石花菜共附生烟曲霉Aspergillus fumigatus 9-1次级代谢产物抗菌、抗氧化研究

doi:10.11978/2024182

Abstract

Abstract:

This paper examines the structure and activity of the secondary metabolites of Aspergillus fumigatus 9-1, a symbiotic epiphytic fungus of rockweed. The secondary metabolites produced by A. fumigatus 9-1 were systematically separated and purified using a combination of thin layer chromatography, silica gel column chromatography, high performance liquid chromatography, and gel column chromatography, resulting in the isolation of 16 compounds. Spectral analysis, including nuclear magnetic resonance (NMR) spectroscopy and comparison with literature data, led to the structural elucidation of these compounds as: prenylcyclotryprostatin A (1), verruculogen TR-2 (2), cyclotryprostatin E (3), cyclotryprostatin B (4), asperfumigatin (5), 12R, 13S-dihydroxyfumitremorgin C (6), spirocyclic diketopiperazine alkaloid (7), fumigaclavine C (8), fumigaclavine A (9), chaetominine (10), fumiquinazoline J (11), thymidine (12), pyripyropene A (13), monomethylsulochrin (14), questin (15), and helvolic acid (16). Compound 1 was first reported from Aspergillus. The antimicrobial activity showed that compound 16 had strong antibacterial activity against Listeria monocytogenes, with a minimum inhibitory concentration of 4.03 μg·mL^-1. 13-15 had moderate antibacterial activity against L. monocytogenes, with MICs of 66.25, 78.63 and 64.54 μg·mL⁻¹, respectively. The in vitro antioxidant activity results demonstrated that compound 6 exhibited robust DPPH (1, 1-diphenyl-2-picryl-hydrazyl radical) radical scavenging activity, with a half inhibitory concentration of 9.82μg·mL^-1. Additionally, compounds 6, 8, 9, 14 displayed notable ABTS (2, 2'-azinobis-(3-ethylbenzthiazoline-6-sulphonate)) radical scavenging activity, with a half inhibitory concentration of 2.72, 0.43, 3.23 and 1.96 μg·mL^-1, respectively.

Key words: Aspergillus fumigatus, secondary metabolites, antibacterial activity, antioxidant activity

CLC Number:

Q936

HE Mingfeng, HUANG Jiaxiang, TIAN Yongqi. Research on the antioxidant and antibacterial activities of secondary metabolites from Gelidium-derived fungus Aspergillus fumigatus 9-1[J].Journal of Tropical Oceanography, 2025, 44(3): 157-166.

Figures/Tables 2

References 29

[1]	丛梦静, 胡怡伟, 赵凯, 等, 2022. 深海冷泉来源真菌Talaromyces helicus SCSIO41311中聚酮类化学成分研究[J]. 热带海洋学报, 41(5): 117-120. doi: 10.11978/2021168
	CONG MENGJING, HU YIWEI, ZHAO KAI, et al, 2022. Study on the polyketides from a cold-seep-derived Talaromyces helicus SCSIO41311[J]. Journal of Tropical Oceanography, 41(5): 117-120 (in Chinese with English abstract).
[2]	冯婷, 孙建, 王玉妃, 等, 2024. 北部湾海洋真菌Aspergillus fumigatus DL-p0m-g2的化学成分及药理活性研究[J]. 热带海洋学报, 43(1): 154-166.
	FENG TING, SUN JIAN, WANG YUFEI, et al, 2024. Study on the chemical constituents and pharmacological activity of the marine-derived fungus Aspergillus fumigatus DL-p0m-g2 in the Beibu Gulf[J]. Journal of Tropical Oceanography, 43(1): 154-166 (in Chinese with English abstract).
[3]	孔维琦, 金鑫, 刘永宏, 等, 2025. 羊栖菜共附生真菌Aspergillus sp. GXIMD 02045的次级代谢产物研究[J]. 热带海洋学报, 44(1): 154-161.
	KONG WIQI, JIN XIN, LIU ZHIHONG, et al, 2025. Studies on secondary metabolites of Sargassum fusiforme derived fungus Aspergillus sp. GXIMD 02045[J]. Journal of Tropical Oceanography, 44(1): 154-161 (in Chinese with English abstract).
[4]	王小敏, 张民, 杨钰昆, 2015. 老蒜提取物萃取部位的抑菌活性及成分分析[J]. 现代食品科技, 31(1): 65-70.
	WANG XIAOMIN, ZHANG MIN, YANG YUKUN, 2015. Antimicrobial activities and component analysis of solvent extracts from aged garlic extract[J]. Modern Food Science and Technology, 31(1): 65-70 (in Chinese with English abstract).
[5]	姚佳晓, 贺小平, 周培娟, 等, 2019. 株海南三亚红树林真菌Alternaria alternate次级代谢产物的研究[J]. 中国海洋药物, 38(3): 64-70.
	YAO JIAXIAO, HE XIAOPING, ZHOU PEIJUAN, et al, 2019. Secondary metabolites from a mangrove fungus Alternaria alternate collected from Sanya, Hainan[J]. Chinese Journal of Marine Drugs, 38(3): 64-70 (in Chinese with English abstract).
[6]	杨曦亮, 王健娇, 姜睿, 等, 2020. 海藻共附生真菌活性天然产物研究进展[J]. 广西科学, 27(5): 462-474.
	YANG XILIANG, WANG JIANJIAO, JIANG RUI, et al, 2020. Advances in active natural products from marine Alga-derived fungi[J]. Guangxi Sciences, 27(5): 462-474 (in Chinese with English abstract).
[7]	张英格, 伍冠一, 陈曦, 2021. 石花菜化学成分与药理作用研究进展[J]. 海洋科学, 45(1): 129-138.
	ZHANG YINGGE, WU GUANYI, CHEN XI, 2021. Chemical constituents and pharmacological effects of Gelidium amansii[J]. Marine Sciences, 45(1): 129-138 (in Chinese with English abstract).
[8]	CHEN FUAN, WU ANBANG, SHIEH P, et al, 2006. Evaluation of the antioxidant activity of Ruellia tuberosa[J]. Food Chemistry, 94(1): 14-18.
[9]	CUI CHENGBIN, KAKEYA H, OSADA H, 1997. Novel mammalian cell cycle inhibitors, cyclotroprostatins A-D, produced by Aspergillus fumigatus, which inhibit mammalian cell cycle at G2/M phase[J]. Tetrahedron, 53(1): 59-72.
[10]	GUO NA, BAI XUE, SHEN YONG, et al, 2023. Target-based screening for natural products against Staphylococcus aureus biofilms[J]. Critical Reviews in Food Science and Nutrition, 63(14): 2216-2230.
[11]	HANNODA H M, BADR J M, YOUSEF D, et al, 2007. Three antioxidant compounds of the red alga Liagora farinosa[J]. Natural Product Sciences, 13(2): 140-143.
[12]	HE FEI, SUN YULIN, LIU KAISHENG, et al, 2012. Indole alkaloids from marine-derived fungus Aspergillus sydowii SCSIO 00305[J]. Journal of Antibiotics, 65(2): 109-111.
[13]	JIAO RUIHUA, XU SHU, LIU JUNYAN, et al, 2006. Chaetominine, a cytotoxic alkaloid produced by endophytic Chaetomium sp. IFB-E015[J]. Organic Letters, 8(25): 5709-5712.
[14]	KONG Fandong, HUANG Xiaolong, MA Qingyun, et al, 2018. Helvolic acid derivatives with antibacterial activities against Streptococcus agalactiae from the marine-derived fungus Aspergillus fumigatus HNMF0047[J]. Journal of Natural Products, 81(8): 1869-1876. doi: 10.1021/acs.jnatprod.8b00382 pmid: 30070829
[15]	LI XIAODONG, MIAO FENGPING, LIANG XIAORUI, et al, 2014a. Meroterpenes from an algicolous strain of Penicillium echinulatum[J]. Magnetic Resonance in Chemistry, 52(5): 247-250.
[16]	LI XIN, LI XIAOMING, XU GANGMING, et al, 2014b. Antioxidant metabolites from marine Alga-derived fungus Aspergillus wentii EN-48[J]. Phytochemistry Letters, 7: 120-123.
[17]	LIU BING, CHEN NING, CHEN YINGXIANG, et al, 2021. A new benzophenone with biological activities purified from Aspergillus fumigatus SWZ01[J]. Natural Product Research, 35(24): 5710-5719.
[18]	LIU RUI, ZHU WEIMING, ZHANG YAPENG, et al, 2006. A new diphenyl ether from marine-derived fungus Aspergillus sp. B-F-2[J]. Journal of Antibiotics, 59(6): 362-365.
[19]	RE R, PELLEGRINI N, PROTEGGENTE A, et al, 1999. Antioxidant activity applying an improved ABTS radical cation decolorization assay[J]. Free Radical Biology & Medicine, 26(9/10): 1231-1237.
[20]	SAWADSITANG S, MONGKOLTHANARUK W, SUWANNASAI N, et al, 2015. Antimalarial and cytotoxic constituents of Xylaria cf. cubensis PK108[J]. Natural Product Research, 29(21): 2033-2036.
[21]	SUN JIANHUI, YANG ZHONGDUO, ZHANG YIFEI, 2019. Chemical constituents and bioactivity of a fungal endophyte from Lamium amplexicaule[J]. Chemistry of Natural Compounds, 55(4): 775-778.
[22]	WU RIBANG, WU CUILING, LIU DAN, et al, 2018. Antioxidant and anti-freezing peptides from salmon collagen hydrolysate prepared by bacterial extracellular protease[J]. Food Chemistry, 248: 346-352. doi: S0308-8146(17)31984-2 pmid: 29329864
[23]	XIE FEI, LI XIAOBIN, ZHOU JINCHUAN, et al, 2015. Secondary metabolites from Aspergillus fumigatus, an endophytic fungus from the liverwort Heteroscyphus tener (Steph.) Schiffn[J]. Chemistry & Biodiversity, 12(9): 1313-1321.
[24]	ZHANG D, NOVIENDRI D, NURSID M, et al, 2007. 12, 13-dihydroxyfumitremorgin C, fumitremorgin C, and brevianamide F, antibacterial diketopiperazine alkaloids from the marine-derived fungus Pseudallescheria sp.[J]. Natural Product Sciences, 13: 251-254.
[25]	ZHANG WENFANG, LI JINYUAN, WEI CHENGWEN, et al, 2021. Chemical epigenetic modifiers enhance the production of immunosuppressants from the endophytic fungus Aspergillus fumigatus isolated from Cynodon dactylon[J]. Natural Product Research, 36(17): 4481-4485.
[26]	ZHANG YAHUI, GENG CE, ZHANG XINGWANG, et al, 2019. Discovery of bioactive indole-diketopiperazines from the marine-derived fungus Penicillium brasilianum aided by genomic information[J]. Marine Drugs, 17(9): 514.
[27]	ZHAO DAN, CAO FEI, GUO XIUJIE, et al, 2018. Antibacterial indole alkaloids and anthraquinones from a sewage-derived fungus Eurotium sp.[J]. Chemistry of Natural Compounds, 54(2): 399-401.
[28]	ZHOU PENG, YAN SHAN, LU YUANYUAN, et al, 2021. Five new secondary metabolites from the fungus Phomopsis asparagi[J]. Fitoterapia, 150: 104840.
[29]	ZOU RENJIAN, WEI CHENGWEN, ZHANG XUEXIA, et al, 2021. Alkaloids from endophytic fungus Aspergillus fumigatus HQD24 isolated from the Chinese mangrove plant Rhizophora mucronata[J]. Natural Product Research, 36(19): 5069-5073.

Research on the antioxidant and antibacterial activities of secondary metabolites from Gelidium-derived fungus Aspergillus fumigatus 9-1

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