LITHOSPERMOSIDE AND DASYCARPONIN, CYANOGLUCOSIDES FROM THALICTRUM

被引:23
作者
WU, J
FAIRCHILD, EH
BEAL, JL
TOMIMATSU, T
DOSKOTCH, RW
机构
[1] Division of Pharmacognosy and Natural Products Chemistry, College of Pharmacy, Ohio State University, Columbus
来源
JOURNAL OF NATURAL PRODUCTS | 1979年 / 42卷 / 05期
关键词
D O I
10.1021/np50005a011
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Two cyanoglucosides from Thalictrum are assigned structures by physical and chemical methods. The glycoside from T. rugosum and T. revolutum is identical with lithospermoside and griffonin. Its absolute stereochemistry was determined as in 1 from circular dichroism studies with the dibenzoate of the modified aglycone, griff onilide (2). The other glycoside, dasycarponin (5), from T. dasycarpum is the 4-epimer of lithospermoside. Proton and carbon nuclear magnetic resonances, circular dichroism and other spectral data are given for these compounds and their products. © 1979, American Chemical Society. All rights reserved.
引用
收藏
页码:500 / 511
页数:12
相关论文
共 20 条
[1]   PROTON RESONANCE STUDY OF CONFORMATIONS OF CARBOHYDRATES IN SOLUTION.1. DERIVATIVES OF 1,2-O-ISOPROPYLIDENE-ALPHA-D-XYLOHEXOFURANOSE [J].
ABRAHAM, RJ ;
HALL, LD ;
MCLAUCHLAN, KA ;
HOUGH, L .
JOURNAL OF THE CHEMICAL SOCIETY, 1962, (SEP) :3699-&
[2]   PROTON MAGNETIC RESONANCE SPECTRA AND CONFORMATIONS OF CYCLIC COMPOUNDS .2. PMR SPECTRA OF CONDURITOLS [J].
ABRAHAM, RJ ;
GOTTSCHA.H ;
PAULSEN, H ;
THOMAS, WA .
JOURNAL OF THE CHEMICAL SOCIETY, 1965, (NOV) :6268-&
[3]   ALLYLIC INTER-PROTON SPIN-SPIN COUPLING [J].
BARFIELD, M ;
SPEAR, RJ ;
STERNHELL, S .
CHEMICAL REVIEWS, 1976, 76 (05) :593-624
[4]   CD OF ALPHA-BETA-UNSATURATED LACTONES [J].
BEECHAM, AF .
TETRAHEDRON, 1972, 28 (22) :5543-+
[5]   INFLUENCE OF ALLYLIC OXYGEN ON PI-]PI] CD OF CERTAIN CHROMOPHORES [J].
BEECHAM, AF .
TETRAHEDRON, 1971, 27 (21) :5207-&
[6]   INFLUENCE OF ALLYLIC OXYGEN ON CD OF SKEW DIENES [J].
BEECHAM, AF ;
MATHIESO.AM ;
JOHNS, SR ;
LAMBERTO.JA ;
SIOUMIS, AA ;
BATTERHA.TJ ;
YOUNG, IG .
TETRAHEDRON, 1971, 27 (16) :3725-&
[7]   SIMPLIFIED C-13 SPECTRAL ASSIGNMENTS USING A GRAPHICAL METHOD TO PRESENT C-13 SPECTRA RECORDED UNDER CONDITIONS OF PROTON OFF-RESONANCE SPIN DECOUPLING [J].
BIRDSALL, B ;
BIRDSALL, NJ ;
FEENEY, J .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1972, (06) :316-&
[8]  
DWUMABADU D, 1976, LLOYDIA, V39, P385
[9]   SIMMONDSIN, AN UNUSUAL 2-CYANOMETHYLENECYCLOHEXYL GLUCOSIDE FROM SIMMONDSIA-CALIFORNICA [J].
ELLIGER, CA ;
WAISS, AC ;
LUNDIN, RE .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (19) :2209-2212
[10]   CONFORMATIONS .6. VINYL-ALLYLIC PROTON SPIN COUPLINGS [J].
GARBISCH, EW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (24) :5561-+