Fourteen dibromopyrrole alkaloids were isolated from the marine sponge Acanthostylotella sp. collected in Indonesia. In addition to the known compounds 4,5-dibromo-N-(methoxy-methyl)-1H-pyrrole-2-carboxamide (7), 4,5-dibromo-1H-pyrrole-2-carboxamide (8), mukanadin D (9), (±)-longamide B methyl ester (10), (±)-longamide B (11), (±)-longamide (12), 3,4-dibromo-1H-pyrrole-2-carboxamide (13), 2-cyano-4,5-dibromo-1H-pyrrole (14), six compounds were isolated that proved to be new natural products including acanthamides A – D (1 – 4), methyl 3,4-dibromo-1H-pyrrole-2-carboxylate (5) and 3,5-dibromo-1H-pyrrole-2-carboxylic acid (6). The structures of the new compounds were unequivocally identified based on one and two dimensional NMR and on HRFTMS as well as by comparison with the literature.
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7.
PatelJ, Pelloux-LéonN, MinassianF, ValléeY. (2005) Syntheses of S-enantiomers of hanishin, longamide B, and longamide B methyl ester from L-aspartic acid β-methyl ester: establishment of absolute stereochemistry. Journal of Organic Chemistry, 70, 9081–9084.
8.
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9.
UmeyamaA, ItoS, YuasaE, AriharaS, YamadaT. (1998) A new bromopyrrole alkaloid and the optical resolution of the racemate from the marine sponge Homaxinella sp. Journal of Natural Products, 61, 1433–1434.
10.
UemotoH, TsudaM, KobayashiJ. (1999) Mukanadins A–C. new bromopyrrole alkaloids from the marine sponge Agelas nakamurai.Journal of Natural Products, 62, 1581–1583.
11.
HuJ, PengJ, KaziA, KellyM, HamannM. (2005) Bromopyrrole alkaloids from the Jamaican sponge Didiscus oxeata.Journal of Chemistry Research, 7, 427–428.
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14.
MeijerL, ThunissenAMWH, WhiteAW, GarnierM, NikolicM, TsaiLH, WalterJ, CleverlyKE, SalinasPC, WuYZ, BiernatJ, MandelkowEM, KimSH, PettitGR. (2000) Inhibition of cyclin-dependent kinases, GSK-3β and CK1 by hymenialdisine, a marine sponge constituent. Chemistry and Biology, 7, 51–63.
15.
(a) HassanW, ElsayedZ, ProkschP. (2007) Bromopyrrole alkaloids from the marine sponge Agelas oroides.Mansoura Journal of Pharmaceutical Sciences, 23, 39–52.
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(b)EderC, ProkschP, WrayV, van SoestRWM, FerdinandusE, PattisinaLA Sudarono. (1999) New bromopyrrole alkaloids from the Indopacific sponge Agelas nakamurai.Journal of Natural Products, 62, 1295–1299.
17.
(a) HassanW, ElkhayatE, EdradaR, EbelR, ProkschP. (2007) New bromopyrrole alkaloids from the marine sponges Axinella damicornis and Stylissa flabelliformis.Natural Product Communications, 2, 1149–1154.
18.
(b) SupriyonoA, SchwarzB, WrayV, WitteL, MüllerWEG, van SoestRWM, SumaryonoW, ProkschP. (1995) Bioactive alkaloids from the tropical marine sponge Axinella carteri. Zeitschrift für Naturforschung C, Journal of Biosciences, 50c, 669–674.
19.
ForenzaS, MinaleL, RiccioR, FattorussoE. (1971) New bromopyrrole derivatives from the sponge Agelas oroides.Journal of Chemical Society, Chemical Communications, 1129–1130.
20.
GarciaEE, BenjaminLE, Ian FryerR. (1973) Reinvestigation into the structure of oroidin, a bromompyrrole derivatives from marine sponge. Journal of Chemical Society, Chemical Communications, 78–79.
