Overexpression of hgc1 increases the production and diversity of hygrocins in Streptomyces sp. LZ35

Li, Shanren; Chen, Lu; Ou, Jinhuan; Deng, Jingjing; Shen, Yuemao

doi:10.1039/c5ra12623a

Cited by 19 publications

(20 citation statements)

References 11 publications

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“…The biosynthesis pathway of 8-deoxy-rifamycins demonstrated diverse cleavage patterns of ansa polyketide backbone, including 5,11 retro-Claisen cleavage, just like that observed in ansa biosynthesis of divergolides R and S [ 47 ], hygrocins I and J [ 48 ] and microansamycins G-I [ 49 ], which lead to protorifamycin I-M1 and proansamycin B-M1 ( 15 ) ( Figure 4 a), 12,19 double-bond cleavage and skeleton rearrangement lead to 8-deoxy-rifamycin B ( 18 ) ( Figure 4 b) and a novel 11,12-cleavage carried out by a typical Baeyer-Villiger oxidation and intramolecular transesterification formed 2 and 3 ( Figure 4 c) [ 41 ]. Compounds 5 , 6 , 7 , 8 , 9 , 10 and 11 oxygenated at C-20, C-23, C-30 and C-31 suggested that the ansa chain is prone to be oxidized in the ΔrifT strain during fermentation.…”

Section: Discussionmentioning

confidence: 99%

8-Deoxy-Rifamycin Derivatives from Amycolatopsis mediterranei S699 ΔrifT Strain

Shi

Zhao

et al. 2020

Biomolecules

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Proansamycin X, a hypothetical earliest macrocyclic precursor in the biosynthesis of rifamycin, had never been isolated and identified. According to bioinformatics analysis, it was proposed that RifT (a putative NADH-dependent dehydrogenase) may be a candidate target responsible for the dehydrogenation of proansamycin X. In this study, the mutant strain Amycolatopsis mediterranei S699 ΔrifT was constructed by deleting the rifT gene. From this strain, eleven 8-deoxy-rifamycin derivatives (1–11) and seven known analogues (12–18) were isolated. Their structures were elucidated by extensive analysis of 1D and 2D NMR spectroscopic data and high-resolution ESI mass spectra. Compound 1 is a novel amide N-glycoside of seco-rifamycin. Compounds 2 and 3 feature conserved 11,12-seco-rifamycin W skeleton. The diverse post-modifications in the polyketide chain led to the production of 4–11. Compounds 2, 3, 5, 6, 13 and 15 exhibited antibacterial activity against Staphylococcus aureus (MIC (minimal inhibitory concentration) values of 10, 20, 20, 20, 40 and 20 μg/mL, respectively). Compounds 14, 15, 16, 17 and 18 showed potent antiproliferative activity against KG1 cells with IC50 (half maximal inhibitory concentration) values of 14.91, 44.78, 2.16, 18.67 and 8.07 μM, respectively.

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Section: Discussionmentioning

confidence: 99%

8-Deoxy-Rifamycin Derivatives from Amycolatopsis mediterranei S699 ΔrifT Strain

Shi

Zhao

et al. 2020

Biomolecules

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“…The hgc1 -overexpressed mutant strain Streptomyces sp. LZ35 produced three new hygrocins, among which hygrocin H ( 121 ) displayed significant cytotoxic activity against HeLa cells with an IC 50 of 0.8 μM (Li et al, 2015g ).…”

Section: Terrestrial Microorganismsmentioning

confidence: 99%

Natural Products Research in China From 2015 to 2016

et al. 2018

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“…Previously, we have approached to new ansamycins through PCR screening of the AHBA synthase genes of plantassociated, soil-dwelling and marine-derived actinomycetes, 8 which afforded the characterization of the biosynthesis of hygrocins, 8,9 divergolides, 10,11 ansamycins juanlimycins 12 and neoansamycins, 13 and the isolation of ansatrienols B-H with diverse post-PKS modications from the strain Streptomyces sp. XZQH13OEDastC.…”

Section: Introductionmentioning

confidence: 99%