GénistéineGenistein

Formula

C₁₅H₁₀O₅

Molar mass

270.24 g·mol⁻¹

CAS

446-72-0

PubChem CID

5280961

Origin

An isoflavone of plant origin, present mainly in soya and other legumes, where it circulates as a glycoside. It is supplied by the diet, in highly variable quantities according to culinary habits, and it is produced industrially as a research reagent and as a food supplement ingredient.

InChIKey

TZBJGXHYKVUXJN-UHFFFAOYSA-N

Editorial estimate, not clinical.

Genistein is the major isoflavone of soya, known for its oestrogenic activity and long used in the laboratory as an inhibitor of tyrosine kinases, and on that account used to block caveolae-dependent endocytosis. It is that instrumental use that brought it into the endocannabinoid literature: it had been observed that it reduced the uptake of anandamide by basophilic leukaemia cells, and it was concluded that this uptake passed through endocytosis. Thors, Eriksson and Fowler dismantled that reading in 2007. They first recalled that the molecule is also a competitive inhibitor of fatty acid amide hydrolase, the enzyme that hydrolyses anandamide. They then showed that daidzein, a neighbouring isoflavone devoid of action on tyrosine kinases, produces exactly the same effect on uptake, and that this effect is observed only in the lines where the reference inhibitor URB597 also acts, that is those whose uptake is genuinely carried by the enzyme. The conclusion is that blockade of the amide hydrolase, and not that of endocytosis, is the main determinant of the effect of genistein on anandamide uptake. That result has a reach beyond the molecule: it illustrates how far the interpretation of a pharmacological tool depends on the totality of its target profile, and it helped to reorient the debate on the existence of a membrane transporter for anandamide.

An isoflavone arising from the phenylpropanoid route, with an additional step proper to legumes. The flavanone naringenin, formed as in other plants by chalcone synthase, undergoes a migration of the phenyl ring from position 2 to position 3 under the action of an isoflavone synthase, a rearrangement reaction that defines the isoflavone class. That route bears no relation to the biosynthesis of the cannabinoids.

Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.

Class

ECS modulator (research)

Origin

An isoflavone of plant origin, present mainly in soya and other legumes, where it circulates as a glycoside. It is supplied by the diet, in highly variable quantities according to culinary habits, and it is produced industrially as a research reagent and as a food supplement ingredient.

Status

Unscheduled

1. 1.Thors et coll. 2007 : inhibition de la captation cellulaire de l'anandamide par la génistéine et la daidzéinePMID 17676056
2. 2.Thors et coll. 2008 : inhibition de la FAAH par le kaempférol et des flavonoïdes naturels apparentésPMID 18552875