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Discovery and heterologous production of sarubicins and quinazolinone C-glycosides with protecting activity for cardiomyocytes
Yu,Mingming; Luo,Jianying; Luo,Dan; He,Qiang; Yan,Yijun; Ji,Xu; Huang,Sheng-Xiong
2021
Source PublicationORGANIC CHEMISTRY FRONTIERS
ISSN2052-4129
Volume8Issue:14Pages:3829-3837
AbstractGlycosylated 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.
KeywordSTREPTOMYCES-VIOLACEORUBER TU22 BIOSYNTHESIS GRANATICIN ANTIBIOTICS METABOLISM MECHANISM PATHWAY ACID
DOI10.1039/d1qo00470k
WOS IDWOS:000653846900001
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Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/73627
Collection中国科学院昆明植物研究所
Affiliation1.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650204, Yunnan, Peoples R China
2.Chinese Acad Sci, Kunming Inst Bot, Yunnan key Lab Nat Med Chem, Kunming 650204, Yunnan, Peoples R China
3.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
4.Yunnan Univ Tradit Chinese Med, Coll Tradit Chinese Med, Kunming 650500, Yunnan, Peoples R China
5.Yunnan Univ, Minist Educ, Key Lab Med Chem Nat Resource, Kunming 650091, Yunnan, Peoples R China
Recommended Citation
GB/T 7714
Yu,Mingming,Luo,Jianying,Luo,Dan,et al. Discovery and heterologous production of sarubicins and quinazolinone C-glycosides with protecting activity for cardiomyocytes[J]. ORGANIC CHEMISTRY FRONTIERS,2021,8(14):3829-3837.
APA Yu,Mingming.,Luo,Jianying.,Luo,Dan.,He,Qiang.,Yan,Yijun.,...&Huang,Sheng-Xiong.(2021).Discovery and heterologous production of sarubicins and quinazolinone C-glycosides with protecting activity for cardiomyocytes.ORGANIC CHEMISTRY FRONTIERS,8(14),3829-3837.
MLA Yu,Mingming,et al."Discovery and heterologous production of sarubicins and quinazolinone C-glycosides with protecting activity for cardiomyocytes".ORGANIC CHEMISTRY FRONTIERS 8.14(2021):3829-3837.
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