In the present study, we developed and validated a high-performance liquid chromatography method for the simultaneous determination of seven phenylpropanoid compounds （2-hydroxyl cinnamaldehyde, coumarin, cinnamyl al...In the present study, we developed and validated a high-performance liquid chromatography method for the simultaneous determination of seven phenylpropanoid compounds （2-hydroxyl cinnamaldehyde, coumarin, cinnamyl alcohol, cinnamic acid, 2-methoxy cinnamic acid, cinnamaldehyde and 2-methoxy cinnamaldehyde） in Cinnamomi Cortex and Cinnamomi Ramulus. The levels of seven phenylpropanoid compounds in Cinnamomi Cortex and Cinnamomi Ramulus were compared using this method. A total of 48 samples （27 Cinnamomi Cortex and 21 Cinnamomi Ramulus） were purchased in China and analyzed. Quantities of seven phenylpropanoid compounds ranged from 17.5 to 61.6 mg/g in Cinnamomi Cortex and ranged from 9.91 to 23.4 mg/g in Ciunamomi Ramulus. The level of 2-methoxy cinnamic acid in the Cinnamomi Cortex samples was below the LOD, whereas it ranged from 0 to 0.119 mg/g in the Cinnamomi Ramulus samples. The （cinnamyl alcohol＋cinnamic acid）/cinnamaldehyde ratios （R346） of Ciunamomi Cortex and Cinnamomi Ramulus ranged from 0.0121 to 0.0467 and 0.0598 to 0.182, respectively. This ratio could be used to discriminate Cinnamomi Cortex （〈0.05） and Cinnamomi Ramulus （〉0.05）. The extraction rates （Dn） of seven compounds in boiling water were different, with the lowest dissolution for cinnamaldehyde （〈3%） and the highest for cinnamic acid （about 60%）.展开更多
The regioselective acylation of unprotected phenylethyl glucoside withcinnamoyl chloride leads to 6-OH cin-namoylated glucoside. In this manner, thirteen phenylpropanoidglycoside analogs were designed and prepared. Th...The regioselective acylation of unprotected phenylethyl glucoside withcinnamoyl chloride leads to 6-OH cin-namoylated glucoside. In this manner, thirteen phenylpropanoidglycoside analogs were designed and prepared. Their structure was confirmed by ~1H NMR and ^(13)CNMR spectra.展开更多
A novel phenylpropanoid glycosides 1, named parispolyside E and a novel derivation of phenolic glycoside 2, named parispolyside G, as well as two known flavonoid glycosides were isolated from the rhizome of Paris poly...A novel phenylpropanoid glycosides 1, named parispolyside E and a novel derivation of phenolic glycoside 2, named parispolyside G, as well as two known flavonoid glycosides were isolated from the rhizome of Paris polyphylla var. yunnanensis. Their structures were elucidaed by spectroscopic methods.展开更多
A novel phenylpropanoid glycoside, Callicarposide A has been isolated from the aerial parts of Callicarpa kwangtungensis Chun. The chemical structure is elucidated on the basis of spectral analysis. C 2009 Teng Fei Ji...A novel phenylpropanoid glycoside, Callicarposide A has been isolated from the aerial parts of Callicarpa kwangtungensis Chun. The chemical structure is elucidated on the basis of spectral analysis. C 2009 Teng Fei Ji. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.展开更多
Two new triterpenoid saponins,ardisicrenoside R and S(1 and 2),and one new phenylpropanoid glycoside,ardicrephenin(3),along with five known compounds(4-8),were isolated from roots of Ardisia crenata.Their structures w...Two new triterpenoid saponins,ardisicrenoside R and S(1 and 2),and one new phenylpropanoid glycoside,ardicrephenin(3),along with five known compounds(4-8),were isolated from roots of Ardisia crenata.Their structures were elucidated on the basis of NMR spectroscopic data and chemical methods.Compounds 2-7 were evaluated for their cytotoxic activities against A549,MCF-7,HepG2 and MDA-MB-231 cell lines by MTT assay.Ardicrenin(6)showed significant cytotoxicity,with IC50 values of 1.17±0.01,1.19±0.06,3.52±0.23,and 16.61±1.02μmol·L^(-1),respectively.展开更多
Two new phenylpropanoid glycosides, 9-O-[6-O-acetyl-β-D-glucopyranosyl]-4-hydroxycinnamic acid （1） and 8-O-β-D-glucopyranosyl-（R）-（＋）-3,4,8-trihydroxy methyl phenylpropionate （2） were isolated from the 80% ...Two new phenylpropanoid glycosides, 9-O-[6-O-acetyl-β-D-glucopyranosyl]-4-hydroxycinnamic acid （1） and 8-O-β-D-glucopyranosyl-（R）-（＋）-3,4,8-trihydroxy methyl phenylpropionate （2） were isolated from the 80% EtOH extract of the roots of Sanguisorba officinalis. Their slructures were characterized by spectroscopic analysis and chemical method, including 1D NMR, 2D NMR, and HR-ESI-MS. Compounds 1 and 2 exhibited the moderate antimicrobial activities against all Gram-positive and Gram-negative bacteria tested.展开更多
AIM: To investigate the chemical and bioactive constituents from the stems and leaves of Micromelum integerrimum. METHOD: The chemical constituents were isolated and purified by silica gel, Sephadex LH-20, and HPLC. T...AIM: To investigate the chemical and bioactive constituents from the stems and leaves of Micromelum integerrimum. METHOD: The chemical constituents were isolated and purified by silica gel, Sephadex LH-20, and HPLC. Their structures were mainly elucidated on the basis of extensive 1D- and 2D-NMR spectroscopy and mass spectrometry. Their cytotoxicity and antimicrobial activities were tested by the SRB and turbidimetric methods, respectively. RESULTS: Two new phenylpropanoids and two known coumarins were obtained, and their structures were identified as microintegerrin A(1), microintegerrin B(2), scopoletin(3), and scopolin(4). All of the compounds were tested for their cytotoxicity against three cancer cell lines(HeLa, A549, and BGC-823) and for antimicrobial activity against the fungus Candida albicans and the bacterium Staphylococcus aureus. CONCLUSION: Two new phenylpropanoids 1 and 2 were isolated and identified from the stems and leaves of M. intgerrimum. None of the compounds showed cytotoxic or antimicrobial activity at the tested concentration of 20 ?g·mL–1.展开更多
A novel phenylpropanoid-substituted catechin glycoside glabraoside A 1 and a new dihydrochalcone 3＇-（7＂-allylphenyl）-2＇,4＇,4＂-trihydroxy-6＇-methoxydihydrochalcone 2 were isolated from the herbs of Sarcandra gl...A novel phenylpropanoid-substituted catechin glycoside glabraoside A 1 and a new dihydrochalcone 3＇-（7＂-allylphenyl）-2＇,4＇,4＂-trihydroxy-6＇-methoxydihydrochalcone 2 were isolated from the herbs of Sarcandra glabra. Their structures were elucidated on the basis of spectroscopic analyses and chiroptical methods.展开更多
A new phenylpropanoid glycoside, serratumoside A, was isolated from the aerial parts of Clerodendrum serratum var. amplexifolium Moldenke. Its structure was determined by spectral and chemical methods.
Peaches are subject to flesh softening during postharvest storage and transport,which affects the storage life of the fruit and causes huge economic losses.Previous research has demonstrated that postharvest brassinol...Peaches are subject to flesh softening during postharvest storage and transport,which affects the storage life of the fruit and causes huge economic losses.Previous research has demonstrated that postharvest brassinolide treatment can maintain flesh firmness,ascorbic acid and soluble solids contents,and enhance disease resistance in peach fruits.This study assessed the influence of postharvest brassinolide treatment on the expression of key genes involved in cell wall degradation and the phenylpropanoid pathway in peach fruits by real-time fluorescence quantitative polymerase chain reaction(qPCR).The results showed that brassinolide dipping inhibited the gene expression of pectate lyase 1,polygalacturonase 21 and pectin methylesterase 1,and significantly enhanced the gene expression of peroxidase,cinnamoyl-CoA reductase,phenylalanine ammonia lyase and caffeoyl-CoA-O-methyltransferase 5 in peach fruits.It also increased the gene expression levels of chaleone synthase,chaleone isomerase,dihydroflavonol-4-reductase and flavanone 3-hydroxylase at the early stage of storage.These findings imply that brassinolide can suppress the expression of key genes involved in cell wall degradation and enhance the expression of key genes involved in the phenylpropanoid pathway,thereby delaying peach fruit softening and enhancing disease resistance.展开更多
In the present paper are discussed the results of the investigations of the phenylpropanoids of the medicinal plants which are of the great interest as the sources of the neurotropic, adaptogenic, immunostimulating, a...In the present paper are discussed the results of the investigations of the phenylpropanoids of the medicinal plants which are of the great interest as the sources of the neurotropic, adaptogenic, immunostimulating, antioxidative, and hepatoprotective preparations. There were shown the necessity of using of the standard samples of triandrin (Rhodiola rosea L. tissue cultures, Salix viminalis L. barks), rosavin (Rhodiola rosea L. rhizomes), syringin, or eleutheroside B [Eleutherococcus senticosus (Rupr. et Maxim.) Maxim. rhizomes, Syringa vulgaris L. barks], and silybin [Silybum marianum (L.) Gaertn. fruits] for purpose of the standardization of the corresponding drugs and pharmaceuticals. It was shown also the significance of γ-schizandrin, chicoric acid, rosmarinic acid and lavandoside for purposes of the standardization of raw material and preparations of Schizandra chinensis Baill. fruits and seeds, Echinacea purpurea (L.) Moench. herbs, Melissa officinalis L. herbs and Lavandula spica L. flowers respectively.展开更多
The role of lignifications and enzymes involved in the phenylpropanoid (PP) biosynthesis i.e. phenylalanine ammonia lyase (PAL), Peroxidase (POD), Polyphenol oxidase (PPO) in providing resistance to Karnal Bunt (KB) d...The role of lignifications and enzymes involved in the phenylpropanoid (PP) biosynthesis i.e. phenylalanine ammonia lyase (PAL), Peroxidase (POD), Polyphenol oxidase (PPO) in providing resistance to Karnal Bunt (KB) during different developmental stages of resistant (HD-29) and susceptible genotype (WH-542) and its recombinant inbred lines (RILs) of wheat were investigated. The enzymes of PP pathway were expressed constitutively in both the susceptible and resistant genotype. However, the activity was higher in all the developmental stages of resistant genotype and its RILs, indicating that this genotype has a significant higher basal level of these enzymes as compared to the susceptible line and could be used as marker(s) to define KB resistance. The activity of PAL and POD was significantly higher in WSv stage (Z = 16) while the specific activity of PPO was higher in WS3 (Z = 77) stage as compared to the other physiological stages in both the genotypes. In resistant genotype the lignin content increased two-fold and three-fold at WS2 and WS3 stage, respectively, while in susceptible genotype no significant increase in lignin content was observed. The pathway might be associated with the enhancement of structural defense barrier due to lignifications of cell wall as evident from the enhanced synthesis of lignin in all the stages of resistant genotype. Our results clearly indicate the possible role of enzymes of PP metabolism provides genotype and stage dependant structural barrier resistance in wheat against KB.展开更多
Two new amides(E)-N-cinnamoyl-2-methoxypiperidine(1)and(R)-1-(2-oxopyrrolidin-3-yl)-5,6-dihydropyridin-2(1H)-one(2),four new amide glucosides,retrofractosides A-D(3-6),and two new phenylpropanoid glucosides,retrofract...Two new amides(E)-N-cinnamoyl-2-methoxypiperidine(1)and(R)-1-(2-oxopyrrolidin-3-yl)-5,6-dihydropyridin-2(1H)-one(2),four new amide glucosides,retrofractosides A-D(3-6),and two new phenylpropanoid glucosides,retrofractosides E(7)and F(8),together with 24 known compounds(9-32)were isolated from the fruits of Piper retrofractum.The chemical structures of these new compounds were elucidated based on extensive spectroscopic analysis.All of these isolates(1-32)were evaluated for inhibitory activity against mouse platelet aggregation induced by the peptide AYPGKF-NH2.(E)-N-(Tetrahydro-2H-pyran-2-yl)cinnamamide(9)showed a weak inhibitory efect,with an inhibition ratio of 52.0%at a concentration of 150μM.展开更多
OBJECTIVE To explore the hypolipidemic mechanisms of the total phenylpropanoid glycosides fromLigustrum robustum(Roxb.) Blume(LRTPG) in hamsters using proteomics technique.METHODS The hamsters were fed with a high fat...OBJECTIVE To explore the hypolipidemic mechanisms of the total phenylpropanoid glycosides fromLigustrum robustum(Roxb.) Blume(LRTPG) in hamsters using proteomics technique.METHODS The hamsters were fed with a high fat diet to induce hyperlipidemia.Then LRTPG of high(1.2 g·kg^(-1)),medium(0.6 g·kg^(-1)) and low(0.3 g·kg^(-1)) doses were administrated daily for 4 weeks.Then the concentrations of plasma and hepatic lipids were determined using enzymic methods.The total protein was extracted from livers of the model group and the group treated with the high dose of LRTPG for label-free quantitative proteomics.RESULTS LRTPG significantly reduced the concentrations of plasma and hepatic lipids in hamsters fed a high fat diet.The proteomics data showed that a total of 2231 proteins were identified,and 549 proteins were found to be differentially expressed between the model group and the group treated with LRTPG.Among the 549 proteins,93 proteins were up-regulated and 59 proteins were down-regulated,and 397 proteins were absent or not.And some of these proteins were much related to the lipid metabolism.Further,gene ontology(GO) analysis indicated metabolic process,transport,oxidation-reduction process,phosphorylation,signal transduction,lipid metabolic process were the main biological processes that those differentially expressed proteins participated.KEGG pathway analysis showed that those proteins were involved in several metabolic pathways including oxidative phosphorylation,non-alcoholic fatty liver disease(NAFLD),PI3K-Akt signaling pathway,cAMP signaling pathway,cGMP-PKG signaling pathway.CONCLUSION The proteomics study could provide valuable clues to help us to understand the hypolipidemic mechanisms of LRTPG much better.展开更多
Our continued interest in the research and development of cosmetic active ingredients deriving from natural sources led us to investigate the potential of a purified extract of Ajuga reptans, a plant belonging to the ...Our continued interest in the research and development of cosmetic active ingredients deriving from natural sources led us to investigate the potential of a purified extract of Ajuga reptans, a plant belonging to the family Labiatae and known for its traditional use in skin healing. The extracts deriving from a biotechnology platform are composed by meristematic cell culture, developed in the frame of a NTFP (non-timber forest product) project, and characterized by high content in phenylpropanoid, of which teupolioside represents the majority component. The latter is a phenylpropanoid glucoside, structurally correlated echinacoside and known in the literature for the antioxidant properties. This study was conducted with the purpose of evaluating the applicability of the Ajuga reptans extract within different cosmetic formulations. In particular, Photochemiluminescence (PCL) was used to proof the antioxidant capacity of cosmetic formulations containing the product, in relation to the change of the title of teupolioside. Furthermore, UVA and UVB filtering properties were also investigated. The results of the study showed relevantly antioxidant capacity of the finished formulation against superoxide anion, which is the main reactive oxygen species responsible for skin aging and significant synergic capacities to filter UV radiation.展开更多
Two pairs of chlorine-containing phenylpropanoid enantiomers（1a/1b and 2a/2b） were isolated from the rhizomes of Acorus tatarinowii. Interestingly, these optical isomers（1a/1b and 2a/2b） were co-existed in the sam...Two pairs of chlorine-containing phenylpropanoid enantiomers（1a/1b and 2a/2b） were isolated from the rhizomes of Acorus tatarinowii. Interestingly, these optical isomers（1a/1b and 2a/2b） were co-existed in the same plant, which were characterized as the first halogen-containing natural products from the genus Acorus. Their structures and absolute configurations were elucidated by a combination of spectroscopic analysis and a single-crystal X-ray diffraction, assisted by a modified Mosher＇s method. The phenylpropanoid isomers（1a/1b and 2a/2b） were evaluated for their antioxidant activities using DPPH assay and cytotoxic activities against five human cancer cell lines.展开更多
The general phenylpropanoid metabolism generates an enormous array of secondary metabolites based on the few intermediates of the shikimate pathway as the core unit. The resulting hydroxycinnamic acids and esters are ...The general phenylpropanoid metabolism generates an enormous array of secondary metabolites based on the few intermediates of the shikimate pathway as the core unit. The resulting hydroxycinnamic acids and esters are am- plified in several cascades by a combination of reductases, oxygenases, and transferases to result in an organ and devel- opmentally specific pattern of metabolites, characteristic for each plant species. During the last decade, methodology driven targeted and non-targeted approaches in several plant species have enabled the identification of the participating enzymes of this complex biosynthetic machinery, and revealed numerous genes, enzymes, and metabolites essential for regulation and compartmentation. Considerable success in structural and computational biology, combined with the an- alytical sensitivity to detect even trace compounds and smallest changes in the metabolite, transcript, or enzyme pattern, has facilitated progress towards a comprehensive view of the plant response to its biotic and abiotic environment. Trans- genic approaches have been used to reveal insights into an apparently redundant gene and enzyme pattern required for functional integrity and plasticity of the various phenylpropanoid biosynthetic pathways. Nevertheless, the function and impact of all members of a gene family remain to be completely established. This review aims to give an update on the various facets of the general phenylpropanoid pathway, which is not only restricted to common lignin or flavonoid biosynthesis, but feeds into a variety of other aromatic metabolites like coumarins, phenolic volatiles, or hydrolyzable tannins.展开更多
The mature cotton （Gossypium hirsutum L.） fiber is a single cell with a typically thickened secondary cell wall. The aim of this research was to use molecular, spectroscopic and chemical techniques to investigate th...The mature cotton （Gossypium hirsutum L.） fiber is a single cell with a typically thickened secondary cell wall. The aim of this research was to use molecular, spectroscopic and chemical techniques to investigate the possible occurrence of previously overlooked accumulation of phenolics during secondary cell wall formation in cotton fibers. Relative quantitative reverse transcription-polymerase chain reaction analysis showed that GhCAD6 and GhCAD1 were predominantly expressed among seven gene homologs, only GhCAD6 was up-regulated during secondary wall formation in cotton fibers. Phylogenic analysis revealed that GhCAD6 belonged to Class I and was proposed to have a major role in monolignol biosynthesis, and GhCAD1 belonged to Class III and was proposed to have a compensatory mechanism for monolignol biosynthesis. Amino acid sequence comparison showed that the cofactor binding sites of GhCADs were highly conserved with high similarity and identity to bona fide cinnamyl alcohol dehydrogenases. The substrate binding site of GhCAD1 is different from GhCAD6. This difference was confirmed by the different catalytic activities observed with the enzymes. Cell wall auto-fluorescence, Fourier transform infrared spectroscopy （FTIR）, high-performance liquid chromatography （HPLC） and chemical analyses confirmed that phenolic compounds were bound to the cell walls of mature cotton fibers. Our findings may suggest a potential for genetic manipulation of cotton fiber properties, which are of central importance to agricultural, cotton processing and textile industries.展开更多
Phenylpropanoid metabolism is one of the most important metabolisms in plants, yielding more than 8,000 metabolites contributing to plant development and plant-environment interplay.Phenylpropanoid metabolism material...Phenylpropanoid metabolism is one of the most important metabolisms in plants, yielding more than 8,000 metabolites contributing to plant development and plant-environment interplay.Phenylpropanoid metabolism materialized during the evolution of early freshwater algae that were initiating terrestrialization and land plants have evolved multiple branches of this pathway, which give rise to metabolites including lignin, flavonoids, lignans, phenylpropanoid esters, hydroxycinnamic acid amides, and sporopollenin.Recent studies have revealed that many factors participate in the regulation of phenylpropanoid metabolism, and modulate phenylpropanoid homeostasis when plants undergo successive developmental processes and are subjected to stressful environments. In this review, we summarize recent progress on elucidating the contribution of phenylpropanoid metabolism to the coordination of plant development and plant–environment interaction, and metabolic flux redirection among diverse metabolic routes. In addition, our review focuses on the regulation of phenylpropanoid metabolism at the transcriptional, post-transcriptional, post-translational,and epigenetic levels, and in response to phytohormones and biotic and abiotic stresses.展开更多
Using pulse radiolysis technique, the reaction between hydroxyl radical and 7 phenylpropanoidglycosides: echinacoside, verbascoside, leucosceptoside A, martynoside, pediculariosides A, M and N which were isolated from...Using pulse radiolysis technique, the reaction between hydroxyl radical and 7 phenylpropanoidglycosides: echinacoside, verbascoside, leucosceptoside A, martynoside, pediculariosides A, M and N which were isolated from Pedicularis were examined. The rate constants of these reactions were determined by transient absorption spectra. All 7 phenylpropanoid glycosides react with hydroxyl radical at high rate constants within (0.97-1.91)×1010L · mol-1 · s-1. suggesting that they are effective hydroxyl radical scavengers. The results demonstrate that the numbers of phenolic hydroxyl groups of phenylpropanoid glycosides are directly related to their scavenging activities. The scavenging activities are likely related to o-dihydroxy group of phenylpropanoid glycosides as well.展开更多
基金National Natural Science Foundation of China(Grant No.30873416)
文摘In the present study, we developed and validated a high-performance liquid chromatography method for the simultaneous determination of seven phenylpropanoid compounds （2-hydroxyl cinnamaldehyde, coumarin, cinnamyl alcohol, cinnamic acid, 2-methoxy cinnamic acid, cinnamaldehyde and 2-methoxy cinnamaldehyde） in Cinnamomi Cortex and Cinnamomi Ramulus. The levels of seven phenylpropanoid compounds in Cinnamomi Cortex and Cinnamomi Ramulus were compared using this method. A total of 48 samples （27 Cinnamomi Cortex and 21 Cinnamomi Ramulus） were purchased in China and analyzed. Quantities of seven phenylpropanoid compounds ranged from 17.5 to 61.6 mg/g in Cinnamomi Cortex and ranged from 9.91 to 23.4 mg/g in Ciunamomi Ramulus. The level of 2-methoxy cinnamic acid in the Cinnamomi Cortex samples was below the LOD, whereas it ranged from 0 to 0.119 mg/g in the Cinnamomi Ramulus samples. The （cinnamyl alcohol＋cinnamic acid）/cinnamaldehyde ratios （R346） of Ciunamomi Cortex and Cinnamomi Ramulus ranged from 0.0121 to 0.0467 and 0.0598 to 0.182, respectively. This ratio could be used to discriminate Cinnamomi Cortex （〈0.05） and Cinnamomi Ramulus （〉0.05）. The extraction rates （Dn） of seven compounds in boiling water were different, with the lowest dissolution for cinnamaldehyde （〈3%） and the highest for cinnamic acid （about 60%）.
文摘The regioselective acylation of unprotected phenylethyl glucoside withcinnamoyl chloride leads to 6-OH cin-namoylated glucoside. In this manner, thirteen phenylpropanoidglycoside analogs were designed and prepared. Their structure was confirmed by ~1H NMR and ^(13)CNMR spectra.
文摘A novel phenylpropanoid glycosides 1, named parispolyside E and a novel derivation of phenolic glycoside 2, named parispolyside G, as well as two known flavonoid glycosides were isolated from the rhizome of Paris polyphylla var. yunnanensis. Their structures were elucidaed by spectroscopic methods.
文摘A novel phenylpropanoid glycoside, Callicarposide A has been isolated from the aerial parts of Callicarpa kwangtungensis Chun. The chemical structure is elucidated on the basis of spectral analysis. C 2009 Teng Fei Ji. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
文摘Two new triterpenoid saponins,ardisicrenoside R and S(1 and 2),and one new phenylpropanoid glycoside,ardicrephenin(3),along with five known compounds(4-8),were isolated from roots of Ardisia crenata.Their structures were elucidated on the basis of NMR spectroscopic data and chemical methods.Compounds 2-7 were evaluated for their cytotoxic activities against A549,MCF-7,HepG2 and MDA-MB-231 cell lines by MTT assay.Ardicrenin(6)showed significant cytotoxicity,with IC50 values of 1.17±0.01,1.19±0.06,3.52±0.23,and 16.61±1.02μmol·L^(-1),respectively.
基金Key Projects in Scientific Research of Qujing Normal University(No.2011ZD003)
文摘Two new phenylpropanoid glycosides, 9-O-[6-O-acetyl-β-D-glucopyranosyl]-4-hydroxycinnamic acid （1） and 8-O-β-D-glucopyranosyl-（R）-（＋）-3,4,8-trihydroxy methyl phenylpropionate （2） were isolated from the 80% EtOH extract of the roots of Sanguisorba officinalis. Their slructures were characterized by spectroscopic analysis and chemical method, including 1D NMR, 2D NMR, and HR-ESI-MS. Compounds 1 and 2 exhibited the moderate antimicrobial activities against all Gram-positive and Gram-negative bacteria tested.
基金supported by the National Natural Science Foundation of China(Nos.81001379,U1032602,91013002 and 30725048)the National New Drug Innovation Major Project of China(No.2011ZX09307-002-02)+3 种基金the National Basic Research Program of China(Nos.2009CB522300 and 2013CB127505)the Foundation of Chinese Academy of Sciences(Hundred Talents Program)the Natural Science Foundation of Yunnan Province(No.2012GA 003)the Project Program of State Key Laboratory of Natural Medicines,China Pharmaceutical University(No.ZJ11175)
文摘AIM: To investigate the chemical and bioactive constituents from the stems and leaves of Micromelum integerrimum. METHOD: The chemical constituents were isolated and purified by silica gel, Sephadex LH-20, and HPLC. Their structures were mainly elucidated on the basis of extensive 1D- and 2D-NMR spectroscopy and mass spectrometry. Their cytotoxicity and antimicrobial activities were tested by the SRB and turbidimetric methods, respectively. RESULTS: Two new phenylpropanoids and two known coumarins were obtained, and their structures were identified as microintegerrin A(1), microintegerrin B(2), scopoletin(3), and scopolin(4). All of the compounds were tested for their cytotoxicity against three cancer cell lines(HeLa, A549, and BGC-823) and for antimicrobial activity against the fungus Candida albicans and the bacterium Staphylococcus aureus. CONCLUSION: Two new phenylpropanoids 1 and 2 were isolated and identified from the stems and leaves of M. intgerrimum. None of the compounds showed cytotoxic or antimicrobial activity at the tested concentration of 20 ?g·mL–1.
基金the National Natural Science Foundation of China （No. 20432030） for financial support.
文摘A novel phenylpropanoid-substituted catechin glycoside glabraoside A 1 and a new dihydrochalcone 3＇-（7＂-allylphenyl）-2＇,4＇,4＂-trihydroxy-6＇-methoxydihydrochalcone 2 were isolated from the herbs of Sarcandra glabra. Their structures were elucidated on the basis of spectroscopic analyses and chiroptical methods.
基金National Natural Science Foundation of China! (Grant No. 29772039)
文摘A new phenylpropanoid glycoside, serratumoside A, was isolated from the aerial parts of Clerodendrum serratum var. amplexifolium Moldenke. Its structure was determined by spectral and chemical methods.
文摘Peaches are subject to flesh softening during postharvest storage and transport,which affects the storage life of the fruit and causes huge economic losses.Previous research has demonstrated that postharvest brassinolide treatment can maintain flesh firmness,ascorbic acid and soluble solids contents,and enhance disease resistance in peach fruits.This study assessed the influence of postharvest brassinolide treatment on the expression of key genes involved in cell wall degradation and the phenylpropanoid pathway in peach fruits by real-time fluorescence quantitative polymerase chain reaction(qPCR).The results showed that brassinolide dipping inhibited the gene expression of pectate lyase 1,polygalacturonase 21 and pectin methylesterase 1,and significantly enhanced the gene expression of peroxidase,cinnamoyl-CoA reductase,phenylalanine ammonia lyase and caffeoyl-CoA-O-methyltransferase 5 in peach fruits.It also increased the gene expression levels of chaleone synthase,chaleone isomerase,dihydroflavonol-4-reductase and flavanone 3-hydroxylase at the early stage of storage.These findings imply that brassinolide can suppress the expression of key genes involved in cell wall degradation and enhance the expression of key genes involved in the phenylpropanoid pathway,thereby delaying peach fruit softening and enhancing disease resistance.
文摘In the present paper are discussed the results of the investigations of the phenylpropanoids of the medicinal plants which are of the great interest as the sources of the neurotropic, adaptogenic, immunostimulating, antioxidative, and hepatoprotective preparations. There were shown the necessity of using of the standard samples of triandrin (Rhodiola rosea L. tissue cultures, Salix viminalis L. barks), rosavin (Rhodiola rosea L. rhizomes), syringin, or eleutheroside B [Eleutherococcus senticosus (Rupr. et Maxim.) Maxim. rhizomes, Syringa vulgaris L. barks], and silybin [Silybum marianum (L.) Gaertn. fruits] for purpose of the standardization of the corresponding drugs and pharmaceuticals. It was shown also the significance of γ-schizandrin, chicoric acid, rosmarinic acid and lavandoside for purposes of the standardization of raw material and preparations of Schizandra chinensis Baill. fruits and seeds, Echinacea purpurea (L.) Moench. herbs, Melissa officinalis L. herbs and Lavandula spica L. flowers respectively.
文摘The role of lignifications and enzymes involved in the phenylpropanoid (PP) biosynthesis i.e. phenylalanine ammonia lyase (PAL), Peroxidase (POD), Polyphenol oxidase (PPO) in providing resistance to Karnal Bunt (KB) during different developmental stages of resistant (HD-29) and susceptible genotype (WH-542) and its recombinant inbred lines (RILs) of wheat were investigated. The enzymes of PP pathway were expressed constitutively in both the susceptible and resistant genotype. However, the activity was higher in all the developmental stages of resistant genotype and its RILs, indicating that this genotype has a significant higher basal level of these enzymes as compared to the susceptible line and could be used as marker(s) to define KB resistance. The activity of PAL and POD was significantly higher in WSv stage (Z = 16) while the specific activity of PPO was higher in WS3 (Z = 77) stage as compared to the other physiological stages in both the genotypes. In resistant genotype the lignin content increased two-fold and three-fold at WS2 and WS3 stage, respectively, while in susceptible genotype no significant increase in lignin content was observed. The pathway might be associated with the enhancement of structural defense barrier due to lignifications of cell wall as evident from the enhanced synthesis of lignin in all the stages of resistant genotype. Our results clearly indicate the possible role of enzymes of PP metabolism provides genotype and stage dependant structural barrier resistance in wheat against KB.
基金supported by the Southeast Asia Biodiversity Research Institute,Chinese Academy of Sciences(2015CASEABRIRG001 and Y4ZK111B01)the open foundation of Key Laboratory of Ethnomedicine(Minzu University of China),Ministry of Education(KLEM-KF2018Z01)the International Partnership Program of Chinese Academy of Sciences(153631KYSB20160004).
文摘Two new amides(E)-N-cinnamoyl-2-methoxypiperidine(1)and(R)-1-(2-oxopyrrolidin-3-yl)-5,6-dihydropyridin-2(1H)-one(2),four new amide glucosides,retrofractosides A-D(3-6),and two new phenylpropanoid glucosides,retrofractosides E(7)and F(8),together with 24 known compounds(9-32)were isolated from the fruits of Piper retrofractum.The chemical structures of these new compounds were elucidated based on extensive spectroscopic analysis.All of these isolates(1-32)were evaluated for inhibitory activity against mouse platelet aggregation induced by the peptide AYPGKF-NH2.(E)-N-(Tetrahydro-2H-pyran-2-yl)cinnamamide(9)showed a weak inhibitory efect,with an inhibition ratio of 52.0%at a concentration of 150μM.
基金supported by the PUMC(Peking Union Medical College)Youth Fund(3332015142) National Natural Science Foundation of China(81703746)
文摘OBJECTIVE To explore the hypolipidemic mechanisms of the total phenylpropanoid glycosides fromLigustrum robustum(Roxb.) Blume(LRTPG) in hamsters using proteomics technique.METHODS The hamsters were fed with a high fat diet to induce hyperlipidemia.Then LRTPG of high(1.2 g·kg^(-1)),medium(0.6 g·kg^(-1)) and low(0.3 g·kg^(-1)) doses were administrated daily for 4 weeks.Then the concentrations of plasma and hepatic lipids were determined using enzymic methods.The total protein was extracted from livers of the model group and the group treated with the high dose of LRTPG for label-free quantitative proteomics.RESULTS LRTPG significantly reduced the concentrations of plasma and hepatic lipids in hamsters fed a high fat diet.The proteomics data showed that a total of 2231 proteins were identified,and 549 proteins were found to be differentially expressed between the model group and the group treated with LRTPG.Among the 549 proteins,93 proteins were up-regulated and 59 proteins were down-regulated,and 397 proteins were absent or not.And some of these proteins were much related to the lipid metabolism.Further,gene ontology(GO) analysis indicated metabolic process,transport,oxidation-reduction process,phosphorylation,signal transduction,lipid metabolic process were the main biological processes that those differentially expressed proteins participated.KEGG pathway analysis showed that those proteins were involved in several metabolic pathways including oxidative phosphorylation,non-alcoholic fatty liver disease(NAFLD),PI3K-Akt signaling pathway,cAMP signaling pathway,cGMP-PKG signaling pathway.CONCLUSION The proteomics study could provide valuable clues to help us to understand the hypolipidemic mechanisms of LRTPG much better.
文摘Our continued interest in the research and development of cosmetic active ingredients deriving from natural sources led us to investigate the potential of a purified extract of Ajuga reptans, a plant belonging to the family Labiatae and known for its traditional use in skin healing. The extracts deriving from a biotechnology platform are composed by meristematic cell culture, developed in the frame of a NTFP (non-timber forest product) project, and characterized by high content in phenylpropanoid, of which teupolioside represents the majority component. The latter is a phenylpropanoid glucoside, structurally correlated echinacoside and known in the literature for the antioxidant properties. This study was conducted with the purpose of evaluating the applicability of the Ajuga reptans extract within different cosmetic formulations. In particular, Photochemiluminescence (PCL) was used to proof the antioxidant capacity of cosmetic formulations containing the product, in relation to the change of the title of teupolioside. Furthermore, UVA and UVB filtering properties were also investigated. The results of the study showed relevantly antioxidant capacity of the finished formulation against superoxide anion, which is the main reactive oxygen species responsible for skin aging and significant synergic capacities to filter UV radiation.
基金financially supported by the Program for New Century Excellent Talents in University, State Education Ministry of China (No. NCET2008-0224)the National Natural Science Foundation of China (Nos. 31370372, 81573316, 31570361, 31200258)
文摘Two pairs of chlorine-containing phenylpropanoid enantiomers（1a/1b and 2a/2b） were isolated from the rhizomes of Acorus tatarinowii. Interestingly, these optical isomers（1a/1b and 2a/2b） were co-existed in the same plant, which were characterized as the first halogen-containing natural products from the genus Acorus. Their structures and absolute configurations were elucidated by a combination of spectroscopic analysis and a single-crystal X-ray diffraction, assisted by a modified Mosher＇s method. The phenylpropanoid isomers（1a/1b and 2a/2b） were evaluated for their antioxidant activities using DPPH assay and cytotoxic activities against five human cancer cell lines.
文摘The general phenylpropanoid metabolism generates an enormous array of secondary metabolites based on the few intermediates of the shikimate pathway as the core unit. The resulting hydroxycinnamic acids and esters are am- plified in several cascades by a combination of reductases, oxygenases, and transferases to result in an organ and devel- opmentally specific pattern of metabolites, characteristic for each plant species. During the last decade, methodology driven targeted and non-targeted approaches in several plant species have enabled the identification of the participating enzymes of this complex biosynthetic machinery, and revealed numerous genes, enzymes, and metabolites essential for regulation and compartmentation. Considerable success in structural and computational biology, combined with the an- alytical sensitivity to detect even trace compounds and smallest changes in the metabolite, transcript, or enzyme pattern, has facilitated progress towards a comprehensive view of the plant response to its biotic and abiotic environment. Trans- genic approaches have been used to reveal insights into an apparently redundant gene and enzyme pattern required for functional integrity and plasticity of the various phenylpropanoid biosynthetic pathways. Nevertheless, the function and impact of all members of a gene family remain to be completely established. This review aims to give an update on the various facets of the general phenylpropanoid pathway, which is not only restricted to common lignin or flavonoid biosynthesis, but feeds into a variety of other aromatic metabolites like coumarins, phenolic volatiles, or hydrolyzable tannins.
基金Supported by the Hi-Tech Research and Development Program of China(2006AA10Z184)the National Natural Science Foundation of China(30660088)+1 种基金the Hi-Tech Research and Development Program of Xinjiang,China (200611101)Postdoctoral Foundation of Xinjiang Academy of Agricultural Sciences
文摘The mature cotton （Gossypium hirsutum L.） fiber is a single cell with a typically thickened secondary cell wall. The aim of this research was to use molecular, spectroscopic and chemical techniques to investigate the possible occurrence of previously overlooked accumulation of phenolics during secondary cell wall formation in cotton fibers. Relative quantitative reverse transcription-polymerase chain reaction analysis showed that GhCAD6 and GhCAD1 were predominantly expressed among seven gene homologs, only GhCAD6 was up-regulated during secondary wall formation in cotton fibers. Phylogenic analysis revealed that GhCAD6 belonged to Class I and was proposed to have a major role in monolignol biosynthesis, and GhCAD1 belonged to Class III and was proposed to have a compensatory mechanism for monolignol biosynthesis. Amino acid sequence comparison showed that the cofactor binding sites of GhCADs were highly conserved with high similarity and identity to bona fide cinnamyl alcohol dehydrogenases. The substrate binding site of GhCAD1 is different from GhCAD6. This difference was confirmed by the different catalytic activities observed with the enzymes. Cell wall auto-fluorescence, Fourier transform infrared spectroscopy （FTIR）, high-performance liquid chromatography （HPLC） and chemical analyses confirmed that phenolic compounds were bound to the cell walls of mature cotton fibers. Our findings may suggest a potential for genetic manipulation of cotton fiber properties, which are of central importance to agricultural, cotton processing and textile industries.
基金supported by the grants from National Natural Science Foundation of China (31788103,31630052)the Chinese Academy of Sciences (QYZDY-SSWSMC023, XDB27010104, 159231KYSB20200008)+2 种基金the Ministry of Science and Technology of China (2016YFD0100902)the Shanghai Science and Technology Development(18JC1415000)the support of the SA-SIBS scholarship program。
文摘Phenylpropanoid metabolism is one of the most important metabolisms in plants, yielding more than 8,000 metabolites contributing to plant development and plant-environment interplay.Phenylpropanoid metabolism materialized during the evolution of early freshwater algae that were initiating terrestrialization and land plants have evolved multiple branches of this pathway, which give rise to metabolites including lignin, flavonoids, lignans, phenylpropanoid esters, hydroxycinnamic acid amides, and sporopollenin.Recent studies have revealed that many factors participate in the regulation of phenylpropanoid metabolism, and modulate phenylpropanoid homeostasis when plants undergo successive developmental processes and are subjected to stressful environments. In this review, we summarize recent progress on elucidating the contribution of phenylpropanoid metabolism to the coordination of plant development and plant–environment interaction, and metabolic flux redirection among diverse metabolic routes. In addition, our review focuses on the regulation of phenylpropanoid metabolism at the transcriptional, post-transcriptional, post-translational,and epigenetic levels, and in response to phytohormones and biotic and abiotic stresses.
基金Project partly supported by the National Natural Science Foundation of China and partly by Open Laboratory of Radiation Chemistry, the Chinese Academy of Sciences.
文摘Using pulse radiolysis technique, the reaction between hydroxyl radical and 7 phenylpropanoidglycosides: echinacoside, verbascoside, leucosceptoside A, martynoside, pediculariosides A, M and N which were isolated from Pedicularis were examined. The rate constants of these reactions were determined by transient absorption spectra. All 7 phenylpropanoid glycosides react with hydroxyl radical at high rate constants within (0.97-1.91)×1010L · mol-1 · s-1. suggesting that they are effective hydroxyl radical scavengers. The results demonstrate that the numbers of phenolic hydroxyl groups of phenylpropanoid glycosides are directly related to their scavenging activities. The scavenging activities are likely related to o-dihydroxy group of phenylpropanoid glycosides as well.
