Mikanolide from Jamaican Mikania micrantha.
Mikanolide [systematic names: 1,10:2,3-diepoxy-6,8-dihydroxy-11-vinylgermacr-4-ene 12,14-di-gamma-lactone and 7,10a-dimethyl-1a,1b,2a,6a,7,9a,10,10a-octahydro-4H-6,3-methenofuro[3,2-c]bisoxireno[f,h]oxacycloundecin-4,8(6H)-dione], C(15)H(14)O(6), derived from a variety of Mikania micrantha growing in Portland, Jamaica, contains a methylcyclodecane ring fused to an unsaturated planar alpha,gamma-lactone, an envelope-type near-planar vinyl-beta,gamma-lactone and two epoxide moieties. The crystal packing shows stacks of mikanolide molecules interlocked via a network of non-classical C-H...O hydrogen bonds between the lactone units.
Bakir
Mohammed
M
Department of Chemistry, The University of the West Indies, Mona Campus, Kingston 7, Jamaica. mohammed.bakir@uwimona.edu.jm
Facey
Petrea C
PC
Hassan
Ishmael
I
Mulder
Willem H
WH
Porter
Roy B
RB
D000890:Anti-Infective Agents / Q000737:chemistry; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry; D018360:Crystallography, X-Ray; D004970:Estrone / Q000031:analogs & derivatives* / Q000737:chemistry*; D006860:Hydrogen Bonding; D007563:Jamaica; D007783:Lactones / Q000737:chemistry*; D035742:Mikania / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D045788:Sesquiterpenes, Germacrane
C500662:1,10:2,3-diepoxy-6,8-dihydroxy-11-vinylgermacr-4-ene 12,14-di-gamma-lactone; C500664:3-benzyloxy-16-((N-methyl-N-phenylamino)methylidene)estra-1,3,5(10)-trien-17-one; D000890:Anti-Infective Agents; D000972:Antineoplastic Agents, Phytogenic; D007783:Lactones; D045788:Sesquiterpenes, Germacrane; D004970:Estrone