Phytotoxic naphtho-γ-pyrones from an endophytic fungus Aspergillus niger from Basella alba

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Research Articles | Published:

E-ISSN: 2229-4473.
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DOI: 10.1007/s42535-025-01515-4
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Keywords: n Aspergillus nigern , n Basella alban , Endophytic fungi, Naphtho-γ-pyrones, Phytotoxicity


Abstract

Fermentation of Aspergillus niger isolated from the leaves of Basella alba in potato dextrose broth medium furnished five naphtho-γ-pyrone type compounds, TMC 256A1 (1), rubrofusarin B (2), fonsecin B (3), aurasperone A (4) and fonsecinone A (5). Compounds 1, 2 and 3 showed remarkable phytotoxic activity in lettuce seed germination bioassay with IC50 values of 45.4, 49.7 and 47.8 ppm percentage radicle growth inhibition, respectively, while IC50 values for percentage hypocotyl growth inhibition were 49.7, 48.7 and 48.2 ppm, respectively. This is the first report on the isolation of A. niger from Basella alba and the phytotoxic activity of compounds 1–3 in lettuce seed germination assay.



References

Abdelwahab GM, Mira A, Chen YB, Abdelaziz TA, Lahloub MFI, Khalil AT (2021) Acetylcholineesterase inhibitory activity of green synthesized nanosilver by naphthopyrones isolated from marine derived Aspergillus niger. PLoS ONE 16(9):e0257071. https://doi.org/10.1371/journal.pone.0257071


Bandara HMSKH, Kumar NS, Jayasinghe L, Masubuti H, Fujimoto Y (2015) A 3-vinyl cephem derivative, useful intermediate in the synthesis of cephem antibiotics, from Aspergillus awamori associated with banana fruit. Nat Prod Commun 10(10):1663–1666


Campos FR, Barison A, Daolio C, Ferreira AG, Rodrigues-Fo E (2005) Complete 1H and 13C NMR assignments of aurasperone A and fonsecinone A, two bis-naphthopyrones produced by Aspergillus aculeatus. Magn Reson Chem 43(11):962–965


Dissanayake D, Kumar NS, Adikaram NKB, Jayasinghe L, Araya H, Fujimoto Y (2020) Production of small molecules by an endophytic fungus, Neofusicoccum parvum from the fruits of Elaeocarpus serratus. Asian J Tradit Med 15(2):20–27


Huang HB, Feng XJ, Liu L, Chen B, Lu YJ, Ma L, Lin YC (2010) Three dimeric naphtho-γ-pyrones from the mangrove endophytic fungus Aspergillus tubingensis isolated from Pongamia pinnata. Planta Med 76(16):1888–1891


Jayaweera DM (1981) Medicinal plants used in Ceylon Part I. The National Science Council of Sri Lanka, Colombo


Kehelpannala CL, Kumar NS, Jayasinghe L, Araya H, Fujimoto Y (2018) Naphthoquinonemetabolites produced by Monacrosporium ambrosium, the ectosymbiotic fungus of tea shot-hole borer, Euwallacea fornicatus, in stems of tea, Camellia sinensis. J Chem Ecol 44(1):95–101


Kehelpannala C, Rathnayake GRN, Dissanayake D, Kanatiwela D, Kumar NS, Adikaram N, Jayasinghe L, Araya H, Fujimoto Y (2021) Determination of the absolute stereochemistry of (+)-solaniol. Chem Pap 75:2233–2235


Lai D, Meng J, Xu D, Zhang X, Liang Y, Han Y, Jiang C, Liu H, Wang C, Zhou L, Xu JR (2019) Determination of the absolute configurations of the stereogenic centers of ustilaginoidins by studying the biosynthetic monomers from a gene knockout mutant of Villosiclava virens. Sci Rep 9:1855. https://doi.org/10.1038/s41598-018-37941-5


Leutou AS, Yu K, Son BW (2016) Induced production of 6,9-dibromoflavasperone, a new radical scavenging naphthopyranone in the marine-mudflat-derived fungus Aspergillus niger. Arch Pharm Res 39(6):806–810


Macías M, Ulloa M, Gamboa A, Mata R (2000) Phytotoxic compounds from the new coprophilous fungus Guanomyces polythrix. J Nat Prod 63(6):757–761


Munasinghe MVK, Kumar NS, Jayasinghe L, Fujimoto Y (2017) Indole-3-acetic acid production by Colletotrichum siamense, an endophytic fungus from Piper nigrum leaves. J Biol Act Prod Nat 7(6):475–479


Munasinghe MVK, Kumar NS, Adikaram NKB, Jayasinghe L, Araya H, Fujimoto Y (2021) Secondary metabolites from an endophytic fungus Aspergillus fumigatus from Solanum insanum L. Asian J Tradit Med 16(2):53–59


Padmathilake KGE, Bandara HMSKH, Qader MM, Kumar NS, Jayasinghe L, Masubuti H, Fujimoto Y (2017) Talarofuranone, a new talaroconvolutin analog from the endophytic fungus Talaromyces purpurogenus from Pouteria campechiana seeds. Nat Prod Commun 12(14):489–490


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. Mycology 6(3–4):158–160


Qader MM, Kumar NS, Jayasinghe L, Fujimoto Y (2016) Production of antitumor antibiotic GKK1032B by Penicillium citrinum, an endophytic fungus isolated from Garcinia mangostana fruits. Med Aromatic Plant 5(1):225


Qader MM, Kumar NS, Jayasinghe L, Araya H, Fujimoto Y (2017a) Bioactive sesquiterpenes from an endophytic fungus Bipolaris sorokiniana isolated from a popular medicinal plant Costus speciosus. Mycology 8(1):17–20


Qader MM, Kumar NS, Jayasinghe L, Fujimoto Y (2017b) Shikimic acid production by Fusarium decemcellulare, an endophytic fungus isolated from Flacourtia inermis fruits. J Biol Active Prod Nat 8(1):43–50


Rathnayake GRN, Kumar NS, Jayasinghe L, Araya H, Fujimoto Y (2018) Chemical investigation of metabolites produced by an endophytic fungi Phialemonium curvatum from the leaves of Passiflora edulis. Nat Prod Res 32(20):2483–2486


Rathnayake GRN, Kumar NS, Jayasinghe L, Araya H, Fujimoto Y (2019) Secondary metabolites produced by an endophytic fungus Pestalotiopsis microspora. Nat Prod Bioprospect 9(6):411–417


Shaaban M, Shaaban KA, Abdel-Aziz MS (2012) Seven naphtho-γ-pyrones from the marine-derived fungus Alternaria alternata: structure elucidation and biological properties. Org Med Chem Lett 2:6. https://doi.org/10.1186/2191-2858-2-6


Siriwardane AMDA, Kumar NS, Jayasinghe L, Fujimoto Y (2015) Chemical investigation of metabolites produced by an endophytic Aspergillus sp. isolated from Limonia acidissima. Nat Prod Res 29(14):1384–1387


Sritharan T, Kumar NS, Jayasinghe L, Araya H, Fujimoto Y (2019) Isocoumarins and dihydroisocoumarins from the endophytic fungus Biscogniauxia capnodes isolated from the fruits of Averrhoa carambola. Nat Prod Commun 14(5):1934578X19851969


Sun W, Wang A, Xu D, Wang W, Meng J, Dai J, Liu Y, Lai D, Zhou L (2017) New ustilaginoidinsfrom rice false smut balls caused by Villosiclava virens and their phytotoxic and cytotoxic activities. J Agric Food Chem 65(25):5151–5160


Suwitchayanon P, Kato-Noguchi H (2014) Allelopathic activity of leaves, stalks and roots of Cymbopogon nardus. Emir J Food Agric 26(5):436–443


Thanabalasingam D, Kumar NS, Jayasinghe L, Fujimoto Y (2015) Endophytic fungus Nigrospora oryzae from a medicinal plant Coccinia grandis, a high yielding new source of phenazine-1-carboxamide. Nat Prod Commun 10(10):1659–1660


Thanabalasingam D, Dissanayake D, Samarakoon K, Kumar NS, Adikaram N, Jayasinghe L, Araya H, Fujimoto Y (2024) Oryzanigral: a new polyketide from an endophytic fungus Nigrospora oryzae isolated from Coccinia grandis. Nat Prod Res 38(15):2703–2710


Yu R, Liu J, Wang Y, Wang H, Zhang H (2021) Aspergillus niger as a secondary metabolite factory. Front Chem 9:701022

 


Author Information

National Institute of Fundamental Studies, Kandy, Sri Lanka