Iteamine, the first alkaloid isolated from Itea virginica L. inflorescence
Iteamine, o-aminobenzyl β-d-glucopyranoside, is the first alkaloid isolated from Itea, the only plant source of the rare sugar d-psicose in development as a zero calorie food. •The discovery of iteamine, the first alkaloid isolated from Itea virginica.•Confirmation of the structure of iteamine by sy...
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| Veröffentlicht in: | Phytochemistry (Oxford) 2014-04, Vol.100, p.126-131 |
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| container_title | Phytochemistry (Oxford) |
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| creator | Ayers, Benjamin J. Hollinshead, Jacqueline Saville, Alexander W. Nakagawa, Shinpei Adachi, Isao Kato, Atsushi Izumori, Ken Bartholomew, Barbara Fleet, George W.J. Nash, Robert J. |
| description | Iteamine, o-aminobenzyl β-d-glucopyranoside, is the first alkaloid isolated from Itea, the only plant source of the rare sugar d-psicose in development as a zero calorie food.
•The discovery of iteamine, the first alkaloid isolated from Itea virginica.•Confirmation of the structure of iteamine by synthesis, and the synthesis of the galacto-epimer.•The galacto-epimer of iteamine showed weak but interesting inhibition of alpha-GalNAcase.
Iteamine, o-aminobenzyl β-d-glucopyranoside, is the first alkaloid to be isolated from Itea virginica. Itea is the sole plant source of d-psicose, a rare sugar likely to be a major dietary supplement. The structure of iteamine was established by NMR and confirmed by total synthesis. Iteamine and its galacto-analog (which was not found in Itea plants) showed no strong inhibition of any of the 15 glycosidases tested; unnatural galacto-iteamine was a weak inhibitor of chicken liver α-N-acetylgalactosaminidase. |
| doi_str_mv | 10.1016/j.phytochem.2014.01.012 |
| format | Article |
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•The discovery of iteamine, the first alkaloid isolated from Itea virginica.•Confirmation of the structure of iteamine by synthesis, and the synthesis of the galacto-epimer.•The galacto-epimer of iteamine showed weak but interesting inhibition of alpha-GalNAcase.
Iteamine, o-aminobenzyl β-d-glucopyranoside, is the first alkaloid to be isolated from Itea virginica. Itea is the sole plant source of d-psicose, a rare sugar likely to be a major dietary supplement. The structure of iteamine was established by NMR and confirmed by total synthesis. Iteamine and its galacto-analog (which was not found in Itea plants) showed no strong inhibition of any of the 15 glycosidases tested; unnatural galacto-iteamine was a weak inhibitor of chicken liver α-N-acetylgalactosaminidase.</description><identifier>ISSN: 0031-9422</identifier><identifier>EISSN: 1873-3700</identifier><identifier>DOI: 10.1016/j.phytochem.2014.01.012</identifier><identifier>PMID: 24534106</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Alkaloids - chemistry ; Alkaloids - isolation & purification ; Alkaloids - pharmacology ; alpha-N-Acetylgalactosaminidase - antagonists & inhibitors ; Animals ; d-Psicose ; Enzyme Inhibitors - chemistry ; Enzyme Inhibitors - isolation & purification ; Enzyme Inhibitors - pharmacology ; Glucosides ; Grossulariaceae ; Inflorescence - chemistry ; Itea virginica ; Iteamine ; Tracheophyta - chemistry ; α-N-acetylgalactosaminidase</subject><ispartof>Phytochemistry (Oxford), 2014-04, Vol.100, p.126-131</ispartof><rights>2014 Elsevier Ltd</rights><rights>Copyright © 2014 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c437t-73fcb4df5d5a946e74e302f7dcdc4e4e53dc06dea1ed0d6bad018fe34dee7b2b3</citedby><cites>FETCH-LOGICAL-c437t-73fcb4df5d5a946e74e302f7dcdc4e4e53dc06dea1ed0d6bad018fe34dee7b2b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.phytochem.2014.01.012$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>315,781,785,3551,27929,27930,46000</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24534106$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ayers, Benjamin J.</creatorcontrib><creatorcontrib>Hollinshead, Jacqueline</creatorcontrib><creatorcontrib>Saville, Alexander W.</creatorcontrib><creatorcontrib>Nakagawa, Shinpei</creatorcontrib><creatorcontrib>Adachi, Isao</creatorcontrib><creatorcontrib>Kato, Atsushi</creatorcontrib><creatorcontrib>Izumori, Ken</creatorcontrib><creatorcontrib>Bartholomew, Barbara</creatorcontrib><creatorcontrib>Fleet, George W.J.</creatorcontrib><creatorcontrib>Nash, Robert J.</creatorcontrib><title>Iteamine, the first alkaloid isolated from Itea virginica L. inflorescence</title><title>Phytochemistry (Oxford)</title><addtitle>Phytochemistry</addtitle><description>Iteamine, o-aminobenzyl β-d-glucopyranoside, is the first alkaloid isolated from Itea, the only plant source of the rare sugar d-psicose in development as a zero calorie food.
•The discovery of iteamine, the first alkaloid isolated from Itea virginica.•Confirmation of the structure of iteamine by synthesis, and the synthesis of the galacto-epimer.•The galacto-epimer of iteamine showed weak but interesting inhibition of alpha-GalNAcase.
Iteamine, o-aminobenzyl β-d-glucopyranoside, is the first alkaloid to be isolated from Itea virginica. Itea is the sole plant source of d-psicose, a rare sugar likely to be a major dietary supplement. The structure of iteamine was established by NMR and confirmed by total synthesis. Iteamine and its galacto-analog (which was not found in Itea plants) showed no strong inhibition of any of the 15 glycosidases tested; unnatural galacto-iteamine was a weak inhibitor of chicken liver α-N-acetylgalactosaminidase.</description><subject>Alkaloids - chemistry</subject><subject>Alkaloids - isolation & purification</subject><subject>Alkaloids - pharmacology</subject><subject>alpha-N-Acetylgalactosaminidase - antagonists & inhibitors</subject><subject>Animals</subject><subject>d-Psicose</subject><subject>Enzyme Inhibitors - chemistry</subject><subject>Enzyme Inhibitors - isolation & purification</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Glucosides</subject><subject>Grossulariaceae</subject><subject>Inflorescence - chemistry</subject><subject>Itea virginica</subject><subject>Iteamine</subject><subject>Tracheophyta - chemistry</subject><subject>α-N-acetylgalactosaminidase</subject><issn>0031-9422</issn><issn>1873-3700</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkMtOwzAQRS0EoqXwC-AlCxLGsZO0y6riUVSJDawtxx5TlyQudlqpf0-qlm6RRprNufM4hNwxSBmw4nGVrpe7zuslNmkGTKTA-srOyJCNS57wEuCcDAE4SyYiywbkKsYVAOR5UVySQSZyLhgUQ_I271A1rsUH2i2RWhdiR1X9rWrvDHXR16pDQ23wDd2jdOvCl2udVnSRUtfa2geMGluN1-TCqjrizbGPyOfz08fsNVm8v8xn00WiBS-7pORWV8LY3ORqIgosBXLIbGm00QIF5txoKAwqhgZMUSkDbGyRC4NYVlnFR-T-MHcd_M8GYycb119Q16pFv4mS5SBYzrgQPVoeUB18jAGtXAfXqLCTDORepFzJk0i5FymB9ZX1ydvjkk3VoDnl_sz1wPQAYP_q1mGQUbu9BuMC6k4a7_5d8gsN04oL</recordid><startdate>20140401</startdate><enddate>20140401</enddate><creator>Ayers, Benjamin J.</creator><creator>Hollinshead, Jacqueline</creator><creator>Saville, Alexander W.</creator><creator>Nakagawa, Shinpei</creator><creator>Adachi, Isao</creator><creator>Kato, Atsushi</creator><creator>Izumori, Ken</creator><creator>Bartholomew, Barbara</creator><creator>Fleet, George W.J.</creator><creator>Nash, Robert J.</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>20140401</creationdate><title>Iteamine, the first alkaloid isolated from Itea virginica L. inflorescence</title><author>Ayers, Benjamin J. ; Hollinshead, Jacqueline ; Saville, Alexander W. ; Nakagawa, Shinpei ; Adachi, Isao ; Kato, Atsushi ; Izumori, Ken ; Bartholomew, Barbara ; Fleet, George W.J. ; Nash, Robert J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c437t-73fcb4df5d5a946e74e302f7dcdc4e4e53dc06dea1ed0d6bad018fe34dee7b2b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Alkaloids - chemistry</topic><topic>Alkaloids - isolation & purification</topic><topic>Alkaloids - pharmacology</topic><topic>alpha-N-Acetylgalactosaminidase - antagonists & inhibitors</topic><topic>Animals</topic><topic>d-Psicose</topic><topic>Enzyme Inhibitors - chemistry</topic><topic>Enzyme Inhibitors - isolation & purification</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>Glucosides</topic><topic>Grossulariaceae</topic><topic>Inflorescence - chemistry</topic><topic>Itea virginica</topic><topic>Iteamine</topic><topic>Tracheophyta - chemistry</topic><topic>α-N-acetylgalactosaminidase</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ayers, Benjamin J.</creatorcontrib><creatorcontrib>Hollinshead, Jacqueline</creatorcontrib><creatorcontrib>Saville, Alexander W.</creatorcontrib><creatorcontrib>Nakagawa, Shinpei</creatorcontrib><creatorcontrib>Adachi, Isao</creatorcontrib><creatorcontrib>Kato, Atsushi</creatorcontrib><creatorcontrib>Izumori, Ken</creatorcontrib><creatorcontrib>Bartholomew, Barbara</creatorcontrib><creatorcontrib>Fleet, George W.J.</creatorcontrib><creatorcontrib>Nash, Robert J.</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>Phytochemistry (Oxford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ayers, Benjamin J.</au><au>Hollinshead, Jacqueline</au><au>Saville, Alexander W.</au><au>Nakagawa, Shinpei</au><au>Adachi, Isao</au><au>Kato, Atsushi</au><au>Izumori, Ken</au><au>Bartholomew, Barbara</au><au>Fleet, George W.J.</au><au>Nash, Robert J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Iteamine, the first alkaloid isolated from Itea virginica L. inflorescence</atitle><jtitle>Phytochemistry (Oxford)</jtitle><addtitle>Phytochemistry</addtitle><date>2014-04-01</date><risdate>2014</risdate><volume>100</volume><spage>126</spage><epage>131</epage><pages>126-131</pages><issn>0031-9422</issn><eissn>1873-3700</eissn><abstract>Iteamine, o-aminobenzyl β-d-glucopyranoside, is the first alkaloid isolated from Itea, the only plant source of the rare sugar d-psicose in development as a zero calorie food.
•The discovery of iteamine, the first alkaloid isolated from Itea virginica.•Confirmation of the structure of iteamine by synthesis, and the synthesis of the galacto-epimer.•The galacto-epimer of iteamine showed weak but interesting inhibition of alpha-GalNAcase.
Iteamine, o-aminobenzyl β-d-glucopyranoside, is the first alkaloid to be isolated from Itea virginica. Itea is the sole plant source of d-psicose, a rare sugar likely to be a major dietary supplement. The structure of iteamine was established by NMR and confirmed by total synthesis. Iteamine and its galacto-analog (which was not found in Itea plants) showed no strong inhibition of any of the 15 glycosidases tested; unnatural galacto-iteamine was a weak inhibitor of chicken liver α-N-acetylgalactosaminidase.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>24534106</pmid><doi>10.1016/j.phytochem.2014.01.012</doi><tpages>6</tpages></addata></record> |
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| subjects | Alkaloids - chemistry Alkaloids - isolation & purification Alkaloids - pharmacology alpha-N-Acetylgalactosaminidase - antagonists & inhibitors Animals d-Psicose Enzyme Inhibitors - chemistry Enzyme Inhibitors - isolation & purification Enzyme Inhibitors - pharmacology Glucosides Grossulariaceae Inflorescence - chemistry Itea virginica Iteamine Tracheophyta - chemistry α-N-acetylgalactosaminidase |
| title | Iteamine, the first alkaloid isolated from Itea virginica L. inflorescence |
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