Pinocembrin Chalcone Research Articles

The variability of terpenoids and flavonoids in native Lindera umbellata from the same region

The leaves and twigs of Lindera spp. have long been used as a herbal medicine and toothpicks in Japan. However, little is known about individual variations in the extractives of these species, because many previous studies have not distinguished extractives between individuals. In this study, we investigated the extractives of L. umbellata at the individual level. The detailed identification of the inter- and intra-individual variations in the major terpenoids and flavonoids in native L. umbellata may greatly contribute to the development of cultivation techniques and the effective use of forest resources. The contents of major components of L. umbellata, including four terpenoids (1,8-cineole, linalool, geraniol, and geranyl acetate) and five low-molecular-weight phenolics (pinocembrin chalcone, pinocembrin, pinostrobin chalcone, pinostrobin, and 5,6-dehydrokawain), were analyzed in leaves and twigs seasonally (June, August, and October). The compositions of the major terpenoids were strongly dependent on the properties of each individual and were generally independent of leaves and twigs. Moreover, geranyl acetate was characteristically present in the twigs of some individuals. As new findings regarding linalool, some individuals showed characteristic enantiomeric excesses, presumably because of biotic factors, and the proportion of these enantiomers was kept constant in each individual, regardless of the season. The total phenolic contents in leaves were more than twice those detected in twigs, and the leaves tended to contain more chalcones and twigs more flavanones. Furthermore, the contents of chalcones (pinocembrin chalcone vs. pinostrobin chalcone) and flavanones (pinocembrin vs. pinostrobin) were positively correlated in both leaves and twigs. The coefficient of variation (CV) clearly showed that the content of the major terpenoids was determined by inter-individual rather than intra-individual differences. Although the results obtained in this study should at present only be applicable to a limited population native to specific regions, our findings provide key knowledge in considering the sustainable use of L. umbellata.

ACTIVITY STUDY OF KAEMPFERIA PANDURATA ROXB. EXTRACT AS ANTIESTROGEN RECEPTOR (-) BREAST CANCER CELL LINE 3,4-METHYLENEDIOXYAMPHETAMINE-MB-231 BY MOLECULAR DOCKING AND 3-(4,5-DIMETHYLTHIAZOL-2-YL)-2, 5-DIPHENYLTETRAZOLIUM BROMIDE ASSAY

This research was determined the cytotoxic activity of extract the rhizomes of Kaempferia pandurata as anti-breast cancer in 3,4-methylenedioxyamphetamine (MDA)-MB-231 cell line by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay and study of estrogen receptor (ER) negative with target vascular endothelial growth factor (VEGF) by molecular docking approach. Materials and Methods: The docking study was conducted using AutoDock Vina. The macromolecule was retrieved from protein data bank (PDB), with ID code 2OH4 and saved in PDB format. The ligands were prepared using Marvin Sketch and saved in.PDB format. The next step was in vitro assay of the extract against MDA-MB-231 cell line using MTT test. From this assay, we will get the half maximal inhibitory concentration (IC50) value of extract. Results: Compounds pinostrobin and pinocembrin have the lowest Gibbs energy and Ki values, even lower compared to gossypol, which means that this molecule is most active when bound to VEGF. The hydrogen bonds that occur between the pinostrobin and the receptor are similar to the hydrogen bonds that are present between gossypol and its receptor, called Phe1045, Val846, Leu1033, and Cys917. This amino acid as active site of VEGF. The IC50 value of standard cisplatin, doxorubicin, and hexane extract was 18.4, 1.24, and 20.54 μg/ml, respectively. Hexane extracts of K. pandurata demonstrated antiproliferative activities. Conclusion: The extract rhizomes of K. pandurata with pinostrobin and pinocembrin chalcone as major compounds showed potent activity as anticancer against breast cancer cell line.

In vitro and in silico studies of chalcone synthase variant 2 in Boesenbergia rotunda and its substrate specificity.

In this study, transformation of BrCHS var 2 into B. rotunda cell suspension culture, followed by chalcone synthase enzymatic assay and HPLC analysis was conducted to investigate whether the substrate specificity for BrCHS var 2 is either cinnamoyl-CoA or p-coumaroyl-CoA. The HPLC profile showed an increase in the amount of pinocembrin chalcone when cinnamoyl-CoA and malonyl-CoA were added but not p-coumaroyl-CoA. Molecular docking was performed to explore the binding of cinnamoyl-CoA and p-coumaroyl-CoA to BrCHS var 2 receptor and the docking results showed that cinnamoyl-CoA formed numerous hydrogen bonds and more negative docked energy than p-coumaroyl-CoA. Cinnamoyl-CoA showed good interactions with Cys 164 to initiate the subsequent formation of pinocembrin chalcone, whereas the hydroxyl group of p-coumaroyl-CoA formed an unfavorable interaction with Gln 161 that caused steric hindrance to subsequent formation of naringenin chalcone. Docked conformation analysis results also showed that malonyl-CoA formed hydrogen bonding with Cys 164, His 303, and Asn 336 residues in BrCHS var 2. The results show that cinnamoyl-CoA is the preferred substrate for BrCHS var 2.

Characterization of three chalcone synthase-like genes from apple (Malus x domestica Borkh.)

Apple (Malus x domestica Brokh.) is a widely cultivated deciduous tree species of significant economic importance. Apple leaves accumulate high levels of flavonoids and dihydrochalcones, and their formation is dependent on enzymes of the chalcone synthase family. Three CHS genes were cloned from apple leaves and expressed in Escherichia coli. The encoded recombinant enzymes were purified and functionally characterized. In-vitro activity assays indicated that MdCHS1, MdCHS2 and MdCHS3 code for proteins exhibiting polyketide synthase activity that accepted either p-dihydrocoumaroyl-CoA, p-coumaroyl-CoA, or cinnamoyl-CoA as starter CoA substrates in the presence of malonyl-CoA, leading to production of phloretin, naringenin chalcone, and pinocembrin chalcone. MdCHS3 coded a chalcone-dihydrochalcone synthase enzyme with narrower substrate specificity than the previous ones. The apparent Km values of MdCHS3 for p-dihydrocoumaryl-CoA and p-coumaryl-CoA were both 5.0 μM. Expression analyses of MdCHS genes varied according to tissue type. MdCHS1, MdCHS2 and MdCHS3 expression levels were associated with the levels of phloretin accumulate in the respective tissues.

Study of Chemical Composition and Efficacy of Different Extracts of Iranian Propolis on the Microbiological and Sensory Parameters of Minced Cyprinus carpio Meat at 4°C Storage

ABSTRACTThis study has evaluated the effects of different concentrations of the water and ethanolic extracts of Iranian propolis (WEP and EEP) on the microbiological and sensory parameters of minced common carp meat that was stored at 4°C for 9 days. The chemical compounds of the extracts were identified by gas chromatography–mass spectroscopy (GC-MS) analysis. The results revealed that WEP and EEP extracts were efficient against the spoilage microorganisms, including total plate counts (TPCs), psychrotrophic populations (PTCs), lactic acid bacteria (LAB), and even Staphylococcus aureus. There was a significant difference in the bacteria growth between samples treated with WEP or EEP and the control sample during storage. Inhibitory effects were, respectively, 7% EEP > 5% EEP > 3% EEP > 7% WEP > 5% WEP > 3% WEP. In all treatments, PTC counts were higher than 7 log CFU/g after 6 days as well as TPC, LAB, and S. aureus populations after 9 days. Overall, the results show that EEP and WEP have good antimicrobial activity due to high phenolic and flavonoid compounds, including caffeic acid, tectochrysin, aceacetin, chrysin, pinostrobin, pinobanksin-3-acetate, galangin-3-methyl ester, and pinocembrin chalcone. Sensory evaluation shows very slight improvement in sensory properties (color, odor, texture, and overall acceptability) of the treated samples with the different extracts of Iranian propolis.

Flavonoids and alkaloids from the leaves of Litsea fruticosa

Phytochemical investigation of Litsea fruticosa (Hemsl.) Gamble resulted in the isolation of eight flavonoids and four alkaloids. Their structures were identified as pinostrobin, pinocembrin, pinocembrin chalcone, apigenin, kaempferol, astragalin, isoquercetin, kaempferol 3,4′-di-O-l-rhamnopyranoside, boldine, laurolitsine, actinodaphnine and ushinsunine by comparison of their spectral data with those reported previously in the literature. Chemotaxonomic significance of these investigation is summarized.

Preparation of flavonoids and diarylheptanoid from Alpinia katsumadai hayata by microwave-assisted extraction and high-speed counter-current chromatography

In the present work, five flavonoids and diarylheptanoid, namely, alpinetin, pinocembrin chalcone, pinocembrin, cardamomin and 1,7-diphenyl-4,6-heptadien-3-one, were simply and rapidly prepared from Alpinia katsumadai hayata ( A. katsumadai) by microwave-assisted extraction (MAE) followed with high-speed counter-current chromatography (HSCCC). The critical conditions of MAE and HSCCC were optimized. 2.0 g crude sample was extracted with MAE, and then directly separated and purified by HSCCC with a two-phase solvent system composed of hexane–ethyl acetate–methanol–water (3:7:6:4, v/v/v/v), and 7.5 mg of alpinetin, 1.9 mg of pinocembrin chalcone, 2.6 mg of 1,7-diphenyl-4,6-heptadien-3-one with purities of 98.3%, 96.9% and 93.0% were obtained respectively in a single step within 4 h. 4.0 mg mixture of cardamomin and pinocembrin from HSCCC was further separated by prep-HPLC, 2.1 mg of 99.4% pinocembrin and 1.4 mg of 99.8% cardamomin were obtained respectively. The purities of compounds were determined by HPLC and their chemical structures were further identified by ESI-MS and 1H NMR. The results demonstrated that MAE coupled with HSCCC was a feasible, economical and efficient technique for rapid extraction, separation and purification of effective compounds in natural products.

Antimicrobial Activity of Flavonoids From Piper lanceaefolium and Other Colombian Medicinal Plants Against Antibiotic Susceptible and Resistant Strains of Neisseria gonorrhoeae

The successful treatment of Neisseria gonorrhoeae (NG) infections is increasingly problematic because of the resistance of this pathogen to multiple antimicrobial agents. This development underscores the need for new antimicrobial sources. In the current study, 21 crude methanol extracts, from 19 plants used in Colombian traditional medicine for cutaneous infections, were screened for antimicrobial activity against NG. Extracts were screened by disc susceptibility assay. In addition, the minimum inhibitory concentrations of active compounds from P. lanceaefolium were assayed using a panel of 26 NG strains comprising 12 antibiotic-resistant phenotypes. In all, 71% of the crude extracts exhibited antibacterial activity against the antibiotic susceptible NG strain WHO V, whereas 10% of the extracts inhibited penicillinase-producing NG strain GC1-182. The crude extract of Piper lanceaefolium was the only extract to show significant activity without ultraviolet (UV) light activation. Preliminary screening identified 3 compounds in this plant possessing antimicrobial activity: the flavonoids 5,7-dihydroxyflavanone (pinocembrin), 2',4',6'-trihydroxychalcone (pinocembrin chalcone), and the prenylated benzoic acid derivative cyclolanceaefolic acid methyl ester. Pinocembrin and pinocembrin chalcone inhibited 100% of the NG panel at 64 μg/mL and 128 μg/mL, respectively, whereas cyclolanceaefolic acid methyl ester inhibited 44% of the strains at 128 μg/mL. This is the first report of the antibacterial activity of Columbian plants against NG. The activity of the 2 flavonoids, pinocembrin, and pinocembrin chalcone, toward both susceptible and resistant NG strains makes them promising candidates for further research.

Pinostrobin fromBoesenbergia pandurataIs an Inhibitor of Ca2+-Signal-Mediated Cell-Cycle Regulation in the YeastSaccharomyces cerevisiae

Upon searching plant extracts for inhibitors of the Ca(2+) signaling pathway using the zds1Delta-yeast proliferation based assay, a crude rhizome extract of Boesenbergia pandurata was found to be strongly positive, and from this extract pinostrobin, alpinetin, and pinocembrin chalcone were isolated as active components. Further biochemical experiments confirmed that pinostrobin possesses inhibitory activity on the Ca(2+) signals involved in the control of G2/M phase cell cycle progression in Saccharomyces cerevisiae.

Metabolic engineering of the phenylpropanoid pathway in Saccharomyces cerevisiae.

Flavonoids are valuable natural products derived from the phenylpropanoid pathway. The objective of this study was to create a host for the biosynthesis of naringenin, the central precursor of many flavonoids. This was accomplished by introducing the phenylpropanoid pathway with the genes for phenylalanine ammonia lyase (PAL) from Rhodosporidium toruloides, 4-coumarate:coenzyme A (CoA) ligase (4CL) from Arabidopsis thaliana, and chalcone synthase (CHS) from Hypericum androsaemum into two Saccharomyces cerevisiae strains, namely, AH22 and a pad1 knockout mutant. Each gene was cloned and inserted into an expression vector under the control of a separate individual GAL10 promoter. Besides its PAL activity, the recombinant PAL enzyme showed tyrosine ammonia lyase activity, which enabled the biosynthesis of naringenin without introducing cinnamate 4-hydroxylase (C4H). 4CL catalyzed the conversion of both trans-cinnamic acid and p-coumaric acid to their corresponding CoA products, which were further converted to pinocembrin chalcone and naringenin chalcone by CHS. These chalcones were cyclized to pinocembrin and naringenin. The yeast AH22 strain coexpressing PAL, 4CL, and CHS produced approximately 7 mg liter(-1) of naringenin and 0.8 mg liter(-1) of pinocembrin. Several by-products, such as 2',4',6'-trihydroxydihydrochalcone and phloretin, were also identified. Precursor feeding studies indicated that metabolic flux to the engineered flavonoid pathway was limited by the flux to the precursor l-tyrosine.

Expression of the Chalcone Synthase Gene in Scutellaria baicalensis Hairy Root Cultures Was Unusually Reduced by Environmental Stresses.

A cDNA clone, named as SbCHS cDNA, encoding chalcone synthase (CHS, EC 2.3.1.74) was isolated from a cDNA library derived from hairy root cultures of Scutellaria baicalensis Georgi by screening with a 1.4 kbp full length CHS cDNA of Phaseolus vulgaris as the probe. Complete nucleotide sequence of the SbCHS cDNA contained 1170-base pair open reading frame encoding 390 amino acid residues. The deduced amino acid sequence of SbCHS cDNA exhibited 82.1% identity with CHS of P. vulgaris. SbCHS mRNA expression in S. baicalensis hairy roots was unusually reduced by UV light irradiation, wounding, and yeast extract, as shown by Northern blot analysis. Greater formation of naringenin chalcone (100%) than of pinocembrin chalcone (67.4%) was observed by using thin-layer chromatography (TLC) to assess the enzymatic activity of recombinant SbCHS expressed in Escherichia coli.

Antifungal activity of benzoic acid derivatives from Piper lanceaefolium.

Bioactivity-guided fractionation of a methanol extract from the leaves of Piper lanceaefolium resulted in the isolation of four new benzoic acid derivatives (1-4), together with taboganic acid, pinocembrin, and pinocembrin chalcone. Lanceaefolic acid methyl ester (3) and pinocembrin chalcone displayed activity against Candida albicans with a minimal inhibitory concentration value of 100 microg/mL in both cases.

Structural analysis of a novel antimutagenic compound, 4-Hydroxypanduratin A, and the antimutagenic activity of flavonoids in a Thai spice, fingerroot (Boesenbergia pandurata Schult.) against mutagenic heterocyclic amines.

Six compounds were isolated from fresh rhizomes of fingerroot (Boesenbergia pandurata Schult.) as strong antimutagens toward 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole (Trp-P-1) in Salmonella typhimurium TA98. These compounds were 2',4',6'-trihydroxychalcone (pinocembrin chalcone; 1), 2',4'-dihydroxy-6'-methoxychalcone (cardamonin; 2), 5,7-dihydroxyflavanone (pinocembrin; 3), 5-hydroxy-7-methoxyflavanone (pinostrobin; 4), (2,4,6-trihydroxyphenyl)-[3'-methyl-2'-(3' '-methylbut-2' '-enyl)-6'-phenylcyclohex-3'-enyl]methanone (5), and (2,6-dihydroxy-4-methoxyphenyl)-[3'-methyl-2'-(3' '-methylbut-2' '-enyl)-6'-phenylcyclohex-3'-enyl]methanone (panduratin A; 6). Compound 5 was a novel compound (tentatively termed 4-hydroxypanduratin A), and 1 was not previously reported in this plant, whereas 2-4 and 6 were known compounds. The antimutagenic IC(50) values of compounds 1-6 were 5.2 +/- 0.4, 5.9 +/- 0.7, 6.9 +/- 0.8, 5.3 +/- 1.0, 12.7 +/- 0.7, and 12.1 +/- 0.8 microM in the preincubation mixture, respectively. They also similarly inhibited the mutagenicity of 3-amino-1-methyl-5H-pyrido[4,3-b]indole (Trp-P-2) and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP). All of them strongly inhibited the N-hydroxylation of Trp-P-2. Thus, the antimutagenic effect of compounds 1-6 was mainly due to the inhibition of the first step of enzymatic activation of heterocyclic amines.

Phenolic Composition of Bud Exudates of Populus deltoides

Abstract Bud exudate of Populus deltoides clones originating from six central and eastern American states was examined by gas chromatography/mass spectrometry and the components were identified. The principal components of the bud exudate were the flavone galangin, the flavanone pinocembrin and the flavanonol pinobanksin, together with the related compounds pinocembrin chalcone, pinobanksin methyl ether and pinobanksin-3-acetate. The bud exudate composition was very different from that seen in a North American poplar of the section Tacamahaca, P. balsamifera. The bud exudates from all P. deltoides specimens were similar excepting that from Vermont.