Constituents of the Edible Leaves of Melicope pteleifolia with Potential Analgesic Activity

Abstract

Melicope pteleifolia has long been consumed as a popular vegetable and tea in Southeast Asian countries, including Malaysia and southern mainland China, and is effective in the treatment of colds and inflammation. In the search for active metabolites that can explain its traditional use as an antipyretic, six new phloroacetophenone derivatives (3−8) along with seven known compounds (1, 2, and 9−13) were isolated from the leaves of M. pteleifolia. Their chemical structures were confirmed by extensive spectroscopic analysis including NMR, IR, ECD, and HRMS. All compounds isolated from the leaves of M. pteleifolia (1−13) have a phloroacetophenone skeleton. Notably, the new compound 8 contains an additional cyclobutane moiety in its structure. The bioactivities of the isolated compounds were evaluated, and compounds 1, 6, and 7 inhibited tumor necrosis factor-α-induced prostaglandin E 2 . Moreover, the major constituent, 3,5-di-C-β-D-glucopyranosyl phloroacetophenone (1), was found to be responsible for the antipyretic activity of M. pteleifolia based on in vivo experiments.

Melicopteline A–E, Unusual Cyclopeptide Alkaloids with Antiviral Activity against Influenza A Virus from Melicope pteleifolia

“…Moreover, our previous studies on M. pteleifolia have demonstrated that the phloroacetophenone derivatives dominantly present in the plant play an important role in recovery from cold by lowering excessive heat in the animal model, by which we proved scientifically ethnopharmacological uses of the plant …”

Recent Advances on Natural Aryl-C-glycoside Scaffolds: Structure, Bioactivities, and Synthesis—A Comprehensive Review

“…Phenyl C -glycosides were considered the simplest aryl- C -glycosides. The disclosed structures 140 – 169 feature C - β -D-glucopyranosides, with variations in the substitution on the benzene ring ( Figure 5 ) [ 24 , 25 , 26 , 27 , 80 , 81 , 82 , 83 , 84 ]. The site of C -glycosylation is usually the ortho position of the phenolic hydroxyl group.…”

“…Ardimerin digallate ( 169 ) was isolated from the whole plant of Ardisia japonica and was shown to inhibit HIV-1 and HIV-2 RNase H in vitro, with IC 50 values of 1.5 and 1.1 µM, respectively [ 27 ]. The compound 3,5-di- C - β -D-glucopyranosyl phloroacetophenone ( 155 ), isolated from the edible leaves of Melicope pteleifolia , was found to be responsible for the antipyretic activity of M. pteleifolia based on in vivo experiments [ 26 ]. Calophymembranside C ( 141 ), isolated from the stems of Calophyllum membranaceum , showed transcriptional inhibitory activity towards RXRα, with 50% inhibitory concentration (IC 50 ) values of 29.95 ± 1.08 [ 24 ].…”

Sex-dependent variations in anti-nociceptive and antipyretic effects of rhizome and stem extract of Schumannianthus dichotomus Roxb. in male and female mice

“…Folkloric uses of plants against different diseases act as a pivot to explore those plants for new bioactive compounds and affirmative activities of crude plant extracts usher identification and isolation of many compounds. For instance, in recent years, several compounds from plant sources have been reported to possess antinociceptive (Mizokami et al, 2012;Nieto et al, 2013;Sun et al, 2019) and antipyretic effect (Lee et al, 2019;Muhammad et al, 2019). A good number of plants native to Bangladesh have been traditionally used against pain and fever and their effects are underpinned by experimental findings in animal model (Ferdous et al, 2020;Roy et al, 2019;Subedi et al, 2016).…”