Гарденин

Description

Gardenin is an iridoid aglycone, a natural metabolite of gardenoside transformation by human intestinal microflora, also found as an independent iridoid in the herbs Nauclea officinalis. Chemical name: [2aS-(2aalpha,4aalpha,7aalpha,7balpha)]-2,2a,4a,7,7a,7b-hexahydro-2a-hydroxy-1-oxa-7-azacyclopent[cd]indene-5-carboxylic acid methyl ester.

Basic Attributes

• CAS No: 139682-36-3
• Chemical formula: C11H13NO4
• English name: gardenine
• Molecular weight: 223.22 g/mol
• Exact mass: 223.08445790 g/mol
• PSA specifications: 67.8 Å2

Compound class and origin

Gardenine belongs to nitrogen-containing iridoids - a rare subgroup of iridoid aglycones, in the structure of which the oxygen atom of the cyclopentapyran ring is partially replaced by nitrogen (1-oxa-7-aza-cyclopent[cd]indene system). This structure is formed in the human body during the bacterial transformation of gardenoside - a glycosidated iridoid from the fruits of Gardenia jasminoides - in the large intestine, where the intestinal microflora splits off the sugar residue and carries out further structural transformations. Gardenine is also found as a native metabolite in the herb Nauclea officinalis, a plant of the Rubiaceae family.

Biological activity and significance

As a product of gardenoside metabolism, gardenine is being considered in studies of the pharmacokinetics and bioavailability of gardenia iridoid glycosides—the compound is being used to understand which metabolites are formed in the human intestine after taking gardenia medications and how much of the therapeutic effect is due to gardenine itself rather than the parent glycoside.

Scope of application

Practical application - scientific research: gardenine is used as an analytical reference standard in the study of the metabolism of Gardenia jasminoides iridoid glycosides by intestinal microflora, as well as in the phytochemical analysis of Nauclea officinalis. The compound is not intended for direct medical use. Additionally, it is used in metabolomics studies as a marker compound, which allows confirming the fact of bacterial biotransformation of gardenia iridoid glycosides in the intestine and assessing the individual variability of such metabolism in different people.

Related compounds

In addition to gardenine, bacterial transformation of the iridoid glycosides of gardenia and related Madderaceae produces a number of structurally similar aglycones and further oxidation products, including garjasmine. The comparison of these metabolites is used to build a complete picture of the metabolic pathway of gardenoside in the human body.

Storage and transportation

Store in original sealed packaging, in a cool, dry place, protected from light, at +2...+8 °C; For long-term storage of reference standards, freezing at -20 °C is permissible. Transportation at a controlled temperature without sudden changes and moisture condensation inside the package. The batch is accompanied by a Certificate of Analysis (COA) confirming the purity of the substance.