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2° Amines to N-Nitrosamines: Reaction with NaNO201:20

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Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
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Seed structures are composed of a protective seed coat surrounding a plant embryo, and a food store for the developing embryo. The embryo contains the precursor tissues for leaves, stem, and roots. The endosperm and cotyledons—seed leaves—act as the food reserves for the growing embryo.
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Living cells constantly carry out various chemical reactions which are necessary for their proper functioning. These reactions are interlinked to one another via multiple pathways. The collection of these chemical reactions is known as metabolism.
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Overview of Nitrogen Metabolism01:20

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Nitrogen is a very important element for life because it is a major constituent of proteins and nucleic acids. It is a macronutrient, and in nature, it is recycled from organic compounds and stored in the form of  ammonia, ammonium ions, nitrate, nitrite, or  nitrogen gas by many metabolic processes. Many of these metabolic processes are carried out only by prokaryotes.
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Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
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Amines: Introduction01:07

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Amines are organic derivatives of ammonia. They are formed by replacing one or more ammonia protons with alkyl or aryl groups. Depending upon the number of organyl groups bonded to nitrogen, amines are classified as primary, secondary, or tertiary. Primary amines have one organyl group attached to the nitrogen atom, while secondary and tertiary amines have two and three organyl groups attached to the nitrogen atom, respectively.
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Author Spotlight: A Tailor-Made Sample Preparation Approach for Enhanced MALDI-IMS Analysis of Hard Palm Seeds
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Nitrogenous compounds from Aesculus wilsonii seeds.

Huina Cao1, Jingya Ruan2, Xiaoyan Cao1

  • 1Tianjin Key Laboratory of TCM Chemistry and Analysis, Tianjin University of Traditional Chinese Medicine, Tianjin 301617, China.

Fitoterapia
|December 18, 2023
PubMed
Summary

Researchers isolated eight nitrogenous compounds from Aesculus wilsonii seeds, discovering five new ones. Compounds 2 and 8 showed significant anti-inflammatory effects by inhibiting nitric oxide production.

Keywords:
NO production inhibitionNitrogenous compoundsThe seeds of Aesculus wilsonii Rehd

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Area of Science:

  • Natural Product Chemistry
  • Pharmacology

Background:

  • The seeds of Aesculus wilsonii are a potential source of novel bioactive compounds.
  • Nitrogenous compounds are known for diverse biological activities.

Purpose of the Study:

  • To isolate and characterize nitrogenous compounds from Aesculus wilsonii seeds.
  • To evaluate the anti-inflammatory potential of the isolated compounds.

Main Methods:

  • Isolation and purification using chromatographic techniques.
  • Structure elucidation via spectroscopic methods (NMR, ECD) and chemical reactions.
  • In vitro anti-inflammatory assay using lipopolysaccharide (LPS)-induced nitric oxide production in RAW264.7 macrophages.

Main Results:

  • Eight nitrogenous compounds were isolated, including five novel compounds: aeswilnitrousol A (1), aeswilnitrousosides BD (2-4), and 6-(2-hydroxy-3-methylbutylamino)-8-oxoadenine (5).
  • Compounds 7 and 8 were reported from the Aesculus genus for the first time, and compound 6 was isolated from this plant initially.
  • Compounds 2 and 8 demonstrated concentration-dependent inhibition of nitric oxide production at 10, 25, and 50 μM, indicating anti-inflammatory activity.

Conclusions:

  • The study successfully identified new nitrogenous compounds from Aesculus wilsonii seeds.
  • Compounds 2 and 8 possess notable anti-inflammatory properties, warranting further investigation.