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- Title
Isolation, Synthesis and Absolute Configuration of the Pericharaxins A and B, Epimeric Hydroxy-Polyene Glycerol Ethers from the Calcarean Sponge Pericharax heteroraphis.
- Authors
Jourdain de Muizon, Capucine; Moriou, Céline; Petek, Sylvain; Ekins, Merrick; Rousseau, Marthe; Al Mourabit, Ali
- Abstract
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.
- Subjects
SYNTHETIC products; GLYCERYL ethers; NATURAL products; CELL lines; DIASTEREOISOMERS; DATA analysis
- Publication
Marine Drugs, 2022, Vol 20, Issue 10, p635
- ISSN
1660-3397
- Publication type
Article
- DOI
10.3390/md20100635