Narcissus alkaloids part 26 -: Alkaloids from Narcissus angustifolius subsp transcarpathicus (Amaryllidaceae)

被引:49
作者
Labraña, J
Machocho, AK
Kricsfalusy, V
Brun, R
Codina, C
Viladomat, F
Bastida, J
机构
[1] Univ Barcelona, Fac Farm, Dept Nat Prod, E-08028 Barcelona, Spain
[2] Uzhgorod State Univ, Dept Bot, Lab Plant Populat, UA-294000 Uzhgorod, Ukraine
[3] Swiss Trop Inst, Protozool Lab, CH-4002 Basel, Switzerland
关键词
Narcissus angustifolius subsp transcarpathicus; Amaryllidaceae; bulbs; alkaloids; pseudolycorine; 8-O-demethylhomolycorine; cherylline; ungeremine; vasconine; pancracine; nangustine; antiprotozoal activity;
D O I
10.1016/S0031-9422(02)00154-1
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
Seven alkaloids have been isolated from fresh bulbs of Narcissus angustifolius subsp. transcarpathicus (Amaryllidaceae). Nangustine, reported here for the first time, is the first 5,11-methanomorphanthridine alkaloid with a C-3/C-4 substitution. The structure and stereochemistry of this new alkaloid, as well as those previously known, have been determined by physical and spectroscopic methods. Spectroscopic data of pancracine have been completed. The in vitro assay activity against the parasitic protozoa Trypanosoma brucei rhodesiense, Trypanosoma cruzi, Leishmania donovani and Plasmodium falciparum was carried out with the compounds nangustine and pancracine. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:847 / 852
页数:6
相关论文
共 23 条
[1]   PHYTOCHEMICAL INVESTIGATION OF HIPPEASTRUM-VITTATUM .4. STEREOCHEMISTRY OF PANCRACINE, THE 1ST 5,11-METHANOMORPHANTHRIDINE ALKALOID FROM HIPPEASTRUM - STRUCTURE OF HIPPAGINE [J].
ALI, AA ;
MESBAH, MK ;
FRAHM, AW .
PLANTA MEDICA, 1984, 50 (02) :188-189
[2]   CULTIVATION IN A SEMI-DEFINED MEDIUM OF ANIMAL INFECTIVE FORMS OF TRYPANOSOMA-BRUCEI, TRYPANOSOMA-EQUIPERDUM, TRYPANOSOMA-EVANSI, TRYPANOSOMA-RHODESIENSE AND T-GAMBIENSE [J].
BALTZ, T ;
BALTZ, D ;
GIROUD, C ;
CROCKETT, J .
EMBO JOURNAL, 1985, 4 (05) :1273-1277
[3]  
Bastida J, 1998, STUD NAT PROD CHEM, V20, P323
[4]   Alkaloids from Hippeastrum solandriflorum [J].
Bastida, J ;
Codina, C ;
Porras, CL ;
Paiz, L .
PLANTA MEDICA, 1996, 62 (01) :74-75
[5]   H-1 AND C-13 ASSIGNMENTS FROM SENSITIVITY-ENHANCED DETECTION OF HETERONUCLEAR MULTIPLE-BOND CONNECTIVITY BY 2D MULTIPLE QUANTUM NMR [J].
BAX, A ;
SUMMERS, MF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (08) :2093-2094
[6]   SENSITIVITY-ENHANCED TWO-DIMENSIONAL HETERONUCLEAR SHIFT CORRELATION NMR-SPECTROSCOPY [J].
BAX, A ;
SUBRAMANIAN, S .
JOURNAL OF MAGNETIC RESONANCE, 1986, 67 (03) :565-569
[7]  
Chen JZ, 1997, PROG NAT SCI, V7, P329
[8]   Total syntheses of (±)-cherylline and (±)-latifine [J].
Couture, A ;
Deniau, E ;
Lebrun, S ;
Grandclaudon, P .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (07) :789-794
[9]   CIRCULAR DICHROISM STUDIES .I. A QUADRANT RULE FOR OPTICALLY ACTIVE AROMATIC CHROMOPHORE IN RIGID POLYCYCLIC SYSTEMS [J].
DEANGELIS, GG ;
WILDMAN, WC .
TETRAHEDRON, 1969, 25 (20) :5099-+
[10]   CHEMICAL-CONSTITUENTS OF AMARYLLIDACEAE .26. THE ROLE OF UNGEREMINE IN THE GROWTH-INHIBITING AND CYTO-TOXIC EFFECTS OF LYCORINE - EVIDENCE AND SPECULATION [J].
GHOSAL, S ;
SINGH, SK ;
KUMAR, Y ;
UNNIKRISHNAN, S ;
CHATTOPADHYAY, S .
PLANTA MEDICA, 1988, (02) :114-116