Дегидроформурегин

Identification

Dehydroformuregine (English: DehydroforMouregine, Dehydroformouregine, CAS 107633-69-2) is an aporphine (oxidized aporphine) alkaloid. Chemical formula C20H19NO4. Systematic name by synonym: 4,5-dihydro-1,2,3-trimethoxy-6H-dibenzo[de,g]quinoline-6-carboxaldehyde - the name directly indicates the dibenzoquinoline (aporphine) skeleton of the molecule.

Physico-chemical characteristics

• Molecular Weight: 337.36916
• Exact weight: 337.131
• PSA characteristic: 48 Ų
• XLogP3: 3.7

There are no other parameters - density, melting points, boiling points, refractive index - in the original dump for this product, and they were not found in open sources during an additional search.

Natural spring

Information about the sources of the compound in public databases differs: some sources point to the isolation from the plant Piper nigrum (black pepper), others - from the lichen Tinctoria fibraurea. This discrepancy is typical of rare alkaloids described independently by different research groups and requires caution in stating the exact botanical origin without further verification.

Structural class

The dibenzo[de,g]quinoline skeleton is a characteristic numbering system for aporphine alkaloids, a tricyclic aromatic structure with an additional fused ring. Three methoxy groups at positions 1, 2, 3 and an aldehyde group at position 6 bring dehydroformuregine closer to oxoaporphine alkaloids such as lyriodenine.

Biological activity

It exhibits cytotoxic activity against human leukemia cells, inhibits the synthesis of RNA, protein and DNA - a mechanism of action typical of oxoaporphine alkaloids that can intercalate into DNA and disrupt the functioning of topoisomerases and polymerases.

Place among aporphine alkaloids

Aporphine and oxoaporphine alkaloids are widely distributed in plants of the Laurel, Magnolia, Rafflesia, Pepper and other families - they are united by a common biosynthetic pathway from benzylisoquinoline precursors through the oxidative combination of phenolic rings. Liriodenine, the closest structural relative of dehydroformuregin, has been well studied as an antitumor and antimicrobial compound, making comparison with it a useful starting point when assessing the potential of dehydroformuregin.

Meaning of discrepancy in source description

The discrepancies regarding the natural source - Piper nigrum plant or Tinctoria fibraurea lichen - illustrate a general problem in the phytochemistry of rare alkaloids: without repeated verification from independent samples, it is difficult to determine the exact botanical origin of a compound from literature data alone, and the chemical reagent market often inherits such uncertainties from earlier publications.

Storage

Aporphine alkaloids with an aldehyde group are sensitive to oxidation and light. Store in a container protected from light, in a cool, dry place.