Isorhamnetin 3-glucuronide
Isorhamnetin 3 -O -glucuronide exerts anti-inflammatory activity by increasing heme oxygenase-1 (HO-1) expression and by suppressing Jun N-terminal kinase (JNK) and p38 signaling pathways in LPS-challenged RAW264.7 macrophage cells. Isorhamnetin 3-glucuronide can inhibit vascular cell adhesion molecule-1 (VCAM-1) cell surface expression at 2 micromol/L, indicates that it can inhibit the expression of key molecules involved in monocyte recruitment during the early stages of atherosclerosis at physiological concentrations. It (1 mg/kg i.v.) can progressively reduce mean blood pressure (MBP), measured in conscious spontaneously hypertensive rats (SHR).
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Plos One, 2012, 7(3):e32673.
Glucuronidated quercetin lowers blood pressure in spontaneously hypertensive rats via deconjugation.[Pubmed:
22427863 ]
METHODS AND RESULTS:
We have analyzed the effects on blood pressure and vascular function in vitro of the conjugated metabolites of quercetin (quercetin-3-glucuronide, Q3GA; Isorhamnetin 3-glucuronide, I3GA; and quercetin-3'-sulfate, Q3'S) in spontaneously hypertensive rats (SHR). Q3GA and I3GA (1 mg/kg i.v.), but not Q3'S, progressively reduced mean blood pressure (MBP), measured in conscious SHR. The hypotensive effect of Q3GA was abolished in SHR treated with the specific inhibitor of β-glucuronidase, saccharic acid 1,4-lactone (SAL, 10 mg/ml). In mesenteric arteries, unlike quercetin, Q3GA had no inhibitory effect in the contractile response to phenylephrine after 30 min of incubation. However, after 1 hour of incubation Q3GA strongly reduced this contractile response and this effect was prevented by SAL. Oral administration of quercetin (10 mg/Kg) induced a progressive decrease in MBP, which was also suppressed by SAL. Conjugated metabolites are involved in the in vivo antihypertensive effect of quercetin, acting as molecules for the plasmatic transport of quercetin to the target tissues.
CONCLUSIONS:
Quercetin released from its glucuronidated metabolites could be responsible for its vasorelaxant and hypotensive effect.
Tetrahedron Volume 62, Issue 29, 17 July 2006, Pages 6862–6868
Convenient syntheses of metabolically important quercetin glucuronides and sulfates[Reference:
WebLink]
METHODS AND RESULTS:
Synthetic approaches to the major human plasma metabolites of quercetin, quercetin 3′-sulfate and the β-d-glucopyranosiduronic acid derivatives 3′-methylquercetin 3-glucuronide (Isorhamnetin 3-glucuronide), quercetin 3-glucuronide and quercetin 3′-glucuronide are described.
CONCLUSIONS:
This is the first report of the chemical synthesis of quercetin 3′-glucuronide. All procedures start from the same precursor, 4′,7-di-O-benzylquercetin, and all are more convenient than existing methods.
