Anti-Inflammatory and Antinociceptive Studies of Hydroalcoholic Extract from the Leaves of Phyllanthus brasiliensis (Aubl.) Poir. and Isolation of 5-O-β-d-Glucopyranosyljusticidin B and Six Other Lignans

Abstract

The aim of this study was to investigate the chemical composition and the antiinflammatory/antinociceptive properties of the hydroalcoholic extract derived from the leaves of Phyllanthus brasiliensis (HEPB) in rodents. A new arylnaphthalene lignan glycoside, 5-O-β-d-glucopyranosyljusticidin B, together with six known lignans, were isolated from HEPB. 1D and 2D NMR experiments and HRMS were used to elucidate the structure of the new compound. HEPB toxicity and antinociceptive activity were evaluated through acute oral toxicity and formalin models in mice, respectively. The anti-inflammatory effects of HEPB were assessed using carrageenan- and dextran-induced paw edema models in rats. HEPB showed low toxicity. Oral administration of HEPB reduced paw edema induced by carrageenan, but not by dextran. HEPB and its fractions from FR6 to FR10 (FR6-10) inhibited the neurogenic and inflammatory phases of formalin-induced linking, demonstrating its antinociceptive activity. These results indicated that lignans from Phyllanthus brasiliensis exerted antinociceptive/anti-inflammatory effects not related to the histaminergic pathway.

Total synthesis of justicidin B, justicidin E, and taiwanin C: A general and flexible approach toward the synthesis of natural arylnaphthalene lactone lignans

“…Next, a Pd-catalyzed Stille cross-coupling of triflate 10a with tributylstannyl methanol in the presence of Pd(PPh 3 ) 4 , Cs 2 CO 3 , and LiCl followed by spontaneous lactonization provided natural justicidin B ( Zhang et al, 2019 ). The NMR spectra of our synthetic sample were in full agreement with those reported in the literature ( Okigawa et al, 1970 ; Borges et al, 2018 ).…”

Secure and Sustainable Sourcing of Plant Tissues for the Exhaustive Exploration of Their Chemodiversity

“…Standards of the compounds 12α-acetoxyl-20β,21β-22α,23α-diepoxyswietephragmin C, 12α-acetoxyswietephragmin D, 3β- O -detigloyl-3β- O -benzoyl-6- O -acetylswietephragmin D, 6-acetoxy-12α-deacetoxyl-8,9,30-ortho-tigloylate-swietemacrophine, 12α-acetoxyswietephragmin C, 8,9,30- ortho -tigloylate swietemacrophine, 3β- O -detigloyl-3β- O -benzoyl-6- O -acetylswietephragmin E, 3β- O -detigloyl-3β- O -benzoyl-12α-acetoxyswietephragmin D were previously isolated from S. macrophylla leaves [ 12 , 40 , 41 ] standards physalin B, physalin G, physalin D and isophysalin B were from P . angulata leaves [ 39 ] and arabelline, 4- O -β- d -apiofuranosyl-(1′′′,6′′)-β-D-glucopyranosyl-diphyllin, 5- O -β-D-glucopyranosyljusticidin B, cleistanthin B, phyllanthostatin A, tuberculatin and justicidin B from the leaves of P. brasiliensis [ 48 ].…”

Chemical Components and Biological Activities of the Genus Phyllanthus: A Review of the Recent Literature

“…Phenylpropanoids constitute the most prevalent class of compounds in the genus Phyllanthus . Thirty seven compounds ( Figure 1 , Table 1 ) were identified from P. glaucus [ 23 ], P. amarus [ 24 , 25 , 26 ], P. urinaria [ 24 ] and P. brasiliensis [ 27 ]. Among these compounds lignans such as neolignan, norlignan and sesquineolignan were the most prominent.…”