ISOLATION, STRUCTURAL ELUCIDATION AND CONFORMATIONAL-ANALYSIS OF SESQUITERPENE PYRIDINE ALKALOIDS FROM MAYTENUS-EBENIFOLIA REISS - X-RAY MOLECULAR-STRUCTURE OF EBENIFOLINE-W-I

被引:42
作者
ITOKAWA, H [1 ]
SHIROTA, O [1 ]
MORITA, H [1 ]
TAKEYA, K [1 ]
IITAKA, Y [1 ]
机构
[1] TEIKYO UNIV,FAC MED,HACHIOJI,TOKYO 19203,JAPAN
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 11期
关键词
D O I
10.1039/p19930001247
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The structures of seven novel alkaloids, ebenifolines W-I, W-II, E-I, E-II, E-III, E-IV and E-V, isolated from Maytenus ebenifolia Reiss., were determined by means of H-1 and C-13 NMR spectroscopic studies, mainly 2D experiments, to be sesquiterpene pyridine alkaloids having either a fifteen- or sixteen-membered ring structure. The conformation of one of these alkaloids, ebenifoline W-I 1, was determined by homodecoupling experiments, NOESY spectra in NMR, and X-ray analysis. The flexibility of the two types of macrocyclic ring systems was studied by their T1-values of C-13 NMR spectroscopy.
引用
收藏
页码:1247 / 1254
页数:8
相关论文
共 23 条
  • [1] H-1 AND C-13 ASSIGNMENTS FROM SENSITIVITY-ENHANCED DETECTION OF HETERONUCLEAR MULTIPLE-BOND CONNECTIVITY BY 2D MULTIPLE QUANTUM NMR
    BAX, A
    SUMMERS, MF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (08) : 2093 - 2094
  • [2] Flores F. A., 1984, ADV EC BOTANY, V1, P1
  • [3] CHUCHUHUASHA - A DRUG USED IN FOLK MEDICINE IN THE AMAZONIAN AND ANDEAN AREAS - A CHEMICAL STUDY OF MAYTENUS-LAEVIS
    GONZALEZ, JG
    DELLEMONACHE, G
    DELLEMONACHE, F
    MARINIBETTOLO, GB
    [J]. JOURNAL OF ETHNOPHARMACOLOGY, 1982, 5 (01) : 73 - 77
  • [4] SESQUITERPENE ALKALOIDS FROM EUONYMUS-JAPONICA
    HAN, BH
    PARK, MK
    RYU, JH
    PARK, JH
    NAOKI, H
    [J]. PHYTOCHEMISTRY, 1990, 29 (07) : 2303 - 2307
  • [5] NEW SESQUITERPENE ALKALOIDS FROM EUONYMUS-JAPONICA - STRUCTURES OF EUOJAPONINE-D, EUOJAPONINE-F, EUOJAPONINE-J, AND EUOJAPONINE-K
    HAN, BH
    RYU, JH
    HAN, YN
    PARK, MK
    PARK, JH
    NAOKI, H
    [J]. JOURNAL OF NATURAL PRODUCTS, 1990, 53 (04): : 909 - 914
  • [6] TRITERPENES FROM MAYTENUS-ILICIFOLIA
    ITOKAWA, H
    SHIROTA, O
    IKUTA, H
    MORITA, H
    TAKEYA, K
    IITAKA, Y
    [J]. PHYTOCHEMISTRY, 1991, 30 (11) : 3713 - 3716
  • [7] NEW TRITERPENE DIMERS FROM MAYTENUS-ILICIFOLIA
    ITOKAWA, H
    SHIROTA, O
    MORITA, H
    TAKEYA, K
    TOMIOKA, N
    ITAI, A
    [J]. TETRAHEDRON LETTERS, 1990, 31 (47) : 6881 - 6882
  • [8] SESQUITERPENE PYRIDINE ALKALOIDS FROM MAYTENUS-EBENIFOLIA
    ITOKAWA, H
    SHIROTA, O
    MORITA, H
    TAKEYA, K
    [J]. HETEROCYCLES, 1992, 34 (05) : 885 - 889
  • [9] TUMOR INHIBITORS .73. MAYTANSINE, A NOVEL ANTILEUKEMIC ANSA MACROLIDE FROM MAYTENUS-OVATUS
    KUPCHAN, SM
    KOMODA, Y
    THOMAS, GJ
    SMITH, RM
    BRYAN, RF
    HALTIWAN.RC
    KARIM, A
    COURT, WA
    GILMORE, CJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (04) : 1354 - +
  • [10] Monache FD, 1984, Z ANGEW ENTOMOL, V97, P406