The biochemistry and medical significance of the flavonoids.

http://www.beauty-review.nl/wp-content/uploads/2014/10/Some-phytochemical-pharmacological-and-toxicological-properties-of-ginger-Zingiber-officinale-Roscoe-A-review-of-recent-research.pdf

Some phytochemical, pharmacological and toxicological properties of ginger (Zingiber officinale Roscoe): a review of recent research.

Phytoestrogens: the biochemistry, physiology, and implications for human health of soy isoflavones.

Citrus Flavonoids: molecular structure, biological activity and nutritional properties: a review

The molecular basis of working mechanism of natural polyphenolic antioxidants

We studied the effects of apigenin and 2,4,5-trimethoxycinnamic acid (TMCA) on the behavioral despair test (forced swimming test), and the central noradrenergic, dopaminergic and serotonergic activities in mice. Apigenin at intraperitoneal doses of 12.5 and 25 mg/kg significantly decreased the duration of immobility in the forced swimming test in mice. At 100 mg/kg, the duration of immobility was returned to the control level in the test. On the other hand, TMCA treatment (25-200 mg/kg, i.p.) failed to significantly alter the duration of immobility. Based on the behavioral data, we examined changes in the monoamine turnover in mice having been subjected to forced swimming for 40 min. The monoamine turnover was measured in seven brain regions. Forced swimming exposure induced a significant decrease in dihydroxyphenylacetic acid (DOPAC)/dopamine (DA) in the striatum and amygdala and in 5-hydroxyindoleacetic acid (5-HIAA)/5-hydroxytriptamine (5-HT) in the hypothalamus, and a significant increase in DOPAC/DA in the thalamus and hypothalamus and in 3-methoxy-4-hydroxyphenylethyleneglycol (MHPG)/norepinephrine (NE) in the amygdala, frontal cortex, hypothalamus, and midbrain. Apigenin (25 mg/kg) treatment produced attenuation of forced swim test-induced decrease of DA turnover in the amygdala and increase of DA turnover in the hypothalamus. Furthermore, intraperitoneal administration of haloperidol (0.2 mg/kg), a dopamine D(2) antagonist, blocked the apigenin (25 mg/kg)-induced decrease in immobility in the forced swimming test. These behavioral and biochemical results indicate the antidepressant properties of apigenin, which may be mediated by the dopaminergic mechanisms in the mouse brain.

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Antidepressant-like effects of apigenin and 2,4,5-trimethoxycinnamic acid from Perilla frutescens in the forced swimming test.

The urine of rats administered rosmarinic acid (7) orally contained seven metabolites, which were identified as trans-caffeic acid 4-O-sulfate (1), trans-m-coumaric acid 3-O-sulfate (2), trans-ferulic acid 4-O-sulfate (3), trans-caffeic acid (4), m-hydroxyphenylpropionic acid (5), trans-m-coumaric acid (6), and unchanged rosmarinic acid (7) by spectroscopic and chemical data. The total cumulative amount of 1-7 excreted in the urine 48 h after the oral administration of rosmarinic acid was approximately 31.8% of the dose administered. On the other hand, the metabolites attributed to rosmarinic acid could not be found in the bile. Orally administered rosmarinic acid may thus be concluded to be excreted in the urine rather than in the bile, with cleavage of ester bonds, selective para-dehydroxylation, methylation, and sulfate-conjugation. Metabolites 2, 3, 5, and 6 were also detected in the plasma.

Metabolism of rosmarinic acid in rats

Metabolism of [6]-gingerol in rats.

Examination was made of the urinary and biliary excretion of metabolites of daidzin and daidzein, the major components of roots of Pueraria lobata Ohwi (Leguminosae) in rats. The urine of rats administered daidzin orally contained four major metabolites, daidzein 7,4'-di-O-sulfate (M-1), daidzein 7-O-beta-D-glucuronide (M-2), daidzein 4'-O-sulfate (M-3), daidzein (M-4), as determined from spectroscopic and chemical data. The urine of rats treated with daidzein contained M-2--M-4 in the above metabolites. Total cumulative amounts of the four metabolites excreted in the urine at 48 h following the oral administration of daidzin and daidzein were approximately 4.8% and 4.6% of the doses administered, respectively. The bile of rats administered daidzin orally contained M-1--M-4. Daidzein 7-O-beta-D-glucuronide 4'-O-sulfate (M-5), a major biliary metabolite, was identified by the high-performance liquid chromatography (HPLC), liquid chromatography-mass spectrometry (LC-MS) and nuclear magnetic resonance (NMR) spectra. At least daidzin appeared to be hydrolyzed to aglycone after absorption in the body, and as a part of metabolites, M-1--M-4 having free hydroxyl, glucuronided or sulfated hydroxyls at the C-7 position, may then be excreted in the urine and bile.

Urinary and Biliary Metabolites of Daidzin and Daidzein in Rats

As a part of our search for the active metabolite from the bark of Magnolia officinalis (Magnoliaceae), the aqueous extract was orally administered to rats, and metabolites in the urine were analysed by a high-performance liquid chromatograph equipped with a photodiode array detector. When the extract was given to rats, five metabolites (sinapic acid-4-O-sulfate (1), sinapic acid-4-O-beta-glucuronide (2), sinapic acid (3), 3-[2',6-dihydroxy-5'-(2-propenyl)[1,1'-biphenyl]-3-yl]-(E)-2-propenoic acid (4), and an unchanged form, magnolol (5)) were detected in the urine. It was revealed that metabolites 1-3 and 4 were respectively derived from syringin and magnolol contained in the extract. In a human urine sample, metabolites 3-5 and dihydroxydihydromagnolol (6) were detected. These structures were identified by a combination of spectral methods and/or by comparison with authentic compounds obtained by synthesis. Among these free form metabolites (3-6), acute treatments with magnolol and dihydroxydihydromagnolol (50-100 mg kg(-1), i.p.) attenuated the forced swim-induced experimental depression in mice. The results indicated that magnolol and dihydroxydihydromagnolol were the antidepressant constituents of Magnolia officinalis.

Keisuke Ohsawa

Papers

Antidepressant-like effects of apigenin and 2,4,5-trimethoxycinnamic acid from Perilla frutescens in the forced swimming test.

Metabolism of rosmarinic acid in rats

Metabolism of [6]-gingerol in rats.

Urinary and Biliary Metabolites of Daidzin and Daidzein in Rats

Metabolites of orally administered Magnolia officinalis extract in rats and man and its antidepressant‐like effects in mice