Synthesis of rebaudioside-A by enzymatic transglycosylation of stevioside present in the leaves of Stevia rebaudiana Bertoni
•Enzyme mediated transglycosylation of stevioside to rebaudioside-A.•The glucosyl moiety transglycosylated stereospecifically to get 13-O-β-stevioside.•The rebaudioside-A content in the pre-treated stevia leaves increased from 4% to 66%.•95% pure rebaudioside-A was obtained by multiple column chroma...
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Veröffentlicht in: | Food chemistry 2016-06, Vol.200, p.154-158 |
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creator | Adari, Bhaskar Rao Alavala, Sateesh George, Sara A. Meshram, Harshadas M. Tiwari, Ashok K. Sarma, Akella V.S. |
description | •Enzyme mediated transglycosylation of stevioside to rebaudioside-A.•The glucosyl moiety transglycosylated stereospecifically to get 13-O-β-stevioside.•The rebaudioside-A content in the pre-treated stevia leaves increased from 4% to 66%.•95% pure rebaudioside-A was obtained by multiple column chromatography.
Rebaudioside-A is the second most abundant sweet diterpene glycoside (1–3%) present in the leaves of Stevia rebaudiana Bertoni, and is now being considered as a possible sucrose substitute due to its pleasant organoleptic properties and associated health benefits. In the present study, a novel in situ enzymatic transglycosylation of stevioside has been developed by pre-treating the stevia leaves with cellulase and adding soluble starch as the glucosyl donor. The results confirm that the transglycosylation of stevioside led to an enrichment in the rebaudioside-A content from 4% to 66%. This was further purified by multiple column chromatography to obtain 95% pure rebaudioside-A. The isolated rebaudioside-A showed concentration-dependent α-glucosidase inhibitory activity with IC50=35.01μg/ml. Thus the study highlights the biotransformation of stevioside present in stevia leaves to rebaudioside-A by a simple, inexpensive and eco-friendly process that has commercial potential. |
doi_str_mv | 10.1016/j.foodchem.2016.01.033 |
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Rebaudioside-A is the second most abundant sweet diterpene glycoside (1–3%) present in the leaves of Stevia rebaudiana Bertoni, and is now being considered as a possible sucrose substitute due to its pleasant organoleptic properties and associated health benefits. In the present study, a novel in situ enzymatic transglycosylation of stevioside has been developed by pre-treating the stevia leaves with cellulase and adding soluble starch as the glucosyl donor. The results confirm that the transglycosylation of stevioside led to an enrichment in the rebaudioside-A content from 4% to 66%. This was further purified by multiple column chromatography to obtain 95% pure rebaudioside-A. The isolated rebaudioside-A showed concentration-dependent α-glucosidase inhibitory activity with IC50=35.01μg/ml. Thus the study highlights the biotransformation of stevioside present in stevia leaves to rebaudioside-A by a simple, inexpensive and eco-friendly process that has commercial potential.</description><identifier>ISSN: 0308-8146</identifier><identifier>EISSN: 1873-7072</identifier><identifier>DOI: 10.1016/j.foodchem.2016.01.033</identifier><identifier>PMID: 26830573</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Cellulase ; Diterpenes, Kaurane - chemistry ; Food Additives - analysis ; Glucosides - chemistry ; Glucosyl donors ; Plant Leaves - chemistry ; Rebaudioside-A ; Stevia - chemistry ; Stevia leaves ; Sweetening Agents - chemistry ; Transglycosylation</subject><ispartof>Food chemistry, 2016-06, Vol.200, p.154-158</ispartof><rights>2016 Elsevier Ltd</rights><rights>Copyright © 2016 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c405t-8b8187f2a8d50441b64210d7ae930222e56cc5c3e5e606eb0d426999f4ed57723</citedby><cites>FETCH-LOGICAL-c405t-8b8187f2a8d50441b64210d7ae930222e56cc5c3e5e606eb0d426999f4ed57723</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.foodchem.2016.01.033$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26830573$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Adari, Bhaskar Rao</creatorcontrib><creatorcontrib>Alavala, Sateesh</creatorcontrib><creatorcontrib>George, Sara A.</creatorcontrib><creatorcontrib>Meshram, Harshadas M.</creatorcontrib><creatorcontrib>Tiwari, Ashok K.</creatorcontrib><creatorcontrib>Sarma, Akella V.S.</creatorcontrib><title>Synthesis of rebaudioside-A by enzymatic transglycosylation of stevioside present in the leaves of Stevia rebaudiana Bertoni</title><title>Food chemistry</title><addtitle>Food Chem</addtitle><description>•Enzyme mediated transglycosylation of stevioside to rebaudioside-A.•The glucosyl moiety transglycosylated stereospecifically to get 13-O-β-stevioside.•The rebaudioside-A content in the pre-treated stevia leaves increased from 4% to 66%.•95% pure rebaudioside-A was obtained by multiple column chromatography.
Rebaudioside-A is the second most abundant sweet diterpene glycoside (1–3%) present in the leaves of Stevia rebaudiana Bertoni, and is now being considered as a possible sucrose substitute due to its pleasant organoleptic properties and associated health benefits. In the present study, a novel in situ enzymatic transglycosylation of stevioside has been developed by pre-treating the stevia leaves with cellulase and adding soluble starch as the glucosyl donor. The results confirm that the transglycosylation of stevioside led to an enrichment in the rebaudioside-A content from 4% to 66%. This was further purified by multiple column chromatography to obtain 95% pure rebaudioside-A. The isolated rebaudioside-A showed concentration-dependent α-glucosidase inhibitory activity with IC50=35.01μg/ml. Thus the study highlights the biotransformation of stevioside present in stevia leaves to rebaudioside-A by a simple, inexpensive and eco-friendly process that has commercial potential.</description><subject>Cellulase</subject><subject>Diterpenes, Kaurane - chemistry</subject><subject>Food Additives - analysis</subject><subject>Glucosides - chemistry</subject><subject>Glucosyl donors</subject><subject>Plant Leaves - chemistry</subject><subject>Rebaudioside-A</subject><subject>Stevia - chemistry</subject><subject>Stevia leaves</subject><subject>Sweetening Agents - chemistry</subject><subject>Transglycosylation</subject><issn>0308-8146</issn><issn>1873-7072</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1v1DAQhi0EokvhL1Q-ckk6_oiT3ChV-ZAqcSicLceeUK8Se7GzK6Xix-Nlu1w5WWM97zuah5ArBjUDpq639Rijs48417zMNbAahHhBNqxrRdVCy1-SDQjoqo5JdUHe5LwFgMJ2r8kFV52AphUb8vthDcsjZp9pHGnCweydj9k7rG7osFIMT-tsFm_pkkzIP6fVxrxO5SeGYyIveDjxdJcwY1ioD7Q00gnNAf-2PhwZcy43wdCPmJYY_FvyajRTxnfP7yX58enu--2X6v7b56-3N_eVldAsVTd05aqRm841ICUblOQMXGuwF8A5x0ZZ21iBDSpQOICTXPV9P0p0TdtycUnen3p3Kf7aY1707LPFaTIB4z5r1ioupIS-Kag6oTbFnBOOepf8bNKqGeijeb3VZ_P6aF4D08V8CV4979gPM7p_sbPqAnw4AVguPXhMOluPwaLzCe2iXfT_2_EHUH-aAg</recordid><startdate>20160601</startdate><enddate>20160601</enddate><creator>Adari, Bhaskar Rao</creator><creator>Alavala, Sateesh</creator><creator>George, Sara A.</creator><creator>Meshram, Harshadas M.</creator><creator>Tiwari, Ashok K.</creator><creator>Sarma, Akella V.S.</creator><general>Elsevier Ltd</general><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>7X8</scope></search><sort><creationdate>20160601</creationdate><title>Synthesis of rebaudioside-A by enzymatic transglycosylation of stevioside present in the leaves of Stevia rebaudiana Bertoni</title><author>Adari, Bhaskar Rao ; Alavala, Sateesh ; George, Sara A. ; Meshram, Harshadas M. ; Tiwari, Ashok K. ; Sarma, Akella V.S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c405t-8b8187f2a8d50441b64210d7ae930222e56cc5c3e5e606eb0d426999f4ed57723</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Cellulase</topic><topic>Diterpenes, Kaurane - chemistry</topic><topic>Food Additives - analysis</topic><topic>Glucosides - chemistry</topic><topic>Glucosyl donors</topic><topic>Plant Leaves - chemistry</topic><topic>Rebaudioside-A</topic><topic>Stevia - chemistry</topic><topic>Stevia leaves</topic><topic>Sweetening Agents - chemistry</topic><topic>Transglycosylation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Adari, Bhaskar Rao</creatorcontrib><creatorcontrib>Alavala, Sateesh</creatorcontrib><creatorcontrib>George, Sara A.</creatorcontrib><creatorcontrib>Meshram, Harshadas M.</creatorcontrib><creatorcontrib>Tiwari, Ashok K.</creatorcontrib><creatorcontrib>Sarma, Akella V.S.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Adari, Bhaskar Rao</au><au>Alavala, Sateesh</au><au>George, Sara A.</au><au>Meshram, Harshadas M.</au><au>Tiwari, Ashok K.</au><au>Sarma, Akella V.S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of rebaudioside-A by enzymatic transglycosylation of stevioside present in the leaves of Stevia rebaudiana Bertoni</atitle><jtitle>Food chemistry</jtitle><addtitle>Food Chem</addtitle><date>2016-06-01</date><risdate>2016</risdate><volume>200</volume><spage>154</spage><epage>158</epage><pages>154-158</pages><issn>0308-8146</issn><eissn>1873-7072</eissn><abstract>•Enzyme mediated transglycosylation of stevioside to rebaudioside-A.•The glucosyl moiety transglycosylated stereospecifically to get 13-O-β-stevioside.•The rebaudioside-A content in the pre-treated stevia leaves increased from 4% to 66%.•95% pure rebaudioside-A was obtained by multiple column chromatography.
Rebaudioside-A is the second most abundant sweet diterpene glycoside (1–3%) present in the leaves of Stevia rebaudiana Bertoni, and is now being considered as a possible sucrose substitute due to its pleasant organoleptic properties and associated health benefits. In the present study, a novel in situ enzymatic transglycosylation of stevioside has been developed by pre-treating the stevia leaves with cellulase and adding soluble starch as the glucosyl donor. The results confirm that the transglycosylation of stevioside led to an enrichment in the rebaudioside-A content from 4% to 66%. This was further purified by multiple column chromatography to obtain 95% pure rebaudioside-A. The isolated rebaudioside-A showed concentration-dependent α-glucosidase inhibitory activity with IC50=35.01μg/ml. Thus the study highlights the biotransformation of stevioside present in stevia leaves to rebaudioside-A by a simple, inexpensive and eco-friendly process that has commercial potential.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>26830573</pmid><doi>10.1016/j.foodchem.2016.01.033</doi><tpages>5</tpages></addata></record> |
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subjects | Cellulase Diterpenes, Kaurane - chemistry Food Additives - analysis Glucosides - chemistry Glucosyl donors Plant Leaves - chemistry Rebaudioside-A Stevia - chemistry Stevia leaves Sweetening Agents - chemistry Transglycosylation |
title | Synthesis of rebaudioside-A by enzymatic transglycosylation of stevioside present in the leaves of Stevia rebaudiana Bertoni |
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