HARMANE

Description

Chrysin (on the left) and harman (right) are organic compounds with distinctly different structures, but both are found in the passionflower species Passiflora caerulea and P. incarnata.
Chrysin, also called 5,7-dihydroxyflavone, was first isolated from the wood of pine trees (Pinus spp.) in 1949 by G?sta Linstedt at the KTH Royal Institute of Technology (Stockholm). Harman (or harmane), a pyridoindole derivative, was discovered much earlier (1861) in the bark of P. incarnata and other trees by German researcher R. Rieth.
What do chrysin and harman have in common besides occurrence in trees, specifically P. incarnata? More than 500 passionflower species have been used as traditional folk remedies for anxiety and other medical conditions almost everywhere that they grow on Earth. For at least 20 years, drug researchers have sought to elucidate mechanisms by which passionflower biochemicals provide relief.
In a key 2001 study, P. incarnata extract was compared with oxazepam, an early benzodiazepine anxiolytic drug, for efficacy against generalized anxiety disorder (GAD). Shaheen Akhondzadeh and colleagues at the Tehran University of Medical Sciences and the Institute of Medicinal Plants (both in Tehran, Iran) treated 36 patients diagnosed with GAD with P. incarnata extract, oxazepam, or placebo in a 4-week trial.
The extract and the drug gave equally positive results. Oxazepam acted more rapidly, but it also impaired the subjects’ job performance whereas the extract did not. In the time since this report was issued, however, there is no record of US Food and Drug Administration filings for chrysin, harman, or passionflower extracts.
This discussion of anxiety remedies reminds us that today is the beginning of Mental Health Awareness Week.

Chemical properties

Off-White Solid

The Uses of HARMANE

Harman alkaloid like harmane, harmine, harmalol, harmaline obtained from Banisteriopsis caapi L. showed cytotoxicity, antimicrobial activity against Staphylococcus aureus, Escherichia coli, Proteus vulgaris and Candida albicans.

The Uses of HARMANE

• Harmane was used in trace level determination of harmane by planar chromatography coupled with (tandem) mass spectrometry.
• It was used to study interactions of norharman and harman with DNA.
• It may be used as matrix for analysis of cyclodextrins and for sulfated oligosaccharides in combination with DHB as co-matrix.

What are the applications of Application

Harmane is an endogenous MAO-A and -B inhibitor (Order -CW for certified weight, analytical data, etc.)

Definition

ChEBI: An indole alkaloid fundamental parent with a structure of 9H-beta-carboline carrying a methyl substituent at C-1. It has been isolated from the bark of Sickingia rubra, Symplocus racemosa, P ssiflora incarnata, Peganum harmala, Banisteriopsis caapi and Tribulus terrestris, as well as from tobacco smoke. It is a specific, reversible inhibitor of monoamine oxidase A.

Synthesis Reference(s)

The Journal of Organic Chemistry, 37, p. 1429, 1972 DOI: 10.1021/jo00974a030
Tetrahedron, 49, p. 3325, 1993 DOI: 10.1016/S0040-4020(01)90161-9

General Description

• Harmane is a potent tremor-producing β-carboline alkaloid and neurotoxin.
• It is major representative of heterocyclic aromatic amines, a group of mutagenic and carcinogenic substances which are formed in meat from the precursors creatine, creatinine, amino acids and sugars during the heating at high temperatures.
• Blood harmane concentration is elevated in essential tremor, late-life neurological disease.

Biological Activity

Proposed as the endogenous ligand for imidazoline binding sites. Binds to I 1 -sites in rat kidney with an IC 50 of 31 nM, and I 2 -sites with a K i of 49 nM. In vivo, produces a dose-dependent hypotension that is reversed by efaroxan (2-(2-Ethyl-2,3-dihydro-2-benzofuranyl)-4,5-dihydro-1H-imidazole hydrochloride ). Also a potent inhibitor of monoamine oxidases A and B (I 50 values are 0.5 and 5 μ M respectively).

Biochem/physiol Actions

I1 imidazoline binding site agonist.

storage

Room temperature