The molecular structures of two melampolides

被引:1
作者
Castañeda-Acosta, J [1 ]
Malcolm, AJ [1 ]
Fronczek, FR [1 ]
Fischer, NH [1 ]
机构
[1] Louisiana State Univ, Dept Chem, Baton Rouge, LA 70803 USA
基金
美国国家科学基金会;
关键词
melampolides; sesquiterpene lactones;
D O I
10.1023/A:1009539802465
中图分类号
O7 [晶体学];
学科分类号
0702 ; 070205 ; 0703 ; 080501 ;
摘要
The melampolide-class sesquiterpene lactone 11 beta H,13-dihydro-14-hydroxy-(1,10)-cis-parthenolide, C15H22O4, 1, crystallizes in orthorhombic space group P2(1)2(1)2(1), with a = 7.435(2), b = 12.678(2), c = 14.991(2) Angstrom, V = 1413.1(8) Angstrom(3) and Z = 4. The aldehyde analog, C15H20O4. H2O 2, crystallizes as the monohydrate in orthorhombic space group P2(1)2(1)2(1), with a = 9.061(2), b = 9.295(2), c = 17.761(4) Angstrom, V = 1495.8(9) Angstrom(3), and Z = 4. The 10-membered rings of the two molecules adopt approximate chair-boat conformations. In both compounds, the double bond at C1-C10 position of the cyclodecene ring is Z, while the C4-C5 is epoxidized with an E-configuration. The C15 methyl is beta and H5 is alpha. The lactone ring is trans fused at the C6 and C7 positions to the 10-membered ring. The C13 methyl group has an alpha orientation in both molecules.
引用
收藏
页码:111 / 114
页数:4
相关论文
共 10 条
[1]   The molecular structures of three germacrolides related to parthenolide [J].
Castaneda-Acosta, J ;
Pentes, HG ;
Fronczek, FR ;
Fischer, NH .
JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 1997, 27 (11) :635-639
[2]  
FAIR CK, 1990, MOLEN INTERACTIVE ST
[3]  
Fischer N. H., 1979, Progress in the chemistry of organic natural products. Volume 38., P47
[4]  
FISCHER NH, 1990, BIOCH MEVALONIC ACID, V24, P161
[5]   STRUCTURE OF LONGIPILIN [J].
FRONCZEK, FR ;
VARGAS, D ;
FISCHER, NH .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1986, 42 :1061-1063
[6]   THE MOLECULAR-STRUCTURE OF MELAMPODININ-A [J].
FRONCZEK, FR ;
MALCOLM, A ;
FISCHER, NH .
JOURNAL OF NATURAL PRODUCTS, 1983, 46 (02) :170-173
[7]  
MAIN P, 1978, MULTAN78 SYSTEM COMP
[8]  
RYCHLEWSKA U, COLLECT CZECH CHEM C, V51, P1698
[9]   SYSTEMATIC IMPLICATIONS OF SESQUITERPENE LACTONES IN THE SUBTRIBE MELAMPODIINAE [J].
SEAMAN, FC ;
FISCHER, NH ;
STUESSY, TF .
BIOCHEMICAL SYSTEMATICS AND ECOLOGY, 1980, 8 (03) :263-271
[10]  
UMBREIT MA, 1979, CHEM LETT, P1503