Sebastianines A and B, novel biologically active pyridoacridine alkaloids from the Brazilian ascidian Cystodytes dellechiajei.
Fractionation of the crude methanol extract of the ascidian Cystodytes dellechiajei collected in Brazil yielded two novel alkaloids, sebastianine A (1) and sebastianine B (2). The structures of both 1 and 2 were established by analysis of spectroscopic data, indicating an unprecedented ring system for both compounds, comprising a pyridoacridine system fused with a pyrrole unit in sebastianine A (1) and a pyridoacridine system fused with a pyrrolidine system condensed with alpha-hydroxyisovaleric acid in sebastianine B (2). Both alkaloids displayed a cytotoxic profile against a panel of HCT-116 colon carcinoma cells indicative of a p53 dependent mechanism.
Torres
Yohandra R
YR
Instituto de Química de São Carlos, Universidade de São Paulo, CP 780, CEP 13560-970, São Carlos, SP, Brazil.
Bugni
Tim S
TS
Berlinck
Roberto G S
RG
Ireland
Chris M
CM
Magalhães
Alviclér
A
Ferreira
Antonio G
AG
Moreira Da Rocha
Rosana
R
D000166:Acridines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001938:Brazil; D002384:Catalysis; D002470:Cell Survival / Q000187:drug effects; D003110:Colonic Neoplasms; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011725:Pyridines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014407:Tumor Cells, Cultured / Q000187:drug effects; D016159:Tumor Suppressor Protein p53 / Q000378:metabolism; D014561:Urochordata / Q000737:chemistry*
D000166:Acridines; D000470:Alkaloids; D000970:Antineoplastic Agents; D006576:Heterocyclic Compounds, 4 or More Rings; D011725:Pyridines; D016159:Tumor Suppressor Protein p53; C470701:sebastianine A; C470702:sebastianine B