Concise Synthesis of Licochalcone A through Water-Accelerated [3,3]-Sigmatropic Rearrangement of an Aryl Prenyl Ether

Jeon, Jae Heung; Kim, Mi Ran; Jun, Jong‐Gab

doi:10.1055/s-0030-1258381

Cited by 15 publications

(2 citation statements)

References 5 publications

(8 reference statements)

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“…However, it usually takes years before the roots can be harvested for LCA extraction with the yield too low to meet the market demand. The chemical synthesis protocols of LCA have been long reported and optimized, but due to the complexity and high cost of the process, no protocols have been used in industry so far [8]. The biosynthetic pathway of LCA as well as the underlying molecular regulation mechanisms have been rarely reported.…”

Section: Introductionmentioning

confidence: 99%

Histone Deacetylase GiSRT2 Negatively Regulates Flavonoid Biosynthesis in Glycyrrhiza inflata

Zeng,

Huang,

Zhou

et al. 2023

Cells

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Glycyrrhiza inflata Batalin is a medicinal licorice species that has been widely used by humans for centuries. Licochalcone A (LCA) is a characteristic flavonoid that accumulates in G. inflata roots with high economical value. However, the biosynthetic pathway and regulatory network of its accumulation remain largely unknown. Here we found that a histone deacetylase (HDAC) inhibitor nicotinamide (NIC) could enhance the accumulation of LCA and total flavonoids in G. inflata seedlings. GiSRT2, a NIC-targeted HDAC was functionally analyzed and its RNAi transgenic hairy roots accumulated much more LCA and total flavonoids than its OE lines and the controls, indicating a negative regulatory role of GiSRT2 in the accumulation of LCA and total flavonoids. Co-analysis of transcriptome and metabolome of RNAi-GiSRT2 lines revealed potential mechanisms in this process. An O-methyltransferase gene, GiLMT1 was up-regulated in RNAi-GiSRT2 lines and the encoded enzyme catalyzed an intermediate step in LCA biosynthesis pathway. Transgenic hairy roots of GiLMT1 proved that GiLMT1 is required for LCA accumulation. Together, this work highlights the critical role of GiSRT2 in the regulation of flavonoid biosynthesis and identifies GiLMT1 as a candidate gene for the biosynthesis of LCA with synthetic biology approaches.

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Section: Introductionmentioning

confidence: 99%

Histone Deacetylase GiSRT2 Negatively Regulates Flavonoid Biosynthesis in Glycyrrhiza inflata

Zeng,

Huang,

Zhou

et al. 2023

Cells

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“…Phenols (and, more generally, flavonoids) are widely recognized as important moieties in medicinally active natural products . Indeed, compounds such as caespitate, catechin, licochalcone A, and myricetin (Figure ) exhibit anticancer, antimalarial, and antioxidant properties. − While popular due to their natural abundance, chemical synthesis of these compounds often involves toxic solvents, expensive reagents, and long reaction times . Electrosynthesis provides a greener, faster, and less expensive alternative to carry out organic transformations under milder conditions …”

Section: Introductionmentioning

confidence: 99%

Mechanistic Insights into Electrocatalytic Carbon−Bromine Bond Cleavage in Polybrominated Phenols

McKenzie,

Hosseini,

Tanwar

et al. 2023

J. Phys. Chem. C

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Carbon−halogen bond cleavage has been studied extensively for many years as a simple electrosynthesis step in the formation of more complex natural products. Reduction of halogenated phenols has received less attention, in part, due to the lowered faradaic efficiency resulting from the competing hydrogen evolution reaction. Herein, we report the electroreduction of a series of brominated phenols through a homogeneous electrocatalytic (EC′) mechanism. Beginning with the structurally simple 2-bromophenol, we use foot-of-the-wave analysis to determine optimal catalysts. Nickel(II) salen requires the lowest overpotential for C−Br reduction and was used across all substrates. Chronoamperometric studies and density functional theory calculations were carried out to contribute to our understanding of the reduction mechanism. Next, the more complex 2,6-dibromophenol and tetrabromobisphenol-A are studied by means of cyclic voltammetry, chronoamperometry, and density functional theory. Through analysis of molecular orbitals diagrams, the more complex brominated phenols are found to undergo sequential carbon−bromine bond reduction, wherein the electrogenerated radical species accepts a second electron to form a carbanion before second carbon−bromine bond cleavage occurs.

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First Synthesis and Anti‐Inflammatory Effects of Puerariafuran and its Derivatives

Yoon

Kim

Jun

2015

Bulletin Korean Chem Soc

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The total synthesis of puerariafuran and its derivatives was achieved for the first time by the direct reaction between substituted α‐bromoacetophenones and resorcinol. The reaction was mediated by neutral alumina and was fully regio‐controlled. Subsequently, the Sonogashira coupling method was applied for puerariafuran preparation. Finally, the anti‐inflammatory effects of these prepared compounds were evaluated in lipopolysaccharide (LPS) stimulated RAW 264.7 macrophages. The results revealed that puerariafuran and its derivatives show weak inhibition activity on the production of inflammatory‐mediated nitric oxide.

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Concise Synthesis of Licochalcone A through Water-Accelerated [3,3]-Sigmatropic Rearrangement of an Aryl Prenyl Ether

Cited by 15 publications

References 5 publications

Histone Deacetylase GiSRT2 Negatively Regulates Flavonoid Biosynthesis in Glycyrrhiza inflata

Histone Deacetylase GiSRT2 Negatively Regulates Flavonoid Biosynthesis in Glycyrrhiza inflata

Mechanistic Insights into Electrocatalytic Carbon−Bromine Bond Cleavage in Polybrominated Phenols

First Synthesis and Anti‐Inflammatory Effects of Puerariafuran and its Derivatives

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