Abstract
A new dimeric 5-hydroxy-2-hexenoic acid, clonohexenoic acid (1), a known 14-membered macrolide, acremodiol B (2), and two known benzochromenone derivatives, alternariol (3) and 2-hydroxyalternariol (4), were isolated from a culture broth of Clonostachys rogersoniana. The structures of these isolated compounds were determined using spectroscopic methods. Antimicrobial and cytotoxic activities of these compounds were then assessed. Compounds 1‒4 exhibited antimicrobial activities against Bacillus subtilis and Propionibacterium acnes. In addition, compounds 3 and 4 showed antibacterial activities against B. cereus and cytotoxic activities against three human cancer cell lines, A549, HCT-116, and Mia Paca-2.
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References
Schroers HJ. A monograph of Bionectria (Ascomycota, Hypocreales, Bionectriaceae) and its Clonostachys anamorphs. Stud Mycol. 2001;46:1–214.
Chen WH, Han YF, Liang JD, Zou X, Liang ZQ, Jin DC. A new araneogenous fungus of the genus Clonostachys. Mycosystema. 2016;35:1061–9.
Torcato C, Gonçalves MF, Rodríguez-Gálvez E, Alves A. Clonostachys viticola sp. nov., a novel species isolated from Vitis vinifera. Int J Syst Evol Microbiol. 2020;70:4321–8.
Sun ZB, Li SD, Ren Q, Xu JL, Lu X, Sun MH. Biology and applications of Clonostachys rosea. J Appl Microbiol. 2020;129:486–95.
Cota LV, Maffia LA, Mizubuti ES, Macedo PE, Antunes RF. Biological control of strawberry gray mold by Clonostachys rosea under field conditions. Biol Control. 2008;46:515–22.
Cruz LJ, Insua MM, Baz JP, Trujillo M, Rodriguez-Mias RA, Oliveira E, et al. IB-01212, a new cytotoxic cyclodepsipeptide isolated from the marine fungus Clonostachys sp. ESNA-A009. J Org Chem. 2006;71:3335–8.
Abdel-Wahab NM, Harwoko H, Müller WE, Hamacher A, Kassack MU, Fouad MA, et al. Cyclic heptapeptides from the soil-derived fungus Clonostachys rosea. Bioorg Med Chem. 2019;27:3954–9.
Zhai MM, Qi FM, Li J, Jiang CX, Hou Y, Shi YP, et al. Isolation of secondary metabolites from the soil-derived fungus Clonostachys rosea YRS-06, a biological control agent, and evaluation of antibacterial activity. J Agric Food Chem. 2016;64:2298–306.
Zhu S, Ren F, Guo Z, Liu J, Liu X, Liu G, et al. Rogersonins A and B, imidazolone N-oxide-incorporating indole alkaloids from a verG disruption mutant of Clonostachys rogersoniana. J Nat Prod. 2018;82:462–8.
Ariefta NR, Kristiana P, Nurjanto HH, Momma H, Kwon E, Ashitani T, et al. Nectrianolins A, B, and C, new metabolites produced by endophytic fungus Nectria pseudotrichia 120-1NP. Tetrahedron Lett. 2017;58:4082–6.
Song H, Shen W, Dong J. Nematicidal metabolites from Gliocladium roseum YMF1. 00133. Appl Biochem Microbiol. 2016;52:324–30.
Yamada T, Yoshida K, Kikuchi T, Hirano T. Isolation and structure elucidation of new cytotoxic macrolides halosmysins b and c from the fungus Halosphaeriaceae sp. associated with a marine alga. Mar Drugs. 2022;20:226.
Knowles SL, Roberts CD, Augustinovic M, Flores-Bocanegra L, Raja HA, Heath-Borrero KN, et al. Opportunities and limitations for assigning relative configurations of antibacterial bislactones using GIAO NMR shift calculations. J Nat Prod. 2021;84:1254–60.
Koch K, Podlech J, Pfeiffer E, Metzler M. Total synthesis of alternariol. J Org Chem. 2005;70:3275–6.
Chapla VM, Zeraik ML, Ximenes VF, Zanardi LM, Lopes MN, Cavalheiro AJ, et al. Bioactive secondary metabolites from Phomopsis sp., an endophytic fungus from Senna spectabilis. Molecules. 2014;19:6597–608.
Li R, Su Z, Sun C, Wu S. Antibacterial insights into alternariol and its derivative alternariol monomethyl ether produced by a marine fungus. Appl Environ Microbiol. 2024;90:e00058–24.
Schreck I, Deigendesch U, Burkhardt B, Marko D, Weiss C. The Alternaria mycotoxins alternariol and alternariol methyl ether induce cytochrome P4501A1 and apoptosis in murine hepatoma cells dependent on the aryl hydrocarbonreceptor. Arch Toxicol. 2012;86:625–32.
Bensassi F, Gallerne C, Sharaf El Dein O, Hajlaoui MR, Bacha H, Lemaire C. Cell death induced by the Alternaria mycotoxin Alternariol. Toxicol Vitr. 2012;26:915–23.
Zhang N, Zhang C, Xiao X, Zhang Q, Huang B. New cytotoxic compounds of endophytic fungus Alternaria sp. isolated from Broussonetia papyrifera (L.) Vent. Fitoterpia. 2016;110:173–80.
Zaidan M, Noor Rain A, Badrul A, Adlin A, Norazah A, Zakiah I. In vitro screening of five local medicinal plants for antibacterial activity using disc diffusion method. Trop Biomed. 2005;22:165–70.
Woo EE, Ha LS, Kim JY, Lee IK, Yun BS. Rhizophins A and B, new sesquiterpenes from the culture broth of Coprinus rhizophorus. J Antibiot. 2020;73:175–8.
Lim HJ, Bae J, Bak SG, Chandimali N, Park EH, Park SI, et al. Limocitrin suppresses breast cancer through inducing apoptotic-cell death signaling and inhibiting the PI3K/AKT/mTOR/S6K cell survival signaling. J Med Food. 2023;26:749–59.
Ki DW, Choi DC, Won YS, Lee SJ, Kim YH, Lee IK, et al. Three new phthalide derivatives from culture broth of Dentipellis fragilis and their cytotoxic activities. J Antibiot. 2024;77:338–44.
Kim YH, Choi DC, Ki DW, Won YS, Lee SJ, Kim JY, et al. Three new nonenes from culture broth of marine-derived fungus Albifimbria verrucaria and their cytotoxic and anti-viral activities. J Antibiot. 2024;77:466–70.
Acknowledgements
This research was supported by the Research Base Construction Fund Support Program funded by Jeonbuk National University in 2025. The authors thank Ms. Ji-Young Oh (Center for University-wide Research Facilities (CURF) at Jeonbuk National University) for performing NMR measurements.
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Choi, DC., Ki, DW., Kim, Y.H. et al. New dimeric 5-hydroxy-2-hexenoic acid isolated from culture broth of Clonostachys rogersoniana. J Antibiot 78, 380–383 (2025). https://doi.org/10.1038/s41429-025-00824-9
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DOI: https://doi.org/10.1038/s41429-025-00824-9