Two New 3,4;9,10- seco-Cycloartane Type Triterpenoids from Illicium difengpi and Their Anti-Inflammatory Activities

Abstract

A pair of new 3,4;9,10- seco-cycloartane type triterpenoid stereoisomerides: 24R,25-dihydroxy-3,4;9,10- seco-4(28)-cycloarten-10,3-olide ( 1) named Illiciumolide A and 24S,25-dihydroxy-3,4;9,10- seco-4(28)-cycloarten-10,3-olide ( 2) named Illiciumolide B were isolated from the stem bark of Illicium difengpi, as well as five known biogenetically related triterpenoids, including sootepin E ( 3), betulinic acid ( 4), lupeol ( 5), (all- Z)-1,5,9,13,17,21-hexamethyl-1,5,9,13,17,21-cyclotertracosahexaene ( 6), and (all- E)-2,6,10,15,19,23-hexamethyl-2,6,10,14,18,22-tetracosahexaene ( 7). The structures of two new compounds were determined on the basis of spectroscopic analysis including 1D-, 2D-NMR, and MS techniques. Two assays were conducted: inhibition of tumor necrosis factor-alpha (TNF- α) and inhibition of nuclear factor kappa B (NF- κB) in RAW264. 7 cells induced by lipopolysaccharide (LPS). It was observed that compounds 1, 2 and 7 showed significant inhibition of TNF- α production and NF- κB release. The molecule docking results showed that compounds 1 and 2 got high fitness scores with dual specificity mitogen-activated protein kinase kinase 1 (MPKK1), whose activation plays a pivotal role between TNF- α and activation of NF- κB. The anti-HIV-1 potency of compounds 1– 5 was also discussed, in addition to the results of computer-aided screening for targets.