phytosterols and n-hexane

Searching for green and ecofriendly solvents to replace classical solvents for industrial scale extraction of coconut oil is of great interest. To explore these possibilities, this study performed comprehensive comparative analyses of lipid profiles and phytosterol compositions in coconut oils obtained by extraction with n-hexane, absolute ethyl alcohol, deep eutectic solvent/n-hexane, dimethyl carbonate (DME) and cyclopentyl methyl ether (CPME) using a foodomics approach. Results indicated that CPME (64.23 g/100 g dry matter) and DME (65.64 g/100 g dry matter) showed comparable capacity for total lipid extraction of total lipids to classical solvents (63.5-65.66 g/100 g dry matter). Considering the phytosterol yield, CPME (644.26 mg/kg) exhibited higher selectivity than other solvents (535.64-622.13 mg/kg). No significant difference was observed in the fatty acid composition of coconut oil by the different solvents assayed. Additionally, total 468 lipid molecules were identified in the samples. For glycerolipid and sphingolipid, the five solvents showed comparable extraction capabilities. However, CPME exhibited higher extraction efficiency of polar lipids (glycerophospholipid and saccharolipid) than other solvents. Overall, these results may be a useful guide for the application of green solvents in industrial production of coconut oil.

Topics: Coconut Oil; Cocos; Lipidomics; Methyl Ethers; Phytosterols; Solvents

In this study, subcritical n-butane was adopted to extract oil from flaxseed. The extraction conditions i.e. extraction temperature, extraction time, and liquid-solid ratio were investigated and optimized by response surface methodology. The flaxseed oil obtained by subcritical n-butane were characterized and compared with those prepared by n-hexane and cold pressing. Results indicated that the optimal combination of parameters was 53.93℃, 56.82 min, and 19.98:1 mL/g. Subcritical n-butane had higher yield (28.75%) than n-hexane and cold pressing. GC analysis indicated that subcritical n-butane extraction had no obvious influence on the fatty acid composition. Nevertheless, the oil obtained by subcritical n-butane with higher contents of phytosterols (2.93 mg/g) and carotenoids (46.56 mg/kg), and presented a higher oxidation stability (9.27 h). Thus, it was suggested that subcritical n-butane extraction is a promising alternative to extract high quality flaxseed oil.

Topics: Butanes; Carotenoids; Fatty Acids; Flax; Food Quality; Hexanes; Linseed Oil; Liquid-Liquid Extraction; Oxidation-Reduction; Phytosterols; Temperature

Background Commelina benghalensis Linn. (Family: Commelinaceae) is a common weed available in Bangladesh with several uses in traditional medicine. However, the chemical profile of this medicinal plant is scarce in relation to its medicinal uses. The aerial parts of this plant have been investigated for the isolation of secondary metabolites and evaluation of the biological activities. Methods Major phytochemical groups were analyzed using chromogenic reagents, whereas n-hexane soluble fractionates of the methanol extract were subjected to 1H nuclear magnetic resonance (NMR) spectroscopic analysis. The antioxidant property of the obtained compounds was evaluated using 1,1-diphenyl-2-picryl-hydrazyl (DPPH). Results Dammara-12-en-3-one (CB-1), stigmasterol (CB-2) and 3 (2,3,4,5,6-pentahydroxy)-cinnamoyl dammara-12-ene (CB-3) were isolated from the n-hexane fractionate of methanol extract of C. benghalensis. In the study of DPPH radical scavenging activity, IC50 values were predicted to be 790.18, 4186.94 and 2001.16 μg/mL for CB-1, CB-2 and CB-3, respectively, whereas standard ascorbic acid showed IC50 at 1.26 μg/mL. Conclusions Two new dammarane-type triterpene (CB-1 and CB-3) and one phytosterol (CB-2) were identified in C. benghalensis with mild antioxidant property.

Topics: Antioxidants; Ascorbic Acid; Biphenyl Compounds; Commelina; Dammaranes; Hexanes; Phytochemicals; Phytosterols; Plant Extracts; Plants, Medicinal; Terpenes; Triterpenes

In this work, an enzymatic route for synthesizing phytosteryl lipoate was successfully set up for the first time. The structure of final product phytosteryl lipoate was determined by Fourier Transform Infrared (FTIR), Mass Spectrometry (MS) and Nuclear Magnetic Resonance (NMR). The maximum conversion of 71.2% was achieved when the following conditions were employed: 150mmol/L phytosterol, 1: 2.5M ratio of phytosterol to lipoic acid, 10g/L of 4Å molecular sieves and 60g/L Candida rugosa in 2-methyl-2-butanol/n-hexane (1:1, v/v) at 55°C for 96h. The physicochemical properties including solubility and antioxidant ability of phytosteryl lipoate in oil were assessed. The results revealed that phytosteryl lipoate possessed over twice as much oil solubility as free phytosterol and also showed better antioxidant ability. Investigation on its biological functions will be the main object in the future work.

Topics: Antioxidants; Hexanes; Pentanols; Phytosterols

Three new compounds; epi-mukulin, (Z)-Δ(1,2) dehydroguggulsterone and Δ(6,7)dehydro-20-hydroxygugglsterone were isolated from the n-hexane-soluble fraction (HSF) of the methanol extract of guggul, the oleogum resin of Commiphora wightii together with six known compounds: diasesartemin, (+)-epi-magnolin, (+)-diayangambin, gugglsterol I, (E)-guggulsterone and (Z)-guggulsterone. Their structures were elucidated on the basis of different spectroscopic data. α-Glucosidase inhibitory effects of HSF and the isolated compounds were evaluated calorimetrically. The HSF showed significant α-glucosidase inhibitory effect [IC(50) value of 140 µg mL(-1) (p < 0.05)]. Under the assay conditions, diasesartemin (IC(50) = 60.6 ± 0.01 µM) was found to be more potent than the positive control, acarbose (IC(50) = 92.94 ± 0.01 µM); a known α-glucosidase inhibitor (p < 0.05). The IC(50) values of epi-mukulin and (Z)-guggulsterone were found to be 159.33 and 132.14 µM, respectively. Other compounds showed weak α-glucosidase inhibitory effects, <30% inhibition of the enzyme activity at 0.1 mg mL(-1).

Topics: Analysis of Variance; Commiphora; Glycoside Hydrolase Inhibitors; Hexanes; India; Inhibitory Concentration 50; Methanol; Molecular Structure; Phytosterols; Plant Extracts; Plant Gums; Spectrophotometry, Infrared; Spectrophotometry, Ultraviolet

We recently reported the characterization of novel cholesterol esterase (EC. 3.1.1.13) from Trichoderma sp. and preliminary work on sterol ester synthesis. In the present study, we further examined the enzyme ability to synthesize cholesterol esters from cholesterol and free fatty acids of various chain lengths, and compared the fatty acid specificity in synthesis with that in hydrolysis. The enzyme catalyzed the synthesis of medium- and long-chain fatty acid cholesterol esters, but failed to synthesize short-chain fatty acid esters. The fatty acid specificities in the synthesis and hydrolysis of cholesterol esters were entirely different from each other. Unlike other lipolytic enzymes, the enzyme was largely independent of water content in the synthesis of cholesterol oleate, and it achieved near-complete esterification in the presence of an equimolar excess of oleic acid. Of additional interest is the finding that the addition of n-hexane markedly enhanced the esterification activities on all the medium- and long-chain saturated fatty acids used. Based on these findings, we attempted to synthesize stigmasterol stearate as a food additive to lower cholesterol levels in blood plasma, and found that the enzyme catalyzed effective synthesis of the ester without the need of dehydration during the reaction, indicating the potential utility of the enzyme in the food industry.

Topics: Anticholesteremic Agents; Biocatalysis; Cholesterol; Cholesterol Esters; Esterification; Fatty Acids; Fatty Acids, Volatile; Food Additives; Food Industry; Fungal Proteins; Hexanes; Hydrolysis; Molecular Structure; Oleic Acid; Oleic Acids; Phytosterols; Stearates; Sterol Esterase; Stigmasterol; Substrate Specificity; Trichoderma; Triolein; Water