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PHENOLIC COMPOUNDS OF Elaeagnus angustifolia A. G. Nikolaeva, P. E° Krivenchuk, and A. P. Prokopenko UDC 581.192:5.98 The epigeaI part of Elaeagnus angustifolia L. (Russian olive) collected in the flowering period in the environs of Zaporozhe has been investigated in order to determine its content of phenolic compounds. The leaves were extracted with ethanol, and the aqueous residue was purified with chloroform, acid- ified with 15% sulfuric acid to pH 2-3, and extracted with ethyl acetate. By preparative paper chromatog- raphy, the ethyl acetate extracts yielded substances I, II, and III, giving positive qualitative reactions for phenolcarboxylic acids, their Rf values being, respectively, 0.28, 0.52, and 0.65 {0.1 N HC1 system). Substance I, CgHsO4, had mp 195-197°C (from 50% ethanol). UV spectrum: -maxX c~H~°H 325, 299, 235; k A1cl~max )tC~HsONa 360, 315, 240; kCH3COONa 510: 280;, ~ HzBO~÷CH'COGNa 320, 295; -max 350, 250 The alkaline fusion of I formed -max 'max protacatechuic acid. The substance gave no depression of the melting point in admixture with a sample of caffeic acid. Substance II, Ci6HtsO 9, had mp 203-205°c (from 50% methanol). UV spectrum: )`Cm~[~°°a 325, 240; x ~ 360, 318, 240; )` cttscOoNa HsBOa+CHa COONa 250; C,HsONa max 330; )'max 350, )`mix 380, 260. The products of alkaline hydrolysis included eaffeic and D-quinic acids. On alkaline fusion, protocatechuic acid was formed; no lactonization took place under the influence of acetic acid. Substance II showed no depression of the melting point in admixture with chlorogenic acid and was identical with the latter. ) C~H~ONa Substance III. UV spectrum: x c~m°a 330, 250; ?xlcl~aaa 310, 235; ~.CHaGOONa 325; ~HsBOa+CHaCOONa 350, 250; -'max -max max ~, max max 370, 260. On alkaline hydrolysis caffeie and D-quinic acids were obtained. On two-dimensional ehromato- grams, a mixture of substance III and of neochlorogenic acid yielded a single spot. In an acetone extract of the bark of the Russian olive obtained after the treatment of the raw material with a mixture of benzene and chloroform (1 : 1) we found four catechin derivatives by paper chromatog- raphy in the butan-l-ol-acetic acid-water (40 : 12, 5 : 29) system. Two substances were identified as (+)-catechin (Rf 0.68) and (-)-epicatechtn (Rf 0.58)inatwo-dimensional chromatographic study in parallel with authentic samples kindly given to us by L. T. Pashinina (Alma-Ata). Zaporozhe Medical Institute. Khar'kov Scientific-Research Institute of Pharmaceutical Chemistry. Translated from Khimiya Prirodnykh Soedinenii, No. 6, p. 765, November-December, 1970. Original arti- cle submitted June 20, 1970. © 1973 Consultants Bureau, a division of Plenum Publishing Corporation, 227 West 17th Street, New York, N. Y. 10011. All rights reserved. This article cannot be reproduced for any purpose whatsoever without permission of the publisher. A copy of this article is available from the publisher for $15.00. 778

Phenolic compounds of Elaeagnus angustifolia

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Page 1: Phenolic compounds of Elaeagnus angustifolia

P H E N O L I C C O M P O U N D S O F E l a e a g n u s a n g u s t i f o l i a

A . G. N i k o l a e v a , P . E° K r i v e n c h u k , a n d A . P . P r o k o p e n k o

UDC 581.192:5.98

The epigeaI par t of Elaeagnus angustifolia L. (Russian olive) col lected in the f lowering period in the environs of Zaporozhe has been invest igated in o r d e r to de te rmine its content of phenolic compounds.

The leaves were ex t rac ted with ethanol, and the aqueous res idue was purif ied with ch loroform, ac id- ified with 15% sulfur ic acid to pH 2-3, and ex t rac ted with ethyl ace ta te . By p r e p a r a t i v e p a p e r ch romatog- raphy, the ethyl ace ta te ex t r ac t s yielded subs tances I, II, and III, giving pos i t ive quali tat ive react ions for phenolcarboxyl ic acids , the i r Rf values being, r e spec t ive ly , 0.28, 0.52, and 0.65 {0.1 N HC1 sys tem) .

Substance I, CgHsO4, had mp 195-197°C ( f rom 50% ethanol). UV spec t rum: -maxX c~H~°H 325, 299, 235; k A1cl~max )tC~HsONa 360, 315, 240; kCH3COONa 510: 280;, ~ HzBO~÷CH'COGNa 320, 295; -max 350, 250 The alkal ine fusion of I formed -max 'max

protaca techuic acid. The subs tance gave no dep res s ion of the mel t ing point in admixture with a sample of caffeic acid.

Substance II, Ci6HtsO 9, had mp 203-205°c ( f rom 50% methanol) . UV spec t rum: )̀Cm~[~°°a 325, 240; x ~ 360, 318, 240; ) ̀cttscOoNa HsBOa+CHa COONa 250; C,HsONa max 330; )'max 350, )`mix 380, 260. The products of alkaline hydro lys i s included eaffeic and D-quinic acids . On alkal ine fusion, protocatechuic acid was formed; no lactonizat ion took place under the influence of acet ic acid. Substance II showed no dep res s ion of the mel t ing point in admixture with chlorogenic acid and was identical with the la t te r .

) C~H~ONa Subs tance III. UV s p e c t r u m : x c~m°a 330, 250; ?xlcl~aaa 310, 235; ~.CHaGOONa 325; ~HsBOa+CHaCOONa 350, 250; -'max -max max ~ , max max

370, 260. On alkal ine hydro lys i s caffeie and D-quinic acids were obtained. On two-d imens iona l e h r o m a t o - g r a m s , a mixture of substance III and of neochlorogenic acid yielded a single spot .

In an acetone ex t rac t of the bark of the Russ ian olive obtained a f t e r the t r e a t m e n t of the raw ma te r i a l with a mixture of benzene and ch lo ro fo rm (1 : 1) we found four catechin der iva t ives by pape r ch romatog- raphy in the b u t a n - l - o l - a c e t i c a c i d - w a t e r (40 : 12, 5 : 29) sys t em. Two subs tances were identified as (+)-catechin (Rf 0.68) and ( - ) -ep ica techtn (Rf 0 .58) ina two-d imens iona l chromatograph ic study in pa ra l l e l with authentic s amples kindly given to us by L. T. Pashinina (Alma-Ata) .

Zaporozhe Medical Inst i tute . Khar 'kov Sc ien t i f i c -Resea rch Insti tute of Pha rmaceu t i ca l Chemis t ry . T rans la t ed f rom Khimiya Pr i rodnykh Soedinenii, No. 6, p. 765, N o v e m b e r - D e c e m b e r , 1970. Original a r t i - cle submit ted June 20, 1970.

© 1973 Consultants Bureau, a division of Plenum Publishing Corporation, 227 West 17th Street, New York, N. Y. 10011. All rights reserved. This article cannot be reproduced for any purpose whatsoever without permission of the publisher. A copy of this article is available from the publisher for $15.00.

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