Molluscs compounds from

The thiazoline and thiazole rings are present in many cyclic peptides isolated from marine organisms. Most of these types of compound have been isolated from tunicates belonging to the Lissoclinum and Didemnum genus, from sponges of the genus Theonella, and from the sea hare mollusc Dolabella auricularia. The isolation of closely related compounds from cyanobacteria pointed out the symbiont origin of these metabolites. 

Murexine and related compounds have marked actions on the nicotine receptor as expected from choline esters (87-89). Toxins from the digestive glands of nudi-branchs have marked effects on the cardiovascular system of the rat (23). Antiviral and antibacterial substances have been obtained from molluscs (90,91). 

The studies on the biosynthetic origin of secondary metabolites in marine molluscs are reviewed. Although the majority of natural products found in marine molluscs appears to have a dietary origin, de novo biosynthetic ability towards particular classes of compounds has been demonstrated. Marine molluscs are also able to modify metabolites sequestered from their specific prey. 

The scope of the majority of the papers is limited to the ascertainment of the existence of de novo biosynthesis of a particular compound. In this respect it has recently been proposed that in many cases it would be possible to predict the origin of secondary metabolites in nudibranch molluscs by examining their geographical variations in a given species [10]. Those molluscs that exhibit considerable variation in their chemical constituents undoubtedly obtain these from dietary sources, while those that have the same substances wherever they are collected are most likely capable of de novo biosynthesis. 

The presence in molluscs of molecules structurally related to typical dietary metabolites could be ascribed either to selective accumulation of minor compounds acquired through the diet, or to an in vivo chemical transformation of major metabolites acquired from the prey. However, all reports on this topic have to be carefully evaluated before drawing hurried conclusions. In particular, interaction among molecules from different organs could favor formation of artifacts when the secondary metabolites are extracted from the whole mollusc and not from individual dissected tissues. Only some cases, where the ability of the molluscs to modify dietary metabolites seems to be well supported, are reported in this chapter. 

While little biosynthetic information is available, it has been suggested [38] that 25 and 26 may be formed from AA (24) and EPA (14) via a cyclization mechanism (Scheme 3) similar to that which forms trans-cyclopropyl-containing diol 28 upon treatment of linoleic acid with performic acid [40]. An alternative biogenetic mechanism (Scheme 4), based upon that proposed for the structurally related red algal metabolites constanolactone A and B [41], would involve the formation and opening of an allylic epoxide intermediate created as a result of a 15-/ -LPO acting on either AA or EPA. Related compounds have been isolated from the coral Plexaura homomalla and the mollusc Aplysia kurodai (see below). 

Di Marzo V, Cimino G, Sodano G, Spinella A, Villani G, A novel prostaglandin metabolic pathway from a marine mollusc prostaglandin 1,15-lactones. 7th Internation Conf, on Prostaglandins and related compounds, 28 May-1 June 1990, Florence, Italy, p 13... 

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