Isolation and identification of oligomeric procyanidins from Crataegus leaves and flowers

Oligomeric procyanidins were isolated from the leaves and flowers of hawthorn (Crataegus laevigata). A trimer, epicatechin-(4β→8)-epicatechin-(4β→6)-epicatechin, and a pentamer consisting of (−)-epicatechin units linked through C-4β/C-8 bonds have been isolated from hawthorn for the first time, in addition to known procyanidins including dimers B-2, B-4 and B-5, trimers C-1 and epicatechin-(4β→6)-epicatechin-(4β→8)-epicatechin, and tetramer D-1. A fraction containing a hexamer was also found.     

不同时期山里红叶片中多元酚类成分含量的测定

The content of polyphenolic compounds including chlorogenic acid, vitexin-4＂-O-glucoside, vitexin rhamnoside, rutin, vitexin, hyperoside in leaf of Crataegus pinnatifida Bunge var. major N. E. Br. at different times was determined by HPLC. The results show that the content of polyphenolic compounds in different times is various. In April, the total content of polyphenolic compounds and the contents of chlorogenic acid, vitexin-4＂-O-glucoside, vitexin rhamnoside, rutin reach the peak. And the content of every compound and the total content of these compounds decrease gradually with the plant growing, and reach the lowest point in July to August. Therefore, in order to extract polyphenolic compounds, the optimal harvest time for C. pinnatifida var. major leaf is April.     

Oral administration of Crataegus flavonoids protects against ischemia/reperfusion brain damage in gerbils

Stroke is the third leading cause of death as dementia is a main symptom of Alzheimer's disease. One of the important mechanisms in the pathogeny of stroke is free radical production during the reperfusion period, therefore the effects of a type of natural antioxidant, i.e. Crataegus flavonoids (CF), on brain ischemic insults were investigated in Mongolian gerbil stroke model. Results showed that pretreatment of the animals with CF decreased reactive oxygen species (ROS) production, thiobarbituric acid reactive substances content, and nitrite/nitrate concentration in brain homogenate, increased the brain homogenate-associated antioxidant level in a dose-dependent manner. CF pretreatment increased the amount of biologically available NO by scavenging of superoxide anion produced during reperfusion. At same time, in the process of ischemia/reperfusion brain damage, the content of nitrite/nitrate (the end product of NO) increased, and of NO detected by ESR decreased. Oral pretreatment with CF decreased the nitrite/nitrate content in the brain homogenate and increased the biologically available NO concentration in a dose-dependent manner. The increasing effect of antioxidant on NO might be due to its scavenging effect on superoxide anion, which could react with NO into peroxynitrite. iNOS was implied in delayed neuron death after brain ischemic damage and it was found that pretreatment with CF could decrease the protein level of tumor necrosis factor (TNF)-alpha and nuclear factor-kappa B (NF-kappaB), and increase the mRNA level of NOS estimated by western blotting and RT-PCR. More neurons survived and fewer cells suffered apoptosis in the hippocampal CA1 region of CF treated animal brain. These results suggest that oral administration of this antioxidant increases the antioxidant level in the brain and protects the brain against delayed cell death caused by ischemia/reperfusion injury.     

山楂属主要植物叶子生药学研究

本文对我国山楂属主要植物的叶子进行了光镜及电镜下组织构造的比较,指出了种间鉴别特征。并对黄桐等成分进行分析,结果表明山楂、山里红、云南山楂、湖北山楂的叶子中含有防治心血管系统疾病的牡荆素、芦丁和金丝桃甙等有效成分,为本属植物的开发利用提供了依据。     

Chemical constituents from the leaves of Crataegus pinnatifida Bge

The phytochemical investigations on the leaves of Crataegus pinnatifida led to the isolation of 20 compounds, including seven triterpenoids (1-7), three hydroxycinnamic acids (8-10), three lignans (11-13) and seven flavonoids (14-20). All chemical structures were established on the basis of NMR (1H NMR, 13C NMR) spectroscopic data. Meanwhile, compounds 3-12 are reported for the first time from Crataegus genus. In addition, compounds 10-11 are isolated from the family Rosaceae for the first time. On the basis of chemical research, the chemotaxonomic significance of the isolated compounds has been discussed.     

Effect of hawthorn (Crataegus oxycantha) crude extract and chromatographic fractions on multiple activities in a cultured cardiomyocyte assay

Extracts of hawthorn (Crataegus oxycantha) have become popular herbal supplements for their well-recognized cardiotonic effects. Many commercial preparations have been used successfully in the treatment of congestive heart failure, although the active principles within these extracts have yet to be conclusively identified. Several hawthorn preparations were studied and found to have negative chronotropic effects in a cultured neonatal murine cardiomyocyte assay using unpaced cells. As compared to conventional cardiac drugs (i.e., epinephrine, milrinone, ouabain, or propranolol), hawthorn extract has a unique activity profile. Hawthorn extract appears to be anti-arrhythmic and capable of inducing rhythmicity in quiescent cardiomyocytes. Hawthorn extract does not cause β-adrenergic receptor blockade at concentrations which cause negative chronotropic effects. Commercial hawthorn preparations, extracts prepared from dried leaves and those made from dried berries have similar chronotropic activities. When crude extracts are separated using size-exclusion chromatography, several fractions retain multiple cardiac activities. Assays with chromatographic fractions reveal that multiple dissimilar cardioactive components may exist within the extract, making the identification of individual active constituents more challenging.     

RECONSTRUCTING RETICULATION HISTORY IN A PHYLOGENETIC FRAMEWORK AND THE POTENTIAL OF ALLOPATRIC SPECIATION DRIVEN BY POLYPLOIDY IN AN AGAMIC COMPLEX IN CRATAEGUS (ROSACEAE)

Polyploidy plays a prominent role in the speciation process in plants. Many species are known to be part of agamic complexes comprising sexual diploids and more or less exclusively asexual polyploids. However, polyploid formation has been studied in very few cases, primarily because of the challenges in examining these cases phylogenetically. In this study, we demonstrate the use of a variety of phylogenetic approaches to unravel origins and infer reticulation history in a diploid–polyploid complex of black‐fruited Crataegus. The tree approaches are shown to be useful in testing alternative hypotheses and in revealing genealogies of nuclear genes, particularly in polyploid organisms that may contain multiple copies. Compared to trees, network approaches provide a better indication of reticulate relationships among recently diverged taxa. Taken together, our data point to both the autopolyploid and allopolyploid origins of triploids in natural populations of Crataegus suksdorfii, whereas tetraploids are formed via a triploid bridge, involving the backcross of allotriploid offspring with their diploid C. suksdorfii parent, followed by gene introgression from sympatric C. douglasii. Our findings provide empirical evidence for different pathways of polyploid formation that are all likely to occur within natural populations and the allopatric establishment of neopolyploids subsequent to their formation.     

Influence of the extraction mode on the yield of hyperoside, vitexin and vitexin-2'-O-rhamnoside from Crataegus monogyna Jacq. (hawthorn)

Introduction –  The extract of Crataegus monogyna shows sedative, hypotensive, vasodilator and cardio‐tonic actions. Although several papers dealing with the extraction of metabolites from Crataegus have been published, the plant productivity in terms of bioactive compounds is not easily understandable as yet. Objective –  To investigate the influence of the extraction mode on the yield of bioactive compounds from Crataegus monogyna Jacq. in order to evaluate plant productivity. Methodology –  Samples were prepared by extraction of powdered material obtained from top branches, flowers and leaves. Soxhlet extraction, maceration and ultrasound‐ and microwave‐assisted extraction at different experimental conditions were investigated for the exhaustive extraction of hyperoside, vitexin and vitexin‐2′′‐O‐rhamnoside. The phytocomponents were identified and quantified by HPLC‐UV/PAD, comparing HPLC retention times and UV spectra of individual peaks with those of the standards analysed under the same conditions. Results –  An easy‐to‐use HPLC isocratic method suitable for the quantification of hyperoside, vitexin and vitexin‐2′′‐O‐rhamnoside in raw plant extracts was developed. The optimised HPLC methodology was applied to evaluate different extraction procedures. The ultrasound and microwave‐assisted extraction protocols showed higher extraction efficiency than the others. In particular, the optimised microwave protocol gave rise to the highest extraction efficiency with high reproducibility. Conclusions –  A microwave protocol combined with isocratic HPLC analysis is proposed for the rapid screening of plant materials collected in different environmental conditions in order to evaluate the productivity of Crataegus monogyna Jacq. and to find out the best ecological conditions to cultivate hawthorn in Northern Italy. Copyright © 2008 John Wiley & Sons, Ltd.     

Intergeneric hybrids between Crataegus L. and Mespilus L.: a fresh look at an old problem

A brief outline is given of the history and nomenclature of the sexual and graft hybrids (chimeras) between Crataegus and Mespilus. An investigation has been made of some aspects of the macromorphology, the pollen fertility and exine characters, cytology and physiology of the plants growing in the Royal Botanic Gardens, Kew. It is suggested that in the past too much emphasis has been laid on the anatomy of the epidermal layers and the separation of parental characters in chimeras. Observations made during the study show the presence of intermediate characters in the graft hybrid as well as in the sexual hybrid and there is evidence that most parts of the graft hybrids are probably influenced by both the parental genotypes.