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1.
J Integr Plant Biol ; 64(8): 1487-1501, 2022 Aug.
Article in English | MEDLINE | ID: mdl-35748532

ABSTRACT

Cultivated hawthorn (Crataegus pinnatifida var. major) is an important medicinal and edible plant with a long history of use for health protection in China. Herein, we provide a de novo chromosome-level genome sequence of the hawthorn cultivar "Qiu Jinxing." We assembled an 823.41 Mb genome encoding 40 571 genes and further anchored the 779.24 Mb sequence into 17 pseudo-chromosomes, which account for 94.64% of the assembled genome. Phylogenomic analyses revealed that cultivated hawthorn diverged from other species within the Maleae (apple tribe) at approximately 35.4 Mya. Notably, genes involved in the flavonoid and triterpenoid biosynthetic pathways have been significantly amplified in the hawthorn genome. In addition, our results indicated that the Maleae share a unique ancient tetraploidization event; however, no recent independent whole-genome duplication event was specifically detected in hawthorn. The amplification of non-specific long terminal repeat retrotransposons contributed the most to the expansion of the hawthorn genome. Furthermore, we identified two paleo-sub-genomes in extant species of Maleae and found that these two sub-genomes showed different rearrangement mechanisms. We also reconstructed the ancestral chromosomes of Rosaceae and discussed two possible paleo-polyploid origin patterns (autopolyploidization or allopolyploidization) of Maleae. Overall, our study provides an improved context for understanding the evolution of Maleae species, and this new high-quality reference genome provides a useful resource for the horticultural improvement of hawthorn.


Subject(s)
Crataegus , Malus , Rosaceae , Crataegus/genetics , Crataegus/metabolism , Fruit/genetics , Phylogeny
2.
Chem Biodivers ; 18(12): e2100705, 2021 Dec.
Article in English | MEDLINE | ID: mdl-34710267

ABSTRACT

Emerging evidence suggests that a high-fat diet (HFD) can influence endoplasmic reticulum (ER) stress and gut microbiota. Crataegi Fructus is a traditional Chinese herb widely used in formulas for dyspepsia, with Dashanzha Pill composed of raw Crataegi Fructus (DR) being a representative drug. Processing products of Crataegi Fructus, however, have a stronger pro-digestive effect, and we hypothesized that Dashanzha Pill composed of charred Crataegi Fructus (DC) is more effective. We found that the contents of glucose 1-phosphate and luteolin in DR and DC were substantially different via ultra-high performance liquid chromatography-hybrid quadrupole-Orbitrap high-resolution mass spectrometry. DC outperformed DR in improving histopathological changes, increasing gastrin and motilin, and decreasing vasoactive intestinal peptides in rats with HFD induced dyspepsia. Fecal microbiota analysis revealed that DC could restore the disturbed intestinal microbiota composition, including that of Bacteroides, Akkermansia, and Intestinimonas to normal levels. Furthermore, DC significantly reduced the mRNA and protein levels of glucose-regulated protein 78, protein kinase R-like ER kinase, and eukaryotic initiation factor 2α. Taken together, DC outperformed DR in relieving dyspepsia by regulating gut microbiota and alleviating ER stress.


Subject(s)
Drugs, Chinese Herbal/pharmacology , Dyspepsia/drug therapy , Fruit/chemistry , Plant Extracts/pharmacology , Animals , Crataegus/chemistry , Crataegus/metabolism , Diet, High-Fat , Drugs, Chinese Herbal/chemistry , Drugs, Chinese Herbal/metabolism , Dyspepsia/chemically induced , Endoplasmic Reticulum Stress/drug effects , Gastrointestinal Microbiome/drug effects , Male , Medicine, Chinese Traditional , Plant Extracts/chemistry , Plant Extracts/metabolism , Rats , Rats, Sprague-Dawley
3.
Molecules ; 26(9)2021 May 01.
Article in English | MEDLINE | ID: mdl-34062758

ABSTRACT

Crataegus contains numerous health-promoting compounds that are also proposed to have anti-cancer properties. Herein, we aimed at a contemporaneous evaluation of the effects of polyphenol-rich extracts of berries, leaves, and flowers of six Crataegus species on the viability and invasive potential on the highly aggressive human glioblastoma U87MG cell line. The treatment with the extracts evoked cytotoxic effects, with the strongest in the berry extracts. All extracts not only promoted the apoptosis-related cleavage of poly (ADP-ribose) polymerase 1 (PARP1) but also substantially inhibited the activity of pro-survival kinases, focal adhesion kinase (FAK), and protein kinase B (PKB; also known as Akt), thus indicating the suppression of proliferative and invasive potentials of the examined glioblastoma cells. The qualitative and quantitative characterization of the extracts' content was also performed and revealed that amongst 37 polyphenolic compounds identified in the examined Crataegus extracts, the majority (29) was detected in berries; the leaf and flower extracts, exerting milder cytotoxic effects, contained only 14 and 13 compounds, respectively. The highest polyphenol content was found in the berries of C. laevigata x rhipidophylla x monogyna, in which flavan-3-ols and phenolic acids predominated. Our results demonstrated that a high content of polyphenolic compounds correlated with the extract cytotoxicity, and especially berries were a valuable source of compounds with anti-cancer potential. This might be a promising option for the development of an effective therapeutic strategy against highly malignant glioblastomas in the future.


Subject(s)
Brain Neoplasms/drug therapy , Crataegus/metabolism , Flowers/metabolism , Glioblastoma/drug therapy , Plant Extracts/pharmacology , Plant Leaves/metabolism , Polyphenols/chemistry , Actin Cytoskeleton/metabolism , Apoptosis , Cell Line, Tumor , Cell Survival , Humans , Hydroxybenzoates/chemistry , Microscopy, Confocal , Neoplasm Invasiveness , Neoplasms/metabolism
4.
Chem Biodivers ; 17(2): e1900609, 2020 Feb.
Article in English | MEDLINE | ID: mdl-31916412

ABSTRACT

The fruit of Crataegus dahurica Koehne was used to treat the disease of infantile indigestion and dyspepsia as an ethnic medicine and food. As a continuous work on finding the active constituents from the edible herbs, four new biphenyl derivatives (1-4), together with two known compounds (5 and 6), were obtained from the petroleum ether fraction of the fruits of C. dahurica. Their structures were determined by the extensive 1D and 2D NMR spectra and HR-MS spectrometry. Furthermore, the anti-inflammatory activities of all the isolated compounds were investigated, in which compound 4 showed moderately inhibitory effects on NO production in RAW264.7 cells without inducing cytotoxicity.


Subject(s)
Anti-Inflammatory Agents/chemistry , Crataegus/chemistry , Animals , Anti-Inflammatory Agents/isolation & purification , Anti-Inflammatory Agents/pharmacology , Biphenyl Compounds/chemistry , Biphenyl Compounds/isolation & purification , Biphenyl Compounds/pharmacology , Cell Survival/drug effects , Crataegus/metabolism , Fruit/chemistry , Fruit/metabolism , Lipopolysaccharides/toxicity , Macrophages/cytology , Macrophages/drug effects , Macrophages/metabolism , Magnetic Resonance Spectroscopy , Mice , Molecular Conformation , Nitric Oxide/metabolism , RAW 264.7 Cells
5.
J Sci Food Agric ; 100(5): 1998-2006, 2020 Mar 30.
Article in English | MEDLINE | ID: mdl-31849067

ABSTRACT

BACKGROUND: In this investigation, the chemical and biological profiles of three Turkish Crataegus species (Crataegus orientalis, Crataegus szovitsii and Crataegus tanacetifolia) were studied in order to provide the first comprehensive characterization and their health-promoting potential. In this respect, polyphenolic profiles were evaluated using ultrahigh-performance liquid chromatography-quadrupole time-of-flight mass spectrometry. The in vitro antioxidant activities of the Crataegus samples were evaluated by using free-radical scavenging, phosphomolybdenum, ferrous-ion chelating, and reducing power assays. The inhibitory activities against α-glucosidase, amylase, cholinesterases (acetylcholinesterase (AChE) and butyrylcholinesterase (BChE)), and tyrosinase were also established. RESULTS: The untargeted metabolomic approach highlighted the effect of both extraction types and species on the phenolic profiles of different Crateagus tissues (i.e. leaves and twigs). The methanolic extracts showed the maximum radical scavenging and reducing activity in all test systems, whereas for ferrous-ion chelating assays the decocted and infused extracts showed the highest activity. Only the methanolic extracts were effective against AChE and BChE. The extract tested showed remarkable inhibitory effects against tyrosinase and α-glucosidase, whereas all the extracts exhibited modest inhibition against α-amylase. Overall, the twig extracts of the three species studied showed superior antioxidant and enzyme inhibitory activities. CONCLUSION: On the basis of these results, the three Crataegus species can be classified as potent bioresources for high-value phytochemicals, which warrant further investigations for developing novel nutraceuticals. © 2019 Society of Chemical Industry.


Subject(s)
Crataegus/chemistry , Enzyme Inhibitors/chemistry , Plant Extracts/chemistry , Antioxidants/metabolism , Butyrylcholinesterase/chemistry , Crataegus/metabolism , Enzyme Inhibitors/metabolism , Metabolomics , Monophenol Monooxygenase/antagonists & inhibitors , Monophenol Monooxygenase/chemistry , Phenols/chemistry , Phenols/metabolism , Plant Extracts/metabolism , Turkey , alpha-Amylases/antagonists & inhibitors , alpha-Amylases/chemistry , alpha-Glucosidases/chemistry
6.
Anal Bioanal Chem ; 411(10): 2149-2159, 2019 Apr.
Article in English | MEDLINE | ID: mdl-30848317

ABSTRACT

Crataegus products for food, nutritional, and pharmaceutical uses are available over the counter in the global market. The aerial parts are enriched with biochemicals and are used to treat cardiovascular, respiratory, and liver disorders and cancer. Detailed study to understand the chemical composition and different levels within medicinally important plant tissues needs hours, such as plant response for metabolite flux and quality control purposes. Therefore, comprehensive metabolite profiling (qualitatively and quantitatively) of different tissues [leaves, flowers, stems, fruits (without seeds), and seeds; n = 5] of Crataegus rhipidophylla Gand. was performed by NMR techniques in one session. Fifty-eight compounds of different classes were unambiguously identified with the use of 1D and 2D NMR techniques (1H, 13C, distortionless enhancement by polarization transfer with 135° angle, correlation spectroscopy, heteronuclear single quantum coherence, heteronuclear multiple bond correlation) and quantified by a relative quantification method. Chemical compounds such as amygdalin (seeds), rutin (flowers), isovitexin (fruits), shikimic acid (leaves), and epicatechin (stems) were identified as authentication as well as discrimination markers for the respective C. rhipidophylla tissues. The fruits contain a significant mixture of important metabolites, followed by flowers and leaves. Trends of metabolite levels, upregulation, and downregulation in plant tissues were found, which highlights the responses of plant tissues in a specific time. NMR-based comprehensive metabolite information was used to develop the chemical signature, quality control chemical markers, and strategies to understand the chemical diversity of C. rhipidophylla. This chemical information from different aerial tissues will provide guidance for the extensive utilization of Crataegus.


Subject(s)
Crataegus/metabolism , Magnetic Resonance Spectroscopy/methods , Metabolome , Metabolomics/methods , Plant Extracts/metabolism , Amino Acids/analysis , Amino Acids/metabolism , Carbohydrate Metabolism , Carbohydrates/analysis , Crataegus/chemistry , Flavonoids/analysis , Flavonoids/metabolism , Flowers/chemistry , Flowers/metabolism , Fruit/chemistry , Fruit/metabolism , Hydroxybenzoates/analysis , Hydroxybenzoates/metabolism , Plant Extracts/chemistry , Plant Leaves/chemistry , Plant Leaves/metabolism , Seeds/chemistry , Seeds/metabolism , Terpenes/analysis , Terpenes/metabolism
7.
J Chem Ecol ; 44(7-8): 671-680, 2018 Aug.
Article in English | MEDLINE | ID: mdl-29923080

ABSTRACT

A new blend of volatiles was identified for the fruit of downy red hawthorn, Crataegus mollis, that is attractive to Rhagoletis pomonella flies infesting this host in the northeastern USA. The new blend was as attractive as the previously identified mixture but is more complex in the number of odorants (six in the old versus ten in the new) and differs significantly in the ratio of three volatiles, 3-methylbutan-1-ol, butyl hexanoate, and dihydro-ß-ionone, that are common to both blends and exerted agonist or antagonist effects on behavior in a flight tunnel assay. However, behavioral results with the old and new northern hawthorn blends, as well as modified blends with substituted ratios of 3-methylbutan-1-ol, butyl hexanoate, dihydro-ß-ionone, indicated that the 'agonist' or 'antagonist' effects of these volatiles depended on the ratio, or balance of compounds within the blend. In addition, the new blend contains a number of esters identified from the headspace of domesticated apple, Malus domestica, that are attractive to apple-origin R. pomonella, and present in the five other blends from southern hawthorns, including the southern C. mollis var. texana blend, but are not part of the previously identified blend from northern C. mollis fruit. This finding supports the hypothesis that in addition to providing specificity to the odor blends of the northern and southern hawthorn populations, the presence of the significant amounts of ester compounds in the new northern hawthorn blend might have provided a source of standing variation that could help explain the shift in host preference by C. mollis-infesting flies to introduced apple in the mid-1800's.


Subject(s)
Crataegus/chemistry , Tephritidae/physiology , Volatile Organic Compounds/chemistry , Animals , Arthropod Antennae/physiology , Behavior, Animal/physiology , Crataegus/metabolism , Fruit/chemistry , Fruit/metabolism , Gas Chromatography-Mass Spectrometry , Host-Parasite Interactions , Malus/chemistry , Malus/metabolism , New England , Smell , Volatile Organic Compounds/analysis
8.
Cell Mol Biol (Noisy-le-grand) ; 62(11): 100-107, 2016 Sep 30.
Article in English | MEDLINE | ID: mdl-27755960

ABSTRACT

The present study describes the effects of light conditions, different kinds and concentrations of auxins [Naphthylacetic acid (NAA) and dichlorophenoxyacetic acid (2,4-D)] with cytokinin (Kin) in MS medium on callus induction and embryogenesis in Crataegus pseudoheterophylla, C. aronia and C.meyeri. At first leave explants sections were cultured on different combinations of plant growth regulators in dark and light for callus initiation and light conditions to evaluation the percentage and duration of survival, callus diameter, callus fresh weight and dry. Results of effects of plant growth regulators and light conditions on callus initiation revealed that highest percentage of callus initiation leaves in treatment (0.5 mg/l 2.4-D+0.5 mg/l KIN) for species C.pseudoheterophylla in dark conditions (100%). Dark conditions (100%) were more effective on callogenesis than light conditions (Photoperiodicity of 16-h and at light intensity of 40 µmol m-2 s-1). The callus induction of in vitro (64-100%) leaves was better than the ex vitro ones (0-100%). The combination of 2,4-D and Kin of in vitro leaves callogenesis has been indicated faster (one weeks) than the other combinations. The results also showed that the highest percentage (100%) and survival duration (6 months) was found in species C. pseudoheterophylla and C. meyeri in 0.1 mg/l 2,4.D + 0.5 mg/l KIN and 0.5 mg/l 2,4.D + 0.5 mg/l Kin. The minimum survival (0%) was absorbed in species C. aronia in 1 mg/l NAA. Maximum callus (10.63 and 10.00 mm respectively) was shown in 0.1 mg/l 2,4.D + 0.5 mg/l Kin and 0.5 mg/l 2,4.D + 0.5 mg/l Kin and was not significant differences after five week among species. The results showed that the highest fresh (1081.49 mg) and dry weight (506.88 and 506.98 mg respectively) was absorbed in species C. pseudoheterophylla in 0.1 mg/l 2,4.D + 0.5 mg/l Kin and 0.5 mg/l 2,4.D + 0.5 mg/l Kin. The embryogenesis was not occurred in any plant growth regulator combinations and species. The results of this study suggested that using 2,4-D with cytokinin (Kin) would be more beneficial for callogenesis.


Subject(s)
Cell Dedifferentiation/drug effects , Crataegus/chemistry , Plant Extracts/pharmacology , Crataegus/metabolism , Light , Plant Cells/drug effects , Plant Cells/physiology , Plant Cells/radiation effects , Plant Extracts/chemistry , Plant Growth Regulators/pharmacology , Plant Leaves/chemistry , Plant Leaves/metabolism
9.
Plant Cell Environ ; 38(6): 1104-15, 2015 Jun.
Article in English | MEDLINE | ID: mdl-25292455

ABSTRACT

Stem respiration plays a role in species coexistence and forest dynamics. Here we examined the intra- and inter-specific variability of stem CO2 efflux (E) in dominant and suppressed trees of six deciduous species in a mixed forest stand: Fagus sylvatica L., Quercus petraea [Matt.] Liebl, Quercus pyrenaica Willd., Prunus avium L., Sorbus aucuparia L. and Crataegus monogyna Jacq. We conducted measurements in late autumn. Within species, dominants had higher E per unit stem surface area (Es ) mainly because sapwood depth was higher than in suppressed trees. Across species, however, differences in Es corresponded with differences in the proportion of living parenchyma in sapwood and concentration of non-structural carbohydrates (NSC). Across species, Es was strongly and NSC marginally positively related with an index of drought tolerance, suggesting that slow growth of drought-tolerant trees is related to higher NSC concentration and Es . We conclude that, during the leafless period, E is indicative of maintenance respiration and is related with some ecological characteristics of the species, such as drought resistance; that sapwood depth is the main factor explaining variability in Es within species; and that the proportion of NSC in the sapwood is the main factor behind variability in Es among species.


Subject(s)
Carbon Dioxide/metabolism , Plant Stems/physiology , Trees/physiology , Crataegus/metabolism , Crataegus/physiology , Ecology , Fagus/metabolism , Fagus/physiology , Plant Stems/metabolism , Prunus avium/metabolism , Prunus avium/physiology , Quercus/metabolism , Quercus/physiology , Sorbus/metabolism , Sorbus/physiology , Trees/metabolism
10.
Bioorg Med Chem Lett ; 23(20): 5599-604, 2013 Oct 15.
Article in English | MEDLINE | ID: mdl-23999046

ABSTRACT

Nine new 8-O-4' neolignans, named pinnatifidanin B I-IX (1-9), together with 9 known analogs (10-18) were isolated from the seeds of Crataegus pinnatifida. The structures of 1-18 were determined by spectroscopic methods, including 1D, 2D NMR, CD and HRESIMS analysis. Compounds 8-11, 17 and 18 displayed potent cytotoxic activities against human cancer cell lines, and most interestingly, none of the 6 compounds displayed inhibitory activity against human lung cell line (Mrc5). The 6 cytotoxic compounds are considered to be potential as antitumor agents, which could significantly inhibit the cancer cell growth in a dose-dependent manner and are probably safer than positive control drug.


Subject(s)
Antineoplastic Agents, Phytogenic/chemistry , Crataegus/chemistry , Lignans/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/toxicity , Cell Line, Tumor , Cell Survival/drug effects , Circular Dichroism , Crataegus/metabolism , Drug Screening Assays, Antitumor , Humans , Lignans/isolation & purification , Lignans/toxicity , Magnetic Resonance Spectroscopy , Molecular Conformation , Seeds/chemistry , Seeds/metabolism
11.
Plant Physiol Biochem ; 194: 111-121, 2023 Jan.
Article in English | MEDLINE | ID: mdl-36399912

ABSTRACT

Crataegus is an economically important plant due to its medicinal and health-promoting properties. Flavonoids are the main functional components of Crataegus fruit. Fruits of naturally pollinated Crataegus maximowiczii possess an extraordinary black skin and are rich in anthocyanins and other flavonoids. However, the composition of anthocyanins and the overall molecular mechanism of anthocyanin biosynthesis in C. maximowiczii fruits have not been fully elucidated. In this study, the metabolome and transcriptome of C. maximowiczii fruits with black and red skin were analyzed. The results revealed that the differential metabolites and genes were enriched in the anthocyanin biosynthesis pathways in C. maximowiczii fruits. In total, 52 differentially accumulated flavonoid metabolites, 12 differentially accumulated anthocyanins and 22 differentially expressed genes were identified. After weighted gene coexpression network analysis, two modules were found to be highly interrelated with the accumulation of anthocyanin components. The coexpression networks of these two modules were used to identify key candidate transcription factors associated with anthocyanin biosynthesis, such as MYB5, MYB113, bHLH60, ERF105, bZIP44, NAC082, and WRKY11. The results revealed that cyanidin-based anthocyanins were the main pigments responsible for the black coloration of C. maximowiczii fruits. Based on these differentially accumulated anthocyanins and key genes, genetic and metabolic regulatory networks of anthocyanin biosynthesis were also proposed. Overall, this study elucidates the molecular basis of the formation of black color in C. maximowiczii fruits, and provides an intensive study on anthocyanin biosynthesis in C. maximowiczii for comprehensive utilization.


Subject(s)
Anthocyanins , Crataegus , Anthocyanins/metabolism , Fruit/genetics , Fruit/metabolism , Crataegus/genetics , Crataegus/metabolism , Gene Expression Regulation, Plant , Gene Expression Profiling , Flavonoids/genetics , Flavonoids/metabolism , Transcriptome/genetics , Metabolome
12.
J Chem Ecol ; 38(3): 319-29, 2012 Mar.
Article in English | MEDLINE | ID: mdl-22399441

ABSTRACT

The apple maggot fly, Rhagoletis pomonella, infests apple (Malus domestica) and hawthorn species (most notably the downy hawthorn, Crataegus mollis) in the eastern USA. Evidence suggests that the fly was introduced into the western USA sometime in the last 60 years. In addition to apple, R. pomonella also infests two species of hawthorns in the western USA as major hosts: the native black hawthorn (C. douglasii) and the introduced ornamental English hawthorn, C. monogyna. Apple and downy hawthorn-origin flies in the eastern USA use volatile blends emitted from the surface of their respective ripening fruit to find and discriminate among host trees. To test whether the same is true for western flies, we used coupled gas chromatography and electroantennographic detection (GC-EAD) and developed a 7-component apple fruit blend for western apple-origin flies, an 8-component black hawthorn fruit blend for flies infesting C. douglasii, and a 9-component ornamental hawthorn blend for flies from C. monogyna. Crataegus douglasii and C. monogyna-origin flies showed similar levels of upwind directed flight to their respective natal synthetic fruit blends in flight tunnel assays compared to whole fruit adsorbent extracts, indicating that the blends contain all the behaviorally relevant fruit volatiles to induce maximal response levels. The black and ornamental hawthorn blends shared four compounds in common including 3-methylbutan-1-ol, which appears to be a key volatile for R. pomonella populations in the eastern, southern, and western USA that show a preference for fruit from different Crataegus species. However, the blends also differed from one another and from domesticated apple in several respects that make it possible that western R. pomonella flies behaviorally discriminate among fruit volatiles and form ecologically differentiated host races, as is the case for eastern apple and hawthorn flies.


Subject(s)
Crataegus/metabolism , Diptera/physiology , Host-Parasite Interactions , Malus/metabolism , Volatile Organic Compounds/metabolism , Animals , Crataegus/parasitology , Flight, Animal , Fruit/metabolism , Fruit/parasitology , Malus/parasitology , United States
13.
J Chem Ecol ; 37(9): 974-83, 2011 Sep.
Article in English | MEDLINE | ID: mdl-21887525

ABSTRACT

The apple maggot fly, Rhagoletis pomonella, infests several hawthorn species in the southern USA. In a companion paper, we showed that R. pomonella flies infesting two different mayhaw species (Crataegus opaca and C. aestivalis) can discriminate between volatile blends developed for each host fruit, and that these blends are different from previously constructed blends for northern fly populations that infest domestic apple (Malus domestica), downy hawthorn (Crataegus mollis), and flowering dogwood (Cornus florida). Here, we show by using coupled gas chromatography and electroantennographic detection (GC-EAD), gas chromatography with mass spectrometry (GC-MS), and flight tunnel bioassays, that two additional southern hawthorn fly populations infesting C. viridis (green hawthorn) and C. brachyacantha (blueberry hawthorn) also can discriminate between volatile blends for each host fruit type. A 9-component blend was developed for C. viridis (3-methylbutan-1-ol [5%], butyl butanoate [19.5%], propyl hexanoate [1.5%], butyl hexanoate [24%], hexyl butanoate [24%], pentyl hexanoate [2.5%], 1-octen-3-ol [0.5%], pentyl butanoate [2.5%], and (3E)-4,8-dimethyl-1,3,7-nonatriene (DMNT) [20.5%]) and an 8-component blend for C. brachyacantha (3-methylbutan-1-ol [0.6%], butyl acetate [50%], pentyl acetate [3.5%], butyl butanoate [9%], butyl hexanoate [16.8%], hexyl butanoate [16.8%], 1-octen-3-ol [0.3%], and pentyl butanoate [3%]). Crataegus viridis and C. brachyacantha-origin flies showed significantly higher levels of upwind oriented flight to their natal blend in flight tunnel assays compared to the alternate, non-natal blend and previously developed northern host plant blends. The presence of DMNT in C. viridis and butyl acetate in C. brachyacantha appeared to be largely responsible for driving the differential response. This sharp behavioral distinction underscores the diversity of odor response phenotypes in the southern USA, points to possible host race formation in these populations, and despite the presence of several apple volatiles in both blends, argues against a functional apple race existing on southern host plants prior to the introduction of apple to North America.


Subject(s)
Crataegus/parasitology , Fruit/parasitology , Host-Parasite Interactions , Tephritidae/physiology , Volatile Organic Compounds/metabolism , Animals , Chromatography, Gas , Crataegus/metabolism , Fruit/metabolism , Gas Chromatography-Mass Spectrometry , Odorants , Phenotype , Species Specificity , Volatile Organic Compounds/analysis
14.
J Chem Ecol ; 37(9): 961-73, 2011 Sep.
Article in English | MEDLINE | ID: mdl-21892724

ABSTRACT

The apple maggot fly, Rhagoletis pomonella, infests several hawthorn species in the southern USA. Here, we tested the hypothesis that these populations could serve as reservoirs for fruit odor discrimination behaviors facilitating sympatric host race formation and speciation, specifically the recent shift from downy hawthorn (Crataegus mollis) to domestic apple (Malus domestica) in the northern USA. Coupled gas chromatography and electroantennographic detection (GC-EAD), gas chromatography with mass spectrometry (GC-MS), and flight tunnel bioassays were used to identify the behaviorally active natal fruit volatile blends for three of the five major southern hawthorns: C. opaca (western mayhaw), C. aestivalis (eastern mayhaw), and C. rufula (a possible hybrid between C. opaca and C. aestivalis). A 6-component blend was developed for C. opaca (3-methylbutan-1-ol [44%], pentyl acetate [6%], butyl butanoate [6%], propyl hexanoate [6%], butyl hexanoate [26%], and hexyl butanoate [12%]); an 8-component blend for C. aestivalis (3-methylbutan-1-ol [2%], butyl acetate [47%], pentyl acetate [2%], butyl butanoate [12%], propyl hexanoate [1%], butyl hexanoate [25%], hexyl butanoate [9%], and pentyl hexanoate [2%]); and a 9-component blend for C. rufula (3-methylbutan-1-ol [1%], butyl acetate [57%], 3-methylbutyl acetate [3%], butyl butanoate [5%], propyl hexanoate [1%], hexyl propionate [1%], butyl hexanoate [23%], hexyl butanoate [6%], and pentyl hexanoate [3%]). Crataegus aestivalis and C. opaca-origin flies showed significantly higher levels of upwind directed flight to their natal blend in flight tunnel assays compared to the non-natal blend and previously developed apple, northern downy hawthorn, and flowering dogwood blends. Eastern and western mayhaw flies also were tested to the C. rufula blend, with eastern flies displaying higher levels of upwind flight compared with the western flies, likely due to the presence of butyl acetate in the C. aestivalis and C. rufula blends, an agonist compound for eastern mayhaw-origin flies, but a behavioral antagonist for western flies. The results discount the possibility that the apple fly was "pre-assembled" and originated via a recent introduction of southern mayhaw flies predisposed to accepting apple. Instead, the findings are consistent with the possibility of southern mayhaw-infesting fly host races. However, mayhaw fruits do emit several volatiles found in apple. It is, therefore, possible that the ability of the fly to evolve a preference for apple volatiles, although not the entire blend, stemmed, in part, from standing variation related to the presence of these compounds in southern mayhaw fruit.


Subject(s)
Crataegus/parasitology , Fruit/parasitology , Host-Parasite Interactions , Tephritidae/physiology , Volatile Organic Compounds/metabolism , Animals , Crataegus/metabolism , Fruit/metabolism , Gas Chromatography-Mass Spectrometry/methods , Malus/metabolism , Malus/parasitology , Smell , United States , Volatile Organic Compounds/analysis
15.
Sci Rep ; 10(1): 8876, 2020 06 01.
Article in English | MEDLINE | ID: mdl-32483369

ABSTRACT

Present study was designed to compared the total flavonoids and polyphenols contents and antibacterial activity of hawthorn extracts with different polarities as well as the underlying antibacterial mechanisms. The results showed that among all hawthorn extracts, methanol and ethanol extracts (ME and EE) exhibited high levels of total flavonoids and polyphenols contents, followed by acetone, ethyl acetate, trichloromethane and petroleum ether extracts. ME exhibited the strongest antibacterial activity against tested bacteria, especially Staphylococcus aureus with a 1.25 µg/mL of the minimum inhibitory concentration (MIC) and minimum bactericide concentration (MBC). Further analysis revealed that the main phenolic compounds from ME were epicatechin (281.6 mg/100 g DW), procyanidin B2 (243.5 mg/100 g DW), chlorogenic acid (84.2 mg/100 g DW) and quercetin (78.4 mg/100 g DW). The action mechanism of ME against S. aureus could be ascribed to ME damaging cell wall and cell membrane integrity, inhibiting intracellular enzyme activity, increasing reactive oxygen species (ROS), also changing expression of associated genes and then inducing apoptosis of S. aureus. In addition, the antimicrobial activity of ME against S. aureus has also been demonstrated to be efficient in the food matrix (whole milk).


Subject(s)
Anti-Bacterial Agents/chemistry , Crataegus/chemistry , Plant Extracts/chemistry , Anti-Bacterial Agents/pharmacology , Catechin/pharmacology , Cell Wall/drug effects , Cell Wall/physiology , Chlorogenic Acid/pharmacology , Chromatography, High Pressure Liquid , Crataegus/metabolism , Flavonoids/chemistry , Gram-Negative Bacteria/drug effects , Gram-Positive Bacteria/drug effects , Membrane Potentials/drug effects , Microbial Sensitivity Tests , Phenols/chemistry , Plant Extracts/pharmacology , Reactive Oxygen Species/metabolism
16.
J Chromatogr A ; 1112(1-2): 339-44, 2006 Apr 21.
Article in English | MEDLINE | ID: mdl-16443232

ABSTRACT

Flavonoids are an important group of natural compounds, which can prevent coronary heart disease and have antioxidant properties. Hawthorn is a well known and widely used medicinal plant due to its cardiotonic activity. Previous studies refer mostly to the HPLC analysis of the flavonoids: vitexin, quercetin, hyperoside, oligomeric procyanidins, which appear to be primarily responsible for the cardiac action of the plant. Aqueous ethanolic extracts of single-styled hawthorn (Crataegus monogyna Jacq., f.: Rosaceae Juss.) leaves and sprouts were analyzed by means of capillary zone electrophoresis (CZE). Influence of vegetation period on the extract qualitative composition and flavonoids quantities was evaluated. Sample preparation by extraction using different concentration of aqueous ethanol (40-96%, v/v) and the influence of extractant composition on the recovery of flavonoids are discussed in detail. The results obtained using CZE are compared to the results of spectrophotometric and HPLC analysis of the extracts. The effect of storage conditions of extracts (solar irradiation, temperature and duration) on degradation of flavonoids was investigated.


Subject(s)
Crataegus/chemistry , Electrophoresis, Capillary/methods , Flavonoids/analysis , Plant Extracts/chemistry , Crataegus/metabolism , Drug Storage , Flavonoids/isolation & purification , Reproducibility of Results , Seasons
17.
Evolution ; 59(7): 1552-9, 2005 Jul.
Article in English | MEDLINE | ID: mdl-16153040

ABSTRACT

Understanding speciation requires discerning how reproductive barriers to gene flow evolve between previously interbreeding populations. Models of sympatric speciation for phytophagous insects posit that reproductive isolation can evolve in the absence of geographic isolation as a consequence of an insect shifting and ecologically adapting to a new host plant. One important adaptation contributing to sympatric differentiation is host-specific mating. When organisms mate in preferred habitats, a system of positive assortative mating is established that facilitates sympatric divergence. Models of host fidelity generally assume that host choice is determined by the aggregate effect of alleles imparting positive preferences for different plant species. But negative effect genes for avoiding nonnatal plants may also influence host use. Previous studies have shown that apple and hawthorn-infesting races of Rhagoletis pomonella flies use volatile compounds emitted from the surface of fruit as key chemosensory cues to recognize and distinguish between their host plants. Here, we report results from field trials indicating that in addition to preferring the odor of their natal fruit, apple and hawthorn flies, and their undescribed sister species infesting flowering dogwood (Cornus florida), also avoid the odors of nonnatal fruit. We discuss the implications of nonnatal fruit avoidance for the evolutionary dynamics and genetics of sympatric speciation. Our findings reveal an underappreciated role for habitat avoidance as a potential postmating, as well as prezygotic, barrier to gene flow.


Subject(s)
Environment , Genetics, Population , Models, Biological , Odorants , Sexual Behavior, Animal/physiology , Tephritidae/physiology , Animals , Cornus/metabolism , Crataegus/metabolism , Fruit/metabolism , Indiana , Malus/metabolism , Michigan , Species Specificity
18.
Chem Biol Interact ; 238: 42-7, 2015 Aug 05.
Article in English | MEDLINE | ID: mdl-26070415

ABSTRACT

This study aims to compare the effects of feeding haw pectin (HP), haw pectin hydrolyzates (HPH), and haw pectin pentasaccharide (HPPS) on the cholesterol metabolism of hypercholesterolemic hamsters induced by high-cholesterol diets. The animals were fed a standard diet (SD), high-cholesterol diet (HCD), or HCD plus HP, HPH, or HPPS at a dose of 300mg/kg body weight for 4weeks. Results showed that HPPS was more effective than HP and HPH in decreasing the body weight gain (by 38.2%), liver weight (by 16.4%), and plasma and hepatic total cholesterol (TC; by 23.6% and 27.3%, respectively) of hamsters. In addition, the bile acid levels in the feces were significantly higher by 39.8% and 132.8% in the HPH and HPPS groups than in the HCD group. Such changes were not noted in the HP group. However, the HP group had higher cholesterol excretion capacities than the HPH and HPPS groups by inhibiting cholesterol absorption in the diet, with a 21.7% increase in TC excretion and a 31.1% decrease in TC absorption. Thus, HPPS could be a promising anti-atherogenic dietary ingredient for the development of functional food to improve cholesterol metabolism.


Subject(s)
Cholesterol/metabolism , Crataegus/metabolism , Diet, High-Fat , Liver/drug effects , Pectins/pharmacology , Plant Extracts/pharmacology , Animals , Bile Acids and Salts/analysis , Cholesterol/blood , Cholesterol, HDL/analysis , Cholesterol, HDL/blood , Chromatography, High Pressure Liquid , Crataegus/chemistry , Cricetinae , Feces/chemistry , Lipids/analysis , Liver/metabolism , Liver/pathology , Male , Pectins/metabolism , Plant Extracts/metabolism , Triglycerides/analysis , Triglycerides/blood
19.
PLoS One ; 8(9): e72910, 2013.
Article in English | MEDLINE | ID: mdl-24039819

ABSTRACT

Hawthorn (Crataegus spp.) is an important pome with a long history as a fruit, an ornamental, and a source of medicine. Fruits of hawthorn are marked by hard stony endocarps, but a hawthorn germplasm with soft and thin endocarp was found in Liaoning province of China. To elucidate the molecular mechanism underlying the soft endocarp of hawthorn, we conducted a de novo assembly of the fruit transcriptome of Crataegus pinnatifida and compared gene expression profiles between the soft-endocarp and the hard-endocarp hawthorn varieties. De novo assembly yielded 52,673 putative unigenes, 20.4% of which are longer than 1,000 bp. Among the high-quality unique sequences, 35,979 (68.3%) had at least one significant match to an existing gene model. A total of 1,218 genes, represented 2.31% total putative unigenes, were differentially expressed between the soft-endocarp hawthorn and the hard-endocarp hawthorn. Among these differentially expressed genes, a number of lignin biosynthetic pathway genes were down-regulated while almost all the flavonoid biosynthetic pathway genes were strongly up-regulated, concomitant with the formation of soft endocarp. In addition, we have identified some MYB and NAC transcription factors that could potentially control lignin and flavonoid biosynthesis. The altered expression levels of the genes encoding lignin biosynthetic enzymes, MYB and NAC transcription factors were confirmed by quantitative RT-PCR. This is the first transcriptome analysis of Crataegus genus. The high quality ESTs generated in this study will aid future gene cloning from hawthorn. Our study provides important insights into the molecular mechanisms underlying soft endocarp formation in hawthorn.


Subject(s)
Crataegus/genetics , Gene Expression Regulation, Plant , Transcriptome , Crataegus/metabolism , Expressed Sequence Tags , Flavonoids/biosynthesis , Fruit/genetics , Fruit/metabolism , Gene Regulatory Networks , High-Throughput Nucleotide Sequencing , Lignin/biosynthesis , Metabolic Networks and Pathways/genetics , Molecular Sequence Annotation , Phenotype , Sequence Analysis, RNA
20.
J Photochem Photobiol B ; 128: 50-7, 2013 Nov 05.
Article in English | MEDLINE | ID: mdl-24007865

ABSTRACT

The aim of our study was to investigate the photoprotective activity and photostability efficacy of sunscreen formulations containing Helichrysum arenarium, Sambucus nigra, Crataegus monogyna extracts and their combination. UV transmission of the emulsion films was performed by using diffuse transmittance measurements coupling to an integrating sphere. In vitro photoprotection and photostability efficacy were evaluated according to the following parameters: sun protection factor (SPF), UVA protection factor (PF-UVA), UVA/UVB ratio and critical wavelength (λc) before and after UV irradiation. The results obtained show that the formulations containing polyphenols fulfill the official requirements for sunscreen products due to their broad spectrum of UV protection combined with their high photostability and remarkable antioxidant properties. Therefore H. arenarium, S. nigra, C. monogyna extracts represent useful additives for cosmetic formulation.


Subject(s)
Crataegus/chemistry , Helichrysum/chemistry , Plant Extracts/chemistry , Sambucus nigra/chemistry , Sunscreening Agents/chemistry , Ultraviolet Rays , Chemistry, Pharmaceutical , Chromatography, High Pressure Liquid , Cosmetics , Crataegus/metabolism , Drug Stability , Emulsions/chemistry , Flavonoids/analysis , Helichrysum/metabolism , Plant Extracts/isolation & purification , Sambucus nigra/metabolism , Spectrophotometry , Sun Protection Factor , Sunscreening Agents/isolation & purification
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