New Cyclic Cystine Bridged Peptides from the Sponge Suberites waedoensis

Abstract

Two new peptides, chujamides A (1) and B (2), were isolated from the marine sponge Suberites waedoensis, which was collected from Korean waters. Based upon the results of the combined spectroscopic analyses, the structures of these compounds were determined to be proline-riched and cyclic cystine bridged dodeca- and undecapeptides. The absolute configurations of all amino acid residues were determined to be l by advanced Marfey’s analysis. The new compounds exhibited weak cytotoxicities against A549 and K562 cell-lines, and compound 2 also demonstrated moderate inhibitory activity against Na+/K+-ATPase.

Marine natural products

“…525 The genera Asteropus, Discodermia, Pipestela, Reniochalina, Stylissa, Suberites and Theonella have also yielded a large number of peptides 787-806. [526][527][528][529][530][531][532] Callyspongiolide 807 is an unusual carbamate macrolide with an unprecedented conjugated dienyne side chain isolated from Callyspongia sp. (Ambon, Indonesia).…”

Marine Natural Peptides: Determination of Absolute Configuration Using Liquid Chromatography Methods and Evaluation of Bioactivities

“…The absolute configuration analysis of the amino acid residues of microsclerodermins J ( 133 ) and K ( 134 ), isolated from the sponge Microscleroderma herdmani , indicated, besides the amino acids common to both microsclerodermins, the presence of l -Phe, and l -Gly in 133 , and l -Val, and l -Ala in 134 [ 130 ]. Moreover, in the case of euryjanicins E–G ( 135 – 137 ), isolated from the Caribbean sponge Prosuberites laughlini [ 131 ], chujamide A ( 138 ), isolated from Suberites waedoensis [ 132 ], and kapakahines A–D ( 139 – 142 ), isolated from Cribrochalina olemda [ 133 ], all the amino acid residues were proved to have the L configuration. However, except for d -Phe, all the amino acid residues of koshikamide B ( 143 ), isolated from the marine sponge Theonella sp., were shown to possess L-configuration [ 134 ].…”

Potential Approaches Versus Approved or Developing Chronic Myeloid Leukemia Therapy

“…Aaptamine also induced the arrest of cell cycle at G2/M phase and a higher p21 levels, as demonstrated by protein analyses in K562 cells. Finally, the isolation from the sponge Suberites waedoensis of chujamides A and B was reported by Song and co-authors (142). Chujamides A and B are cyclic cysteine bridged peptides, with cytotoxicity toward K562 cells with LC50 values of 37 µM and 55.6 µM, respectively.…”

“…Among the screened organisms, Porifera showed selectivity against leukemia cell lines (134). Regarding the purified compounds from sponges with activity against CML, there are gombamide A, compound 1-8, Lembehyne B, Heteronemin, Smenospongine, Aaptamine, chujamides A and B (135)(136)(137)(138)(139)(140)(141)(142).…”