Luteolin 5-O-β-L-galactoside from Dracocephalum nutans

LITERATURE 1. 2. CITED Yu. V. Rostmhin~ A. L. Shinkarenko, and E. T. Oganesyan, Khim. P r i r o d n . Soedin., 472 (1970). V. I. Litvinenko and N. P. Maksyutina, Khim. P r i r o d n . Soedin., 420 (1965). LUTEOLIN 5-O-fl-L-GALACTOSIDE Dracocephalum FROM nutans A. A. Shamyrina, a n d N . I° S h e r g i n a V. A. Peshkova, UDC 547.972 We have p r e v i o u s l y isolated c o s m o s i n i n and c y n a r o s i d e f r o m the h e r b D r a c o c e p h a l u m nutans L. [1]. When an ethanolic e x t r a c t w a s c h r o m a t o g r a p h e d on cellulose, 85% ethanol yielded a flavonoid which we have called DN3o The s u b s t a n c e DN3, C21H20Olt, had m p 220-222°C, Rf 0.18 (15% acetic acid), Vmax (ethanol} 352, 269, 252 nm. Acid h y d r o l y s i s (5% sulfuric acid, 3 h) g a v e the aglycone with m p 326-328°C, Rf 0.46 (60% acetic acid), Vmax {ethanol) : 355, 268, 252 nm. On the b a s i s of the r e s u l t s of p h y s i c . c h e m i c a l and s p e c t r a l investigations in c o m p a r i s o n with an authentic s a m p l e , the aglycone was identified as luteolin [2]. L - G a l a c t o s e , identified b y p a p e r c h r o m a t o g r a p h y , w a s found in the h y d r o l y z a t e . The r e s u l t s of IR s p e c t r o s c o p y and e n z y m a t i c h y d r o l y s i s show the p y r a n o s e f o r m of the s u g a r and the p r e s e n c e of a fl-glycosidic bond [3]. On the b a s i s of the f a c t s given above and the r e s u l t s of UV s p e c t r o s c o p y with c o m p l e x - f o r m i n g and i o n i z ing additives, the s u b s t a n c e DN 3 can be c h a r a c t e r i z e d as lutiotin 5 - O - f l - L - g a l a c t o s i d e . LITERATURE I. 2. CITED A.A. Shamyrina, V. A. Peshkova, and N. I. Shergina, Khin~ Prirodn. Soedin., 255 (1975). T . J . Mabry, K. R. M a r k h a m , and M. B. T h o m a s , The S y s t e m a t i c Identification of Flavonoids, Springer, New Y o r k (1970). I . P . Kovalev and E. V. T i t , v , I n f r a r e d A b s o r p t i o n S p e c t r a of s o m e Groups of Natural Compounds [in R u s sian], K h a r ' kov (1966). 3. Tyumen' State Medical Institute. I r k u t s k Institute of Organic C h e m i s t r y of the Siberian B r a n c h of the A c a d e m y of Sciences of the USSRo T r a n s l a t e d f r o m K h i m i y a P r i r o d n y k h Soedinenii, No. 4, p. 577, A u g u s t - S e p t e m b e r , 1977. Original a r t i c l e submitted April 4, 1977. This material is protected by copyright registered in the name o f 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, I microfilming, recording or otherwise, without written permission o f the publisher. A copy o f this article is available from the publisher for $ 7.50. 482  (...truncated)