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Volume 16 Issue 2
Apr.  2025
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REN Qinqin, CHEN Shaowei, ZHENG Jiahua, WANG Rui, XU Liangxiong, TAO Jun. Methylcyclohexanone metabolites from endophytic Aspergillus sp. HU0206 have inhibitory activity against Xanthomonas oryzae pv. oryzae[J]. Journal of Tropical Biology, 2025, 16(2): 254-259. doi: 10.15886/j.cnki.rdswxb.20240010
Citation: REN Qinqin, CHEN Shaowei, ZHENG Jiahua, WANG Rui, XU Liangxiong, TAO Jun. Methylcyclohexanone metabolites from endophytic Aspergillus sp. HU0206 have inhibitory activity against Xanthomonas oryzae pv. oryzae[J]. Journal of Tropical Biology, 2025, 16(2): 254-259. doi: 10.15886/j.cnki.rdswxb.20240010

Methylcyclohexanone metabolites from endophytic Aspergillus sp. HU0206 have inhibitory activity against Xanthomonas oryzae pv. oryzae

doi: 10.15886/j.cnki.rdswxb.20240010
  • Received Date: 2024-01-18
  • Rev Recd Date: 2024-05-18
  • During the continuing investigation of the antibacterial metabolites from endophytic Aspergillus sp. HU0206,six compounds were isolated from the fermented culture of this fungus by column chromatography and high-performance liquid preparation. These compounds were elucidated as four methylcyclohexanones: ampelomin A( 1 ), 7-hydroxylampelomin A( 2 ), 7-O-ethylampelomin A( 3 ), 2,3-dihydroxyl-7-O-ethylampelomin A( 4 ) and two methylphenols:2-(methoxymethyl)-1,4-benzenediol( 5 ) and 3-chlorogentisyl alcohol( 6 ) on the basis of NMR and ESI-MS analyses.Compounds 2-4 are new compounds. At the dose of 40 μg, compounds 1, 2 and 6 showed obvious antibacterial effects on Xanthomonas oryzae with inhibition zones of 4.0 mm. Compound 6 also exhibited inhibitory activities against Staphylococcus aureus, methicillin-resistant S. aureus, Pectobacterium atroseptica and Ralstonia solanacearum. However,compounds 3-5 showed no inhibitory activity against X. oryzae and compounds 1-5 were inactive against the other four strains mentioned above. The biosynthesis pathway of the metabolites from Aspergillus sp. HU0206 was also discussed.
  • [1] NIÑO-LIU D O, RONALD P C, BOGDANOVE A J. Xanthomonas oryzae pathovars:model pathogens of a model crop[J]. Molecular Plant Pathology, 2006, 7(5):303-324.
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    [3] ZHAO S, WANG B, TIAN K, et al. Novel metabolites from the Cercis chinensis derived endophytic fungus Alternaria alternata ZHJG5 and their antibacterial activities[J]. Pest Management Science, 2021, 77(5):2264-2271.
    [4] YANG J, GONG L, GUO M, et al. Bioactive indole diketopiperazine alkaloids from the marine endophytic fungus Aspergillus sp. YJ191021[J]. Marine Drugs, 2021, 19(3):157.
    [5] 王瑞,陈少微,于燕燕,等.老鼠艻内生曲霉HU0206的抗细菌活性代谢成分[J]. 热带亚热带植物学报, 2023,31(5):736-740.
    [6] PONGTHARANGKUL T, DEMIRCI A. Evaluation of agar diffusion bioassay for nisin quantification[J]. Applied Microbiology and Biotechnology, 2004, 65(3):268-272.
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    [8] ZHANG H, XUE J, WU P, et al. Polyoxygenated methyl cyclohexanoids from a terrestrial ampelomyces fungus[J]. Journal of Natural Products, 2009, 72(2):265-269.
    [9] TORIBIO G, MARJANET G, ALIBÉS R, et al. Divergent approach to gabosines and anhydrogabosines:enantioselective syntheses of(+)-epiepoformin,(+)-EpoKformin,(+)-gabosine A, and gabosines B and F[J]. European Journal of Organic Chemistry, 2011, 2011(8):1534-1543.
    [10] YUAN P, LIU X, YANG X, et al. Total syntheses of(+)-gabosine P,(+)-gabosine Q,(+)-gabosine E,(-)-gabosine G,(-)-gabosine I,(-)-gabosine K,(+)-streptol, and(-)-uvamalol A by a diversity-oriented approach featuring tunable deprotection manipulation[J]. The Journal of Organic Chemistry, 2017, 82(7):3692-3701.
    [11] CHEN L, FANG Y, ZHU T, et al. Gentisyl alcohol derivatives from the marine-derived fungus Penicillium terrestre[J]. Journal of Natural Products, 2008, 71(1):66-70.
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Methylcyclohexanone metabolites from endophytic Aspergillus sp. HU0206 have inhibitory activity against Xanthomonas oryzae pv. oryzae

doi: 10.15886/j.cnki.rdswxb.20240010

Abstract: During the continuing investigation of the antibacterial metabolites from endophytic Aspergillus sp. HU0206,six compounds were isolated from the fermented culture of this fungus by column chromatography and high-performance liquid preparation. These compounds were elucidated as four methylcyclohexanones: ampelomin A( 1 ), 7-hydroxylampelomin A( 2 ), 7-O-ethylampelomin A( 3 ), 2,3-dihydroxyl-7-O-ethylampelomin A( 4 ) and two methylphenols:2-(methoxymethyl)-1,4-benzenediol( 5 ) and 3-chlorogentisyl alcohol( 6 ) on the basis of NMR and ESI-MS analyses.Compounds 2-4 are new compounds. At the dose of 40 μg, compounds 1, 2 and 6 showed obvious antibacterial effects on Xanthomonas oryzae with inhibition zones of 4.0 mm. Compound 6 also exhibited inhibitory activities against Staphylococcus aureus, methicillin-resistant S. aureus, Pectobacterium atroseptica and Ralstonia solanacearum. However,compounds 3-5 showed no inhibitory activity against X. oryzae and compounds 1-5 were inactive against the other four strains mentioned above. The biosynthesis pathway of the metabolites from Aspergillus sp. HU0206 was also discussed.

REN Qinqin, CHEN Shaowei, ZHENG Jiahua, WANG Rui, XU Liangxiong, TAO Jun. Methylcyclohexanone metabolites from endophytic Aspergillus sp. HU0206 have inhibitory activity against Xanthomonas oryzae pv. oryzae[J]. Journal of Tropical Biology, 2025, 16(2): 254-259. doi: 10.15886/j.cnki.rdswxb.20240010
Citation: REN Qinqin, CHEN Shaowei, ZHENG Jiahua, WANG Rui, XU Liangxiong, TAO Jun. Methylcyclohexanone metabolites from endophytic Aspergillus sp. HU0206 have inhibitory activity against Xanthomonas oryzae pv. oryzae[J]. Journal of Tropical Biology, 2025, 16(2): 254-259. doi: 10.15886/j.cnki.rdswxb.20240010
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