Column chromatography for preparing rosmarinic acid rich extract from Orthosiphon aristatus
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Abstract:
Chromatographic techniques were used to prepare rosmarinic acid rich extract from Orthosiphon aristatus. Such extract is highly required for herbal product development because of its remarkable bioactivities. Therefore, the plant crude extract was fractionated using solvent mixture, ethyl acetate and ethanol in column chromatography. The solvent system was developed using thin layer chromatography. The results found that 60-99.9% ethyl acetate in ethanol could separate rosmarinic acid with the retention factor (Rf) ranged from 0.2–0.3. Of the solvent systems, 70% ethyl acetate could produce the highest yield of rosmarinic acid, 4.5% w/w with 100% purity. The concentration of rosmarinic acid was quantified by high performance liquid chromatography integrated with tandem mass spectrometry. The subsequent combined fractions could recover 70% of total rosmarinic acid from crude extract. The bed height of the silica gel packed column increased from 16 to 24 and 32 cm did not affect the performance of rosmarinic acid elution in column chromatography. The silica gel absorbent could be repeatedly used up to five times to recover rosmarinic acid from crude extract. Column chromatography can be used to recover rosmarinic acid (>85%) using the binary solvent system (70% ethyl acetate:30% ethanol) effectively.Keywords:
Rosmarinic acid
Rosmarinic acid is a valuable polyphenolic molecule mainly found in species of Boraginaceae and Lamiaceae. The amount of rosmarinic acid varies according to the environmental condition in which the plant grows, temperature, and humidity. The content of 0.01 to 72 mg/g of rosmarinic acid has been determined in various plants. Biotechnological production of rosmarinic acid by plant cell culture is recommended for its high production. The investigations have mainly addressed sources of rosmarinic acid, its production, and its biological effects. It has antioxidant, anti-inflammatory, antiviral, and anticancer activities, and it is an important substance for the pharmaceutical, food, and cosmetic industries. In addition to its antioxidant effects, it has been tested in recent studies in neurodegenerative diseases and has been found to have beneficial effects in these diseases, especially on memory. In this chapter, attention was drawn to the importance of rosmarinic acid, a valuable chemical, and general information about its phytochemistry, production, and biological activities was reviewed.
Rosmarinic acid
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Activity coefficients(r~∞)of ethyl acetate-ethanol-water were measured at glycerol by gas-chromatography.Model references were correlated with Wilson equation by single method.VLE data of ethyl acetate-ethanol and tehyl acetate-water were measured.VLE data of ethyl acetate-ethanol-glycerol and ethyl acetate-water-glycerol were calculated by model references of two systems.Results of measurement and calculation was provided for extraction simulation calculation of ethyl acetate-ethanol-water and ethyl acetate-ethanol.
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Agrobacteria mediated Coleus blumei tumour tissues were cultured in vitro on MS medium. Sixteen diversified transformed callus cultures were maintained for several years in the absence of plant growth regulators and antibiotics without affecting the growth rate. Rosmarinic acid was detected spectrophotometrically in all tissue lines but in different quantities. The highest rosmarinic acid accumulation detected was 11% of dry tissue mass. The relation between culture growth and rosmarinic acid production was investigated in three callus lines. The lines showed different rosmarinic acid accumulation in relation to their growth rate; it was either parallel or inversely related to the tissue growth. The effects of certain medium constituents on the callus growth and rosmarinic acid accumulation were examined in four tumour cell lines. Addition of 4% or 5% sucrose stimulated rosmarinic acid synthesis and decreased callus growth. Nitrogen reduction to one half or one quarter of initial concentration did not affect rosmarinic acid synthesis and decreased callus growth in three lines, while it increased rosmarinic acid accumulation and callus growth in one line. Addition of 0.1 mg/l Phe stimulated rosmarinic acid production in two lines but had little effect on the rosmarinic acid level in others. Rosmarinic acid production was significantly improved on modified macronutrients, where the Ac2 line produced 16.5 mg of rosmarinic acid per tube (0.2 g of dry wt) after being in culture for 35 days.
Rosmarinic acid
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Callus
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The present study compares the gastrointestinal stability of rosmarinic acid in aqueous extracts of thyme, winter savory and lemon balm with the stability of pure rosmarinic acid. The stability of rosmarinic acid was detected after two-phase in vitro digestion process (gastric and duodenal) with human gastrointestinal enzymes. The concentration of rosmarinic acid in undigested and digested samples was detected using HPLC-DAD. Results showed that gastrointestinal stability of pure rosmarinic acid was significantly higher than that of rosmarinic acid from plant extracts after both gastric and intestinal phases of digestion. Among plant extracts, rosmarinic acid was the most stable in lemon balm after gastric (14.10%) and intestinal digestion phases (6.5%). The temperature (37 °C) and slightly alkaline medium (pH=7.5) did not affect the stability of rosmarinic acid, while acid medium (pH=2.5) significantly decreased its stability (≥50%). In addition, the stability rate of rosmarinic acid is influenced by the concentration of human gastrointestinal juices.
Rosmarinic acid
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Summary This study was conducted to obtain annatto extracts with both high antioxidant capacity and colour potential using solvents of different polarities (water, ethanol/water, ethanol, ethanol/ethyl acetate and ethyl acetate). The highest levels of total phenolic compounds were found in the water, ethanol/water and ethanol extracts (0.5 mg GAE mL −1 ), and the highest level of bixin was found in the ethanol/ethyl acetate extract (5.2 mg mL −1 ), which was characterised as the reddest and the most vivid one ( a* = 40.5, h° = 46.1, C* = 58.4). The ethanol/ethyl acetate extract also showed the highest antioxidant activity (4.7 μ m TEAC mL −1 ) and the highest percentage of tryptophan protection against singlet oxygen (63.6%). On the other hand, ethyl acetate and ethanol/water were the least effective solvents for the extraction of phenolic compounds and bixin, respectively. According to the multivariate statistical analysis, ethanol/ethyl acetate and ethyl acetate were the most promising solvents to obtain annatto extracts with both antioxidant and colour properties.
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Four spearmint, and two peppermint clonal lines, selected for enhanced rosmarinic acid content (50-120 mg g -1 rosmarinic acid DW), where up to 80% of the antioxidant activity was correlated to rosmarinic acid content, were examined to determine the effects of environmental and physiological conditions on the accumulation of rosmarinic acid in leaf tissues. Exposure to a short photoperiod of 12 hours in comparison to 16 hours reduced rosmarinic acid accumulation in two mint lines, but no significant difference was found between photoperiods of 14 and 16 hours. The physiological age of the plant strongly influenced the accumulation of rosmarinic acid with the highest levels recorded in the vegetative state, and a significant reduction in the concentration of rosmarinic acid in the leaves in both the bud initiation and flowering stages in the mint lines. Cold stress, impacted over a six week period had no effect on rosmarinic acid production. A field study of the commercial chemotype 700B indicated that soil type plays an essential role in the accumulation of rosmarinic acid in the leaf tissue, probably due to retention of moisture which favours rosmarinic acid production. For producers and extractors, taking these factors into account would significantly increase rosmarinic acid accumulation in commercially high rosmarinic acid mint and increase the quality control of plant extracts for the natural products industry.
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Mentha spicata
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A series of mixed solvents were analyzed by eluent HPLC, which is a new high performance liquid chromatography (e HPLC) method . The characteristics and advantage of this eluent HPLC method were demonstrated by comparing the conventional HPLC result with eluent HPLC result of a typical reversed phased HPLC solvent sample .The result was that the tiny difference between two samples was obvious.
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Designing Liquid-Liquid Equilibrium pot.VLE data of Ethyl acetate-Ethanol-Glycerol et al.and Ethyl acetate-Ethanol-Wa-ter-Glycerol were Measured.The third Model parameters were Correlated by combining binary parameters of Wilson equation with VLEdata of ternary system.Thus,VLE data of Ethyl acetate-Ethanol-Water-Glycerol was calculated,Results of Measurement and Calcula-tion were Compared,which were Provide fundament data for Extraction Simulation Calculation of Ethyl acetate-Ethanol-water and Ethylacetate-Ethanol.
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Rosemary plants were analysed using HPLC and eight different compounds (vanillic acid, caffeic acid, rosmarinic acid, naringin, hispidulin, cirsimaritin, carnosol and carnosic acid) were identified and quantified. The analysis of the DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging activity revealed that rosmarinic and carnosic acids were the best rosemary scavengers with IC sun(50) values of 27 and 32 micro M, respectively. Environmental influences on rosmarinic and carnosic acids content in rosemary plants were studied over a period of one year under southern UK conditions. Carnosic acid reached the maximum concentrations in December, decreasing by 50% during the summer months, while rosmarinic acid showed a constant concentration during the year. The significance of these results has been discussed later in this paper.
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Carnosic acid
Rosmarinus
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The conversion of ethanol to ethyl acetate has an advantage as a method of ethanol recovery since ethyl acetate is amenable to simple solvent extraction. The potential of Candida utilis in this conversion was studied. The kinetics of accumulation of ethanol and ethyl acetate in glucose-grown C. utilis showed that ester formation resulted from ethanol utilization under appropriate aeration and was inhibited by Fe(3+) supplementation. Candida utilis converted ethanol to ethyl acetate optimally at pH 5.0-7.0. The five-hour rate of ester production increased as the ethanol concentration increased to 10 g/L, and rapidly declined to zero at concentrations exceeding 35 g/L. Thus, C. utilis has potential to recover dilute ethanol in the form of ethyl acetate.
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