Iminosugar idoBR1 isolated from Cucumber Cucumis sativus reduces inflammatory activity

Cucumbers have been anecdotally claimed to have anti-inflammatory activity for a long time, but the active principle was not identified. idoBR1, (2R,3R,4R,5S)-3,4,5-trihydroxypiperidine-2-carboxylic acid, is an iminosugar amino acid isolated from fruits of certain cucumbers, Cucumis sativus (Cucurbitaceae). It has no chromophore and analytically behaves like an amino acid making detection and identification difficult. It has anti-inflammatory activity reducing lipopolysaccharide (LPS)-induced tumor necrosis factor alpha (TNF-α) in THP-1 cells and ex vivo human blood. It showed selective inhibition of human α-l-iduronidase and sialidases from both bacteria (Tannerella forsythia) and human THP-1 cells. idoBR1 and cucumber extract reduced the binding of hyaluronic acid (HA) to CD44 in LPS-stimulated THP-1 cells and may function as an anti-inflammatory agent by inhibiting induced sialidase involved in the production of functionally active HA adhesive CD44. Similar to the related iminosugars, idoBR1 is excreted unchanged in urine following consumption. Its importance in the diet should be further evaluated

Synthesis of (+)-(R)-Tiruchanduramine

The absolute stereochemistry of the marine alkaloid (+)-(R)-tiruchanduramine was established via a convergent total synthesis in six steps and 15.5% overall yield from Fmoc-D-Dab(Boc)-OH

Cyclic guanidine containing amino acids that promote glucocerebrosidase

This is an accepted manuscript of an article published by Elsevier in Tetrahedron on 24/08/2022, available online: https://doi.org/10.1016/j.tet.2022.132959 The accepted version of the publication may differ from the final published version.Novel cyclic guanidine containing amino acids (S)-1, 2 and 3 were prepared from l-serine 5. (S)-2-Imino-3-methylimidazolidine-4-carboxylic acid hydrochloride salt 2. HCl and (3S, 6S)-3,6-bis(hydroxymethyl)-1,4-dimethylpiperazine-2,5-dione 15 showed in vitro promotion of the enzyme glucocerebrosidase.The authors would like to thank the Iraqi government (ZSA-T) and acknowledge the support of the Centre for Environmental Biotechnology Project part-funded by the European Regional Development Fund (ERDF) through the Welsh Government. We would like to thank the BEACON II scheme (ERDF; PJM) and the EPSRC National Mass Spectrometry Facility at Swansea.Published versio