Batzella sponge

Like the prianosins and the discorhabdins, the batzellines and isobatzellines are sulfides with a pyrroloquinone skeleton [22]. A deepwater Batzella sponge contained the alkaloids, batzellines A (457) and B (458), which possess methyl sulfide groups. The structure of... 

Batzelladlnes. Alkaloids with unusual polycyclic structures from the Caribbean Batzella sponges. B. induce P56 -CD4-dissociation (cell cycle). 

Gunaseko-a, S.P. McCarthy, P.J. Longl, R.E. Pomponi, S.A. Wright, A.E. (1999) Secobatzellin Aand B, two new enzyme inhibitors from a deep-water Caribbean sponge of the genus Batzella. J. Nat. Prod., 62, 1208-11. 

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]. 

Discorhabdin alkaloids, Fig. (31), in contrast, are of high cytotoxicity, but they exhibit no inhibition of topoisomerase II. They were isolated from the Anthartic sponge Latrunculia apicalis [238], and more recently from a deep-water marine sponge of the genus Batzella sp. [239], The new discorhabdin derivative isolated from this sponge showed in vitro cytotoxicity against tumor cell lines. 

Marine sponges of these genus Batzella sp. also yielded novel... 

Secobatzelline A (83) from a sponge of the genus Batzella is active against P-388 (IC50 0.06 pg/ml) and human lung carcinoma A-549 cells (IC50 0.04 pg/ml) [73]. 

Cytotoxic and antifungal pyrroloquinoline alkaloids have been isolated from the Caribbean deep water sponge Batzella sp. Isobatzelline A (166) is considerably more active than the halogen-free isobatzelline B (P-388 leukemia IC50 0.42 and 2.6 pg/ml, Candida albicans IC50 3.1 and 25 pg/ml, respectively) [127]. 

Very simple sulfones have also been isolated from marine organisms. The isolation of sulfolane (290) from the sponge/tunicate composite Batzella spJLissoclinum sp. was the first report, either terrestrial or marine, of this compound as a natural product [213]. The pyrogallol Phenol B (291), obtained from the red alga Grateloupia filicina, was... 

Gunasekera SP, McCarthy PJ, Longley RE, Pomponi SA, Wright AE, Lobkovsky E, Clardy J (1999) Discorhabdin P, a New Enzyme Inhibitor from a Deep-Water Caribbean Sponge of the Genus Batzella. J Nat Prod 62 173... 

Discorhabdin and related pigments have been isolated from temperate and tropical sponges of the genera Latrunculia, Prianos, Zyzzya, and Batzella 94 discorhabdin C (Structure 7.11)95 and G (Structure 7.12)38 were recently found in Latrunculia apicalis collected from McMurdo Sound.96 Discorhabdins often bear significant cytotoxicity. Discorhabdin C is perhaps the strongest sea star deterrent studied to date and displays broad spectrum antibiotic activity toward sympatric bacteria.38 96... 

Discorhabdin P (Structure 16.8) Sponge, Batzella sp. Heart disease19... 

On scanning numerous natural sources only the extracts from the Caribbean sponge Batzella sp. proved to be active [9], This led to the isolation of the batzelladines A (12) and B as the first low-molecular-weight compounds able to inhibit this interaction. Subsequently, batzelladines F (13) and G (14) were shown to induce dissociation of thyrosin kinase p56 and CD4 cells highly specific in an immunosuppressivity-based assay [lOJ. 

Patil AD, Kumar NV, Kokke WC et al (1995) Novel alkaloids from the sponge Batzella sp. inhibitors of HIV gpl20-human CD4 binding. J Org Chem 60 1182-1188... 

Alkaloids related to pyridoacridines are known also from sponges and tunicates. Discorhabdin C (79), which is the first marine pyrroloquinoline alkaloid, was isolated from the sponge Latmnculia cf. bocagei. More than 20 alkaloids of this class are known at moment (30). Additional examples of this family are batzelline A (80) from a deep-sea sponge of the genus Batzella and wakayin (81) from an ascidian Clavelina sp. 

Secobatzelline A and secobatzelline B were isolated from a deepwater marine sponge of the genus Batzella. Secobatzellines A and B inhibited the phosphatase activity of calcineurin, and secobatzelline A inhibited the peptidase activity of CPP32. Both compounds showed in vitro cytotoxicity against P388 and A549 cell lines [42]. 

Patil, A.D., Freyer, A.J., Taylor, P.B. et al. (1997) Batzelladines F-I, novel alkaloids from the sponge Batzella sp. Inducers of p561ck-CD4 dissociation. The Journal of Organic Chemistry, 62, 1814-1819. 

Figure 2 shows the isobatzelUne alkaloids. They were isolated from the sponge Batzella sp. and an Indopacific collection of Zyzzya fuliginosa. Their structures are very close to makaluvamines and they have the T-aminopyrroloimmoquinone skeleton [17, 18]. 

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