title: Isolation and identification of a cis-C8-diol-ester of okadaic acid from Dinophysis acuta in New Zealand.
abstract: 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.
authors.affiliation: AgResearch Ltd., Ruakura Research Centre, Private Bag 3123, Hamilton, New Zealand. chris.miles@agresearch.co.nz
authors.forename: Christopher O
authors.initials: CO
authors.lastname: Miles
authors.forename: Alistair L
authors.initials: AL
authors.lastname: Wilkins
authors.forename: Allan D
authors.initials: AD
authors.lastname: Hawkes
authors.forename: Dwayne J
authors.initials: DJ
authors.lastname: Jensen
authors.forename: Janine M
authors.initials: JM
authors.lastname: Cooney
authors.forename: Kristofer
authors.initials: K
authors.lastname: Larsen
authors.forename: Dirk
authors.initials: D
authors.lastname: Petersen
authors.forename: Frode
authors.initials: F
authors.lastname: Rise
authors.forename: Veronica
authors.initials: V
authors.lastname: Beuzenberg
authors.forename: A
authors.initials: A
authors.lastname: Lincoln Mackenzie
mesh_terms: 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
chemical_list: D005663:Furans; D018942:Macrolides; D008387:Marine Toxins; D019319:Okadaic Acid; D011714:Pyrans; C051904:dinophysistoxin 1; C098380:pectenotoxin 2; D000095702:Polyether Toxins