Chemical constituents of the root ofDystaenia takeshimana and their anti-inflammatory activity

Abstract

In our ongoing search for bioactive compounds originating from the endemic species in Korea, we found that the hexane and EtOAc fractions of the MeOH extract from the root of Dystaenia takeshimana (Nakai) Kitagawa (Umbelliferae) showed cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX) dual inhibitory activity by assessing their effects on the production of prostaglandin D2 (PGD2) and leukotriene C4 (LTC4) in mouse bone marrow-derived mast cells. By activity-guided fractionation, five coumarins, viz. psoralen (2), xanthotoxin (3), scopoletin (4), umbelliferone (5), and (+)-marmesin (6), together with beta-sitosterol (1), were isolated from the hexane fraction, and two phenethyl alcohol derivatives, viz. 2-methoxy-2-(4'-hydroxyphenyl)ethanol (7) and 2-hydroxy-2-(4'-hydroxyphenyl)ethanol (8), three flavonoids, viz. apigenin (9), luteolin (10), and cynaroside (11), as well as daucosterol (12) were isolated from the EtOAc fraction using silica gel column chromatography. In addition, D-mannitol (13) was isolated from the BuOH fraction by recrystallization. Two of the coumarins, scopoletin (4) and (+)-marmesin (6), the two phenethyl alcohol derivatives (7, 8) and the three flavonoids (9-11) were isolated for the first time from this plant. Among the compounds isolated from this plant, the five coumarins as well as the three flavonoids showed COX-2/5-LOX dual inhibitory activity. These results suggest that the anti-inflammatory activity of D. takeshimana might in part occur via the inhibition of the generation of eicosanoids.

Chemical Constituents and Cytotoxic Effect of the Main Compounds of Lythrum salicaria L.

“…The structures of these compounds were determined on the basis of spectroscopic data compared with those reported in the literature. The compounds included three coumarins: umbelliferone-6-carboxylic acid (2) (Zhao et al, 2012), the furanocoumarin peucedanin (12) (Alavi et al, 2008), and buntansin (13) (Huang et al, 1989); three ellagic acid derivatives: 3,3',4'-tri-O-methylellagic acid-4-O-β-D-(2"-acetyl)-glucopyranoside (3), 3,3',4'-tri-Omethylellagic acid-4-O-β-D-glucopyranoside (4), and 3,3',4'-tri-O-methylellagic acid (9) (Ndukwe et al, 2008;Li et al, 1999); three tri terpenes: oleanolic acid (8), erythrodiol (14) (Mahato and Kundu, 1994), and the ursan-type triterpene corosolic acid (10) (Seo et al, 1975); two steroids: daucosterol (5) (Kim et al, 2006) and β-sitosterol (11) (Kim et al, 2005); together with 5-hydroxypyrrolidin-2-one (1) (Chen et al, 2008), phytol (6) (Kim et al, 2005), and dodecanoic acid (7). Compounds 8 and 11 had been previously isolated from this plant but the others were found for the fi rst time.…”

Kazakh Ziziphora Species as Sources of Bioactive Substances

“…Its anti-inflammatory effects are connected mainly with interaction with NF-κB, STAT3 dimerization and overall inhibition of gene expression of pro-inflammatory factors (COX, iNOS) [142]. Z. clinopodioides [44] Immunoregulatory effect [150] Anti-inflammatory activity [151]; anti-inflammatory in ear edema assay [152]; topical anti-inflammatory activity in the mouse ear edema model [153]; weak 5-LOX inhibitory activity [154] DPPH and ABTS; scavenging effect [155]; antioxidant [156]; inhibitory effect on nitric oxide production in LPS-activated RAW264.7 cells [157] Antinociceptive [158] Some anticomplementary activity [159] Neuroprotective [160,161]; promotion of proliferation of neural stem cells [162]; Inhibition of acetylcholinesterase [163] Inhibition of cancer cell proliferation [164], induction of apoptosis [165], antiproliferative [166], cytotoxic [167]; antiproliferative activity against HL-60, K562, HepG2 and CNE-1 cell lines [168] inhibition of MDA-MB-231 cancer cell migration [169]; Ability to activate PPARγ and PPARβ [170] Inhibition of α-glucosidase [171] Antibacterial effect against E. coli [172], against H. pylori and S. aureus [173]; against E. coli and S. aureus [174]; against Bacillus subtilis and S. aureus [175] Inhibitory effect on reverse transcriptase [176] Suppression of HCl/ethanol-induced gastric lesions [177] Inhibitory activity against osteoclast differentiation by suppressing TRAP activity in RANKL-induced RAW 264.7 macrophage cells [178] H…”

“…Several activities of daucosterol (29) are again in accordance with therapeutic potential of Ziziphora species observed both in folk medicine and scientific studies. The anti-inflammatory effect of daucosterol (29) was observed both in vitro and in vivo [152,153] and a 5-LOX inhibitory effect was observed [154]. Daucosterol (29) also acts as scavenger of free radicals in vitro [155] and as an antioxidant [156] and it inhibits nitric oxide production in LPS-activated RAW264.7 cells [157].…”

Alkaloids, Coumarin and Cinnamic Acid Derivative from Murraya koenigii (Linn.) Spreng.

“…12 Linalool, elemol, geranyl acetate, myrcene, alloocimene, α-Terpinene, (E)-β-Ocimene and neryl acetate had been isolated as essential oil from this plant. 13 As a part of our continuing studies with medicinal plants of Bangladesh [14][15][16][17][18] , we studied M. koenigii and we, herein, report the isolation of arborinine (1) 19 , ferulic acid (2) 20 , umbelliferone (3) 21 , mahanimbine (4) 6 , koenimbine (5) 5 , koenidine…”