Three taraxerane nortriterpenoids were isolated from mastic by using various modern chromatographic separation techniques. They were identified as(5R,8R,9R,10S,11S,12R,13S,17R,18R)-28-norlupa-11,12-epoxy-14-taraxerene-3,16-dione(1),(5R,8R,9R,10S,11S,12R,13S,17S,18S)-17-hydroxy-28-norlupa-11,12-epoxy-14-taraxerene-3-one(2), and(5R,8R,9R,10R,11S,12R,13R,14S,17S,18S)-14,17-epoxy-28-norlupa-11,12-oxidotaraxerone(3) through the high-resolution electrospray ionization mass spectrometry(HR-ESI-MS), infrared(IR), ultraviolet(UV), nuclear magnetic resonance(NMR), and single-crystal X-ray diffraction techniques as well as comparison with literature data. Compounds 1-3 were C-28 nortriterpenoids and isolated from mastic for the first time, and compounds 1-2 were new ones. In the model for RAW264.7 cell anti-inflammation induced by lipopolysaccharide(LPS), compound 1 demonstrates an inhibitory effect on nitric oxide(NO) [IC_(50)=(13.38±0.68) μmol·L~(-1)], comparable to the activity of the positive control dexamethasone [IC_(50)=(14.59±1.49) μmol·L~(-1)]. Compounds 2 and 3 exhibit weaker inhibitory effects, with IC_(50) values of(24.17±2.56) and(22.25±2.84) μmol·L~(-1), respectively.
Animals ; Mice ; Triterpenes/isolation & purification* ; Drugs, Chinese Herbal/isolation & purification* ; Mastic Resin/chemistry* ; Nitric Oxide ; Molecular Structure ; Macrophages/immunology* ; RAW 264.7 Cells

Ten compounds were separated by various modern chromatographic methods from mastic. They were identified by HR-ESI-MS, IR, UV, NMR, quantum chemical calculation of NMR(qcc-NMR) and comparison with reported data in literature as 17β-hydroxy-28-norolean-18-en-3-one(1), 28-norolean-12,17-dien-3,11-dione(2), 28-norolean-16,18-dien-3-one(3),(24Z)-26-hydroxy-7,24-dientirucalla-3-one(4), masticadienonic acid(5)、masticadienolic acid(6)、erythrodiol(7), 3β,28-dihydroxyoleana-11,13(18)-diene(8), 3-oxo-olean-9(11),12-dien-28-oic acid(9), and 12-oleane-3,11-dione(10). Among them, compound 1 was a novel compound and compound 2 was a novel natural product. Compounds 1-2, 4, and 7-9 were isolated from mastic for the first time. Compound 1 significantly inhibited lipopolysaccharide-induced production of nitric oxide in mouse monocyte macrophage RAW264.7 cells with the IC_(50) of(7.44±0.49) μmol·L~(-1), which was more potent than the positive control, dexamethasone \[IC_(50)=(9.93±1.17) μmol·L~(-1)\]. Compounds 2-3, 5, and 9-10 also showed inhibitory effects, with the IC_(50) ranging from 14.82 to 28.82 μmol·L~(-1). Compounds 4-5, and 7 markedly inhibited the growth of human colon adenocarcinoma cells SW480, with the IC_(50) of(16.13±1.69),(27.40±1.81), and(10.01±0.10) μmol·L~(-1), respectively.
Mice ; Animals ; Mastic Resin/chemistry* ; Humans ; Macrophages/metabolism* ; Triterpenes/isolation & purification* ; Nitric Oxide ; Molecular Structure ; RAW 264.7 Cells ; Drugs, Chinese Herbal/isolation & purification*