Plakohypaphorines are

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

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 ...

s named for their similarity to hypaphorine (''N,N,N''-trimethyl

tryptophan Tryptophan (symbol Trp or W) is an α-amino acid that is used in the biosynthesis of proteins. Tryptophan contains an α-amino group, an α-carboxylic acid group, and a side chain indole, making it a polar molecule with a non-polar aromat ...

betaine A betaine () in chemistry is any neutral chemical compound with a positively charged cationic functional group that bears no hydrogen atom, such as a Quaternary ammonium cation, quaternary ammonium or phosphonium cation (generally: Onium compou ...

). First reported in the

Caribbean The Caribbean ( , ; ; ; ) is a region in the middle of the Americas centered around the Caribbean Sea in the Atlantic Ocean, North Atlantic Ocean, mostly overlapping with the West Indies. Bordered by North America to the north, Central America ...

sponge Sponges or sea sponges are primarily marine invertebrates of the animal phylum Porifera (; meaning 'pore bearer'), a basal clade and a sister taxon of the diploblasts. They are sessile filter feeders that are bound to the seabed, and a ...

Plakortis ''Plakortis'' is a genus of marine sponges in the order Homosclerophorida, first described by Franz Eilhard Schulze in 1880. Description ''Plakortis'' sponges are characterised by having: #inorganic (spicular) skeletal complement #Skeleton com ...

simplex'' in 2003, plakohypaphorines A-C were the first iodine-containing

indole alkaloids Indole alkaloids are a class of alkaloids containing a Moiety (chemistry), structural moiety of indole; many indole alkaloids also include isoprene groups and are thus called terpene indole or secologanin tryptamine alkaloids. Containing more than ...

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 Alpha-Amino acids Halogen-containing alkaloids 5-Halotryptamines Non-proteinogenic amino acids Organoiodides N,N,N-Trialkyltryptamines Tryptamine alkaloids Zwitterions