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Corrected Structure of Natural Hyacinthacine C1 via Total Synthesis
- Source :
- Journal of Natural Products. 82:358-367
- Publication Year :
- 2019
- Publisher :
- American Chemical Society (ACS), 2019.
-
Abstract
- Hyacinthacines C1 and C4 are natural products that were isolated from Hyacinthoides non-scripta and Scilla socialis in 1999 and 2007, respectively. Despite their different 1H NMR and 13C NMR spectroscopic data, these compounds have been assigned the same structures, including absolute configurations. This work details the total synthesis of natural (+)-hyacinthacine C1, whose structure is confirmed as being the C-6 epimer of that reported. The synthetic strategy focused on inverting the configuration at C-1 of the final hyacinthacines via operating the inversion at the corresponding carbon atom in three previously synthesized intermediates. To do this, the advanced intermediates were subjected to Swern oxidation, followed by a stereoselective reduction with L-Selectride. This approach led to the synthesis of (+)-5 -epi-hyacinthacine C1 (15), the corrected structure for (+)-hyacinthacine C1 (19), (+)-6,7-di- epi-hyacinthacine C1 (23), and (+)-7- epi-hyacinthacine C1 (29). Glycosidase inhibition assays revealed that (+)-hyacinthacine C1 (19) proved the most active, with IC50 values of 33.7, 55.5, and 78.2 μM, against the α-glucosidase of rice, human lysosome, and rat intestinal maltase, respectively.
- Subjects :
- Pharmacology
010405 organic chemistry
Chemistry
Stereochemistry
Organic Chemistry
Pharmaceutical Science
Total synthesis
Stereoisomerism
Carbon-13 NMR
01 natural sciences
0104 chemical sciences
Analytical Chemistry
010404 medicinal & biomolecular chemistry
Complementary and alternative medicine
Drug Discovery
Proton NMR
Swern oxidation
Molecular Medicine
Epimer
Stereoselectivity
Maltase
Subjects
Details
- ISSN :
- 15206025 and 01633864
- Volume :
- 82
- Database :
- OpenAIRE
- Journal :
- Journal of Natural Products
- Accession number :
- edsair.doi...........91639eb9c602d209425634e18899a22a