Phenylpropanoid-substituted Procyanidins and Tentatively Identified Procyanidin Glycosides from Hawthorn (Crataegus spp.)

Abstract

The rational use of hawthorn leafs and flowers from Crataegus spp. for declining cardiac performance is mainly due to flavon-C-glycosides and oligomeric procyanidins (OPC). From OPC-enriched extracts from different batches, a dimeric phenylpropanoid-substituted procyanidin (cinchonain II?b, 1) was isolated and characterized by MS, CD, and NMR. Also the presence of higher oligomeric cinchonains (degree of polymerization 3 to 8) in hawthorn extracts was shown by a specific ultrahigh-pressure liquid chromatography-ESI-qTOF-MS method. Interestingly, strong evidence for the occurrence of oligomeric procyanidin hexosides was found by ultrahigh-pressure liquid chromatography-ESI-qTOF-MS analysis which additionally revealed the presence of peaks indicative of dimeric procyanidin hexosides by their exact mass, which were clearly distinguishable from the cinchonain II type peaks.

Bioassay-Guided Fractionation of a Leaf Extract from Combretum mucronatum with Anthelmintic Activity: Oligomeric Procyanidins as the Active Principle

“…As observed in previous studies, the H 2 O partition obtained from the hydroalcoholic extract was expected to contain proanthocyanidins of higher molecular weight [17,23] and the molecular size of OPCs has been reported to be one major factor responsible for the bioactivity of condensed tannins in general [40] as well as for their anthelmintic activity [41,42]. Therefore, the MeOH-soluble subfraction of the H 2 O partition was further fractionated by MPLC despite its limited activity against C. elegans to yield OPC clusters with distinct DPs from 3 to 10 and a polymeric fraction (Figure 4).…”

“…TLC analysis of fraction XII, obtained from the FCPC stationary phase indicated the presence of a variety of OPCs. From this fraction OPC clusters with defined DP from 3 to 6 were isolated on a preparative scale in good yields by HPLC on a diol stationary phase [20,21,22,23].…”

“…Subsequently, H3 was fractionated by preparative HPLC using a diol stationary phase for separation of distinct OPC clusters with defined DP [20,21,22,23]. This protocol yielded procyanidin clusters from DP2 to DP10 and a polymer fraction in good yields (Figure 1).…”

Crataegus Extract WS®1442 Stimulates Cardiomyogenesis and Angiogenesis From Stem Cells: A Possible New Pharmacology for Hawthorn?

“…They were inactive in the cardiogenic assay ( Figure 2C ). Following the hypothesis that OPCs could account for the cardiogenic activity, defined OPC clusters were isolated from hawthorn as described previously, followed by systematic functional evaluation (Sendker et al, 2009; Zumdick et al, 2009). OPCs with an average DP of 7 or higher exhibited cardiogenic activity, although to a much lower extent (ca.…”

Analysis of γ-Aminobutyric Acid Content in Fermented Plant Products by HPLC/UV

“…C. pinnatifida has been widely used as a medicinal and food material in China and the European countries (Fong and Bauman, 2002). To date, more than 160 compounds have been isolated from C. pinnatifida, including flavonoids, terpenes, lignans, and organic acids (Ahn et al, 1998;Edwards et al, 2012;Song et al, 2012a;Huang et al, 2013;Liu et al, 2013;Sendker et al, 2013). The leaves of C. pinnatifida are widely used for heart problem, such as declining cardiac performance, deficiency in coronary blood supply, and mild forms of arrhythmia (Pöpping et al, 1995;Al Makdessi et al, 1996).…”