• Journal of the Korean Applied Science and Technology
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• v.40 no.5
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• pp.1163-1175
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• 2023

Cholesterol is prone to oxidation, which results in the formation of cholesterol oxidation products (COPs). This occurs because it is a monounsaturated lipid with a double bond on C-5 position. Cholesterol in foods is mostly non-enzymatically oxidized by reactive oxygen species (ROS)-mediated auto-oxidative reaction. The COPs are found in many common foods of animal-origin and are formed during their manufacture process. The formation of COPs is mainly related to the temperature and the heating time the food is processed, storage condition, light exposure and level of activator present such as free radical. The level of COPs in processed foods could reach up to 1-10 % of the total cholesterol depending on the foods. The most predominant COPs in foods including meat, eggs, dairy products as well as other foods of animal origin were 7-ketocholesterol, 7 α-hydroxycholesterol (7α-OH), 7β-hydroxycholesterol (7β-OH), 5,6α-epoxycholesterol (5,6α-EP), 5,6β-epoxycholesterol (5,6β-EP), 25-hydoxycholesterol (25-OH), 20-hydroxycholesterol (20-OH) and cholestanetriol (triol). They are mainly formed non-enzymatically by cholesterol autoxidation. The COPs are known to be potentially more hazardous to human health than pure cholesterol. The procedure to block cholesterol oxidation in foods should be similar to that of lipid oxidation inhibition since both cholesterol and lipid oxidation go through the same free radical mechanism. The formation of COPs in foods can be stopped by decreasing heating time and temperature, controlling storage condition as well as adding antioxidants into food products. This review aims to present, discuss and respond to articles and studies published on the topics of the formation and inhibition of COPs in foods and key factors that might affect cholesterol oxidation. This review may be used as a basic guide to control the formation of COPs in the food industry.

• IMMUNE NETWORK
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• v.23 no.5
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• pp.40.1-40.14
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• 2023

Glucocorticoids suppress the vascular inflammation that occurs under hypercholesterolemia, as demonstrated in an animal model fed a high-cholesterol diet. However, the molecular mechanisms underlying these beneficial effects remain poorly understood. Because cholesterol is oxidized to form cholesterol oxides (oxysterols) that are capable of inducing inflammation, we investigated whether glucocorticoids affect the immune responses evoked by 7α-hydroxycholesterol (7αOHChol). The treatment of human THP-1 monocytic cells with dexamethasone (Dex) and prednisolone (Pdn) downregulated the expression of pattern recognition receptors (PRRs), such as TLR6 and CD14, and diminished 7αOHChol-enhanced response to FSL-1, a TLR2/6 ligand, and lipopolysaccharide, which interacts with CD14 to initiate immune responses, as determined by the reduced secretion of IL-23 and CCL2, respectively. Glucocorticoids weakened the 7αOHChol-induced production of CCL2 and CCR5 ligands, which was accompanied by decreased migration of monocytic cells and CCR5-expressing Jurkat T cells. Treatment with Dex or Pdn also reduced the phosphorylation of the Akt-1 Src, ERK1/2, and p65 subunits. These results indicate that both Dex and Pdn impair the expression of PRRs and their downstream products, chemokine production, and phosphorylation of signaling molecules. Collectively, glucocorticoids suppress the innate immune response and activation of monocytic cells to an inflammatory phenotype enhanced or induced by 7αOHChol, which may contribute to the anti-inflammatory effects in hypercholesterolemic conditions.

• Journal of Food Hygiene and Safety
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• v.23 no.1
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• pp.1-5
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• 2008

The inhibition of cholesterol autoxidation by commercial ${\gamma}$-Oryzanol (0, 50, 100, and 300 ppm) was studied in an aqueous model system for 20 h at pH 5.5 and $80^{\circ}C$. The inhibition effectiveness of the commercial ${\gamma}$-Oryzanol was followed by the retention of cholesterol and the formation of C-7 oxidized cholesterol derivatives (OCDs). Changes in the amount of ${\gamma}$-Oryzanol in the aqueous system were determined during cholesterol autoxidation. A method to detect the levels of 7-ketocholesterol, $7{\alpha}$-hydroxycholesterol and $7{\beta}$-hydroxycholesterol in an aqueous model system with ${\gamma}$-Oryzanol was developed by using the hexane-ethyl acetate extraction system and high-performance liquid chromatography. Results showed that the levels of C-7 OCDs in an aqueous dispersion containing 300 ppm of ${\gamma}$-Oryzanol were not significantly (p>0.05) increased, when compared to other treatments (0, 50, and 100 ppm), during the accelerated cholesterol oxidation.

• Journal of Life Science
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• v.16 no.6
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• pp.1029-1035
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• 2006

The study was designed to investigate the influence of feeding Eosungcho(houttutnia cordata Thunb) on the meat quality of porks. Experimental groups were divided into control group(C), 5%(T1) and 10%(T2) Eosungcho powder feeding group, and than administered for 12 weeks. And then pork's loins were storaged at $4^{\circ}C$, for 23 days after vaccum packed. TBARS was increased(P<0.05) during storage days in all samples, while it's contents were lower Eosungcho feding groups than control group. Total cholesterol contents of pork's loin, were $48.9{\pm}0.2\;mg/100\;g$ in control group, $39.1{\pm}0.2\;mg/100\;g$ in T1 group and $37.8{\pm}0.3\;mg/100\;g$ in T2 group. 4 kinds of cholesterol oxides($7{\beta}-hydroxycholesterol$, 19-hydroxycholesterol, ${\alpha}-$ and ${\beta}-epoxide$) detected in pork's loin. Cholesterol oxides concentration of pork's loin was increased during storage and lowest in T2 group.

• The Korean Journal of Food And Nutrition
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• v.14 no.6
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• pp.573-578
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• 2001

Cholesterol oxidation products(COPs) such as 7-ketocholesterol, 7 ${\alpha}$, 7 ${\beta}$-hydroxycholesterol and 25-hydroxycholesterol were analyzed for ensuring the safety of squid during its drying and cooking. In addition. changes of malonaldehyde in squid during its drying and cooking were also investigated. Cholesterol was detected 636.4m9/1009 in fresh sample, which was decreased during its drying and cholesterol contents in dried sample were 468.9mg/100g, 486.8mg/100g, respectively, while COPs contents of sun and hot air dried samples increased about 6.2 times more than those contents of fresh sample. Regardless of cooking methods, the contents of COPs in dried products increased after cooking. Especially, those contents were determined 127.3 mg/g in sun dried samples were cooked by microwave oven. The malonaldehyde contents of dried products increased after cooking, its contents in cooked samples by an microwave oven after sun dried were about 4.3 times more than in control products. In general, a small quantity of COPs were formed in dried samples which were cooked by a steam.

• Bulletin of the Korean Chemical Society
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• v.34 no.9
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• pp.2787-2794
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• 2013

Cholesterol and cholesterol oxidation products (COPs) may accumulate in foods of animal origin during processing or storage. An effective and sensitive analytical method was developed by increasing the UV absorption of compounds through derivatization by attaching a chromophore to the functional groups of cholesterols (cholesterol, 20-hydroxycholesterol, 7-ketocholesterol, cholestane-$3{\beta}$-$5{\alpha}$-$6{\beta}$-triol, 25-hydroxycholesterol, and $5,6{\alpha}$-epoxycholesterol). The influences of the reaction time, volume of reaction solvent, amounts of derivatizing reagent, and extraction solvents were investigated, as they may influence the reaction and extraction yield. The derivatized COPs were analyzed simultaneously on a C18 column (2.1 mm i.d. ${\times}$ 100 mm length, $3.5{\mu}m$ particle size) using a gradient elution with water and acetonitrile. The derivatized COPs showed increased sensitivity and selectivity in HPLC/UV-Vis. The LOD and LOQ were in the concentration ranges of 0.018-0.55 mg/kg and 0.059-1.84 mg/kg from the powdered milk. And the accuracy and precision were 78.1-116.7% and 1.1-9.9%, respectively.

• Environmental Mutagens and Carcinogens
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• v.25 no.2
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• pp.76-81
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• 2005

25-Hydroxycholesterol (cholest-5-ene-3, 25-diol, 25-OHC) showed the cytotoxicity on HeLa human cervix and NCI-H460 human lung cancer cells, $0.5{\mu}M\;of\;50\%$ inhibitory concentration. We studied 25-OHC as the possibility of radiation sensitizer. The combination effect of 25-OHC and y-irradiation measured using flow cytometer with propidium iodide stained cells. The combined treatment of 25-OHC and $\gamma-irradiation$ did not show significant enhancing effects on Hela and NCI-H460 cells.

• Korean Journal of Food Science and Technology
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• v.31 no.1
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• pp.74-82
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• 1999

Beef, pork and chicken meat that retailed in market were used as experimental samples. Some samples in raw state were packaged with PVDC as aerobic and vacuum condition. The other samples were cooked until internal temperature arrived at $70^{\circ}C$ using electric oven and then packaged immediately in the same way of raw samples. After these samples were irradiated by electron beam (0, 1, 2 kGy), irradiated samples were stored in refrigerator $(2{\sim}4^{\circ}C)$. Identification and quantification of cholesterol oxides were analysed at 0, 7, 14 days. The results were following. The results indicated that raw-vacuum packaged lower detected than that of other treatments. In raw-vacuum packaged, the amounts of $7{\beta}-hydroxycholesterol$ were detected slightly $(below\;0.5\;{\mu}ug/g)$ during storage, and 7-ketocholesterol were detected during every stored time and amounts of this detection were $8.02{\sim}101.30\;{\mu}g/g$. In cooked-aerobic packaged, total amounts of detection were higher than that of other treatments, total amounts of cholesterol oxides were detected about $51.18{\sim}155.90\;{\mu}g/g$ during storage. In all results, pork and chicken samples were similar to the results of beef samples. In all results, total amounts of cholesterol oxides increased significantly as irradiation dose and storage time increased (P<0.05).

• Journal of Life Science
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• v.32 no.3
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• pp.256-262
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• 2022

Oxysterols are oxygenated metabolites of cholesterol generated by serial enzymatic reactions during bile acid synthesis. Similar to cholesterol, oxysterols move rapidly to the intracellular region and modulate various cellular processes, such as immune cell responses, lipid metabolism, and cholesterol homeostasis. Different nuclear transcription factors, such as glucocorticoid, estrogen, and liver X receptors, can be modulated by oxysterols in multiple tissues. The most abundant oxysterol, 27-hydroxycholesterol (27-OHC), is a well-known selective modulator that can either activate or suppress estrogen receptor activity in a tissue-specific manner. The contribution of 27-OHC in atherosclerosis development is apparent because a large amount of it is found in atherosclerotic plaques, accelerating the transformation of macrophages into foam cells that uptake extracellular modified lipids. According to previous studies, however, there are opposing opinions about how 27-OHC affects lipid and cholesterol metabolism in metabolic organs, including the liver and adipose tissue. In particular, the effects of 27-OHC on lipid metabolism are entirely different between in vitro and in vivo conditions, suggesting that understanding the physiology of this oxysterol requires a sophisticated approach. This review summarizes the potential effects of 27-OHC in atherosclerosis and metabolic syndromes with a special discussion of its role in metabolic tissues.

• Proceedings of the PSK Conference
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• 2003.10b
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• pp.184.2-184.2
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• 2003

Many naturally occurring polyhydroxylated sterols and oxysterols exhibit potent biologic activities. The role of oxycholesterol including 2, 5(R)-2, 6-hydroxycholesterol is a potent inhibitor of cholesterol biosynthesis in vitro as it is an effective inhibitor of HMG-Coa reductase. Some new polyhydroxylated sterols were showed potent cytotoxicity to cancer cells. And it has also been chown to be an inhibitor of DNA synthesis, In order to synthesize the various oxy derivatives, we tried to positionselective and reagentselective epoxidation and reduction of cholesterol derivatives. (omitted)