Stability of monoHER in an aqueous formulation for i.v. administration

Hassan, Mohamed; Touw, Daan; Wilhelm, Anne; Bast, Aalt; Vijgh, W.J.F. van der

doi:10.1016/s0378-5173(00)00587-1

Cited by 9 publications

(6 citation statements)

References 8 publications

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“…This may have led to a lower deodorizing effect, especially for mint juice. Phenolic compounds are unstable and may exist as monomers or polymers (Abou El hassan and others ; Zhu and others ; Friedman and Jürgens 2008). Breaking the cell matrix of the food compounds exposes the phenolic compounds to oxidation particularly in the presence of PPO.…”

Section: Resultsmentioning

confidence: 99%

Deodorization of Garlic Breath by Foods, and the Role of Polyphenol Oxidase and Phenolic Compounds

Mirondo

Barringer

2016

Journal of Food Science

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Garlic causes a strong garlic breath that may persist for almost a day. Therefore, it is important to study deodorization techniques for garlic breath. The volatiles responsible for garlic breath include diallyl disulfide, allyl mercaptan, allyl methyl disulfide, and allyl methyl sulfide. After eating garlic, water (control), raw, juiced or heated apple, raw or heated lettuce, raw or juiced mint leaves, or green tea were consumed immediately. The levels of the garlic volatiles on the breath were analyzed from 1 to 60 min by selected ion flow tube mass spectrometry (SIFT-MS). Garlic was also blended with water (control), polyphenol oxidase (PPO), rosemarinic acid, quercetin or catechin, and the volatiles in the headspace analyzed from 3 to 40 min by SIFT-MS. Raw apple, raw lettuce, and mint leaves significantly decreased all of the garlic breath volatiles in vivo. The proposed mechanism is enzymatic deodorization where volatiles react with phenolic compounds. Apple juice and mint juice also had a deodorizing effect on most of the garlic volatiles but were generally not as effective as the raw food, probably because the juice had enzymatic activity but the phenolic compounds had already polymerized. Both heated apple and heated lettuce produced a significant reduction of diallyl disulfide and allyl mercaptan. The presence of phenolic compounds that react with the volatile compounds even in the absence of enzymes is the most likely mechanism. Green tea had no deodorizing effect on the garlic volatile compounds. Rosmarinic acid, catechin, quercetin, and PPO significantly decreased all garlic breath volatiles in vitro. Rosmarinic acid was the most effective at deodorization.

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Section: Resultsmentioning

confidence: 99%

Deodorization of Garlic Breath by Foods, and the Role of Polyphenol Oxidase and Phenolic Compounds

Mirondo

Barringer

2016

Journal of Food Science

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“…[1][2][3][4][5][6][7] Many of these compounds are already used in pharmaceutical, cosmetic, and food preparations. 4,[8][9][10][11][12][13] However, their solubility is very low in water, 8,10,[14][15][16] being about (0.12, 0.5, < 0.01, and 0.4) g‚L -1 at 20 °C for rutin, naringin, quercetin, and neohesperidine dihydrochalcone, respectively. [17][18][19] The solubility also depends on the pH.…”

Section: Introductionmentioning

confidence: 99%

Solubility of Flavonoids in Organic Solvents

et al. 2007

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The solubility of quercetin, isoquercitrin, rutin, chrysin, naringenin, and hesperetin was quantified in acetonitrile, acetone, and tert-amyl alcohol. The solubility was strongly affected by both the nature of the solvent and the flavonoid structure. The highest solubility was obtained in acetonitrile for hesperetin (85 mmol·L-1) and naringenin (77 mmol·L-1) and in acetone (80 mmol·L-1) for quercetin. The lowest solubility value was obtained with rutin in acetonirile (0.50 mmol·L-1). The thermodynamic properties of flavonoids were also measured (melting point, enthalpy of fusion, and solid heat capacity) and predicted (liquid heat capacity, solid phase activity, and activity coefficient). Glycosylated flavonoids are characterized by a low melting point and a high enthalpy of fusion compared to the aglycon ones. Contrary to the data reported for other compounds, there is no clear correlation between the solubility of flavonoids and their thermodynamic properties. However, the conformational study showed that the flavonoids having a torsion angle OC2C1‘C6‘ of 40° are characterized by a high solubility.

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“…The final solution was filtered through a 0.2‐µm filter. The solution is chemically stable for at least 24 h at room temperature, 41 and therefore the volunteers received the drug within 24 h after preparation. MonoHER was administered as an intravenous infusion for 15 min at a dose of 1,500 mg/m 2 .…”

Section: Methodsmentioning

confidence: 99%

Differences in Pharmacological Activities of the Antioxidant Flavonoid MonoHER in Humans and Mice Are Caused by Variations in Its Metabolic Profile

Jacobs

Koek

Peters

et al. 2011

Clin Pharmacol Ther

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Despite its well-known cardiotoxicity, the anthracycline doxorubicin continues to be a widely used chemotherapeutic agent. The flavonoid 7-mono-O-(β-hydroxyethyl)-rutoside (monoHER) has shown protection against doxorubicin-induced cardiotoxicity in mice. However, this protection has not been observed in humans. This prompted us to investigate monoHER metabolism in humans and compare it with that in mice. Five healthy volunteers received monoHER by intravenous infusion. After infusion, bile fluid was collected, and the monoHER metabolites were identified by liquid chromatography-diode-array detection (LC-DAD), time-of-flight mass spectrometry (TOF-MS), and (1)H-nuclear magnetic resonance (NMR). Thirteen different metabolites were identified. MonoHER was predominantly converted into inactive glucuronidated metabolites. In mice, the major metabolic route is methylation, which forms bioactive metabolites that are implicated in the cardioprotective effect of monoHER. This indicates that the different pharmacological effects of monoHER in mice and humans might be explained by a difference in monoHER metabolism. This study adds to the growing appreciation of flavonoid metabolites as bioactive compounds.

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Stability of monoHER in an aqueous formulation for i.v. administration

Cited by 9 publications

References 8 publications

Deodorization of Garlic Breath by Foods, and the Role of Polyphenol Oxidase and Phenolic Compounds

Deodorization of Garlic Breath by Foods, and the Role of Polyphenol Oxidase and Phenolic Compounds

Solubility of Flavonoids in Organic Solvents

Differences in Pharmacological Activities of the Antioxidant Flavonoid MonoHER in Humans and Mice Are Caused by Variations in Its Metabolic Profile

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