3-O-METHYLQUERCETIN FROM Serratula V. I. Glyzin, A. I. Ban'kovskii, and T. M. Mel'nikova inermis UDC 547.972 Apigenin and luteolin have been isolated previously from Serratula inermis [11. We have isolated a third compound from the inflorescences of this plant. The present paper gives the results of the identification cf this compound. The inflorescences of the plant under consideration, collected in the botanical garden of the All-Union Scientific-Research Institute of Medicinal Plants VILR,were extracted with methanol. The methanol extracts were distilled, and the residue was treated with hot water. The flavonoids were extracted from the aqueous solution with ethyl acetate. The concentrated ethyl acetate extract was chromatographed on polyamide sorbent. Elution with a mixture of chloroform and methanol (9 : 1) gave a substance with the composition C16H1207, mp 257-262°C. The NMR spectrum of this substance (taken in deuteroacetone) had the following signals of protons of methoxy groups: singlet at 3.80 ppm, H-6, doublet (J=2.5 Hz); 6.16 ppm, H-8, doublet (J=2.5 Hz); 6.40 ppm, H-3', doublet (J=9 Hz); 6.90 ppm, H-2', two doublets (J1=2.5, J2=9 Hz); 7.44 and 7.53 ppm, H-6', doublet (J=2.5 Hz); and 7.60 ppm, and a singlet at 12.70 ppm, corresponding to the proton of a hydroxy group in position 5. The absence from the NMR spectrum of a signal from a proton in position 3 and the results of UV spectroscopy show that the hydroxyl in this position is substituted by a methyl group. The demethylation of the substance led to the formation of quercetin, identified by direct comparison with an authentic sample. On the basis of the above facts, the substance was identified as 3-O-methylquercetin [2], being the main component of the inflorescences of Serratula inermis. 1. 2. LITERATURE CITED Ya. K. Yatsyuk and S. S. Lyashchenko, Khim. Prirodn. Soedin., 54 (1969). T. K. Chumbalov, O. V. Fadeeva, and I. S. Chanysheva, Khim. Prirodn. Soedin., 236 (1969). All-Union Scientific-Research Institute of Medicinal Plants. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 389-390, May-June, 1972. Original article submitted January 11, 1972. © 1974 Consultants Bureau, a division of Plenum Publishing Corporation, 227 West 17th Street, New York, N. Y. 10011. No part of this publication may be reproduced, stored in a retrieval system, or transmitted, in any form or by any means, electronic, mechanical, photocopying, microfilming, recording or otherwise, without written permission of the publisher. A copy of this article is available from the publisher for $15.00. 383

3-O-methylquercetin from Serratula inermis

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3 - O - M E T H Y L Q U E R C E T I N F R O M S e r r a t u l a

V. I . G l y z i n , A. I . B a n ' k o v s k i i , a n d T . M. M e l ' n i k o v a

i n e r m i s

UDC 547.972

Apigenin and luteolin have been isolated previously from Serratula inermis [11. We have isolated a third compound from the inflorescences of this plant.

The present paper gives the results of the identification cf this compound. The inflorescences of the plant under consideration, collected in the botanical garden of the All-Union Scientific-Research Institute of Medicinal Plants VILR,were extracted with methanol. The methanol extracts were distilled, and the residue was t reated with hot water. The flavonoids were extracted from the aqueous solution with ethyl acetate. The concentrated ethyl acetate extract was chromatographed on polyamide sorbent. Elution with a mixture of chloroform and methanol (9 : 1) gave a substance with the composition C16H1207, mp 257-262°C.

The NMR spectrum of this substance (taken in deuteroacetone) had the following signals of protons of methoxy groups: singlet at 3.80 ppm, H-6, doublet (J=2.5 Hz); 6.16 ppm, H-8, doublet (J=2.5 Hz); 6.40 ppm, H-3' , doublet (J=9 Hz); 6.90 ppm, H-2', two doublets (J1=2.5, J2=9 Hz); 7.44 and 7.53 ppm, H-6' , doublet (J=2.5 Hz); and 7.60 ppm, and a singlet at 12.70 ppm, corresponding to the proton of a hydroxy group in position 5. The absence f rom the NMR spectrum of a signal from a proton in position 3 and the results of UV spectroscopy show that the hydroxyl in this position is substituted by a methyl group.

The demethylation of the substance led to the formation of quercetin, identified by direct comparison with an authentic sample.

On the basis of the above facts, the substance was identified as 3-O-methylquercetin [2], being the main component of the inflorescences of Serratula inermis.

L I T E R A T U R E C I T E D

Ya. K. Yatsyuk and S. S. Lyashchenko, Khim. Prirodn. Soedin., 54 (1969). T. K. Chumbalov, O. V. Fadeeva, and I. S. Chanysheva, Khim. Prirodn. Soedin., 236 (1969).

All-Union Scientific-Research Institute of Medicinal Plants. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 389-390, May-June, 1972. Original art icle submitted January 11, 1972.

© 1974 Consultants Bureau, a division of Plenum Publishing Corporation, 227 West 17th Street, New York, N. Y. 10011. No part of this publication may be reproduced, stored in a retrieval system, or transmitted, in any form or by any means, electronic, mechanical, photocopying, microfilming, recording or otherwise, without written permission of the publisher. A copy of this article is available from the publisher for $15.00.

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