Two New 3,4;9,10-seco-Cycloartane Type Triterpenoids fromIllicium difengpiand Their Anti-Inflammatory Activities

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- κ B) 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- κ B 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- κ B. The anti-HIV-1 potency of compounds 1 – 5 was also discussed, in addition to the results of computer-aided screening for targets.