Orthoquinone and Naphthalenone Derivatives from Berrya ammonilla and Their Anti-Inflammatory Activity

Abstract

A new orthoquinone, berryammone A (1), and four new naphthalenone derivatives, berryammone B (2), berryammone C (3), 6-O-methylberryammone C (4), and 4-O-methylberryammone C (5), have been isolated from the stem of Berrya ammonilla, together with eleven known compounds (6-16). The structures of these new compounds were determined through spectroscopic and MS analyses. Among the isolates, compounds 1-3, 5, (+)-pinoresinol (6), and betulinic acid (12) exhibited inhibition (IC50 ≤ 4.41 µM) of superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB). Compounds 1, 2, and 5 also inhibited fMLP/CB-induced elastase release with IC50 values ≤ 3.95 µM.

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

“…There are several publications on their effects in f MLF-treated neutrophils. For example, berryammone A and naphthalenone derivatives, berryammone B (Table 1) and 4- O -methylberryammone C, isolated from the stem of Berrya ammonilla exhibited a relatively potent inhibition of f MLF-induced O 2 −· generation and HNE release by neutrophils [116]. Likewise, a related methyl naphthalene carboxylate, lawsonaphthoate A (Table 1), and had potent inhibitory activity [73].…”

“…Epibetulinic acid (Table 1) isolated from Pachycentria formosana demonstrated similar inhibitory effects as oleanolic acid [143], and its derivative, betulinic acid, also inhibited f MLF-induced O 2 −· production by neutrophils. However, this triterpene did not affect f MLF-induced release of HNE [116], suggesting that it has an FPR1-independent mechanism of action. Although α-amyrin, uvaol, ursolic acid, 19α-hydroxy ursolic acid, and 19α, 24-dihydroxy ursolic acid inhibited f MLF-induced O 2 −· production, all of these triterpenes also inhibited O 2 −· generation stimulated by arachidonic acid [147], suggesting nonspecific effects of these compounds and/or interaction with post-FPR1 pathways.…”

Cichorins D–F: Three New Compounds from Cichorium intybus and Their Biological Effects

“…In turn, the methyl group at C-2 was evident based on HMBC correlations of this methyl group (δ H 1.52) to C-1, C-2, and C-3. Based on NMR analysis, the compound was found to be a naphthalenone derivative and a literature survey illustrated that the naphthalene analog, berryammone B, reported from the plant Berrya ammonilla, also comprises of a keto group at C-1 and a similar C-2 chiral centre as our new compound 1 [ 39 ].…”

“…Moreover, the saturated quaternary carbon at δ C 87.1 suggested that the hydroxyl group is attached to C-2. Moreover, the tentative assignment of absolute configuration of compound 1 was established by comparing specific rotation data with a similar published compound, berryammone B [ 39 ]. As a result, the chemical structure of compound 1 was confirmed to be 2-hydroxy-7-methoxy-2-methylnaphthalen-1(2 H )-one, named cichorin D based on the producing plant.…”

“…The literature revealed that only a few 1,2-dihydronaphthalane derivatives have been reported to bear a keto group at C-1 and a chiral centre at C-2 (similar as compound 1 ) having a hydroxyl and alkyl group. Compounds with similar structures include 7-dihydroxy-3(4 H )-isocadalen-4-one [ 49 ], Berryammone B [ 39 ], trichbenzoisochromen A [ 50 ], and bombamalone A [ 51 ]. Moreover, various naphthalene compounds (aglycones and glycosides) have been reported from plants that have similar substitution patterns, as in compound 2 .…”