• Title, Summary, Keyword: cholesterol oxide products

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The Effect of Salting Conditions on Formation of Cholesterol and Cholesterol Oxides During Gulbi Processing and Storage (염장조건이 굴비 가공 중 콜레스테롤 및 콜레스테롤 산화물 생성에 미치는 영향)

  • Kang, Min-Jung;Park, Sun-Young;Shin, Jung-Hye;Choi, Duk-Ju;Cho, Hyun-So;Lee, Soo-Jung;Sung, Nak-Ju
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.37 no.2
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    • pp.251-255
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    • 2008
  • Cholesterol and cholesterol oxide products (COPs) of Gulbi (Pseudosciaena manchurica) processed and stored at different salting times of 5 hours and 5 days were analyzed. The content of cholesterol was $133.4{\pm}5.20\;mg/100\;g$ in the fresh sample. Cholesterol content was decreased during salting and storage; its contents were $130.3{\pm}2.95\;mg/100\;g$ and $87.2{\pm}3.49\;mg/100\;g$ in 5 hours and 5 days salting samples, respectively. The content of 7-ketocholesterol in 5 hours and 5 days salting samples were $75.2{\pm}2.70\;{\mu}g/100\;g$ and $82.4{\pm}3.30\;{\mu}g/100\;g$. The 7-ketocholesterol content of salting sample for 5 hours had no significantly difference for 2 days sun drying, but it was dramatically increased during 5 days sun drying and then increased during storage days. $7{\alpha}-$ and $7{\beta}-hydroxycholesterol$ were not detected in fresh sample, but increased during Gulbi processing and storage. The $7{\alpha}-hydroxycholesterol$ was increased during Gulbi processing and storage and a higher level of $658.1{\pm}6.20\;{\mu}g/100\;g$ was detected in 5 hours salting sample than in 5 days salting sample after 21 days storage. The $7{\beta}-hydroxycholesterol$ also showed similar tendency with $7{\alpha}-hydroxycholesterol$; it was largely increased between 7 and 14 days storage in 5 days salting sample.

Effect on Endurance Improving of Mixture of the Extracts of Watermelon and Octacosanol (Octacosanol과 박과식물 추출물을 주성분으로 하는 혼합물의 지구력 증진 효과)

  • Lim, Hyun-Woo;Kim, Sung-Kyu;Lee, Min-Won
    • YAKHAK HOEJI
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    • v.49 no.6
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    • pp.465-470
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    • 2005
  • Octacosanol is known to enhance endurance activities, control cholesterol in body and improve the function of cardiopulmonary. Citrulline, which is main compound of watermelon, is known to improve angiectasia through stimulating production of nitric oxide. To improve endurance activity swimming test on rats was carried out using four samples such as 1$\%$ octacosanol, citrulline, the extracts of barks of watermelon and products, mixture of 1$\%$ octacosanol and the extracts of barks of watermelon (6 : 4). Biochemical assays on the liver and serum of tested rats were also performed using commercial analysis kits. In result, it was shown that swimming time of III group increased by 26$\%$ and that of V group was increased by 22$\%$ at the swimming test. As a result of biological assays on the liver and serum of tested rats it was possible to confirm stability of toxicity When compared with creatine kinase of control group (549.11$\pm$39.15 U/l) citrulline (644.11 $\pm$50.67 U/l) and products group (646.00$\pm$46.99 U/l) were largely increased. When compared with inorganic phosphate of control group (12.01$\pm$0.75 mg/이), citrulline (13.03$\pm$0.94 mg/dl) and products group (12.90$\pm$0.55 mg/dl) showed similar results. Also, when compared with lactic acid and glucose of control group (152.91 $\pm$ 13.45, 103.00$\pm$ 8.69 mg/dl), citrulline (125.53$\pm$15.54, 83.75$\pm$7.29 mg/dl) and products group (135.26$\pm$11.50, 78.57$\pm$9.79 mg/dl) were largely decreased. As these test results, it was determined that 1$\%$ octacosanol and extracts of barks of watermelon had some effect of improving endurance activity. Futhermore, it was thought that it could be used as source of functional food.

Effects of Electron-Beam Irradiation and Storage on Cholesterol Oxides Products of Beef Meat (전자선 조사와 저장기간이 우육의 콜레스테롤 산화물질에 미치는 영향)

  • Lee, Jeong-Ill;Min, Joong-Seok;Kim, Il-Suk;Park, Gu-Boo;Lee, Moo-Ha
    • Korean Journal of Food Science and Technology
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    • v.30 no.6
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    • pp.1312-1320
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    • 1998
  • Some commercial beef loins in raw state were packaged with PVDC as aerobic and vacuum condition. The other beef samples were cooked until core temperature arrived at $70^{\circ}C$ and then packaged immediately in the same way as the raw state. These samples were irradiated by electron beam (0, 1, 2 kGy), and then stored in refrigerator $(2{\sim}4^{\circ}C)$. Identity and quantity of cholesterol oxides were analysed at the 0, 7th, 14th day of storage. In the samples that were raw and packaged aerobically, $7{\alpha}-hydroxycholesterol,\;{\beta}-epoxide,\;7{\beta}-hydroxycholesterol$ and 7-ketocholesterol were detected over $0.5\;{\mu}g/g$. Cholestanetriol and${\alpha}-epoxide$ were detected at levels below $0.5\;{\mu}g/g$ during storage. In the samples that were raw and vacuum-packaged, $7{\alpha}-hydroxycholesterol$, 7-ketocholesterol and cholestanetriol were detected. In the samples that were cooked and packaged aerobically, cholestanetriol and ${\alpha}-epoxide$ were detected below $0.5\;{\mu}g/g$ during storage. $7{\alpha}-hydroxycholesterol,\;{\beta}-epoxide,\;7{\beta}-hydroxycholesterol$and 7-ketocholesterol were detected as $1.53{\sim}26.81,\;1.07{\sim}5.23,\;40.64{\sim}101.30\;and\;7.16{\sim}33.91\;{\mu}g/g$, respectively. In all results, total amounts of cholesterol oxide increased significantly as irradiation dose and storage time increased (P<0.05).

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Effects of Cooking Method and Temperature on the Lipid Oxidation of Electron-Beam Irradiated Hanwoo Steak. (가열방법 및 온도가 전자선 조사한 한우 steak의 지질산화에 미치는 영향)

  • Park T. S.;Shin T. S.;Lee J. I.;Park G. B.
    • Journal of Life Science
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    • v.15 no.5
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    • pp.840-846
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    • 2005
  • This study was carried out to investigate the effect of electron beam irradiation and cooking temperature on physico-chemical characteristics and lipid oxidation of beef. A total of six beef carcasses ($280\∼300 kg$) that were quality grade $1^{+}$(marbling score No.7, meat color No.4, maturity No.1, texture No.1) was purchased at the commercial slaughter house. The carcasses were transported and washed using high pressure water, and pasteulized with $ 50\% $ ethyl alcohol in the laboratory. After the carcasses were deboned and trimmed, loin and round were taken out to make steak (1.5cm thickness) or ground beef respectively. Samples were wrap or vacuum packaged and irradiated with 0, 3, 4.5, 6 and 7.5 kGy using electron-beam accelerator at Samsung Heavy Industries Ltd. Co. (in Taejun). Irradiated samples were cooked with different methods(electronic pan and gas oven) and temperatures ($ 60^{\circ}C, 70^{\circ}C and 80^{\circ}C$) and used to measure fatty acid composition, TBARS, cholesterol oxide products and panel test scores. The content of saturated fatty acids increased by increasing heating temperature in oven boiling steak (OBS) and pan boiling steak (PBS), and there was no difference by electron-beam irradiation. Both irradiated and non-irradiated treatment were high as the heating temperature increased in TBARS by heating temperature in PBS (p < 0.05) and the amount of Malonaldehyde (MA), standard of fat deterioration, was increased in OBS (p < 0.05). Non-irradiated and 3, 6 kGy treatment produced about 2 fold amount of MA at $ 60^{\circ}C $ compared with $ 80^{\circ}C $. In comparison with PBS, OBS produced much amount of MA and a bit different from non-irradiated treatment but did not show no tendency. As irradiation levels and heating temperature increased, the amount of cholesterol oxides products was increased and also pan-heating method, direct heating method, significantly increased the degree of oxidation compared with oven-heating method, indirect heating method (p < 0.05).

Sesquiterpenoids Bioconversion Analysis by Wood Rot Fungi

  • Lee, Su-Yeon;Ryu, Sun-Hwa;Choi, In-Gyu;Kim, Myungkil
    • 한국균학회소식:학술대회논문집
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    • pp.19-20
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    • 2016
  • Sesquiterpenoids are defined as $C_{15}$ compounds derived from farnesyl pyrophosphate (FPP), and their complex structures are found in the tissue of many diverse plants (Degenhardt et al. 2009). FPP's long chain length and additional double bond enables its conversion to a huge range of mono-, di-, and tri-cyclic structures. A number of cyclic sesquiterpenes with alcohol, aldehyde, and ketone derivatives have key biological and medicinal properties (Fraga 1999). Fungi, such as the wood-rotting Polyporus brumalis, are excellent sources of pharmaceutically interesting natural products such as sesquiterpenoids. In this study, we investigated the biosynthesis of P. brumalis sesquiterpenoids on modified medium. Fungal suspensions of 11 white rot species were inoculated in modified medium containing $C_6H_{12}O_6$, $C_4H_{12}N_2O_6$, $KH_2PO_4$, $MgSO_4$, and $CaCl_2$ for 20 days. Cultivation was stopped by solvent extraction via separation of the mycelium. The metabolites were identified as follows: propionic acid (1), mevalonic acid lactone (2), ${\beta}$-eudesmane (3), and ${\beta}$-eudesmol (4), respectively (Figure 1). The main peaks of ${\beta}$-eudesmane and ${\beta}$-eudesmol, which were indicative of sesquiterpene structures, were consistently detected for 5, 7, 12, and 15 days These results demonstrated the existence of terpene metabolism in the mycelium of P. brumalis. Polyporus spp. are known to generate flavor components such as methyl 2,4-dihydroxy-3,6-dimethyl benzoate; 2-hydroxy-4-methoxy-6-methyl benzoic acid; 3-hydroxy-5-methyl phenol; and 3-methoxy-2,5-dimethyl phenol in submerged cultures (Hoffmann and Esser 1978). Drimanes of sesquiterpenes were reported as metabolites from P. arcularius and shown to exhibit antimicrobial activity against Gram-positive bacteria such as Staphylococcus aureus (Fleck et al. 1996). The main metabolites of P. brumalis, ${\beta}$-Eudesmol and ${\beta}$-eudesmane, were categorized as eudesmane-type sesquiterpene structures. The eudesmane skeleton could be biosynthesized from FPP-derived IPP, and approximately 1,000 structures have been identified in plants as essential oils. The biosynthesis of eudesmol from P. brumalis may thus be an important tool for the production of useful natural compounds as presumed from its identified potent bioactivity in plants. Essential oils comprising eudesmane-type sesquiterpenoids have been previously and extensively researched (Wu et al. 2006). ${\beta}$-Eudesmol is a well-known and important eudesmane alcohol with an anticholinergic effect in the vascular endothelium (Tsuneki et al. 2005). Additionally, recent studies demonstrated that ${\beta}$-eudesmol acts as a channel blocker for nicotinic acetylcholine receptors at the neuromuscular junction, and it can inhibit angiogenesis in vitro and in vivo by blocking the mitogen-activated protein kinase (MAPK) signaling pathway (Seo et al. 2011). Variation of nutrients was conducted to determine an optimum condition for the biosynthesis of sesquiterpenes by P. brumalis. Genes encoding terpene synthases, which are crucial to the terpene synthesis pathway, generally respond to environmental factors such as pH, temperature, and available nutrients (Hoffmeister and Keller 2007, Yu and Keller 2005). Calvo et al. described the effect of major nutrients, carbon and nitrogen, on the synthesis of secondary metabolites (Calvo et al. 2002). P. brumalis did not prefer to synthesize sesquiterpenes under all growth conditions. Results of differences in metabolites observed in P. brumalis grown in PDB and modified medium highlighted the potential effect inorganic sources such as $C_4H_{12}N_2O_6$, $KH_2PO_4$, $MgSO_4$, and $CaCl_2$ on sesquiterpene synthesis. ${\beta}$-eudesmol was apparent during cultivation except for when P. brumalis was grown on $MgSO_4$-free medium. These results demonstrated that $MgSO_4$ can specifically control the biosynthesis of ${\beta}$-eudesmol. Magnesium has been reported as a cofactor that binds to sesquiterpene synthase (Agger et al. 2008). Specifically, the $Mg^{2+}$ ions bind to two conserved metal-binding motifs. These metal ions complex to the substrate pyrophosphate, thereby promoting the ionization of the leaving groups of FPP and resulting in the generation of a highly reactive allylic cation. Effect of magnesium source on the sesquiterpene biosynthesis was also identified via analysis of the concentration of total carbohydrates. Our current study offered further insight that fungal sesquiterpene biosynthesis can be controlled by nutrients. To profile the metabolites of P. brumalis, the cultures were extracted based on the growth curve. Despite metabolites produced during mycelia growth, there was difficulty in detecting significant changes in metabolite production, especially those at low concentrations. These compounds may be of interest in understanding their synthetic mechanisms in P. brumalis. The synthesis of terpene compounds began during the growth phase at day 9. Sesquiterpene synthesis occurred after growth was complete. At day 9, drimenol, farnesol, and mevalonic lactone (or mevalonic acid lactone) were identified. Mevalonic acid lactone is the precursor of the mevalonic pathway, and particularly, it is a precursor for a number of biologically important lipids, including cholesterol hormones (Buckley et al. 2002). Farnesol is the precursor of sesquiterpenoids. Drimenol compounds, bi-cyclic-sesquiterpene alcohols, can be synthesized from trans-trans farnesol via cyclization and rearrangement (Polovinka et al. 1994). They have also been identified in the basidiomycota Lentinus lepideus as secondary metabolites. After 12 days in the growth phase, ${\beta}$-elemene caryophyllene, ${\delta}$-cadiene, and eudesmane were detected with ${\beta}$-eudesmol. The data showed the synthesis of sesquiterpene hydrocarbons with bi-cyclic structures. These compounds can be synthesized from FPP by cyclization. Cyclic terpenoids are synthesized through the formation of a carbon skeleton from linear precursors by terpene cyclase, which is followed by chemical modification by oxidation, reduction, methylation, etc. Sesquiterpene cyclase is a key branch-point enzyme that catalyzes the complex intermolecular cyclization of the linear prenyl diphosphate into cyclic hydrocarbons (Toyomasu et al. 2007). After 20 days in stationary phase, the oxygenated structures eudesmol, elemol, and caryophyllene oxide were detected. Thus, after growth, sesquiterpenes were identified. Per these results, we showed that terpene metabolism in wood-rotting fungi occurs in the stationary phase. We also showed that such metabolism can be controlled by magnesium supplementation in the growth medium. In conclusion, we identified P. brumalis as a wood-rotting fungus that can produce sesquiterpenes. To mechanistically understand eudesmane-type sesquiterpene biosynthesis in P. brumalis, further research into the genes regulating the dynamics of such biosynthesis is warranted.

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