PHYTOCHEMICAL AND BIOLOGICAL STUDIES OF CONSTITUENTS FROM ROOTS OF Salacia crassifolia (CELASTRACEAE)

Abstract

Salacia crassifolia traditionally known as "Bacupari-do-Cerrado" is used to treat kidney problems, and as a healing agent for coughs and malaria. The phytochemical study of the S. crassifolia roots led to the isolation of thirteen compounds: abruslactone-A (1), urs-12-ene-3β,25,30-triol (2), carioprystimerin (3), β-sitosterol (4), pristimerin (5), dispermoquinone (6), netzahualcoyonol (7), 20-hydroxy-20-epi-tingenone (8), 6-oxo-pristimerol (9), 9β,10β-epoxi-3β-hydroxy-1βH,4βH,5βH,7βH,11αH-guaian-12,8β-olide (10), 3-O-β-D-glucosyl-β-sitosterol (11), 4`-O-methylepigalocatechin (12) and cerebroside (13). The chemical structures of 1-13 were determined by IR, 1D/2D NMR together with X-ray diffractometry. Compounds 2 and 10 are herein described for the first time. Extracts of S. crassifolia and compounds 3, 5, 8 and 9 were evaluated on acetylcholinesterase inhibition, in vitro cytotoxic activity and in vivo toxicity tests using Caenorhabditis elegans model. All tested compounds inhibited acetylcholinesterase, and compounds 3, 8 and 9 demonstrated a greater potential when compared to the standard eserine. The tested compounds showed low cytotoxicity against the THP-1, K562 and MDA-MB-231 cancer cell lines. None of the tested compounds and extracts were toxic against C. elegans since the larvae survival rate in L1 stage was higher than 90%.

Attempts to synthesize a trimeric derivative of pristimerin with potential activity against cancer cells

“…Pristimerin is the major metabolite isolated from hexane/ethyl ether extract of Salacia crassifolia roots, being obtained 5 g, equivalent to 10% of the crude extract (Dos Santos et al, 2020).…”

“…The earliest compounds described for this class are celastrol and pristimerin (Figure 1), which have been isolated from Tripterygium wilfordii Hook, Celastrus scandens L. and Pristimera indica (Gunatilaka, 1996). And, in 2020, Dos Santos and collaborators isolated pristimerin from hexane/ethyl ether extract obtained from roots of Salacia crassifolia in a significant amount (5 g), constituting the main compound of this extract (10%) (Dos Santos et al, 2020).…”

“…For this purpose, the pristimerin trimer would be connected to a proper resin and the ability of alkylation would be evaluated in the presence of guanine, for example. Thus, the objective of the present work was to obtain a trimer of pristimerin previously isolated by Dos Santos et al, (2020), in order to evaluate the formation of adduct with a DNA nitrogen base of cancer cells (Figure 4).…”

Attempts to Synthesize a Trimeric Derivative of Pristimerin With Potential Activity Against Cancer Cells

“…The earliest compounds described for this class are celastrol and pristimerin (Figure 1), which have been isolated from Tripterygium wilfordii Hook, Celastrus scandens L. and Pristimera indica (Gunatilaka, 1996). In this study, pristimerin was isolated from the hexane/ethyl ether extract of Salacia crassifolia roots in a significant amount (5 g), constituting the major compound of this extract (10%) (Dos Santos et al, 2020). Source: Author's own.…”

“…In view of the above and the significant amount of isolated pristimerin from Salacia crassifolia G.Don., a plant of the family Celastraceae (Dos Santos et al, 2020), the synthetic route shown in Figure 4 was proposed to obtain a trimer of pristimerin. The units of pristimerin with azidic oligoethyleneglycol spacer would be introduced in the branched trialkyne by means of click chemistry.…”