Isolation and identification of a cis-C8-diol-ester of okadaic acid from Dinophysis acuta in New Zealand.
A cis-isomer of a C(8)-diol ester of okadaic acid (1) was isolated during large-scale purification of pectenotoxins (PTXs) from extracts of Dinophysis acuta collected from the west coast of South Island, New Zealand. The compound was identified by NMR spectroscopic and liquid chromatography-mass spectrometry (LC-MS) studies, and is the first reported cis-isomer of an okadaic acid C(8)-diol-ester identified in Dinophysis. The more abundant trans-C(8)-diol ester of okadaic acid (2) isolated from the same Dinophysis extract was rapidly hydrolyzed to okadaic acid in vitro by the supernatant from green-lipped mussel hepatopancreas.
Miles
Christopher O
CO
AgResearch Ltd., Ruakura Research Centre, Private Bag 3123, Hamilton, New Zealand. chris.miles@agresearch.co.nz
Wilkins
Alistair L
AL
Hawkes
Allan D
AD
Jensen
Dwayne J
DJ
Cooney
Janine M
JM
Larsen
Kristofer
K
Petersen
Dirk
D
Rise
Frode
F
Beuzenberg
Veronica
V
Lincoln Mackenzie
A
A
D000818:Animals; D002851:Chromatography, High Pressure Liquid; D004141:Dinoflagellida / Q000737:chemistry*; D004951:Esterification; D005663:Furans / Q000494:pharmacology; D043143:Hepatopancreas / Q000378:metabolism; D006868:Hydrolysis / Q000187:drug effects; D018942:Macrolides; D009682:Magnetic Resonance Spectroscopy; D008387:Marine Toxins / Q000737:chemistry / Q000302:isolation & purification*; D015394:Molecular Structure; D019319:Okadaic Acid / Q000031:analogs & derivatives / Q000032:analysis / Q000302:isolation & purification*; D011714:Pyrans / Q000737:chemistry* / Q000494:pharmacology; D021241:Spectrometry, Mass, Electrospray Ionization; D000095702:Polyether Toxins
D005663:Furans; D018942:Macrolides; D008387:Marine Toxins; D019319:Okadaic Acid; D011714:Pyrans; C051904:dinophysistoxin 1; C098380:pectenotoxin 2; D000095702:Polyether Toxins