Neodictyoprolenol and Dictyoprolenol, the Possible Biosynthetic Intermediates of Dictyopterenes, in the Japanese Brown Algae Dictyopteris

Neodictyoprolenol [(-)-(3 S )-(1,5 Z, 8Z)-undecatrien-3-ol] and dictyoprolenol [ (-) - ( 3 S ) - (1,5 Z , 8Z )-undecadien-3-ol]), which had been proposed as possible biosynthetic intermediates of the sex pheromones of marine brown algae such as dictyopterene B [(-)-trans-1- ((1'E,3' Z )-hexadienyl)-2-vinylcyclopropane], D ' [(+ )-6 -((1' Z )-butenyl)-1,4 -cycloheptadiene] and C' [(+ )-6-butyl-1,4-cycloheptadiene], were again identified in the essential oils from Dictyopteris prolifera, D. latiscula, and in D. undulata, together with the C11-related volatile compounds such as neodictyoprolene, dictyoprolene and dictyopterenes. Incubation of D. prolifela preparation with racemic neodictyoprolenol and dictyoprolenol as substrates showed (S)-enantioselective decreases of the added substrates and increases in dictyopterenes. From these results, a possible pathway to form dictyopterenes is discussed.