From Big Medical Encyclopedia

SPHINGOSINES — the highest aliphatic, usually unsaturated amino alcohols, eurysynusic in animal and vegetable organisms, are found hl. obr. as a part of sphingolipids. Villages have anticoagulating action, they inhibit transformation prothrombin (see) in thrombin (see). There are data on sharp increase in content of sphingosine at hemophilia.

The most important representative S. is 4-sfingenin (sphingosine, D-эритро-1,3-диокси-2-амино-4-транс-октадецен), CH 3 (CH 2 ) 12 CH=CHCH(OH)CH(NH 2 ) CH 2 OH, colourless crystal substance about a pier. t°pl 81,5 — 83 ° is powerful (weighing) 299,5 (from ether). Sphingosine is alcohol-soluble, ether, acetone, petroleum ether and is water-insoluble, has properties of the basis. Sphingosine is for the first time found by L. J. W. Thudi-chum in 1901 in structure cerebrosides (see) and sphingomyelins (see).

Sphingosine and its analogs (them more than 60 are known) are eurysynusic in membranes vegetable and zooblasts as a part of sphingolipids (see). The analog of sphingosine — dihydrosphingosine (sfinganin) by SN is extended in tissues of animals 3 (CH 2 ) 14 CH(OH)CH(NH 2 ) CH 2 IT. In sphingomyelin of a brain along with sphingosine polyunsaturated dihydrosphingosines are found. As a part of phytoglycolipids of vegetable fabrics, including seeds of plants, the SN phytosphingosine containing three hydroxylic groups is found 3 (CH 2 ) 13 CH(OH)CH(OH)CH(NH 2 ) CH 2

Synthesis of sphingosine at animals and the person begins OH with the condensation of a palmytoil-Co and L-serine catalyzed by piridoksalzavi-simy enzyme serine-palmitoyl-transferase (KF 2. 3. 1. 50). Formed at this Z-(Siberian salmon) oxo - D - dihydrosphingosine (3-digidrosfinganin) in reaction with NADF-N turns into dihydrosphingosine (D-sfinganin), reaction is catalyzed by enzyme sfinganin-reductase (KF 1. 1. 1. 102). Sphingosine is formed at dehydrogenation of digidro-sphingosine in reaction with a yellow enzyme.

In tissues of animals and the person (kidneys, a liver, a spleen, embryonal fabrics, etc.), except sphingolipids, it is revealed derivative sphingosine — sfingozinfosforilkholin, and also N-acylderivatives of sphingosine — the ceramides representing intermediate products of biosynthesis of sphingolipids. A metabolite of cerebrosides is psikhozin — galaktozilsfingozin, formed as a result of reaction between sphingosine and uridine-diphosphate (UDF) the galactose catalyzed УДФгалактоза-сфингозин-p-галактозилтрансферазой (KF 2. 4. 1. 23) microsomes of a brain. Sphingosine and dihydrosphingosine can directly react with ATP with formation of sfingenin-1-phosphate and sfinganin-1 - phosphate respectively, to-rye then are split with formation of a palmitaldegid and ethano-lamin-1-phosphate. The last is a source of sincaline (see) and a fosfati-diletanolamina in a brain.

For quantitative definition of sphingosine it is allocated in the form of 2,4-difenilproizvodny and define formed after oxidation of sphingosine iodic to - that formaldehyde or kolorimetrirut the painted complex of sphingosine with methyl ethyl acetate, orange after its extraction.

Bibliography: See bibliogr. to St. Sphingolipids .

N. V. Gulyaeva.