Microwave-Mediated Synthesis of Anticarcinogenic Isoflavones from Soybeans

Chang, Yu-Tang; Nair, Muraleedharan G.; Santell, Ross; Helferich, William G.

doi:10.1021/jf00045a007

Cited by 99 publications

(73 citation statements)

References 15 publications

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“…Daidzein and 2,4,4 0 -trihydroxydeoxybenzoin (THB) were synthesized using the method of Song et al (17). Genistein was synthesized according to a modification of the method of Chang et al (18). HPLC grade acetonitrile, methanol, acetic acid, dimethyl sulfoxide (DMSO), and all other chemicals were from Fisher Scientific (Fair Lawn, NJ).…”

Section: Methodsmentioning

confidence: 99%

Greater Apparent Absorption of Flavonoids Is Associated with Lesser Human Fecal Flavonoid Disappearance Rates

Simons

Renouf

Murphy

et al. 2009

J. Agric. Food Chem.

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It was hypothesized that 5,7,4 0 -OH-flavonoids disappeared more rapidly from human fecal incubations and were less absorbable by humans than flavonoids without 5-OH moieties. Anaerobic fecal disappearance rates over 24 h were determined for 15 flavonoids in samples from 20 men and 13 women. In these anaerobic fecal mixtures, flavonoids with 5,7,4 0 -OH groups, genistein, apigenin, naringenin, luteolin, kaempferol, and quercetin (disappearance rate, k = 0.46 ( 0.10 h -1 ), and methoxylated flavonoids, hesperetin and glycitein (k = 0.24 ( 0.21 h -1 ), disappeared rapidly compared with flavonoids lacking 5-OH (e.g., daidzein, k = 0.07 ( 0.03 h -1 ). Apparent absorption of flavonoids that disappeared rapidly from in vitro fecal incubations, genistein, naringenin, quercetin, and hesperetin, was compared with that of daidzein, a slowly disappearing flavonoid, in 5 men and 5 women. Subjects ingested 104 μmol of genistein and 62 μmol of daidzein (soy milk), 1549 μmol of naringenin and 26 μmol of hesperetin (grapefruit juice), and 381 μmol of quercetin (onions) in three test meals, each separated by 1 week. Blood and urine samples were collected over 24 h after each test meal. Plasma flavonoid concentrations ranged from 0.01 to 1 μM. The apparent absorption, expressed as percentage of ingested dose excreted in urine, was significantly less for naringenin (3.2 ( 1.7%), genistein (7.2 ( 4.6%), hesperetin (7.3 ( 3.2%), and quercetin (5.6 ( 3.7%) compared with daidzein (43.4 ( 15.5%, p = 0.02). These data affirmed the hypothesis that the 5,7,4 0 -OH of flavonoids limited apparent absorption of these compounds in humans.

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Section: Methodsmentioning

confidence: 99%

Greater Apparent Absorption of Flavonoids Is Associated with Lesser Human Fecal Flavonoid Disappearance Rates

Simons

Renouf

Murphy

et al. 2009

J. Agric. Food Chem.

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“…1). 10,11) Compounds 1-24 (Fig. 1) were synthesized successfully, and their chemical identity and purity were confirmed by spectral data ( 1 H-and 13 C-NMR, and mass), as summarized above in ''Materials and Methods.''…”

Section: Resultsmentioning

confidence: 93%

Discovery of Novel 2′,3′,4′-Trihydroxy-2-phenylacetophenone Derivatives as Anti-Gram-Positive Antibacterial Agents

Goto

Kumada

Ashida

et al. 2009

Bioscience, Biotechnology, and Biochemistry

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“…Major fractions were purified by HPLC-RI (Waters 590 series pumping system equipped with a Waters R401 refractive index detector) in isocratic elution mode using Luna C8 column (250 x 10 mm, 10 µm) (methanol-water 55:45 v/v), both from Phenomenex (Torrance, CA, USA), to yield pure compounds, which were identified as isomeric mixture of guttiferone E and xanthocymol (1) (Gustafson et al, Inhibition of Saccharomyces cerevisiae Pdr5p by a natural compound extracted from Brazilian Red Propolis Cinzia Lotti et al 1992), 7-O-methylvestitol (2) (Piccinelli et al, 2005), vestitol (3) (Piccinelli, 2005), biochanin A (4) (Chang et al, 1994), and formononetin (Chang et al, 1994) …”

Section: Isolation Of Compoundsmentioning

confidence: 99%

Inhibition of Saccharomyces cerevisiae Pdr5p by a natural compound extracted from Brazilian Red Propolis

Lotti¹,

Castro²,

Sá³

et al. 2011

Rev. bras. farmacogn.

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Multidrug resistance of cancer cells and pathogenic microorganisms leading to the treatment failure of some forms of cancer or life-threatening bacterial or fungal infections is often caused by the overexpression of multidrug efflux pumps belonging to the ATP-binding cassette transporters superfamily. The multidrug resistance of fungal cells often involves the overexpression of efflux pumps belonging to the pleiotropic drug resistance (PDR) family of ABC transporters. Possibly the best-studied fungal PDR transporter is the multidrug resistance transporter Pdr5p of Saccharomyces cerevisiae. Some research groups have been searching for new inhibitors of these efflux pumps in order to alleviate resistance. Natural products are a great source for the discovery of new compounds with biological activity. Propolis is a complex resinous material collected by honeybees from exudates and buds of certain plant sources and this material is thought to serve as a defense substance for bee hives. Propolis is widely used in traditional medicine and is reported to have a broad spectrum of pharmacological properties. Literature reported some biological functionalities of propolis, such as antibacterial, antiviral, fungicidal, antiinflammatory and anti-carcinogenic activities. The chemical composition of propolis is qualitatively and quantitatively variable. Components isolated from methanolic extract of red Brazilian propolis (Alagoas, Northeast of Brazil) are isoflavonoids (including pterocarpans, isoflavans, isoflavones), flavanones and polyprenylated benzophenones. In this work we demonstrated the effects of five different isolated compounds on the ATPase activity of Pdr5p. Out of all five substances tested, only BRP-1 was able to completely abolish the enzymatic activity while others worked as positive modulators of the enzyme activity. BRP-1also inhibited the efflux of Rhodamine 6G from yeast cells overexpressing Pdr5p. Taken together, these results demonstrate that Brazilian propolis could be a source of promising compounds that can alleviate the MDR phenomenon, particularly in some fungi, where it could be used as an adjuvant for the treatment with azoles.

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Microwave-Mediated Synthesis of Anticarcinogenic Isoflavones from Soybeans

Cited by 99 publications

References 15 publications

Greater Apparent Absorption of Flavonoids Is Associated with Lesser Human Fecal Flavonoid Disappearance Rates

Greater Apparent Absorption of Flavonoids Is Associated with Lesser Human Fecal Flavonoid Disappearance Rates

Discovery of Novel 2′,3′,4′-Trihydroxy-2-phenylacetophenone Derivatives as Anti-Gram-Positive Antibacterial Agents

Inhibition of Saccharomyces cerevisiae Pdr5p by a natural compound extracted from Brazilian Red Propolis

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