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Structure type: oligomer ; 1157.6359 [M+H]+
C₆₁H₉₂N₂O₁₉
Trivial name: lobophorin A
Compound class: glycoside

• 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: 37110828
  Publication DOI: 10.3390/molecules28083597
  Journal NLM ID: 100964009
  Publisher: Basel, Switzerland: MDPI
  Correspondence: Y.W. Duan ; Y. Huang ;
  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
  
   
  
  Streptomyces sp. CB09030, Actinomyces sp. CNB-837, Streptomyces sp. SCSIO 01127, Streptomyces pactum SCSIO 02999, Streptomyces sp. MS100061
  CSDB ID 22314 (all data & tools)

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Structure type: oligomer ; 1209.5921 [M+H]+
C₆₁H₉₀N₂O₂₁
Trivial name: lobophorin B
Compound class: glycoside

• 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: 37110828
  Publication DOI: 10.3390/molecules28083597
  Journal NLM ID: 100964009
  Publisher: Basel, Switzerland: MDPI
  Correspondence: Y.W. Duan ; Y. Huang ;
  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
  
   
  
  Streptomyces sp. CB09030, Actinomyces sp. CNB-837, Streptomyces sp. SCSIO 01127, Streptomyces pactum SCSIO 02999, Streptomyces sp. MS100061
  CSDB ID 24840 (all data & tools)