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Anthrabenzoxocinones from Streptomyces sp. as liver X receptor ligands and antibacterial agents.

Publication ,  Journal Article
Herath, KB; Jayasuriya, H; Guan, Z; Schulman, M; Ruby, C; Sharma, N; MacNaul, K; Menke, JG; Kodali, S; Galgoci, A; Wang, J; Singh, SB
Published in: J Nat Prod
September 2005

Liver X receptors (LXR) are nuclear hormone receptors that play a critical role in cholesterol homeostasis. They regulate the expression of the ABCA1 gene, which mediates the efflux of cholesterol out of cells. LXR agonists are expected to increase cholesterol efflux, lower LDL, and raise HDL levels. Screening of a natural product library of microbial extracts using a LXR-SPA binding assay and bioassay-guided fractionation of an active extract of a Streptomyces sp. (MA6657) led to the discovery of two new hexacyclic aromatic ketones, (-)-anthrabenzoxocinone [(-)-ABX (1)], an enantiomer of BE-24566B, and (-)-bischloroanthrabenzoxocinone [(-)-BABX (2)]. The IC50 values of LXRalpha-SPA binding are 2 microM for (-)-ABX and 10 microM for (-)-BABX. This extract was also found to inhibit type II fatty acid synthesis, and its active component, (-)-BABX, was responsible for the majority of the inhibition. All three compounds showed good Gram-positive antibacterial activity (MIC 0.5-2 microg/mL). Details of the isolation, structure elucidation, LXR ligand binding, antibacterial activity, and selectivity of inhibition of 1 and 2 are described.

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Published In

J Nat Prod

DOI

ISSN

0163-3864

Publication Date

September 2005

Volume

68

Issue

9

Start / End Page

1437 / 1440

Location

United States

Related Subject Headings

  • Streptomyces
  • Stereoisomerism
  • Receptors, Cytoplasmic and Nuclear
  • Orphan Nuclear Receptors
  • Molecular Structure
  • Medicinal & Biomolecular Chemistry
  • Liver X Receptors
  • Ligands
  • Inhibitory Concentration 50
  • Heterocyclic Compounds, 4 or More Rings
 

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Herath, K. B., Jayasuriya, H., Guan, Z., Schulman, M., Ruby, C., Sharma, N., … Singh, S. B. (2005). Anthrabenzoxocinones from Streptomyces sp. as liver X receptor ligands and antibacterial agents. J Nat Prod, 68(9), 1437–1440. https://doi.org/10.1021/np050176k
Herath, Kithsiri B., Hiranthi Jayasuriya, Ziqiang Guan, Marvin Schulman, Carolyn Ruby, Neelam Sharma, Karen MacNaul, et al. “Anthrabenzoxocinones from Streptomyces sp. as liver X receptor ligands and antibacterial agents.J Nat Prod 68, no. 9 (September 2005): 1437–40. https://doi.org/10.1021/np050176k.
Herath KB, Jayasuriya H, Guan Z, Schulman M, Ruby C, Sharma N, et al. Anthrabenzoxocinones from Streptomyces sp. as liver X receptor ligands and antibacterial agents. J Nat Prod. 2005 Sep;68(9):1437–40.
Herath, Kithsiri B., et al. “Anthrabenzoxocinones from Streptomyces sp. as liver X receptor ligands and antibacterial agents.J Nat Prod, vol. 68, no. 9, Sept. 2005, pp. 1437–40. Pubmed, doi:10.1021/np050176k.
Herath KB, Jayasuriya H, Guan Z, Schulman M, Ruby C, Sharma N, MacNaul K, Menke JG, Kodali S, Galgoci A, Wang J, Singh SB. Anthrabenzoxocinones from Streptomyces sp. as liver X receptor ligands and antibacterial agents. J Nat Prod. 2005 Sep;68(9):1437–1440.
Journal cover image

Published In

J Nat Prod

DOI

ISSN

0163-3864

Publication Date

September 2005

Volume

68

Issue

9

Start / End Page

1437 / 1440

Location

United States

Related Subject Headings

  • Streptomyces
  • Stereoisomerism
  • Receptors, Cytoplasmic and Nuclear
  • Orphan Nuclear Receptors
  • Molecular Structure
  • Medicinal & Biomolecular Chemistry
  • Liver X Receptors
  • Ligands
  • Inhibitory Concentration 50
  • Heterocyclic Compounds, 4 or More Rings