8- O-Acetylharpagide is a nonsteroidal ecdysteroid agonist
We have identified a novel nonsteroidal ecdysteroid agonist. This compound was isolated from a methanol extract of Ajuga reptans L. (Lamiaceae) and the structure was identified by spectroscopic methods as 8- O-acetylharpagide. We have characterised this compound as an ecdysteroid agonist in a transa...
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| Veröffentlicht in: | Insect biochemistry and molecular biology 1996-06, Vol.26 (6), p.519-523 |
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| container_issue | 6 |
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| container_title | Insect biochemistry and molecular biology |
| container_volume | 26 |
| creator | Elbrecht, Alex Chen, Yuli Jurgens, Tannis Hensens, Otto D. Zink, Debra L. Beck, Hans T. Balick, Michael J. Borris, Robert |
| description | We have identified a novel nonsteroidal ecdysteroid agonist. This compound was isolated from a methanol extract of
Ajuga reptans L. (Lamiaceae) and the structure was identified by spectroscopic methods as 8-
O-acetylharpagide. We have characterised this compound as an ecdysteroid agonist in a transactivation assay using β-galactosidase as the reporter gene regulated by ecdysteroid response elements. In this assay, 8-
O-acetylharpagide has an EC
50 of 22 μM. The compound also competes with tritiated-ponasterone A for binding to the
Drosophila ecdysteroid receptor. Finally, it induces differentiation of
Drosophila Kc cells as would be expected of an ecdysteroid agonist. This iridoid glycoside is common to several plant species and may play a role in the natural defense mechanisms of plants. |
| doi_str_mv | 10.1016/0965-1748(95)00103-4 |
| format | Article |
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Ajuga reptans L. (Lamiaceae) and the structure was identified by spectroscopic methods as 8-
O-acetylharpagide. We have characterised this compound as an ecdysteroid agonist in a transactivation assay using β-galactosidase as the reporter gene regulated by ecdysteroid response elements. In this assay, 8-
O-acetylharpagide has an EC
50 of 22 μM. The compound also competes with tritiated-ponasterone A for binding to the
Drosophila ecdysteroid receptor. Finally, it induces differentiation of
Drosophila Kc cells as would be expected of an ecdysteroid agonist. This iridoid glycoside is common to several plant species and may play a role in the natural defense mechanisms of plants.</description><identifier>ISSN: 0965-1748</identifier><identifier>EISSN: 1879-0240</identifier><identifier>DOI: 10.1016/0965-1748(95)00103-4</identifier><identifier>PMID: 8969463</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>agonists ; Ajuga reptans ; Animals ; beta-galactosidase ; binding sites ; cell differentiation ; cell lines ; Drosophila ; Drosophila - metabolism ; Drosophila melanogaster ; Ecdysteroid ; ecdysteroids ; ecdysterone ; Ecdysterone - agonists ; Ecdysterone - metabolism ; enzyme activity ; hormonal regulation ; hormone receptors ; Insect Hormones ; Insecticide ; iridoid glycosides ; Molecular Structure ; Plant Extracts ; Plants - metabolism ; Pyrans - chemistry ; Pyrans - metabolism ; Receptor ; Receptors, Steroid - metabolism ; reporter genes ; transcriptional activation</subject><ispartof>Insect biochemistry and molecular biology, 1996-06, Vol.26 (6), p.519-523</ispartof><rights>1996</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c412t-13c62eef2a0f0eaee8ae7e1b496a9f72a123ac9ad8ae9dc5ce57251803a7c6e83</citedby><cites>FETCH-LOGICAL-c412t-13c62eef2a0f0eaee8ae7e1b496a9f72a123ac9ad8ae9dc5ce57251803a7c6e83</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/0965-1748(95)00103-4$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,777,781,3537,27905,27906,45976</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/8969463$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Elbrecht, Alex</creatorcontrib><creatorcontrib>Chen, Yuli</creatorcontrib><creatorcontrib>Jurgens, Tannis</creatorcontrib><creatorcontrib>Hensens, Otto D.</creatorcontrib><creatorcontrib>Zink, Debra L.</creatorcontrib><creatorcontrib>Beck, Hans T.</creatorcontrib><creatorcontrib>Balick, Michael J.</creatorcontrib><creatorcontrib>Borris, Robert</creatorcontrib><title>8- O-Acetylharpagide is a nonsteroidal ecdysteroid agonist</title><title>Insect biochemistry and molecular biology</title><addtitle>Insect Biochem Mol Biol</addtitle><description>We have identified a novel nonsteroidal ecdysteroid agonist. This compound was isolated from a methanol extract of
Ajuga reptans L. (Lamiaceae) and the structure was identified by spectroscopic methods as 8-
O-acetylharpagide. We have characterised this compound as an ecdysteroid agonist in a transactivation assay using β-galactosidase as the reporter gene regulated by ecdysteroid response elements. In this assay, 8-
O-acetylharpagide has an EC
50 of 22 μM. The compound also competes with tritiated-ponasterone A for binding to the
Drosophila ecdysteroid receptor. Finally, it induces differentiation of
Drosophila Kc cells as would be expected of an ecdysteroid agonist. This iridoid glycoside is common to several plant species and may play a role in the natural defense mechanisms of plants.</description><subject>agonists</subject><subject>Ajuga reptans</subject><subject>Animals</subject><subject>beta-galactosidase</subject><subject>binding sites</subject><subject>cell differentiation</subject><subject>cell lines</subject><subject>Drosophila</subject><subject>Drosophila - metabolism</subject><subject>Drosophila melanogaster</subject><subject>Ecdysteroid</subject><subject>ecdysteroids</subject><subject>ecdysterone</subject><subject>Ecdysterone - agonists</subject><subject>Ecdysterone - metabolism</subject><subject>enzyme activity</subject><subject>hormonal regulation</subject><subject>hormone receptors</subject><subject>Insect Hormones</subject><subject>Insecticide</subject><subject>iridoid glycosides</subject><subject>Molecular Structure</subject><subject>Plant Extracts</subject><subject>Plants - metabolism</subject><subject>Pyrans - chemistry</subject><subject>Pyrans - metabolism</subject><subject>Receptor</subject><subject>Receptors, Steroid - metabolism</subject><subject>reporter genes</subject><subject>transcriptional activation</subject><issn>0965-1748</issn><issn>1879-0240</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1996</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkEtrG0EMgIfQ4Lhp_0FK9xTawyaa2XnmEAghLwj4kPo8yLNad8J6151ZB_zvs65Nju1JSPokpI-xMw4XHLi-BKdVyY20P5z6CcChKuURm3JrXAlCwic2_UBO2OecXwFASmUmbGKddlJXU3Zly2JW3gQatu1vTGtcxpqKmAssur7LA6U-1tgWFOrtIStw2XcxD1_YcYNtpq-HeMrm93e_bh_L59nD0-3NcxkkF0PJq6AFUSMQGiAkskiG-EI6ja4xArmoMDisx7qrgwqkjFDcQoUmaLLVKTvf712n_s-G8uBXMQdqW-yo32RvrOZOy_-DXFnljNiBcg-G1OecqPHrFFeYtp6D37n1O3F-J8475f-69XIc-3bYv1msqP4YOsgc-9_3_QZ7j8sUs5-_COAVcDV-BG4krvcEjb7eIiWfQ6QuUB0ThcHXffz3Ce-wM5Ev</recordid><startdate>19960601</startdate><enddate>19960601</enddate><creator>Elbrecht, Alex</creator><creator>Chen, Yuli</creator><creator>Jurgens, Tannis</creator><creator>Hensens, Otto D.</creator><creator>Zink, Debra L.</creator><creator>Beck, Hans T.</creator><creator>Balick, Michael J.</creator><creator>Borris, Robert</creator><general>Elsevier Ltd</general><scope>FBQ</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>7SS</scope><scope>7X8</scope></search><sort><creationdate>19960601</creationdate><title>8- O-Acetylharpagide is a nonsteroidal ecdysteroid agonist</title><author>Elbrecht, Alex ; Chen, Yuli ; Jurgens, Tannis ; Hensens, Otto D. ; Zink, Debra L. ; Beck, Hans T. ; Balick, Michael J. ; Borris, Robert</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c412t-13c62eef2a0f0eaee8ae7e1b496a9f72a123ac9ad8ae9dc5ce57251803a7c6e83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1996</creationdate><topic>agonists</topic><topic>Ajuga reptans</topic><topic>Animals</topic><topic>beta-galactosidase</topic><topic>binding sites</topic><topic>cell differentiation</topic><topic>cell lines</topic><topic>Drosophila</topic><topic>Drosophila - metabolism</topic><topic>Drosophila melanogaster</topic><topic>Ecdysteroid</topic><topic>ecdysteroids</topic><topic>ecdysterone</topic><topic>Ecdysterone - agonists</topic><topic>Ecdysterone - metabolism</topic><topic>enzyme activity</topic><topic>hormonal regulation</topic><topic>hormone receptors</topic><topic>Insect Hormones</topic><topic>Insecticide</topic><topic>iridoid glycosides</topic><topic>Molecular Structure</topic><topic>Plant Extracts</topic><topic>Plants - metabolism</topic><topic>Pyrans - chemistry</topic><topic>Pyrans - metabolism</topic><topic>Receptor</topic><topic>Receptors, Steroid - metabolism</topic><topic>reporter genes</topic><topic>transcriptional activation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Elbrecht, Alex</creatorcontrib><creatorcontrib>Chen, Yuli</creatorcontrib><creatorcontrib>Jurgens, Tannis</creatorcontrib><creatorcontrib>Hensens, Otto D.</creatorcontrib><creatorcontrib>Zink, Debra L.</creatorcontrib><creatorcontrib>Beck, Hans T.</creatorcontrib><creatorcontrib>Balick, Michael J.</creatorcontrib><creatorcontrib>Borris, Robert</creatorcontrib><collection>AGRIS</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Entomology Abstracts (Full archive)</collection><collection>MEDLINE - Academic</collection><jtitle>Insect biochemistry and molecular biology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Elbrecht, Alex</au><au>Chen, Yuli</au><au>Jurgens, Tannis</au><au>Hensens, Otto D.</au><au>Zink, Debra L.</au><au>Beck, Hans T.</au><au>Balick, Michael J.</au><au>Borris, Robert</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>8- O-Acetylharpagide is a nonsteroidal ecdysteroid agonist</atitle><jtitle>Insect biochemistry and molecular biology</jtitle><addtitle>Insect Biochem Mol Biol</addtitle><date>1996-06-01</date><risdate>1996</risdate><volume>26</volume><issue>6</issue><spage>519</spage><epage>523</epage><pages>519-523</pages><issn>0965-1748</issn><eissn>1879-0240</eissn><abstract>We have identified a novel nonsteroidal ecdysteroid agonist. This compound was isolated from a methanol extract of
Ajuga reptans L. (Lamiaceae) and the structure was identified by spectroscopic methods as 8-
O-acetylharpagide. We have characterised this compound as an ecdysteroid agonist in a transactivation assay using β-galactosidase as the reporter gene regulated by ecdysteroid response elements. In this assay, 8-
O-acetylharpagide has an EC
50 of 22 μM. The compound also competes with tritiated-ponasterone A for binding to the
Drosophila ecdysteroid receptor. Finally, it induces differentiation of
Drosophila Kc cells as would be expected of an ecdysteroid agonist. This iridoid glycoside is common to several plant species and may play a role in the natural defense mechanisms of plants.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>8969463</pmid><doi>10.1016/0965-1748(95)00103-4</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0965-1748 |
| ispartof | Insect biochemistry and molecular biology, 1996-06, Vol.26 (6), p.519-523 |
| issn | 0965-1748 1879-0240 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_78619648 |
| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | agonists Ajuga reptans Animals beta-galactosidase binding sites cell differentiation cell lines Drosophila Drosophila - metabolism Drosophila melanogaster Ecdysteroid ecdysteroids ecdysterone Ecdysterone - agonists Ecdysterone - metabolism enzyme activity hormonal regulation hormone receptors Insect Hormones Insecticide iridoid glycosides Molecular Structure Plant Extracts Plants - metabolism Pyrans - chemistry Pyrans - metabolism Receptor Receptors, Steroid - metabolism reporter genes transcriptional activation |
| title | 8- O-Acetylharpagide is a nonsteroidal ecdysteroid agonist |
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