US3681412A - Glycol phosphatides and the preparation thereof from cephalin - Google Patents

Glycol phosphatides and the preparation thereof from cephalin Download PDF

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US3681412A
US3681412A US76231A US3681412DA US3681412A US 3681412 A US3681412 A US 3681412A US 76231 A US76231 A US 76231A US 3681412D A US3681412D A US 3681412DA US 3681412 A US3681412 A US 3681412A
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solution
cephalin
phosphatidyl
phosphatides
phosphatide
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Hans Betzing
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A Natterman und Cie GmbH
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A Natterman und Cie GmbH
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/10—Phosphatides, e.g. lecithin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl

Definitions

  • H -O--R2 wherein R and R, each are fatty acid groups of 10-24 carbon atoms, inclusive, X is a hydrogen atom or -COOl-l, which are useful as emulsifiers for intravenous fat-feeding, are produced by removing the amino group of colamine and serine phosphatides by treatment with aqueous nitrous acid under mild conditions followed by diazotization.
  • cephalin fractions when obtained from vegetable substance, contain substantially phosphatidyl colamine, in addition to lecithins. When produced from animal sources, they contain both phosphatidyl colamine and phosphatidyl serine. Thae cephalim exhibit, depending on the specific starting material, varying fatty acid residues generally containing -24 carbon atoms.
  • the cephalin fractions preferred simultaneously therapeutic purposes contain phosphatidyl colamines or phosphatidyl serines which have a high percentage of unsaturated. especially polyunsaturated, fatty acid residues. Due to the strong reactivity of the polyunsaturated fatty acids, the isolation thereof is not simple. They are usually obtained during the extraction of raw phosphatides with lower-alcohols.
  • cephalins and phosphatide fractions containing them serve, inter alia, as natural emulsifiers since they possess, in addition to the lipophilic fatty acid residues, the hydraphilic glycerophosphoric acid group and colamine or serine residues.
  • the emulsifying effect is relatively low, due to the fact that the free amino group is intramolecularly bound as an inner salt with the phosphoric acid group.
  • cephalin-containing phosphatide mixtures are also employed as drugs. However, they must be employed with caution as emulsifiers in intravenous fat-feedings because the cephalins as such are blood clotting activators. Furthermore, it was found that the cephalin-containing phosphatides heretofore employed for intravenous fat nourishment can evoke troublesome side effects, such as fever and chills. It has now been discovered, these side-effects are due primarily to the amino group of the cephalins.
  • US. Pat. No. 3,301,881 discloses a process wherein cephalin is entirely or partially acylated by treatment of aqueous phosphatide emulsions with organic acid anhydrides, whereby the primary amino group is converted into an acid amide.
  • the resulting phosphatides are more plastic and more readily dispersed in aqueous media.
  • novel phosphatidyl compounds having enhanced utility as emulsifiers, especially for intravenous fat-feeding can be produced in a simple manner from phosphatidyl colamines and phosphatidyl serines.
  • the amino group of phosphatidyl colamines and phosphatidyl serines is removed without splitting off the fatty acid groups or chemically altering the sensitive unsaturated or polyunsaturated fatty acid residues during this process, by treatment with nitrous acid followed by diazotization to produce novel glycol phosphatides which can be represented by the general formula wherein R, and R, each are fatty acid groups of 10-24 carbon atoms, preferably unsaturated or polyunsaturated fatty acid groups, i.e., a group of the formula OOCR wherein R is alkyl, alkenyl, alkadienyl, etc., of nine-23 carbon atoms, inclusive, and X is a hydrogen atomoracarboxyl group (-COOH).
  • the product of the deamination reaction will also be a single chemical compound, e.g., ba-phosphatidylethylene glycol or L- a-phosphatidylglyceric acid wherein the primary ester group is, e.g., palrnityloxy or stearyloxy and the secondary ester group is oleyloxy, linoleyloxy, or archidonyloxy.
  • the natural sources of the starting phosphatidyl colamines and serines are a mixture of phosphatides containing a mixture of saturated and unsaturated fatty acid residues. Therefore, a preferred embodiment of this invention employs such a mixture to produce a mixture of compounds of Formula I.
  • novel glycol phosphatides which can also be called deaminocephalins, are completely soluble in alcohol, in contrast to the cephalins. They also exhibit a substantially water solubility than the phosphatidyl colamines and phosphatidyl serines. Since they do not possess the blood clotting side-effect of the cephalins, the novel glycol phosphatides are particularly well suited for intravenous fat-feeding. They are also efl'ective oil-in-water emulsifiers for the production of fat emulsions and the like.
  • the glycol phosphatides are also useful as intermediates for the production of corresponding compounds having a substituted OHgroup, for example, ester compounds, and thus are also valuable intermediates for novel drugs.
  • the composition of the fatty acids varies, depending on the starting cephalin employed. In general, the fatty acids having l6 and 18 carbon atoms are predominant,
  • the glycol phosphatides produced therefrom contain, inter alia, C,,,- and C -fatty acids.
  • C,,,- and C -fatty acids When using brain as the source of the starting substance, they additionally contain C -fatty acids.
  • This invention also relates to a process for the preparation of the novel glycol phosphatides of Formula I.
  • They can readily be prepared by dissolving the phosphatidyl colamine or the phosphatidyl serine of the formula O// OH I 11 wherein R R, and X have the values given above, in an organic solvent; mixing the solution with aqueous nitrous acid; and then deaminating the resulting phosphatide compound by diazotization and hydrolysis.
  • the resulting product can be isolated in a conventional manner.
  • the reaction with nitrous acid should be conducted under mild conditions, for example, by conducting the reaction with cooling.
  • the polyunsaturated fatty acid residues of the phosphatidyl compounds are thus not chemically altered. Investigations by spectral analysis and gas chromatography showed that the characteristic lR-band of cephalin at 9.8 p. disappears,'without the double bonds having been affected by the treatment.
  • the nitrous acid is allowed to react with the cephalins by adding an aqueous solution of a salt of nitrous acid and of an acidic salt of an organic or inorganic acid, dropwise to the cephalin-containing organic solution under agitation.
  • This gentle manner of treating with nitrous acid permits the reaction to be conducted at room temperature or with slight heating, without danger of affecting the steric form of the unsaturated fatty acid residues.
  • Suitable solvents for the cephalin-containing starting substances include alcohols and chlorinated hydrocarbons of one to four carbon atoms. Hydrocarbon solvents are also suitable. Chloroforrn proved to be especially suitable as a very advantageous solvent for conducting the dearnination reaction.
  • the deamination process of this invention makes it possible to readily isolate the glycol phosphatides, since their high alcohol solubility facilitates their extraction and separation from accompanying phosphatides.
  • a pure cephalin obtained for example, by column chromatographical separation of cephalin-rich phosphatide fractions on silica gel columns by elution with chloroform-methanol mixtures, or a cephalin-containing phosphatide mixture, which can contain oil or be de-oiled, is dissolved in an alcohol or a chlorinated hydrocarbon of one to four carbon atoms, in a hydrocarbon solvent, e.g., petroleum ether, hexane, cyclohexane, benzene, etc., or a mixture of these solvents.
  • a hydrocarbon solvent e.g., petroleum ether, hexane, cyclohexane, benzene, etc., or a mixture of these solvents.
  • This solution is then mixed, with cooling, at room temperature or slightly higher temperature, with an aqueous solution of nitrous acid, or successively or simultaneously with an aqueous solution of an alkali or alkaline earth salt of nitrous acid and an acidic salt of an inorganic or organic acid, preferably sodium dihydrogen phosphate, sodium hydrogen citrate, or potassium hydrogen phthalate, and agitated in the absence of air until the free amino group associated with the cephalin phosphatides can no longer be detected with ninhydrin reagent.
  • the solvent is entirely or partially evaporated under vacuum and preferably replaced by a chlorinated hydrocarbon.
  • a further advantage of the process of this invention is the fact that the cephalin-free products exhibit advantageous properties, for example, markedly better acid numbers and phosphorous values than the corresponding starting compounds, as can be seen from Table l below.
  • Deaminated product of this invention 70.2 l4.4 3.23 Alcohol-soluble soya phosphatide fraction 85.0 l8.0 3.1
  • the subscript numbers are the number of carbon atoms in the fatty acid residue and the superscript numbers, the number of double bonds.
  • the following fatty acid composition was determined after deamination of a mixture of phosphatidyl colamine and phosphatidyl serine obtained from eggs.
  • EXAMPLE 1 Two hundred g. of pure cephalin (phosphatidyl colamine), produced from an alcohol-insoluble soya phosphatide fraction by separation by column chromatography on silica gel with chloroform-methanol 80 as the eluting agent, is dissolved in a mixture of 1,000 mi. of chloroform and 1,000 ml. of methanol and then mixed, under agitation and in an N, atmosphere, with a solution of 125 g. of sodium nitrite in 200 ml. of distilled water. The mixture is heated in a water bath to 37 C. Then, a solution of 230 g. sodium dihydrogen phosphate 2 H O in 200 ml. of distilled water is gradually added dropwise to the reaction mixture.
  • phosphatidyl colamine phosphatidyl colamine
  • the solvent is decanted from the insoluble material which, after washing with a small amount of chloroform, is
  • EXAMPLE 2 Five hundred g. of the alcohol-insoluble soya phosphatide fraction, as it is obtained as the residue by de-oiling commercial soya phosphatide with acetone and subsequent repeated extraction of the de-oiled product with ethanol under heating, (cephalin content about 30 percent), is dissolved in a mixture of 700 ml. of chloroform and 500 ml. of methanol under agitation and introduction of N and then mixed with a solution of 69 g. of NaNO, in ml. of distilled water. To this mixture is added dropwise, under agitation, a solution of B8 g. of Nal-LPO, H,O in ml.
  • the reaction solution is once more washed with water.
  • 400 g. of a phosphatide mixture is obtained from the chloroform phase (iodine number 70', acid number l4; P 3.2 percent) which contains, in place of cephalin, a glycol phosphatide of this invention corresponding to Formula I in which R, and R, are fatty acid groups and X in a portion thereof is H and in the remainder is -COOH.
  • phosphatide mixture containing the above described glycol phosphatide is dissolved, by agitation and heating to 6070 C., in 10 g. of sunflower oil. After cooling to 20 C., the mixture is transferred into a 100 ml. shaker cylinder and 90 ml. of distilled water of 20C. is added. By a vigorous rotation of the cylinder 90 every 30 seconds, the two phases are emulsified. The number of rotations required to obtain an emulsion stable for 30 seconds are measured. For the cephalin-free product, only two rotations are necessary whereas when employing the starting material, ie the cephalin-containing, alcohol-insoluble phosphatide fraction in the same test no emulsion is obtained, even after 50 rotations.
  • the chloroform-methanol solution is decanted off from the inorganic residue, the residue is washed out with a small amount of chloroform, which is added to the decanted solution.
  • the combined solutions are then stirred with 500 ml. of water under a nitrogen atmosphere, the solution is allowed to settle briefly in a separating funnel and then the lower chloroform layer is separated from the wash water.
  • the chloroform solution is then again washed out twice with 400 ml. portions of water.
  • EXAMPLE 4 One kg. of an alcohol-soluble phosphatide fraction, obtained by de-oiling commercial crude phosphatides with acetone and subsequent repeated extraction of the de-oiled phosphatide mixture with alcohol, is dissolved in 3 liters of ethanol and mixed, under agitation and an atmosphere of N,, with a solution of 120 g. of NaNO, in 120 ml. of water and a solution of 200 g. of Nal-IJ'O, 1 H in 200 ml. of water. Both salts are dissolved with heating in distilled water. The reaction mixture is warmed to 50" C. under agitation and an atmosphere of N After about 1 hours, the cephalin has been completely diazotized.
  • the reaction solution is decanted off from the residue, and the residue is washed with a small amount of ethanol, which is mixed with the reaction solution.
  • the alcohol is distilled off up to about 700 ml. and about [.5 liters of chloroform is added to the residue.
  • the solution is washed out two to three times with about 300 ml. portions of water and the washing water is discarded.
  • the chloroform solution is evaporated under a vacuum and a nitrogen atmosphere. There remains 950 g. (95 percent) of the cephalin-free mixture containing a glycol phosphatide exhibiting the following characteristics: iodine number 82; acid number 4; P 3.2 percent.
  • EXAMPLE 5 One kilogram of commercial crude soya phosphatide is dissolved in 1.2 liters of dichloroethane and 600 ml. of ethanol under a protective N, atmosphere and, under agitation at a temperature of 50 C., is then mixed successively with a solution of 100 g. of NaNO, in 120 ml. of water and 170 g. of Nal-l P0 1 H O in 175 ml. of water. It is advantageous to add the sodium hydrogen phosphate solution gradually dropwise. After agitating for 2.5 hours, the reaction mixture is free of cephalin. Afier cooling to room temperature.
  • the solution is decanted, the semi-solid residue is washed with dichloroethane, the washing liquid is added to the primary solution, and the dichloroethane-ethanol solution is washed two to three times with about 250 ml. portions of water. After the solvent has been distilled off under a vacuum and N 950 g. of an oil-containing, cephalin-free crude phosphatide remains.
  • EXAMPLE 6 One kg. of the same alcohol-insoluble soya phosphatide fraction as employed in Example 2 is dissolved, under agitation and a protective inert gas atmosphere, in 2 liters of hexane and, after heating to 50 C., is mixed with a solution of 200 g. of sodium nitrite in 325 ml. of water. To the reaction mixture is added dropwise a solution of 400 g. of sodium dihydrogen phosphate in 550 ml. of water. After a total of 2.5 hours of intensive agitation, the phosphatide fraction is cephalin-free. The reaction mixture is suitably allowed to cool in a refrigerator, and then the solution which forms at the top is decanted.
  • the residue is repeatedly washed with hexane.
  • the hexane solutions are combined and then shaken out about three times with 300 ml. portions of water.
  • the aqueous phases are separated, if necessary by brief centrifugation, and discarded.
  • the hexane solutions are freed of the solvent under vacuum, leaving 750 g. of a phosphatide mixture containing, in place of cephalin, a glycol phosphatide of this invention.
  • EXAMPLE 7 Five hundred g. of an alcohol-soluble phosphatide fraction, obtained in accordance with the process of German Patent No. 1,047,597, is dissolved in a mixture of 700 ml. of chloroform and 500 ml. of methanol and mixed, under agitation and heating to 50 C., successively with a solution of g. of sodium nitrite in 200 ml. of water and a slurry of 185 g. of potassium hydrogen phthalate in ml. of water. After 7 hours, the reaction mixture is free of cephalin. After cooling, the solution formed on top is decanted from the insoluble substance, which is then washed with chloroform.
  • the washing liquor is combined with the chloroformmethanol solution and washed repeatedly with about ml. of water. Then, the chloroform solution is evaporated under vacuum and nitrogen. Yield: 450 g. of an alcohol-soluble phosphatide mixture containing a glycol phosphatide of this invention.
  • EXAMPLE8 One hundred and eighty g. of crude egg phosphatide, produced from fresh egg yolk by treatment with acetone to remove the neutral lipids and the cholesterol, and then by extraction of the oil-free residue with chloroform-methanol (2:1) and washing out the water-soluble components according to the procedure of J. Folch and co-worker (J. Biol. Chem.
  • EXAMPLE 9 Five hundred g. of an alcohol-soluble phosphatide fraction, obtained as described in Example 4, is dissolved in 1.5 liters of ethanol and mixed at room temperature with an aqueous solution of nitrous acid cooled to C., produced by adding dropwise, under ice cooling, 470 ml. of 12.5 percent hydrochloric acid to 200 g. of sodium nitrite dissolved in a mixture of 800 ml. of water and 250 ml. of ethanol. Afier agitating for three hours under a protective nitrogen atmosphere, the phosphatide mixture no longer exhibits any reaction to ninhydrin reagent. By adding chloroform, two layers are formed, of which the lower layer is separated and washed with water. After evaporating the solvent under vacuum and a protective nitrogen atmosphere, 470 g. of a mixture containing glycol phosphatide is obtained.
  • R, and R are substantially entirely C -C fatty acid groups.
  • a process according to claim 6, which comprises mixing a solution of the starting phosphatidyl compound in an organic solvent with an aqueous solution of a salt of nitrous acid and sodium dihydrogen phosphate, sodium hydrogen citrate or potassium hydrogen phthalate.
  • reaction solvent is chloroform

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
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US76231A 1969-09-30 1970-09-28 Glycol phosphatides and the preparation thereof from cephalin Expired - Lifetime US3681412A (en)

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DE19691949399 DE1949399C (de) 1969-09-30 Glycolphosphatidgemische und deren Herstellung

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US (1) US3681412A (fr)
JP (1) JPS4843336B1 (fr)
AT (1) AT296506B (fr)
BE (1) BE756778A (fr)
CH (1) CH553220A (fr)
DK (1) DK138183C (fr)
ES (1) ES384039A1 (fr)
FR (1) FR2070098B1 (fr)
GB (1) GB1277394A (fr)
NL (1) NL7014221A (fr)
SE (1) SE368017B (fr)
TR (1) TR16587A (fr)
ZA (1) ZA706676B (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4104403A (en) * 1976-12-21 1978-08-01 Witco Chemical Corporation Water-oil emulsions and method of preparing same
US4370319A (en) * 1980-06-19 1983-01-25 The Procter & Gamble Company Skin conditioning compositions
US4408052A (en) * 1980-02-27 1983-10-04 Takeda Chemical Industries, Ltd. Phospholipid carbamates
US4469635A (en) * 1980-12-24 1984-09-04 The Procter & Gamble Company Polyol esters of alpha-hydroxy carboxylic acids
US6878532B1 (en) 2003-04-28 2005-04-12 Sioux Biochemical, Inc. Method of producing phosphatidylserine

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3532724A (en) * 1967-05-31 1970-10-06 Robert R Smeby Renin inhibitor and process to make same
US3577446A (en) * 1968-09-09 1971-05-04 American Home Prod Phosphatidylalkanolamine derivatives

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3532724A (en) * 1967-05-31 1970-10-06 Robert R Smeby Renin inhibitor and process to make same
US3577446A (en) * 1968-09-09 1971-05-04 American Home Prod Phosphatidylalkanolamine derivatives

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4104403A (en) * 1976-12-21 1978-08-01 Witco Chemical Corporation Water-oil emulsions and method of preparing same
US4408052A (en) * 1980-02-27 1983-10-04 Takeda Chemical Industries, Ltd. Phospholipid carbamates
US4565865A (en) * 1980-02-27 1986-01-21 Takeda Chemical Industries, Ltd. Phospholipid carbamates
US4370319A (en) * 1980-06-19 1983-01-25 The Procter & Gamble Company Skin conditioning compositions
US4469635A (en) * 1980-12-24 1984-09-04 The Procter & Gamble Company Polyol esters of alpha-hydroxy carboxylic acids
US6878532B1 (en) 2003-04-28 2005-04-12 Sioux Biochemical, Inc. Method of producing phosphatidylserine
US7049107B1 (en) 2003-04-28 2006-05-23 Sioux Biochemical, Inc. Method of producing phosphatidylserine

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TR16587A (tr) 1973-01-01
SE368017B (fr) 1974-06-17
FR2070098B1 (fr) 1975-04-18
DE1949399A1 (de) 1971-04-01
ES384039A1 (es) 1972-12-16
AT296506B (de) 1972-02-25
DK138183C (da) 1979-01-08
FR2070098A1 (fr) 1971-09-10
CH553220A (de) 1974-08-30
GB1277394A (en) 1972-06-14
NL7014221A (fr) 1971-04-01
ZA706676B (en) 1971-06-30
DK138183B (da) 1978-07-24
JPS4843336B1 (fr) 1973-12-18
BE756778A (fr) 1971-03-01

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