Batzellines

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... 

A family of alkaloids characterized by a pyrroloquinone skeleton has been isolated in recent years from several sponges. Included in this family are the batzellines, isobatzellines, damirones, makaluvamines, discorhabdins, prianosins and wayakin. These alkaloids have shown a... 

The sulfide marine metabolites having a pyrroloquinoline skeleton can be divided into three groups the batzellines-isobatzellines, the prianosins-discorhabdins, and the makaluvamines. All of these types of compounds have been isolated from sponges. 

Chang LC, Otero-Quintero S, Hooper JNA, Bewley CA (2002) Batzelline D and Isobatzel-line E from the Indopacific Sponge Zyzzyafuliginosa. J Nat Prod 65 776... 

The pyrroloquinone imine 122 is considered to be a key branching point for the biogenesis of damirones, batzellines, isobatzellines, makaluvamines [110], and... 

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. 

Oxidation of l-amino-4-methoxybenzenes with CAN is expected to afford p-iminoqninones. Thns, batzellines, makalnvamines and discorhabdins, isolated from marine organisms, possess a pyrroloiminoqninone moiety and can be synthesized by CAN-mediated oxidation of the corresponding 4-amino-7-methoxyindole derivative. 

Yamamura et al. developed an efficient route to the synthesis of the A, B, C, D, and E rings of the prianosins and discorhabdins, which led them successfully to synthesize discorhabdin C (Scheme 59) (210-212). Because their route involves the synthesis of the pyrroloquinoline skeleton of the pyrroloquinoline type alkaloids (213-217), they have also achieved the synthesis of batzelline C and isobatzelline C (213,214). Their synthesis involved first the construction of the C, D, and E rings as in 505, starting from 502, which was synthesized in three steps (212). Reaction of 502 with... 

Roberts D, Joule JA, Bros MA, Alvarez M (1997) Synthesis of pyrrolo[4,3,2-iie]quinolmes from 6,7-dimethoxy-4-methylquinoline. Formal total syntheses of damirones A and B, batzelline C, isobatzelline C, discorhabdin C, and makaluvamines A-D. J Org (Them 62 ... 

Alvarez M, Bros MA, Gras G, Ajana W, Joule JA (1999) Syntheses of batzelline A, batzeline... 

Tao XL, Nishiyama S, Yamamura S (1991) Total syntheses of batzelline C and isobatzelline... 

Tao XL, Cheng JF, Nishiyama S, Yamamura S (1994) Synthetic studies on tetrahydropyr-roloquinoline-containing natural products syntheses of discorhabdin C, batzelline C and isobatzelline C. Tetrahedron 50 2017-2028... 

Batzelline D Cycasin Zyzzya fuliginosa (sponge) Cycas cind related Cycadaceae... 

Prianosins belong to the group of pyrroloquinones, of which there are a few examples among Haplosderida (prianosins) and Poecilosclerida (batzellines and isobatzel-lines), but also in some ascidians (Clavelina sp.). Most of these compounds are cytotoxic. For more details Molinski (1993). 

The makaluvamines are a series of about 20 closely related derivatives that are similar to batzelline D and isobatzelline E. The generic term makaluvamine derives from Maka-luva Island in the Fiji Archipelago, where these sponges of the genus Zyzzya were collected (Radisky et al, 1993)... 

Chang, L.C., Otero-Quintero, S Hooper, J.N.A., and Bewley, C.A. (2002) Batzelline D and isobatzelline E from the Indopacific sponge Zyzzo/afidigmosa.J. Nat. Prod.. 65, 776-778. 

Yamada, F., Hamabuchi, S., Shimizu, A., and Somei, M. (1995) Simple total synthesis of marine alkaloids batzelline C, isobatzelline C, damirone A, and makahivamine A. Heterocycles, 41,1905—1908. 

Roberts, D., Alvarez, M., and Joule, J.A. (1996) Synthesis of 6-chloro-l,3,4,5-tetrahydro-7,8-dimelhoxy-l-melhylpyrrolo[4,3,2-(fe]quinoline from a quinoline formal total synthesis of batzelline C, isobatzelline C, discorhabdin C and makahivamine D. Tetrahedron Lett., 37,1509-1512. 

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