Constituents in Evening Primrose Oil with Radical Scavenging, Cyclooxygenase, and Neutrophil Elastase Inhibitory Activities

Abstract

Cold-pressed, non-raffinated evening primrose oil was found to contain lipophilic radical scavengers. A highly enriched fraction of these compounds could be obtained from the oil by extraction with aqueous ethanol and subsequent liquid-liquid partitioning with petroleum. LC-DAD-MS analysis revealed that the fraction contained three aromatic compounds with identical UV and ESI-MS spectra. The compounds were isolated by RP-HPLC and their structures established by chemical and spectroscopic means as 3-O-trans-caffeoyl derivatives of betulinic, morolic, and oleanolic acid. The morolic acid derivative was a new compound. The three esters exhibited pronounced radical scavenging activity against the stable 2,2-diphenyl-1-picrylhydrazyl radical and were potent inhibitors of neutrophil elastase and cyclooxygenase-1 and -2 in vitro. Commercial samples of evening primrose oils contained only traces of these lipophilic antioxidants.

Antiinflammatory activities of flavonoids and a triterpene caffeate isolated from Bauhinia variegata

“…In addition, the results also support the earlier findings that compound 1 inhibited the LPSinduced NO production in RAW 264.7 macrophages in a concentration-dependent manner (Wang and Mazza, 2002;Lin et al, 2003). Additionally, it has been reported that compound 7 exhibited radical-scavenging activity in a DPPH assay Copyright © 2008 system, and inhibition of eicosanoid synthesis catalysed by COX-1 and COX-2 (Hamburger et al, 2002;Roland and Hamburger, 2004). The p-coumaroyl ester of oleanolic acid, a compound closely related to 7, had been shown to exert potential cancer chemopreventive activity (Gu et al, 2001).…”

“…The concentrated n-BuOH layer (20 g, 1.0%, w/w) was subjected to CC on silica gel and eluted with a gradient of CHCl 3 and MeOH (9:1 to 100% MeOH) to give kaempferol 3-O-β-Dglucopyranoside (4, 30 mg, 0.0015%), isorhamnetin 3-O-β-D-glucopyranoside (5, 21 mg, 0.0011%), hesperetin 7-O-rutinoside (hesperidin, 6, 16 mg, 0.0008%) and 3β-trans- (3,4-dihydroxycinnamoyloxy)olean-12-en-28-oic acid (7, 12 mg, 0.0006%). The structures of flavonoids (1-6), and a triterpene caffeate (7), were elucidated by detailed 1 H and 13 C NMR spectroscopy and by comparison of the spectral data with published values (Pan et al, 1994;Xiong et al, 1995;Sultana et al, 1999;Hamburger et al, 2002;Reddy et al, 2003;Li et al, 2004;Daniel et al, 2004). The molecular masses of compounds 1, 2, 3, 4, 5, 6 and 7 were 286,330,476,448,478,610 and 618 g/mol, respectively, as determined by ESI-MS.…”

Bioactive triterpenoids from Callistemon lanceolatus

“…Thus, the structure of the new compound 1 was determined to be 30-hydroxyalphitolic acid [2α,3β,30-trihydroxylup-20(29)-en-28-oic acid]. In addition, the other eight compounds isolated were identified as alphitolic acid (2) (Kuang et al, 1989), lupenol (3) (Burns et al, 2000), 3-acetoxy-olean-18-en-28-oic acid (4) (Li et al, 2004), betulinic aicd (5) (Cichewicz and Kouzi, 2004), ursolic acid (6) (Seebacher et al, 2003), betulinic acid 3-O-caffeate (7) (Pan et al, 1994), morolic acid 3-O-caffeate (8) (Hamburger et al, 2002), and ursolic acid 3-O-caffeate (9) (Tanachatchairatana et al, 2008), by interpreting spectral data and making comparisons with literature values.…”

Functional components in Luffa cylindrica and their effects on anti-inflammation of macrophage cells

“…Similarly, in a study dealing with LPS/IFN-c induced inflammation in RAW 264.7 cells, oleanolic acid (10 lM) showed no significant effect in reducing PGE 2 concentration as well as COX-2 expression. In contrast, Hamburger et al (2002) isolated three triterpene acids, namely betulinic acid, morolic acid and oleanolic acid from evening primrose oil, all of which were effective in inhibiting COX-1 and COX-2 expression in vitro. The anti-inflammation of oleanolic acid may be due to its conjugation with sPLA 2 , resulting in inactivation of sPLA 2 (Dharmappa, Kumar, Nataraju, Mohamed, Shivaprasad, & Vishwanath, 2009).…”