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1. (Article ID: 6462)
Shi J, Peng D, Peng FF, Zhang QB, Duan YW, Huang Y
The Isolation and Structure Elucidation of Spirotetronate Lobophorins A, B, and H8 from Streptomyces sp. CB09030 and Their Biosynthetic Gene Cluster
Molecules 28(8) (2023)
3597
Lobophorins (LOBs) are a growing family of spirotetronate natural products with significant cytotoxicity, anti-inflammatory, and antibacterial activities. Herein, we report the transwell-based discovery of Streptomyces sp. CB09030 from a panel of 16 in-house Streptomyces strains, which has significant anti-mycobacterial activity and produces LOB A (1), LOB B (2), and LOB H8 (3). Genome sequencing and bioinformatic analyses revealed the potential biosynthetic gene cluster (BGC) for 1-3, which is highly homologous with the reported BGCs for LOBs. However, the glycosyltransferase LobG1 in S. sp. CB09030 has certain point mutations compared to the reported LobG1. Finally, LOB analogue 4 (O-β-D-kijanosyl-(1→17)-kijanolide) was obtained through an acid-catalyzed hydrolysis of 2. Compounds 1-4 showed different antibacterial activities against Mycobacterium smegmatis and Bacillus subtilis, which revealed the varying roles of different sugars in their antibacterial activities.
Streptomyces, lobophorins, anti-mycobacterial activity, spirotetronate, transwell
NCBI PubMed ID: 37110828Publication DOI: 10.3390/molecules28083597Journal NLM ID: 100964009Publisher: Basel, Switzerland: MDPI
Correspondence: Y.W. Duan
sina.com>; Y. Huang csu.edu.cn>; ihm.ac.cn>
Institutions: Xiangya International Academy of Translational Medicine, Central South University, Changsha 410013, China, School of Pharmaceutical Sciences, Changsha Health Vocational College, Changsha 410100, China, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China, Hunan Engineering Research Center of Combinatorial Biosynthesis and Natural Product Drug Discovery, Changsha 410011, China, National Engineering Research Center of Combinatorial Biosynthesis for Drug Discovery, Changsha 410011, China, Institute of Health and Medicine, Hefei Comprehensive National Science Center, Hefei 230093, China
Methods: 13C NMR, 1H NMR, NMR-2D, acid hydrolysis, bioinformatic analysis, CC, RP-HPLC, fermentation, phylogenetic analysis, HR-ESI-MS, antibacterial assay, cytotoxicity assay, genome sequencing, HR-ESI-MS/MS
The publication contains the following compound(s):
- Compound ID: 16651
|
Subst2-(1-4)-b-D-Sugp-(1-17)-+
|
b-L-Digp4Me-(1-4)-a-L-Digp-(1-3)-a-L-Digp-(1-9)-Subst
Sug = 3C-methyl-3,4-diamino-2,3,4,6-tetradeoxy-xylo-hexose = SMILES C[C@H]1O{1}[C@@H](O)C[C@](C)(N){4}[C@H]1N;
Subst = kijanolide = SMILES C/C3=C/C{17}[C@H](O)/C(C)=C\[C@H]1\C=C(CO)/[C@H](C)C[C@]12OC(=O)/C(=C2/O)C(=O)[C@]5(C)[C@H]3/C=C\[C@@H]4{9}[C@@H](O)[C@@H](C)C[C@H](C)[C@H]45;
Subst2 = carbamic acid methyl ester = SMILES CO{1}C(N)=O |
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Structure type: oligomer
; 1157.6359 [M+H]+
C61H92N2O19
Trivial name: lobophorin A
Compound class: glycoside
- Compound ID: 16652
|
Subst2-(1-4)-b-D-Sugp-(1-17)-+
|
b-L-Digp4Me-(1-4)-a-L-Digp-(1-3)-a-L-Digp-(1-9)-Subst
Sug = 3C-methyl-3-nitro-4-amino-2,3,4,6-tetradeoxy-xylo-hexose = SMILES C[C@H]1O{1}[C@@H](O)C[C@](C)(N(=O)=O){4}[C@H]1N;
Subst = kijanolide = SMILES C/C3=C/C{17}[C@H](O)/C(C)=C\[C@H]1\C=C(CO)/[C@H](C)C[C@]12OC(=O)/C(=C2/O)C(=O)[C@]5(C)[C@H]3/C=C\[C@@H]4{9}[C@@H](O)[C@@H](C)C[C@H](C)[C@H]45;
Subst2 = carbamic acid methyl ester = SMILES CO{1}C(N)=O |
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Structure type: oligomer
; 1209.5921 [M+H]+
C61H90N2O21
Trivial name: lobophorin B
Compound class: glycoside
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