Triterpene Alcohol and Sterol Ferulates from Rice Bran and Their Anti-inflammatory Effects

Abstract

Six novel feruloyl esters of triterpene alcohols and sterols, viz., two trans-ferulates, cycloeucalenol and 24-methylenecholesterol trans-ferulates, and four cis-ferulates, cycloartenol, 24-methyelenecycloartanol, 24-methylcholesterol, and sitosterol cis-ferulates, besides five known trans-ferulates, cycloartenol (CAR), 24-methylenecycloartanol (24-MCA), 24-methylcholesterol, sitosterol, and stigmastanol trans-ferulates, and one known cis-ferulate, stigmastanol cis-ferulate, were isolated from the methanol extract of edible rice bran. These and eight other synthetic trans- and cis-ferulates of triterpene alcohols and sterols, along with the corresponding free alcohols, were evaluated with respect to their anti-inflammatory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1 microg per ear) in mice. All of the ferulates showed marked inhibitory activity, and their 50% inhibitory dose (ID(50)) was 0. 1-0.8 mg per ear. On the other hand, whereas two free triterpene alcohols, CAR and 24-MCA, showed strong inhibition (ID(50) 0.2-0.3 mg/ear), eight free sterols examined showed weaker activity (ID(50) 0.7-2.7 mg/ear) than their corresponding ferulates.

By-products of Rice Processing: An Overview of Health Benefits and Applications

“…These phytochemicals are α, β, γ, δ-tocopherol, tocotrienols (vitamin E) [56,57] and γ-oryzanol [56,58]. Vitamin E protects the cell membrane by preventing the oxidation of unsaturated fatty acids and by scavenging free radicals [59,60].…”

“…Gamma-oryzanol, is present at 13 to 20 times (w/w) higher content in rice bran compared to total tocopherols and tocotrienols [133] and has been shown to decrease animal serum-cholesterol levels and antiinflammatory activities while inhibiting cholesterol oxidation in vitro [134,58,61].…”

Characterization and anticancer potential of ferulic acid-loaded chitosan nanoparticles against ME-180 human cervical cancer cell lines

“…It is reported to have antioxidant, antimicrobial, anti-inflammatory, cholesterol-lowering and anticancer activities, as well as ability to prevent thrombosis and atherosclerosis (Wilson et al 2007;Akihisa et al 2000;Ou et al 1999;Kayahara et al 1999;Mori et al 1999). Being capable of absorbing UV radiations, FA is finding place as a photoprotective constituent in many skin lotions and sunscreens (Saija et al 2000).…”

Enzymatic processing of pigmented and non pigmented rice bran on changes in oryzanol, polyphenols and antioxidant activity

“…Rice bran obtained from different varieties of pigmented rice and non-pigmented rice have antioxidant compounds such as tocotrienol, tocopherol, oryzanol, sterols, polyphenols, etc., that help in preventing the damage of body tissue and oxidative damage to DNA caused by free radicals (Nagendra Prasad et al 2011). Among these, gamma-oryzanol is not only a potent antioxidant (Xu et al 2001) but also an effective cholesterol lowering (Raghuram et al 1989) and anti-inflammatory agent (Akihisa et al 2000). Min et al (2012) reported that red and purple bran rices had significantly higher total phenolic and flavonoid concentrations and antioxidant capacities than lightcoloured bran or other cereals,and they attribute it to their higher levels of proanthocyanidins and anthocyanins, respectively.…”