Preliminary Pharmacology of Ellagic Acid From Juglans nigra (Black Walnut)

Bhargava, Umesh C.; Westfall, B. A.; Siehr, Donald J.

doi:10.1002/jps.2600571021

Cited by 23 publications

(14 citation statements)

References 4 publications

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“…Ellagic acid is pharmacologically active and has been found to control hemorrhage in animals (34,35) and humans (36,37), presumably by activating the intrinsic blood coagulation system (38). Hypotensive and sedative effects of ellagic acid have also been reported in rodents (39). Rats fed ellagic acid at a dose of 50 mg/kg per day for up to 45 days did not show any evidence of toxicity (40), and doses of ellagic acid of 0.2 mg/kg, intravenously, were well tolerated in humans (37).…”

Section: Discussionmentioning

confidence: 99%

Inhibition of the mutagenicity of bay-region diol epoxides of polycyclic aromatic hydrocarbons by naturally occurring plant phenols: Exceptional activity of ellagic acid

Wood

Huang

Chang

et al. 1982

Proc. Natl. Acad. Sci. U.S.A.

203

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Ferulic, caffeic, chlorogenic, and ellagic acids, four naturally occurring plant phenols, inhibit the mutagenicity and cytotoxicity of (+)-7,8,8a-dihydroxy-9a,10a-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (B[a]P 7,8-diol-9,10-epoxide-2), the only known ultimate carcinogenic metabolite of benzo [a]pyrene. The mutagenicity of 0.05 nmol of B[a]P 7,8-diol-9,10-epoxide-2 in strain TA100 of Salmonella typhimurium is inhibited 50% by incubation ofthe bacteria and the diol epoxide with 150 nmol offerulic acid, 75 nmol of caffeic acid, 50 nmol of chlorogenic acid or, most strikingly, 1 nmol of ellagic acid in the 0.5-ml incubation mixture. A 3-nmol dose of ellagic acid inhibits mutation induction by 90%. Ellagic acid is also a potent antagonist of B[a]P 7,8-diol-9,10-epoxide-2 in Chinese hamster V79 cells. Mutations to 8-azaguanine resistance induced by 0.2 ,AM diol epoxide are reduced by 50% when tissue culture media also contains 2 ,uM ellagic acid. Similar to results obtained with the bacteria, ferulic, caffeic, and chlorogenic acids are approximately two orders of magnitude less active than ellagic acid in the mammalian cell assay. The antimutagenic effects of the plant phenols result from their direct interaction with B[a]P 7,8-diol-9,10-epoxide-2, because a concentration-dependent increase in the rate ofdiol epoxide disappearance in cell-free solutions of 1:9 dioxane/water, pH 7.0, is observed with all four phenols. In parallel with the mutagenicity studies, ellagic acid is 80-300 times more effective than the other phenols in accelerating the disappearance of B[a]P 7,8-diol-9,10-epoxide-2. Ellagic acid at 10 ,M increases the disappearance of B[a]P 7,8-diol-9,10-epoxide-2 by approximately 20-fold relative to the spontaneous and hydronium ion-catalyzed hydrolysis of the diol epoxide at pH 7.0. Ellagic acid is a highly potent inhibitor of the mutagenic activity of bay-region diol epoxides of benzo[a]pyrene, dibenzo[a,h]pyrene, and dibenzo[a,ijpyrene, but higher concentrations of ellagic acid are needed to inhibit the mutagenic activity of the chemically less reactive bay-region diol epoxides of benz [a]anthracene, chrysene, and benzo [c]phenanthrene. These studies demonstrate that ellagic acid is a potent antagonist of the adverse biological effects of the ultimate carcinogenic metabolites of several polycyclic aromatic hydrocarbons and suggest that this naturally occurring plant phenol, normally ingested by humans, may inhibit the carcinogenicity ofpolycyclic aromatic hydrocarbons.Polycyclic aromatic hydrocarbons are relatively inert environmental precarcinogens that must be metabolized by mammalian enzymes to their biologically active products (ultimate carcinogens). Mutagenicity, metabolism, DNA-binding, and tumorigenicity studies during the past 8 years have shown that benzoring diol epoxides, in which the epoxide moiety forms part of the bay region (1, 2) of the hydrocarbons, are ultimate carcinogens of polycyclic hydrocarbons (3-6).Chemical and kinetic studies have demonstrated that bayregion diol epoxid...

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Section: Discussionmentioning

confidence: 99%

Inhibition of the mutagenicity of bay-region diol epoxides of polycyclic aromatic hydrocarbons by naturally occurring plant phenols: Exceptional activity of ellagic acid

Wood

Huang

Chang

et al. 1982

Proc. Natl. Acad. Sci. U.S.A.

203

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“…Jamun fruits and seeds are sweet, acrid and sour and they are used for treatment and control of diabetes, diarrhoea and ringworm. It is also reported to be a blood pressure regulator (Bhargava et al 1968). Jamun trees are available around parks, on roadsides, on avenues and are good windbreakers.…”

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confidence: 99%

Biochemical, microbiological and physiological changes in Jamun (Syzyium cumini L.) kept for long term storage under modified atmosphere packaging

Raj

Chadha²,

Kaur³

et al. 2011

J Food Sci Technol

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Jamun or Indian blackberry (Syzygium cumini L.) is a minor and highly perishable fruit enriched with flavonoids, essential oils, anthocyanins phenolic compounds and other antioxidants. The quantitative and qualitative losses in this seasonal fruit are tremendous and can be reduced by appropriate packaging and storage techniques which have not been applied hitherto. This study was undertaken to extend the shelf-life as well as to assess the biochemical, microbiological and physiological changes in jamun fruit under perforated and non-perforated modified atmosphere (MA) conditions. Fruits were stored under differential MA in macro-perforated (1 and 2 perforations, 0.3 mm dia. each) and non-perforated polypropylene (PP) film packages (Thickness: 35 μm, bag area: 0.036 m 2 ) at 5°C and 75% relative humidity (RH) for 23 days. Sachets containing white silica gel beads were placed inside all the packages to check water accumulation, if any. Different physiological, biochemical and microbiological characteristics which generally affect the postharvest life of the produce were monitored during the storage period. Results of the study suggested most of the subjectively and objectively determined qualitative parameters to be retained satisfactorily under macro-perforated packaging treatments. Further, the microbiological analysis, surmised that the fruits could be stored for long term using packages with 1 macro-perforation.Keywords Antioxidants . Jamun . Modified atmosphere packaging . Headspace . Pigments . Microbial load Indian blackberry (Syzygium cumini L.), commonly known as jamun is a minor and under-utilised tree-fruit of Indian subcontinent. The plant belongs to Myrtaceae family and grows naturally in clayey loamy soil in tropical as well as in sub-tropical zones of Indo-gangetic plains. These species are reported to be very rich in tannins, flavonoids, essential oils, anthocyanins and other phenolic constituents (Sharma et al. 2003;Reynertson et al. 2008). The purple coloured fruits are available abundantly during summer season for a short span of time, causing a seasonal glut. Jamun contains 19.7% carbohydrates, 0.7% proteins, 0.02% calcium, 0.1% fat, 0.01% phosphorous, 0.4% mineral matter, 0.1% iron and 0.9% fiber (Singh et al. 1967;Benherlal and Arumughan 2007). Besides, they contain anthocyanins which are the most important and widespread groups of colouring matters in plants. These intensely coloured water soluble pigments are responsible for nearly all colours in leaves, petals and fruits of higher plants. Jamun fruits and seeds are sweet, acrid and sour and they are used for treatment and control of diabetes, diarrhoea and ringworm. It is also reported to be a blood pressure regulator (Bhargava et al. 1968). Jamun trees are available around parks, on roadsides, on avenues and are good windbreakers. On account of its unorganised farming, consolidated information regarding its area and production in India is apparently not available. The fruits are highly perishable and are sold by the roadside vend...

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“…One oxygenated methine carbon resonated at d 71.8 (C-3), one oxygenated quaternary carbon at d 82.5 (C-17), and two trisubstituted double bond carbon atoms C-5 and C-6 at d 140. 6 19), and four methyl doublets at d 0.79 (J ¼ 6.5 Hz, Me-26), 0.81 (J ¼ 6.5 Hz, Me-29), 0.85 (J ¼ 6.9 Hz, Me-27), and 0.90 (J ¼ 6.9 Hz, Me-21). The characteristic H-6 of steroid 5,6-enes was noticed at d 5.33 as a doublet (J ¼ 5.5 Hz).…”

Section: Resultsmentioning

confidence: 99%

“…Fractionation of the hexane and ethyl acetate extracts from the fruits of S. siamense led to the isolation of a new naturally occurring stigmast-5-ene-3b,17a-diol (1), along with six known sterols, stigmast-5-ene-3b-yl formate (2), stigmast-5-ene-3b,7a-diol (3), stigmast-5-ene-7a-methoxy-3b-ol (4), stigmast-5-ene-3-one (5), 3b-sitostanol (6), and 3b-sitosterol (7) (Figure 1). The structures of the known compounds were elucidated by comparison of their physical and spectral data with the literature values [12][13][14][15].…”

Section: Introductionmentioning

confidence: 99%

New cytotoxic steroids from the fruits ofSyzygium siamense

Chumkaew¹,

Kato²,

Chantrapromma³

2010

Journal of Asian Natural Products Research

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A new sterol, stigmast-5-ene-3beta,17alpha-diol (1), together with six known compounds, stigmast-5-ene-3beta-yl formate (2), stigmast-5-ene-3beta,7alpha-diol (3), stigmast-5-ene-7alpha-methoxy-3beta-ol (4), stigmast-5-ene-3-one (5), 3beta-sitostanol (6), and 3beta-sitosterol (7), was isolated from the fruits of Syzygium siamense, of which compound 2 is reported for the first time from a natural source. Their structures were elucidated by spectroscopic methods. The isolated compounds (1-7) were evaluated for their cytotoxic activities against human oral epidermoid carcinoma cancer (KB), human breast cancer (BC), and human small cell lung cancer (NCI-H187) cell lines.

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Preliminary Pharmacology of Ellagic Acid From Juglans nigra (Black Walnut)

Cited by 23 publications

References 4 publications

Inhibition of the mutagenicity of bay-region diol epoxides of polycyclic aromatic hydrocarbons by naturally occurring plant phenols: Exceptional activity of ellagic acid

Inhibition of the mutagenicity of bay-region diol epoxides of polycyclic aromatic hydrocarbons by naturally occurring plant phenols: Exceptional activity of ellagic acid

Biochemical, microbiological and physiological changes in Jamun (Syzyium cumini L.) kept for long term storage under modified atmosphere packaging

New cytotoxic steroids from the fruits ofSyzygium siamense

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