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Discovery and heterologous production of sarubicins and quinazolinone C-glycosides with protecting activity for cardiomyocytes
- Source :
- Organic Chemistry Frontiers. 8:3829-3837
- Publication Year :
- 2021
- Publisher :
- Royal Society of Chemistry (RSC), 2021.
-
Abstract
- Glycosylated natural products and their derivatives are important pharmaceutical agents. Genome mining of a C-glycosylated metabolite biosynthetic gene cluster (BGC) from a soil-derived Streptomyces strain led to the isolation of sarubicins A (1) and B (2), of which 1 has a rare 2-oxabicyclo[2.2.2] substructure arising from C-glycosylation and C–C bond formation between the aglycone and the C-4 position of deoxysugar. Heterologous expression of the sar BGC led to the production of sarubicins and three new C-glycosylated quinazolinones 3–5 with a single C–C bond between the aglycone and deoxysugar, indicating the stepwise formation mechanism of the two unusual C–C bonds. A convenient chemical transformation from 1 to 2 and a proposed biosynthetic pathway for sarubicins are presented. Significantly, compounds 1 and 2 showed potent protective effects on neonatal rat cardiomyocytes.
Details
- ISSN :
- 20524129
- Volume :
- 8
- Database :
- OpenAIRE
- Journal :
- Organic Chemistry Frontiers
- Accession number :
- edsair.doi...........af605dc993048d5d136baef45dd5eaec