Lissoclinum tunicate

A sulfone (636) is a minor constituent of the Mediterranean sponge Anchinoe tenacior [502]. Sulfolane (637), a familiar industrial chemical, was isolated from a mixture of the sponge Batzella sp. and a Lissoclinum tunicate from Victoria, Australia [503]. It is possibly an absorbed compound rather than a natural product [12]. 

Nitrogenous compounds are so abundant, especially in the genus Lissoclinum, diat in 1990 Davidson and Ireland produced a publication titled Lissodinolide, the first non-nitrogenous metabolite from a Lissoclinum tunicate. ... 

Lissoclinum species of tunicates produce a range of cyclic peptides, which contain thiazole, thiazoline and oxazoline rings. Most belong to the general families patellamides (octapeptides), lissoclinamides (heptapeptides) or bistratamides (hexapeptides) [22],... 

The heptapeptide ulicyclamide (15) and the octapeptide ulithiacyclamide (16) were the first representatives of a series of cyclic peptides to be isolated from Lissoclinum patella. Their structures were elucidated by interpretation of spectral data [44], A revised structure was later put forward for ulicyclamide (15) as a result of a detailed analysis of the fast atom bombardment (FAB) mass spectrum. The same paper reported the isolation of two more polar cyclic peptides and another, which was present as a minor component. These heptapeptides were called lissoclinamides 1-3 (17-19) [45]. An unidentified tunicate from the Great Barrier Reef contained ulithiacyclamide (16) and ascidiacyclamide (14) [46]. Two syntheses of ulithiacyclamide (16)... 

A series of sulfur-containing dopamine-derived metabolites has been isolated from tunicates, predominantly belonging to the genus Lissoclinum. 

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. 

A series of macrolides bearing a thiazole moiety have been isolated from tunicates and sponges. The tunicate Lissoclinum patella has afforded the patellazoles A-C (428-430), which were found to be potent cytotoxins in the NCI human cell line protocol with mean IC50 values of 10-3—10-6 pg/ml as well as exhibiting antifungal activity [334, 335]. Furthermore, patellazole B (429) exhibited very potent antiviral activity against Herpes symplex viruses [334],... 

Bistramide A (C H Og) was isolated from the tunicate Lissoclinum bistratum collected at New Caledonia and shown to possess neuro- and cytotoxic activity. Although extensive two-dimensional NMR studies were used, its complete structure remains to be established (238). 

Two cyclic peptides that were isolated from the marine tunicate Lissoclinum patella,30 named ulicyclamide and ulithiacyclamide, have structures (33) and (34). 

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... 

The cyclamides are small cyclic peptides that characteristically contain multiple thiazole, thiazoline, oxazole, and oxazoline rings, which are derived from cysteine, serine, and threonine residues. Some of the first examples of this class to be described were the patellamides (53-55) from the tunicate Lissoclinum patella, although it was later determined they were produced by the symbiotic cyanobacterium Prochloron sp. The structures were solved by a combination of acid hydrolysis and GC analysis, coupled with 2D NMR. Smaller cyclic peptides from this class include the hexapeptides westiellamide (56) and microcyclamide (57) from M. aeruginosa Many members of the class possess cytotoxic properties, although their biological function or mechanism of action is not fully understood. In contrast to many cyanobacterial peptides, aside from the unusual heterocyclic residues, these peptides generally contain only ribosomal amino acids. 

A review describes the pharmacological properties of l,2-benzisothiazoles. In connection with thiazoles, we find several reviews or papers thiazoles in food aromas patellamides, which are antineoplastic cyclic peptides, from the marine tunicate Lissoclinum patella, which contain an unusual fused oxazoline-thiazole unit and polythiazole-containing peptide antibiotics. An interesting total synthesis of the aglycon of bleomycin A2 should also be mentioned. ... 

Patellazoles A-C (77-79), 24-membered thiazole-containing macrolides, were isolated from two specimens of didemnid tunicate, Lissoclinum patella, which were collected from the Fiji Islands [148] and Piti Bomb Holdes, Guam [149]. The patellazoles were potent cytotoxins in the NCI human cell line protocol with mean IC50 values of 10" to 10 pg/ml and antifungal activity against Candida albicans. 

Corley, D. G., Moore, R. E., and Paul, V. J. (1988). Patellazole B A novel cytotoxic thiazole-containing macrolide from the marine tunicate Lissoclinum patella. J. Am. Chem. Soc. 110, 7920-7922. 

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. 

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

Cyclopeptide from the marine tunicate Lissoclinum patella. Cytotoxic. Amorph. solid, [aj +40 (c, 0.1 in MeOH). 

Wasylyk, J. M., J. E. Biskupiak, C. E. Costello, and C. M. Ireland Cyclic peptide structures from the Tunicate Lissoclinum Patella by FAB mass spectrometry. J. Organ. Chem. (USA) 48, 4445 (1983). 

Cyclic peptides and depsipeptides constitute the bulk of the nitrogenous metabolites of didemnid tunicates and several publications have been devoted to them, either wholly or in part, such as Ireland et al. (1989), Davidson (1993) and Lehrer et al. (2003). However, many publications devoted to cyclic peptides of Didemnidae are concerned with only three species, Didemnum molle, Lissoclinum bistratum and Lissoclinum patella, which is the most prolific didemnid as regards cyclic peptides. The two Lissoclinum species were harvested in the Western Pacific (Australia, Fiji, Guam, Indonesia, Palau, Philippines, Pohnpei and Singapore) and Didemnum molle in the Indian Ocean (Comoros, Mozambique). 

Ireland, C.M., Durso, A.R., Newman, R.A., and Hacker, M.P. (1982) Antineoplastic cyclic peptides from the marine tunicate Lissoclinum patella. J. Org. Chem., 47, 1807-1811. 

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

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