Chemosystematic value of flavonoids from Crataegus x macrocarpa (Rosaceae) with special emphasis on (R)- and (S)-eriodictyol-7-O-glucuronide and luteolin-7-O-glucuronide

The chemotaxonomic investigation of Crataegus x macrocarpa, a hybrid of C. laevigata and C. rhipidophylla, presents the qualitative and quantitative composition of its flavonoid pattern in relationship to its parent species for the first time. Six flavonoids were identified as vitexin-2'-O-rhamnoside (1), vitexin (2), isovitexin (3), rutin (4), hyperoside (5), and isoquercitrin (6). Furthermore, two flavonoids were isolated from C. x macrocarpa and identified as a diastereoisomeric mixture of (R)- and (S)-eriodictyol-7-O-beta-D-glucuronide (7) and luteolin-7-O-beta-D-glucuronide (8) by means of 1D- and 2D-NMR, MS, and UV experiments. Compounds 7 and 8 were isolated for the first time from Crataegus species. While missing in C. laevigata, their occurrence in C. rhipidophylla additionally emphasizes its chemotaxonomic relationship to C. x macrocarpa.     

Influence of the parasite Viscum cruciatum Sieber on the chemical constituents of Crataegus monogyna Jacq

A phytochemical study of two plant species, Viscum cruciatum Sieber and Crataegus monogyna Jacq., was completed to investigate the influence of the parasite Viscum cruciatum on the host Crataegus monogyna. The study was carried out with two samples and consisted of hexane extracts of the Viscum cruciatum parasitizing on Crataegus monogyna and C monogyna. In these samples ursolic acid, beta-sitosterol and a triterpene fraction were found that contained mainly butyrospermol (3beta-lanost 8, 24-dien, 3-ol), 24-methylene-24-dihydrolanosterol (24-methylene-5alpha-lanost-8-en-3beta-ol), cycloartenol (9beta, 19-cyclo-5alpha, 9beta-lanost-24-en-3beta-ol), beta-amyrin (olean-12-en-3beta-ol) and several aliphatic alcohols identified as the C18 to C30 members of the 1-alkanol homologous series. beta-Amyrin acetate was only isolated from Viscum cruciatum and was not found in Crataegus monogyna.     

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.     

Molecular and morphological characterization of Crataegus L. species (Rosaceae) in southern Syria

The systematics of the genus Crataegus (Rosaceae) have been considered problematic owing to the fact that hybridization, introgression, polyploidy and apomixis may occur in this genus. A study of the Crataegus species from the Arab mountains, Sweida Province, Syria, has been undertaken based on both plastid DNA sequences ( trn L- trn F, psb A- trn H) and morphological data. In the investigated region, three morphologically distinguishable Crataegus species: C. azarolus var. aronia L., C.  ×  sinaica Boiss. ssp. sinaica and C. monogyna var. monogyna Jacq. were investigated. Crataegus azarolus can be clearly distinguished morphologically from C. monogyna by the colour, size and structure of fruits, the number of pyrenes, the flowering and ripening time, the density of thorns, the tree shape and also the leaf shape. According to our morphological data, in Syria, C.  ×  sinaica is variable and could represent a hybrid of C. azarolus  ×  C. monogyna ; the cpDNA sequence analysis showed sequences corresponding to C. monogyna as the plausible mother of the hybrid.  © 2007 The Linnean Society of London, Botanical Journal of the Linnean Society , 2007, 153 , 255–263.     

The genus Crataegus L.: an ecological and molecular study

This study aimed at the indentification of the species and genotypes of the genus Crataegus in Syria and determination of the genetic relationships among them based on the analysis of genomic and chloroplast DNA (cpDNA) using ISSRs and CAPS techniques. Morphological characterization carried out on 49 Crataegus samples collected from different geographical regions of Syria revealed four Crataegus species: C. monogyna, C. sinaica, C. aronia and C. azarolus. In the dendrogram constructed for those samples based on ISSRs (20 primers), all samples that belong to C. monogyna were clustered in one cluster. Samples of the other three species were overlaped in another cluster. Two samples of these were the most distant from all other samples in the dendrogram and were suggested to represent hybrid species or subspecies. When CAPS technique was applied on four Crataegus samples that represent the four suggested species using 22 cpDNA regions and 90 endonucleases, no polymorphism was detected neither in amplification products sizes nor in restriction profiles. The inability of detection of variation in cpDNA among species suggested can be attributed to the low level of evolution of the cpDNA in the genus, and to the possibility that some of these species are either subspecies or hybrids since the cpDNA is inherited through one parent only.     

Taxonomic notes on European taxa of Crataegus (Rosaceae)

In connection with systematic study of European taxa of Crataegus (Rosaceae subfam. Maloideae) lectotypes are designated for Crataegus monogyna f. subdigyna and C. monogyna var. ronnigeri. C. microphylla subsp. malýana is described as a taxon new to science and a key to the recognised taxa of C. microphylla and of the closely related C. rhipidophylla is given.     

The morphological variation of some Crataegus populations (Rosaceae) in Greece and Yugoslavia

Morphological evidence of hybridization and introgression between Crataegus orien–talis Pallas ex M.–Bieb. and C. pycnoloba Boiss. & Heldr. in Boiss. was observed where the two species meet in the montane–subalpine zone of Mt Chelmos, Pelo–ponnisos. C. pycnoloba var. parnassica Diap. is a variant of C. orientalis. Greek and Yugoslavian material of C. monogyna Jacq., C. curvisepala Lindm. and their hybrid is compared with Danish material of the three taxa using the multivariate techniques of discriminant analysis and Wells' distance coefficient. The infraspecific variation of C. monogyna and the correct binary names for C. monogyna x orientalis ( C. x albanica Pojark. versus C. x polyacantha Jan) and C. curvisepala x monogyna (C. x kyrtostyla Fingerh.) are discussed.     

A biometric study of some hybridizing Crataegus populations in Denmark

Crataegus curvisepala Lindm., C. laevigata (Poiret) DC. and C. monogyna Jacq. (Rosaceae) form hybrid complexes in Denmark due to introgression. C. palmstruchii Lindm. seems to be variously introgressed individuals of C. laevigata. C. eremitagensis Raunk., C. raavadensis Raunk. and C. schumacheri Raunk. apparently belong to C. curvisepala x laevigata. The delimitation between C. curvisepala x laevigata and C. laevigata x monogyna is discussed.     

Search for potential Angiotensin Converting Enzyme (ACE)-inhibitors from plants

MeOH extracts, fractions and pure substances from Musanga cecropioides, Cecropia species and Crataegus oxyacantha /C. monogyna were screened by using an in vitro bio-assay based on the inhibition of Angiotensin Converting Enzyme (ACE), as measured from the enzymatic cleavage of the chromophore-fluorophore-labelled substrate dansyltriglycine into dansylglycine and diglycine. Phenolic acids showed no significant ACE-inhibition whereas flavonoids and proanthocyanidins demonstrated inhibitory activity at 0.33 mg/ml using this test system.     

Procyanidins in crataegus extract evoke endothelium-dependent vasorelaxation in rat aorta

The extract of Crataegus, a mixture of flavonoids and procyanidins extracted from hawthorn, Crataegus oxyacantha, L. and C. monogyna Jacq., relaxed vascular tone or increased production of cyclic GMP in the rat aorta, but flavonoid components of Crataegus extract, hyperoside, rutin and vitexin, did not affect the vascular tone. The aim of the present study was to characterize the endothelium-dependent relaxation elicited by procyanidins fractionated from Crataegus extract in isolated rat aorta. Procyanidins caused endothelium-dependent relaxation which was associated with the production of cyclic GMP. Both responses to these procyanidins were inhibited by methylene blue or N(G)-nitro-L-arginine, but not by indomethacin. Relaxation in response to procyanidins was not affected by atropine, diphenhydramine, [D-Pro2,D-Trp7,9]substance P, propranolol, nifedipine, verapamil and glibenclamide, but were markedly reduced by tetraethylammonium. These findings showed that procyanidins in Crataegus extract may be responsible for the endothelium-dependent nitric oxide-mediated relaxation in isolated rat aorta, possibly via activation of tetraethylammonium-sensitive K+ channels.     

野山楂茎化学成分研究

采用硅胶、AB-8大孔树脂和凝胶柱层析方法对野山楂茎化学成分进行分离纯化,并根据理化性质和光谱数据分析鉴定得到9个化合物,分别是:棕榈酸(1)、硬脂酸(2)、β-谷甾醇(3)、槲皮素(4)、芦丁(5)、熊果酸(6),β-胡萝卜甙(7),柠檬酸(8)和儿茶素(9)。除化合物4外,其余均首次从野山楂中分离得到。     

A Garden Experiment on Susceptibility to Rabbit-Grazing, Sapling Growth Rates, and Age at First Reproduction for Eleven European Woody Species

Abstract: Eleven European shrub and tree species have been grown for 13 years in a randomized array (with 2 or 3 provenances for 5 of 11 species) in an experimental garden in southern England. A plague of rabbits in the second year damaged a greater proportion of plants in species with faster height growth, including those that are the commonest colonizers of pastures; most plants recovered rapidly. Apparently, resilience rather than resistance enables these plants to be invaders of abandoned grasslands. Among the shrubs there was little evidence of a trade-off between initial rate of height growth and final height. The small tree Crataegus monogyna overtook the tallest shrub ( Cornus sanguinea ) in the 12th year. Among the shrubs, after 12 years, there was a trend for basal area to be greater in taller species; the trees had notably low basal area for their height. Most individuals of the shrub species reproduced before those of Crataegus and Sorbus aria (in 3–6 years rather than 5–13). Among the shrubs, the earliest to reproduce were fast-growing ( Rosa canina , then Ligustrum vuigare, Prunus spinosa and Rhamnus catharticus ), but then species with a wide range of growth rates all reproduced at the same time ( Euony-mus europaeus, Juniperus communis and Viburnum opulus slow-growing, Cornus sanguinea and V. lantana fast-growing). The results are discussed in relation to theories of resource allocation, and the behaviour of the particular species in the field.     

S-allele diversity in Sorbus aucuparia and Crataegus monogyna (Rosaceae: Maloideae)

RT-PCR was used to obtain the first estimates from natural populations of allelic diversity at the RNase-based gametophytic self-incompatibility locus in the Rosaceae. A total of 20 alleles were retrieved from 20 Sorbus aucuparia individuals, whereas 17 alleles were found in 13 Crataegus monogyna samples. Estimates of population-level allele numbers fall within the range observed in the Solanaceae, the only other family with RNase-based incompatibility for which estimates are available. The nucleotide diversity of S-allele sequences was found to be much lower in the two Rosaceae species as compared with the Solanaceae. This was not due to a lower sequence divergence among most closely related alleles. Rather, it is the depth of the entire genealogy that differs markedly in the two families, with Rosaceae S-alleles exhibiting more recent apparent coalescence. We also investigated patterns of selection at the molecular level by comparing nucleotide diversity at synonymous and nonsynonymous sites. Stabilizing selection was inferred for the 5' region of the molecule, while evidence of diversifying selection was present elsewhere.     

Susceptibility of four hedgerow shrubs to a range of herbicides and plant growth regulators

Crataegus monogyna, Prunus spinosa, Fraxinus excelsior and Sambucus nigra, common woody species of hedgerows, were grown in pots and treated in June with half and full recommended rates of 15 herbicides and three plant growth regulators. C. monogyna was affected by fewest compounds, while the other three species showed differing tolerances. The wild-oat herbicides, diclofop-methyl, flamprop-m-isopropyl and difenzoquat did not adversely affect the shrubs. Plant growth regulators used at rates recommended for cereals and grassland had only minor effects. Clopyralid killed only S. nigra, while mecoprop, fluroxypyr, chlorsulfuron, metsulfuron-methyl and glyphosate caused significant damage to most species. Height of C. monogyna was increased after treatment with diclofop-methyl, difenzoquat, ethofumesate, mefluidide and chlormequat.     

Application of random amplified polymorphic DNA and inter-simple sequence repeat markers in the genus Crataegus

Hawthorn ( Crataegus spp.) has a long history as an ornamental and a source of medicine. We report the use of random amplified polymorphic DNA (RAPD) and inter-simple sequence repeat (ISSR) markers to determine genetic relationships in the genus Crataegus . Twenty-eight accessions, including eight species ( Crataegus pinnatifida , Crataegus bretschneideri , Crataegus maximowiczii , Crataegus kansuensis , Crataegus altaica , Crataegus songarica , Crataegus dahurica and Crataegus sanguinea ) and two botanical varieties ( C. pinnatifida var. major and C. maximowiczii var. ninganensis ) were analysed. Twelve RAPD primers reproducibly and strongly amplified 128 fragments of which 116 were polymorphic; similarly, 13 ISSR primers generated 127 products of which 119 were polymorphic. Dendrograms based on unweighted pair group method with arithmetic average analysis were constructed from both the RAPD and the ISSR data. Similarity coefficient based on RAPD and ISSR markers ranged from 0.22 to 0.98 and 0.23 to 0.98, respectively. The range in similarity coefficient indicated that the genus has a high level of genetic diversity. The Mantel test on the similarity matrices produced by RAPD and ISSR markers gave r  = 0.86, showing high correlation between RAPD and ISSR markers in their ability to detect genetic relationships between Crataegus accessions. RAPD and ISSR appear to be reliable methods for the analysis of genetic relationships among hawthorns.     

Genetic Relationships Among Some Hawthorn (Crataegus spp.) Species and Genotypes

The genus Crataegus is well distributed in Turkey as a wild plant, with numerous, inherently variable species and genotypes. RAPD markers were used to study 17 hawthorn genotypes belonging to Crataegus monogyna ssp. monogyna Jacq (2 genotypes), C. monogyna ssp. azarella Jacq (1), Crataegus pontica K.Koch (3), Crataegus orientalis var. orientalis Pallas Ex Bieb (3), Crataegus pseudoheterophylla Pojark (1), Crataegus aronia var. dentata Browicz (1), C. aronia var. aronia Browicz (4), and Crateagus × bornmuelleri Zabel (2). The 10 RAPD primers produced 72 polymorphic bands (88% polymorphism). A dendrogram based on Jaccard’s index included four major groups and one outgroup according to taxa. The lowest genetic variability was observed within C. aronia var. aronia genotypes. The study demonstrated that RAPD analysis is efficient for genotyping wild-grown hawthorns.     

Dispersal of an introduced shrub (Crataegus monogyna) by the Brush-tailed Possum (Trichosurus vulpecula)

The Brush-tailed possum Trichosurus vulpecula eats the fleshy fruits of the introduced shrub Crataegus monogyna and defaecates intact seeds at least 0–50 m away. Viability of seeds recovered from faeces was >73%. comparable to the viability of fresh seeds (87.6%). Seed dispersal by possums has been largely neglected and may have important implications for invasion by woody weeds in Australasia.     

Applied environmental stresses to enhance the levels of polyphenolics in leaves of hawthorn plants

In this investigation, two species of Crataegus (hawthorn) were chosen because their polyphenolic constituents have recently received greater attention for the treatment of patients with severe heart disease. One-year-old plants of hawthorn ( Crataegus laevigata and C. monogyna ) were subjected to water-deficit (continuous water deprivation), cold (4°C), flooding (immersion of roots of plants in water) or herbivory (leaf removal) stress treatments (each of 10 days duration) in order to assess their effects on levels of polyphenolics, namely (-)-epicatechin, catechin, chlorogenic acid, vitexin, vitexin-2'- O -rhamnoside, acetylvitexin-2'- O -rhamnoside, hyperoside, quercetin, and rutin in the leaves. The working hypothesis followed is that one or more of these stress treatment will elicit increases in the levels of these polyphenolics. Cold stress causes increases in levels of vitexin-2'- O -rhamnoside, acetylvitexin-2'- O -rhamnoside, hyperoside, and quercetin in both Crataegus species. Water-deficit stress increased the productivity of chlorogenic acid, catechin, and (-)-epicatechin in both hawthorn species. Flooding and herbivory caused no net increases, and in some cases, decreases in levels of polyphenolics. These studies indicate that either water-deficit stress or cold stress treatments, or a combination of the two, can be used to enhance the levels of desired polyphenolics in the leaves of these two hawthorn species in a photobioreactor system. These results may have significance for hawthorn in adapting to water-deficit or cold stress and are important considerations for the use of hawthorn in the treatment of heart disease in humans.     

Taxonomic notes on the genus Crataegus (Rosaceae) in Turkey

The Turkish Crataegus taxa were investigated using morphological, palynological, and anatomical characters. A new series ( Crataegus Section Crataegus Series Peshmenia ), two new species ( Crataegus peshmenii and Crataegus christensenii ), and one variety ( Crataegus rhipidophylla var. kutahyaensis ) are described. Furthermore, Crataegus  ×  browicziana has been assigned to Crataegus rhipidophylla with a new status. Illustrations of the described taxa and their distribution map are also given. The lectotype for Crataegus yaltirikii is designated here.  © 2007 The Linnean Society of London, Botanical Journal of the Linnean Society , 2007, 155 , 231–240.     

COMPARATIVE MORPHOLOGY OF THE CARPEL IN THE ROSACEAE. III. POMOIDEAE: CRATAEGUS,HESPEROMELES, MESPILUS,OSTEOMELES

The carpels in Crataegus, Hesperomeles, Mespilus, and Osteomeles appear to constitute a morphologically related group: all have bony pits, ovules that tend to be acollateral (usually superposed), and clearly separate ovular and wing bundles, i.e., no “ventral” bundles, at the level of ovular insertion. In species whose carpels have no sutural opening, the integuments are more extensively fused with one another, the degree of intercarpellary fusion tends to be greater, and the carpels are fused with the floral cup to relatively higher levels than in those species whose carpels have a sutural opening. In the few cases in which wing and ovular bundles are adnate at the locular base (Crataegus monogyna, Mespilus, Osteomeles anthyllidifolia, O. Schwerinae), the extent of inter- and extracarpellary fusion and sutural closure is among the most advanced.