ABSTRACT
Cholesteryl 3",4"-dimethoxycinnamate (7) and a new synthesized o-coumaroyl ester of 3 beta-(2'-hydroxyethoxy)-cholest-5-en (13) exhibited a marked activity against poliovirus type 1 (Mahoney). Compound 7 showed an approximately 20-fold greater selectivity in its antiviral activity than compound 13. These compounds were selected from thirteen steryl esters of cinnamic acid derivatives through an in vitro antiviral screening against viruses belonging to taxonomic groups with causative agents of important human infectious diseases to which chemotherapy is indicated, i.e. Picornaviridae, Orthomyxoviridae, Paramyxoviridae and Herpesviridae.
Subject(s)
Antiviral Agents/chemical synthesis , Cholesterol Esters/chemical synthesis , Cinnamates/chemical synthesis , Antiviral Agents/chemistry , Antiviral Agents/pharmacology , Cholesterol Esters/chemistry , Cholesterol Esters/pharmacology , Cinnamates/chemistry , Cinnamates/pharmacology , Herpesviridae/drug effects , Humans , Microbial Sensitivity Tests , Molecular Structure , Orthomyxoviridae/drug effects , Paramyxoviridae/drug effects , Picornaviridae/drug effects , Poliovirus/drug effects , Structure-Activity Relationship , Virus DiseasesABSTRACT
Steroid esters of cynnamic acid derivatives have been synthesized by a heterogeneous Wittig reaction under sonochemical conditions from the corresponding triphenylphosphonium bromides and unprotected phenolic aldehyds using K2CO3 as a base. 5 beta-Cholan-3 alpha, 7 alpha, 12 alpha, 24-E-ferulate (11') exhibited a marked inhibitory effect on influenza virus A. The synthetic 3 alpha, 24-E-diferulates of 5 beta-cholan-3 alpha, 24- diol, 5 beta-cholan-3 alpha, 12 alpha, 24-triol and 5 beta-cholan-3 alpha, 7 alpha, 12 alpha, 24-tetrol (8, 9 and 12) showed antitumor activity on leukemia P-388 in mice.
Subject(s)
Antineoplastic Agents/chemistry , Antiviral Agents/chemistry , Cholic Acids/chemistry , Cinnamates/chemistry , Cinnamates/therapeutic use , Leukemia P388/drug therapy , Viruses/drug effects , Animals , Antineoplastic Agents/therapeutic use , Antineoplastic Agents/toxicity , Antiviral Agents/pharmacology , Cell Line , Cinnamates/toxicity , Influenza A virus/drug effects , Male , Mice , Mice, Inbred DBA , Microbial Sensitivity Tests , Molecular Structure , Nuclear Magnetic Resonance, BiomolecularABSTRACT
The free sterols, the sterol esters and the sterol glycosides of the raw soya and corn oils as well as those of the technical lecithin and the deodorizer distillated of the latter oils were isolated by preparative TLC. The composition of each of the isolated sterol derivatives was determined by GLC and MS. Sitosterol, campesterol, stigmasterol and an unknown sterol with a molecular weight of 428 are contained in almost all of the examined fractions of the soya oil and its refinement byproducts. Dehydrocampesterol is present in the free sterols of the raw soya oil and the soya lecithin. Stigmasterol is contained in the soya deodorizer distillate in high amounts. It was established that cholesterol was present in the sterol esters of the raw soya oil high amounts. Delta7-stigmastenol occurs only in the sterol esters of the latter oil. Sitosterol, campesterol and stimgasterol are the main components of all sterol fractions of the corn oil and its refinement products. Dehydrocampesterol and unknown sterols with molecular weights of 428 are present in the free sterols of the raw corn oil. Some sterol glycosides of the soya and corn lecithin are esterified with the same major fatty acid components of the glycerides, palmitic acid being the main one. The fatty acid compositon of sterol esters of the raw soya and corn oil roughly corresponds to the fatty acid composition of oils.
Subject(s)
Oils/analysis , Phytosterols/analysis , Plants/analysis , Chromatography, Gas , Chromatography, Thin Layer , Glycosides/analysis , Mass Spectrometry , Phosphatidylcholines/analysis , Glycine max , Zea mays/analysisABSTRACT
The free sterols, the sterol esters and the sterol glycosides of the crude sunflower oil as well as those of the technical lecithin, the pitch and the deodorizer distillate of the latter oil were isolated by preparative TLC. The nature of sterols contained in the isolated sterol derivatives was elucidated by GLC and combinded GLC-MS. Major sterols of all examined sterol fractions are sitosterol, campesterol and stigmasterol, the amount of sitosterol being prevalent. Unknown sterol with a molecular weight of 428 is present in sterols of the crude oil and the deodorizer distillate. Sterols of the deodorizer distillate contain an unknown sterol with a molecular weight of 430. Stigmasterol is present in the sterol fraction of the deodorizer distillate in high amounts. It was established that delta7-sterols of the crude oil occur only in esterified form. The hydrolysis of the sterol derivatives in acid medium leads to dehydration products known as steroid dienes and disteroid ethers. Hydrolysis without dehydration was achieved by enzyme preparations. Some sterols of the crude oil were esterified with the same higher fatty acids contained in the glycerides of the sunflower oil.
Subject(s)
Oils/analysis , Phytosterols/analysis , Plants/analysis , Chromatography, Gas , Chromatography, Thin Layer , Glycosides/analysis , Helianthus , Mass Spectrometry , Phosphatidylcholines/analysis , Spectrophotometry, InfraredABSTRACT
The amounts of free sterols, steryl esters and steryl glycosides in sunflower, soya and maize oils as well as in the phosphatides of the same oils were determined. The refinement byproducts were enriched with sterols. The highest contents of total sterols and steryl glycosides (2,68 and 1,9%, respectively) were established in soya phosphatides followed by those in sunflower oil phosphatides (2,03 and 1,68%, respectively) and maize oil phosphatides (0,81 and 0,54%, respectively).
