Determination of catechin diastereomers from the leaves of Byrsonima species using chiral HPLC‐PAD‐CD

Abstract

When catechins are found in plant extracts, they are almost always identified as catechin and/or epicatechin probably due to stereoselectivity of the enzymes involved in the biosynthesis of these substances. However, the lack of reports regarding to ent-catechin as well as ent-epicatechin does not necessarily mean that these compounds have not been produced. In fact, most of the previous reports used chromatographic conditions not suitable for such separation. This article describes a simple and reliable analytical HPLC-PAD-CD method for simultaneous determination of catechin diastereomers both in infusions and extracts from the leaves of Byrsonima species. The direct separation of catechin, ent-catechin, epicatechin, and ent-epicatechin was obtained in normal phase by HPLC-PAD-CD using Chiralcel OD-H as chiral stationary phase and n-hexane/ethanol with 0.1% of TFA as mobile phase.

Byrsonima intermedia A. Juss.: Gastric and duodenal anti-ulcer, antimicrobial and antidiarrheal effects in experimental rodent models

“…In addition to the monomeric flavan-3-ols found in MBI, oligomeric proanthocyanidins were suggested as the broad unresolved peak that eluted in the R t range of 35-60 min. This result is in accordance with those obtained by Rinaldo et al (2010), who compared the methanolic extract and infusible form from the leaves of Byrsonima intermedia. The extraction with methanol instead of water did not show any selectivity in the extraction process; however, the concentration of (+)-catechin and (−)-epicathechin was lower in the infusible form.…”

Mutagenicity and antimutagenicity of six Brazilian Byrsonima species assessed by the Ames test

“…They are popularly known as “murici-vermelho” or “murici-cascudo” and grow wild in the cerrado (savannah-like) vegetation of Brazil. Byrsonima species have been scientifically proven to possess several pharmacological properties, such as antiulcerogenic, mutagenic and antimicrobial activity [14]. …”

“…Rinaldo et al [14] demonstrated that in MeOH extracts and aqueous infusions from the leaves of five Byrsonima species, only in B. coccolobifolia was it not possible to observe the presence of catechins and epicatechins. In the other four species analyzed, it was found that the MeOH extracts showed larger amounts of catechins than the infusions, per gram of leaves.…”

Strategies in the Analysis of Plant Flavonoids

“…In those cases, separation of enantiomer or diastereoisomer compounds can be accomplished using chiral stationary phases (CSPs) or the addition of chiral additives to the mobile phase on conventional stationary phases. CSPs have been mainly used for the enantiomeric separation of flavanones (Yañez et al, 2007), although chiral HPLC has been also applied for the separation of catechin diastereomers (Rinaldo et al, 2010) or taxifolin enantiomers (Vega-Villa et al, 2009). Chiral additives have been used to separate flavonoid enantiomers mainly by capillary electrophoresis (Cao, Qu, and Cheng, 2010;Kwon and Jung, 2011).…”