Lissoclinum perforatum

Lissoclinum perforatum (ascidian) Lissoclinum vareau (ascidian) ... 

Chemically related to the trithianes is the benzo-1,2,3-trithiane derivative lissochnotoxin A, shown at the bottom of Table 6. It has been obtained by methanol extraction of the tunicate Lissoclinum perforatum followed by preparative HPLC on Si02, and forms a yellow solidofmp 245-250 In vitro, this material exhibits potent antimicrobial, antifungal, and modest cytotoxic activities. The benzopentathiepin... 

Analogously, lissoclinotoxin A (42) [Fig. (12)], a sulfur-containing alkaloid isolated from the tunicate Lissoclinum perforatum [60], showed high activity against P. falciparum but was later found to be a DNA-damaging agent [61] at very low concentrations and, thus, its use as an antimalarial agent cannot be proposed. 

Lissoclinotoxin A was initially reported [19] as the benzotrithiane (10) but the structure was subsequently corrected [21] to the benzopentathiepin (11). The chirality of such unsymmetrically substituted benzopentathiepins was noted by two authors [14,23] and optical activity has been reported [14]. Lissoclinotoxin A has been reported from Lissoclinum perforatum [19,21] from the Eastern Atlantic where it co-occurred with lissoclinotoxin B (12), and from a Lissoclinum sp. from the Great Barrier Reef (GBR), Australia [14]. 

Minor constit. of the tunicate Lissoclinum perforatum. Exhibits antimicrobial activity. Pale yellow powder. Mp 310-313°. 

I, 2,3-trifhiane derivative from the tunicate Lissoclinum perforatum. Tetrahedron Lett., 32, 911-914. 

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