New quinone sulfates from the crinoids Tropiometra afra macrodiscus and Oxycomanthus japonicus.
Quinone pigments in the crinoids were investigated. New quinone sulfates 1 and 3 were isolated from Tropiometra afra macrodiscus and Oxycomanthus japonicus, respectively. The structures 1 and 3 were determined to be 1,6,8-trihydroxy-3-propylanthraquinone-2-carboxylic acid 6-O-sulfate (ptilometric acid 6-O-sulfate) and 2-butanoyl-3,6,8-trihydroxy-1,4-naphtoquinone 6-O-sulfate, respectively, by chemical and spectroscopic analysis. Ptilometric acid 6-O-sulfate (1) showed an antifeedant activity on fish.
Takahashi
Daizo
D
Kyoto Pharmaceutical University, Kyoto, Japan.
Maoka
Takashi
T
Tsushima
Miyuki
M
Fujitani
Kazuyoshi
K
Kozuka
Mutsuo
M
Matsuno
Takao
T
Shingu
Tetsuro
T
D000818:Animals; D000880:Anthraquinones / Q000302:isolation & purification* / Q000494:pharmacology; D004447:Echinodermata / Q000737:chemistry*; D005247:Feeding Behavior / Q000187:drug effects; D005399:Fishes; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011809:Quinones / Q000302:isolation & purification* / Q000494:pharmacology; D013329:Structure-Activity Relationship
D000880:Anthraquinones; D011809:Quinones; C474094:ptilometric acid 6-O-sulfate