Xanthoxylin from Artemisia santolina and A. scotina

XANTHOXYLIN FROM Artemisia santolina B. Akyev, M. I. Yusupov, Sh. Z. Kasymov, and G. P. AND A. scotina UDC 547.913.5 Sidyakin In a study of the lactones of the epigeal p a r t of A r t e m i s i a santolina Schrenk [1, 2] and A. scotina Nevski [3], a s an a c c o m p a n y i n g component we isolated a substance with the composition C10H1204, mp 79-80°C (from ethanol). The yield f r o m the f i r s t plant was 0.22% and f r o m the second 0.01% (of the weight of the dried plant). The s u b s t a n c e was isolated by treating c h l o r o f o r m e x t r a c t s with p e t r o l e u m e t h e r and also by c h r o m a tography on neutral alumina o r s i l i c a gel. The IR s p e c t r u m of the substance shows the a b s o r p t i o n bands of stretching v i b r a t i o n s at Vmax 2955 and 2840 c m -1 (methoxy groups), a b r o a d band at 1580-1620 cm -1 (carbonyl group conjugated with an a r o m a t i c nucleus) and 1510 and 1460 cm -1 ( - C t t = C H - bond of a benzene n u c l e u s ) , a n d a w e a k b a n d a t 3 4 5 0 c m -1 c o r r e s p o n d s to a phenolic hydroxyl. The UV s p e c t r u m of the compound isolated ~ m a x 213, 225, 290 nm; log ~ 4.05, 3.99, 4.10, r e s p e c tively) c o n f i r m s the p r e s e n c e of a conjugated carbonyl group. The NMR s p e c t r u m of the substance (CDCI~, taken on a C-60HL i n s t r u m e n t with HMDS as internal standard; h e r e and below,the ~ scale) showed a singlet (3H) at 2.48 p p m assigned to the protons of an acetyl group (CH3CO-) attached to an a r o m a t i c ring. Two singlets in the 3.65 and 3.68 ppm region (each of three proton units) show the p r e s e n c e of two methoxy groups. Two doublets at 5.72 and 5.86 p p m (each of one p r o ton unit, J = 4 Hz), f r o m the nature of t h e i r splitting, show the m e t a position of these protons in the benzene ring. The proton of the phenolic hydroxy group a p p e a r s in the f o r m of a singlet (1H) in the 13.8 ppm region. On acetylation with acetic anhydride in pyridine, the substance f o r m e d a monoacetyl derivative, CllH140~, m p 105-107°C (from ethanol), the IR s p e c t r u m of which lacked the a b s o r p t i o n band of a hydroxy •group but showed new m a x i m a at 1752 and 1220 cm -1, which a r e c h a r a c t e r i s t i c f o r an acetyl group. Thus, the substance that we have isolated is 2 - h y d r o x y - 4 , 6 - d i m e t h o x y a c e t o p h e n o n e and is identical With the xanthoxylin isolated p r e v i o u s l y f r o m Xanthoxylum a l a t u m Roxb. and f r o m other plants [4]. This is the f i r s t time that xanthoxylin has been isolated f r o m A. santolina and A. scotina. LITERATURE 1. 2. 3. 4. CITED B. Akyev, Sh. Z. K a s y m o v , and G. P. Sidyakin, Khim. P r i r o d n . Soedin., 730 (1972). B. Akyev, Sh. Z. K a s y m o v , and G. P. Sidyakin, Khim. l>rirodn. Soedin., 733 (1972). M. I. Yusupov and G. P. Sidyakin, Khim. P r i r o d n . Soedin., 667 (1972). W. K a r r e r , Konstitution und V o r k o m m e n d e r o r g a n i s c h e n Pflanzenstoffe, B i r k h a u s e r Verlag, B a s e l (1958), p. 181. Institute of the C h e m i s t r y of Plant Substances, Academy of Sciences of the Uzbek SSR. T r a n s l a t e d f r o m Khimiya P r i r o d n y k h Soedinenii, No. 3, pp. 422-423, May-June, 1973. Original a r t i c l e submitted Dec e m b e r 30, 1972. © 19 75 Plenum Publishing Corporation, 227 West 17th Street, New York, N. Y. 10011. No part o f this publication may be reproduced, stored in a retrieval system, or transmitted, in any form or by any means, electronic, mechanicM, photocopying, microfilming, recording or otherwise, without written permission o f the publisher. A copy o f this arffcle is available from the publisher for $15.00. 390  (...truncated)