Sobolev-Butovсhenko E. Triterpene glycosides of Fatsia japonica

Українська версія

Thesis for the degree of Candidate of Sciences (CSc)

State registration number

0405U003102

Applicant for

Specialization

  • 02.00.10 - Біоорганічна хімія

07-07-2005

Specialized Academic Board

Д 41.219.02

Essay

Object of investigation: Leaves, seeds, fruits and flower knops of Fatsia japonica. Aim of investigation: isolation and structure elucidation individual triterpene glycosides from different parts of Fatsia japonica, Investigation of hemolytic activity and hyperpolarisation action on isolating neurones of triterpene glycosides. Methods of investigation and equipment: one- and two-dimensional thin-layer chromatography, preparative chromatography, chemical methods (complete and partial acid hydrolysis, alkalis and mild alkalis hydrolysis, diazomethane methylation, deacetylation, borohydride reduction), fermentative hydrolytic methods, NMR-specrtometry methods (1H-ЯМР, 13С-ЯМР, COSY, TOCSY, HSQC, HMBC, ROESY). Theoretical results and their novelty: For the first time the complex study glycoside composition of various parts Fatsia japonica – leaves, seeds, fruits and flower knops was carried out. The construction of 41 triterpene glycosides is found, 32 from which have not been found in Fatsia japonica earlier, and 14 glycosides are new compounds. Presence in Fatsia japonica significant amount before unknowns of acetylated glycosides proved. It proved that in Fatsia japonica there are 11 glycosides etherified by one or several fragments of an acetic acid. From flower knops of Fatsia japonica two new acetylated glycosides echinocystic acid were isolated: 3-O-(3-O-acetyl-a-L-arabynopyranosyl)- and 3-O-(4-O-acetyl-a-L-arabynopyranosyl)-28-O-a-L-rhamnopyranosyl-(1-4)-O-(6-O-acetyl-b-D-glucopyranosyl)-(1-6)-O-b-D-glucopyranoside esters of echinocystic acid was isolated. From seeds of Fatsia japonica 4 new hypsogenin glycoside were isolated: 3-O-b-D-glucopyranosyl-(1-2)-O-b-D-glucopyranoside of hypsogenin, 3-O-b-D-galactopyranosyl-(1-2)-O-b-D-glucopyranoside of hypsogenin and its 28-O-b-D-glucopyranosyl-(1-6)-O-b-D-glucopyranoside esters. For the first time it is investigated hyperpolarisation action triterpene glycosides on neurones of molluscum Helix pomatia. Practical results and their novelty: on the basis of complex research glycoside composition of various parts of Fatsia japonica, it is shown, that this plant is an available source for deriving triterpene glycosides both known earlier, and isolating for the first time. Procedures of abjection triterpene glycosides that has allowed to receive 41 glycoside have been offered and spent, 32 from which have not been found in Fatsia japonica, and 14 are new compounds. It is shown, that triterpene glycosides have hemolytic activity and render hyperpolarisation action on neurones molluscum Helix pomatia. It is the establishment for search of active agents new physiologically in series triterpene glycosides. Subject and the degree of introduction: publications, reports at the scientific conferences, using the results of work in the scientific and pedagogical practice of establishments of higher education and Scientific Research Institutes of Ukraine. Efficiency of introduction is ensured by the development of ways to analysis, isolation and structure elucidation of triterpene glycosides and by selected glycosides with high biological activity. Sphere of use: chemistry, biology, medicine.

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