Structure-activity relationship of polyisoprenyl benzophenones from Garcinia pyrifera on the tubulin/microtubule system.
Microtubule disassembly inhibitory properties have been established for the known polyisoprenylated benzophenones xanthochymol (1a) and guttiferone E (1b). The compounds were isolated from the fruits of Garcinia pyrifera collected in Malaysia. A structure-activity relationship study, including natural and semisynthetic derivatives, delineated some structural features necessary for the interaction with tubulin within this compound class.
Roux
D
D
Institut de Chimie des Substances Naturelles, Centre National de la Recherche Scientifique, 91198 Gif-sur-Yvette Cedex, France.
Hadi
H A
HA
Thoret
S
S
Guénard
D
D
Thoison
O
O
Païs
M
M
Sévenet
T
T
D001577:Benzophenones / Q000737:chemistry / Q000494:pharmacology*; D002070:Butadienes / Q000737:chemistry / Q000494:pharmacology*; D002850:Chromatography, Gel; D002851:Chromatography, High Pressure Liquid; D005638:Fruit / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry; D045782:Hemiterpenes; D006801:Humans; D007624:KB Cells / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008296:Malaysia; D008870:Microtubules / Q000187:drug effects*; D009904:Optical Rotation; D010420:Pentanes; D010946:Plants, Medicinal / Q000737:chemistry*; D019685:Rosales / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013329:Structure-Activity Relationship; D014404:Tubulin / Q000032:analysis / Q000096:biosynthesis
D001577:Benzophenones; D002070:Butadienes; D045782:Hemiterpenes; D010420:Pentanes; D014404:Tubulin; C005059:isoprene; C414432:xanthochymol; C414433:guttiferone E