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Related Concept Videos

Acidity and Basicity of Carboxylic Acid Derivatives01:25

Acidity and Basicity of Carboxylic Acid Derivatives

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Carboxylic acids are the strongest among organic acids, as they readily lose the hydroxyl proton to form a resonance-stabilized carboxylate ion. In comparison, the acid derivatives lack acidic hydrogens directly attached to a functional group. In these compounds, the acidic nature arises from their ability to lose α hydrogens, making them weakly acidic.
The relative acidic strength of the derivatives can be explained based on the extent of resonance stabilization of the conjugate base. The...
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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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Bile01:19

Bile

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Bile is a crucial bodily fluid, characterized by its yellow-green color and alkaline nature. Produced in the liver, it is transported through the common hepatic duct into either the cystic duct, leading to the gallbladder, or directly into the common bile duct. The flow of bile is regulated by the sphincter of Oddi located at the entrance of the duodenum. When this sphincter is closed, bile is redirected to the gallbladder for storage and concentration.
Bile is released when dietary fats enter...
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Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

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Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
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Spectroscopy of Carboxylic Acid Derivatives01:26

Spectroscopy of Carboxylic Acid Derivatives

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Infrared spectroscopy is primarily used to determine the types of bonds and functional groups. In carboxylic acid derivatives, a typical carbonyl bond absorption is observed around 1650–1850 cm−1. For esters, the absorption is recorded at around 1740 cm−1, while acid halides show the absorption at about 1800 cm−1. Another acid derivative, the acid anhydrides, exhibit two carbonyl absorption around 1760 cm−1 and 1820 cm−1, arising from the symmetrical and...
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Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides01:16

Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides

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Naming Acid Halides
The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.
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Using Multi-fluorinated Bile Acids and In Vivo Magnetic Resonance Imaging to Measure Bile Acid Transport
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A bile acid derivative with PPARγ-mediated anti-inflammatory activity.

Sen Liu1, Ying Wang1, Mingzhi Su1

  • 1College of Pharmacy, Pusan National University, Busan 46241, Republic of Korea.

Steroids
|August 8, 2018
PubMed
Summary

A new steroid compound from jellyfish fungus Penicillium chrysogenum suppresses inflammation by activating PPARγ and inhibiting NF-κB signaling pathways.

Keywords:
Anti-inflammatory activityBile acid derivativesNF-κBPPARγ agonist

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Area of Science:

  • Natural Product Chemistry
  • Pharmacology
  • Immunology

Background:

  • Jellyfish-derived fungi are a source of novel bioactive compounds.
  • Inflammation is implicated in numerous diseases and targeted by various therapies.
  • Peroxisome proliferator-activated receptor gamma (PPARγ) is a therapeutic target for inflammatory conditions.

Purpose of the Study:

  • To isolate and characterize bioactive secondary metabolites from Penicillium chrysogenum.
  • To investigate the anti-inflammatory potential of isolated compounds.
  • To elucidate the molecular mechanism of action of the novel steroidal artifact.

Main Methods:

  • Isolation and structure elucidation of secondary metabolites using chromatographic and spectroscopic techniques.
  • In vitro anti-inflammatory assays using lipopolysaccharide (LPS)-induced RAW 264.7 macrophages.
  • Molecular docking analysis to predict ligand-receptor interactions.
  • Cell-based assays to assess PPARγ activation and NF-κB signaling pathway modulation.

Main Results:

  • A new steroidal artifact (1) and several bile acid derivatives were isolated from Penicillium chrysogenum.
  • Compound 1 demonstrated significant anti-inflammatory effects by suppressing nitric oxide (NO) production and pro-inflammatory gene expression (iNOS, TNF-α).
  • Docking analysis and cell-based assays revealed that compound 1 acts as a steroidal PPARγ activator, inhibiting the NF-κB signaling pathway.

Conclusions:

  • Compound 1, a novel steroidal artifact from jellyfish-derived fungus, possesses potent anti-inflammatory properties.
  • The anti-inflammatory mechanism involves the activation of PPARγ and subsequent suppression of the NF-κB signaling pathway.
  • This study highlights the potential of marine-derived fungi as a source of novel anti-inflammatory agents.