Combining JBCA and Marfey's methodology to determine the absolute configuration of threonines: the case of gunungamide A, a new cyclic depsipeptide containing chloropyrrole from the sponge Discodermia sp.

Abstract

JBCA and Marfey's allowed us to distinguish threonines diasteroisomers.

Absolute Stereochemistry Determination of Bioactive Marine-Derived Cyclopeptides by Liquid Chromatography Methods: An Update Review (2018–2022)

“…It is important to highlight that from January 2018 to November 2022, there were several studies on the structural revision of marine-derived cyclopeptides discovered before 2018, reporting the reinvestigation of the stereochemistry by LC and other methods, for the establishment of complete absolute configurations [ 138 , 207 , 208 ]. The focus of this review is on marine cyclopeptides, even though LC methods were chosen for the determination of the absolute configurations of the amino acid residues of the recently isolated linear peptides [ 209 , 210 , 211 ].…”

Marine Organisms as a Prolific Source of Bioactive Depsipeptides

“…Marine sponges are well known as prolific sources of biologically natural products and are the second largest group of producers of marine-derived depsipeptides ( 162 – 212 , Figure 8 ) [ 71 , 72 , 73 , 74 , 75 , 76 , 77 , 78 , 79 , 80 , 81 , 82 , 83 , 84 ]. With respect to the genus and species, however, there are no striking features about these sponges.…”

“…Daedophamide ( 167 ) displayed strong cytotoxic activity against a panel of four human tumor cell lines with GI 50 values in the submicromolar range [ 77 ]. Gunungamide A ( 168 ), produced by an Indonesian sponge Discodermia sp., possesses an unusual chloropyrrol ring [ 78 ]. Homophymine analogs ( 169 – 178 ) featuring new polyketide-derived end groups displayed potent antiproliferative activity (IC 50 in the nM range) against a panel of human cancer cell lines [ 79 , 80 ].…”

Unique Polyhalogenated Peptides from the Marine Sponge Ircinia sp.

“…In the course of our screening program to isolate novel compounds with antitumor properties from marine sources, we have isolated two unique peptides haloirciniamide A (1) and seribunamide A (2) from an Ircinia specimen, which was collected off the coast of Thousand Islands. It is worth mentioning that the number of known peptides with a halogenated pyrrole ring is limited, with only cyclocinamides and corticiamide A [16] as well as gunungamide A [17] having been described as possessing chlorinated pyrrole rings. Although there are dozens of dibromopyrrolecarboxamide derivatives from porifera like nagelamide [18] and carteramine [19], mainly from Agela and Stylissa species, compound 1 is the first example of a cyclopeptide containing a halogenated pyrrole ring in its structure.…”