708253-29-6Relevant articles and documents
BIOLOGICALLY ACTIVE PHENOLIC METABOLITES OF A VERTICICLADIELLA SPECIES
Ayer, William A.,Browne, Lois M.,Lovell, Sarah H.
, p. 2267 - 2272 (1983)
The metabolites produced when a Verticicladiella species (Canadian Forestry Service strain C728), the causative agent of the black stain root disease of many conifers, is grown in liquid culture have been investigated.Orcinol, orcinol monomethyl ether, 1,3,6,8-tetrahydroxyanthraquinone, and the α-L-rhamnopyranosides of orcinol and orcinol methyl ether have been isolated and indentified.Orcinol methyl ether and its rhamnoside both show antibacterial activity and orcinol methyl ether also inhibits the growth of pine germlings.The general antibacterial activity of 5-alkylresorcinols and their monomethyl ethers is reported.-Key Word Index-Verticicladiella sp.; Deuteromycontina; blue-stain fungus; phytotoxin; phenols; methylorcinol rhamnoside; phenol monomethyl ethers; antiseptics.
Euodenine A: A small-molecule agonist of human TLR4
Neve, Juliette E.,Wijesekera, Hasanthi P.,Duffy, Sandra,Jenkins, Ian D.,Ripper, Justin A.,Teague, Simon J.,Campitelli, Marc,Garavelas, Agatha,Nikolakopoulos, George,Le, Phuc V.,De A. Leone, Priscila,Pham, Ngoc B.,Shelton, Philip,Fraser, Neil,Carroll, Anthony R.,Avery, Vicky M.,McCrae, Christopher,Williams, Nicola,Quinn, Ronald J.
, p. 1252 - 1275 (2014/03/21)
A small-molecule natural product, euodenine A (1), was identified as an agonist of the human TLR4 receptor. Euodenine A was isolated from the leaves of Euodia asteridula (Rutaceae) found in Papua New Guinea and has an unusual U-shaped structure. It was synthesized along with a series of analogues that exhibit potent and selective agonism of the TLR4 receptor. SAR development around the cyclobutane ring resulted in a 10-fold increase in potency. The natural product demonstrated an extracellular site of action, which requires the extracellular domain of TLR4 to stimulate a NF-κB reporter response. 1 is a human-selective agonist that is CD14-independent, and it requires both TLR4 and MD-2 for full efficacy. Testing for immunomodulation in PBMC cells shows the induction of the cytokines IL-8, IL-10, TNF-α, and IL-12p40 as well as suppression of IL-5 from activated PBMCs, indicating that compounds like 1 could modulate the Th2 immune response without causing lung damage.
