Sterol metabolism. VII. Autoxidation of cholesterol via hydroperoxide intermediates
About: This article is published in Journal of Organic Chemistry.The article was published on 1970-08-01. It has received 101 citations till now. The article focuses on the topics: Autoxidation.
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TL;DR: The ability of oxygenated sterols to inhibit sterol synthesis in cultured cells and the ineffectiveness of cholesterol under the same conditions suggest that feedback regulation of sterol biosynthesis may be brought about by an oxygenated steroid rather than by cholesterol.
Abstract: A group of oxygenated sterols has been identified as potent and specific inhibitors of sterol biosynthesis. The ability of these compounds to inhibit sterol synthesis in cultured cells and the ineffectiveness of cholesterol under the same conditions suggest that feedback regulation of sterol biosynthesis may be brought about by an oxygenated sterol rather than by cholesterol. The nature of the regulatory sterol may vary in different cells with their specific requirements for cholesterol as a structural component or as a precursor of other steroid products. The use of oxygenated sterols to block sterol synthesis in cultured cells provides new information regarding the role of sterol in cell membrane structure and function. For example, de novo sterol synthesis is required for DNA synthesis and cell division by some cultured cells. Studies with cultured cells, and with rats and mice in vivo, suggest that oxygenated sterols could be of value in the treatment of several important human diseases.
545 citations
TL;DR: The observation of a smectic liquid crystalline phase for hydrated cholesterol correlates with its high surface activity and helps to explain its ability to exist in high concentrations in biological membranes.
217 citations
TL;DR: High levels of DNase I were found in digestive tissues, such as the parotid and submaxillary salivary glands and the lining of the small intestine, andreciable levels were present in the lymph node, kidney, heart, prostate gland, and seminal vesicle.
149 citations
TL;DR: Support for the involvement of singlet excited oxygen is obtained from azide inhibition and the formation of the specific singlet oxygen product with cholesterol in the case of the manganese complex.
Abstract: — Sulfonated phthalocyanine and a series of its metal chelates in combination with red light irradiation led to the degradation of L-tryptophan in oxygenated aqueous solution. The photoproducts and the rate of transformation of L-tryptophan are compared with hematoporphyrin and rose bengal sensitized photooxidation. In all cases the primary photoproducts are characterized as cis and trans-3a-hydroperoxy-l,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylic acid. Support for the involvement of singlet excited oxygen is obtained from azide inhibition and the formation of the specific singlet oxygen product with cholesterol. We observed the contribution of another pathway in the case of the manganese complex.
140 citations
TL;DR: A specific and sensitive means of detection of sterol hydroperoxides on irrigated thin-layer chromatoplates using N,N-dimethyl-p-phenylenediamine dihydrochloride has been developed and autoxidation of cholesterol in the solid state, in the irradiated solidState, in colloidal dispersion, and in aerated solution is shown.
128 citations