Mansoin F: TNF-α Inhibiting Heterotrimeric Flavonoid From Mansoa Hirsuta DC

Mansoa hirsuta DC (Bignoniaceae) is a liana found in the Brazilian Atlantic forest. In a previous study we isolated two heterotrimeric glucosilated flavonoids comprising a flavanone core linked to two 1,3-diarylpropane C6-C3-C6 units, named mansoins A (1) and B (2) [1]. Continued investigation of the polyphenolic pool of the fruits of Mansoa hirsuta DC (Bignoniaceae) afforded a new member of this class of flavonoids. The structure and absolute configuration of mansoin F (3) were established by NMR analysis and electronic circular dichroism data. Mansoin F (3) was identified as triglucosylated heterotrimer, isomeric with mansoin A (1). Mansoin F (3) inhibited TNF-α release by LPS-stimulated THP-1 cells (IC50 of 19.3 ± 1.3µM) and along with mansoin A (1) reduced the phosphorylation levels of p-65-NF-κB, when assayed at 50µM. These results indicate that the potential anti-inflammatory properties of mansoin F (3) is probably due to inhibition of the NF-κB pathway.