• Title/Summary/Keyword: cyanogenic glucoside

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Amygdalin Regulates Apoptosis and Adhesion in Hs578T Triple-Negative Breast Cancer Cells

  • Lee, Hye Min;Moon, Aree
    • Biomolecules & Therapeutics
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    • v.24 no.1
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    • pp.62-66
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    • 2016
  • Amygdalin, D-mandelonitrile-${\beta}$-D-glucoside-6-${\beta}$-glucoside, belongs to aromatic cyanogenic glycoside group derived from rosaceous plant seed. Mounting evidence has supported the anti-cancer effects of amygdalin. However, whether amygdalin indeed acts as an anti-tumor agent against breast cancer cells is not clear. The present study aimed to investigate the effect of amygdalin on the proliferation of human breast cancer cells. Here, we show that amygdalin exerted cytotoxic activities on estrogen receptors (ER)-positive MCF7 cells, and MDA-MB-231 and Hs578T triple-negative breast cancer (TNBC) cells. Amygdalin induced apoptosis of Hs578T TNBC cells. Amygdalin downregulated B-cell lymphoma 2 (Bcl-2), upregulated Bcl-2-associated X protein (Bax), activated of caspase-3 and cleaved poly ADP-ribose polymerase (PARP). Amygdalin activated a pro-apoptotic signaling molecule p38 mitogen-activated protein kinases (p38 MAPK) in Hs578T cells. Treatment of amygdalin significantly inhibited the adhesion of Hs578T cells, in which integrin ${\alpha}5$ may be involved. Taken together, this study demonstrates that amygdalin induces apoptosis and inhibits adhesion of breast cancer cells. The results suggest a potential application of amygdalin as a chemopreventive agent to prevent or alleviate progression of breast cancer, especially TNBC.

Contents of Cyanogenic Glucosides in Processed Foods and during Ripening of Ume According to Varieties and Picking Date (매실품종과 수확시기별 및 매실가공식품의 시안화합물의 변화)

  • 김용두;강성구;현규환
    • Food Science and Preservation
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    • v.9 no.1
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    • pp.42-45
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    • 2002
  • Variations of cyanogenic glucoside was investigated on varieties, picking date, each part and processed flood of Ume. First, variation of amygdalin contents was determined by HPLC during ripening. As a result in case of peels, Oshuku showed most highest content(20.2 mg%) in all varieties. In case of seeds, Native species showed most highest content(562 mg%), and seeds contented more than peels. And then, variation of prunasin contents was determined by HPLC. As a results in case of peels, native species contented most lowest prunasin in all varieties, and its contents slightly decreased with increased storage periods. Other hand, in case of seeds, native species contented most highest prunasin(177 mg%). Contents of amygdalin and prunasin of extracts was determined by HPLC during six month ripening. As a result, in case of freezing storages contents of those not changed hardly during ripening. But, in case of native storage, contents of amygdalin was decreased and prunasin was increased with increased aging periods. Profile of Ume tea was similar to extracts of it.

Analysis and Decrease of Cyanogenic Glucosides in Flaxseed (아마인에 함유된 시안배당체의 분석과 저감화)

  • Park, Eun-Ryong;Hong, Jin-Hwan;Lee, Dong-Ha;Han, Sang-Bae;Lee, Kang-Bong;Park, Jae-Seok;Chung, Hyung-Wook;Hong, Kyung-Hyun;Kim, Myung-Chul
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.34 no.6
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    • pp.875-879
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    • 2005
  • Linustatin and neolinustatin in flaxseed are called cyanogenic glucosides which produce acetone, hydrogen cyanide (HCN) and sugar when hydrolyzed. The HCN is the chemical whose toxin is being issued in food safety. Linustatin and neolinustatin were found in flaxseed by 206.5 and 174.2 mg/100 g, respectively using a RI-HPLC and LC/MSn analysis of $80\%$ methanol extraction. Also, HCN (137.38 mg/kg) was found in flaxseed distillate by autohydrolysis and IC analysis. More than 85$\%$ of linustatin, neolinustatin and HCN were removed when flaxseed was heated for more than 2 hours in $200^{\circ}C$. Especially, HCN was decreased to $98\%$ by heating only 30 min in $200^{\circ}C$.

Screening the level of cyanogenic glucosides (dhurrin) in sorghum accessions using HPLC analysis

  • Choi, Sang Chul;Chung, Yong Suk;Lee, Yun Gyeong;Park, Yun Ji;Kim, Changsoo
    • Proceedings of the Korean Society of Crop Science Conference
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    • 2017.06a
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    • pp.104-104
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    • 2017
  • Sorghum (Sorghum bicolor (L.) Moench.) is one of the most important crops for human and animal nutrition. Nonetheless, sorghum has a cyanogenic glucoside compound which can be degraded into hydrogen cyanide, toxic to humans and animals even with tiny amount. In consequence, breeding materials with a low cyanide level has been a top priority in sorghum breeding programs. To fulfill our long-term goal, we are screening sorghum accessions with low cyanide level, which would be an important breeding material for food safety. We collected seeds of various sorghum accessions and analyzed relevant metabolites to find useful breeding materials of sorghum accessions containing low cyanide. Fourteen wild relatives were obtained from the University of Georgia in US, a reference accession BTx623, and three local varieties from National Agrobiodiversity Center of Rural Development Administration in Korea, and one wild species from the Wild Plant Resources Seed Bank of Korea University in Korea. Sorghum plants were grown in plastic greenhouse under natural conditions. After growing, leaf samples were harvested at different developmental stages: seedling phase, vegetative phase (right before flowering), and reproductive phase (ripening). Using collected samples, quantification analysis were performed by an HPLC system for three metabolites (dhurrin, 4-hydroxybenzaldehyde, and 4-hydroxyphenylacetic acid) in sorghum plants. Prior to metabolome analysis, specific experimental condition for HPLC system was set to be able to separate three metabolites simultaneously. Under this condition, these metabolites were quantified in each accession by HPLC system. We observed that the metabolite contents were changed differently by developmental stages and accessions. We clustered these results into five groups as patterns of their contents by developmental stages. Most of accessions showed that 4-hydroxybenzaldehyde content was very high at seedling stage and decreased rapidly at vegetative phase. Interestingly, the patterns of dhurrin content were very different among clusters. However, 4-hydroxyphenylacetic acid content was maintained at low levels by developmental stages in most accessions. The results would demonstrate how dhurrin and alternative degradation pathways are differentiated in each accession.

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Bioactive Constituents from the n-Butanolic Fraction of Aruncus dioicus var. kamtschaticus

  • Vo, Quoc Hung;Nguyen, Phi Hung;Zhao, Bing Tian;Thi, Yen Nguyen;Nguyen, Duc Hung;Kim, Won Il;Seo, U Min;Min, Byung Sun;Woo, Mi Hee
    • Natural Product Sciences
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    • v.20 no.4
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    • pp.274-280
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    • 2014
  • Six compounds were isolated from the n-BuOH fraction of the aerial parts of Aruncus dioicus var. kamtschaticus including: sambunigrin (1), prunasin (2), aruncide A (3), aruncide C (4), 1-O-caffeoyl-${\beta}$-D-glucopyranose (5), and caffeic acid (6). Their structures were confirmed by comparing the spectral data with those reported in the literature. The isolated compounds (1 - 6) were then examined for their cytotoxic effects towards MCF-7, HL-60, and HeLa cancer cell lines, as well as their DPPH radical scavenging activity. The results indicated that compound 4 possessed the strongest inhibitory effect toward HeLa cell line with $IC_{50}$ value of $5.38{\pm}0.92{\mu}M$. Compound 3 possessed selective cytotoxic activity on HL-60 cells with $IC_{50}$ value of $6.27{\pm}0.17{\mu}M$, compound 5 was found as the best in inhibiting proliferation with $IC_{50}$ value of $2.25{\pm}0.09{\mu}M$, and the other compounds showed significant inhibition with $IC_{50}$ values ranging from 6.10 to $11.27{\mu}M$. Compound 5 also displayed the strongest cytotoxic effect toward MCF-7 cell line ($IC_{50}$ $4.32{\pm}0.15{\mu}M$). Both 5 and 6 demonstrated strong radical scavenging activity ($IC_{50}$ $6.87{\pm}0.03$ and $4.33{\pm}0.22{\mu}M$, respectively). Compounds 1 and 5 were isolated for the first time from this plant.