Bioassay guided investigation of an undescribed thorectid sponge from Saipan in the Commonwealth of the Northern Marianas Islands resulted in the isolation of two new fascaplysin related alkaloids (2 and 3), along with the known 10-bromofascaplysin (1). The structures of the isolated metabolites were unambiguously established based on extensive NMR spectroscopic (1H, 13C, COSY, HMQC and HMBC) and MS analyses.
A marine literature database produced and maintained by the Department of Chemistry, University of Canterbury (2003) Marine literature.
2.
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4.
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5.
(b) SegravesNL, LopezS, JohnsonTA, SaidSA, FuX, SchmitzFJ, PietraszkiewiczH, ValerioteFA, CrewsP. (2003) Structures and cytotoxicities of fascaplysin and related alkaloids from two marine phyla – Fascaplysinopsis sponges and Didemnum tunicates. Tetrahedron Letters, 44, 3471–3475 and references therein
6.
(c) SegravesNL, RobinsonSJ, GarciaD, SaidSA, FuX, SchmitzFJ, PietraszkiewiczH, ValerioteFA, CrewsP. (2004) Comparison of fascaplysin and related alkaloids: A study of structures, cytotoxicities, and sources. Journal of Natural Products, 67, 783–792 and references therein.
7.
(a) JimenezC, QuinoaE, AdamczeskiM, HunterLM, CrewsP. (1991) Novel sponge-derived amino acids. 12. Tryptophan- derived pigments and accompanying sesterterpenes from Fascaplysinopsis reticulata.Journal of Organic Chemistry, 56, 3403–3410
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10.
KirschG, KonigGM, WrightAD, KaminskyR. (2000) A new bioactive sesterterpene and antiplasmodial alkaloids from the marine sponge Hyrtios cf. erecta. Journal of Natural Products, 63, 825–829.
11.
FoderaroTA, BarrowsLR, LassotaP, IrelandCM. (1997) Bengacarboline, a new β-carboline from a marine ascidian Didemnum sp.Journal of Organic Chemistry, 62, 6064–6065.
12.
RollDM, IrelandCM, LuHS, ClardyJ. (1988) Fascaplysin, an unusual antimicrobial pigment from the marine sponge Fascaplysinopsis sp. Journal of Organic Chemistry, 53, 3276–3278.
13.
PopovAM, StonikVA (1991) Physiological activity of fascaplysin, an unusual pigment from tropic sea spongesAntibioiki Khimioterapiya, 36, 12–14.
14.
MaklerMT, RiesJM, WilliamsJA, BancroftJE, PiperRC, GivvinsBL, HinrichsDJ (1993) Parasite lactate dehydrogenase as an assay for Plasmodium falciparum sensitivity. American Journal of Tropical Medicine and Hygiene, 48, 739–741.
