Isolation and structure/activity features of halomon-related antitumor monoterpenes from the red alga Portieria hornemannii.
Ten halogenated monoterpenes (2-6 and 8-12) related to the novel antitumor compound halomon (1) or to the carbocyclic analog 7 have been isolated from different geographic collections of the red alga, Portieria hornemannii. Structures were assigned to the basis of spectral analyses (primarily NMR and MS). The absolute configuration of isohalomon (2) was further established by X-ray crystallography. The compounds were comparatively evaluated alongside 1 and 7 in the U.S. National Cancer Institute's in vitro human tumor cell line screening panel. The results provide some interesting initial insights into the structure/activity relationships in this series.
Fuller
R W
RW
Laboratory of Drug Discovery Research and Development, National Cancer Institute, Frederick, Maryland 21702-1201.
Cardellina
J H
JH
Jurek
J
J
Scheuer
P J
PJ
Alvarado-Lindner
B
B
McGuire
M
M
Gray
G N
GN
Steiner
J R
JR
Clardy
J
J
Menez
E
E
D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002470:Cell Survival / Q000187:drug effects; D003198:Computer Simulation; D018360:Crystallography, X-Ray; D006801:Humans; D006846:Hydrocarbons, Halogenated / Q000737:chemistry* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D000461:Rhodophyta; D013729:Terpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D006846:Hydrocarbons, Halogenated; D013729:Terpenes; C076123:6-bromo-3-(bromomethyl)-7-methyl-2,3,7-trichloro-1-octene