Plakohypaphorine

Plakohypaphorines are halogenated indolic non-proteinogenic amino acids named for their similarity to hypaphorine (N,N,N-trimethyltryptophan betaine). First reported in the Caribbean sponge Plakortis simplex in 2003, plakohypaphorines A-C were the first iodine-containing indole alkaloids 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.

Plakohypaphorine	Chemical name	Chemical formula	SMILES	Image
Plakohypaphorine	7-Iodo-N,N,N-trimethyltryptophan	C14H17IN2O2	OC(=O)C(N(C)(C)C)Cc2cnc1c2cccc1I
Plakohypaphorine B	6,7-Diiodo-N,N,N-trimethyltryptophan	C14H16I2N2O2	OC(=O)C(N(C)(C)C)Cc2cnc1c2ccc(I)c1I
Plakohypaphorine C	5,7-Diiodo-N,N,N-trimethyltryptophan	C14H16I2N2O2	CN(C)(C)C(C(=O)O)Cc2cnc1c2cc(I)cc1I
Plakohypaphorine D	5,6-Diiodo-N,N,N-trimethyltryptophan	C14H16I2N2O2	Ic2cc1c(cc2I)ncc1CC(C(O)=O)N(C)(C)C
Plakohypaphorine E	5,6,7-Triiodo-N,N,N-trimethyltryptophan	C14H15I3N2O2	CN(C)(C)C(C(=O)O)Cc1cnc(c(I)c2I)c1cc2I
Plakohypaphorine F	6-Chloro-5-iodo-N,N,N-trimethyltryptophan	C14H16ClIN2O2	Clc2c1ncc(CC(C(O)=O)N(C)(C)C)c1cc(I)c2

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.