Eupalitin

Ethnomedicinal uses, phytochemistry and pharmacological properties of the genus Boerhavia.[Pubmed:26844923]

J Ethnopharmacol. 2016 Apr 22;182:200-20.

ETHNOPHARMACOLOGICAL RELEVANCE: The genus Boerhavia is widely distributed in tropical, subtropical and temperate regions of the world including Mexico, America, Africa, Asia, Indian Ocean Islands, Pacific Islands and Australia. The genus Boerhavia is extensively used by local peoples and medicinal practitioners for treatments of hepatitis, urinary disorders, gastro intestinal diseases, inflammations, skin problems, infectious diseases and asthma. Present review focused on traditional uses, phytochemistry, pharmacology and toxicology of Boerhavia genus to support potential scope for advance ethnopharmacological study. MATERIALS AND METHODS: Information on the Boerhavia species was collected from classical books on medicinal plants, pharmacopoeias and scientific databases like PubMed, Scopus, GoogleScholar, Web of Science and others. Also scientific literatures based on ethnomedicinal surveys, Ph.D. and M.Sc. dissertations, published papers from Elsevier, Taylor and Francis, Springer, ACS as well as Wiley publishers and reports by government bodies and documentations were assessed. RESULTS: A total of 180 compounds from Boerhavia genus were isolated of which B. diffusa alone shared around 131 compounds and for most of which it is currently an exclusive source. In the genus, phenolic glycosides and flavonoids contribute approximately 97 compounds. These includes Eupalitin, rotenoids like boeravinones, coccineons, alkaloid i.e. betanin and punarnavine etc., showing vital pharmaceutical activities such as anticancer, anti-inflammatory, antioxidant and immunomodulatory. CONCLUSION: Boerhavia is an important genus with wide range of medicinal uses. However, most of the available scientific literatures have lacked relevant doses, duration and positive controls for examining bioefficacy of extracts and its active compounds. In some studies, taxonomic errors were encountered. Moreover, there is need for accurate methods in testing the safety and ethnomedicinal validity of Boerhavia species.

Eupalitin induces apoptosis in prostate carcinoma cells through ROS generation and increase of caspase-3 activity.[Pubmed:26493029]

Cell Biol Int. 2016 Feb;40(2):196-203.

Prostate cancer is the second most common malignancy in the human reproductive system. Eupalitin is one of the O-methylated flavonol-exhibited enhanced cancer chemopreventive agents. The current study highlights the structural determination of Eupalitin and aims to explore the antitumor activity of Eupalitin in human prostate cancer cell (PC3) and its underlying mechanism. Eupalitin structure was determined by using FTIR, (1)H NMR, and (13)C NMR. PC3 cells were treated with increasing concentrations of Eupalitin, followed by analysis of the cell viability with an MTT assay. The results demonstrated that Eupalitin markedly inhibited the proliferation of PC3 cells in a concentration-dependent manner. The results from fluorescent microscopic analysis of nuclear condensation and intracellular ROS generation determined that Eupalitin significantly induced ROS level lead to nuclear apoptosis. Cell cycle analysis revealed that Eupalitin-induced cell cycle progression as a percentage of cells in G0/G1 phase decreased whereas S phase increased. Caspase-3 immunofluorescence analysis confirms the efficacy of Eupalitin-inducing apoptotic pathway and cell death. Thus, our study is helpful in understanding the mechanism underlying these effects in prostate cancer and it may provide novel molecular targets for prostate cancer therapy.

Advances in Boerhaavia diffusa hairy root technology: a valuable pursuit for identifying strain sensitivity and up-scaling factors to refine metabolite yield and bioactivity potentials.[Pubmed:26315820]

Protoplasma. 2016 Jul;253(4):1145-58.

The present study reports the Agrobacterium rhizogenes-mediated hairy root induction in of an ethno-medicinally significant herb-Boerhaavia diffusa L., for elucidating the underlying competence regarding its biosynthetic (i.e. boeravinone B and Eupalitin) and bioactivity (antibacterial, antioxidant and anti-inflammatory) potentials. Host plant-specific receptiveness towards A. rhizogenes strains and disparity in compatibility threshold of leaf and nodal explants were evident. Only leaf explants responded, attaining hairy root induction with the ATCC 15834 followed by A4 and SA79 strains in reducing order of transformation efficiency. The growth behaviours differed amongst independent rhizoclones, and two clones of A4 (RBH) and ATCC 15834 (RBT8) origin demonstrated higher growth potentials. Polymerase chain reaction amplification of rol genes confirmed their transformed nature. Optimization of the appropriate solvent and reverse phase high-performance liquid chromatography parameters relating to the targeted metabolite production in the selected RBH and RBT8 clones revealed higher accumulation of Eupalitin with the RBH clone having the best result of 1.44 times greater yield over the control root. Compared to the selected rhizoclones, the control roots however showed higher boeravinone B content. Devising a modified "stirred-tank" reactor through equipping with marine impellers and ring spargers facilitated high-density RBH root biomass yield with 6.1-fold and 1.15-fold yield increment of the boeravinone B and Eupalitin respectively compared to shake-flask cultures. Considering the control roots, the RBH clone revealed analogous antioxidant/antibacterial activities with improved anti-inflammatory potential. The hairy root mediated higher production of boeravinone B and Eupalitin could be achieved for the first time in bioreactor.

Densitometric Validation and Optimisation of Polyphenols in Ocimum sanctum Linn by High Performance Thin-layer Chromatography.[Pubmed:25676726]

Phytochem Anal. 2015 Jul-Aug;26(4):237-46.

INTRODUCTION: Ocimum sanctum Linn (Sanskrit: Tulasi; family: Libiaceae), popularly known as holy basil or Ocimum teinufolium, is found throughout the semitropical and tropical parts of India. In Ayurveda, Tulasi has been well known for its therapeutic potentials. OBJECTIVE: To optimise and develop a standard method to quantify seven polyphenols simultaneously by HPTLC. METHODS: A three-level factor Box-Behnken statistical design was used for optimisation, where extraction time (min), temperature ( degrees C) and methanol:water ratio (% v/v) are the independent variables with polyphenols as the dependent variable. The separation was archived on a silica-gel 60 F254 HPTLC plate using toluene:ethyl acetate:formic acid:methanol (3:3:0.8:0.2 v/v) as the mobile phase. Densitometric analysis of polyphenols was carried out in the absorbance mode at 366 nm. RESULTS: The quantification of polyphenols was carried out based on peak area with a linear calibration curve at concentration ranges of 60-240, 20-200, 100-1600, 40-200, 200-1400, 10-160, 200-1400, 100-5000 ng/band for caffeic acid, ellagic acid, rutin, kaempferol, catechin, quercetin, Eupalitin and epicatechin respectively. The method was validated for peak purity, precision, accuracy, limit of detection (LOD) and quantification (LOQ). Method specificity was confirmed using the retention factor value and visible spectra correlation of marker compounds. CONCLUSIONS: A validated HPTLC method was newly developed for simultaneous quantification of seven polyphenols in an Ayurvedic preparation of O. sanctum. The proposed method is simple, precise, specific, accurate, cost-effective, less time consuming and has the ability to separate the polyphenols from other constituents.

Phytochemical profile and bioactivity of traditional ayurvedic decoctions and hydro-alcoholic macerations of Boerhaavia diffusa L. and Curculigo orchioides Gaertn.[Pubmed:25612143]

Nat Prod Res. 2015;29(22):2071-9.

Decoctions (DECs) and hydro-alcoholic extracts (HEs) prepared from roots of Boerhaavia diffusa L. (Nyctaginaceae) and Curculigo orchioides Gaertn. (Hypoxidaceae) were phytochemically characterised by HPLC-DAD and profiled for their antioxidant, antigenotoxic and cytotoxic activities. B. diffusa DEC was rich in ferulic acid and vanillin, while the HE also contained boeravinone B and Eupalitin. Both C. orchioides HE and DEC displayed the main occurrence of orcinol-beta-d-glucoside and curculigoside A. Antioxidant activity was assayed through spectrophotometric DPPH, ABTS and beta-carotene bleaching test, and using (HP)TLC bioautographic strategies. For both crude drugs, HE was the best performing preparation. Properly modified SOS-Chromotest evidenced a 10% inhibition by phytocomplexes against 4-nitroquinoline-N-oxide, and a higher bioactivity for vanillin (36.60 +/- 1.68%) and ferulic acid (35.09 +/- 1.53%). C. orchioides HE was the preparation which showed higher cytotoxicity against drug-sensitive human T-lymphoblastoid cell line (CCRF-CEM) and multidrug-resistant leukaemia cell line (CEM/ADR5000), and Eupalitin was the only pure compound to exhibit an IC50 value.

ISOLATION OF FIVE BIOACTIVE COMPONENTS FROM EUPATORIUM ADENOPHORUM SPRENG USING STEPWISE ELUTION BY HIGH-SPEED COUNTER-CURRENT CHROMATOGRAPHY.[Pubmed:22328809]

J Liq Chromatogr Relat Technol. 2011 Dec 1;34(20):2505-2515.

Semi-preparative high-speed counter-current chromatography (HSCCC) was successfully performed for isolation and purification of caffeic acid 4 bioactive flavonoids from Eupatorium adenophorum Spreng using stepwise elution with a pair of two-phase solvent systems composed of ethyl acetate-methanol-water at the volume ratios of 10: 1: 10 and 5: 1: 5 (v/v). From 378.5 mg of crude extract 24.1 mg of caffeic acid, 6.7 mg of 4'-methyl quercetagetin 7-O-(6"-O-E-caffeoylglucopyranoside), 6.5 mg of quercetagetin 7-O-(6"-O-acetyl-beta-D-glucopyranoside), 31.8 mg of Eupalitin 3-O-beta-D-galactopyranoside and 36.7 mg of Eupalitin were obtained with the purities of 96.0%, 91.2%, 82.3%, 95.1% and 85.6%, respectively. The structures of the separated compounds were identified by EI-MS, (1)HNMR and (13)CNMR.

Two new rotenoids from Boerhavia repens.[Pubmed:22224280]

Nat Prod Commun. 2011 Nov;6(11):1651-2.

Two new rotenoids, boerharotenoids A (1) and B (2), and four known compounds, boeravinone (3), 5,7,3'-trihydroxycoumaronochromone (4), boeravinone F (5), and Eupalitin-3-O-beta-D-galactopyranoside (6), have been isolated from Boerhavia repens and their structures established by spectroscopic (1D and 2D NMR) and mass spectrometric comparison with literature values.

Flavonoids and phenol glycosides from Boerhavia diffusa.[Pubmed:17365699]

Nat Prod Res. 2007 Feb;21(2):126-34.

Four new compounds were isolated from Boerhavia diffusa namely Eupalitin 3-O-beta-D-galactopyranosyl-(1''' --> 2'')-O-beta-D-galactopyranoside (1), 3,3',5-trihydroxy-7-methoxyflavone (4), 4',7-dihydroxy-3'-methylflavone (5) and 3,4-dimethoxyphenyl-1-O-beta-D-apiofuranosyl-(1'' --> 3')-O-beta-D-glucopyranoside (7) along with eight known compounds. The structures were elucidated by analysis of their spectroscopic data.

Characterisation of the phenolic profile of Boerhaavia diffusa L. by HPLC-PAD-MS/MS as a tool for quality control.[Pubmed:16315490]

Phytochem Anal. 2005 Nov-Dec;16(6):451-8.

Phenolic acids and flavonols of nine leaf and three root samples of Boerhaavia diffusa L., collected at different locations and subjected to several drying procedures, were characterised by reversed-phase HPLC-PAD-ESI/MS for the first time. Ten phenolic compounds were identified: 3,4-dihydroxy-5-methoxycinnamoyl-rhamnoside, quercetin 3-O-rhamnosyl(1-->6)galactoside (quercetin 3-O-robinobioside), quercetin 3-O-(2"-rhamnosyl)-robinobioside, kaempferol 3-O-(2"-rhamnosyl)-robinobioside, 3,5,4'-trihydroxy-6,7-dimethoxyflavone 3-O-galactosyl(1-->2)glucoside [Eupalitin 3-O-galactosyl(1-->2)glucoside], caffeoyltartaric acid, kaempferol 3-O-robinobioside, Eupalitin 3-O-galactoside, quercetin and kaempferol. Quantification was achieved by HPLC-PAD and two phenolic patterns were found for the leaves, in which quercetin 3-O-robinobioside or quercetin 3-O-(2"-rhamnosyl)-robinobioside was the major compound. Caffeoyltartaric acid was only present in the root material where it represented the main phenolic constituent. The results obtained demonstrated that the geographical origin (particularly the nature of the soil), but not the drying process, influences the phenolic composition.

Immunosuppressive properties of flavonoids isolated from Boerhaavia diffusa Linn.[Pubmed:15683850]

Int Immunopharmacol. 2005 Mar;5(3):541-53.

Plant extracts have been widely evaluated for possible immunomodulatory properties. We have earlier reported that ethanolic extract of Boerhaavia diffusa root, a plant used in Indian traditional medicine, has significant immunomodulatory potential. B. diffusa hexane, chloroform and ethanol extracts, and two pure compounds Bd-I (Eupalitin-3-O-beta-D-galactopyranoside) and Bd-II (Eupalitin) were evaluated in vitro for their effect on T cell mitogen (phytohemagglutinin; PHA) stimulated proliferation of human peripheral blood mononuclear cell (PBMC), mixed lymphocyte culture, lipopolysaccharide (LPS) stimulated nitric oxide production by RAW 264.7, PHA and LPS induced IL-2 and TNF-alpha production, in human PBMCs, superoxide production in neutrophils, human natural killer (NK) cell cytotoxicity and nuclear translocation of nuclear factor-(kappa)B and AP-1 in PHA stimulated PBMCs. The chloroform and ethanol extracts inhibited PHA stimulated proliferation of peripheral blood mononuclear cells, two-way MLR, NK cell cytotoxicity as well as LPS induced NO production by RAW 264.7; the hexane extract showed no activity. Bd-I purified from the ethanolic extract at equivalent dose, inhibited PHA-stimulated proliferation of peripheral blood mononuclear cells, two-way MLR and NK cell cytotoxicity as well as LPS induced NO production by RAW 264.7 equally or more effectively than the parent ethanolic extract. Bd-I inhibited production of PHA stimulated IL-2 at the protein and mRNA transcript levels and LPS stimulated TNF-alpha production in human PBMCs; it also blocked the activation of DNA binding of nuclear factor-(kappa)B and AP-1, two major transcription factors centrally involved in expression of the IL-2 and IL-2R gene, which are necessary for T cell activation and proliferation. Our results report selective immunosuppressive activity of B. diffusa leaf extracts and that this activity lies in Eupalitin-3-O-beta-D-galactopyranoside (Bd-I) isolated and purified from the ethnaolic extract. Thus, Bd-I could be a candidate for development as an immunosuppressive agent.

Terpenoids and flavonoids from Artemisia species.[Pubmed:10865468]

Planta Med. 2000 May;66(4):391-3.

A phytochemical reinvestigation of the aerial parts of Artemisia sieversiana gave a new guaianolide and two known flavones (chrysosplenetin and 5-hydroxy-3',4',6,7-tetramethoxyflavone). Antifungal fractions derived from the chloroform extract of A. annua afforded two cadinane derivatives (arteannuin B and artemisinin), oleanolic acid, beta-sitosterol, stigmasterol, and the four flavones artemetin, bonanzin, Eupalitin and chrysosplenetin. Their structures were elucidated by spectral methods. All isolates from the two species were tested in vitro for antifungal activity. Arteannuin B, a main sesquiterpenoid in A. annua, showed antifungal activity against one human (Candida albicans, MIC: 100 micrograms/ml) and four plant pathogenic fungi (Gaeumannomyces graminis var. tritici, Rhizoctonia cerealis, Gerlachia nivalis and Verticillium dahliae, MICs: 150, 100, 150 and 100 micrograms/ml, respectively) whereas others showed no antifungal activity. The MIC value of ketoconazole to C. albicans was 1.0 microgram/ml, and those of triadimefon to G. graminis var. tritici and R. cerealis 150 and 100 micrograms/ml.

Effects on cultured neonatal mouse calvaria of the flavonoids isolated from Boerhaavia repens.[Pubmed:8946741]

J Nat Prod. 1996 Nov;59(11):1015-8.

A MeOH extract from the whole plant of Boerhaavia repens was found to inhibit bone resorption induced by parathyroid hormone (PTH) in tissue culture. Systematic separation of the MeOH extract afforded one new and two known flavonoid glycosides, namely, Eupalitin 3-O-beta-D-galactopyranosyl-(1-->2)-beta-D-glucopyranoside (1), Eupalitin 3-O-beta-D-galactopyranoside (2), and 6-methoxykaempferol 3-O-beta-D-(1-->6)-robinoside (3). The structure of the new compound 1 was determined using spectroscopic techniques. The inhibitory activity of these substances toward bone resorption induced by PTH was evaluated, and compounds 1 and 2 were found to exhibit significant activity.