Synthesis of esters of birch bud sesquiterpene alcohols and cinnamic acid derivatives
https://doi.org/10.21266/2079-4304.2022.238.160-169
Abstract
This research is aimed at creating drugs that inhibit the growth of the microorganism Staphylococcus epidermidis, which causes difficult to treat diseases. The study shows a successful attempt to synthesize natural esters – coumarates of sesquiterpene alcohols from sesquiterpene compounds of birch buds. The chromatographic and mass spectrometric characteristics of the obtained compounds coincide with the characteristics of natural ones. Control over the quality and quantity of intermediate and final products was carried out by gas chromatography-mass spectrometry. The resulting products showed retention times and mass spectra corresponding to natural values. The synthesis included the preparation of a vegetative buds extract, saponification of sesquiterpene alcohol acetate, vacuum distillation of the sesquiterpene alcohol fraction, preparation of coumaric acid acetate, oxalyl chloride, coumaric acid acetate chloride, esters of coumaric acid acetate and sesquiterpene acetyl alcohols, hydrolysis and chromatography of products with silica gel. The product yield, calculated as sesquiterpene alcohols, was 70%. The synthesized compounds, as well as natural ones, showed antimicrobial activity against Staphylococcus epidermidis with a MIC = 1000 μg / ml. The estimated antimicrobial activity was 20 times less than the activity of natural coumarates of sesquiterpene alcohols. The composition of the obtained products differed from natural compounds by the absence of one of the main components – -betulenol coumarate. -Betulenol is absent in free form in birch buds.
About the Authors
D. N. Vedernikov
St.Petersburg State Forestry University
Russian Federation
Russian Federation
VEDERNIKOV Dmitry N. – DSc (Chemistry), Professor, Associate Professor of the Department of Technology of Forest Chemical Products, Wood Chemistry and Biotechnology
194021. Institutskiy per. 5. St. Petersburg
Web of Science ResearcherID: O-2562-2017
Scopus AuthorID: 8
E. A. Ryseva
St.Petersburg State Forestry University
Russian Federation
Russian Federation
RYSEVA Ekaterina A. – Master's degree, graduate of the Department of Technology of Wood Chemical Products, Wood Chemistry and Biotechnology
194021. Institutskiy per. 5. St. Petersburg
References
1. Process for the preparation of oxalyl chloride: DE patent 2840435. Issued 1980-03-27 / Vogel A., Steffan G., Mannes K., Trescher V.
2. Sefkow M. First Efficient Synthesis of Chlorogenic Acid. Eur. J. Org. Chem., 2001, pp. 1137–1141.
3. Sefkow M., Kelling A., Schilde U. First Efficient Syntheses of 1-, 4- and 5-Caffeoylquinic Acid. Eur. J. Org. Chem., 2001, pp. 2735–2742.
4. Shulishov E.V., Klimenko I.P., Tomalin Yu.V. Synthesis of nitrosomethyl urea and its use for the preparation of diazomethane solution – In the synthesis of organic compounds. Collection 3. M.: MAKSpress, 2008, pp. 266–269. (In Russ.)
5. Vedernikov D.N., Galashkina N.G., Roshchin V.I. Esters of buds Betula pendula (Betulaceae). Rastitelnie Resursi, 2007, no. 3, pp. 84–92. (In Russ.)
6. Vedernikov D.N., Ipanova E.M. p-Coumarates of betula pendula (betulaceae) vegetative buds sesquiterpene alcohols. Khimiya rastitel'nogo syr'ya, 2020, no. 2, pp. 127–132. DOI: https://doi.org/10.14258/jcprm.2020026607.
7. Vedernikov D.N., Roshchin V.I. Extractive compounds of birch buds (Betula pendula Roth.): I. Composition of fatty acids, hydrocarbons, and esters. Russian Journal of Bioorganic Chemistry, 2010, vol. 36, no. 7, pp. 894–898.
8. Vedernikov D.N., Roshchin V.I. Extractive compounds of birch buds (Betula pendula Roth.): II. Carbonyl compounds and oxides. Esters. Russian Journal of Bioorganic Chemistry, 2010, vol. 36, no. 7, рр. 899–908.
9. Vedernikov D.N., Roshchin V.I. Extractive substances of the buds of silver birch Betula pendula Roth (Betulaceae). 3. Composition of triterpene acids, flavonoids, alcohols and esters. Khimiya Rastitel'nogo Syr'ya, 2010, no. 4, pp. 67–75. (In Russ.)
Review
For citations:
Vedernikov D.N., Ryseva E.A. Synthesis of esters of birch bud sesquiterpene alcohols and cinnamic acid derivatives. Izvestia Sankt-Peterburgskoj lesotehniceskoj akademii. 2022;(238):160-169. (In Russ.) https://doi.org/10.21266/2079-4304.2022.238.160-169
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