Abstract
Natural coumarins and derivatives are compounds that occur naturally in several organisms (plant, bacteria, and fungi) consisting of fused benzene and α-pyrone rings. These compounds show high technological potential applications in agrochemical, food, pharmaceuticals, and cosmetics industries. Therefore, the need for bulk production of coumarins and the advancement of the chemical and pharmaceutical industries led to the development of synthetic coumarin. However, biotransformation process, synthetic bioengineering, metabolic engineering, and bioinformatics have proven effective in the production of natural products. Today, these biological systems are recognized as green chemistry innovation and business strategy. This review article aims to report the potential of fungi for synthesis of coumarin. These microorganisms are described as a source of natural products capable of synthesizing many bioactive metabolites. The features, classification, properties, and industrial applications of natural coumarins as well as new molecules obtained by basidiomycetes and ascomycetes fungi are reported in order to explore a topic not yet discussed in the scientific literature.
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References
Abdel-Wahab BF, Mohamed HA, Farhat AA (2014) Ethyl coumarin-3-carboxylate: synthesis and chemical properties. Org Commun 7:1–27
Aguirre-Pranzoni C, Orden AA, Bisogno FR, Ardanaz CE, Tonn CE, Kurina-Sanz M (2011) Coumarin metabolic routes in Aspergillus spp. Fungal Biol 115:245–252. doi:10.1016/j.funbio.2010.12.009
Anand P, Singh B, Singh N (2012) A review on coumarins as acetylcholinesterase inhibitors for Alzheimer’s disease. Bioorg Med Chem 20:1175–1180. doi:10.1016/j.bmc.2011.12.042
Aslam K, Khosa MK, Jahan N, Nosheen S (2010) Synthesis and applications of coumarin. Pak J Pharm Sci 23:449–454
Awe S, Mikolasch A, Schauer F (2009) Formation of coumarines during the degradation of alkyl substituted aromatic oil components by the yeast Trichosporon asahii. Appl Microbiol Biotechnol 84:965–976. doi:10.1007/s00253-009-2044-2
Baranyi N, Kocsubé S, Varga J (2015) Aflatoxins: climate change and biodegradation. Curr Opin Food Sci 5:60–66. doi:10.1016/j.cofs.2015.09.002
Bbosa GS, Kitya D, Odda J, Ogwal-Okeng J (2013a) Aflatoxins metabolism, effects on epigenetic mechanisms and their role in carcinogenesis. Health 5:14–34. doi:10.4236/health.2013.510A1003
Bbosa GS, Kitya D, Lubega A, Ogwal-Okeng J, Anokbonggo WW, Kyegombe DB (2013b) Review of the biological and health effects of aflatoxins on body organs and body systems. INTECH 12:239–265. doi:10.5772/51201
Bertin RL, Gonzaga LV, Borges GSC, Azevedo MS, Maltez HF, Heller M, Micke GA, Tavares LBB, Fett R (2014) Nutrient composition and, identification/quantification of major phenolic compounds in Sarcocornia ambigua (Amaranthaceae) using HPLC–ESI-MS/MS. Food Res Int 55:404–411. doi:10.1016/j.foodres.2013.11.036
Bocks SM (1967) Fungal metabolism—I.: the transformations of coumarin, o-coumaric acid and trans-cinnamic acid by Aspergillus niger. Phytochemistry 6:127–130. doi:10.1016/0031-9422(67)85017-9
Borderes J, Costa A, Guedes A, Tavares LBB (2011) Antioxidant activity of the extracts from Pycnoporus sanguineus mycelium. Braz Arch Biol Technol 54:1167–1174. doi:10.1590/S1516-89132011000600012
Cao JL, Shen SL, Yang P, Qu J (2013) A catalyst-free one-pot construction of skeletons of 5-methoxyseselin and alloxanthoxyletin in water. Org Lett 15:3856–3859. doi:10.1021/ol401581p
Craveri Company. http://www.craveri.com.ar/es. Accessed 02 Apr 2016
Daru J, Stirling A (2011) Mechanism of the Pechmann reaction: a theoretical study. J Organomet Chem 76:8749–8755. doi:10.1021/jo201439u
Demain AL (2014) Valuable secondary metabolites from fungi. In: Martin JF, Garcia-Estrada C, Zeilinger S (eds) Biosynthesis and molecular genetics of fungal secondary metabolites. Springer, New York, pp. 1–16
Drawert F, Berger RG, Neuhäuser K (1983) Biosynthesis of flavor compounds by microorganisms 4. Characterization of the major principles of the odor of Pleurotus euosmus*. Appl Microbiol Biotechnol 18:124–127. doi:10.1007/BF00500836
Eaton DL, Gallagher EP (1994) Mechanisms of aflatoxins carcinogenesis. Annu Rev Pharmacol Toxicol 34:135–172
Egan D, O’Kennedy R, Moran E, Cox D, Prosser E, Thornes D (1990) The pharmacology, metabolism, analysis, and applications of coumarin and coumarin-related compounds*. Drug Metab Rev 22:503–529
Emami S, Dadashpour S (2015) Current developments of coumarin-based anti-cancer agents in medicinal chemistry. Eur J Med Chem 102:611–630. doi:10.1016/j.ejmech.2015.08.033
Gestetner B, Conn EE (1974) The 2-hydroxylation of trans-cinnamic acid by chloroplasts from Melilotus alba. Desr Arch Biochem Biophys 163:617–624
Hadibarata T, Kristanti RA (2012) Identification of metabolites from benzo[a]pyrene oxidation by ligninolytic enzymes of Polyporus sp. S133. J Environ Manag 111:115–119. doi:10.1016/j.jenvman.2012.06.044
Han Z, Mei W, Zhao Y, Deng Y, Dai H (2009) A new cytotoxic isocoumarin from endophytic fungus Penicillium SP. 09142 of the mangrove plant Bruguiera sexangula. Chem Nat Compd 45:805–807. doi:10.1007/s10600-010-9503-y
Hansen GH, Lübeck M, Frisvad JC, Lübeck PS, Andersen B (2015) Production of cellulolytic enzymes from ascomycetes: comparison of solid state and submerged fermentation. Process Biochem 50:1327–1341. doi:10.1016/j.procbio.2015.05.017
Häser K, Wenk HH, Schwab W (2006) Biocatalytic production of dihydrocoumarin from coumarin by Saccharomyces cerevisiae. J Agric Food Chem 54:6236–6240. doi:10.1021/jf061334w
Haskins FA, Williams LG, Gorz HJ (1964) Light-induced trans to cis conversion of beta-d-glucosyl o-hydroxycinnamic acid in Melilotus alba leaves. Plant Physiol 39:777–781
Hasnat MA, Pervin M, Lim BO (2013) Acetylcholinesterase inhibition and in vitro and in vivo antioxidant activities of Ganoderma lucidum grown on germinated brown rice. Molecules 18:6663–6678. doi:10.3390/molecules18066663
Hasnat MA, Pervin M, Cha KM, Kim SK, Lim B (2015) Anti-inflammatory activity on mice of extract of Ganoderma lucidum grown on rice via modulation of MAPK and NF-kB pathways. Phytochemistry 114:125–136. doi:10.1016/j.phytochem.2014.10.019
Hara KY, Araki M, Okai N, Wakai S, Hasunuma T, Kondo A (2014) Development of bio-based fine chemical production through synthetic bioengineering. Microb Cell Factories 13(173):1–18. doi:10.1186/s12934-014-0173-5
He JW, Qin DP, Gao H, Kuang RQ, Yu Y, Liu XZ, Yao XS (2014) Two new coumarins from Talaromyces flavus. Molecules 19:20880–20887. doi:10.3390/molecules191220880
He X, Shang Y, Zhou Y, Yu G, Han G, Jin W, Chen J (2015) Synthesis of coumarin-3-carboxylic esters via FeCl3-catalyzed multicomponent reaction of salicylaldehydes, Meldrum’s acid and alcohols. Tetrahedron 71:863–868. doi:10.1016/j.tet.2014.12.042
Hossain CF, Okuyama E, Yamazaki M (1996) A new series of coumarin derivatives having monoamine oxidase inhibitory activity from Monascus anka. Chem Pharm Bull 44:1535–1539
Hrobonová K, Spevak A, Spisská L, Lehotay J, Cizmárik J (2013) Application of umbelliferone molecularly imprinted polymer in analysis of plant samples. Chem Pap 67:477–483. doi:10.2478/s11696-013-0320-1
Hwan Do J, Choi DK (2007) Aflatoxins: detection, toxicity, and biosynthesis. Biotechnol Bioprocess Eng 12:585–593. doi:10.1007/BF02931073
Hwang CH, Jaki BU, Klein LL, Lankin DC, McAlpine JB, Napolitano JG, Fryling NA, Franzblau SG, Cho SH, Stamets PE, Wang Y, Pauli GF (2013) Cholinated coumarins from the polypore mushroom Fomitopsis officialis and their activity against Mycobacterium tuberculosis. J Nat Prod 76:1916–1922. doi:10.1021/np400497f
INDOFINE Chemical Company. http://indofinechemical.com. Accessed 03 March 2016
Islam MR, Omar M, Moyen Uddin PK, Mia MR, Kamrunnahar M (2015) Phytochemicals and antibacterial activity screening of three edible mushrooms Pleurotus ostreatus, Ganoderma lucidum and Lentinula edodes accessible in Bangladesh. Am J Biol Life Sci 3:31–35
Jain PK, Joshi H (2012) Coumarin: chemical and pharmacological profile. J Appl Pharm Sci 2:236–240. doi:10.7324/JAPS.2012.2643
Jeong-Cho H, Jeong SG, Park JE, Han JA, Kang HR, Lee D, Song MJ (2013) Antiviral activity of angelicin against gammaherpesviruses. Antivir Res 100:75–83. doi:10.1016/j.antiviral.2013.07.009
Jun M, Bacay AF, Moyer J, Webb A, Carrico-Moniz D (2014) Synthesis and biological evaluation of isoprenylated coumarins as potential anti-pancreatic cancer agents. Bioorg Med Chem Lett 24:4654–4658. doi:10.1016/j.bmcl.2014.08.038
Jung JC, Park OS (2009) Synthetic approaches and biological activities of 4-hydroxycoumarin derivatives. Molecules 14:4790–4803. doi:10.3390/molecules14114790
Kalita P, Kumar R (2012) Solvent-free coumarin synthesis via Pechmann reaction using solid catalysts. Microporous Mesoporous Mater 149:1–9. doi:10.1016/j.micromeso.2011.08.004
Keri RS, Sasidhar BS, Nagaraja BM, Amélia Santos M (2015) Recent progress in the drug development of coumarin derivatives as potent antituberculosis agents. Eur J Med Chem 100:257–269. doi:10.1016/j.ejmech.2015.06.017
Khan AA, Bacha N, Ahmad B, Lutfullah G, Farooq U, Cox RJ (2014) Fungi as chemical industries and genetic engineering for the production of biologically active secondary metabolites. Asian Pac J Trop Biomed 4:859–870. doi:10.12980/APJTB.4.2014APJTB-2014-0230
Kleinhofs A, Haskins FA, Gorz HJ (1967) Trans-o-hydroxycinnamic acid glucosylation in cell-free extracts of Melilotus alba. Phytochemistry 6:1313–1318
Koukol J, Conn EE (1961) The metabolism of aromatic compounds in higher plants. J Biol Chem 236:2692–2698
Kumar AS, Kanakaraju S, Prasanna B, Chandramouli GVP (2013) Synthesis, molecular docking studies and antibacterial evaluation of Baylis-Hillman adducts of coumarin and pyran derivatives using ionic liquid under microwave irradiation. Chem Sci Trans 2:561–569. doi:10.7598/cst2013.415
Lacy A, O’Kennedy R (2004) Studies on coumarins and coumarin-related compounds to determine their therapeutic role in the treatment of cancer. Curr Pharm Des 10:3797–3811
Leontopoulos D, Siafaka A, Markaki P (2003) Black olives as substrate for Aspergillus parasiticus growth and aflatoxin B1 production. Food Microbiol 20:119–126. doi:10.1016/S0740-0020(02)00080-1
Liaud N, Giniés C, Navarro D, Fabre N, Crapart S, Herpoël-Gimbert I, Levasseur A, Raouche S, Sigoillot JC (2014) Exploring fungal biodiversity: organic acid production by 66 strains of filamentous fungi. Fungal Biol Biotechnol 1:1–10. doi:10.1186/s40694-014-0001-z
Lin Y, Shen X, Yuan Q, Yan Y (2013a) Microbial biosynthesis of the anticoagulant precursor 4-hydroxycoumarin. Nat Commun 4(2603):1–8. doi:10.1038/ncomms3603
Lin Y, Sun X, Yuan Q, Yan Y (2013b) Combinatorial biosynthesis of plant-specific coumarins in bacteria. Metab Eng 18:69–77. doi:10.1016/j.ymben.2013.04.004
Liu X, Dong M, Chen X, Jiang M, Lv X, Zhou J (2008) Antimicrobial activity of an endophytic Xylaria sp.YX-28 and identification of its antimicrobial compound 7-amino-4-methylcoumarin. Appl Microbiol Biotechnol 78:241–247. doi:10.1007/s00253-007-1305-1
Lv X, Liu D, Hou J, Dong P, Zhan L, Wang L, Deng S, Wang C, Yao J, Shu X, Liu K, Ma X (2013) Biostransformation of imperatorin by Penicillium janthinellum. Anti-osteoporosis activities of its metabolites. Food Chem 138:2260–2266. doi:10.1016/j.foodchem.2012.11.138
Ma XK, Li L, Peterson EC, Ruan T, Duan X (2015) The influence of naphthaleneacetic acid (NAA) and coumarin on flavonoid production by fungus Phellinus sp.: modeling of production kinetic profiles. Appl Microbiol Biotechnol 99:9417–9126. doi:10.1007/s00253-015-6824-6
Mao WW, Wang TT, Zeng HP, Wang ZY, Chen JP, Shen JG (2009) Synthesis and evaluation of novel substituted 5-hydroxycoumarin and pyranocoumarin derivatives exhibiting significant antiproliferative activity against breast cancer cell lines. Bioorg Med Chem Lett 19:4570–4573. doi:10.1016/j.bmcl.2009.06.098
Martins SMA, Branco PCS, Pereira AMDRL (2012) An efficient methodology for the synthesis of 3-styryl coumarins. J Braz Chem Soc 23:688–693. doi:10.1590/S0103-50532012000400014
Matos MJ, Santana L, Uriarte E, Abreu OA, Molina E, Yordi EG (2015) Coumarins—an important class of phytochemicals. In: Rao V, Rao LG (ed) Phytochemicals—isolation, characterisation and role in human health, ISBN: 978-953-51-2170-1. pp 113–140. doi:10.5772/59982. http://www.intechopen.com/books/phytochemicals-isolation-characterisation-and-role-in-human-health/coumarins-an-important-class-of-phytochemicals. Accessed 25 March 2016
Matsuzaki F, Wariischi H (2004) Functional diversity of cytochrome P450s of the white-rot fungus Phanerochaete chrysosporium. Biochem Biophys Res Commun 324:387–393. doi:10.1016/j.bbrc.2004.09.062
Miyano DM, Lima T, Simões FR, La-Scalea MA, Oliveira HPM, Codognoto L (2014) Electrochemical study of simple coumarin and its determination in aqueous infusion of Mikania glomerata. J Braz Chem Soc 25:602–609. doi:10.5935/0103-5053.20140046
Molina FT, Zanusso Júnior G (2014) Coumarin anticoagulants: actions, risks and therapeutic monitoring. SaBios: Rev Saúde Biol 9:75–82
Myung K, Manthey JA, Narciso JA (2012) Biotransformations of 6′,7′-dihydroxybergamottin and 6′,7′-epoxybergamottin by the citrus-pathogenic fungi diminish cytochrome P450 3 A4 inhibitory activity. Bioorg Med Chem Lett 22:2279–2282. doi:10.1016/j.bmcl.2012.01.081
Mogland EHO, Saadabi AM (2012) Screening of antimicrobial activity of wild mushrooms from Khartoum state of Sudan. Microbiol J 2:64–69. doi:10.3923/mj.2012.64.69
Mueller RL (2004) First-generation agents: aspirin, heparin and coumarins. Best Pract Res Clin Haematol 17:23–53. doi:10.1016/j.beha.2004.03.003
Nikhil B, Shikha B, Anil P, Prakash NB (2012) Diverse pharmacological activities of 3-substituted coumarins: a review. Int Res J Pharm 3:24–29
Oba K, Conn EE, Canut H, Boudet AM (1981) Subcellular localization of 2-(beta-d-glucosyloxy)-cinnamic acids and the related beta-glucosidase in leaves of Melilotus alba Desr. Plant Physiol 68:1359–1363
Parshikov IA, Woodling KA, Sutherland JB (2015) Biotransformations of organic compounds mediated by cultures of Aspergillus niger. Appl Microbiol Biotechnol 99:6971–6986. doi:10.1007/s00253-015-6765-0
Patil PO, Bari SB, Firke SD, Deshmukh PK, Donda ST, Patil DA (2013) A comprehensive review on synthesis and designing aspects of coumarin derivatives as monoamine oxidase inhibitors for depression and Alzheimer’s disease. Bioorg Med Chem 21:2434–2450. doi:10.1016/j.bmc.2013.02.017
Pirmohamed M (2006) Warfarin: almost 60 years old and still causing problems. Br J Clin Pharmacol 62:509–511. doi:10.1111/j.1365-2125.2006.02806.x
Rehman S, Rahman M, Tripathi VK, Singh J, Ara T, Koul S, Farroq S, Kaul A (2014) Synthesis and biological evaluation of novel isoxazoles and triazoles linked 6-hydroxycoumarin as potent cytotoxic agents. Bioorg Med Chem Lett 24:4243–4246. doi:10.1016/j.bmcl.2014.07.031
Rohini K, Srikumar PS (2014) Therapeutic role of coumarins and coumarin-related compounds. J Thermodyn Catal 5:1–3. doi:10.4172/2157-7544.1000130
Sandhu S, Bansal Y, Silakari O, Bansal G (2014) Coumarin hybrids as novel therapeutic agents. Bioorg Med Chem 22:3806–3814. doi:10.1016/j.bmc.2014.05.032
Santos WH, Souza M, Siqueira L, Silva-Filho LC (2013) Synthesis of 4-aryl-3,4-dihydrocoumarin derivatives catalyzed by NbCl5. Quim Nov. 36:1303–1307. doi:10.1590/S0100-40422013000900005
Shi X, Liu M, Zhang M, Zhang K, Liu S, Qiao S, Shi R, Xijuan J, Wang Q (2013) Identification of in vitro and in vivo metabolites of imperatorim using liquid chromatography/mass spectrometry. Food Chem 141:357–365. doi:10.1016/j.foodchem.2013.02.068
Shirmila JG, Radhamany PM (2013) Invitro antioxidant activities, total phenolics and flavonoid of wild edible mushroom Macrolepiota mastoidea (FR.) Singer. Int J Pharm Pharm Sci 5:161–166
Stanchev S, Hadjimitova V, Traykov T, Boyanov T, Manolov I (2009) Investigation of the antioxidant properties of some new 4-hydroxycoumarin derivatives. Eur J Med Chem 44:3077–3082. doi:10.1016/j.ejmech.2008.07.007
Steffensky M, Mühlenweg A, Wang ZX, Li SM, Heide L (2000) Identification of the novobiocin biosynthetic gene cluster of Streptomyces spheroides NCIB 11891. Antimicrob Agents Chemother 44:1214–1222
Sun X, Shen X, Jain R, Lin Y, Wang J, Sun J, Wang J, Yan Y, Yuan Q (2015) Synthesis of chemicals by metabolic engineering of microbes. Chem Soc Rev 44:3760–3785. doi:10.1039/c5cs00159e
Symeonidis T, Chamilos M, Hadjipavlou-Litina DJ, Kallitsakis M, Litinas KE (2009) Synthesis of hydroxycoumarins and hydroxybenzo[f]- or [h]coumarins as lipid peroxidation inhibitors. Bioorg Med Chem Lett 19:1139–1142. doi:10.1016/j.bmcl.2008.12.098
Szumski M, Grzywinski D, Prus W, Buszewski B (2014) Monolithic molecularly imprinted polymeric capillary columns for isolation of aflatoxins. J Chromatogr A 1364:163–170. doi:10.1016/j.chroma.2014.08.078
Takeda Russia/CIS. http://www.takeda.com.ru/en/products/. Accessed 02 Apr 2016
Tandon R, Ponnan P, Aggarwal N, Pathak R, Baghel AS, Gupta G, Arya A, Nath M, Parmar VS, Raj HG, Prasad AK, Bose M (2011) Characterization of 7-amino-4-methylcoumarin as an effective antitubercular agent: structure–activity relationships. J Antimicrob Chemother 66:2543–2555. doi:10.1093/jac/dkr355
Vannelli T, Qi WW, Sweigard J, Gatenby AA, Sariaslani SF (2007) Production of p-hydroxycinnamic acid from glucose in Saccharomyces cerevisiae and Escherichia coli by expression of heterologous genes from plants and fungi. Metab Eng 9:142–151. doi:10.1016/j.ymben.2006.11.001
Venugopala KN, Rashmi V, Odhav B (2013) Review on natural coumarin lead compounds for their pharmacological activity. BioMed Res Int 2013:963248 . doi:10.1155/2013/9632481-14
Vekariya RH, Patel HD (2014) Recent advanced in the synthesis of coumarin derivatives via Knoevenagel condensation: a review. Synth Commun 40:2756–2788. doi:10.1080/00397911.2014.926374
Vieira GRT, Liebl M, Tavares LBB, Paulert R, Smânia Junior A (2008) Submerged culture conditions for the production of mycelial biomass and antimicrobial metabolites by Polyporus tricholoma Mont. Braz J Microbiol 39:561–568. doi:10.1590/S1517-838220080003000029
Vila Nova PCC, Vilegas JHY, Lanças FM, Arruda EJ, Oliveira LCS (2012) Analysis of coumarin derivatives of citrus using high resolution gas chromatography with detection systems flame ionization mass spectrometry. J Biotechnol Biodivers 3:25–31
Wang Y, Wang Y, Li P, Tang Y, Fawcett JP, Gu J (2007) Quantitation of Armillarisin A in human plasma by liquid chromatography–electrospray tandem mass spectrometry. J Pharm Biomed Anal 43:1860–1863. doi:10.1016/j.jpba.2006.12.023
Wang X, Mao ZG, Song BB, Chen CH, Xiao WW, Hu B, Wang JW, Jiang XB, Zhu YH, Wang HJ (2013) Advances in the study of the structures and bioactivities of metabolites isolated from mangrove-derived fungi in the South China Sea. Mar Drugs 11:3601–3616. doi:10.3390/md11103601
Wang X, Niessner R, Tang D, Knopp D (2016) Review: nanoparticle-based immunosensors and immunoassays for aflatoxins. Anal Chim Acta 912:10–23. doi:10.1016/j.aca.2016.01.048
Xu J, Kjer J, Sendker J, Wray V, Guan H, Edrada R, Müller WEG, Bayer M, Lin W, Wu J, Proksch P (2009) Cytosporones, coumarins, and alkaloid from the endophytic fungus Pestalotiopsis sp. isolated from the Chinese mangrove plant Rhizophora mucronata. Bioorg Med Chem 17:7362–7367. doi:10.1016/j.bmc.2009.08.031
Yang X, Hou J, Liu D, Deng S, Wang ZB, Kuang HX, Wang CY, Yao JK, Liu KX, Ma CX (2013) Biotransformation of isoimperatorin by Cunninghamella blakesleana AS 3.970. J Mol Catal B Enzym 88:1–6. doi:10.1016/j.molcatb.2012.11.012
Yodoshi M, Tani A, Ohta Y, Suzuki S (2008) Optimized conditions for high-performance liquid chromatography analysis of oligosaccharides using 7-amino-4-methylcoumarin as a reductive amination reagent. J Chromatogr A 1203:137–145. doi:10.1016/j.chroma.2008.07.053
Yu J (2012) Current understanding on aflatoxin biosynthesis and future perspective in reducing aflatoxin contamination. Toxins 4:1024–1057. doi:10.3390/toxins4111024
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The authors are thankful to the Coordination for the Improvement of Higher Education Personnel (CAPES) for financial support. The authors D. Oliveira and L.B.B. Tavares are fellowship holders of the National Council for Scientific and Technological Development (CNPq).
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Tania Maria Costa declares that she has no conflict of interest.
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Costa, T.M., Tavares, L.B.B. & de Oliveira, D. Fungi as a source of natural coumarins production. Appl Microbiol Biotechnol 100, 6571–6584 (2016). https://doi.org/10.1007/s00253-016-7660-z
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DOI: https://doi.org/10.1007/s00253-016-7660-z