(+)- and (−)-Spiroreticulatine, A Pair of Unusual
Spiro Bisheterocyclic Quinoline-imidazole Alkaloids from the South
China Sea Sponge <i>Fascaplysinopsis reticulata</i>
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Abstract
A pair of novel bisheterocyclic quinoline-imidazole
alkaloids,
(+)- and (−)-spiroreticulatine (<b>1</b>), were isolated
from the South China Sea sponge <i>Fascaplysinopsis reticulata</i>. The structures and absolute configurations were elucidated by comprehensive
spectroscopic analysis, single-crystal X-ray diffraction, and quantum
chemical calculation methods. Spiroreticulatine is the first example
of a sponge-derived natural spiro quinoline-imidazole alkaloid that
may derive from tryptophan and 1,3-dimethylurea. Compound <b>1</b> showed inhibitory activity on IL-2 production but inactive against
normal tumor cell lines
