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Related Concept Videos

Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
Sulfur Assimilation01:20

Sulfur Assimilation

Sulfur is an essential element in biological systems, contributing to synthesizing key biomolecules, including amino acids such as cysteine and methionine, and cofactors such as coenzyme A and biotin. Microorganisms primarily assimilate sulfur as sulfate (SO₄²⁻) from the environment, which must undergo a series of biochemical transformations before it can be incorporated into cellular components. As sulfate is highly oxidized, it must undergo assimilatory sulfate reduction to become...
Phase II Reactions: Sulfation and Conjugation with α-Amino Acids01:19

Phase II Reactions: Sulfation and Conjugation with α-Amino Acids

Sulfation and α-amino acid conjugation are two critical biotransformation reactions in drug metabolism. Sulfation, a phase II biotransformation reaction, involves adding a polar sulfate group to a drug, enhancing its water solubility and promoting excretion. This process can either co-occur with or occur independently of glucuronidation. Nonmicrosomal sulfotransferase enzymes catalyze the process. The reaction involves 3'-phosphoadenosine-5'-phosphosulfate or PAPS coenzyme activation, sulfur...
Phase II Reactions: Miscellaneous Conjugation Reactions01:19

Phase II Reactions: Miscellaneous Conjugation Reactions

Phase II biotransformations are detoxification mechanisms that conjugate xenobiotics with endogenous substances, neutralizing their toxicity.
A key example involves the conjugation of cyanide ions, which impair cellular respiration and alter hemoglobin into non-oxygen-carrying cyanmethemoglobin. To neutralize this threat, a sulfur atom from thiosulphate is transferred to the cyanide ion, catalyzed by the enzyme rhodanese, resulting in an inactive compound called thiocyanate. The production of...
Amines to Sulfonamides: The Hinsberg Test01:23

Amines to Sulfonamides: The Hinsberg Test

The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with benzenesulfonyl chloride, also known as the Hinsberg reagent, in the presence of an excess of aqueous base, followed by acidification. Based on the nature of the amines, different changes are observed.
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing sulfonyl...
Phase II Reactions: Methylation Reactions01:17

Phase II Reactions: Methylation Reactions

Methylation is a phase II biotransformation process involving the attachment of a methyl group to a substrate. Enzymes known as methyltransferases orchestrate this reaction.
The mechanism of methylation unfolds in two stages. The first stage sees a methyltransferase enzyme facilitating the transfer of a methyl group from S-adenosylmethionine (SAM) to the substrate, forming S-adenosylhomocysteine (SAH). The second stage involves further metabolism of SAH into homocysteine, which can be recycled...

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An Efficient Method for the Synthesis of Peptoids with Mixed Lysine-type/Arginine-type Monomers and Evaluation of Their Anti-leishmanial Activity
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Sulfur-containing amides from Entada phaseoloides.

Hui Xiong1, Er Xiao, Ying-Hong Zhao

  • 1College of Pharmacy, South-Central University for Nationalities, Wuhan 430074, China.

Yao Xue Xue Bao = Acta Pharmaceutica Sinica
|October 12, 2010
PubMed
Summary
This summary is machine-generated.

Researchers identified four sulfur-containing amide compounds from Entada phaseoloides seeds, including a novel compound and one previously undiscovered in the Entada genus. This study enhances our understanding of the plant

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Area of Science:

  • Phytochemistry
  • Natural Product Chemistry
  • Organic Chemistry

Background:

  • Entada phaseoloides (L.) Merr. is a plant species with potential medicinal properties.
  • Understanding its chemical constituents is crucial for exploring its pharmacological applications.

Purpose of the Study:

  • To isolate and characterize the chemical constituents present in the seeds of Entada phaseoloides.
  • To identify novel compounds and expand the known chemical diversity of the Entada genus.

Main Methods:

  • Extraction of seeds using 70% ethanol at room temperature.
  • Purification using silica gel and reversed-phase silica gel column chromatography.
  • Structure elucidation via spectral analysis and semi-preparative High-Performance Liquid Chromatography (HPLC).

Main Results:

  • Four sulfur-containing amide compounds were successfully isolated from the n-BuOH-soluble fraction.
  • The identified compounds are entadamide A-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranoside (1), entadamide A (2), entadamide A-beta-D-glucopyranoside (3), and clinacoside C (4).
  • Compound 1 represents a new chemical entity, and compound 4 is reported from the Entada genus for the first time.

Conclusions:

  • The chemical investigation of Entada phaseoloides seeds yielded four unique sulfur-containing amide compounds.
  • The discovery of a new compound and the first isolation of clinacoside C from this genus contribute significantly to natural product chemistry.
  • These findings provide a basis for further research into the biological activities and potential applications of these compounds.