Isolation and identification of oligomeric procyanidins from Crataegus leaves and flowers

Svedström, Ulla; Vuorela, Heikki; Kostiainen, Risto; Tuominen, Jari; Kokkonen, Juha; Rauha, Jussi-Pekka; Laakso, Into; Hiltunen, R.

doi:10.1016/s0031-9422(02)00172-3

Cited by 48 publications

(31 citation statements)

References 10 publications

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“…major NE Br., and were identified by electrospray ionization-mass spectrometry (ESI-MS) and the thiolysis method. 15,16) The vitexinglucoside used for peak identification was isolated from the leaves of C. pinnatifida Bge. var.…”

Section: Methodsmentioning

confidence: 99%

Polyphenolic Content and Physiological Activities of Chinese Hawthorn Extracts

Cui

Nakamura

Tian

et al. 2006

Bioscience, Biotechnology, and Biochemistry

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Hawthorn polyphenol (HP) was prepared by ethyl acetate treatment of the ethanol extract (HE) of Chinese hawthorn fruit. The concentrations of 15 polyphenols in the HP, HE, extraction residue (HJ), and a hawthorn leaf extract (HF) were determined by HPLC. For HP, the total content of the 15 polyphenols was 21.4%, comprised of 19.7% of procyanidins, 1.21% of chlorogenic acid, and 0.48% of flavonoids, compared to 2.55% for the HE. The yields of procyanidin monomer, dimer, trimer, tetramer, and pentamer were 50.5%, 30.3%, 23.0%, 14.6%, and 12.5% respectively, and the mean degree of polymerization was reduced to 1.39 (HP) from 1.65 (HE). Seven different physiological actions of the four extracts were investigated. The HP showed strong O 2 À and OH scavenging capacities (IC 50 values of 6.3 g/ml and 1.1 g/ml respectively), as well as selective prolyl endopeptidase inhibition (IC 50 of 60 g/ml). The active constituents appeared to be procyanidins.Key words: Crataegus pinnatifida; HPLC; procyanidin; antioxidant; free radicalsIn Europe, standardized extracts of the leaves and flowers of Crataegus oxyacantha and Crataegus monogyna are used in the therapy for moderate (NYHA II) congestive heart failure. 1,2) These extracts exert several pharmacological and clinical effects, such as antiischemia/reperfusion-injury, anti-arrhythmic, hypolipidemic, and hypotensive effects. 1,2) Flavonoids and procyanidins are considered to be the two main active constituents. 2) Species of Chinese hawthorn, particularly Crataegus pinnatifida and Crataegus pinnatifida Bge. var. major NE Br., have also been used as herbal medicines. 2,3) Studies indicate that Chinese hawthorn extracts have beneficial effects, such as antioxidant, 4,5) anti-inflammatory, 6) and hypolipidemic effects, 7) as well as protective effects on the brain and vascular endothelium 8,9) and endothelium-dependent relaxation. 10) Recently, we analyzed 37 major cultivars of Chinese hawthorn using high performance liquid chromatography (HPLC), and found that procyanidins, which were present in high concentrations, were the main phenolic active constituents in these fruits. 11) In general, the hawthorn found in China is an edible fruit that is popular for its special acidic taste. It is bigger than its European counterpart. Since the content of organic acid in Chinese hawthorn fruits can be up to 5% (fresh weight), they are used to produce various foods, such as jams, jellies, juices, tinned foods, wines, and various sweet foods. However, the high sugar content of these fruits counteracts the benefits of polyphenols for consumers of advanced age or for those who suffer from hypertension, cardiovascular disease, or diabetes. Hence, it is desirable to separate the polyphenol and sugar components. Previously, hawthorn extract (HE) for medical applications were ethanol-extracted from the dried fruit of the Chinese hawthorn. 12) These crude extracts contain many undesirable substances, such as carbohydrates, organic acids, and moisture, which not only reduce the concentration of acti...

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Section: Methodsmentioning

confidence: 99%

Polyphenolic Content and Physiological Activities of Chinese Hawthorn Extracts

Cui

Nakamura

Tian

et al. 2006

Bioscience, Biotechnology, and Biochemistry

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“…The polymers are a series of compounds where these three compounds are polymerized [26]. Dimers include proanthocyanidin A2 (42), procyanidin B2, B4, B5 (43)(44)(45), and trimers include procyanidin C1 (46), procyanidin D1 (47) …”

Section: Flavanols and The Polymers Of Flavanolsmentioning

confidence: 99%

Crataegus pinnatifida: Chemical Constituents, Pharmacology, and Potential Applications

et al. 2014

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Abstract:Crataegus pinnatifida (Hawthorn) is widely distributed in China and has a long history of use as a traditional medicine. The fruit of C. pinnatifida has been used for the treatment of cardiodynia, hernia, dyspepsia, postpartum blood stasis, and hemafecia and thus increasing interest in this plant has emerged in recent years. Between 1966 and 2013, numerous articles have been published on the chemical constituents, pharmacology or pharmacologic effects and toxicology of C. pinnatifida. To review the pharmacologic advances and to discuss the potential perspective for future investigation, we have summarized the main literature findings of these publications. So far, over 150 compounds including flavonoids, triterpenoids, steroids, monoterpenoids, sesquiterpenoids, lignans, hydroxycinnamic acids, organic acids and nitrogen-containing compounds have been isolated and identified from C. pinnatifida. It has been found that these constituents and extracts of C. pinnatifida have broad pharmacological effects with low toxicity on, for example, the cardiovascular, digestive, and endocrine systems, and pathogenic microorganisms, supporting the view that C. pinnatifida has favorable therapeutic effects. Thus, although C. pinnatifida has already been widely used as pharmacological therapy, due to its various active compounds, further research is warranted to develop new drugs.

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“…Dried flowers, leaves and fruits are mainly used for mild to moderately severe heart failure and coronary heart diseases. Oligomeric procyanidins and (-)-epicatechin as well as flavonoids are known as the main active constituents (Svedström et al, 2002;Sözer et al, 2006). C. laevigata flowers and leaves methanolic water extract led to the isolation of procyanidins.…”

Section: Flavonoidsmentioning

confidence: 99%

“…Epicatechin dimmers; epicatechin-(4 →8)-epicatechin (procyanidin B-2); catechin-(4 →8)-epicatechin (procyanidin B-4); epicatechin-(4 →6)-epicatechin (procyanidin B-5) were obtained from the 43-75 and 117-121 fractions by column chromatography on Sephadex LH-20 uaing EtOH as eluents. Fractions 123-140 was separated with EtOH on Sephadex LH-20 to yield procyanidin trimers, epicatechin-(4 →8)-epicatechin-(4 →8)-epicatechin (procyanidin C-1); epicatechin-(4 →6)-epicatechin-(4 →8)-epicatechin and tetramer epicatechin-(4 →8)-epicatechin-(4 →8)-epicatechin-(4 →8)-epicatechin (procyanidin D-1) (Svedström et al, 2002). Many flavonoids such as hyperoside, rutin, and quercetin have also been isolated from Crataegus species.…”

Section: Flavonoidsmentioning

confidence: 99%