Definitive evidence of the presence of 24-methylenecycloartanyl ferulate and 24-methylenecycloartanyl caffeate in barley

Abstract

γ-Oryzanol (OZ), which has a lot of beneficial effects, is a mixture of ferulic acid esters of triterpene alcohols (i.e., triterpene alcohol type of OZ (TTA-OZ)) and ferulic acid esters of plant sterols (i.e., plant sterol type of OZ (PS-OZ)). Although it has been reported that OZ is found in several kinds of cereal typified by rice, TTA-OZ (e.g., 24-methylenecycloartanyl ferulate (24MCA-FA)) has been believed to be characteristic to rice and has not been found in other cereals. In this study, we isolated a compound considered as a TTA-OZ (i.e., 24MCA-FA) from barley and determined the chemical structure using by HPLC-UV-MS, high-resolution MS, and NMR. Based on these results, we proved for the first time that barley certainly contains 24MCA-FA (i.e., TTA-OZ). During the isolation and purification of 24MCA-FA from barley, we found the prospect that a compound with similar properties to OZ (compound-X) might exist. To confirm this finding, the compound-X was also isolated, determined the chemical structure, and identified as a caffeic acid ester of 24-methylenecycloartanol (24MCA-CA), which has rarely been reported before. We also quantified these compounds in various species of barley cultivars and found for the first time the existence of 24MCA-FA and 24MCA-CA in various barley. Through these findings, it opens the possibility to use barley as a new source of 24MCA-FA and 24MCA-CA.

African derived phytocompounds may interfere with SARS-CoV-2 RNA capping machinery via inhibition of 2′-O-ribose methyltransferase: An in silico perspective

“…24-Methylene cycloartenol ferulate, also called γ-Oryzanol (OZ) has been identified in various cereals, including barley, rice bran and corn [57] . It has been reported to exhibit antioxidant, anti-lipidemic, anti-diabetic and neuro-modulatory properties [ 57 , 58 ]. These LPs interacted with the surface residues (Lys-46, Asp-130, Lys-170 and Glu-203) at the bottom of the central groove, thatcatalysis the transfer SAM methyl group within the substrate binding pocket [46] .…”

Gamma-oryzanol jako przykład kompleksu estrów fitosteroli i kwasu ferulowego o szerokiej aktywności biologicznej

“…Późniejsze analizy dowiodły, że gamma-oryzanol stanowi wielozwiązkową mieszaninę głównie zestryfikowanych form kwasu ferulowego [2]. Ustalono, że estry kwasu ferulowego i steroli roślinnych stanowią, obok estryfikowanych kwasem ferulowym triterpenów, jedną z dwóch głównych frakcji gamma-oryzanolu [10]. Motywacją do wnikliwej analizy składu chemicznego tej mieszaniny było powiązanie właściwości chemicznych z obserwowanymi korzyściami prozdrowotnymi płynącymi z jej spożywania.…”

Novel Synthesis of Phytosterol Ferulate Using Acidic Ionic Liquids as a Catalyst and Its Hypolipidemic Activity

“…Phytosterols and their derivatives have garnered significant attention for their exceptional cholesterol-lowering properties. − Among these compounds, phytosterol ferulate (PF) stands out as a derivative that combines the biological activities of both phytosterols and ferulic acid. While rice, corn, wheat, oats, barley, and millet are natural sources of PF, their quantity in these grains is relatively low. − Currently, the major natural source of PF is oryzanol derived from rice bran or rice bran oil, but its content is below 25% . Extracting PF from oryzanol is a challenging task due to its structural resemblance to the primary component of oryzanol, triterpenol ferulate.…”