Seeds Of Oroxylum Indicum Research Articles

Column-free matrix solid-phase dispersion extraction based on cucurbit[8]uril used for the determination of the flavonoid content in Oroxylum indicum (L.) Vent.

A simple, rapid and environmental method named column-free matrix solid-phase dispersion (FMSPD) has been investigated for the extraction of three flavonoids (oroxin A, oroxin B and baicalein) from the seeds of Oroxylum indicum (L.) Vent. In this study, cucurbit[8]uril was used as the sorbent of FMSPD to selectively extract three flavonoid compounds and transferred them into an aqueous solution for direct determination using HPLC-UV based on the recognition interaction of cucurbit[8]uril toward the compounds. The variables that influenced the extraction efficiency were investigated, which include the amount of cucurbit[8]uril, grinding time, volume of water, and pH of the solution. A good linearity was exhibited with correlation coefficients > 0.9991 for all three flavonoids. The intra- and inter-day precisions were 1.7–2.6% and 3.1–5.5%, respectively, and the limit of detection was between 0.1 and 0.18 μg mL–1. The recoveries ranged from 90.8% to 101.4%, with relative standard deviations of 2.9–6.8% under the optimized conditions. The developed method was applied to analyze four kinds of Semen Oroxyli from different regions of China. F- and t-tests showed that the results had no significant difference when comparing the traditional ultrasound-assisted extraction method to the novel FMSPD extraction method, but the method was simpler, faster and did not use organic solvents.

Concise synthesis and antidiabetic activity of natural flavonoid glycosides, oroxins C and D, isolated from the seeds of Oroxylum indium

The first concise synthesis of natural flavonoid glycosides, oroxins C (1) and D (2), which were isolated from the seeds of Oroxylum indicum, was efficiently achieved by a convergent strategy. The synthesized natural products 1 and 2 were evaluated for their inhibitory activities against α-glucosidase, α-amylase, and lipase. Compound 1 showed strong α-amylase and lipase inhibition, with IC50 values of 210 and 190 μM, respectively, but exhibited no inhibitory activity against α-glucosidase. Compound 2 showed strong inhibition against α-glucosidase and lipase, with the respective IC50 values of 180 and 80 μM.

Ultra-rapid, enhanced and eco-friendly extraction of four main flavonoids from the seeds of Oroxylum indicum by deep eutectic solvents combined with tissue-smashing extraction

Rapid, green and efficient extraction of active compounds followed by fast analysis is always pursued in the field of food analysis and/or industry. Herein, a green and highly efficient extraction of four active flavonoids from the seeds of Oroxylum indicum using a combination of natural deep eutectic solvents (DESs) and tissue-smashing extraction (TSE) technique was applied and a UPLC method was developed for their sensitive and selective quantification. RSM coupled with BBD procedure was used to optimize the extraction conditions based on single factors, such as liquid-solid ratios, extraction speed and extraction time. Compared with other conventional methods, the TSE greatly shortens extraction time, obviously raises the extraction production, and decreases energy consumption. By combination of the DES-based TSE and UPLC, the analysis of flavonoids was accomplished within only 6 min, providing an ultra-rapid, environmentally friendly and promising choice for extraction and analysis of active compounds in natural products.

Flavonoids from the seeds of Oroxylum indicum and their anti-inflammatory and cytotoxic activities

Two new flavonoid glycosides, named oroxin C (1) and oroxin D (scutellarein 4'-methyl ether 7-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside, 2), together with eight known flavonoids (3–10), were isolated from the seeds of Oroxylum indicum. Their structures were elucidated unambiguously by spectroscopic techniques and chemical methods. Anti-inflammatory and cytotoxic activities of all the isolated compounds were evaluated. Chrysin (3) and chrysin-6-C-β-D-glucopyranosyl-8-C-α-L-arabinopyranoside (10) showed moderate inhibitory effects aganist the LPS-induced NO production in murine RAW264.7 macrophages with IC50 values of 18.63 ± 0.91 and 28.69 ± 0.43 μM, respectively. Chrysin (3) exhibited weak cytotoxic activity aganist A549, HepG2 and SW480 human cancer cell lines with IC50 values of 40.88 ± 3.85, 50.55 ± 2.59 and 91.60 ± 4.27 μM, respectively.

Phytochemical Investigation and Antidiabetic Activity of Oroxylum Indicum Vent. Seed

The present investigation has been carried out on seeds of Oroxylum indicum (L) Vent. used in various ayurvedic preparations. The study deals with physicochemical parameters, phytochemical analysis by HPTLC and their use in the treatment of diabetes because the seeds are used traditionally in the treatment of diabetes. The densitometric analysis revealed the presence of 15 spots of different phytoconstituents at different Rf . The maximum percentage of area of component in the extract was found to be 71.58 % w/w at Rf 0.88. The seeds of Oroxyllum indicum shows significant effect (p<0.001) by lowering the blood glucose level in chemically induced diabetic experimental animals. The determination of Ash value, Extractive value and HPTLC fingerprint profile will aid future investigators in their other pharmacological analyses of this species.

Total Flavonoids from Oroxylum indicum Induce Apoptosis via PI3K/Akt/PTEN Signaling Pathway in Liver Cancer.

Total flavonoids (TF), derived from the seeds of Oroxylum indicum (L.) Vent., possess many pharmacological functions. In the present study, H22-bearing mice and SMMC-7721 models were employed to evaluate the antitumor activity of TF and to and investigate its possible mechanisms both in vitro and in vivo. Cell viability was evaluated by MTT assay; cell apoptosis rate was analyzed via Annexin V-FITC/PI double staining by flow cytometer. Meanwhile, the expressions of apoptosis-related mRNA and proteins were evaluated by RT-PCR and Western blot analysis. The results revealed that TF could significantly inhibit the tumor growth, and the possible mechanism was related to the effect of inducing tumor cells apoptosis through PI3K/Akt/PTEN signaling pathway. This study has provided a theoretical basis for the further development and application of TF as antitumor drugs.

Kinetics and modeling for extraction of chrysin from Oroxylum indicum seeds

Research on extraction of chrysin is crucial for theoretical purposes and for food industrial bioprocesses. Optimization and kinetics of chrysin extraction from seeds of Oroxylum indicum (L.) Vent. were analyzed using agitated solid-liquid extractions with ethanol and water mixtures. The influence of extraction process parameters was investigated. Optimized conditions for chrysin extraction were a 0.2 mole fraction of ethanol as an extraction solvent, a temperature of 318 K, an agitation speed 1,400 rpm, and a solid to solvent ratio of 1:30. The extraction kinetic behavior of chrysin followed first order kinetics. The kinetic expression developed by Spiro and Siddique was used and the model was in agreement with experimental results. The diffusion coefficient ranged from 1.38×10−11 to 19.43×10−11 m2·s−1 and the activation energy for extraction kinetics was 21.85 kJ·mol−1.

Stilbenoids from the seeds of Oroxylum indicum

Phytochemical investigation on the seeds of Oroxylum indicum (L.) Vent. led to the isolation of two new stilbenoid compounds (E)-dihydropinosylvin-2-carboxyl-5-O-β-d-glucopyranoside (1) and (E)-dihydropinosylvin-3-O-β-d-glucopyranoside (2), along with the three known compounds, (E)-pinosylvin-3-O-β-d-glucopyranoside (3), dihydropinosylvin (4) and pinosylvin (5). Their structures were elucidated by spectroscopic techniques. The stilbenoids identified in the seeds of O. indicum may possess chemotaxonomic significance at the generic level.

Role of Seed Mycoflora on Seed Germination of Oroxylum indicum (L.) Vent. in Kumaun region of Indian Central Himalaya

A number of fungus was isolated from the seeds of Oroxylum indicum (L.) Vent. The mycoflora associated with the seeds of this tree have not been previously reported from Kumaun region of Indian Central Himalaya. During the course of study mycoflora such as Fusarium solani, Aspergillus niger, Aspergillus nidulens, Penicillium sp., Trichoderma harzianum, Alternaria solani, Alternaria alternata, Curvolaria lunata., Stachybotryis chartarum, Acremonium sp., Rhizoctonia solani, Chaetomium globosum, Cladosporium cladoporoides and Torula allii were isolated from the seeds.

Chemical constitunents of seeds of Oroxylum indicum

To study the chemical constituents in the seeds of Oroxylum indicum. Twenty compounds were isolated and purified by silica gel, and Sephadex LH-20 column chromatography, and their structures were determined by spectroscopic analysis including NMR and MS. Twenty compounds were isolated and identified as oroxin A (1), oroxin B (2), chrysin (3), baicalein (4), quercetin (5), apigenin (6), kaempferol (7), quercetin-3-O-ara-binopyranoside (8), lupeol C9), lup-20 (29)-ene-2alpha,3beta-diol (10), pinosylvin (11), dihydropinosylvin (12), cholest-5-ene-3, 7-diol (13), rengyol (14), isorengyol (15), zarzissine (16), (E) -pinosylvin-3-O-beta-D-glucopyranoside (17), adenosine (18), sitosterol (19) and daucosterol (20). Compounds 11-13 and 15-18 were obtained from the genus Oroxylum for the first time, and except compound 18, the remaining 6 compounds were obtained from the family Bignoniaceae for the first time.

Quantitative Determination of Seven Flavonoids in Bark and Seeds of Oroxylum indicum by HPLC-UV, UPLC-UV Methods and Confirmation by Mass Spectrometry

Oroxylum indicum Vent., family Bignoniaceae is a rich source of flavonoid compounds [1]. The seeds and bark are used medicinally for alleviating pain and as an antiphlogistic medicine. Chrysin, baicalein and the other flavonoids in Oroxylum have anti-inflammatory and anti-allergy effects [1,2]. A simple and specific analytical method for the quantitative determination of flavonoids in bark and seeds of the Oroxylum indicum was developed using HPLC-UV and UPLC-UV. By LC-UV, the separation was achieved by reversed-phase chromatography on a C18 column with water and acetonitrile (both containing 0.1% acetic acid) as the mobile phase. In UPLC-UV system, acetic acid was replaced by formic acid. Detection was performed at 280 nm. The methods were validated for linearity, repeatability, limits of detection (LOD) and limits of quantification (LOQ). The limits of detection and limits of quantification by HPLC-UV was found to be 0.2 µg/mL and 1 µg/mL for baicalein (1), OA-6 (2), OA-7 (3), chrysin (4), oroxylin A (5), 5,7 dihydroxy-6-methoxy-2-phenylchroman-4-one (DHMF, 6) and acetyl chrysin (7), respectively and 0.02 µg/mL and 0.1 µg/mL by UPLC-UV method. An LC-MS coupled with electrospray ionization (ESI) interface method is described for the identification and quantification of flavonoids in various plant samples. This method involved the use of the [M+H]+ ions of flavonoids in the positive ion mode with extractive ion monitoring (EIM). The developed methods were applied for the determination of seven flavonoids in bark and seeds of Oroxylum indicum. All seven flavonoids were detected in bark and only chrysin was found in the seeds of Oroxylum indicum. Acknowledgements: This research is funded in part by “Science Based Authentication of Dietary Supplements“ Funded by the Food and Drug Administration grant number 2 U01 FD 002071-07 and the United States Department of Agriculture, Agricultural Research Service Specific Cooperative Agreement Number 58-6408-06-067. Also this research is supported jointly by CSIR and M/S Zandu pharmaceuticals and NCNPR. The CSIR budget code for this project is ”Fellowship abroad p-80104”.

HSCCC‐MS Study of Flavonoids in the Extracts from the Seeds of Oroxylum indicum

In this study, two analytical high‐speed countercurrent chromatography (HSCCC) instruments, interfaced directly with electrospray ionization and atmospheric pressure chemical ionization mass spectrometry, were explored for the separation of a mixture of three standard flavonoids. Hexane–ethyl acetate–methanol–water solvent systems with different ratios were chosen and optimized for the best separation. On‐line HSCCC‐MS was successfully used in the identification of flavonoids from an ethyl acetate extract of the seeds of Oroxylum indicum.

Analysis of Flavonoids in the Extracts from the Seeds of Oroxylum indicum Using High Speed Countercurrent Chromatography/Mass Spectrometry

The HSCCC was successfully interfaced with a mass spectrometer possessing APCI‐ and ESI‐MS mode for the first time. The coupling system gave an excellent separation of ethyl acetate extract from the seeds of O. indicum using a solvent system composed of hexane‐ethyl acetate‐methanol‐0.2% formic acid (1:1.2:1:1); the online data of APCI‐MS and APCI‐MS‐MS provided useful information for the identification of the compounds.

Comparison of high-speed counter-current chromatography instruments for the separation of the extracts of the seeds of Oroxylum indicum

Analytical Milli high-speed counter-current chromatography (HSCCC) was used for the selection and optimization of the two-phase solvent system to separate flavonoids from the extracts of the seeds of Oroxylum indicum. The optimum solvent system obtained from Milli-CCC was also the best solvent system for preparative HSCCC and led to the successful separation of two crude flavonoids from the seeds of O. indicum by Lab/Prep (laboratory preparative) HSCCC using different sized coils. Four flavonoids were isolated by preparative HSCCC: baicalein-7-O-diglucoside (25.0 mg, 92% purity), baicalein-7-o-glucoside (50.4 mg; 95% purity), baicalein (75 mg; purity 98%) and chrysin (100 mg; purity 98%).

Separation and Identification of Flavonoids in an Extract from the Seeds of Oroxylum indicum by CCC

Oroxylum indicum (O. indicum) is widely used as a medicinal plant in China and Japan. The seeds are used as the crude drug “Mu Hu DIE” in China. Flavonoids are present in the seeds of O. indicum. The composition of an ethyl acetate extract of the seeds of O. indicum is completed using high speed analytical counter current chromatography and preparative high‐speed countercurrent chromatography (HSCCC). The HSCCC separation of the extract used a solvent system of hexane/ethyl acetate/methanol/water. Optimal distribution coefficients (K D ) were determined by use of high performance liquid chromatography (HPLC). An HPLC method was developed to analyse the extract. Using an isocratic elution, effective CCC separation of three components was achieved. A step‐gradient elution was then developed that produced a faster separation with better resolution. Separation of the components was achieved using 20 mg of extract, and the peaks were examined by LC–MS and NMR. The flavonoids, chrysin, and baicalein, were identified. Another flavonoid, possibly baicalein‐7‐o‐glucoside was suspected.

Isolation and identification of four flavonoid constituents from the seeds of Oroxylum indicum by high-speed counter-current chromatography

Four flavonoids, chrysin, baicalein, baicalein-7- O-glucoside, baicalein-7- O-diglucoside (Oroxylin B) and one unknown flavonoid have been isolated and purified for the first time in the seeds of Oroxylum indicum by high-speed counter-current chromatography with a two-phase solvent system composed of chloroform–methanol–water (8:10:5, v/v). Then, 50 mg baicalein-7- O-glucoside, 10.5 mg baicalein-7- O-diglucoside, 4.5 mg chrysin-7- O-diglucoside, 25 mg baicalein and 45 mg chrysin could be obtained after injecting 20 mg/ml sample extract ten times and their purities were 96, 90, 85, 95 and 98%, respectively. All these constituents were identified by high-performance liquid chromatography–mass spectrometry and nuclear magnetic resonance.

Oroxindin—A new flavone glucuronide fromOroxylum indicum Vent

From the ethanol extract of the seeds ofOroxylum indicum a new flavone glucuronide named oroxindin has been isolated. Based on chemical as well as UV, IR, PMR and mass spectral data oroxindin has been constituted as 5-hydroxy-8-methoxy-7-0-β-D-glucopyranuronosyl flavone (wogonin-7-0-β-D-glucuronide).

Chemical investigation of the seed-oil ofOroxylum indicum Vent.

The chemical investigation of the seeds ofOroxylum indicum Vent. has resulted in the isolation of a yellow crystalline substance (m.p. 274°) and a fatty oil.