de Muizon C. J., Moriou C., Petek Sylvain, Ekins M., Rousseau M., Al Mourabit A. (2022). Isolation, synthesis and absolute configuration of the pericharaxins A and B, epimeric hydroxy-polyene glycerol ethers from the calcarean sponge Pericharax heteroraphis. Marine Drugs, 20 (10), 635 [14 p.].
Titre du document
Isolation, synthesis and absolute configuration of the pericharaxins A and B, epimeric hydroxy-polyene glycerol ethers from the calcarean sponge Pericharax heteroraphis
de Muizon C. J., Moriou C., Petek Sylvain, Ekins M., Rousseau M., Al Mourabit A.
Source
Marine Drugs, 2022,
20 (10), 635 [14 p.]
Naturally occurring epimeric hydroxy-polyene glycerol ether pericharaxins A (1a) and B (1b) were isolated from the calcarean sponge Pericharax heteroraphis. The structural and stereochemical characterization of both diastereoisomers were established on the basis of spectroscopic data analysis and total synthesis in seven steps. The mixture of pericharaxins A (1a) and B (1b) was proven to be epimeric by chiral-phase HPLC analysis of both synthetic and natural samples. Further separation of the epimers and application of Mosher's method to the synthetic compounds allowed unequivocal absolute configuration assignment. While natural products and the synthetic intermediates were shown to be non-cytotoxic on the HCT116 cell line, the endochondral differentiation activity using human type X collagen transcription activity in ATDC5 cells is interesting.
Plan de classement
Sciences fondamentales / Techniques d'analyse et de recherche [020]
;
Substances naturelles [035]
