Secondary metabolites of fungus Fusarium sp. J3 and their bioactivity

doi:10.3969/j.issn.1000-1565.2026.04.008

Abstract

Abstract: In this study, the secondary metabolites of fungus Fusarium sp. J3 were isolated and identified to explore novel compounds that possess unique structures and biological activities. The ethyl acetate extract of the rice fermentation of the fungus was purified by separation technologies such as silica gel column chromatography, gel column chromatography and high-performance liquid chromatography(HPLC), and the chemical structures of these compounds were elucidated by NMR and ESI-MS. A total of 17 compounds were isolated, including 1 aromatic compound(14), 1 amide compound(15), 3 terpenoids(16, 22, 28), 3 cyclic peptides(17, 29, 30), 1 ketene compound(18), 5 esters(19, 20, 23, 24, 25), and 3 steroids(21, 26, 27). Among these compounds, 24 was isolated from genus Fusarium for the first time. The anti-inflammatory and anti-tumor activities of these compounds were evaluated. Compounds 17, 24 and 30 showed certain anti-inflammatory effect at a mass concentration of 10 μg/mL, with the inhibition rates against NO reaching about 45%. Compound 29 displayed significant inhibitory activity- 引用格式:冯忠居,于明威,张聪,等.冲刷场地地震波形对大直径变截面单桩时程响应的影响［J］.河北大学学报(自然科学版),2026,46(4):337-348.引用格式:苏亚宁,刘惠颖,唐宏亮,等.镰刀菌属真菌Fusarium sp.J3次级代谢产物及生物活性［J］.河北大学学报(自然科学版),2026,46(4):403-412.DOI:10.3969/j.issn.1000-1565.2026.04.008镰刀菌属真菌Fusarium sp.J3次级代谢产物及生物活性苏亚宁¹,刘惠颖¹,唐宏亮²,王润妍¹,赵晓珑¹,罗都强²(1.河北大学化学与材料科学学院,河北保定 071002;2.河北大学生命科学学院,河北保定 071002)摘要:以镰刀菌Fusarium sp.J3为研究对象,挖掘结构新颖且具有生物活性的次级代谢产物.对真菌Fusarium sp.J3进行大米发酵,通过硅胶柱层析、凝胶柱层析、高效液相色谱(HPLC)等分离技术分离发酵物的乙酸乙酯提取物,利用NMR、ESI-MS等波谱解析技术进行化合物结构鉴定.从目标菌株的乙酸乙酯提取物中共分离得到了17个化合物,包含1个芳香类化合物(14),1个酰胺类化合物(15),3个萜类化合物(16,22,28),3个环肽类化合物(17,29,30),1个烯酮类化合物(18),5个酯类化合物(19,20,23,24,25)和3个甾体类化合物(21,26,27);其中,化合物24系新化合物,且首次从镰刀菌属真菌中分离得到.对所得化合物进行了抗炎和抗肿瘤活性测定,结果表明:化合物17、24和30在质量浓度为10 μg/mL时,具有一定的抗炎活性,对NO抑制率达到45%以上;化合物29对肿瘤细胞MCF-7具有显著抑制活性,IC₅₀值为6.77 μg/mL.关键词:Fusarium sp.J3;次级代谢产物;抗炎;抗肿瘤中图分类号:Q936 文献标志码:A 文章编号:1000-1565(2026)04-0403-10DOI:10.3969/j.issn.1000-1565.2026.04.008Secondary metabolites of fungus Fusarium sp. J3 and their bioactivitySU Yaning¹, LIU Huiying¹, TANG Hongliang², WANG Runyan¹, ZHAO Xiaolong¹, LUO Duqiang²(1. College of Chemistry and Materials Science, Hebei University, Baoding 071002, China; 2. College of Life Sciences, Hebei University, Baoding 071002, China)Abstract: In this study, the secondary metabolites of fungus Fusarium sp. J3 were isolated and identified to explore novel compounds that possess unique structures and biological activities. The ethyl acetate extract of the rice fermentation of the fungus was purified by separation technologies such as silica gel column chromatography, gel column chromatography and high-performance liquid chromatography(HPLC), and the chemical structures of these compounds were elucidated by NMR and ESI-MS. A total of 17 compounds were isolated, including 1 aromatic compound(14), 1 amide compound(15), 3 terpenoids(16, 22, 28), 3 cyclic peptides(17, 29, 30), 1 ketene compound(18), 5 esters(19, 20, 23, 24, 25), and 3 steroids(21, 26, 27). Among these compounds, 24 was isolated from genus Fusarium for the first time. The anti-inflammatory and anti-tumor activities of these compounds were evaluated. Compounds 17, 24 and 30 showed certain anti-inflammatory effect at a mass concentration of 10 μg/mL, with the inhibition rates against NO reaching about 45%. Compound 29 displayed significant inhibitory activity- 收稿日期:2025-08-28;修回日期:2026-03-26 基金项目:河北省生物医药联合基金项目(B2020201090);省级大学生创新训练计划项目(DC2025311) 第一作者:苏亚宁(2002—),女,河北大学在读硕士研究生,主要从事天然药物化学研究.E-mail:3176926395@qq.com 通信作者:赵晓珑(1980—),女,河北大学副教授,博士,主要从事金属配合物抗癌作用和天然产物化学研究.E-mail: longlong_666@sina.com罗都强(1968—),男,河北大学教授,博士,主要从事天然产物化学研究.E-mail:duqiangluo999@126.com 第4期苏亚宁等:镰刀菌属真菌Fusarium sp.J3次级代谢产物及生物活性河北大学学报(自然科学版) 第46卷toward MCF-7 cells with IC₅₀ value of 6.77 μg/mL.

Key words: Fusarium sp. J3, secondary metabolite, anti-inflammatory, anti-tumor

CLC Number:

Q936

SU Yaning, LIU Huiying, TANG Hongliang, WANG Runyan, ZHAO Xiaolong, LUO Duqiang. Secondary metabolites of fungus Fusarium sp. J3 and their bioactivity[J]. Journal of Hebei University(Natural Science Edition), 2026, 46(4): 403-412.

References

[1] Chaturvedi V, Verma P. Microbial fuel cell:a green approach for the utilization of waste for the generation of bioelectricity [J]. Bioresour Bioprocess, 2016, 3:38-51. DOI:10.1186/s40643-016-0116-6.
[2] Kong C B, Pang Z Q, Zhang C F, et al. Effects of arbuscular mycorrhizal fungi on sugarcane growth and nutrient- related gene co-expression network under different fertilization levels[J]. Acta Agronom Sin, 2022, 48(4):860-872. DOI:10.3724/sp.j.1006.2022.14052.
[3] Habtewold J Z, Helgason B L, Yanni S F, et al. Litter composition has stronger influence on the structure of soil fungal than bacterial communities[J]. Eur J Soil Biol, 2020, 98:103190. DOI:10.1016/j.ejsobi.2020.103190.
[4] Banerjee S, Zhao C, Garland G, et al. Biotic homogenization, lower soil fungal diversity and fewer rare taxa in arable soils across Europe[J]. Nat Commun, 2024, 15:327. DOI:10.1038/s41467-023-44073-6.
[5] Bar-On Y M, Phillips R, Milo R. The biomass distribution on earth[J]. Proc Natl Acad Sci U S A, 2018, 115(25):6506-6511. DOI:10.1073/pnas.1711842115.
[6] Tiwari P, Srivastava Y, Bae H H. Trends of pharmaceutical design of endophytes as anti-infective[J]. Curr Top Med Chem, 2021, 21(17):1572-1586. DOI:10.2174/1568026621666210524093234.
[7] Zhang D Y, Li S J, Fan M H, et al. The novel compounds with biological activity derived from soil fungi in the past decade[J]. Drug Des Dev Ther, 2022, 16:3493-3555. DOI:10.2147/dDDT.s377921.
[8] Lu X, Feng W X, Kong M, et al. Isolation and identification of secondary metabolites from soil fungi Fusariums sp. CT01-P-5 in tea garden [J]. J Shenyang Pharma Univ, 2020, 37(1):1-6. DOI:10.14066/j.cnki.cn21-1349/r.2020.01.001.
[9] Shahniani A, Bamzadeh Z, Mahmoudnia F, et al. Evaluation of antibacterial and anticancer properties of secondary metabolites isolated from soil Bacillus spp. focusing on two strains of Bacillus licheniformis and Bacillus siamensis[J]. BMC Mol Cell Biol, 2024, 25:21. DOI:10.1186/s12860-024-00517-5.
[10] Konwar A N, Basak S, Saikia K, et al. Antimicrobial potential of Streptomyces sp. NP73 isolated from the forest soil of Northeast India against multi-drug resistant Escherichia coli[J]. Lett Appl Microbiol, 2024, 77(9):ovae086. DOI:10.1093/lambio/ovae086.
[11] Zheng S K, He L M, Wang C, et al. Studies on the secondary metabolites of the soil-derived peltate fungus Paraconiothyrium sp. ACC31771 [J]. Chin J Antibiot, 2025, 50(4):416-421. DOI:10.13461/j.cnki.cja.007892.
[12] Zhang Z, Miao S, Qi S Z, et al. Secondary metabolite and their activities of Penicillium terrigenum RD 4-3 isolated from saline-alkali soil in the Yellow River Delta [J]. J Shandong Univ(Health Sci), 2024, 62(3):28-38. DOI:10.6040/j.issn.1671-7554.0.2023.1125.
[13] Gill H, Sykes E M E, Kumar A, et al. Isolation of bioactive metabolites from soil derived fungus-aspergillus fumigatus[J]. Microorganisms, 2023, 11(3):590. DOI:10.3390/microorganisms11030590.
[14] Gubiani J R, Bernardi D I, De Paula C C P, et al. Absolute configuration of cytotoxic anthraquinones from a Brazilian cave soil-derived fungus, Aspergillus sp. SDC28[J]. Arch Der Pharm, 2022, 355(4):2100441. DOI:10.1002/ardp.202100441.
[15] Liu X J, Kong F D, Xiao N, et al. Prenylated indole-terpenoids with antidiabetic activities from Penicillium sp. HFF16 from the rhizosphere soil of Cynanchum bungei Decne[J]. Front Microbiol, 2023, 14:1099103. DOI:10.3389/fmicb.2023.1099103.
[16] Nguyen D H, Zhao B T, Le D D, et al. Phenolic constituents and their anti-inflammatory activity from Echinochloa utilis Grains[J]. Nat Prod Sci, 2016, 22(2):140-145. DOI:10.20307/nps.2016.22.2.140.
[17] Kaila N, Follows B, Leung L, et al. Discovery of isoquinolinone indole acetic acids as antagonists of chemoattractant receptor homologous molecule expressed on Th2 cells(CRTH2)for the treatment of allergic inflammatory diseases[J]. J Med Chem, 2014, 57(4):1299-1322. DOI:10.1021/jm401509e.
[18] Zhao Y W, Wei F, Zhi G Z, et al. Secondary metabolites from fungus NBERC_49006 with herbicidal activity [J]. Nat Prod Res. 2019, 31(10):1772-1776. DOI:10.16333/j.1001-6880.2019.10.015.
[19] Amagata T, Morinaka B I, Amagata A, et al. A chemical study of cyclic depsipeptides produced by a sponge-derived fungus[J]. J Nat Prod, 2006, 69(11):1560-1565. DOI:10.1021/np060178k.
[20] Ding L J, Gu B B, Jiao W H, et al. New furan and cyclopentenone derivatives from the sponge-associated fungus hypocrea koningii PF04[J]. Mar Drugs, 2015, 13(9):5579-5592. DOI:10.3390/md13095579.
[21] Hybelbauerová S, Sejbal J, Dracˇínsky M, et al. Chemical constituents of Stereum subtomentosum and two other birch-associated basidiomycetes:an interspecies comparative study[J]. Chem Biodivers, 2008, 5(5):743-750. DOI:10.1002/cbdv.200890070.
[22] Loukaci A, Kayser O, Bindseil K U, et al. New trichothecenes isolated from Holarrhena floribunda[J]. J Nat Prod, 2000, 63(1):52-56. DOI:10.1021/np990332l.
[23] Wang Y N, Tian L, Hua H M, et al. Two new compounds from the broth of the marine fungus Penicillium griseofulvum Y19-07[J]. J Asian Nat Prod Res, 2009, 11(11):912-917. DOI:10.1080/10286020903219923.
[24] Zhang S N, Cao S, Lin Y M, et al. Photocatalyzed site-selective C(sp 3)-H sulfonylation of toluene derivatives and cycloalkanes with inorganic sulfinates[J]. Chin J Catal, 2022, 43(3):564-570. DOI:10.1016/S1872-2067(21)63953-0.
[25] Nguyen A T, Malonne H, Duez P, et al. Cytotoxic constituents from Plumbago zeylanica[J]. Fitoterapia, 2004, 75(5):500-504. DOI:10.1016/j.fitote.2004.03.009.
[26] Zhou J, Li G, Deng Q, et al. Cytotoxic constituents from the mangrove endophytic Pestalotiopsis sp. induce G0/G1 cell cycle arrest and apoptosis in human cancer cells[J]. Nat Prod Res, 2018, 32(24):2968-2972. DOI:10.1080/14786419.2017.1395431.
[27] Shu JC, Liu M, Zhu GH, et. al. Two new compounds from Smilax glaucochin[J]. Chin J Chin Mater Med, 2018, 43(5):959-963. DOI:10.19540/j.cnki.cjcmm.20180104.016.
[28] TSUNOO A, KAMIJO M, TAKETOMO N, et al. Roseocardin, a novel cardiotonic cyclodepsipeptide from Trichothecium roseum TT103 [J]. J Antibiot(Tokyo), 1997, 50(12):1007-1013. DOI:10.1002/chin.199821196.
[29] Jegorov A, Havlícˇek V, Husˇák M, et al. Crystal structure of cyclo(2-hydroxy-i-valeryl-isoleucyl-2-hydroxy- i- valeryl-alanyl-threonyl)dihydrate, C₂₃H₃₉N₃O₈ · 2H₂O[J]. Z Für Kristallogr New Cryst Struct, 2005, 220(1/2/3/4):113-115. DOI:10.1524/ncrs.2005.220.14.113. (