Isolation and analgesic property of lupeol from Diospyros mespiliformis stem bark

Abstract

Diospyros mespiliformis Hochst (Ebenaceae) stem bark is used in traditional medicine for the management of pain related ailments. Several bioactive compounds have previously been isolated from the plant material that includes pentacyclic triterpenes. This study sequentially extracted and carried out a bioassay-guided fractionation of the plant crude material with solvents of varying polarity using analgesic efficacy in rats as bioactivity marker, aimed to isolate the active constituent. Powdered stem bark of the plant was sequentially extracted with hexane, chloroform and methanol; and preliminary tested for analgesic activity. The chloroform extract being the most active amongst the three extracts was subjected to column chromatography, and a fraction was eluted with mixture of hexane and ethyl acetate (50:50%) which yielded a compound. Three dose levels (25, 50 and 100 mg/kg) of the compound were administered orally to rats. Acetylsalicylic acid (100 mg/kg, p.o.) was used as the positive control. Nociception was induced mechanically using analgesy meter, and chemically with formalin. The compound alleviated the pain stimulus induced by the analgesy-meter and formalin in rats. The isolated compound was identified as lupeol using thermo-analysis (DSC), colorimetric, chromatographic and spectrometric techniques that included: UV-visible, IR, and 13 C-and 1 H NMR. It was concluded that lupeol acting alone or synergistically might be responsible for the beneficial effect of the plant in treatment of pain related ailments.

A New Ceramide (Rumexamide) and Other Chemical Constituents from <i>Rumex abyssinicus</i> Jacq (Polygonaceae): Isolation, Characterization, Antibacterial Activities and Chemophenetic Significance

“…The structures of compounds 2-17 were determined on the basis of the spectroscopic and mass spectrometric data as bis-(2-ethylhexyl) phthalate (2) [22], Chrysophanol (3) [24], physcion (4), citreorosein (5) [31], emodin (6) [25], chrysophanein (7) and physcionin (8) [32], lupeol (9) [23], 3β, 28-dihydroxylup-20(29)-ene (10) [27], 3β-dihydroxylup-20(29)-en-28-oic acid (11) [27], oleanolic acid (12) [29], ergosta-6,22-diene-3,5,8-triol (13) [30], stigmastane-3,6-dione ( 14) [28], β-sitosterol (15) and stigmasterol (16) [26], stigmasterol 3-O-β-Dglucoside (17) [21] (Figure 1). Compound 1 was obtained as white powder in n-hexane-EtOAc (30:70, v/v).…”

“…Compounds 1 (30.8 mg), 17 (15.5 mg) [21] and 2 (6.8 mg) [22] were obtained after purification of fraction F (2 g) on silica gel column chromatography using n-hexane-EtOAc (40:60 → 00:100, v/v). Fraction A (4 g) was purified on silica gel column chromatography with n-hexane-EtOAc as eluent (95:5, v/v) to yield compounds 9 (10.2 mg) [23],…”

Bioactivities of stem bark of Albizia chinensis Osbeck. Merr., Chakua Koroi of Bangladesh

“…Lupeol and lupeol linoleate demonstrated antiinflammatory potential by showing a reduction in paw swelling in adjuvant arthritis and the outcome was comparable to indomethacin (Geetha and Varalakshmi, 2001). Lupeol and lupeol acetate have been reported to exhibit anti-nociceptive and anti-inflammatory activities in vivo and in vitro (Adzu et al, 2015;Chen et al, 2012). On the other hand, quercetin and isoquercitrin were found to be effective in allergies by acting as eosinophilic inflammation suppressors (Rogerio et al, 2007).…”

The Genus Diospyros: A Review of Novel Insights into the Biological Activity and Species of Mozambican Flora

“…D. mespiliformis has been one of the best-studied Mozambican Diospyros species, having NQs identified in different plant parts [4,79] and triterpenoids in leaf, bark, and stem bark [4,76,82].…”

“…Lupeol isolated from D. mespiliformis stem bark has shown analgesic activity in both pain inhibition (neurological-first phase) and origin (inflammatory-second phase) in biphasic tests (in vivo) [76].…”