Novel sponge-derived amino acids. 12. Tryptophan-derived pigments and accompanying sesterterpenes from Fascaplysinopsis reticulata

The Journal of Organic Chemistry
1991.0

Abstract

This paper reports the bioactive constituents of Fascaplysinopsis reticulata collected from the Benga Lagoon of the Fiji islands. The previous literature of this genus includes two aplysinopsins (monomeric tryptophans) from F. reticulata, as well as fascaplysin (5a) (an apparent tryptophan dimer) and luffariellolide (3) (a sesterterpene) from Fascaplysinopsis sp. Our investigation of F. reticulata has revealed new sesterterpenes isodehydroluffariellolide (1) and dehydroluffariellolide diacid (2); unique alkaloid-sesterterpene salts fascaplysin A (5b) [fascaplysin cation/dehydroluffariellolide diacid anion] and homofascaplysin A cation/dehydroluffariellolide diacid anion (6); and novel neutral alkaloids homofascaplysin C (7), homofascaplysin B (8), and secofascaplysin A (9). These substances were accompanied by fascaplysin (5a) and the known alkaloid (+)-octopamine (4). The most important findings in this study are (a) fascaplysin derivative 5b is the first known salt comprised of a complex alkaloid cation and a terpene carboxylate anion, and (b) secofascaplysin A (9) is the first naturally occurring β-carbolinone. An amino acid biogenesis pathway is outlined for each of the above alkaloids. The biological activity profile against the HIV reverse transcriptase is reported for selected metabolites.

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