Verballoscenine, the Z isomer of verbascenine from Verbascum phoeniceum

被引:13
作者
Drandarov, K
机构
[1] Department of Organic Chemistry, Faculty of Pharmacy, Medical University of Sofia, BG-1000 Sofia
关键词
Verbascum phoeniceum; Verbascum pseudonobile; Scrophulariaceae; leaves; Z-cinnamic acid amide; macrocyclic lactam alkaloids; polyamine; spermine;
D O I
10.1016/S0031-9422(96)00623-1
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The Z isomer (13-acetyl-1-(Z)-cinnamoyl-6-oxo-8-phenyl-1,5,9,13-tetraazacycloheptadecane; verballoscenine) of the 17-membered macrocyclic lactam alkaloid verbascenine was isolated from Verbascum phoeniceum and structurally characterized. The presence in the same plant material of the analogous N-13 non-acetyl alkaloids verbacine and verballocine as precursors in the biogenesis of verbascenine and verballoscenine is reported. Copyright (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:971 / 973
页数:3
相关论文
共 12 条
[1]   Separation of E-Z isomeric macrocyclic spermine alkaloids of Verbascum pseudonobile and Verbascum phoeniceum and of their derivatives using thin-layer chromatography [J].
Drandarov, K ;
Hais, IM .
JOURNAL OF CHROMATOGRAPHY A, 1996, 724 (1-2) :416-423
[2]   VERBACINE AND VERBALLOCINE, NOVEL MACROCYCLIC SPERMINE ALKALOIDS FROM VERBASCUM PSEUDONOBILE STOJ ET STEF (SCROPHULARIACEAE) [J].
DRANDAROV, K .
TETRAHEDRON LETTERS, 1995, 36 (04) :617-620
[3]   STUDIES ON ORCHIDACEAE ALKALOIDS .33. 2 NEW ALKALOIDS, N-CIS-CINNAMOYLNORCUSKHYGRINE AND N-TRANS-CINNAMOYLNORCUSKHYGRINE FROM DENDROBIUM-CHRYSANTHUM WALL [J].
EKEVAG, U ;
ELANDER, M ;
GAWELL, L ;
LEANDER, K ;
LUNING, B .
ACTA CHEMICA SCANDINAVICA, 1973, 27 (06) :1982-1986
[4]  
HAIS IM, HDB PAPIERCHROMATOGR, V1, P932
[5]   CELACINNINE, A NOVEL MACROCYCLIC SPERMIDINE ALKALOID PROTOTYPE [J].
KUPCHAN, SM ;
HINTZ, HPJ ;
SMITH, RM ;
KARIM, A ;
CASS, MW ;
COURT, WA ;
YATAGAI, M .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1974, (09) :329-330
[6]  
LLOYD H. A., 1965, TETRAHEDRON LETT, V50, P4537
[7]   HYDROXYCINNAMIC ACID SPERMIDINE AMIDES FROM POLLEN OF CORYLUS-AVELLANA L [J].
MEURER, B ;
WRAY, V ;
GROTJAHN, L ;
WIERMANN, R ;
STRACK, D .
PHYTOCHEMISTRY, 1986, 25 (02) :433-435
[8]   HYDROXYCINNAMIC ACID-SPERMIDINE AMIDES FROM POLLEN OF ALNUS-GLUTINOSA, BETULA-VERRUCOSA AND PTEROCARYA-FRAXINIFOLIA [J].
MEURER, B ;
WRAY, V ;
WIERMANN, R ;
STRACK, D .
PHYTOCHEMISTRY, 1988, 27 (03) :839-843
[9]   PUTRESCINE AMIDES FROM KNIPHOFIA SPECIES [J].
RIPPERGER, H ;
SCHREIBE.K ;
BUDZIKIE.H .
JOURNAL FUR PRAKTISCHE CHEMIE-PRACTICAL APPLICATIONS AND APPLIED CHEMISTRY, 1970, 312 (03) :449-+
[10]   VERBASCENINE, A MACROCYCLIC SPERMINE ALKALOID ISOLATING FROM VERBASCUM .184. NATURALLY-OCCURING ORGANIC-SUBSTANCES [J].
SEIFERT, K ;
JOHNE, S ;
HESSE, M .
HELVETICA CHIMICA ACTA, 1982, 65 (08) :2540-2547