Discorhabdins

Latnmcidia brevis RidlQ and Daidy, Hadromaida, Porif. discorhabdins fDvrroloiminoauinaiesL C8.3.A/antimiaobial and cytaoxic ai human tumor cells Perry 1988... 

Undeterm. Demosp. (likely in the genus Latrunculia) q>inardins A-C (discorhabdin-like pyrroloiminoquinaie alkal.) D Amix osio 1996A... 

Kita, Y. Tohma, H. Inagaki, M. Hatanaka, K. Yakura, T. (1992) Total synthesis of discorhabdin C a general aza spiro dienone formation from O-silylated phenol derivatives using a hypervalent iodine reagent. J. Am. Chem. Soc., 114,2175-80. 

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... 

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. 

Discorhabdins A (8), B (9) and C (10) have been isolated from several sponge species of the genus Latrunculia from New Zealand. They are powerful cytotoxins with IC50 values against the murine leukemia P-388 cell line in the range 0.03 - 0.01 pg/ml. Discorhabdin A has also been isolated from a Japanese sponge of the genus Prianos [29]. 

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. 

These complex sulfide-containing pyrroloiminoquinone alkaloids consist of the prianosins A-D (52, 53, 56, 57), isolated from the Okinawan Prianos melanos [54, 55], the discorhabdins A and B (52, 54), obtained from three different species of the New Zealand Latrunculia [56], discorhabdin D (57) from Latrunculia brevis and Prianos sp. [57], and discorhabdin Q (55), from Latrunculia purpurea, and several species of... 

Zyzzya genus [58]. The structure of prianosin A (= discorhabdin A) (52), including its absolute configuration, was unequivocally defined by X-ray analysis [54], while those of discorhabdins B (54) and D (57) were based on spectral data. The previous structures proposed for prianosins C and D [55] were revised to 2-hydroxydiscorhabdin D (56) and discorhabdin D (57), respectively [59]. A plausible biosynthetic pathway for these compounds suggests the involvement of a-amino acids tyrosine (C-l-N-9) and tryptophan (C-10-C-21) [55]. 

Harayama Y, Kita Y (2005) Pyrroloiminoquinone Alkaloids Discorhabdins and Makaluvamines. Curr Org Chem 9 1567... 

Yang A, Baker BJ, Grimwade J, Leonard A, McClintock JB (1995) Discorhabdin Alkaloids from the Antarctic Sponge Latrunculia apicalis. J Nat Prod 58 1596... 

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... 

Dijoux M-G, Gamble WR, Hallock YF, Cardellina II JH, van Soest R, Boyd MR (1999) A New Discorhabdin from Two Sponge Genera. J Nat Prod 62 636... 

Lang G, Pinkert A, Blunt JW, Munro MHG (2005) Discorhabdin W, the First Dimeric Discorhabdin. J Nat Prod 68 1796... 

Tohma H, Harayama Y, Hashizume M, Iwata M, Egi M, Kita Y (2002) Synthetic Studies on the Sulfur-Cross-Linked Core of Antitumor Marine Alkaloid, Discorhabdins Total Synthesis of Discorhabdin A. Angew Chem hit Ed 41 348... 

Harayama Y, Yoshida M, Kamimura D, Wada Y, Kita Y (2006) The Efficient Direct Synthesis of N.O-Acetal Compounds as Key Intermediates of Discorhabdin A Oxidative Fragmentation Reaction of a-Amino Acids or P-Amino Alcohols by Using Hypervalent Iodine(III) Reagents. Chem Eur J 12 4893... 

Grkovic T, Kaur B, Webb VL, Copp BR (2006) Semi-Synthetic Preparation of the Rare, Cytotoxic, Deep-Sea Sourced Sponge Metabolites Discorhabdins P and U. Bioorg Med Chem Lett 16 1944... 

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