Structural characterization, derivatization and antibacterial activity of secondary metabolites produced by termite‐associated Streptomyces showdoensisBYF17

Abstract

BACKGROUND Insect‐associated Streptomyces is a valuable resource for development of compounds with antibacterial potential. However, relatively little is known of the secondary metabolites produced by termite‐associated Streptomyces. RESULTS Here, seven compounds including o‐acetaminophenol (1), phenazine‐1,6‐dicarboxylic acid (2), phenylacetic acid (3), phenazinolin D (4), izumiphenazine A (5), izumiphenazine B (6) and phenazinolin E (7) were obtained from the fermentation broth of a termite‐associated Streptomyces showdoensis BYF17, which was isolated from the body surfaces of Odontotermes formosanus. Two additional novel derivative compounds (6a and 6b) were synthesized via acetylation and methylation, respectively. The structures of these compounds were elucidated by spectroscopic analyses. The antibacterial bioassay showed that compound 6a displayed strong inhibitory effects against Pseudomonas syringae pv. actinidiae (Psa), with a zone of inhibition (ZOI) diameter of 20.6 mm, which was comparable to that of positive gentamicin sulfate with a ZOI value of 25.6 mm. Furthermore, the Day 5 curative activities of both compounds 6 and 6a against kiwifruit bacterial canker were 71.5%, which was higher than those of referred oxine‐copper (55.0%) and ethylicin (46.8%) at a concentration of 200 μg mL−1. In addition, the mechanism analysis based on scanning electron microscopic observation revealed that both compounds 6 and 6a destroyed the integrity of the Psa cell membrane. CONCLUSION The results of biological tests showed that these bioactive compounds exhibit potent antimicrobial activities, which have the potential to be developed into new antibacterial agents. © 2023 Society of Chemical Industry.

Present Status, Limitations, and Prospects of Using Streptomyces Bacteria as a Potential Probiotic Agent in Aquaculture

“…Actinidiae , Escherichia coli , Staphylococcus aureus , and Micrococcus tetragenus with zones of inhibition 20.6, 12.9, 12.6, and 13.3 mm, respectively. Phenazinolin D, izumiphenazine A, and E showed antagonistic activity against Staphylococcus aureus and Micrococcus tetragenus with the zone of inhibition values of 10.3, 10.6, and 11.7 mm and 15.9 and 11.2 mm, respectively [ 95 ]. Streptomyces strains in aquaculture may benefit from the ability to produce antagonistic compounds to compete for nutrients, space, and binding sites in the host (see Fig.…”

Pitsubcosides A–L, highly esterified eudesmane sesquiterpenoid glycosides with antibacterial activity from Pittosporum subulisepalum and their mechanism

“…Pseudomonas syringae pv. actinidiae ( Psa ) is one of the most harmful kiwifruit pathogens, causing bacterial canker disease and destroying kiwifruit and other fruit production 2 …”

“…actinidiae (Psa) is one of the most harmful kiwifruit pathogens, causing bacterial canker disease and destroying kiwifruit and other fruit production. 2 Although use of traditional bactericides can be an effective strategy to control plant bacterial diseases, bactericide resistance has gradually become a serious problem because of the single and long-term usage of traditional bactericides. 3 Therefore, there is an urgent need to discover high-efficiency, low-toxicity and low resistance antibacterial agents with a characteristic mode of action.…”

“…13 C NMR spectroscopic data of compounds 1-12 in CDCl 3 (⊐ C in ppm, type) CH 2 41.0, CH2 45.2, CH 2 41.2, CH 2 41.1, CH 2 41.1, CH 2 41.1, CH 2 41.7, CH 213.3, C 81.0, CH 2 31.6, CH 2 31.5, CH 2 23.7, CH 2 20.4, CH 2 22.5, CH 2 20.2, CH 2 20.3, CH 2 20.1, CH 2 20.1, CH 2 18.3, CH 41.3, CH 2 26.9, CH 2 3 34.4, CH 2 34.6, CH 2 37.1, CH 2 42.9, CH 2 37.2, CH 2 42.9, CH 2 43.3, CH 2 42.7, CH 2 42.7, CH 2 41.5, CH 31.5, CH 2 32.6, CH 2 CH 51.0, CH 54.9, CH 55.0, CH 54.6, CH 54.7, CH 51.7, CH 57.9, CH 46.2, CH 6 22.2, CH 2 29.9, CH 2 25.0, CH 2 20.9, CH 2 20.0, CH 2 21.2, CH 2 21.3, CH 2 21.0, CH 2 21.0, CH 2 20.9, CH 20.6, CH 2 20.7, CH 2 CH 49.1, CH 48.8, CH 49.1, CH 49.0, CH 48.9, CH 48.9, CH 42.2, CH 41.6, CH 8 24.1, CH 2 23.3, CH 2 22.6, CH 2 23.4, CH 2 21.7, CH 2 22.5, CH 2 22.9, CH 2 22.4, CH 2 22.4, CH 2 22.5, CH 26.0, CH 2 20.8, CH 2 9 37.2, CH 2 33.7, CH 2 41.4, CH 2 44.7, CH 2 41.1, CH 2 44.8, CH 2 44.8, CH 2 44.7, CH 2 44.7, CH 2 44.0, CH 38.6, CH 2 37.1, CH 2 CH 3 25.0, CH 3 23.6, CH 3 21.3, CH 3 23.8, CH 3 22.9, CH 3 22.6, CH 3 22.7, CH 3 22.8, CH 3 22.5, CH 22.5, CH 3 25.1, CH 3 13 25.2, CH 3 26.4, CH 3 25.0, CH 3 25.8, CH 3 24.8, CH 3 25.2, CH 3 25.6, CH 3 25.2, CH 3 25.1, CH 3 25.2, CH 25.3, CH 3 25.5, CH 3 14 10.4, CH 3 11.6, CH 3 16.6, CH 3 19.1, CH 3 19.5, CH 3 18.9, CH 3 18.9, CH 3 18.8, CH 3 18.8, CH 3 18.8, CH 12.0, CH 3 14.8, CH 3 15 107.1, CH 2 106.8, CH 2 105.5, CH 2 23.2, CH 3 19.9, CH 3 23.0, CH 3 22.6, CH 3 22.9, CH 3 22.9, CH 3 30.4, CH 14.5, CH 3 23.5, CH 3 00 21.1, CH 3 21.1, CH 3 115.7, CH 116.2, CH 115.8, CH 21.3, CH 3 21.1, CH 3 21.0, CH 3 21.1, CH 3 21.1, CH 21.0, CH 3 21.1, CH 3 00 115.5, CH 115.5, CH 20.6, CH 3 20.5, CH 3 20.6, CH 3 115.6, CH 115.8, CH 127.3, C 115.5, CH 115.5, CH 115.4, CH 115.5, CH…”

Enhanced Biosynthesis of Phenazine-1,6-dicarboxylic Acid in Streptomyces coelicolor

“…In addition, it should be noted that PDC derivatives (Figure 1) including lomofungin, 17 myxin, 18 esmeraldins, 14 izumiphenazines, 19 and D-alanylgriseoluteic acid 20,21 exhibit more complex structures and diverse bioactivities in contrast to PCA derivatives, which further highlights the importance of selectively biosynthesizing PDC. One interesting phenomenon is that most Pseudomonas strains only produce PCA, whereas most Streptomyces strains have been reported as PDC derivatives producers, 22,23 which inspires us to search potential BGCs or strains for PDC production in the Streptomyces genus. Biorefinery and biomanufacturing processes for producing value-added biofuel, 24 biobased materials, 25 and chemicals 26 are widely investigated with the development of metabolic engineering.…”