Isolation and Structure Elucidation of Cytotoxic Saccharothriolides D to F from a Rare Actinomycete Saccharothrix sp. and Their Structure–Activity Relationship

Journal of Natural Products
2016.0

Abstract

Three new 10-membered macrolides, saccharothriolides D-F (1-3), were isolated from a rare actinomycete, Saccharothrix sp. A1506. The planar structures were determined from analysis of extensive NMR and HR-ESI-MS data, and the absolute configurations were established by ECD spectroscopy analysis. Saccharothriolides D (1) and E (2) were determined to be C-2 epimers of saccharothriolides A (4) and B (5), respectively. Saccharothriolide F (3) was identified to be a demethylated congener of saccharothriolides D (1) and A (4) at the C-2 position. The availability of compounds 1-6 enabled a structure-activity relationship study that revealed the importance of the phenolic hydroxy group at C-2″ and the stereochemistry of C-2 for the inhibition of human fibrosarcoma HT1080 cell growth.

Knowledge Graph

Similar Paper

Isolation and Structure Elucidation of Cytotoxic Saccharothriolides D to F from a Rare Actinomycete <i>Saccharothrix</i> sp. and Their Structure–Activity Relationship
Journal of Natural Products 2016.0
Isolation and Structure Elucidation of Cytotoxic Saccharothriolides D to F from a Rare Actinomycete <i>Saccharothrix</i> sp. and Their Structure–Activity Relationship
Journal of Natural Products 2016.0
Saccharothriolides A–C, novel phenyl-substituted 10-membered macrolides isolated from a rare actinomycete Saccharothrix sp.
Chemical Communications 2015.0
Saccharothrixones A–D, Tetracenomycin-Type Polyketides from the Marine-Derived Actinomycete <i>Saccharothrix</i> sp. 10-10
Journal of Natural Products 2015.0
Structurally diverse metabolites from the rare actinobacterium Saccharothrix xinjiangensis
The Journal of Antibiotics 2020.0
Cytotoxic Trichothecene Macrolides Produced by the Endophytic <i>Myrothecium roridum</i>
Journal of Natural Products 2019.0
Structure-activity studies of irumamycin type macrolides from Streptomyces sp. INA-Ac-5812
Tetrahedron Letters 2019.0
Structures and Cytotoxic Properties of Trichoverroids and Their Macrolide Analogues Produced by Saltwater Culture of <i>Myrothecium </i><i>v</i><i>errucaria</i>
Journal of Medicinal Chemistry 2003.0
A novel macrolactam-disaccharide antifungal antibiotic. Taxonomy, fermentation, isolation, physico-chemical properties, structure elucidation and biological activity.
The Journal of Antibiotics 1993.0
Sacchathridine A, a Prostaglandin Release Inhibitor from <i>Saccharothrix</i> sp.
Journal of Natural Products 2013.0