Bengamides and Related New Amino Acid Derivatives from the New Caledonian Marine Sponge Jaspis carteri

Abstract

Five new amino acid derivatives were isolated from the New Caledonian sponge Jaspis carteri, together with known bengamides A and B. The structures of the new compounds were determined by interpretation of their spectral data and by comparison with spectral data of known bengamides. Compounds 4−7 are simply the tridecanoate and pentadecanoate analogues of the original bengamides A and B, whereas compound 8 is a caprolactam formamide derivative of bengamide B.

Marine natural products

“…196 Five additional bengamide derivatives, bengamides G-K 249-253, were obtained from a New Caledonian specimen of Jaspis carteri. 197 Dysiherbaine 254, which was isolated from Dysidea herbacea from Yap, Micronesia, is a neurotoxic amino acid with activity similar to that of domoic acid. 198 D. herbacea from the southern Great Barrier Reef has yielded the diketopiperazines 255 and 256 and thiazole 257 together with known metabolites.…”

Two New Jaspamide Derivatives from the Marine Sponge Jaspis splendens

“…A wide variety of constituents has been isolated from this genus including several jaspamide derivatives from Jaspis splendens [ 18 – 21 ], isomalabaricane triterpenes from Jaspis stellifera [ 22 – 24 ] and other species [ 25 – 29 ], cytotoxic macrolides from the Okinawan sponge Jaspis sp. [ 30 ], bengazoles [ 31 , 32 ] that stand out as unique bis-oxazoles containing a carbohydrate-like polyol side chain, antiparasitic, antimicrobial, and cytotoxic amino acid derivatives known as bengamides [ 33 – 35 ], cytotoxic bromotyrosine derivatives [ 36 , 37 ], and a series of dihydroxystyrene sulphate derivatives [ 38 – 42 ].…”

Octopus vulgaris ink extracts exhibit antioxidant, antimutagenic, cytoprotective, antiproliferative, and proapoptotic effects in selected human cancer cell lines

“…D'Auria et al. (1997) detected a caprolactam formamide in the n‐hexane fraction of New Caledonian sponge ( Jaspis carteri ) tissue using both 1 H‐ and 13 C‐NMR analyses. Likewise, the authors used a similar purification approach like the one used in this research, isolating the newly compound by open column chromatography using CHCl 3…”