In recent years, considerable attention has been directed to the site of origin, pathways of biosynthesis, metabolism, and excretory routes of unusual bile acids in human, particulaly for patients with hepatobiliary disease and newborn infants and fetus. In addition to five common bile acids (cholic, chenodeoxycholic, deoxycholic, ursodeoxycholic, and lithocholic acids), patients with hepatobiliary disease and newborn infants and fetus excrete a number of unusual bile acids in human biological fluids (bile, serum, urine, feces, and meconium). The unusual bile acids include the stereoisomers of the common bile acids, bile acids having various functional groups at different positions or in greater number than found in the common bile acids, and “short-chain” and “long-chain” bile acids. In this review, we compiled a list of the unusual bile acids hitherto reported in literatures and give an outline of procedures for their syntheses.

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飽和及び不飽和トリグリセリドの熱酸化中に起こるBHAの酸化的二量化に及ぼすリン脂質の影響を調べた。
BHAとリン脂質を加えたトリラウリンまたはトリリノレインを150℃, 10h空気酸化し,反応混合物中のBHA単量体と二量体をHPLCで定量した。
トリウラリン中においては,BHA単量体からジフェニルエーテル型二量体の生成が,リン脂質の添加によって強く抑制される。ホスファチジルエタノールアミンとホスファチジルコリンの影響の程度はほとんど同じであった。トリリノレイン中においては,リン脂質の添加によって,BHA単量体の安定性が著しく向上し,二量体の生成量が減少した。しかし,単量体と二量体の合計はあまり変わらなかった。これらのことから,リン脂質はBHAの酸化の初期段階を阻害していることが明らかとなった。トリオクチルアミンとリン酸トリブチルは酸化的二量化をわずかに抑制しただけであった。故にリン脂質によるBHAの酸化的二量化の抑制は,その分子中のリン酸エステル結合とアミングループの単なる協同作用ではないと考えられる。トリラウリンとトリリノレインの混合物(4:1)中におけるBHAの酸化的二量化に対するホスファチジルエタノールアミンの効果は,トリリノレイン単独中における場合と本質的に同様であった。

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脂質過酸化物のモデルとしてマロンアルデヒド,アルケナール,アルカジエナール,有機ヒドロペルオキシドの混合物のチオバルビツール酸(TBA)反応を4%酢酸中100℃, 20minの条件で行った。アルケナール,アルカジエナールからの赤色色素の生成は他の成分の存在により増強された。すなわち,アルケナールとアルカジエナールの混合や,2種のアルカジエナールの混合は相乗的に赤色色素の生成を増強し,また有機ヒドロペルオキシドの添加は,これらアルデヒドの赤色色素の生成を増強した。これらアルデヒドとTBAの1:1付加中間体がヒドロペルオキシドにより効率よく赤色色素になることが分かった。混合物のTBA反応における赤色色素の量は,マロンアルデヒド量をはるかに上まわるものであった。
以上の結果から,過酸化脂質のTBA反応における赤色色素の生成は,これら成分の相乗効果の寄与が大きいものと考えられる。

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The metabolism of lipids in the intestines was studied in vitro on their surface. Interfacial tension between lipids and water is depressed by adsorption of bile salts at the lipid-water interface. During triglyceride hydrolysis, the fraction of monoglyceride at this interface increases, leading to additional depression of interfacial tension and the formation of a fine lipid dispersion. The interfacial tension of lipid-water is minimum at optimum HLB (hydrophile lipophile balance) of mixed emulsifiers. With further hydrolysis, the monoglyceride fraction at the interface becomes larger, leading in turn to greater interfacial tension. Fine emulsion droplets produced on decreasing the interfacial tension to 0.50.3mN·m^-1, may be adsorbed on the intestinal wall when the HLB of the adsorbed amphiphile layer becomes lipophilic. This is because an amphiphile aggregate disperses water when it is hydrophilic, but forms an amphiphile phase when the hydrophile lipophile property is balanced or lipophilic. After absorption of emulsion droplets, triglyceride may form by esterification of glycerides. Thus, the HLB of mixed amphiphiles may become hydrophilic, and bile salts may dissolve into the blood and recirculate.

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The amino groups of lipase-P (Pseudomonas sp. lipase from Amano Pharmaceutical Ltd.) were modified with alkenyl succinic anhydride (ASA) that is used as a reactive sizing agent for paper making in industry. It was possible to N-acylate the amino groups smoothly up to 50% modification with little inactivation of the enzyme, using emulsified tetradecenyl succinic anhydride at 37°C, pH 7.5.
Ester-synthesis activity of the enzymes was estimated by using oleic acid and oleyl alcohol as substrates in cyclohexane. The enzymes were suspended in the substrate solution in powder form or in immobilized enzyme form (immobilized on celite and macroporous ion exchange resin). Both enzymes resulted in higher ester-synthesis activity. The initial ester-synthesis rate was 8.4 times that of either enzyme in its native form.

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The influence of cultural conditions, especially glucose concentration and C/N ratio, in a high concentration sugar medium on cell growth and lipid accumulation of Mortierella isabellina IFO 7884 fungus was investigated. M. isabellina was capable of growing in over a 200g/L glucose medium with little effect on cell growth. The high concentration of sugar in the medium accelerated lipid accumulation. The content of lipid cultivated in a high concentration sugar medium exceeded that in a low concentration sugar medium at the same C/N ratio. Maximum dry cell and total lipid weights of 156.4 and 83.1g/L were observed for a 390g/L glucose medium (C/N ratio=20). The highest lipid productivity, however, was found to be 0.69g/Lh for a 270g/L glucose medium (C/N ratio=20).

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Fatty acid compositions and physical characteristics of shortening were determined for 25 brands of products: for bread, whipped cream and frozen dessert, 5 brands each; 5 fluid brands; for cake; 4, and for pie crust, 1.
The investigation was conducted essentially the same as in the preceeding study on bakery margarines. [YUKAGAKU, in contribution]
1) Results of fatty acid analyses indicated the main material oil or fat to be a vegetable liquid oil in all brads of liquid shortening, a laurin oil in 2 types for frozen dessert and palm oil in the others for frozen dessert. Hardened marine oils were found to blend in 10 other types, as evident from the relatively high levels of long chain fatty acids with 20 or more carbon.
Trans-isomers of unsaturated fatty acids were detected in only a very few samples of fluid shortening and frozen dessert, but in all other types. Their levels averaged 11.4% for t-18:1, 3.8% for t-20:1 and 2.8% for t-22:1.
2) According to the SFC and hardness index curves, the frozen desserts, particularly those containing mainly laurin oil, tended to be harder than other solid products in a lower temperature region than 15°C, but they readily softened in a higher temperature region.
The SFC curve for fluid products indicated solid fat components to be comprised only of the emulsifiers added.
3) The hardness index was correlated to SFC for the shortening. The total % of unsaturated fatty acids, except trans-isomers, was also correlated to SFC at 20°C for all the products, and if products comprised mainly of laurin oil be not considered, the correlation was even better. However, no correlation was found between the total % and hardness index at 20°C for the shortening, even without this consideration.

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