Plakohypaphorines are

halogenated In chemistry, halogenation is a chemical reaction that entails the introduction of one or more halogens into a compound. Halide-containing compounds are pervasive, making this type of transformation important, e.g. in the production of polymers, ...

indolic

non-proteinogenic amino acid In biochemistry, non-coded or non-proteinogenic amino acids are distinct from the 22 proteinogenic amino acids (21 in eukaryotesplus formylmethionine in eukaryotes with prokaryote organelles like mitochondria) which are naturally encoded in the ge ...

s named for their similarity to hypaphorine (''N,N,N''-trimethyltryptophan). First reported in the Caribbean

sponge Sponges, the members of the phylum Porifera (; meaning 'pore bearer'), are a basal animal clade as a sister of the diploblasts. They are multicellular organisms that have bodies full of pores and channels allowing water to circulate throug ...

''Plakortis simplex'' in 2003, plakohypaphorines A-C were the first iodine-containing indoles to be discovered in nature. Plakohypaphorines D-F, also found in ''P. simplex'', were reported in 2004 by a group including the researchers who discovered the original plakohypaphorines.

References

*Taglialatela-Scafati Orazio et al., 2003. ''Plakohypaphorines A-C, Iodine-Containing Alkaloids from the Caribbean Sponge'' Plakortis simplex. European Journal of Organic Chemistry. 2003(2), pp. 284–287. *Borrelli, Francesca, et al., 2004. ''Iodinated Indole Alkaloids From Plakortis simplex, New Plakohypaphorines and an Evaluation of Their Antihistamine Activity''. European Journal of Organic Chemistry. 2004(15), pp. 3227–3232. {{Tryptamines Non-proteinogenic amino acids Halogen-containing alkaloids Organoiodides Zwitterions