Indole alkaloids of a Thai medicinal herb, Mitragyna speciosa, that has opioid agonistic effect in guinea-pig ileum
Abstract Recently, we found that mitragynine, a major constituent of MITRAGYNA SPECIOSA, has an opioid agonistic activity, but its weak potency could not explain the opium-like effect of this plant. In the present study, bioassay-guided fractionation of the crude extract of the leaves of M. SPECIOSA...
Gespeichert in:
| Veröffentlicht in: | Planta medica 2005-03, Vol.71 (3), p.231-236 |
|---|---|
| Hauptverfasser: | , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 236 |
|---|---|
| container_issue | 3 |
| container_start_page | 231 |
| container_title | Planta medica |
| container_volume | 71 |
| creator | Horie, S Koyama, F Takayama, H Ishikawa, H Aimi, N Ponglux, D Matsumoto, K Murayama, T |
| description | Abstract
Recently, we found that mitragynine, a major constituent of MITRAGYNA SPECIOSA, has an opioid agonistic activity, but its weak potency could not explain the opium-like effect of this plant. In the present study, bioassay-guided fractionation of the crude extract of the leaves of M. SPECIOSA was carried out to search for potent opioid agonists other than mitragynine. Opioid agonistic activities were evaluated using twitch contraction induced by electrical stimulation in guinea-pig ileum. The crude extract of M. SPECIOSA inhibited the twitch contraction in a concentration-dependent manner. The inhibition was reversed by naloxone. The opioid effect was detected only in the crude base fraction, which was followed by the isolation of five indole alkaloids. Among these alkaloids, 7-hydroxymitragynine showed the most potent opioid effect on the electrically-stimulated contraction (pD
2
= 8.38 ± 0.12). The potency, calculated using pD
2
values, was 30- and 17-fold higher than that of mitragynine and morphine, respectively. Antagonism of naloxone on concentration-response curves for 7-hydroxymitragynine confirmed its opioid effect. These results suggest that the opioid effect of M. SPECIOSA is mostly based on the activity of 7-hydroxymitragynine. |
| doi_str_mv | 10.1055/s-2005-837822 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_proquest_miscellaneous_67522576</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>67522576</sourcerecordid><originalsourceid>FETCH-LOGICAL-c344t-3f303debfff2489a47b5c992d3035a9a919ce7e9db1eb2a50752f053652ccc0d3</originalsourceid><addsrcrecordid>eNpF0Utv1DAUBWALUbVD6ZIteAOrCVy_kvGyqnhUasWCdm3dOHbi4sQhThb997iaQaws2d-5ku8h5B2DzwyU-pIrDqCqg2gOnL8iOyaFroBz9prsAASvQEtxQd7k_ATApAY4JxdMNQ0oKXYk305dio5i_I0xhS7T5CnShwEDHV0XbJgw0sEt7Z7eh3XB_nlCmmdnQ8q4p-uAKx2wxOZQ4hT7NIW8Bkud986uNEy038LksJpDT0N02_iWnHmM2V2dzkvy-O3rw82P6u7n99ub67vKCinXSngBonOt957Lg0bZtMpqzbtyrVCjZtq6xumuZa7lqKBR3IMSteLWWujEJfl0nDsv6c_m8mrGkK2LESeXtmzqEuCqqQt8f4JbWz5t5iWMuDybf2sq4OMJYLYY_YKTDfm_q2veMKGL2x_dOgQ3OvOUtqXsLxsG5qUtk81LW-bYVuEfjtxjMtgvZeTjLw5MAOjyLpn4C3yQjZ0</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>67522576</pqid></control><display><type>article</type><title>Indole alkaloids of a Thai medicinal herb, Mitragyna speciosa, that has opioid agonistic effect in guinea-pig ileum</title><source>MEDLINE</source><source>Thieme Connect Journals</source><creator>Horie, S ; Koyama, F ; Takayama, H ; Ishikawa, H ; Aimi, N ; Ponglux, D ; Matsumoto, K ; Murayama, T</creator><creatorcontrib>Horie, S ; Koyama, F ; Takayama, H ; Ishikawa, H ; Aimi, N ; Ponglux, D ; Matsumoto, K ; Murayama, T</creatorcontrib><description>Abstract
Recently, we found that mitragynine, a major constituent of MITRAGYNA SPECIOSA, has an opioid agonistic activity, but its weak potency could not explain the opium-like effect of this plant. In the present study, bioassay-guided fractionation of the crude extract of the leaves of M. SPECIOSA was carried out to search for potent opioid agonists other than mitragynine. Opioid agonistic activities were evaluated using twitch contraction induced by electrical stimulation in guinea-pig ileum. The crude extract of M. SPECIOSA inhibited the twitch contraction in a concentration-dependent manner. The inhibition was reversed by naloxone. The opioid effect was detected only in the crude base fraction, which was followed by the isolation of five indole alkaloids. Among these alkaloids, 7-hydroxymitragynine showed the most potent opioid effect on the electrically-stimulated contraction (pD
2
= 8.38 ± 0.12). The potency, calculated using pD
2
values, was 30- and 17-fold higher than that of mitragynine and morphine, respectively. Antagonism of naloxone on concentration-response curves for 7-hydroxymitragynine confirmed its opioid effect. These results suggest that the opioid effect of M. SPECIOSA is mostly based on the activity of 7-hydroxymitragynine.</description><identifier>ISSN: 0032-0943</identifier><identifier>EISSN: 1439-0221</identifier><identifier>DOI: 10.1055/s-2005-837822</identifier><identifier>PMID: 15770543</identifier><identifier>CODEN: PLMEAA</identifier><language>eng</language><publisher>Stuttgart: Thieme</publisher><subject>7-hydroxymitragynine ; Analgesics, Opioid - administration & dosage ; Analgesics, Opioid - pharmacology ; Analgesics, Opioid - therapeutic use ; Animals ; Biological and medical sciences ; chemical structure ; Dose-Response Relationship, Drug ; Electric Stimulation ; General pharmacology ; Guinea Pigs ; ileum ; Ileum - drug effects ; indole alkaloids ; Indole Alkaloids - administration & dosage ; Indole Alkaloids - pharmacology ; Indole Alkaloids - therapeutic use ; kratom ; Male ; Medical sciences ; medicinal plants ; Medicine, Traditional ; Mitragyna ; Mitragyna speciosa ; mitragynine ; muscle contraction ; Muscle Contraction - drug effects ; narcotics ; Original Paper ; paynantheine ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; phytochemicals ; Phytotherapy ; plant extracts ; Plant Extracts - administration & dosage ; Plant Extracts - pharmacology ; Plant Extracts - therapeutic use ; Plant Leaves ; Receptors, Opioid - drug effects ; Rubiaceae ; Secologanin Tryptamine Alkaloids - administration & dosage ; Secologanin Tryptamine Alkaloids - pharmacology ; Secologanin Tryptamine Alkaloids - therapeutic use ; speciociliatine ; speciogynine ; Thailand</subject><ispartof>Planta medica, 2005-03, Vol.71 (3), p.231-236</ispartof><rights>Georg Thieme Verlag KG Stuttgart · New York</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c344t-3f303debfff2489a47b5c992d3035a9a919ce7e9db1eb2a50752f053652ccc0d3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2005-837822.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-2005-837822$$EHTML$$P50$$Gthieme$$H</linktohtml><link.rule.ids>314,780,784,3016,27923,27924,54558,54559</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16627139$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15770543$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Horie, S</creatorcontrib><creatorcontrib>Koyama, F</creatorcontrib><creatorcontrib>Takayama, H</creatorcontrib><creatorcontrib>Ishikawa, H</creatorcontrib><creatorcontrib>Aimi, N</creatorcontrib><creatorcontrib>Ponglux, D</creatorcontrib><creatorcontrib>Matsumoto, K</creatorcontrib><creatorcontrib>Murayama, T</creatorcontrib><title>Indole alkaloids of a Thai medicinal herb, Mitragyna speciosa, that has opioid agonistic effect in guinea-pig ileum</title><title>Planta medica</title><addtitle>Planta Med</addtitle><description>Abstract
Recently, we found that mitragynine, a major constituent of MITRAGYNA SPECIOSA, has an opioid agonistic activity, but its weak potency could not explain the opium-like effect of this plant. In the present study, bioassay-guided fractionation of the crude extract of the leaves of M. SPECIOSA was carried out to search for potent opioid agonists other than mitragynine. Opioid agonistic activities were evaluated using twitch contraction induced by electrical stimulation in guinea-pig ileum. The crude extract of M. SPECIOSA inhibited the twitch contraction in a concentration-dependent manner. The inhibition was reversed by naloxone. The opioid effect was detected only in the crude base fraction, which was followed by the isolation of five indole alkaloids. Among these alkaloids, 7-hydroxymitragynine showed the most potent opioid effect on the electrically-stimulated contraction (pD
2
= 8.38 ± 0.12). The potency, calculated using pD
2
values, was 30- and 17-fold higher than that of mitragynine and morphine, respectively. Antagonism of naloxone on concentration-response curves for 7-hydroxymitragynine confirmed its opioid effect. These results suggest that the opioid effect of M. SPECIOSA is mostly based on the activity of 7-hydroxymitragynine.</description><subject>7-hydroxymitragynine</subject><subject>Analgesics, Opioid - administration & dosage</subject><subject>Analgesics, Opioid - pharmacology</subject><subject>Analgesics, Opioid - therapeutic use</subject><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>chemical structure</subject><subject>Dose-Response Relationship, Drug</subject><subject>Electric Stimulation</subject><subject>General pharmacology</subject><subject>Guinea Pigs</subject><subject>ileum</subject><subject>Ileum - drug effects</subject><subject>indole alkaloids</subject><subject>Indole Alkaloids - administration & dosage</subject><subject>Indole Alkaloids - pharmacology</subject><subject>Indole Alkaloids - therapeutic use</subject><subject>kratom</subject><subject>Male</subject><subject>Medical sciences</subject><subject>medicinal plants</subject><subject>Medicine, Traditional</subject><subject>Mitragyna</subject><subject>Mitragyna speciosa</subject><subject>mitragynine</subject><subject>muscle contraction</subject><subject>Muscle Contraction - drug effects</subject><subject>narcotics</subject><subject>Original Paper</subject><subject>paynantheine</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>phytochemicals</subject><subject>Phytotherapy</subject><subject>plant extracts</subject><subject>Plant Extracts - administration & dosage</subject><subject>Plant Extracts - pharmacology</subject><subject>Plant Extracts - therapeutic use</subject><subject>Plant Leaves</subject><subject>Receptors, Opioid - drug effects</subject><subject>Rubiaceae</subject><subject>Secologanin Tryptamine Alkaloids - administration & dosage</subject><subject>Secologanin Tryptamine Alkaloids - pharmacology</subject><subject>Secologanin Tryptamine Alkaloids - therapeutic use</subject><subject>speciociliatine</subject><subject>speciogynine</subject><subject>Thailand</subject><issn>0032-0943</issn><issn>1439-0221</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpF0Utv1DAUBWALUbVD6ZIteAOrCVy_kvGyqnhUasWCdm3dOHbi4sQhThb997iaQaws2d-5ku8h5B2DzwyU-pIrDqCqg2gOnL8iOyaFroBz9prsAASvQEtxQd7k_ATApAY4JxdMNQ0oKXYk305dio5i_I0xhS7T5CnShwEDHV0XbJgw0sEt7Z7eh3XB_nlCmmdnQ8q4p-uAKx2wxOZQ4hT7NIW8Bkud986uNEy038LksJpDT0N02_iWnHmM2V2dzkvy-O3rw82P6u7n99ub67vKCinXSngBonOt957Lg0bZtMpqzbtyrVCjZtq6xumuZa7lqKBR3IMSteLWWujEJfl0nDsv6c_m8mrGkK2LESeXtmzqEuCqqQt8f4JbWz5t5iWMuDybf2sq4OMJYLYY_YKTDfm_q2veMKGL2x_dOgQ3OvOUtqXsLxsG5qUtk81LW-bYVuEfjtxjMtgvZeTjLw5MAOjyLpn4C3yQjZ0</recordid><startdate>20050301</startdate><enddate>20050301</enddate><creator>Horie, S</creator><creator>Koyama, F</creator><creator>Takayama, H</creator><creator>Ishikawa, H</creator><creator>Aimi, N</creator><creator>Ponglux, D</creator><creator>Matsumoto, K</creator><creator>Murayama, T</creator><general>Thieme</general><scope>FBQ</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20050301</creationdate><title>Indole alkaloids of a Thai medicinal herb, Mitragyna speciosa, that has opioid agonistic effect in guinea-pig ileum</title><author>Horie, S ; Koyama, F ; Takayama, H ; Ishikawa, H ; Aimi, N ; Ponglux, D ; Matsumoto, K ; Murayama, T</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c344t-3f303debfff2489a47b5c992d3035a9a919ce7e9db1eb2a50752f053652ccc0d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>7-hydroxymitragynine</topic><topic>Analgesics, Opioid - administration & dosage</topic><topic>Analgesics, Opioid - pharmacology</topic><topic>Analgesics, Opioid - therapeutic use</topic><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>chemical structure</topic><topic>Dose-Response Relationship, Drug</topic><topic>Electric Stimulation</topic><topic>General pharmacology</topic><topic>Guinea Pigs</topic><topic>ileum</topic><topic>Ileum - drug effects</topic><topic>indole alkaloids</topic><topic>Indole Alkaloids - administration & dosage</topic><topic>Indole Alkaloids - pharmacology</topic><topic>Indole Alkaloids - therapeutic use</topic><topic>kratom</topic><topic>Male</topic><topic>Medical sciences</topic><topic>medicinal plants</topic><topic>Medicine, Traditional</topic><topic>Mitragyna</topic><topic>Mitragyna speciosa</topic><topic>mitragynine</topic><topic>muscle contraction</topic><topic>Muscle Contraction - drug effects</topic><topic>narcotics</topic><topic>Original Paper</topic><topic>paynantheine</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>phytochemicals</topic><topic>Phytotherapy</topic><topic>plant extracts</topic><topic>Plant Extracts - administration & dosage</topic><topic>Plant Extracts - pharmacology</topic><topic>Plant Extracts - therapeutic use</topic><topic>Plant Leaves</topic><topic>Receptors, Opioid - drug effects</topic><topic>Rubiaceae</topic><topic>Secologanin Tryptamine Alkaloids - administration & dosage</topic><topic>Secologanin Tryptamine Alkaloids - pharmacology</topic><topic>Secologanin Tryptamine Alkaloids - therapeutic use</topic><topic>speciociliatine</topic><topic>speciogynine</topic><topic>Thailand</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Horie, S</creatorcontrib><creatorcontrib>Koyama, F</creatorcontrib><creatorcontrib>Takayama, H</creatorcontrib><creatorcontrib>Ishikawa, H</creatorcontrib><creatorcontrib>Aimi, N</creatorcontrib><creatorcontrib>Ponglux, D</creatorcontrib><creatorcontrib>Matsumoto, K</creatorcontrib><creatorcontrib>Murayama, T</creatorcontrib><collection>AGRIS</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>MEDLINE - Academic</collection><jtitle>Planta medica</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Horie, S</au><au>Koyama, F</au><au>Takayama, H</au><au>Ishikawa, H</au><au>Aimi, N</au><au>Ponglux, D</au><au>Matsumoto, K</au><au>Murayama, T</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Indole alkaloids of a Thai medicinal herb, Mitragyna speciosa, that has opioid agonistic effect in guinea-pig ileum</atitle><jtitle>Planta medica</jtitle><addtitle>Planta Med</addtitle><date>2005-03-01</date><risdate>2005</risdate><volume>71</volume><issue>3</issue><spage>231</spage><epage>236</epage><pages>231-236</pages><issn>0032-0943</issn><eissn>1439-0221</eissn><coden>PLMEAA</coden><abstract>Abstract
Recently, we found that mitragynine, a major constituent of MITRAGYNA SPECIOSA, has an opioid agonistic activity, but its weak potency could not explain the opium-like effect of this plant. In the present study, bioassay-guided fractionation of the crude extract of the leaves of M. SPECIOSA was carried out to search for potent opioid agonists other than mitragynine. Opioid agonistic activities were evaluated using twitch contraction induced by electrical stimulation in guinea-pig ileum. The crude extract of M. SPECIOSA inhibited the twitch contraction in a concentration-dependent manner. The inhibition was reversed by naloxone. The opioid effect was detected only in the crude base fraction, which was followed by the isolation of five indole alkaloids. Among these alkaloids, 7-hydroxymitragynine showed the most potent opioid effect on the electrically-stimulated contraction (pD
2
= 8.38 ± 0.12). The potency, calculated using pD
2
values, was 30- and 17-fold higher than that of mitragynine and morphine, respectively. Antagonism of naloxone on concentration-response curves for 7-hydroxymitragynine confirmed its opioid effect. These results suggest that the opioid effect of M. SPECIOSA is mostly based on the activity of 7-hydroxymitragynine.</abstract><cop>Stuttgart</cop><cop>New York, NY</cop><pub>Thieme</pub><pmid>15770543</pmid><doi>10.1055/s-2005-837822</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0032-0943 |
| ispartof | Planta medica, 2005-03, Vol.71 (3), p.231-236 |
| issn | 0032-0943 1439-0221 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_67522576 |
| source | MEDLINE; Thieme Connect Journals |
| subjects | 7-hydroxymitragynine Analgesics, Opioid - administration & dosage Analgesics, Opioid - pharmacology Analgesics, Opioid - therapeutic use Animals Biological and medical sciences chemical structure Dose-Response Relationship, Drug Electric Stimulation General pharmacology Guinea Pigs ileum Ileum - drug effects indole alkaloids Indole Alkaloids - administration & dosage Indole Alkaloids - pharmacology Indole Alkaloids - therapeutic use kratom Male Medical sciences medicinal plants Medicine, Traditional Mitragyna Mitragyna speciosa mitragynine muscle contraction Muscle Contraction - drug effects narcotics Original Paper paynantheine Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments phytochemicals Phytotherapy plant extracts Plant Extracts - administration & dosage Plant Extracts - pharmacology Plant Extracts - therapeutic use Plant Leaves Receptors, Opioid - drug effects Rubiaceae Secologanin Tryptamine Alkaloids - administration & dosage Secologanin Tryptamine Alkaloids - pharmacology Secologanin Tryptamine Alkaloids - therapeutic use speciociliatine speciogynine Thailand |
| title | Indole alkaloids of a Thai medicinal herb, Mitragyna speciosa, that has opioid agonistic effect in guinea-pig ileum |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-12T23%3A06%3A28IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Indole%20alkaloids%20of%20a%20Thai%20medicinal%20herb,%20Mitragyna%20speciosa,%20that%20has%20opioid%20agonistic%20effect%20in%20guinea-pig%20ileum&rft.jtitle=Planta%20medica&rft.au=Horie,%20S&rft.date=2005-03-01&rft.volume=71&rft.issue=3&rft.spage=231&rft.epage=236&rft.pages=231-236&rft.issn=0032-0943&rft.eissn=1439-0221&rft.coden=PLMEAA&rft_id=info:doi/10.1055/s-2005-837822&rft_dat=%3Cproquest_pubme%3E67522576%3C/proquest_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=67522576&rft_id=info:pmid/15770543&rfr_iscdi=true |