Hydrolytic products

Hyoscine (Scopolamine, Atroscine), Ci,H2i04N. The name hyoscine was first used by Hohn and Reichardt for the basie hydrolytic product of hyoscyamine, now known as tropine. It was subsequently used by Ladenburg for a supposed isomeridc of atropine, Cj HjgOjN, isolated from the mother liquors of hyoscyamine. This was found by Schmidt, Hesse and others to be identical with scopolamine, Ci,H2i04N, obtained by Schmidt from Scopolia japonica. The name hyoscine has priority and is in use, but scopolamine is also employed, especially in Germany. 

The formula of hyoscine may now be written as tropylscopine (tropylscopeine by analogy with the tropeines) and the relationship of scopine to oscine, teloidine and tropine, the other principal hydrolytic products of this group, are shown by the following formulae. 

Z-Ecgonine, CgHigOgN. HjO. This substance was first obtained I Lossen as the final basic hydrolytic product of the action of acids c cocaine, and is obtainable in like manner from several of the alkaloii occurring with cocaine (see above). It crystallises from dry alcohol i monoclinic prisms, m.p. 198° (dec.), 205° (dry), [a]n — 45-4°, is soluble i water, sparingly so in alcohol, insoluble in most organic liquid Eegonine forms Salts with bases and acids the hydrochloride crystallis... 

Hydrocotarnine, C12HJ5O3N. HjO. This basic hydrolytic product of narcotine occurs in opium. It crystallises from light petroleum in colourless plates, m.p. 55-5-56-5°, and yields well-crystallised salts of which the hydrobromide, B. HBr, m.p. 236-7°, is sparingly soluble in water. On oxidation, hydrocotarnine is converted into cotarnine, and on reduction by sodium in alcohol it yields hydrohydrastinine (p. 164) by loss of a mcthoxyl group. 

Trachelantamine, according to Syrneva, has a weak atropine-like action and also produces local anaesthesia. Its hydrolytic product, trache-lantamidine, which is structurally identical with tsoretronecanol, yields a p-aminobenzoyl derivative of -which the crystalline hydrochloride, m.p. 230-2°, is said to be as potent a local anaesthetic as cocaine hydrochloride. The chloro- -heliotridane (p. 606) formed by the aetion of thionyl ehloride on trachelantamidine reacts with 6-methoxy-8-aminoquinoline to form 6-methoxy-8-(pseMdoheliotridylamino)-quinoline,... 

Lycoctonine is also the basic, hydrolytic product of some delphinium alkaloids (pp. 694-6). 

CggHjgOjN. HjO, m.p. 143°, [a] ° + 53-2° (EtOH), apparently identical with the basic hydrolytic product of lycaconitine (p. 686) from which methyllycaconitine differs in yielding methylsuccinic acid in place of succinic acid on hydrolysis. This established for the first time similarity in constitution between alkaloids of the two closely related Ranunculaceous... 

Delphinine, C34H47O9N (Walz) or C33H45O9N (J. and C.). The alkaloid crystallises in rhombs, or six-sided plates, m.p. 198-200°, [a]f ° + 25° (EtOH), shows mutarotation in alcoholic solution, and forms an acid oxalate, B. H2C2O4, m.p. 168° dry), a hydrochloride, B. HCl, m.p. 208-210°, and a monobenzoyl derivative, m.p. 171-3°. On alkaline hydrolysis it yields one molecule each of acetic and benzoic acids. The basic, hydrolytic product of this action is delphonine, C24H3g07N, which is amorphous, but can be distilled at a bath temperature of 140° and a pressure of 0-001 to 0-0001 mm. The brittle, possibly semi-crystalline resin so obtained, has m.p, 76-8° and [a]f ° - - 37-5 (EtOH). 

Erythrophleine, C24H3,OgN. This formula, adopted by Blount, Openshaw and Todd, is based on analyses of the sulphate B. 0 5HgSO4, and on the composition of the well-defined hydrolytic products, prepared... 

Ergot alkaloids, 517 characteristics, 519 constitution, 525 dihydro-derivatives, 532 hydrolytic products, 526 pharmacological action, 533 relative sympathicolytic activities, 535... 

Teloidine, the basic hydrolytic product of meteloidine, has been synthesised recently under physiological conditions by Schdpf and Arnold, on the lines of the tropinone synthesis, mesotartaric aldehyde (CHOH. CHO)j, being condensed at 25° with aeetonediearboxylic acid bnd methylamine hydrochloride to teloidinone (5-keto-l 2-dihydroxy-tropane) whieh on eatalytic hydrogenation yielded teloidine (1 2 5-trihydroxytropane). 

Yoshioka T, JA Krauser, FP Guengerich (2002) Tetrachloroethylene oxide hydrolytic products and reactions with phosphate and lysine. Chem Res Toxicol 15 1096-1105. 

Monoacylglycerols are the monoesters of glycerol that consist of only one fatty acid attached either to the position 1(3) or 2 of the glycerol backbone. However, because both diacylglycerols and monoacylglycerols are hydrolytic products of triacylglycer-ols and phospholipids, they may be present, if any, only in negligible levels in animal and plant tissues. 

Phosphatidylcholine, commonly known as lecithin, is the most commonly occurring in natnre and consists of two fatty add moieties in each molecule. Phosphati-dylethanolamine, also known as cephahn, consists of an amine gronp that can be methylated to form other compounds. This is also one of the abundant phospholipids of animal, plant, and microbial origin. Phosphatidylserine, which has weakly acidic properties and is found in the brain tissues of mammals, is found in small amounts in microorganisms. Recent health claims indicate that phosphatidylserine can be used as a brain food for early Alzheimer s disease patients and for patients with cognitive dysfunctions. Lysophospholipids consist of only one fatty acid moiety attached either to sn-1 or sn-2 position in each molecule, and some of them are quite soluble in water. Lysophosphatidylchohne, lysophosphatidylserine, and lysophos-phatidylethanolamine are found in animal tissues in trace amounts, and they are mainly hydrolytic products of phospholipids. 

Most early publications on bacterial polysaccharides were concerned with impure products and poorly-described organisms. Many more recent papers are of limited value also, due to low yields, lack of characterization of products and arbitrary interpretations of data. Low yields of methylated polysaccharides may be due to degradation of the bacterial polysaccharide during methylation, or to degradation of the hydrolytic products of the methylated polysaccharide (to form methyl levulinate, etc.46). The great importance of (a) complete methylation of polysaccharide products prior to structural determination by hydrolysis and (6) quantitative identification of the hydrolytic products, has been emphasized previously. Other difficulties in end group analysis have been discussed recently.7... 

Peat, Schluchterer and Stacey6 later obtained a small amount (0.23%) of methyl 2,3,4,6-tetramethyl-n-glucoside from the hydrolytic products of a methylated L. dextranicum dextran, in addition to 90% methyl 2,3,4-trimethyl-D-glucosides, and on the basis of these results, postulated a minimum chain length of 550 units for this dextran. An appreciable amount of methyl dimethyl-D-glucosides was obtained, but these may not indicate side chain linkages since a mixture of dimethyl isomers was present, and the dextran was not fully methylated (only 44.5% methoxyl rather than 45.6%). 

Polysaccharides of Corynebacterium diphtheriae yield D-galactose, pentoses and amino sugars on hydrolysis.79 D-Glucose and D-mannose are major hydrolytic products of the polysaccharide of Clostridium perfringens.80 Complete hydrolysis81 of the polysaccharide of the anthrax bacillus yielded acetyl-D-glucosamine and D-galactose. 

Challinor, Haworth and Hirst101 determined the chemical structure of the levan produced by the action of B. mesentericus on sucrose. Methylated levan appeared homogeneous when fractionally precipitated from mixed solvents. Fractional distillation of the hydrolytic products of methylated levan yielded tetramethyl-D-fructofuranose in an amount corresponding to a levan chain length of from ten to twelve fructofuranose units, joined as previously940 shown through the 2- and 6-positions. 

Methylation was accomplished by direct conversion of the acetyl derivative as previously described. The final product contained 45% OCHs. Molecular weight determinations in benzene gave values representing 18 to 19 D-fructose residues. Hydrolytic products of the methyl derivative were separated by conversion to benzoyl derivatives. The trimethylfructose was identified as 3,4,6-trimethyl-D-fructofuranose by its phenylosazone. The authors conclude that the ratios 1 3 1 exist among the di-, tri-, and tetramethyl-D -fructoses produced by the hydrolysis. 

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