Batzelline D and isobatzelline E from the indopacific sponge Zyzzya fuliginosa.
Two new pyrroloquinoline alkaloids, isobatzelline E (1) and batzelline D (2), together with the known compounds batzelline C (3), isobatzelline C (4), and makaluvamine D (5), were isolated from an Indopacific collection of the marine sponge Zyzzya fuliginosa; the known compounds makaluvamines A (9), H (10), J (7), K (8), and P (6) were obtained from Z. fuliginosa collected in Papua New Guinea. The structures were elucidated by interpretation of 1D (1)H and (13)C NMR spectra and 2D HSQC and HSQC-LR spectra. Compounds 1-10 were isolated because the crude extracts of both Zyzzya species inhibited HIV-1 envelope-mediated cell fusion. However, the inhibition profile observed for the pure compounds 1-10 mirrors that reported for the inhibition of topoisomerase II by other pyrroloquinolines, leaving open the possibility that the activity results from interactions with DNA-modifying enzymes.
Chang
Leng Chee
LC
Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, Maryland 20892-0820, USA.
Otero-Quintero
Sarah
S
Hooper
John N A
JN
Bewley
Carole A
CA
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D019380:Anti-HIV Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002478:Cells, Cultured; D002851:Chromatography, High Pressure Liquid; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015497:HIV-1 / Q000187:drug effects; D051379:Mice; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010219:Papua New Guinea; D011161:Porifera / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D011804:Quinolines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D059005:Topoisomerase II Inhibitors
D000470:Alkaloids; D019380:Anti-HIV Agents; D004791:Enzyme Inhibitors; D011758:Pyrroles; D011804:Quinolines; D059005:Topoisomerase II Inhibitors; C461759:batzelline D; C461760:isobatzelline E