GUAIANOLIDES FROM TANACETUM-ANNUUM

被引：14

作者：

BARRERO, AF

SANCHEZ, JF

MOLINA, J

BARRON, A

SALAS, MD

机构：

[1] Department of Organic Chemistry, Faculty of Sciences, University of Granada

来源：

PHYTOCHEMISTRY | 1990年 / 29卷 / 11期

关键词：

Compositae; conformational analysis; guaianolides; molecular mechanics; Tanacetum annuum;

D O I：

10.1016/0031-9422(90)85279-O

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：

Five new guaianolides, in addition to four known guaianolides, have been isolated from extracts of the flowers of Tanacetum annuum. Structures and stereochemistries were elucidated from spectral data and chemically confirmed by correlations with α-santonin and mutual interconversions. Conformational and configurational analysis performed through the molecular mechanics calculations corroborate those obtained by JH,H values and NOEDIF experiments. Evidence for the possibility that the dehydrated lactones are artefacts was obtained. © 1990.

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页码：3575 / 3580

页数：6

相关论文

共 16 条

[1]

[Anonymous], 1982, ACS MONOGRAPH

[2] FULVENE LACTONES FROM TANACETUM-ANNUUM [J].

BARRERO, AF ;

SANCHEZ, JF ;

ZAFRA, MJ ;

BARRON, A ;

FELICIANO, AS .

PHYTOCHEMISTRY, 1987, 26 (05) :1531-1533

[3] INVESTIGATION OF COMPLEX NETWORKS OF SPIN-SPIN COUPLING BY TWO-DIMENSIONAL NMR [J].

BAX, A ;

FREEMAN, R .

JOURNAL OF MAGNETIC RESONANCE, 1981, 44 (03) :542-561

[4] NATURALLY-OCCURRING TERPENE DERIVATIVES .407. 4 GUAIANOLIDES, A EUDESMANOLIDE AND A GERMACRANOLIDE FROM URSINIA-SAXATILIS [J].

BOHLMANN, F ;

BORTHAKUR, N ;

JAKUPOVIC, J ;

PICKARD, J .

PHYTOCHEMISTRY, 1982, 21 (06) :1357-1360

[5] NATURALLY-OCCURRING TERPENE DERIVATIVES .395. GUAIANOLIDES AND FURANOSESQUITERPENES FROM URSINIA-NANA [J].

BOHLMANN, F ;

GUPTA, RK .

PHYTOCHEMISTRY, 1982, 21 (06) :1309-1312

[6]

BOHLMANN F, 1982, PHYTOCHEMISTRY, V18, P995

[7] SYNTHESIS OF 1-EPICYCLOCOLORENONE AND STEREOCHEMISTRY OF CYCLOCOLORENONE [J].

BUCHI, G ;

KAUFFMAN, JM ;

LOEWENTH.HJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (14) :3403-&

[8] PYRIDINE-INDUCED SOLVENT SHIFTS IN NUCLEAR MAGNETIC RESONANCE SPECTRA OF HYDROXYLIC COMPOUNDS [J].

DEMARCO, PV ;

FARKAS, E ;

DODDRELL, D ;

MYLARI, BL ;

WENKERT, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (20) :5480-&

[9] THE RELATIONSHIP BETWEEN PROTON-PROTON NMR COUPLING-CONSTANTS AND SUBSTITUENT ELECTRONEGATIVITIES .1. AN EMPIRICAL GENERALIZATION OF THE KARPLUS EQUATION [J].

HAASNOOT, CAG ;

DELEEUW, FAAM ;

ALTONA, C .

TETRAHEDRON, 1980, 36 (19) :2783-2792

[10]

JAIME C, QCPE, P461