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Study Of Kinetics Of The D-Pinitol Extraction From Carob Pods Using Supercritical Co2
... [2,7,8] The main polyphenolic constituents isolated from carob pods are reported to be insoluble, highly polymerised condensed tannins containing a flavan nucleus. [9] Other research has analysed the cyclitol content of the pods by high-performance liquid chromatography (HPLC), [10][11][12] seed germ amino acid content via HPLC, and the presence of fatty acids employing gas chromatography (GC). [13] Recently, analysis of carob flesh and pods was conducted using FTIR spectroscopy and this technique was used to assess the origin and type of carob material. ...
... Compounds 10-12 have previously been identified in various parts of C. siliqua. This includes the isolation, [27] as well as identification of D-pinitol (pods), [4,10,12] myricitrin (leaves), [20] and sucrose (pods). [12,28] The 1 H, 13 C, and heteronuclear single quantum correlation (HSQC) NMR spectroscopic data associated with siliquapyranone 9 were consistent with the high-resolution electrospray ionisation mass spectrometry (HR-ESI-MS) data (m/z 595.1301; calcd for [ , and a methyl resonance at d H 1.28 (d, J 6.3, 3H, C-6), which were consistent with the presence of a 3-hydroxy-5-hexanolide structure. ...
Studies of the phytochemistry of carob (Ceratonia siliqua) leaf material are extremely limited. This report features the second natural product isolation study of carob leaves and the first such investigation of C. siliqua grown in Australia. Investigation of leaf material from seven carob cultivars using pressurised hot water extraction (PHWE) revealed the presence of high levels of myricitrin, d-pinitol, and sucrose in addition to the previously unreported natural product siliquapyranone {(2R,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-2-(((2S,4S)-2-methyl-6-oxotetrahydro-2H-pyran-4-yl)oxy)tetrahydro-2H-pyran-3,4-diyl bis(3,4,5-trihydroxybenzoate)}. Siliquapyranone represents a biosynthetic fusion of conventional 2,3-gallate esters on a β-glucose tannin with a hydroxytetrahydro-2H-pyran-2-one-related non-tannin tetrahydropyran-2-one, parasorboside. Preliminary biological testing indicates that siliquapyranone exhibits weak activity against both tumour and normal cell lines. This suggests that, like most tannins and parasorboside, siliquapyranone may act as an antifeedant.
... The supercritical state is achieved when the temperature and pressure of a fluid are raised above the critical point, exhibiting unique properties in terms of compressibility, density, and viscosity that differ from those of gases or liquids in normal state. Cháfer and Berna [59] applied SFE for isolation of d-pinitol from carob pods at pressure of 20 or 30 MPa, temperature of 40 or 60 °C, and CO 2 flow rate from 0.5 to 2.5 mL min −1 , using water to trap the extract. The maximum extraction yield of flavonoids of approximately 4.24 mg g −1 from Maydis stigma flowers using SFE was obtained using temperature of 50.88 °C, pressure of 41.80 MPa, cosolvent amount of 2.488 mL g −1 , and extraction time of 120 min [59]. ...
... Cháfer and Berna [59] applied SFE for isolation of d-pinitol from carob pods at pressure of 20 or 30 MPa, temperature of 40 or 60 °C, and CO 2 flow rate from 0.5 to 2.5 mL min −1 , using water to trap the extract. The maximum extraction yield of flavonoids of approximately 4.24 mg g −1 from Maydis stigma flowers using SFE was obtained using temperature of 50.88 °C, pressure of 41.80 MPa, cosolvent amount of 2.488 mL g −1 , and extraction time of 120 min [59]. ...
Development of efficient methods for isolation and separation of biologically active compounds remains an important challenge for researchers. Designing systems such as organomineral composite materials that allow extraction of a wide range of biologically active compounds, acting as broad-utility solid-phase extraction agents, remains an important and necessary task. Selective sorbents can be easily used for highly selective and reliable extraction of specific components present in complex matrices. Herein, state-of-the-art approaches for selective isolation, preconcentration, and separation of biologically active compounds from a range of matrices are discussed. Primary focus is given to novel extraction methods for some biologically active compounds including cyclic polyols, flavonoids, and oligosaccharides from plants. In addition, application of silica-, carbon-, and polymer-based solid-phase extraction adsorbents and membrane extraction for selective separation of these compounds is discussed. Potential separation process interactions are recommended; their understanding is of utmost importance for the creation of optimal conditions to extract biologically active compounds including those with estrogenic properties.
... It was first isolated in the sugar pine (Pinus Lambertiana) (Anderson et al., 1952). D-pinitol is a naturally occurring compound present in peanut (Lee and Morris, 1963), Bougainvillea spectabilis (Jawla et al., 2013;Narayanan et al., 1987;Vidhate et al., 2015), and Argyrolobium roseum (Ram et al., 2007;Sharma et al., 2016), but for manufacturing purposes it is generally extracted from soybean (Kawai and Kumazawa, 1982;Phillips et al., 1982;Streeter et al., 2001) and also from carob (Baumgartner et al., 1986;Cháfer and Berna, 2014;Tetik and Yüksel, 2014). ...
... For extraction of polar substances, a modifier polar co-solvent such as methanol, ethanol, acetonitrile, acetone, water, ethyl ether or dichloromethane can be added to increase the solubility (Wang and Weller, 2006). Cháfer and Berna (2014) successfully applied this method for extraction of D-pinitol from carob pods. ...
Cyclitols are cycloalkanes with one hydroxyl group on each of three or more ring atoms, also called cycloalkane polyols or sugar alcohol which attract attention since they have numerous pharmaceutical properties and are widespread in the plants. Inositols are important cyclitols, which constitute a group of naturally occurring polyhydric alcohols and some isomers of this group can be commonly found in most plants, provided adequate methods of detection are employed. This review presents plant containing cyclitols, with emphasis put on their pharmaceutical properties. The text focuses on sample preparation, extraction and purification and on analysis of cyclitols in plants. In addition, it addresses the application of different methodologies utilized in the analysis of cyclitol compounds in plant.
... This natural compound, related to the important family of inositols, is present in carob in high levels and increases this Leguminosae's value due to its pharmacological importance related to anti-cancer, anti-diabetic, antioxidant, and anti-ageing properties . Besides the classic extraction associated with the syrup carob production, D-pinitol extraction from carob pulp was studied using microwave (Ersan et al., 2020), supercritical CO 2 (Cháfer & Berna, 2014) and ultrasound (Tetik & Yüksel, 2014) techniques. Finally, the carob seed consists of three parts: the peel (husk), the endosperm and the germ. ...
Background
Carob (Ceratonia siliqua L.) is an evergreen tree that belongs to the Leguminosae family and is typical of the Mediterranean basin. It is well known for its valuable locust bean gum obtained from carob seeds. However, the food industry can obtain different carob products from carob fruit after processing. Carob products are good sources of dietary fibre, sugars, and a range of bioactive compounds such as polyphenols and D-pinitol.
Scope and approach
Bioactive compounds present in carob fruit and its derived products help control many health problems such as diabetes, heart diseases, and gastrointestinal disorders due to their anti-hyperglycaemic, antioxidant, and anti-inflammatory activities. So, carob products have a great potential to be used as a functional food ingredient.
Key findings and conclusions
This article focuses on carob characteristics and processing, chemical composition, health benefits, and applications in food formulations to explore the potential of carob in developing a wide variety of health-beneficial food products.
... Additionally, D-pinitol was isolated from carob pods using supercritical fluid extraction (SFE). The influence of SFE crucial parameters such as pressure, temperature, CO 2 flow rate and process duration were studied [11]. Chauhan et al. isolated D-pinitol from the aqueous fraction of the herb Argyrolobium roseum by HPLC analysis with RI/PDA (refractive index/photodiode array) detector [12]. ...
D-pinitol (3-O-methyl-D-chiro-inositol) is a well-known bioactive compound with anti-diabetic and anti-oxidant biological functions. A gas chromatography–mass spectrometry (GC–MS) method was developed for its quantitation in carob syrup, flesh and seed samples originated from Cyprus. The analysis was performed after derivatization of carbohydrates and polyols into trimethylsilyl ether derivatives. D-pinitol was determined in 13 carob syrup samples, in concentrations ranging 65.71 ± 4.60 – 77.72 ± 5.44 mg/g (mean: 68.58 ± 4.80 mg/g, n = 13). In two commercial samples, it was determined in relative medium-low concentrations (21.96 ± 1.54 and 44.71 ± 3.13 mg/g), revealing possible adulteration; however, this needs further investigation. Similarly, it was determined in high concentrations in carob flesh samples, in concentrations ranging 53.20 ± 3.72 – 54.58 ± 3.82 mg/g (mean: 53.81 ± 3.76 mg/g, n = 3). On the other hand, seed samples proved very poor in D-pinitol (<LOD). Therefore, bioprospecting of carob fruit and syrup is highlighted. Compared to other plants or legumes, carob appears to be the richest source of D-pinitol, highlighting carobs role as a functional organic food. The historical and cultural association of Cyprus with carobs is linked with traditional foods and habits.
... Several studies continue to deepen on the extraction and mainly with the use of new technologies such as ultrasounds, microwaves, and supercritical fluids. Different vegetable sources were studied such as grape pomace [1], grape marc [2], black chokeberry [3], lemongrass (Cymbopogon flexuosus) [4], microalga (Chlorella sp.) [5] and carob [6][7][8]. Generally, the studies consist of the description of the kinetics or see the effect of the operating parameters on the extraction yield to optimize the processes. ...
Purpose
A new approach was proposed to model the extraction kinetics according to the operating parameters. This approach is based on the determination of the critical time tc (a characteristic time which depends on the operating parameters).
Methods
It is necessary to start by collecting the experimental values of tc from experimental kinetics using the second derivation of extraction yield. Then, a full factorial design 2³ is used to model tc as function of studied factors: temperature, solid-liquid ratio and ultrasonic power. The obtained expression of tc was used in second time as the basis of the modeling of extraction kinetics. It made possible to locate the inflection point that separates the two intervals of the extraction. To assure continuity in this point, we changed variable of time for the second phase of extraction and we started fitting from the last calculated point from the first phase. Seven models were tested to fit studied kinetics.
Results
A mathematical model was proposed to express tc according to the operating parameters of the studied extraction. Patricelli (composed of two exponential terms) and the exponential models showed the best fitting results for all experiments. Patricelli model fitted very well the first phase of experiments and the exponential model fitted the second phase.
Conclusion
This confirms a new coupled washing/diffusion hypothesis of extraction performing in three steps: washing, first diffusion step, and second diffusion step.
... Carob powder contains daily nutritional amount of potassium, calcium, magnesium, and iron [15,36]. It is reported that carob comprises a high amount of pinitol, which has beneficial effects on human health, such as the regulation of blood glucose levels and reduction of hyperlipidemia and inflammation [37,38]. Containing a large amount of bioactive compounds, carob kibble has shown good antioxidant activities [2,10,39,40], anticancer and antiproliferation effects [41], antidiabetic effect [42,43], cholesterol lowering effect [44,45], and antimicrobial effects [23] and it has positive effects on cardiovascular diseases [42,46]. ...
The main objective of this research was to compare physicochemical parameters, antioxidant activity, lipid composition, and sensory analysis of initial and roasted carob pod powder ( Ceratonia siliqua L.) obtained at different roasting temperatures. The roasted products became darker and the average moisture content, water activity, oil content, and sweetness values decreased at higher temperatures. Total polyphenol content and antioxidant activity increased with increasing roasted temperature. Oleic acid, linoleic acid, and palmitic acid were the main fatty acids present in carob oil. Results showed that the roasted carob pod powders are sweeter, have more caramel-like taste, and have more cacao-like aroma at lower roasting temperatures but have more astringent taste, coffee-like aroma, and roasted aroma at higher roasting temperatures.
... A large number of kinetic models can be found in the literature, which were developed to represent the OEC of SFE processes, including simple correlations based on first order kinetics, such as the Barton model (Ch afer and Berna, 2014;Nguyen et al., 1991;Silva et al., 2011Silva et al., , 2008, to comprehensive phenomenological models based on mass transfer differential made in the cell extraction (De Melo et al., 2014;Huang et al., 2012;Oliveira et al., 2011). Yet, more limited approaches and studies are available in the literature regarding SFE scaling. ...
The supercritical fluid extraction (SFE) of vegetal raw materials is a large field of research, innovation and entrepreneurial developments. Optimization of process conditions is usually accomplished in analytical or laboratory scale equipment. Although SFE scaling is essential to attain industrial applications, studies in the literature are scarce. In this work, the kinetic behavior of 19 overall extraction curves (OEC's), obtained by the authors in previous works using NOVALINDUS Platform SFE facilities, and a set of 39 OEC's published by other authors, were considered all together to study SFE scaling. A general trend between the solvent flow rate and Barton kinetic constant was obtained for all extraction curves included in the data base, which comprise 10 different plant materials, temperatures in the range 298–333 K, pressures of 10–30 MPa, extractor volumes from 50 to 5200 cm³, particle diameters from 250 to 1400 μm and bed porosity in the range 0.59–0.97.
... The concentration or purification of compounds of interest could be a cumbersome task due to the existence of many different compounds; for instance d-pinitol is obtained from carob extracts by chromatography (Chafer and Berna, 2014). This is a costly and slow process. ...
Synthetic methods of grafting silica with (3-(2,3-epoxypropoxy)-propyl), polyoxyethylated isooctylphenolic, polyethylene glycol octadecyl ether and polyethylene glycol hexadecyl ether groups have been explored. Structure of final materials was investigated by elemental and differential thermal analyses, 13C NMR and FTIR. According to TGA and elemental analysis, data transformation of silanol groups to 2,3-epoxypropoxypropyl groups reaches up 67.61% and 61.02%, respectively. Novel silica-based solid-phase extraction (SPE) cartridges with surface-immobilized of polyoxyethylated isooctylphenolic, polyethylene glycol octadecyl ether and polyethylene glycol hexadecyl ether groups can be prepared with satisfactory densities: 20–30 µmol g⁻¹. Limit of detection of myo-inositol in water-acetonitrile samples (40/60%) is characterized by 1.27 μg per column. Applicability of proposed method using novel SPE cartridges for analysis of myo-inositol in Medicago Sativa L. gives 2.6 g of Myo-In per 1 kg of leaves.
Guayule (Parthenium argentatum) is a woody shrub native to the southwestern US that produces rubber in its stems. In the production of guayule hard rubber for tires, two residue streams are produced: a complex resin liquid and a ground, dry woody bagasse. Identifying higher-value products and applications for these residues is a goal of the Logistics and Co-Products thrust of the Sustainable Bioeconomy for Arid Regions (SBAR) USDA Coordinated Agricultural Project. Here, we summarize the current knowledge of guayule resin chemical composition, extraction methods used to isolate guayule resin fractions, and promising applications for these fractions. The most abundant compounds include terpenes and terpenoids, phenolics, alkaloids, sterols, and fatty acids/triglycerides, and low-molecular-weight rubber. Unique to guayule are guayulins and argentatins, which are expected to have some degree of bioactivity. Common extraction methods include Soxhlet extraction, steam distillation, maceration, percolation, pressurized- liquid extraction, supercritical fluid extraction, ultrasound-assisted extraction, microwave-assisted extraction, and several other experimental techniques. Resin mixtures are extremely complex, ranging from volatile to non-volatile, and from thermally stable to very delicate, molecules. Potential applications include tackifiers, adhesives, coatings, composite components, and those for essential oils: bio-control agents, insecticides, antimicrobials, antifungals. Separation optimization focuses on maximizing total economic value of extractable fractions, increasing the scale and robustness of extraction methods, and lowering the operational costs and environmental impacts of extraction processes.
This study investigates the effects of temperature (50–80 °C), time (10–60 min), carob-to-solvent ratio (2–8 g/40 mL), and solvent concentration (0–50 ethanol/water%, v/v) on microwave-assisted extraction of d-pinitol compound from carob fruit with optimization using Box–Behnken design. The optimal conditions for maximum d-pinitol yield (64.16 g/kg dry sample) include 50 °C temperature, 5.6 g carob/40 mL solvent, water used as a solvent, and an extraction time of 10 min. The fitness of the model was determined by ANOVA analysis with a high coefficient (R2 = 0.9057). Extraction was performed under optimum conditions for model validation, and 63.89 g/kg dry sample of d-pinitol extraction was achieved. In addition, the effects of the same variables on the total phenolic (TP) content of MEA extraction of carob were also investigated. Extraction efficiency of 426 g/kg was obtained under the optimum conditions determined for TP (80 °C, 8 g of carob, 50% ethanol, and 10 min), but it was observed that TP content decreased to 49.7 g/kg under optimum conditions determined for d-pinitol. Sucrose, glucose, and fructose sugar contents of the extract were determined only for optimum conditions for d-pinitol, and the fructose content was found to be the lowest. Determining the d-pinitol, TP, and sugar contents of the extract in optimum condition confirms the direct usability of the extract, because only water is used as a solvent. Conventional extraction method was carried out at 50 °C for control purposes, yielding 42.83 g/kg of d-pinitol, thereby supporting the effect of the microwave on extraction.
The aim of the present study was to develop an optimization procedure for supercritical fluid extraction parameters, in order to obtain the highest possible yield of sugars and cyclitols from plant material. Response surface methodology based on Box‐Behnken design was applied to evaluate the effect of: temperature (40, 60, 80 °C), pressure (100, 200, 300 bar), and co‐solvent (methanol) percentage (20, 25, 30%). As a result of the optimization process, we found that the highest amount of sugars (15.02 mg.g‐1of dried material) and cyclitols (0.86 mg.g‐1 of dried material) was obtained when the following parameters were applied: 80 °C, 228 bar, and 30% of methanol. Moreover, co‐solvent concentration and temperature had a higher influence onto the obtained amounts compared with the pressure. This article is protected by copyright. All rights reserved
The carob is a dome-shaped evergreen tree that is a member of the pea family (Fabaceae). Its fruit has been used for human consumption and as animal feed in the Mediterranean countries for centuries and was also widely used as a herbal remedy in traditional folk’s medicine. In this paper, an in-depth literature review was conducted about this species discussing its history, origins, main current uses, components (both nutrient and bioactive), biological activities, and potential applications as the source of sustainable ingredients and products. Among the many bioactive compounds that were found in carob, the most well studied are polyphenols. The levels of these compounds were found to vary depending on many factors, such as the variety, plant part, geographic location, roasting and extraction conditions, and even analysis methods. In the light of these researches, it was recognized that carob offers several biological activities including antioxidant, anticancer, and anti-diabetic due to the presence of a high quantity of pinitol and antibacterial. Rich in sugars, proteins, and minerals, the carob has a vast range of industrial applications such as cacao substitute, sugars substitute, free from gluten making it cereal-derived foods for celiac people.
Using the molecular dynamics simulation, the effect of methanol, ethanol and propanol solvents on the interaction of CO2 with methimazole, propranolol and phenazopyridine was studied under subcritical and supercritical conditions. The density of studied systems was calculated at different temperatures and pressures and relative error values were obtained. The results show good agreement with experimental data. The results revealed that methanol altered the aggregation of CO2 around phenazopyridine in supercritical conditions and increased aggregation, while for methimazole and propranolol, propanol cosolvent was more effective than other two alcohols on the aggregation of CO2 around the drug. Also, the aggregation of solvents around phenazopyridine occurs more than two other drugs. The analysis of weak interactions was performed based on Local Orbital Localization and it was determined that hydrogen interactions and steric effects of the drug ring and cage structures of CO2 play a greater role than the Van der Waals interaction.
Based on the bioactive properties of certain compounds, such as antioxidant and anti‐inflammatory activities, an interesting subject of research are natural substances present in various parts of plants. The choice of the most appropriate method for separation and quantification of biologically active compounds from plants and natural products is a crucial step of any analytical procedure. The aim of this review article is to present an overview of a comprehensive literature study from the last ten years (2007‐2017), where relevant articles exposed the latest trends and the most appropriate methods applicable for separation and quantification of biologically active compounds from plant material and natural products. Consequently, various extraction methods have been discussed, together with the available procedures for purification and pre‐concentration and dedicated methods used for analysis.
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Cyclitols are phytochemicals naturally occurring in plant material which attracted an increasing interest due to multiple medicinal attributes, amongst the most important are the anti-diabetic, antioxidant and anti-cancer properties. Due to their valuable properties, sugars are used in food industry as sweeteners, preservatives, texture modifiers, fermentation substrates, flavoring and coloring agents. In this study we report for the first time the quantitative analysis of sugars and cyclitols isolated from Solidago virgaurea L. (S. virgaurea) which was used for the selection of the optimal solvent and extraction technique that can provide the best possible yield. Moreover, the quantities of sugars and cyclitols extracted from other two species, Solidago canadensis (S. canadensis) and Solidago gigantea (S. gigantea) were investigated using the best extraction method and the most appropriate solvent. Comparative analysis of natural plant extracts obtained using five different techniques – maceration, Soxhlet extraction, pressurized liquid extraction (PLE), ultrasound assisted extraction (UAE), and supercritical fluid extraction (SFE) – was performed in order to decide the most suitable, efficient and economically convenient extraction method. Three different solvents were used. Analysis of samples has been performed by solid phase extraction (SPE) for purification and pre-concentration, followed by derivation and GC-MS analysis. The highest efficiency for the total amount of obtained compounds has been reached by PLE, when water was used as a solvent. D-pinitol amount was almost similar for every solvent and for all extraction technique involved.
To assess the effects of soybean-derived pinitol on glycaemic control and cardiovascular risk factors in Korean patients with type II diabetes mellitus.
Randomized, double-blind, placebo-controlled, parallel-group trial.
Pusan Paik Hospital, Pusan, Republic of Korea.
A total of 30 patients with type II diabetes received an oral dose of 600 mg soybean-derived pinitol or placebo twice daily for 13 weeks.
Pinitol significantly decreased mean fasting plasma glucose, insulin, fructosamine, HbA1c, and the homeostatic model assessment insulin resistance index (HOMA-IR, P<0.001). Pinitol significantly decreased total cholesterol, LDL-cholesterol, the LDL/HDL-cholesterol ratio, and systolic and diastolic blood pressure and increased HDL-cholesterol (P<0.05).
These data suggest that soybean-derived pinitol may be beneficial in reducing cardiovascular risk in Korean type II diabetes.
Endogenous low-molecular-weight glycans containing pinitol (3-O-methyl-D-chiro-inositol) and D-chiro-inositol are thought to mediate certain actions of insulin. We tested the hypothesis that oral administration of soybean-derived pinitol would improve insulin sensitivity in obese subjects (BMI = 36.6 kg/m2) with diet-treated type 2 diabetes or glucose intolerance (HbA1c = 6.8%).
There were 22 subjects randomized to receive either pinitol 20 mg x kg(-1) x day(-1) (n = 12) or placebo (n = 10) in a 28-day double-blinded trial.
No toxicity due to the pinitol was observed during the study The sensitivity of glucose and lipid metabolism to insulin were assessed by measurement of whole-body glucose, palmitate, and glycerol kinetics during basal conditions and a hyperinsulinemic-euglycemic clamp. Metabolic measurements were made at baseline and again at the end of the study Final plasma levels of pinitol were 48-fold (1.06 +/- 0.15 vs. 0.02 +/- 0.01 micromol/l, P < 0.0001) and D-chiro-inositol levels 14-fold (0.56 +/- 0.08 vs. 0.04 +/- 0.02 micromol/l, P < 0.0001) greater in the pinitol group compared with placebo.
Four weeks of pinitol treatment did not alter baseline glucose production, insulin-mediated glucose disposal, or rates of appearance of free fatty acids and glycerol in plasma. We conclude that plasma levels of both pinitol and D-chiro-inositol are very responsive to pinitol ingestion, but insulin sensitivity does not increase after pinitol treatment in individuals with obesity and mild type 2 diabetes.
Myoinositol is an essential component of all animal cells and is found in plants, fungi, and some bacteria.1 According to Billington,2 myoinositol was first identified in cardiac muscle by Scherer in 1850. It is a component of membrane phospholipids, and the function of these membrane phosphoinositides may prove to be important to the action of insulin, as discussed later. Myoinositol, a cyclitol, is the most common of the nine isomers of hexahydroxycyclohexane. Two stereoisomers of myoinositol are D-chiroinositol and L-chiroinositol. In humans myoinositol is found mainly either in its free form or covalently bound to phospholipid, with three principal forms: phosphatidylinositol (PI), phosphatidylinositol-4-P (PIP or PI-4-P), or phosphatidylinositol 4,5-P2 (PI-4,5-P2 or PIP2). The structures of myoinositol, of D-chiroinositol, and of several phosphatidylinositols are shown in Figure 1.
D-Pinitol, the major constituent of soybean plant is known as an insulin mimicker. There is a growing interest in the use of D-Pinitol as a food supplement because of its reported efficacy in lowering blood glucose levels with no side effects and nil toxicity. Pinitol was first isolated from pine tree and later from many plants of the Leguminosae family. DPinitol has been recently reported from Pisonia alba (synonym- Pisonia grandis) of the Nyctaginaceae family (Patent Pending 385/CHE/2010). As the demand for pinitol as a food supplement and as a pharmaceutical increased, any attempt to isolate it from natural sources including plants is considered highly worthy. This review covers literature reported on isolation of D-Pinitol from plants during the period 1940 to May 2011.
The carob pod, an important fruit of the food industry in the production of concentrated syrup, is rich in potentially health-promoting phenolic compounds and sugars. Moreover, one of the important bioactive components of carob is D-pinitol, and it has some beneficial effects on human metabolism. The optimum conditions for extraction of D-pinitol and total phenolic compounds (TPC) from cultivated and wild types of carob pods were determined using response surface methodology (RSM). The Box-Behnken Design (BBD) was used to investigate the effects of three independent variables; extraction temperature (degrees C), dilution rate (w/v), and extraction time (h) on the response, D-pinitol and the total phenolic compounds. The optimum extraction conditions obtained using the response optimizer were an extraction temperature of 80 degrees C, a dilution rate of 1:4, and an extraction time of 2h. Under the mentioned above conditions, the maximum D-pinitol and TPC concentrations were 9.67 g/L and 5916.55 mg/L in wild carob pod extract, respectively.
Peppermint and spearmint oils were extracted from cut green plants and field-dried hay with liquid and supercritical carbon dioxide at 297 to 316 K and 6 to 18 MPa. Solvent treatment was varied from 6 to 30 g CO2/g dry plant material. Extraction time was varied from 4 to 9 hours. Extraction vessel charge sizes were 4.4 and 33 L. Downflow of carbon dioxide through the bed of mint plants was more effective than upflow. Essential oil compositions and attainable yields were nearly the same as those by steam distillation when single pass mode of CO2 with depressurization to atmospheric pressure was used for oil recovery. The recovery of the terpene constituents was reduced when using depressurization to 3–6 MPa for oil recovery and recycle of CO2. The flavor and fragrance of the carbon dioxide mint extracts were closest in quality to actual mint plant leaves, compared to mint oils produced by conventional steam distillation.
Different plant materials including cardamom, clove, cumin, fennel, ginger, parsley and sandelwood were extracted with liquid carbon dioxide under liquid—vapor conditions. The novel apparatus used is described in some detail. The extraction with CO2 is compared to the conventional steam distillation. The yields of the extraction and of the distillation were determined quantitatively and the extracts were analysed by thin layer and by gas chromatography. The yields of the CO2 extractions were 10 % to 360 % larger than the yields of the steam distillations, while the extraction time is only to of the time needed for distillation. The yield of the extractions as function of time can be described by a simple equation. The energy consumption of the extraction process is approximately a factor of three lower than the energy required for steam distillation.
Measurements of d-pinitol solubility in supercritical CO2 in the temperature range (313 to 333) K and pressures ranging from 10 to 40 MPa are reported for the first time in this work. Two different thermodynamic models are applied to correlate the experimental d-pinitol solubilities: a cubic-type equation of state (the Soave−Redlich−Kong, SRK) and a model based on the group contribution approach (the Group Contribution Equation of State, GC-EoS). Both models demonstrate high capability to describe the solid−gas-phase equilibria of this system. In addition, values for the thermophysical properties, sublimation pressure, and solid molar volume of d-pinitol are also given.
Supercritical fluid extraction possesses several advantages over traditional liquid-solvent-based extraction methods, including improved selectivity, expeditiousness, automation and environmental safety. Fluid-phase equilibrium data are essential for studying the viability of supercritical extraction and the design of the extraction columns often used for this type of separation. Resveratrol has been correlated with serum lipid reduction and inhibition of platelet aggregation, and its cancer chemopreventive activity has recently been reported. The extraction of resveratrol using supercritical CO2 is not possible; it only extracts traces of product, probably due to its polar nature. So, it is necessary to use a co-solvent. Ethanol is appropriate because it is a polar solvent permitted in the food industry. This work uses different mixtures of ethanol–CO2, ranging from 5 to 15% of ethanol, to optimise the amount of resveratrol extracted. The solubility of resveratrol in the supercritical solvent was measured at 313 K and pressures ranging from 80 to 140 bar. In order to correlate the results obtained, two equations of state were successfully used (Peng–Robinson (PR) and Soave–Redlich–Kwong (SRK)). These equations show similar deviations, but PR shows a better correlation with experimental data. The solubility of resveratrol shows a maximum at an intermediate value of percentage of ethanol. It is roughly 7.5% of ethanol. So the optimal concentration of co-solvent was found. This solubility rises with pressure.
Supercritical CO2 extraction of essential oils is one of the most widely discussed applications in the supercritical fluid literature. Nevertheless, a comprehensive overview of the analytical, processing and modeling aspects has never been attempted. This is partly due to the difficulties involved in isolating essential oils from the other products which supercritical CO2 can dissolve. Moreover, only a limited number of studies provide quantitative data on the parameters governing this process.In this review, solubility data on pure compounds belonging to essential oils are analyzed. Processes proposed to isolate and fractionate essential oils by supercritical CO2 and the corresponding modelling aspects are discussed critically.
D-pinitol (3-O-methyl-chiroinositol), an active principle of the traditional antidiabetic plant Bougainvillea spectabilis, is claimed to exert insulin-like effects. This study investigates the effect of D-pinitol on glucose homeostasis in animal models of diabetes, and on glucose transport by cultured muscle cells.
Plasma glucose concentrations were measured in normal, obese-diabetic (ob/ob) and streptozotocin (STZ)-diabetic mice after oral (p.o.) and intraperitoneal (i.p.) administration of D-pinitol. Glucose transport was measured in L6 rat muscle cells by 2-deoxyglucose (2DG) uptake.
In STZ-diabetic mice, 100 mg kg−1 p.o. D-pinitol acutely decreased the hyperglycaemia (by 22% at 6 h). A similar decrease in plasma glucose (by 21%) was observed after 100 mg kg−1 i.p. D-pinitol. Insulin concentrations and the rate of insulin-induced (1 unit kg−1 actrapid i.p.) glucose disappearance were not altered by 100 mg kg−1 p.o. D-pinitol. Chronic administration of D-pinitol (100 mg kg−1 i.p. twice daily for 11 days) to STZ-diabetic mice maintained a reduction in plasma glucose concentrations from about 14 to 10 mmol l−1.
In normal non-diabetic and severely insulin resistant ob/ob mice, 100 mg kg−1 p.o. D-pinitol did not significantly affect plasma glucose or insulin during acute studies.
Incubation of L6 muscle cells with D-pinitol (10−3 M) increased basal 2DG uptake by 41% after 10 min and by 34% after 4 h. The effect of D-pinitol was inhibited by the phosphatidylinositol 3-kinase inhibitor LY294002. D-pinitol did not increase insulin-stimulated 2DG uptake by L6 cells.
The data support the view that D-pinitol can exert an insulin-like effect to improve glycaemic control in hypoinsulinaemic STZ-diabetic mice. D-pinitol may act via a post-receptor pathway of insulin action affecting glucose uptake.
British Journal of Pharmacology (2000) 130, 1944–1948; doi:10.1038/sj.bjp.0703523
In the carrageenin-induced paw oedema in rats, (+)-pinitol (2.5-10 mg/kg, i.p.), isolated from Abies pindrow leaves, showed a significant anti-inflammatory effect, the highest dose being comparable to phenylbutazone (100 mg/kg, i.p.).
We isolated from beef liver a putative insulin mediator termed INS-2, 1. Its structure was determined to be a novel inositol glycan pseudo-disaccharide Mn(2+) chelate containing D-chiro-inositol 2a (as pinitol) and galactosamine. Purification methods were scaled up from those previously reported to isolate an inositol glycan with similar composition from rat liver.(1) Structure of the beef liver glycan was determined by degradative chemistry and 2D NMR spectroscopy and confirmed by chemical synthesis. Its structure is 4-O-(2-amino-2-deoxy-beta-D-galactopyranosyl)-3-O-methyl-D-chiro-inositol 1 (INS-2, Figure 1). Its role as an insulin mimetic was demonstrated by its action in vivo to decrease elevated blood glucose injected to low-dose streptozotocin diabetic rats in a stereospecific and dose-dependent manner. The pseudo-disaccharide also stimulated [(14)C]glucose incorporation into [(14)C]glycogen in a dose-dependent manner in H4IIE hepatoma cells in the presence of insulin, thus enhancing insulin action. Only when chelated to Mn(2+) did it activate pyruvate dehydrogenase phosphatase in vitro in a dose-dependent manner. To our knowledge, this is the first example of a beta-1,4-linked inositol glycan consisting of D-chiro-inositol and galactosamine isolated from animal tissues with insulin mimetic actions.
Glucosamine increases flux through the hexosamine pathway, causing insulin resistance and disturbances similar to diabetic glucose toxicity.
This study examines the effect of glucosamine on glucose uptake by cultured L6 muscle cells as a model of insulin resistance.
Glucose uptake by L6 myotubes was measured using the non-metabolized glucose analogue 2-deoxy-d-glucose after incubation with glucosamine for 4 and 24 h, with and without insulin and several other agents (metformin, peroxovanadium and d-pinitol) that improve glucose uptake in diabetic states.
After 4 h, high concentrations of glucosamine (5 x 10(-3) and 10(-2) M) reduced basal and insulin-stimulated glucose uptake by up to 50%. After 24 h, the effect of insulin was completely abolished by 10(-2) M glucosamine and reduced over 50% by 5 x 10(-3) M glucosamine. Lower concentrations of glucosamine did not significantly alter glucose uptake. The effect of glucosamine could not be attributed to cytotoxicity assessed by the Trypan Blue test. Metformin, peroxovanadium and d-pinitol, each of which increased glucose uptake by L6 cells, did not prevent the decrease in glucose uptake with glucosamine.
Glucosamine decreased insulin-stimulated glucose uptake by L6 muscle cells, providing a potential model of insulin resistance with similarities to glucose toxicity. Insulin resistance induced by glucosamine was not reversed by three agents (metformin, peroxovanadium and d-pinitol) known to enhance or partially mimic the effects of insulin.
Procedimiento de extracción y purificación de pinitol y extracto enriquecido en el mismo
- A Berna
- A Chafer
- C Pascual-Martí
- A Salvador
A. Berna, A. Chafer, C. Pascual-Martí, A. Salvador, Procedimiento de extracción
y purificación de pinitol y extracto enriquecido en el mismo, Patent n • ES 2 322
883 B1.
Method of obtaining pinitol from carob
- B Macias
- C Sanjuán
B. Macias, C. Sanjuán, Method of obtaining pinitol from carob, U.S. Patent, 6,
699,511, 2001.