Abstract
Botryorhodines K (1) and L (2), two new depsidone derivatives, along with one known metabolite, 4-O-demethylbarbatic acid (3), were isolated from the culture extract of a fungus of the genus Arcopilus. The structures of 1‒3 were determined by the analysis of NMR and MS spectral data and the absolute configuration of 1 was established by single-crystal X-ray diffraction analysis. Compounds 1 and 2 showed antimicrobial activity against Gram-positive bacteria and cytotoxicity against murine leukemia P388 cells.
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References
Bills GF, Gloer JB. Biologically active secondary metabolites from the fungi. Microbiol Spectr. 2016;4:1–32.
Lima LM, Silva BNMD, Barbosa G, Barreiro EJ. β-lactam antibiotics: an overview from a medicinal chemistry perspective. Eur J Med Chem. 2020;208:112829.
Zhang Q, Li HQ, Zong SC, Gao JM. Chemical and bioactive diversities of the genus Chaetomium secondary metabolites. Mini-Rev Med Chem. 2012;12:127–48.
Zhang J, et al. Cytotoxic chaetoglobosins from the endophyte Chaetomium globosum. Planta Med. 2010;76:1910–4.
Ichihara A, Katayama K, Teshima H, Oikawa H, Sakamura S. Chaetoglobosin O and other phytotoxic metabolites from Cylindrocladium floridanum, a causal fungus of alfalfa black rot disease. Biosci Biotechnol Biochem. 1996;60:360–1.
Kanokmedhakul S, Kanokmedhakul K, Phonkerd N, Soytong K, Kongsaeree P, Suksamrarn A. Antimycobacterial anthraquinone-chromanone compound and diketopiperazine alkaloid from the fungus Chaetomium globosum KMITL-N0802. Planta Med. 2002;68:834–6.
Cook KM, Hilton ST, Mecinovic J, Motherwell WB, Figg WD, Schofield CJ. Epidithiodiketopiperazines block the interaction between hypoxia-inducible factor-1α (HIF-1α) and p300 by a zinc ejection mechanism. J Biol Chem. 2009;284:26831–8.
Yang SW, et al. Chemokine receptor CCR-5 inhibitors produced by Chaetomium globosum. J Nat Prod. 2006;69:1025–8.
Phonkerd N, Kanokmedhakul S, Kanokmedhakul K, Soytong K, Prabpai S, Kongsearee P. Bis-spiro-azaphilones and azaphilones from the fungi Chaetomium cochliodes VTh01 and C. cochliodes CTh05. Tetrahedron 2008;64:9636–45.
Wang XW, et al. Diversity and taxonomy of Chaetomium and chaetomium-like fungi from indoor environments. Stud Mycol. 2016;84:145–224.
Dictionary of Natural Products 27.2. CRC Press, Taylor & Francis Group, 2018. http://dnp.chemnetbase.com/. Accessed 10 Jul 2023.
Zhang ZW, et al. Pithohirolide, an antimicrobial tetradepsipeptide from a fungus Pithomyces chartarum. J Antibiot. 2021;74:458–63.
Zhang ZW, et al. Kumemicinones A−G, cytotoxic angucyclinones from a deep sea-derived actinomycete of the genus Actinomadura. J Nat Prod. 2022;85:1098–108.
Liu C, et al. Catellatolactams A−C, plant growth-promoting ansamacrolactams from a rare actinomycete of the genus Catellatospora. J Nat Prod. 2022;85:1993–9.
Huneck S. tert-Butanolysis of lichen depsides. Phytochemistry 1987;23:2697–8.
Shang Z, et al. Roseopurpurins: chemical diversity enhanced by convergent biosynthesis and forward and reverse michael additions. Org Lett. 2016;18:4340–3.
Abdou R, Scherlach K, Dahse HM, Sattler I, Hertweck C. Botryorhodines A-D, antifungal and cytotoxic depsidones from Botryosphaeria rhodina, an endophyte of the medicinal plant Bidens pilosa. Phytochemistry 2010;71:110–6.
Chen S, Liu Z, Liu Y, Lu Y, He L, She Z. New depsidones and isoindolinones from the mangrove endophytic fungus Meyerozyma guilliermondii (HZ-Y2) isolated from the south China sea. Beilstein J Org Chem. 2015;11:1187–93.
Pang XY, et al. Spiro-phthalides and isocoumarins isolated from the marine-sponge-derived fungus Setosphaeria sp. SCSIO41009. J Nat Prod. 2018;81:1860–8.
Duan HJ, et al. Zinniol analogues from the endophytic fungus Arcopilus sp. YUD20001 associated with Gastrodia elata. Phytochem Lett. 2022;51:140–4.
Karim MRU, Harunari E, Oku N, Akasaka K, Igarashi Y. Bulbimidazoles A−C, antimicrobial and cytotoxic alkanoyl imidazoles from a marine gammaproteobacterium Microbulbifer species. J Nat Prod. 2020;83:1295–9.
Acknowledgements
P388 cells were obtained from JCRB Cell Bank under an accession code JCRB0017 (Lot. 06252002). We also thank Ms. Desy Wulan Triningsih at Toyama Prefectural University for cytotoxicity assay.
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Supplementary Information for Botryorhodines K‒L, two new cytotoxic depsidones from fungus of the genus<i> Arcopilus</i>
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Zhang, Z., Ge, Y., In, Y. et al. Botryorhodines K and L, two new cytotoxic depsidones from a fungus of the genus Arcopilus. J Antibiot 76, 673–677 (2023). https://doi.org/10.1038/s41429-023-00652-9
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DOI: https://doi.org/10.1038/s41429-023-00652-9