6-Hydroxyisocaryophyllene and isocaryophyllenic acid from birches vegetative buds

The new isocaryophyllene derivatives were first detected in the birch vegetative buds. The structure of 6-hydroxyisocaryophyllene [(1R,4Z, 6R, 9S)-8-methylene-11,11-dimethylbicyclo[7.2.0]undec-4-ene-6-ol] isolated from the Betula pendula Roth. birch buds was determined by NMR spectroscopy. The structures of caryophyllenic acid and isocaryphyllenic acid isolated from the Betula grandifolia Litv., B. albo-sinensis Burk., B. fusca Pall.ex Georg, B. obscura A. Kotula, B. litwinowii Doluch., B. hallii Howell, B. grandifolia Litv. birch buds was determined by X-ray diffraction analysis. The physico-chemical characteristics and NMR data of 6-hydroxyisocaryophyllene, epoxide of 6-hydroxyisocaryophyllene and all the isolated acids are given. The gas chromatographic retention indices of all identified compounds were determined.

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A new approach to the prediction of gas chromatographic retention indices from physico-chemical constants

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19912042 ◽

1991 ◽

Vol 56 (10) ◽

pp. 2042-2054 ◽

Cited By ~ 15

Author(s):

Igor G. Zenkevich ◽

Lyudmila M. Kuznetsova

Keyword(s):

Molecular Weight ◽

Stationary Phases ◽

Retention Indices ◽

Molar Refraction ◽

Boiling Temperature ◽

Chromatographic Retention ◽

New Approach ◽

Physico Chemical ◽

Gas Chromatographic Retention Indices ◽

Chromatographic Retention Indices

A general approach is proposed to the calculation of gas chromatographic retention indices (RI) of organic compounds on standard polydimethylsiloxane stationary phases based on their principal physico-chemical constants such as the boiling temperature, molar refraction or molecular weight. A combination of logical criteria was established for comparing functions of the above parameters for the identification of substances whose RI values are only determined by their boiling temperatures. It is demonstrated that within homologous series, the dependence of the RI value on the boiling temperature or any additive molecular parameter (molecular weight, molar refraction, number of carbon atoms in the molecule, etc.) is nonlinear. If this dependence is taken into account, the RI value of any organic compound can be predicted with a precision comparable to the standard deviation of the statistically processed values determined in nonequivalent conditions.

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p-COUMARATES OF BETULA PENDULA (BETULACEAE) VEGETATIVE BUDS SESQUITERPENE ALCOHOLS

chemistry of plant raw material ◽

10.14258/jcprm.2020026607 ◽

2020 ◽

pp. 127-132

Author(s):

Dmitriy Nikolaevich Vedernikov ◽

Elizaveta Mihailovna Ipanova

Keyword(s):

Antimicrobial Activity ◽

Betula Pendula ◽

Retention Indices ◽

Methyl Tert Butyl Ether ◽

Chromatographic Retention ◽

Klebsiella Pneumonia ◽

Alcoholic Extract ◽

Butyl Ether ◽

Vegetative Buds ◽

Physico Chemical

The composition of coumarates sesquiterpene alcohols of Betula pendula Roth. birch vegetative buds was determined. Fraction was isolated from buds extract by preparative liquid chromatography. The extract was isolated by sequential extraction of an alcoholic extract of the buds with methyl tert-butyl ether. The new sesquiterpene derivatives were first detected in the birch vegetative buds. The structure of 6-hydroxyisocaryophyllene [(1R,4Z,6R,9S)-8-methylene-11,11-dimethylbicyclo[7.2.0]undec-4-ene-6-ol] trans-p-coumarate isolated from the birch buds was determined by NMR spectroscopy. The physico-chemical characteristics and NMR data of 6-hydroxyisocaryophyllene p-coumarate and others coumarates are demonstrated. The gas chromatographic retention indices of all identified compounds were determined. Birch buds contain derivatives of trans-coumaric acid. The antimicrobial activity of sesquiterpene alcohols coumarates was evaluated. The antimicrobial activity of sesquiterpene alcohols coumarates in relation to the following microorganisms: Escherichia coli, Proteus mirabilis, Staphylococcus aureus, Staphylococcus pneumonia and Klebsiella pneumonia was evaluated. The fraction of sesquiterpene alcohols coumarates showed activity against Staphylococcus epidermidis.

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