3 years ago

Serinolamides and Lyngbyabellins from an Okeania sp. Cyanobacterium Collected from the Red Sea

Serinolamides and Lyngbyabellins from an Okeania sp. Cyanobacterium Collected from the Red Sea
Yasuyuki Nogata, Fuyuhiko Matsuda, Taiki Umezawa, Sultan S. Al-Lihaibi, Ahmed Abdel-Lateff, Loida O. Casalme, Julie G. Petitbois, Tatsufumi Okino, Erina Yoshimura, Walied M. Alarif, Julius Adam V. Lopez
NMR- and MS-guided fractionation of an extract of an Okeania sp. marine cyanobacterium, collected from the Red Sea, led to the isolation of four new metabolites, including serinolamides C (1) and D (2) and lyngbyabellins O (3) and P (4), together with the three known substances lyngbyabellins F (5) and G (6) and dolastatin 16 (7). The planar structures of the new compounds were determined using NMR and MS analyses. The absolute configurations of 1 and 2 were determined by Marfey’s analysis of their hydrolysates. The absolute configuration of 3 was ascertained by chiral-phase chromatography of degradation products, while that of 4 was determined by comparison to 3 and 5. The cytotoxic and antifouling activities of these compounds were evaluated using MCF7 breast cancer cells and Amphibalanus amphitrite larvae, respectively. Compounds 3, 4, and 7 exhibited strong antifouling activity, and 3 and 7 were not cytotoxic. A structure–activity relationship was observed for the cytotoxicity of the lyngbyabellins with the presence of a side chain (4 is more active than 3) leading to greater activity. For the antifouling activity, the acyclic form without a side chain (3) was the most active.

Publisher URL: http://dx.doi.org/10.1021/acs.jnatprod.7b00449

DOI: 10.1021/acs.jnatprod.7b00449

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