Partitioning of predominant lipophilic bioactives (squalene, α-tocopherol and β-sitosterol) during olive oil processing

The partitioning of predominant lipophilic olive bioactives (squalene, β-sitosterol and α-tocopherol) in olive oil processing was studied for the first time using common integrated olive milling plant. 7% of the oil and 5% of the squalene present in the olives was lost in the last pomace. β-sitosterol and α-tocopherol, which are mainly concentrated in the seed of the olive fruit, was recovered in virgin olive oil to a lesser extent (66%, 67%) while 10% were lost in last pomace. Thus, the loss of β-sitosterol and α-tocopherol was higher than that of squalene and oil, due to nonrecovered bound forms. 19% of the α-tocopherol and 21% of the β-sitosterol loss was unaccounted for, which can be attributed to degradation of α-tocopherol and incomplete recovery of sterols from the olive and pomace matrices. This study provides a basis for process development studies.     

Composition of organic and conventionally produced sunflower seed oil

The aim of the present study was to highlight the main differences between seed oils produced from conventionally cultivated crops and organically cultivated ones and processed using mild extraction procedures. The composition and the nutritional and health aspects of both types of sunflower seed oils were compared and were analytically tested to determine the macroscopic differences in proximate composition, the main differences in the minor components, the main quality parameters, the in vitro antioxidant activity, and the presence of trans-ethylene steroisomers in FA. No significant trends were found in the oil samples for TAG and FA composition, but remarkable differences were found in the composition of minor components and in the main chemical and analytical quality properties. The organically grown samples had a higher total antioxidant activity compared with the conventional samples. Trans FA were found only in the conventional oils.     

玉米须脂溶性化学成分的研究

从吉林省吉林地区产玉米的花柱和柱头中,分别经石油醚和乙醇提取、柱层析粗分、制备性薄层板细分、混合溶剂重结晶得到两个化合物,通过高效薄层、红外光谱和核磁共振等分别确定为亚油酸(Ⅰ)和β-谷甾醇(Ⅱ),其中亚油酸(Ⅰ)是在玉米须中首次分离的化合物.     

Effect of different initiators on temperature-sensitive monolithic columns and application in online enrichment of β-sitosterol

Three temperature-sensitive monolithic columns were prepared by atom transfer radical polymerization and oxidation–reduction method using the initiator systems of CCl₄/FeCl₂, BPO/DMA, and APS/TEMED, respectively. The three monoliths were characterized by scanning electron microscopy, nitrogen adsorption, and thermogravimetric analysis. The obtained monolithic columns were used as on-line solid phase extraction sorbent coupled with high-performance liquid chromatography for the enrichment of β-sitosterol. By comparing some influencing factors on the adsorption, the optimum temperature-sensitive monolithic column which was initiated by CCl₄/FeCl₂ was selected for enrichment of β-sitosterol from plant oil. The maximum adsorption capacity of the monolith for β-sitosterol was 10.0031 mg/g. The limit of detection and limit of quantitation were 0.039 and 0.13 mg/mL, respectively. The recovery was in the range of 90.21–98.26%. The results showed that the monolith had better selectivity for β-sitosterol and could be used for enrichment of β-sitosterol in food samples. © 2019 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019 , 136, 47683.     

Phytosterols in Seaweeds: An Overview on Biosynthesis to Biomedical Applications

Seaweed extracts are considered effective therapeutic alternatives to synthetic anticancer, antioxidant, and antimicrobial agents, owing to their availability, low cost, greater efficacy, eco-friendliness, and non-toxic nature. Since the bioactive constituents of seaweed, in particular, phytosterols, possess plenty of medicinal benefits over other conventional pharmaceutical agents, they have been extensively evaluated for many years. Fortunately, recent advances in phytosterol-based research have begun to unravel the evidence concerning these important processes and to endow the field with the understanding and identification of the potential contributions of seaweed-steroidal molecules that can be used as chemotherapeutic drugs. Despite the myriad of research interests in phytosterols, there is an immense need to fill the void with an up-to-date literature survey elucidating their biosynthesis, pharmacological effects, and other biomedical applications. Hence, in the present review, we summarize studies dealing with several types of seaweed to provide a comprehensive overview of the structural determination of several phytosterol molecules, their properties, biosynthetic pathways, and mechanisms of action, along with their health benefits, which could significantly contribute to the development of novel drugs and functional foods.     

Genotype and growing location effects on phytosterols in canola oil

There is little information available about phytosterols in canola (Brassica napa L.) oil and the effects of genotype and growing locations from Virginia and the mid-Atlantic region of the United States, a potential area for the establishment of domestic production to provide edible oil. Our objectives were to characterize the phytosterols, phospholipids, unsaponifiable matter, and FA in oil from Virginia-grown canola. Among 11 canola genotypes grown at two locations during 1995–1996 significant variations existed for oil content and FA profiles, but not for contents of phospholipids, unsaponifiable matter, total phytosterols, campesterol, stigmasterol, and β-sitosterol, Total phytosterol content in the oil of Virginia-grown canola varied from 0.7 to 0.9% with a mean of 0.8%. This concentration compared favorably with oil from Canadian canola, which typically contains 0.5 to 1.1% total phytosterols. The mean contents of brassicasterol, campesterol, stigmasterol, β-sitosterol, Δ⁵-avenasterol, and Δ⁷-stigmatenol as percentages of total phytosterols in Virginia-grown canola were: 9.7, 32.0, 0.6, 49.3, 4.99, and 3.5%, respectively. Growing location did not affect phytosterols in Virginia-grown canola oil but had significant effects on contents of phospholipids, and saturated (myristic, stearic, and arachidic) and unsaturated (palmitoleic, linoleic, linolenic, eicosenoic, and erucic) FA.     

Purification of Commercially Available β-Sitosterol via Chemical Synthesis

β-Sitosterol, a plant sterol, is found to be useful in the nutraceutical and pharmaceutical industries, but is also frequently employed in biological research. In addition to stigmasterol, phytosterols are available as mixtures, and it is challenging to obtain highly pure β-sitosterol in larger quantities. Two methods for the purification of β-sitosterol from commercially available phytosterols are presented. Both methods are based on increasing the polarity by either epoxidation or dihydroxylation reactions with the Δ^5–6 double bond of the sterol. The synthesis methods and purification are chosen to be simple with inexpensive and easily obtained reagents and equipment in the laboratory. The purifications described afford β-sitosterol in gram quantities with high purity (>95%) at 37–39% and 32% yields for epoxidation and dihydroxylation reactions, respectively. The highly pure β-sitosterol is only available in small quantities, which makes it expensive. The presented methods can be used for obtaining the pure β-sitosterol in large scale using relatively simple organic chemistry and preparative chromatography. The use of the method may significantly increase the quantity available, which causes a reduction in price and, consequently, increases the number of research and applications available with the use of β-sitosterol.     

Bio-guided fractionation of the antimutagenic activity of methanolic extract from the fruit of Randia echinocarpa (Sessé et Mociño) against 1-nitropyrene

Randia echinocarpa is a native plant from Mexico that produces an edible fruit with several ethnopharmacological uses (e.g. cancer, kidney ailments, and diabetes). Extracts of this fruit have shown antimutagenic activity. In this report, a methanolic extract of R. echinocarpa and a bio-guided chromatographic strategy were used to obtain an hexanic fraction (HF) with strong antimutagenic activity (microsuspension assay with Salmonella typhimurium YG1024) using 1-nitropyrene as mutagen (1-NP, 50 and 100 ng/tube). The HF (500 ng/tube) showed the highest inhibition percentage of mutagenic activity (PI) (75%, 1-NP 50 ng/tube; 84%, 1-NP 100 ng/tube). HF chromatography with silica produced HF₁ which was further separated to produce the fractions with the highest antimutagenic activities (HF_1–1 and HF_1–2, PI ≥ 60%). These fractions were chemically characterized by chromatography and gas chromatography–mass spectrometry; among the main components of HF, HF_1–1 and HF_1–2 were registered linoleic acid, palmitic acid and β-sitosterol, which could be responsible for the antimutagenic activity of R. echinocarpa fruit. The samples evaluated were neither toxic nor mutagenic. Randia echinocarpa is an underutilized plant and its fruit has been used traditionally as food/medicine; fruit consumption could provide human health benefits and it has potential to be exploited under conditions of ecological sustainability.     

植物甾醇结晶分离工艺条件的研究

采用溶剂结晶分离工艺从混合植物甾醇中分离豆甾醇和β-谷甾醇,选择了二氯乙烷和正庚烷的二元共沸物（体积比63∶37）作为溶剂,综合工业生产中要求的豆甾醇的纯度和收率,确定了较为合理的结晶分离工艺条件,即溶剂比为1∶4,结晶温度为30℃,结晶时间为2～4 h。     

Antioxidant and antimicrobial activities of the methanol extracts from pummelo (Citrus grandis Osbeck) fruit albedo tissues

The present study was conducted to evaluate the antioxidant and antimicrobial properties of methanol (100 and 80% aqueous) extracts of pummelo fruits albedo (Citrus grandis Osbeck). The antioxidant and antibacterial activity for crude extracts and isolated compounds were evaluated using free radical 1,1-diphenyl-2-picrylhydrazyl (DPPH) and Paper disc diffusion method. A 100% Methanol (MeOH) extract was steeped in water at different pH levels and partitioned with ethyl acetate (EtOAc) to give basic, acidic, neutral, and phenolic fractions. The neutral extract was found to possess maximum antioxidant and antibacterial activity. Thereafter, neutral extract was carried out on a silica gel column and eluted with hexane:EtOAc:acetone and preparative TLC (PTLC) to give oil buntan compound, linoleic acid methyl ester, β-sitosterol, sigmasterol, limonin, nomilin and meranzin hydrate were isolated. While, 80% MeOH extract was fractionated also using a silica gel column and PTLC to give isomeranzin hydrate, p-coumaric acid and caffeic acid compound. The extract concentration providing 50% inhibition (IC₅₀) was as follows; oil buntan compound 95 μg/mL, caffeic acid 45 μg/mL, p-coumaric acid 105 μg/mL, limonin + nomilin (mixture) 135 μg/mL was lower than that of synthetic antioxidant butylated hydroxyanisole (BHA) 40 μg/mL. The inhibitory zone (mm) of bacteria tested was 2.9–4.1 mm caffeic acid and 11.6–15.1 mm p-coumaric acid.