Pigments of marine animals. XI. Angular naphthopyrones from the crinoid Comanthus parvicirrus timorensis

Abstract

Green specimens of the comatulid crinoid, Comanthus parvicirrus timorensis J. Muller, yield to acetone three yellow water-soluble colouring matters, comaparvin sulphate, 6-methoxycomaparvin sulphate, and 6-methoxycomaparvin 5-methyl ether sulphate in approximately 0.1 %, 0.7 %, and 0.7 % yield respectively of the dry weight of the animal, Mild acid hydrolysis yields the corresponding phenols, the structures of which have been deduced largely by spectral studies as very probably 5,8-dihydroxy-10-methoxy-2-n-propyl-4H-naphtho[1,2-b]pyran-4-one (1), the 6-methoxy derivative of (1), and the 6-methoxy methyl ether of (1) respectively. A yellow colour variant of the same species yielded the same colouring matters in slightly different proportions. The calcareous skeleton contains what are probably polyhydroxynaphthoquinones in combined form.