New Sulphated Flavonoids from Wissadula periplocifolia (L.) C. Presl (Malvaceae)

Abstract

Wissadula periplocifolia (L.) C. Presl (Malvaceae) is commonly used in Brazil to treat bee stings and as an antiseptic. The antioxidant properties of its extracts have been previously demonstrated, thus justifying a phytochemical investigation for its bioactive phenolic constituents. This has yielded five new sulphated flavonoids: 8-O-sulphate isoscutellarein (yannin) (1a); 4 1 -O-methyl-7-O-sulphate isoscutellarein (beltraonin) (1b); 7-O-sulphate acacetin (wissadulin) (2a); 4 1 -O-methyl-8-O-sulphate isoscutellarein (caicoine) (2b) and 3 1 -O-methyl-8-O-sulphate hypolaetin (pedroin) (3b) along with the known flavonoids 7,4 1 -di-O-methyl-8-O-sulphate isoscutellarein (4), acacetin, apigenin, isoscutellarein, 4 1 -O-methyl isoscutellarein, 7,4 1 -di-O-methylisoscutellarein, astragalin and tiliroside. The compounds were isolated by column chromatography and identified by NMR ( 1 H, 13 C, HMQC, HMBC and COSY) and LC-HRMS. A cell based assay was carried out to evaluate the preliminary cytotoxic properties of the flavonoids against UVW glioma and PC-3M prostate cancer cells as well as non-tumour cell lines. The obtained results showed that acacetin, tiliroside, a mixture of acacetin + apigenin and the sulphated flavonoids 2a + 2b exhibited inhibitory activity against at least one of the cell lines tested. Among the tested flavonoids acacetin and tiliroside showed lower IC 50 values, presenting promising antitumor effects.

Structural characterization of bioactive compounds in Cotula cinerea extracts by ultra‐high‐performance liquid chromatography with photodiode array and high‐resolution time‐of‐flight mass spectrometry detectors

“…From a taxonomic point of view, the presence of sulfated flavonoids in Cotula cinerea is in agreement with the fact that sulfated flavonoids are less common flavonoid derivatives found in some specific plant families such as Asteraceae to which Cotula cinereal belongs . Our findings are also in agreement with the fact that flavonoid sulfates were also reported to occur in species occurring in arid habitats such as the Moroccan Sahara region from which the studied Cotula cinerea sample was collected.…”

“…From a pharmacological point of view, research into sulfated flavonoids has shed light on their anticoagulant, anti‐inflammatory and antitumor activities . Compared with other flavonoids, sulfated derivatives are more readily soluble in water.…”

Isolation and Identification of Flavonoids Found in <i>Zostera marina</i> Collected in Norwegian Coastal Waters

“…In addition, traces of six flavones (10)(11)(12)(13)(14)(15) were found during HRLC-MS examinations of the extracts. Five of these flavones (1, 2, 4, 7, 8) were substituted with sulphate groups, and the order of retention times in the HPLC reversed phase column system was found to be: disulphate (1) < monoglucoside (3) < monosulphate (4) < acyl glucoside (5) < aglycone (9), here exemplified with luteolin derivatives.…”

Anti-Prostate Cancer Activity of Plant-Derived Bioactive Compounds: a Review

“…Five novel sulfate flavonoids, yannin, beltraonin, wissadulin, caicoine, and pedroin, were isolated from extracts derived from the aerial parts of Wissadula periplocifolia. This extract was both cytotoxic and anti-proliferative to PC-3 cells [36]. On the other hand, extracts derived from the leaves of Hibiscus sabdariffa, which contains mainly polyphenols, exhibited anti-invasive and antimetastatic activity in LNCaP cells via the Akt/NF-kB/MMP-9 cascade pathway [35].…”

“…Some members of this family, including Theobroma cacao from which chocolate is made, are prized cash crops. The phytochemicals identified in members of this family include flavonoids and polyphenols, both of which have been shown to have anticancer and antiinflammatory properties [16,35,36]. Five novel sulfate flavonoids, yannin, beltraonin, wissadulin, caicoine, and pedroin, were isolated from extracts derived from the aerial parts of Wissadula periplocifolia.…”