Hydroxycitric Acid Lactone Research Articles

Prophylactic function of Garcinia morella dried fruits in preventing intestinal barrier disruption by lowering tight junction permeability and inflammation

The most frequent cause of gastrointestinal disorders characterized by inflammation and disturbance of the gastrointestinal system, is infection from various bacterial strains. Garcinia morella (Gaertn.) Desr. (Clusiaceae) a well-known traditional food is also used in healing digestive disorders for centuries. However, its protective activity in the pathogenesis of pathogen-induced gut disruption remains unclear. This study investigated the beneficial effect of G. morella fruits in remediating pathogen-induced intestinal disruption in Caco-2 cells. The antimicrobial activity of G. morella hydroalcoholic fruit extract with known chemical composition against the opportunistic pathogens, Escherichia coli and Enterococcus faecalis were evaluated. Transepithelial electrical resistance and dextran permeability assay were performed to evaluate the permeability in Caco-2 monolayers. Western blot assays were performed to detect the expression of the intestinal tight junction proteins: zonula occludens-1, claudin-1, occludin, and E-cadherin; and phosphorylation of inflammatory markers: ERK (Extracellular signal-regulated kinase), and JNK (Jun N-terminal kinase). Three bioactive compounds: garcinol, hydroxycitric acid, and hydroxycitric acid lactone were identified, qualitatively and quantitatively assessed with HPLC (high performance liquid chromatography). G. morella hydroalcoholic extract and its compounds prevented the decrease in transepithelial electrical resistance caused by pathogen infection in Caco-2 cells. G. morella and compounds also decreased permeability in Caco-2 monolayer, increased by pathogen infection. G. morella and garcinol enhanced tight junction protein expression. A decrease in extracellular-signal-regulated kinase and c-Jun N-terminal kinase phosphorylation was observed in G. morella and garcinol-treated cells. Overall, the results showed the potential of G. morella and its compounds in maintaining intestinal integrity and validate its traditional claims in ameliorating stomach ailments. The study also provided new guidance in development of nutraceuticals that aid in curing leaky gut.

Plant Growth Inhibitory Activity of Hibiscus sabdariffa Calyx and the Phytotoxicity of Hydroxycitric Acid Lactone

Weeds pose major constraints in crop production. The use of allelochemicals and allelopathic species can provide an effective alternative for sustainable weed management. In a previous study that evaluated the allelopathic activity of wild and cultivated plants in Turkey, Hibiscus sabdariffa demonstrated the strongest inhibitory potential. This study aimed to estimate the phytotoxic influence of the H. sabdariffa water crude extracts on Lactuca sativa L. in a bioassay experiment. High-performance liquid chromatography (HPLC) analysis was used to identify two major compounds, hydroxycitric acid lactone and hydroxy citric acid, and their plant growth inhibitory activities were evaluated by bioassays. Hydroxycitric acid lactone had a stronger growth inhibitory activity on L. sativa L. and was estimated as a major allelochemical in H. sabdariffa calyx. The high concentration (16.7% of the dry weight of the calyx) and strong inhibitory effect (EC50, 73.7 ppm) of the hydroxycitric acid lactone could demonstrate the growth inhibitory activity of the H. sabdariffa calyx extract. This study showed that hydroxycitric acid lactone, a major compound in the calyx of Hibiscus sabdariffa, is a plant growth inhibitor.

Antibacterial Activity and Phytochemical Screening of Garcinia pedunculata Roxb. ex Buch. - Ham. fruit extract by HPLC–ESI-MS

Disc and well diffusion methods were used to test the antibacterial activity of methanol extract and ethanol extract of the selected ethnomedicinal plant viz. Garcinia pedunculata Roxb. ex Buch.-Ham. Both the methanol extract and ethanol extract were subjected to antibacterial activity assay against the six clinical isolates. Antibiotic sensitivity test of the test bacteria against standard antibiotics were also determined. All the bacterial pathogens (Staphylococcus aureus, Enterococcus faecalis, Enterobacter cloacae, Escherichia coli, Pseudomonas aeruginosa and Klebsiella pneumoniae) were exposed to the plant extract in triplicates. The investigation revealed the potency of G. pedunculata extract as an effective antibacterial agent against both Gram-positive bacteria (GPB) and Gram-negative bacteria (GNB). G. pedunculata are evaluated to be bactericidal against the tested bacteria. The antibacterial activity may be due to an individual compound or synergistic effect of more than one compound present in the medicinal plant extract. The minimum inhibitory concentrations (MIC) and minimum bactericidal concentrations (MBC) of the plant extracts were also investigated by using the broth microdilution method. HPLC-MS of the methanol extract of G. pedunculata fruit revealed the presence of Hydroxy Citric Acid Lactone (MW-190), Garcinone-E (MW-464), a-Mangostin (MW-410), β–Mangostin (MW-424), and γ-Mangostin (MW-396).

Authentication of Garcinia fruits and food supplements using DNA barcoding and NMR spectroscopy

Garcinia L. (Clusiaceae) fruits are a rich source of (−)-hydroxycitric acid, and this has gained considerable attention as an anti-obesity agent and a popular weight loss food supplement. In this study, we assessed adulteration of morphologically similar samples of Garcinia using DNA barcoding, and used NMR to quantify the content of (−)-hydroxycitric acid and (−)-hydroxycitric acid lactone in raw herbal drugs and Garcinia food supplements. DNA barcoding revealed that mostly G. gummi-gutta (previously known as G. cambogia) and G. indica were traded in Indian herbal markets, and there was no adulteration. The content of (−)-hydroxycitric acid and (−)-hydroxycitric acid lactone in the two species varied from 1.7% to 16.3%, and 3.5% to 20.7% respectively. Analysis of ten Garcinia food supplements revealed a large variation in the content of (−)-hydroxycitric acid, from 29 mg (4.6%) to 289 mg (50.6%) content per capsule or tablet. Only one product contained quantifiable amounts of (−)-hydroxycitric acid lactone. Furthermore the study demonstrates that DNA barcoding and NMR could be effectively used as a regulatory tool to authenticate Garcinia fruit rinds and food supplements.

Phytochemical Screening of Garcinia travancorica by HPLC-ESI-QTOF Mass Spectrometry and Cytotoxicity Studies of the Major Biflavonoid Fukugiside

Qualitative screening of multiclass secondary metabolites present in the fruits, leaves and stem bark extracts of Garcinia travancorica was carried out using HPLC-QTOF-MS analysis. Twenty-three compounds were identified in the fruits, leaves and stem bark; including two acids (hydroxycitric acid and hydroxycitric acid lactone), eight biflavonoids (morelloflavone, GB-1, GB-la, GB-2, GB-2a, fukugiside, xanthochymusside and GB-la glucoside), nine xanthones (α-mangostin, γ-mangostin, 1,5-dihydroxy-3-methoxyxanthone, garciniaxanthone E, 4-(I,1-dimethylprop-2-enyl)-1,3,5,8-tetrahydroxy-xanthone, garcinone A, garcinone B, garcinone C and polyanxanthone C) and four polyisoprenylated benzophenones (gambogenone, aristophenone A, garcinol and garciyunnanin A). Cytotoxicity studies of the major biflavonoid fukugiside reported from G. travancorica leaves revealed a dose-dependent cancer cell growth inhibition in A431 and HeLa cells. The antiproliferative effect appears to be due to the ability of fukugiside to induce S-phase arrest and apoptotic cell death. In HeLa cells, fukugiside reduced the expression of MAPKp38 by 26.1% compared with untreated control.

Cinatrins D and E, and virgaricin B, three novel compounds produced by a fungus, Virgaria boninensis FKI-4958.

Two new hydroxycitric acid lactone derivatives named cinatrins D (1) and E (2), and a new γ-lactam, virgaricin B (3), along with a known similar compound, virgaricin (4), were isolated from a fermentation broth of the fungus Virgaria boninensis FKI-4958. The absolute stereo structures of the new compounds were established by a combination of spectroscopic methods and chemical modifications. All three newly discovered compounds possessed weak antibacterial activity.

The chemistry and medicinal uses of the underutilized Indian fruit tree Garcinia indica Choisy (kokum): A review

Garcinia indica Choisy Syn Brindonia indica, commonly known as kokum and belonging to Guttiferae family, is a plant native to certain regions of India. The trees yield fruits annually in the summer season during the months of March to May. The fruits are green when raw and red to dark purple when fully ripe. They are used to prepare juice, pickles and as acidulant in curries. In the traditional Indian system of medicine the Ayurveda and in various folk systems of medicine, the fruit rinds and leaves are used to treat various inflammatory ailments, rheumatic pain and bowel complaints. The kokum butter prepared from the seed is of both commercial and medicinal use. Chemical studies have shown that the rind contains protein, tannin, pectin, sugars, fat, organic acids like (−)-hydroxycitric acid, hydroxycitric acid lactone and citric acid; the anthocyanins, cyanidin-3-glucoside and cyanidin-3-sambubioside; and the polyisoprenylated phenolics garcinol and isogarcinol. Preclinical studies have shown that kokum or and some of its phytochemicals possess antibacterial, antifungal, anti-ulcerogenic, cardioprotective, anticancer, chemopreventive, free radical scavenging, antioxidant and anti-obesity effects. The present paper reviews the nutritional value, the phytochemical compounds, traditional uses and validated pharmacological properties of kokum.

Hydroxycitric acid lactone and its salts: Preparation and appetite suppression studies

(−) Hydroxycitric acid lactone (HCAL) has been prepared in pure form (>98%) and converted into different salts of Group-IA and IIA metals with definite composition for the first time. The lactone is stable at room temperature but in aqueous solution it exists in equilibrium with its acid counterpart. An HPLC method has been developed to quantify (−) hydroxycitric acid (HCA) and its lactone. In-vivo studies, using male rats of the Wistar albino strain, revealed the interesting finding that HCAL exhibited better appetite suppression than did hydroxycitric acid. The continuous shift in equilibrium between HCA and HCAL due to the depletion of HCA in animal systems (slow release mechanism) could be the possible reason for this improved activity.

Capillary zone electrophoresis for separation and analysis of hydroxycitric acid and hydroxycitric acid lactone: Application to herbal products of Garcinia atroviridis Griff

Capillary zone electrophoresis (CZE) was developed for quantitative determination of hydroxycitric acid and hydroxycitric acid lactone in herbal products of Garcinia atroviridis Griff. Resolution optimization was investigated by varying type, concentration and pH of buffers. Using the pH 9.2 buffer containing 30 mM Na 2B 4O 7, 90 mM NaH 2PO 4 and 0.5 mM tetradecyltrimethyl ammonium bromide, baseline resolution ( R s > 1.5) was found for all analytes. Advantages of the developed CZE method include simple sample preparation, fast analysis time within 5 min and high accuracy and precision.

Improved Liquid Chromatographic Method for Determination of Organic Acids in Leaves, Pulp, Fruits, and Rinds of Garcinia

An improved liquid chromatographic (LC) method was developed for determination of organic acids in leaves, pulp, fruits, and rinds of Garcinia. At present, the commonly used LC method for analysis of organic acids in Garcinia extracts uses direct application of the extracts on the column. This practice gradually reduces efficiency of the column and shortens its life. In the improved method, the interfering substances such as pigments and xanthones were effectively removed by passing the aqueous extract through an ODS cartridge. With subsequent injection on a C18 reversed-phase column, using 6.0 mM phosphoric acid as the mobile phase with a flow rate of 1.0 mL/min and UV detection at 210 nm, the organic acids were determined in the extracts. The major organic acid was (-)-hydroxycitric acid at the level of 2.5, 0.8, 3.0, and 20.1% in leaf, pulp, fresh fruit, and dried rinds, respectively. Minor quantities of hydroxycitric acid lactone, oxalic acid, and citric acid were also identified. Limits of detection and recoveries were 0.9-1.5 microg and 93.9-99.8%, respectively. This is the first report on the composition of organic acids from Garcinia pedunculata.

Organic acids from leaves, fruits, and rinds of Garcinia cowa.

Organic acids in fresh leaves, fruits, and dried rinds of Garcinia cowa (G. cowa) were determined by high-performance liquid chromatography. Fresh leaves, fruits, and dried rinds were extracted with water at 120 degrees C for 20-30 min under 15 lbs/in(2) pressure. Also, dried rinds were extracted with solvents (acetone and methanol) using a Soxhlet extractor at 60 degrees C for 8 h each. The samples were injected to HPLC under gradient elution with 0.01 M phosphoric acid and methanol with a flow rate of 0.7 mL/min using UV detection at 210 nm. The major organic acid was found to be (-)-hydroxycitric acid present in leaves, fruits, and rinds to the extent of 1.7, 2.3, and 12.7%, respectively. (-)-Hydroxycitric acid lactone, and oxalic and citric acids are present in leaves, fruits, and rinds in minor quantities. This is the first report on the composition of organic acids from G. cowa.

Determination of organic acids in leaves and rinds of Garcinia indica (Desr.) by LC

Organic acids in leaves and rinds of Garcinia indica (Kokam) were determined by high-performance liquid chromatography. The major organic acid in leaves and rinds has been found to be (−)-hydroxycitric acid present to the extent of 4.1–4.6 and 10.3–12.7%, respectively, by isocratic elution with 8 mM sulfuric acid as mobile phase with a flow rate of 1.0 ml/min using UV detection at 210 nm. Hydroxycitric acid lactone and citric acid are present in leaves and rinds in minor quantities. This method has been shown to be very reproducible with the coefficient of variation ranging from 2.8 to 4.2%. This is the first report on the composition of organic acids in the leaves and rinds of G. indica by HPLC.

Separation of Hydroxycitric Acid Lactone from Fruit Pectins and Polyhydroxyphenols on Poly(4-Vinylpyridine) Weak-Base Resin

Poly(4-vinylpyridine) (PVP) has been used for the separation of hydroxycitric acid lactone (HCAL) from polyhydroxyphenols and fruit pectins, as the study has relevance to the problem of extraction of the antiobesity substance hydroxycitric acid from Garcinia cambogia fruits, a rich source of the acid. PVP has been used both in free-base form and in protonated or salt form as a sorbent, while catechol and pyrogallol have been used as representative polyhydroxyphenols. Though the protonated form, used as PVP(HCl), has a low sorption capacity (96 mg/g dry resin) and low selectivity for pectin (at pH 8), its higher, but comparable, sorptions (at pH 8) of HCAL, catechol, and pyrogallol, with respective saturation values of 354, 349, and 366 mg/g dry resin, coupled with high selectivity for the hydroxyphenols, make the sorbent unsuitable for the desired separation of HCAL. On the other hand, PVP free-base resin has significantly high sorption of HCAL as compared to catechol and pyrogallol in mildly acidic media (pH 1.8–2.8), the respective saturation values being 576, 206, and 303 mg/g dry resin, but the free-base resin also shows high saturation capacity (500 mg/g dry resin) for pectin. However, at low substrate concentrations (1 g/L) or relatively low pH (2), pectin has an order of magnitude lower sorption than HCAL, making separation of the latter possible on PVP free-base resin. Column operation using PVP free-base resin with influent maintained at pH 1.8, followed by stripping with less than the theoretical amount of alkali, produces good separation and high yield of HCAL from the mixed influent. Reillex HP, a macroporous PVP resin, used in free-base form, has relatively fast kinetics for HCAL sorption, with a t 1/2 value of about 5 minutes and diffusivity of the order of 10−6 cm2/s.

Separation of Hydroxycitric Acid Lactone from Fruit Pectins and Polyhydroxyphenols on Polybenzimidazole Weak-Base Resin

Polybenzimidazole (PBI) free-base resin has been used for selective sorption and recovery of hydroxycitric acid lactone (HCAL) from aqueous solutions containing also significant proportions of polyhydroxyphenols and fruit pectins, because the study has relevance to the problem of separation and recovery of HCAL, a potent antiobesity substance, from aqueous extracts of Garcinia cambogia fruits, grown largely in coastal areas of South India. PBI resin has the saturation sorption capacity of 315 mg/g dry resin for HCAL, compared with 131, 138, and 293 for catechol, pyrogallol, and pectin, respectively, in individual sorptions from aqueous solutions. The resin selectivity for HCAL over catechol, pyrogallol, and pectin in binary sorptions varies with pH, the separation factor of HCAL being maximum over catechol and pyrogallol at a pH of 1.7−1.8 and infinite over pectin at pH < 1.8. Under vigorous agitation the initial uptake of HCAL is very fast with 30% of the equilibrium sorption taking place in 10 s, followed by a significantly lower rate, leading to an overall 75% attainment of equilibrium sorption in 30 min. In continuous column operations with PBI resin and influent containing HCAL, polyhydroxyphenols, and fruit pectins, a proper combination of relatively low flow rate, a relatively low substrate pH (1.7−1.8), and “dead-end” stripping with alkali, which involves use of less than the theoretical amount of stripping agent necessary for complete stripping, produces an excellent separation and good yield of HCAL from the mixed influent.

Studies of Aliphatic Hydroxycarboxylic Acids as Antioxidants. III. The Preparation of Two Isomers of Hydroxycitric Acid Lactone (erythro- and threo-3,4-dicarboxy-3-hydroxy-γ-butyrolactone)

Studies of Aliphatic Hydroxycarboxylic Acids as Antioxidants. III. The Preparation of Two Isomers of Hydroxycitric Acid Lactone (<i>erythro</i>- and <i>threo</i>-3,4-dicarboxy-3-hydroxy-γ-butyrolactone)