Structures of new amphidinols with truncated polyhydroxyl chain and their membrane-permeabilizing activities.
Two new homologues of amphidinols (AM14 and AM15) were isolated from the cultured dinoflagellate Amphidinium klebsii. The structures were elucidated on the basis of 2D NMR and collision-induced dissociation MS/MS and turned out to be closely related homologues of AM7. Their weak membrane-disrupting activity indicates that the hydrophobic polyene chain is essential for the potent biological activities. Structure-activity relationship for the polyhydroxyl part was then examined with use of AM homologues possessing various chain lengths, indicating that the pore size of the channel/lesion formed by AMs was not greatly affected by the length of the polyhydroxyl chain.
Morsy
Nagy
N
Department of Chemistry, Graduate School of Science, Osaka University, Machikaneyama, Toyonaka, Osaka 560-0043, Japan.
Houdai
Toshihiro
T
Matsuoka
Shigeru
S
Matsumori
Nobuaki
N
Adachi
Seiji
S
Oishi
Tohru
T
Murata
Michio
M
Iwashita
Takashi
T
Fujita
Tsuyoshi
T
D000475:Alkenes / Q000138:chemical synthesis* / Q000494:pharmacology*; D000818:Animals; D000935:Antifungal Agents / Q000737:chemistry / Q000494:pharmacology; D001230:Aspergillus / Q000187:drug effects; D002463:Cell Membrane Permeability / Q000187:drug effects*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D004141:Dinoflagellida / Q000737:chemistry*; D004912:Erythrocytes / Q000187:drug effects; D005658:Fungi / Q000187:drug effects; D006461:Hemolysis / Q000187:drug effects; D006801:Humans; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008826:Microbial Sensitivity Tests; D011714:Pyrans / Q000138:chemical synthesis* / Q000494:pharmacology*; D021241:Spectrometry, Mass, Electrospray Ionization; D013056:Spectrophotometry, Ultraviolet; D013329:Structure-Activity Relationship
D000475:Alkenes; D000935:Antifungal Agents; D011714:Pyrans