847925-82-0Relevant academic research and scientific papers
Cyclic depsipeptides, grassypeptolides D and e and Ibu- epidemethoxylyngbyastatin 3, from a Red Sea Leptolyngbya cyanobacterium
Thornburg, Christopher C.,Thimmaiah, Muralidhara,Shaala, Lamiaa A.,Hau, Andrew M.,Malmo, Jay M.,Ishmael, Jane E.,Youssef, Diaa T. A.,McPhail, Kerry L.
, p. 1677 - 1685 (2011)
Two new grassypeptolides and a lyngbyastatin analogue, together with the known dolastatin 12, have been isolated from field collections and laboratory cultures of the marine cyanobacterium Leptolyngbya sp. collected from the SS Thistlegorm shipwreck in the Red Sea. The overall stereostructures of grassypeptolides D (1) and E (2) and Ibu-epidemethoxylyngbyastatin 3 (3) were determined by a combination of 1D and 2D NMR experiments, MS analysis, Marfey's methodology, and HPLC-MS. Compounds 1 and 2 contain 2-methyl-3-aminobutyric acid and 2-aminobutyric acid, while biosynthetically distinct 3 contains 3-amino-2-methylhexanoic acid and the β-keto amino acid 4-amino-2,2-dimethyl-3-oxopentanoic acid (Ibu). Grassypeptolides D (1) and E (2) showed significant cytotoxicity to HeLa (IC50 = 335 and 192 nM, respectively) and mouse neuro-2a blastoma cells (IC50 = 599 and 407 nM, respectively), in contrast to Ibu-epidemethoxylyngbyastatin 3 (neuro-2a cells, IC50 > 10 μM) and dolastatin 12 (neuro-2a cells, IC 50 > 1 μM).
Urumamide, a novel chymotrypsin inhibitor with a β-amino acid from a marine cyanobacterium Okeania sp.
Kanamori, Yuki,Iwasaki, Arihiro,Sumimoto, Shinpei,Suenaga, Kiyotake
supporting information, p. 4213 - 4216 (2016/08/25)
Urumamide, a novel cyclic depsipeptide that contains a β-amino acid, was isolated from a marine cyanobacterium Okeania sp. Its gross structure was determined by spectroscopic analyses, and the absolute configuration was established based on Marfey's analyses and chiral HPLC analyses of hydrolysis products. Biologically, urumamide inhibited the growth of human cancer cells. In addition, urumamide inhibited chymotrypsin.
