A γ-Glutamyl Peptide Isolated from Onion (Allium cepa L.) by Bioassay-Guided Fractionation Inhibits Resorption Activity of Osteoclasts
One gram of onion added to the food of rats inhibits significantly (p < 0.05) bone resorption as assessed by the urinary excretion of tritium released from bone of 9-week-old rats prelabeled with tritiated tetracycline from weeks 1 to 6. To isolate and identify the bone resorption inhibiting comp...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2005-05, Vol.53 (9), p.3408-3414 |
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| creator | Wetli, Herbert A Brenneisen, Rudolf Tschudi, Ingrid Langos, Manuela Bigler, Peter Sprang, Thomas Schürch, Stefan Mühlbauer, Roman C |
| description | One gram of onion added to the food of rats inhibits significantly (p < 0.05) bone resorption as assessed by the urinary excretion of tritium released from bone of 9-week-old rats prelabeled with tritiated tetracycline from weeks 1 to 6. To isolate and identify the bone resorption inhibiting compound from onion, onion powder was extracted and the extract fractionated by column chromatography and medium-pressure liquid chromatography. A single active peak was finally obtained by semipreparative high-performance liquid chromatography. The biological activity of the various fractions was tested in vitro on the activity of osteoclasts to form resorption pits on a mineralized substrate. Medium, containing the various fractions or the pure compound, was added to osteoclasts of new-born rats settled on ivory slices. After 24 h of incubation, the tartrate-resistant acid phosphatase positive multinucleated cells, that is, osteoclasts, were counted. Subsequently, the number of resorption pits was determined. Activity was calculated as the ratio of resorption pits/osteoclasts and was compared to a negative control, that is, medium containing 10% fetal bovine serum only and to calcitonin (10-12 M) as a positive control. Finally, a single peak inhibited osteoclast activity significantly (p < 0.05). The structure of this compound was elucidated with high-performance liquid chromatography−electrospray ionization−mass spectrometry, time-of-flight electrospray ionization mass spectrometry, and nuclear magnetic resonance spectroscopy. The single peak was identified as γ-l-glutamyl-trans-S-1-propenyl-l-cysteine sulfoxide (GPCS). It has a molecular mass of 306 Da and inhibits dose-dependently the resorption activity of osteoclasts, the minimal effective dose being ∼2 mM. As no other peak displayed inhibitory activity, it likely is responsible for the effect of onion on bone resorption. Keywords: Allium cepa L.; Alliaceae; glutamyl peptide; bone resorption; osteoporosis; nutrition |
| doi_str_mv | 10.1021/jf040457i |
| format | Article |
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To isolate and identify the bone resorption inhibiting compound from onion, onion powder was extracted and the extract fractionated by column chromatography and medium-pressure liquid chromatography. A single active peak was finally obtained by semipreparative high-performance liquid chromatography. The biological activity of the various fractions was tested in vitro on the activity of osteoclasts to form resorption pits on a mineralized substrate. Medium, containing the various fractions or the pure compound, was added to osteoclasts of new-born rats settled on ivory slices. After 24 h of incubation, the tartrate-resistant acid phosphatase positive multinucleated cells, that is, osteoclasts, were counted. Subsequently, the number of resorption pits was determined. Activity was calculated as the ratio of resorption pits/osteoclasts and was compared to a negative control, that is, medium containing 10% fetal bovine serum only and to calcitonin (10-12 M) as a positive control. Finally, a single peak inhibited osteoclast activity significantly (p < 0.05). The structure of this compound was elucidated with high-performance liquid chromatography−electrospray ionization−mass spectrometry, time-of-flight electrospray ionization mass spectrometry, and nuclear magnetic resonance spectroscopy. The single peak was identified as γ-l-glutamyl-trans-S-1-propenyl-l-cysteine sulfoxide (GPCS). It has a molecular mass of 306 Da and inhibits dose-dependently the resorption activity of osteoclasts, the minimal effective dose being ∼2 mM. As no other peak displayed inhibitory activity, it likely is responsible for the effect of onion on bone resorption. Keywords: Allium cepa L.; Alliaceae; glutamyl peptide; bone resorption; osteoporosis; nutrition</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf040457i</identifier><identifier>PMID: 15853380</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Animals ; bioassays ; Biological and medical sciences ; Biological Assay ; bone resorption ; Bone Resorption - prevention & control ; Chemical Fractionation ; Chromatography, High Pressure Liquid ; Dipeptides - chemistry ; Dipeptides - isolation & purification ; Dipeptides - pharmacology ; Feeding. Feeding behavior ; Food industries ; fractionation ; Fruit and vegetable industries ; Fundamental and applied biological sciences. Psychology ; gamma-glutamyl peptide ; gamma-glutamyl-trans-S-1-propenyl-cysteine sulfoxide ; Magnetic Resonance Spectroscopy ; metabolic inhibitors ; onions ; Onions - chemistry ; organic sulfur compounds ; osteoclasts ; Osteoclasts - drug effects ; peptides ; plant extracts ; Rats ; Spectrometry, Mass, Electrospray Ionization ; Sulfoxides ; Vertebrates: anatomy and physiology, studies on body, several organs or systems</subject><ispartof>Journal of agricultural and food chemistry, 2005-05, Vol.53 (9), p.3408-3414</ispartof><rights>Copyright © 2005 American Chemical Society</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a436t-e7b82adcf620d1ef68f9911407302536c46a1dc118098a761df3833dcc56a9803</citedby><cites>FETCH-LOGICAL-a436t-e7b82adcf620d1ef68f9911407302536c46a1dc118098a761df3833dcc56a9803</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jf040457i$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf040457i$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16732664$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15853380$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wetli, Herbert A</creatorcontrib><creatorcontrib>Brenneisen, Rudolf</creatorcontrib><creatorcontrib>Tschudi, Ingrid</creatorcontrib><creatorcontrib>Langos, Manuela</creatorcontrib><creatorcontrib>Bigler, Peter</creatorcontrib><creatorcontrib>Sprang, Thomas</creatorcontrib><creatorcontrib>Schürch, Stefan</creatorcontrib><creatorcontrib>Mühlbauer, Roman C</creatorcontrib><title>A γ-Glutamyl Peptide Isolated from Onion (Allium cepa L.) by Bioassay-Guided Fractionation Inhibits Resorption Activity of Osteoclasts</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>One gram of onion added to the food of rats inhibits significantly (p < 0.05) bone resorption as assessed by the urinary excretion of tritium released from bone of 9-week-old rats prelabeled with tritiated tetracycline from weeks 1 to 6. To isolate and identify the bone resorption inhibiting compound from onion, onion powder was extracted and the extract fractionated by column chromatography and medium-pressure liquid chromatography. A single active peak was finally obtained by semipreparative high-performance liquid chromatography. The biological activity of the various fractions was tested in vitro on the activity of osteoclasts to form resorption pits on a mineralized substrate. Medium, containing the various fractions or the pure compound, was added to osteoclasts of new-born rats settled on ivory slices. After 24 h of incubation, the tartrate-resistant acid phosphatase positive multinucleated cells, that is, osteoclasts, were counted. Subsequently, the number of resorption pits was determined. Activity was calculated as the ratio of resorption pits/osteoclasts and was compared to a negative control, that is, medium containing 10% fetal bovine serum only and to calcitonin (10-12 M) as a positive control. Finally, a single peak inhibited osteoclast activity significantly (p < 0.05). The structure of this compound was elucidated with high-performance liquid chromatography−electrospray ionization−mass spectrometry, time-of-flight electrospray ionization mass spectrometry, and nuclear magnetic resonance spectroscopy. The single peak was identified as γ-l-glutamyl-trans-S-1-propenyl-l-cysteine sulfoxide (GPCS). It has a molecular mass of 306 Da and inhibits dose-dependently the resorption activity of osteoclasts, the minimal effective dose being ∼2 mM. As no other peak displayed inhibitory activity, it likely is responsible for the effect of onion on bone resorption. Keywords: Allium cepa L.; Alliaceae; glutamyl peptide; bone resorption; osteoporosis; nutrition</description><subject>Animals</subject><subject>bioassays</subject><subject>Biological and medical sciences</subject><subject>Biological Assay</subject><subject>bone resorption</subject><subject>Bone Resorption - prevention & control</subject><subject>Chemical Fractionation</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Dipeptides - chemistry</subject><subject>Dipeptides - isolation & purification</subject><subject>Dipeptides - pharmacology</subject><subject>Feeding. Feeding behavior</subject><subject>Food industries</subject><subject>fractionation</subject><subject>Fruit and vegetable industries</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>gamma-glutamyl peptide</subject><subject>gamma-glutamyl-trans-S-1-propenyl-cysteine sulfoxide</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>metabolic inhibitors</subject><subject>onions</subject><subject>Onions - chemistry</subject><subject>organic sulfur compounds</subject><subject>osteoclasts</subject><subject>Osteoclasts - drug effects</subject><subject>peptides</subject><subject>plant extracts</subject><subject>Rats</subject><subject>Spectrometry, Mass, Electrospray Ionization</subject><subject>Sulfoxides</subject><subject>Vertebrates: anatomy and physiology, studies on body, several organs or systems</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0d1u0zAUB_AIgVgZXPAC4BsQu8iw4_gjl6VipVCpg23s0jp1bHCXxMFOEH0CHoj34JnwaLXeIHETSzk_H_v4n2VPCT4luCCvNxaXuGTC3csmhBU4Z4TI-9kEp2IuGSdH2aMYNxhjyQR-mB0RJhmlEk-yn1P0-1c-b8YB2m2Dzk0_uNqgRfQNDKZGNvgWrTrnO_Rq2jRubJE2PaDl6Qlab9Eb5yFG2ObzMW2r0VkAPSQMtx-06L66tRsi-mSiD_3ff9NU_-6GLfIWreJgvG4gDvFx9sBCE82T_XqcXZ29vZy9y5er-WI2XeZQUj7kRqxlAbW2vMA1MZZLW1WElFhQXDDKdcmB1DqNjysJgpPaUklprTXjUElMj7OXu7598N9GEwfVuqhN00Bn_BgVF0KWspL_hUTQkmNWJXiygzr4GIOxqg-uhbBVBKvbeNRdPMk-2zcd162pD3KfRwIv9gCihsYG6LSLB8cFLTgvk8t3zqUn_HFXh3CTJqCCqcvzC_X5_ez6A_8o1HXyz3feglfwJaSeVxcFJhSTdLeK8MPJoKPa-DF0KYZ_jPAHQZy8RA</recordid><startdate>20050504</startdate><enddate>20050504</enddate><creator>Wetli, Herbert A</creator><creator>Brenneisen, Rudolf</creator><creator>Tschudi, Ingrid</creator><creator>Langos, Manuela</creator><creator>Bigler, Peter</creator><creator>Sprang, Thomas</creator><creator>Schürch, Stefan</creator><creator>Mühlbauer, Roman C</creator><general>American Chemical Society</general><scope>FBQ</scope><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QP</scope><scope>7X8</scope></search><sort><creationdate>20050504</creationdate><title>A γ-Glutamyl Peptide Isolated from Onion (Allium cepa L.) by Bioassay-Guided Fractionation Inhibits Resorption Activity of Osteoclasts</title><author>Wetli, Herbert A ; Brenneisen, Rudolf ; Tschudi, Ingrid ; Langos, Manuela ; Bigler, Peter ; Sprang, Thomas ; Schürch, Stefan ; Mühlbauer, Roman C</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a436t-e7b82adcf620d1ef68f9911407302536c46a1dc118098a761df3833dcc56a9803</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Animals</topic><topic>bioassays</topic><topic>Biological and medical sciences</topic><topic>Biological Assay</topic><topic>bone resorption</topic><topic>Bone Resorption - prevention & control</topic><topic>Chemical Fractionation</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Dipeptides - chemistry</topic><topic>Dipeptides - isolation & purification</topic><topic>Dipeptides - pharmacology</topic><topic>Feeding. Feeding behavior</topic><topic>Food industries</topic><topic>fractionation</topic><topic>Fruit and vegetable industries</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>gamma-glutamyl peptide</topic><topic>gamma-glutamyl-trans-S-1-propenyl-cysteine sulfoxide</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>metabolic inhibitors</topic><topic>onions</topic><topic>Onions - chemistry</topic><topic>organic sulfur compounds</topic><topic>osteoclasts</topic><topic>Osteoclasts - drug effects</topic><topic>peptides</topic><topic>plant extracts</topic><topic>Rats</topic><topic>Spectrometry, Mass, Electrospray Ionization</topic><topic>Sulfoxides</topic><topic>Vertebrates: anatomy and physiology, studies on body, several organs or systems</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wetli, Herbert A</creatorcontrib><creatorcontrib>Brenneisen, Rudolf</creatorcontrib><creatorcontrib>Tschudi, Ingrid</creatorcontrib><creatorcontrib>Langos, Manuela</creatorcontrib><creatorcontrib>Bigler, Peter</creatorcontrib><creatorcontrib>Sprang, Thomas</creatorcontrib><creatorcontrib>Schürch, Stefan</creatorcontrib><creatorcontrib>Mühlbauer, Roman C</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Calcium & Calcified Tissue Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wetli, Herbert A</au><au>Brenneisen, Rudolf</au><au>Tschudi, Ingrid</au><au>Langos, Manuela</au><au>Bigler, Peter</au><au>Sprang, Thomas</au><au>Schürch, Stefan</au><au>Mühlbauer, Roman C</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A γ-Glutamyl Peptide Isolated from Onion (Allium cepa L.) by Bioassay-Guided Fractionation Inhibits Resorption Activity of Osteoclasts</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2005-05-04</date><risdate>2005</risdate><volume>53</volume><issue>9</issue><spage>3408</spage><epage>3414</epage><pages>3408-3414</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>One gram of onion added to the food of rats inhibits significantly (p < 0.05) bone resorption as assessed by the urinary excretion of tritium released from bone of 9-week-old rats prelabeled with tritiated tetracycline from weeks 1 to 6. To isolate and identify the bone resorption inhibiting compound from onion, onion powder was extracted and the extract fractionated by column chromatography and medium-pressure liquid chromatography. A single active peak was finally obtained by semipreparative high-performance liquid chromatography. The biological activity of the various fractions was tested in vitro on the activity of osteoclasts to form resorption pits on a mineralized substrate. Medium, containing the various fractions or the pure compound, was added to osteoclasts of new-born rats settled on ivory slices. After 24 h of incubation, the tartrate-resistant acid phosphatase positive multinucleated cells, that is, osteoclasts, were counted. Subsequently, the number of resorption pits was determined. Activity was calculated as the ratio of resorption pits/osteoclasts and was compared to a negative control, that is, medium containing 10% fetal bovine serum only and to calcitonin (10-12 M) as a positive control. Finally, a single peak inhibited osteoclast activity significantly (p < 0.05). The structure of this compound was elucidated with high-performance liquid chromatography−electrospray ionization−mass spectrometry, time-of-flight electrospray ionization mass spectrometry, and nuclear magnetic resonance spectroscopy. The single peak was identified as γ-l-glutamyl-trans-S-1-propenyl-l-cysteine sulfoxide (GPCS). It has a molecular mass of 306 Da and inhibits dose-dependently the resorption activity of osteoclasts, the minimal effective dose being ∼2 mM. As no other peak displayed inhibitory activity, it likely is responsible for the effect of onion on bone resorption. Keywords: Allium cepa L.; Alliaceae; glutamyl peptide; bone resorption; osteoporosis; nutrition</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15853380</pmid><doi>10.1021/jf040457i</doi><tpages>7</tpages></addata></record> |
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| subjects | Animals bioassays Biological and medical sciences Biological Assay bone resorption Bone Resorption - prevention & control Chemical Fractionation Chromatography, High Pressure Liquid Dipeptides - chemistry Dipeptides - isolation & purification Dipeptides - pharmacology Feeding. Feeding behavior Food industries fractionation Fruit and vegetable industries Fundamental and applied biological sciences. Psychology gamma-glutamyl peptide gamma-glutamyl-trans-S-1-propenyl-cysteine sulfoxide Magnetic Resonance Spectroscopy metabolic inhibitors onions Onions - chemistry organic sulfur compounds osteoclasts Osteoclasts - drug effects peptides plant extracts Rats Spectrometry, Mass, Electrospray Ionization Sulfoxides Vertebrates: anatomy and physiology, studies on body, several organs or systems |
| title | A γ-Glutamyl Peptide Isolated from Onion (Allium cepa L.) by Bioassay-Guided Fractionation Inhibits Resorption Activity of Osteoclasts |
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