Phenolic derivatives and other chemical compounds from Cochlospermum regium

Abstract

This study describes the chemical investigation of the ethyl acetate fraction obtained from the hydroethanolic extract of the xylopodium of Cochlospermum regium (Mart. & Schr.) Pilger, which has been associated with antimicrobial activity. Phytochemical investigation produced seven phenol derivatives: ellagic acid, gallic acid, dihydrokaempferol, dihydrokaempferol-3-O-β-glucopyranoside, dihydrokaempferol-3-O-β-(6"-galloyl)-glucopyranoside, pinoresinol, and excelsin. It also contained two triacylbenzenes, known as cochlospermines A and B. The hydroethanolic extract and its fractions exhibited antimicrobial activity (0.1 mg/mL) against Staphylococcus aureus and Pseudomonas aeruginosa. Gallic acid showed activity against S. aureus. Dihydrokaempferol-3-O-β-(6"-galloyl)-glucopyranoside is reported here for the first time in the literature

<b>Effect of environmental and phenological factors on the antimicrobial activity of <i>Cochlospermum regium</i> (Schrank) Pilg. roots

“…Researchers have already isolated and identified several substances in Cochlospermum regium roots, e.g., dihydrokaempherol-3-O-β-glucopyranoside (Lima, Castro, Mello, Siqueira, & Kassab, 1996;Sólon et al, 2012), β-selinene, (Honda, Brum, Hess, Cruz, & Moretto, 1997), ellagic acid, gallic acid, dihydrokaempherol, dihydrokaempherol-3-O-β-(6"-galloyl)-glucopyranoside, pinoresinol, excelsine, Acta Scientiarum. Agronomy Maringá, v. 38, n. 4, p. 467-473, Oct.-Dec., 2016…”

“…and the triacylbenzenes cochlospermines A and B (Sólon et al, 2012). However, the compound or compounds that underlie the antimicrobial activity described in ethnopharmacological reviews remain unknown.…”

Phenolic profile and antimicrobial activity of different dietary supplements based on Cochlospermum angolensis Welw.

“…The infusion of C. regium roots has been used to treat intestinal, ovarian and uterine inflammation, dermatitis (Pio Corrêa, 1975), ulcers and rheumatoid arthritis (Lewis and Hanson, 1991;Ritto, 1996), being also reported the antimicrobial activity of its hydroethanolic extract and fractions against Staphylococcus aureus and Pseudomonas aeruginosa (Solon et al, 2012). The total aqueous extract of C. tinctorium demonstrated potent antiplasmodial activity (Traoré et al, 2006) and its rhizomes extract revealed hepatoprotective activity in aflatoxin B1 (Dalvi and Sere, 1988) and carbon tetrachloride (CC1 4 ) treated rats, and in primary rat hepatocyte cultures exposed to cytotoxic concentrations of galactosamine or CC1 4 (Diallo and Vanhaelen, 1987).…”

“…According to some reports, the therapeutic purposes of Cochlospermum genus species (mainly hepatoprotective effects) can be explained by the presence of phytochemicals, specially phenolic an polyphenolic compounds, with gallic and ellagic acids and its derivatives as the major compounds (Diallo and Vanhaelen, 1987;Diallo et al, 1992;Solon et al, 2012;Ferreres et al, 2013). In particular, C. tinctorium revealed gallic and ellagic acids, ellegitannins and flavonoids (Diallo and Vanhaelen, 1987;Diallo et al, 1992), while C. regium showed ellagic and gallic acids, dihydrokaempferol,…”

“…glucopyranoside, pinoresinol, excelsin and two triacylbenzenes (cochlospermines A and B) (Solon et al, 2012). Cochlospermum angolensis hydromethanolic extract revealed high levels of methyl ellagic acid and its derivatives with methyl ellagic acid pentoside isomer as the major compound, and the aqueous extract showed high amounts of ellagic acid and its derivatives (Ferreres et al, 2013 SepPak® Vac 3 cc cartridge (Phenomenex), previously activated with methanol followed by water; sugars and more polar substances were removed by passing through 10 mL of water and the purified samples were further eluted with 5 mL of methanol.…”