Structural characterization, derivatization, and bioactivities of secondary metabolites produced by termite-associated Streptomyces lannensis BYF-106
ABSTRACT Two new C-glycoside angucycline-related analogs, urdamycin Y (1) and grincamycin W (2), as well as eight known metabolites (3–10), were identified from termite-associated Streptomyces lannensis BYF-106 based on global natural products social molecular networking (GNPS). The putative biosynt...
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American Society for Microbiology
2025-05-01
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| Series: | Microbiology Spectrum |
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| Online Access: | https://journals.asm.org/doi/10.1128/spectrum.01818-24 |
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| author | Jun Wu Miao Zhang Jian Tao MengRu Liu JianHao Xiong TaoShan Jiang YaXuan Wang XiaoHong Li YueYue Li CaiPing Yin ShuXiang Zhang XinHua Liu YingLao Zhang |
| author_facet | Jun Wu Miao Zhang Jian Tao MengRu Liu JianHao Xiong TaoShan Jiang YaXuan Wang XiaoHong Li YueYue Li CaiPing Yin ShuXiang Zhang XinHua Liu YingLao Zhang |
| author_sort | Jun Wu |
| collection | DOAJ |
| description | ABSTRACT Two new C-glycoside angucycline-related analogs, urdamycin Y (1) and grincamycin W (2), as well as eight known metabolites (3–10), were identified from termite-associated Streptomyces lannensis BYF-106 based on global natural products social molecular networking (GNPS). The putative biosynthetic pathways of urdamycin Y (1) and grincamycin W (2) were proposed using bioinformatic analysis of the full genome of S. lannensis BYF-106. In addition, four new derivative compounds (4A, 5A, 6A, and 6B) were synthesized via acetylation and methylation, respectively. Partial compounds were evaluated in vitro for antibacterial, anti-inflammatory, and cytotoxic activities. Vineomycinone B2 (3), fridamycin D (4), and 6-hydroxytetrangulol (5) displayed broad-spectrum antibacterial activities against S. aureus, methicillin-resistant S. aureus, and P. syringae pv. actinidae. Furthermore, urdamycin Y (1) exhibited potent inhibition on NO production, with an IC50 value of 4.8 µM, which was comparable to that of Bay11-7082 with an IC50 value of 2.1 µM. Subsequently, the possible anti-inflammatory mechanism of urdamycin Y (1) was explored by molecular docking simulation. Finally, most of the tested metabolites showed significant cytotoxic activities against HCT-116, HT-29, and A375. Notably, 6-hydroxytetrangulol (5) and the acetyl derivative 5A showed extremely strong cytotoxic activities against HCT-116, with IC50 values of 9.8 and 2.2 µM, respectively. Moreover, 5A showed extremely strong cytotoxic activity against A375 (IC50 <0.2 µM), and the conceivable cytotoxic activity mechanism was also proposed by molecular docking. These findings indicated metabolites of insect-associated S. lannensis BYF-106 might be a potential source for developing new bioactive drugs in food, agriculture, and biomedical fields.IMPORTANCEFrequent attention to soil microorganisms has led to the rediscovery of known compounds. By contrast, insect-associated Streptomyces have been shown to produce a more diverse array of unique bioactive secondary metabolites compared to soil Streptomyces. In our ongoing effort to explore structurally diverse bioactive natural products from termite-associated Streptomyces, we discovered that the strain S. lannensis BYF-106 exhibited potent bioactivity. Chemical investigation of BYF-106 resulted in the isolation of two new C-glycoside angucycline-related analogs: urdamycin Y (1) and grincamycin W (2). In addition, four new derivative compounds (4A, 5A, 6A, and 6B) were synthesized through acetylation and methylation, respectively. Urdamycin Y (1) exhibited a strong inhibitory effect on NO production, and most of the tested metabolites showed significant cytotoxic activity. These findings indicate that the metabolites of BYF-106 may offer promising avenues for the exploration and development of new bioactive drugs. |
| format | Article |
| id | doaj-art-241cbf95ae6b4463ab79dba3d447f9e7 |
| institution | Kabale University |
| issn | 2165-0497 |
| language | English |
| publishDate | 2025-05-01 |
| publisher | American Society for Microbiology |
| record_format | Article |
| series | Microbiology Spectrum |
| spelling | doaj-art-241cbf95ae6b4463ab79dba3d447f9e72025-08-20T03:52:14ZengAmerican Society for MicrobiologyMicrobiology Spectrum2165-04972025-05-0113510.1128/spectrum.01818-24Structural characterization, derivatization, and bioactivities of secondary metabolites produced by termite-associated Streptomyces lannensis BYF-106Jun Wu0Miao Zhang1Jian Tao2MengRu Liu3JianHao Xiong4TaoShan Jiang5YaXuan Wang6XiaoHong Li7YueYue Li8CaiPing Yin9ShuXiang Zhang10XinHua Liu11YingLao Zhang12School of Life Science, Anhui Agricultural University, Hefei, ChinaSchool of Life Science, Anhui Agricultural University, Hefei, ChinaSchool of Life Science, Anhui Agricultural University, Hefei, ChinaSchool of Life Science, Anhui Agricultural University, Hefei, ChinaSchool of Life Science, Anhui Agricultural University, Hefei, ChinaSchool of Life Science, Anhui Agricultural University, Hefei, ChinaSchool of Life Science, Anhui Agricultural University, Hefei, ChinaSchool of Life Science, Anhui Agricultural University, Hefei, ChinaSchool of Life Science, Anhui Agricultural University, Hefei, ChinaSchool of Life Science, Anhui Agricultural University, Hefei, ChinaSchool of Life Science, Anhui Agricultural University, Hefei, ChinaSchool of Pharmacy, Anhui Medical University, Hefei, ChinaSchool of Life Science, Anhui Agricultural University, Hefei, ChinaABSTRACT Two new C-glycoside angucycline-related analogs, urdamycin Y (1) and grincamycin W (2), as well as eight known metabolites (3–10), were identified from termite-associated Streptomyces lannensis BYF-106 based on global natural products social molecular networking (GNPS). The putative biosynthetic pathways of urdamycin Y (1) and grincamycin W (2) were proposed using bioinformatic analysis of the full genome of S. lannensis BYF-106. In addition, four new derivative compounds (4A, 5A, 6A, and 6B) were synthesized via acetylation and methylation, respectively. Partial compounds were evaluated in vitro for antibacterial, anti-inflammatory, and cytotoxic activities. Vineomycinone B2 (3), fridamycin D (4), and 6-hydroxytetrangulol (5) displayed broad-spectrum antibacterial activities against S. aureus, methicillin-resistant S. aureus, and P. syringae pv. actinidae. Furthermore, urdamycin Y (1) exhibited potent inhibition on NO production, with an IC50 value of 4.8 µM, which was comparable to that of Bay11-7082 with an IC50 value of 2.1 µM. Subsequently, the possible anti-inflammatory mechanism of urdamycin Y (1) was explored by molecular docking simulation. Finally, most of the tested metabolites showed significant cytotoxic activities against HCT-116, HT-29, and A375. Notably, 6-hydroxytetrangulol (5) and the acetyl derivative 5A showed extremely strong cytotoxic activities against HCT-116, with IC50 values of 9.8 and 2.2 µM, respectively. Moreover, 5A showed extremely strong cytotoxic activity against A375 (IC50 <0.2 µM), and the conceivable cytotoxic activity mechanism was also proposed by molecular docking. These findings indicated metabolites of insect-associated S. lannensis BYF-106 might be a potential source for developing new bioactive drugs in food, agriculture, and biomedical fields.IMPORTANCEFrequent attention to soil microorganisms has led to the rediscovery of known compounds. By contrast, insect-associated Streptomyces have been shown to produce a more diverse array of unique bioactive secondary metabolites compared to soil Streptomyces. In our ongoing effort to explore structurally diverse bioactive natural products from termite-associated Streptomyces, we discovered that the strain S. lannensis BYF-106 exhibited potent bioactivity. Chemical investigation of BYF-106 resulted in the isolation of two new C-glycoside angucycline-related analogs: urdamycin Y (1) and grincamycin W (2). In addition, four new derivative compounds (4A, 5A, 6A, and 6B) were synthesized through acetylation and methylation, respectively. Urdamycin Y (1) exhibited a strong inhibitory effect on NO production, and most of the tested metabolites showed significant cytotoxic activity. These findings indicate that the metabolites of BYF-106 may offer promising avenues for the exploration and development of new bioactive drugs.https://journals.asm.org/doi/10.1128/spectrum.01818-24Odontotermes formosanusStreptomyces lannensisnatural productsantibacterial activityanti-inflammatory activitycytotoxic activity |
| spellingShingle | Jun Wu Miao Zhang Jian Tao MengRu Liu JianHao Xiong TaoShan Jiang YaXuan Wang XiaoHong Li YueYue Li CaiPing Yin ShuXiang Zhang XinHua Liu YingLao Zhang Structural characterization, derivatization, and bioactivities of secondary metabolites produced by termite-associated Streptomyces lannensis BYF-106 Microbiology Spectrum Odontotermes formosanus Streptomyces lannensis natural products antibacterial activity anti-inflammatory activity cytotoxic activity |
| title | Structural characterization, derivatization, and bioactivities of secondary metabolites produced by termite-associated Streptomyces lannensis BYF-106 |
| title_full | Structural characterization, derivatization, and bioactivities of secondary metabolites produced by termite-associated Streptomyces lannensis BYF-106 |
| title_fullStr | Structural characterization, derivatization, and bioactivities of secondary metabolites produced by termite-associated Streptomyces lannensis BYF-106 |
| title_full_unstemmed | Structural characterization, derivatization, and bioactivities of secondary metabolites produced by termite-associated Streptomyces lannensis BYF-106 |
| title_short | Structural characterization, derivatization, and bioactivities of secondary metabolites produced by termite-associated Streptomyces lannensis BYF-106 |
| title_sort | structural characterization derivatization and bioactivities of secondary metabolites produced by termite associated streptomyces lannensis byf 106 |
| topic | Odontotermes formosanus Streptomyces lannensis natural products antibacterial activity anti-inflammatory activity cytotoxic activity |
| url | https://journals.asm.org/doi/10.1128/spectrum.01818-24 |
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