EPIMERIC (20R,20S)-VERAZINE ISOLATED FROM VERATRUM-MAACKII - 2-DIMENSIONAL NMR-STUDIES AND TOTAL ASSIGNMENT OF H-1-RESONANCES AND C-13-RESONANCES

被引:17
作者
HAN, XW [1 ]
RUEGGER, H [1 ]
机构
[1] SPECTROSPIN AG,CH-8117 FALLANDEN,SWITZERLAND
关键词
VERATRUM-MAACKII; VERAZINE; STEREOCHEMICAL ELUCIDATION; NMR SPECTROSCOPY;
D O I
10.1055/s-2006-961511
中图分类号
Q94 [植物学];
学科分类号
071001 [植物学];
摘要
C-13-NMR evidence shows that verazine [(25S)-iminocholesta-5,22(N)-diene-3beta-ol] isolated from the Chinese plant Veratrum maackii (Melanthiaceae) consists of a 20R/20S mixture of epimers. The determination of the configurations at the chiral epimeric center and of the conformation of the 17beta-side chain is based on the total assignment of the C-13- and H-1-NMR resonances. This goal was achieved by the extensive use of homo- and heteronuclear shift correlation and two-dimensional NOE spectroscopy methods at high magnetic field.
引用
收藏
页码:449 / 453
页数:5
相关论文
共 18 条
[1]
VERAZIN EIN NEUES VERATRUM-ALKALOID MIT 22,26-IMINO-CHOLESTAN-GERUST [J].
ADAM, G ;
SCHREIBE.K ;
TOMKO, J ;
VASSOVA, A .
TETRAHEDRON, 1967, 23 (01) :167-&
[2]
ASSIGNMENT OF THE C-13 NMR-SPECTRA OF SOME 22,26-EPIMINOCHOLESTANES, 22,26-EPIMINOCHOLEST-22(N)-ENES AND SOME 3-BETA-AMINO STEROIDAL ALKALOIDS [J].
BIRD, GJ ;
COLLINS, DJ ;
EASTWOOD, FW ;
EXNER, RH .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1979, 32 (04) :797-816
[3]
C-13 NMR-STUDIES .69. C-13 NMR-SPECTRA OF STEROIDS - SURVEY AND COMMENTARY [J].
BLUNT, JW ;
STOTHERS, JB .
ORGANIC MAGNETIC RESONANCE, 1977, 9 (08) :439-464
[4]
INVESTIGATION OF EXCHANGE PROCESSES BY 2-DIMENSIONAL NMR-SPECTROSCOPY [J].
JEENER, J ;
MEIER, BH ;
BACHMANN, P ;
ERNST, RR .
JOURNAL OF CHEMICAL PHYSICS, 1979, 71 (11) :4546-4553
[5]
BIOSYNTHESIS OF RUBIJERVINE IN VERATRUM-GRANDIFLORUM [J].
KANEKO, K ;
SETO, H ;
MOTOKI, C ;
MITSUHASHI, H .
PHYTOCHEMISTRY, 1975, 14 (5-6) :1295-1301
[6]
CONTACT ELECTRON-SPIN COUPLING OF NUCLEAR MAGNETIC MOMENTS [J].
KARPLUS, M .
JOURNAL OF CHEMICAL PHYSICS, 1959, 30 (01) :11-15
[7]
ASSIGNMENT OF CARBONYL CARBONS AND SEQUENCE-ANALYSIS IN PEPTIDES BY HETERONUCLEAR SHIFT CORRELATION VIA SMALL COUPLING-CONSTANTS WITH BROAD-BAND DECOUPLING IN T1 (COLOC) [J].
KESSLER, H ;
GRIESINGER, C ;
ZARBOCK, J ;
LOOSLI, HR .
JOURNAL OF MAGNETIC RESONANCE, 1984, 57 (02) :331-336
[8]
Kupchan S. M., 1968, ALKALOIDS, V10, P193
[9]
LIANG G, 1985, YAOXUE XUEBAO, V19, P309
[10]
APPLICATION OF PHASE SENSITIVE TWO-DIMENSIONAL CORRELATED SPECTROSCOPY (COSY) FOR MEASUREMENTS OF H-1-H-1 SPIN-SPIN COUPLING-CONSTANTS IN PROTEINS [J].
MARION, D ;
WUTHRICH, K .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1983, 113 (03) :967-974