Stussi-Garaud C, Behnia L, Pimpl P, Staehelin LA, Robinson DG (2002) Reevaluation of the effects of brefeldin a on plant cells using tobacco bright yellow 2 cells expressing golgi-targeted green fluorescent protein and copi antisera. Plant Cell 14:237–261. https://doi.org/10.1105/tpc.010237
Rodriguez RJ, White JF Jr, Arnold AE, Redman RS (2009) Fungal endophytes: diversity and functional roles. New Phytol 182:314–330. https://doi.org/10.1111/j.1469-8137.2009.02773.x
Sánchez-Fernández RE, Sánchez-Fuentes R, Rangel-Sánchez H, Hernández-Ortega S, López-Cortés JG, Macías-Rubalcava ML (2020) Antifungal and antioomycete activities and modes of action of isobenzofuranones isolated from the endophytic fungus Hypoxylon anthochroum strain Gseg1. Pestic Biochem Physiol 169:104670. https://doi.org/10.1016/j.pestbp.2020.104670
Sánchez-Ortiz BL, Sánchez-Fernández RE, Duarte G, Lappe-Oliveras P, Macías-Rubalcava ML (2016) Antifungal, anti-oomycete and phytotoxic effects of volatile organic compounds from the endophytic fungus Xylaria sp. strain PB3f3 isolated from Haematoxylon brasiletto. J Appl Microbiol 120:1313–1325. https://doi.org/10.1111/jam.13101
Sanodiya BS, Thakur GS, Baghel RK, Pandey AK, Prasad G, Bisen P (2010) Isolation and characterization of tenuazonic acid produced by Alternaria alternata, a potential bioherbicidal agent for control of Lantana Camara. J Plant Prot Res 50(2). https://doi.org/10.2478/v10045-010-0023-3
Sato S, Sofian FF, Suehiro W, Harneti D, Maharani R, Supratman U, Abdullah FF, Salam S, Koseki T, Shiono Y (2021) β- resorcylic acid derivatives, with their phytotoxic activities, from the endophytic fungus Lasiodiplodia theobromae in the mangrove plant Xylocarpus granatum. Chem Biodivers 18:3. https://doi.org/10.1002/cbdv.202000928
Savary S, Willocquet L, Pethybridge SJ, Esker P, McRoberts N, Nelson A (2019) The global burden of pathogens and pests on major food crops. Nat Ecol Evol. https://doi.org/10.1038/s41559-018-0793-y
Schulz B, Boyle C (2005) The endophytic continuum. mycol res 109:661–686. https://doi.org/10.1017/s095375620500273x
Shiono Y, Murayama T, Takahashi K, Okada K, Katohda S, Ikeda M (2005) Three oxygenated cyclohexenone derivatives produced by an endophytic fungus. Biosci Biotechnol Biochem 69:287–292. https://doi.org/10.1271/bbb.69.287
Shiono Y, Sato S, Sofian FF, Koseki T, Abdullah FF, Salam S, Hanerti D, Maharani R, Supratman U (2021) Phytotoxic β-resorcylic acid derivatives from the endophytic fungus Lasiodiplodia theobromae in the mangrove plant. Phytochem Lett 44:1–6. https://doi.org/10.1016/j.phytol.2021.05.003
Strobel G, Daisy B (2003) Bioprospecting for microbial endophytes and their natural products. Microbiol Mol Biol Rev 67:491–502. https://doi.org/10.1128/mmbr.67.4.491-502.2003
Strobel G, Daisy B, Castillo U, Harper J (2004) Natural products from endophytic microorganisms. J Nat Prod 67:257–268. https://doi.org/10.1021/np030397v
Sun X, Guo L-D (2012) Endophytic fungal diversity: review of traditional and molecular techniques. Mycol 31:65–76. https://doi.org/10.1080/21501203.2012.656724
Supratman U, Hirai N, Sato S, Watanabe K, Malik A, Annas S, Harneti D, Maharani R, Koseki T, Shiono Y (2019) New naphthoquinone derivatives from Fusarium napiforme of a mangrove plant. Nat Prod Res 1-7. https://doi.org/10.1080/14786419.2019.1650358
Supratman U, Suzuki T, Nakamura T, Yokoyama Y, Harneti D, Maharani R, Salam S, Abdullah F, Koseki T, Shiono Y (2019b) New metabolites produced by endophyte Clonostachys rosea B5 − 2. Nat Prod Res 1-7. https://doi.org/10.1080/14786419.2019.1656629
Tamura S, Sakurai A, Kainuma K, Takai M (1965) Isolation of helminthosporol as a natural plant growth-regulator and its chemical structure. Agric Biol Chem 29:216–221. https://doi.org/10.1080/00021369.1965.1085837
Tamura S, Sakurai A, Kainuma K, Takai M (1963) Isolation of helminthosporol as a natural plant growth regulator and its chemical structure. Agric Biol Chem 27(10):738–739. https://doi.org/10.1080/00021369.1963.10858176
Tao M-H, Yan J, Wei X-Y, Li D-L, Zhang W-M, Tan J-W (2011) A novel sesquiterpene alcohol from Fimetariella rabenhorstii, an endophytic fungus of Aquilaria sinensis. Nat Prod Commun 6:763–766. https://doi.org/10.1177/1934578x1100600605
Tchoukoua A, Ota T, Akanuma R, Ju Y-M, Supratman U, Murayama T, Koseki T, Shiono Y (2017) A phytotoxic bicyclic lactone and other compounds from endophyte Xylaria curta. Nat Prod Res 31:2113–2118. https://doi.org/10.1080/14786419.2016.1277352
Ulloa-Benítez Á, Medina-Romero YM, Sánchez-Fernández RE, Lappe-Oliveras P, Roque-Flores G, Duarte Lisci G, Herrera Suárez T, Macías-Rubalcava ML (2016) Phytotoxic and antimicrobial activity of volatile and semi-volatile organic compounds from the endophyte Hypoxylon anthochroum strain Blaci isolated from Bursera lancifolia (Burseraceae). J Appl Microbiol 121:380–400. https://doi.org/10.1111/jam.13174
Verma VC, Kharwar RN, Strobel GA (2009) Chemical and functional diversity of natural products from plant associated endophytic fungi. Nat Prod Commun 4:1934578X0900401. https://doi.org/10.1177/1934578x0900401114
Vurro M, Evidente A, Andolfi A, Chiara Zonno M, Giordano F, Motta A (1998) Brefeldin A and α,β-dehydrocurvularin, two phytotoxins from Alternaria zinniae, a biocontrol agent of Xanthium occidentale. Plant Sci 138: 67-79 ISSN: 0168-9452
von Wallbrunn C, Luftmann H, Bergander K, Meinhardt F (2001) Phytotoxic chaetoglobosins are produced by the plant pathogen Calonectria morganii (anamorph Cylindrocladium scoparium). J Gen Appl Microbiol. 47:33–38. https://doi.org/10.2323/jgam.47.33
Wang A, Yin R, Zhou Z, Gu G, Dai J, Lai D, Zhou L (2020) Eremophilane-type sesquiterpenoids from the endophytic fungus Rhizopycnis vagum and their antibacterial, cytotoxic, and phytotoxic activities. Front Chem 8:596889. https://doi.org/10.3389/fchem.2020.596889
Wang J, Huang Y, Fang M, Zhang Y, Zheng Z, Zhao Y, Su W (2002) Brefeldin A, a cytotoxin produced by Paecilomyces sp. and Aspergillus clavatus isolated from Taxus mairei and Torreya grandis. Med microbiol immunol 34:51–57. https://doi.org/10.1111/j.1574-695x.2002.tb00602.x
Wang Q, Kong L, Hao H, Wang X, Lin J, Samaj J, Baluska F (2005) Effects of brefeldin A on pollen germination and tube growth. antagonistic effects on endocytosis and secretion. Plant Physiol 139:1692–1703. https://doi.org/10.1104/pp.105.069765
Wang Z-F, Zhang W, Xiao L, Zhou Y-M, Du F-Y (2018) Characterization and bioactive potentials of secondary metabolites from Fusarium chlamydosporum. Nat Prod Res 1–4. https://doi.org/10.1080/14786419.2018.1508142
Wani Z A, Ahmad T, Nalli Y, Ali A, Singh A P, Vishwakarma R A, Ashraf N, Riyaz-Ul-Hassan S (2018) Porostereum sp., associated with saffron (Crocus sativus L.), is a latent pathogen capable of producing phytotoxic chlorinated aromatic compounds. Curr Microbiol 75:880–887. https://doi.org/10.1007/s00284-018-1461-9
Xie J, Wei JG, Wang KW, Luo J, Wu YJ, Luo JT, Yang XB (2020) Three phytotoxins produced by Neopestalotiopsis clavispora, the causal agent of ring spot on Kadsura coccinea. Microbiol Res 238:126531. https://doi.org/10.1016/j.micres.2020.126531
Yan L, Zhu J, Zhao X, Shi J, Jiang C, Shao D (2019) Beneficial effects of endophytic fungi colonization on plants. Appl Microbiol Biotechnol. https://doi.org/10.1007/s00253-019-09713-2
Yang Z, Ge M, Yin Y, Chen Y, Luo M, Chen D (2012) A novel phytotoxic nonenolide from Phomopsis sp. HCCB03520. Chem Biodivers 9:403–408. https://doi.org/10.1002/cbdv.201100080
Yeh CC, Wang CJ, Chen YJ, Tsai S, Chung WH (2021) Potential of a volatile-producing endophytic fungus Nodulisporium sp. PDL-005 for the control of Penicillium digitatum. Biol Control 152(104459). https://doi.org/10.1016/j.biocontrol.2020.104459
Yuan Z, Su Z, Mao L, Peng Y, Yang G, Lin F, Zhang C (2011) Distinctive endophytic fungal assemblage in stems of wild rice (Oryza granulata) in China with special reference to two species of Muscodor (Xylariaceae). J Microbiol 49:15–23. https://doi.org/10.1007/s12275-011-0213-3
Zhang Q, Xiao J, Sun Q-Q, Qin J-C, Pescitelli G, Gao J-M (2014) Characterization of cytochalasins from the endophytic Xylaria sp. and their biological functions. J Agric Food Chem 62:10962–10969. https://doi.org/10.1021/jf503846z
Zhang X-Q, Lu Z-H, Xia G-R, Song W-M, Guo Z-Y, Proksch P (2021) (+)-/(−)-prunomarin A and (+)-pestalactone B, three new isocoumarin derivatives from the endophytic fungus Phomopsis prunorum. Tetrahedron Lett 75:153205. https://doi.org/10.1016/j.tetlet.2021.153205
Code availability
Not applicable.
Funding
This work was funded by the Consejo Nacional de Ciencia y Tecnología, México (CONACyT, grant A1-S-20469) and the Programa de Apoyo a Proyectos de Investigación e Innovación Tecnológica (PAPIIT-DGAPA, UNAM IN210920).
Author information
Authors and Affiliations
Contributions
MR conceptualized the idea and wrote the manuscript. GS contributed to the preparation of the manuscript designed the figures. All two authors have read and approved the manuscript.
Corresponding author
Ethics declarations
Ethics approval
Not applicable.
Consent to participate
Not applicable.
Consent for publication
Not applicable.
Conflict of interest
The authors declare no competing interests.
Additional information
Publisher’s note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Macías-Rubalcava, M.L., Garrido-Santos, M.Y. Phytotoxic compounds from endophytic fungi. Appl Microbiol Biotechnol 106, 931–950 (2022). https://doi.org/10.1007/s00253-022-11773-w
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00253-022-11773-w