New oxo acids of the seed oil ofGaleopsis bifida

Anti-inflammatory Constituents of the Red Alga Gracilaria verrucosa and Their Synthetic Analogues

“…Compounds 7 and 12 – 14 , identified as saturated keto fatty acids, were previously prepared from biotransformation or isolated from a few higher plants. – From the CID spectra of [M − H + 2Na] + ions of these compounds, the β ion of 7 , 12 , 13 , and 14 was observed at m / z 187, 187, 201, and 215, respectively, whereas the γ′ ion of 7 , 12 , 13 , and 14 was found at m / z 257, 257, 271, and 285, respectively. These diagnostic ions led to the identification of the position of the keto group at C-10 for 7 and 12 , C-11 for 13 , and C-12 for 14 .…”

“…The brominated analogues (29)(30)(31)(32)(33)(34)(35)(36) were formed by the bromination of the enone fatty acids (15-19, 9, 10, and 20) using Br 2 in CCl 4 followed by base-catalyzed elimination. Subsequent Suzuki coupling of some brominated compounds (29, 31, 35, and 36) with phenylboronic acid mediated by tetrakis(triphenylphosphine)palladinium(0) afforded the corresponding phenyl-substituted analogues (37)(38)(39)(40).…”

“…All of the synthetic compounds (9, 10, and 15-40) were examined for their anti-inflammatory activity through the evaluation of their inhibitory effects on the production of NO (Figure 8). When the activity of six synthetic groups was compared, the potency was in the order brominated (29-36) > hydroxy (21-24) > amide (25-28) > acid (19, 9, 10, and 20) > methyl ester (15-18) > phenyl analogues (37)(38)(39)(40). However, the increased activity of the brominated analogues, which were prepared to enhance the electrophilicity of the β-carbon, 50 was due to their strong cytotoxicity to the cells.…”

Synanthropic Plants as an Underestimated Source of Bioactive Phytochemicals: A Case of Galeopsis bifida (Lamiaceae)

“…The reason for this is lack of knowledge regarding the plant's chemical composition, as well as the lack of information on the pharmacological effects of extraction preparations from it. The known data on the metabolites of G. bifida indicate the presence of iridoids [7,8], flavonoids [17], fatty acids [22][23][24][25], acylglycerols [26], and essential oils [27].…”

“…These species are often found in crops, fields, garbage sites, and alongside roads. Information on the chemical composition of Galeopsis species indicates the presence of iridoids [6][7][8][9][10][11], diterpenes [12][13][14], triterpenes [13], benzoic acids [15], hydroxycinnamates [15,16], flavones [9,15,[17][18][19][20][21], fatty acids [22][23][24][25], acylglycerols [26], and essential oils [27,28] (Table 1). Early pharmacological studies have indicated the presence of central nervous system (CNS) depressive [29], antioxidant [30], neuroprotective, and anticholinesterase activities [31] in extracts of the Galeopsis species.…”