Chemical Constituents of Ximenia Americana

Abstract

Two steroids (1 and 2), five pentacyclic triperpenoids (3-7) and a new furanosesquiterpene (8) were isolated from the stems of Ximenia americana, family Olacaceae. The structures of the compounds were established by spectral data; two-dimensional NMR spectroscopy has been used to assign all 1 H and 13 C chemical shifts of 8. Compound 8 did not inhibit the growth of HL-60 (human leukemia), HTC-8 (human colon), and MDA-MB-435 (human breast cancer) cell lines.

Ximenia americana L.: Chemical Characterization and Gastroprotective Effect

“…2019) characterized the chromatographic profile (by high-performance liquid chromatography-HPLC) of the same extract, revealing the presence of the compounds quercitrin and caffeic acid as major components, in addition to several others, such as quercetin, rutin, gallic acid, catechin, chlorogenic acid, ellagic acid, and kaempferol [31,32]. A similar chemical composition was observed in other studies, indicating low chemical variation among the samples [14,15].…”

“…The chemical composition of the ethanolic extract of X. americana bark (EHXA) was determined using qualitative and quantitative analyses. Qualitative analysis revealed the presence of various metabolite classes, including phenols, anthocyanins, anthocyanidins, flavonols, chalcones, aurones, leucoanthocyanidin, catechins, and steroids [15,31]. In previous research, our group reported the quantitative chemical profile of polyphenols in EHXA using the HPLC-DAD method, which identified significant compounds such as caffeic acid and quercitrin, as well as other phenolic derivatives, including gallic acid, chlorogenic acid, ellagic acid, and flavonoids such as catechin, rutin, quercetin, and kaempferol [31,32].…”

“…According to a previously published study, the HPLC analysis of Ximenia americana fruit pulp extract identified various phenolic compounds, including rutin, gallic acid, catechin, epicatechin, p-coumaric acid, and ferulic acid [29]. The ethanolic extract obtained from the stems of Ximenia americana was found to contain steroids such as stigmasterol and sitosterol, as well as triterpenoids such as betulinic acid, oleanolic acid, 28-O-(-D-glucopyranosyl) oleanolic acid, 3-oxo-oleanolic acid, 3βhydroxycicloart-24(E)-ene-26-oic acid, and furanoic and widdrane sesquiterpenoids [15,33,34]. Another study also reported the identification of several flavonoids, such as quercetin, kaempferol, and isorhamnetin, in the leaves and fruits.…”

“…The chemical composition of Ximenia americana is diverse and includes flavonoids, triterpenoids, sterols, and fatty acids. Some significant components identified in this species are lupeol, betulinic acid, β-sitosterol, stigmasterol, campesterol, procyanidin, and quercetin [15][16][17]. Lupeol is a triterpenoid reported to have anti-inflammatory and analgesic effects [18].…”

“…Literature data have indicated that betulinic acid presents anti-inflammatory, antioxidant, and antitumor properties [19]. At the same time, β-sitosterol, stigmasterol, and campesterol are phytosterols reported with anti-inflammatory and analgesic effects [20,21] rocyanidin is a polyphenolic polymer with gastroprotective, antioxidant, anticancer, antitumor, antiinflammatory, and immunosuppressive [14][15][16][17][18][19][20][21][22] and quercetin presents anti-inflammatory, antioxidant, and antimicrobial properties [23]. Evidence has shown that the biological activity of these compounds, especially flavonoids and triterpenoids, may be due to their ability to inhibit pro-inflammatory cytokines and prostaglandins [24,25] protecting cells from oxidative damage and reducing inflammation [14].…”