Anti-Inflammatory Triterpenoids from the Stems of Microtropis Fokienensis

Abstract

Three new ursane-and four new oleanane-type triterpenoids 1-7 were isolated, along with six known compounds 8-13, from the methanolic extract of Microtropis fokienensis. All structures were elucidated by mass and NMR spectroscopic methods. The isolates 4-10 and known compounds 14-17 that were previously isolated from this material were evaluated for anti-inflammatory activity based on effects against superoxide anion generation and elastase release by neutrophils in response to fMLP/CB. 11α,30-Dihydroxy-2,3-seco-olean-12-en-2,3-dioic anhydride (7) was the first triterpene anhydride from the genus of Microtropis to have the ring A expanded to a seven-membered ring; it showed significant anti-inflammatory activity against superoxide anion generation and elastase release. Unexpectedly, 30-hydroxy-2,3-seco-lup-20(29)-ene-2,3-dioic acid (17) showed the best effect against superoxide anion generation and elastase release with IC 50 values of 0.06 ± 0.01 and 1.03 ± 0.35 µg/mL, respectively. Compound 17 had a dioic acid function, and compound 7 had an anhydride function modification in ring A; both showed promising activity in the target assays.

Antagonism of human formyl peptide receptor 1 with natural compounds and their synthetic derivatives

“…These compounds have 4- or 5-ring skeletons and hydroxyl, carboxyl, or oxo groups and are biosynthesized in plants via squalene cyclization. Several triterpenoids isolated from the stems of Microtropis fokienensis inhibited f MLF-induced O 2 −· generation and HNE release by neutrophils, with the most potent being 30-hydroxy-2,3- seco -lup-20(29)-ene-2,3-dioic acid (triterpene 17 ; Table 1), bearing two carboxylic groups [141]. Oleanolic (Table 1), ursolic, and betulinic acids are known triterpenes with anti-inflammatory and immunomodulatory properties [142].…”

“… Compound numbers for dipeptide 3 , isoflavones ( 36 , 68 , and 73 ), ugonin 3 , triterpene 17, and ent -kaurane 1 are as designated in previous reports [62, 79, 95, 141, 165]. …”

Cytotoxic Triterpenoids from the Stalks of Microtropis triflora

“…3) analyses and compared the NMR data to known compound. The NOE correlations between Me(23) and H-C(3), as well as between H-C (24) and Me (25) were observed in the 2D-NOESY spectrum, but no NOE correlations between H-C(2) and H-C(3), between Me(23) and H-C(24), or between Me(23) and Me (25) were observed. These NOE information revealed that H-C(2) is in b-configuration (2-OH a-configuration), H-C(3) and Me(23) are both in a-configuration.…”

Immunomodulatory effects ofSantolina chamaecyparissusleaf extracts on human neutrophil functions

“…In this regard, traditional medicine worldwide is nowadays being re-evaluated by extensive research on different medicinal plants and their therapeutic principles (Dalli et al, 2008;Yuandani et al, 2013). Many plants represent a source of new compounds with antiinflammatory and antioxidant activity (Chen et al, 2014;Hwang et al, 2006;Yuandani et al, 2013).…”