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Geranylated Coumarins From Thai Medicinal Plant Mammea siamensis With Testosterone 5α-Reductase Inhibitory Activity
Geranylated coumarin constituents, kayeassamin I ( ) and mammeasins E ( ) and F ( ) were newly isolated from the methanol extract of the flowers of (Calophyllaceae) originating in Thailand, along with five known isolates, such as mammea E/BC ( ), deacetylmammea E/AA cyclo D ( ), deacetylmammea E/BB...
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| Published in: | Frontiers in chemistry 2020-03, Vol.8, p.199-199 |
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| Main Authors: | , , , , , , , , |
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| Language: | English |
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| container_end_page | 199 |
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| container_start_page | 199 |
| container_title | Frontiers in chemistry |
| container_volume | 8 |
| creator | Morikawa, Toshio Luo, Fenglin Manse, Yoshiaki Sugita, Hidemi Saeki, Shunsuke Chaipech, Saowanee Pongpiriyadacha, Yutana Muraoka, Osamu Ninomiya, Kiyofumi |
| description | Geranylated coumarin constituents, kayeassamin I (
) and mammeasins E (
) and F (
) were newly isolated from the methanol extract of the flowers of
(Calophyllaceae) originating in Thailand, along with five known isolates, such as mammea E/BC (
), deacetylmammea E/AA cyclo D (
), deacetylmammea E/BB cyclo D (
), mammea A/AA cyclo F (
), and mammea A/AC cyclo F (
). These compounds (
-
) were obtained as an inseparable mixture (
. 1:1 ratio) of the 3″
and 3″
forms, respectively. Among the isolated coumarins from the extract, mammeasins E (
, 22.6 μM), A (
, 19.0 μM), and B (
, 24.0 μM), kayeassamins E (
, 33.8 μM), F (
, 15.9 μM), and G (
, 17.7 μM), surangin C (
, 5.9 μM), and mammeas A/AA (
, 19.5 μM), E/BB (
, 16.8 μM), and A/AA cyclo F (
, 23.6 μM), were found to inhibit testosterone 5α-reductase. |
| doi_str_mv | 10.3389/fchem.2020.00199 |
| format | article |
| fullrecord | <record><control><sourceid>proquest_doaj_</sourceid><recordid>TN_cdi_doaj_primary_oai_doaj_org_article_53223d450a7040798e9070794e3ebb65</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><doaj_id>oai_doaj_org_article_53223d450a7040798e9070794e3ebb65</doaj_id><sourcerecordid>2387691889</sourcerecordid><originalsourceid>FETCH-LOGICAL-c462t-2c0f4d43d27d62d3eba17777aaf3afb25b5b6ef96d070ed9d2b50651361ef8333</originalsourceid><addsrcrecordid>eNpVkcFu3CAQhlHVqonS3HuqOPbiDQYbm0ulaNWkKyVqVW3VIxrDOCayTQo40j5WX6TPVLKbRAkX0PDPN_D_hHws2UqIVp31ZsBpxRlnK8ZKpd6QY86VLLis5NsX5yNyGuMtyxpeioqz9-RIcC4lL-UxSZcYYN6NkNDStV8mCG6O9CL4iW4HcPQarTNuhpH-GGFO9BqmCYFGBxPO0UX626WBbjEmHxMGPyOt__0tfqJdTIKIdDMPrnPJhx09N8ndu7T7QN71MEY8fdxPyK-Lr9v1t-Lq--VmfX5VmEryVHDD-spWwvLGSm4FdlA2eQH0AvqO113dSeyVtKxhaJXlXc1kXQpZYt8KIU7I5sC1Hm71XXD5dzvtwel9wYcbDSE5M6KusyXCVjWDhlWsUS2qDG1UhXlsJ-vM-nJg3S3dhNbgnAKMr6Cvb2Y36Bt_rxumFGdVBnx-BAT_Z8l-6clFg2N2Ff0SNRdtI1XZtipL2UFqgo8xYP88pmT6IXu9z14_ZK_32eeWTy-f99zwlLT4DyqlrXA</addsrcrecordid><sourcetype>Open Website</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2387691889</pqid></control><display><type>article</type><title>Geranylated Coumarins From Thai Medicinal Plant Mammea siamensis With Testosterone 5α-Reductase Inhibitory Activity</title><source>PubMed Central</source><creator>Morikawa, Toshio ; Luo, Fenglin ; Manse, Yoshiaki ; Sugita, Hidemi ; Saeki, Shunsuke ; Chaipech, Saowanee ; Pongpiriyadacha, Yutana ; Muraoka, Osamu ; Ninomiya, Kiyofumi</creator><creatorcontrib>Morikawa, Toshio ; Luo, Fenglin ; Manse, Yoshiaki ; Sugita, Hidemi ; Saeki, Shunsuke ; Chaipech, Saowanee ; Pongpiriyadacha, Yutana ; Muraoka, Osamu ; Ninomiya, Kiyofumi</creatorcontrib><description>Geranylated coumarin constituents, kayeassamin I (
) and mammeasins E (
) and F (
) were newly isolated from the methanol extract of the flowers of
(Calophyllaceae) originating in Thailand, along with five known isolates, such as mammea E/BC (
), deacetylmammea E/AA cyclo D (
), deacetylmammea E/BB cyclo D (
), mammea A/AA cyclo F (
), and mammea A/AC cyclo F (
). These compounds (
-
) were obtained as an inseparable mixture (
. 1:1 ratio) of the 3″
and 3″
forms, respectively. Among the isolated coumarins from the extract, mammeasins E (
, 22.6 μM), A (
, 19.0 μM), and B (
, 24.0 μM), kayeassamins E (
, 33.8 μM), F (
, 15.9 μM), and G (
, 17.7 μM), surangin C (
, 5.9 μM), and mammeas A/AA (
, 19.5 μM), E/BB (
, 16.8 μM), and A/AA cyclo F (
, 23.6 μM), were found to inhibit testosterone 5α-reductase.</description><identifier>ISSN: 2296-2646</identifier><identifier>EISSN: 2296-2646</identifier><identifier>DOI: 10.3389/fchem.2020.00199</identifier><identifier>PMID: 32266216</identifier><language>eng</language><publisher>Switzerland: Frontiers Media S.A</publisher><subject>5α-reductase inhibitor ; calophyllaceae ; Chemistry ; geranylated coumarin ; Mammea siamensis ; mammeasin</subject><ispartof>Frontiers in chemistry, 2020-03, Vol.8, p.199-199</ispartof><rights>Copyright © 2020 Morikawa, Luo, Manse, Sugita, Saeki, Chaipech, Pongpiriyadacha, Muraoka and Ninomiya.</rights><rights>Copyright © 2020 Morikawa, Luo, Manse, Sugita, Saeki, Chaipech, Pongpiriyadacha, Muraoka and Ninomiya. 2020 Morikawa, Luo, Manse, Sugita, Saeki, Chaipech, Pongpiriyadacha, Muraoka and Ninomiya</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c462t-2c0f4d43d27d62d3eba17777aaf3afb25b5b6ef96d070ed9d2b50651361ef8333</citedby><cites>FETCH-LOGICAL-c462t-2c0f4d43d27d62d3eba17777aaf3afb25b5b6ef96d070ed9d2b50651361ef8333</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC7099204/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC7099204/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,881,27901,27902,53766,53768</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32266216$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Morikawa, Toshio</creatorcontrib><creatorcontrib>Luo, Fenglin</creatorcontrib><creatorcontrib>Manse, Yoshiaki</creatorcontrib><creatorcontrib>Sugita, Hidemi</creatorcontrib><creatorcontrib>Saeki, Shunsuke</creatorcontrib><creatorcontrib>Chaipech, Saowanee</creatorcontrib><creatorcontrib>Pongpiriyadacha, Yutana</creatorcontrib><creatorcontrib>Muraoka, Osamu</creatorcontrib><creatorcontrib>Ninomiya, Kiyofumi</creatorcontrib><title>Geranylated Coumarins From Thai Medicinal Plant Mammea siamensis With Testosterone 5α-Reductase Inhibitory Activity</title><title>Frontiers in chemistry</title><addtitle>Front Chem</addtitle><description>Geranylated coumarin constituents, kayeassamin I (
) and mammeasins E (
) and F (
) were newly isolated from the methanol extract of the flowers of
(Calophyllaceae) originating in Thailand, along with five known isolates, such as mammea E/BC (
), deacetylmammea E/AA cyclo D (
), deacetylmammea E/BB cyclo D (
), mammea A/AA cyclo F (
), and mammea A/AC cyclo F (
). These compounds (
-
) were obtained as an inseparable mixture (
. 1:1 ratio) of the 3″
and 3″
forms, respectively. Among the isolated coumarins from the extract, mammeasins E (
, 22.6 μM), A (
, 19.0 μM), and B (
, 24.0 μM), kayeassamins E (
, 33.8 μM), F (
, 15.9 μM), and G (
, 17.7 μM), surangin C (
, 5.9 μM), and mammeas A/AA (
, 19.5 μM), E/BB (
, 16.8 μM), and A/AA cyclo F (
, 23.6 μM), were found to inhibit testosterone 5α-reductase.</description><subject>5α-reductase inhibitor</subject><subject>calophyllaceae</subject><subject>Chemistry</subject><subject>geranylated coumarin</subject><subject>Mammea siamensis</subject><subject>mammeasin</subject><issn>2296-2646</issn><issn>2296-2646</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>DOA</sourceid><recordid>eNpVkcFu3CAQhlHVqonS3HuqOPbiDQYbm0ulaNWkKyVqVW3VIxrDOCayTQo40j5WX6TPVLKbRAkX0PDPN_D_hHws2UqIVp31ZsBpxRlnK8ZKpd6QY86VLLis5NsX5yNyGuMtyxpeioqz9-RIcC4lL-UxSZcYYN6NkNDStV8mCG6O9CL4iW4HcPQarTNuhpH-GGFO9BqmCYFGBxPO0UX626WBbjEmHxMGPyOt__0tfqJdTIKIdDMPrnPJhx09N8ndu7T7QN71MEY8fdxPyK-Lr9v1t-Lq--VmfX5VmEryVHDD-spWwvLGSm4FdlA2eQH0AvqO113dSeyVtKxhaJXlXc1kXQpZYt8KIU7I5sC1Hm71XXD5dzvtwel9wYcbDSE5M6KusyXCVjWDhlWsUS2qDG1UhXlsJ-vM-nJg3S3dhNbgnAKMr6Cvb2Y36Bt_rxumFGdVBnx-BAT_Z8l-6clFg2N2Ff0SNRdtI1XZtipL2UFqgo8xYP88pmT6IXu9z14_ZK_32eeWTy-f99zwlLT4DyqlrXA</recordid><startdate>20200320</startdate><enddate>20200320</enddate><creator>Morikawa, Toshio</creator><creator>Luo, Fenglin</creator><creator>Manse, Yoshiaki</creator><creator>Sugita, Hidemi</creator><creator>Saeki, Shunsuke</creator><creator>Chaipech, Saowanee</creator><creator>Pongpiriyadacha, Yutana</creator><creator>Muraoka, Osamu</creator><creator>Ninomiya, Kiyofumi</creator><general>Frontiers Media S.A</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope></search><sort><creationdate>20200320</creationdate><title>Geranylated Coumarins From Thai Medicinal Plant Mammea siamensis With Testosterone 5α-Reductase Inhibitory Activity</title><author>Morikawa, Toshio ; Luo, Fenglin ; Manse, Yoshiaki ; Sugita, Hidemi ; Saeki, Shunsuke ; Chaipech, Saowanee ; Pongpiriyadacha, Yutana ; Muraoka, Osamu ; Ninomiya, Kiyofumi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c462t-2c0f4d43d27d62d3eba17777aaf3afb25b5b6ef96d070ed9d2b50651361ef8333</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>5α-reductase inhibitor</topic><topic>calophyllaceae</topic><topic>Chemistry</topic><topic>geranylated coumarin</topic><topic>Mammea siamensis</topic><topic>mammeasin</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Morikawa, Toshio</creatorcontrib><creatorcontrib>Luo, Fenglin</creatorcontrib><creatorcontrib>Manse, Yoshiaki</creatorcontrib><creatorcontrib>Sugita, Hidemi</creatorcontrib><creatorcontrib>Saeki, Shunsuke</creatorcontrib><creatorcontrib>Chaipech, Saowanee</creatorcontrib><creatorcontrib>Pongpiriyadacha, Yutana</creatorcontrib><creatorcontrib>Muraoka, Osamu</creatorcontrib><creatorcontrib>Ninomiya, Kiyofumi</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>Frontiers in chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Morikawa, Toshio</au><au>Luo, Fenglin</au><au>Manse, Yoshiaki</au><au>Sugita, Hidemi</au><au>Saeki, Shunsuke</au><au>Chaipech, Saowanee</au><au>Pongpiriyadacha, Yutana</au><au>Muraoka, Osamu</au><au>Ninomiya, Kiyofumi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Geranylated Coumarins From Thai Medicinal Plant Mammea siamensis With Testosterone 5α-Reductase Inhibitory Activity</atitle><jtitle>Frontiers in chemistry</jtitle><addtitle>Front Chem</addtitle><date>2020-03-20</date><risdate>2020</risdate><volume>8</volume><spage>199</spage><epage>199</epage><pages>199-199</pages><issn>2296-2646</issn><eissn>2296-2646</eissn><abstract>Geranylated coumarin constituents, kayeassamin I (
) and mammeasins E (
) and F (
) were newly isolated from the methanol extract of the flowers of
(Calophyllaceae) originating in Thailand, along with five known isolates, such as mammea E/BC (
), deacetylmammea E/AA cyclo D (
), deacetylmammea E/BB cyclo D (
), mammea A/AA cyclo F (
), and mammea A/AC cyclo F (
). These compounds (
-
) were obtained as an inseparable mixture (
. 1:1 ratio) of the 3″
and 3″
forms, respectively. Among the isolated coumarins from the extract, mammeasins E (
, 22.6 μM), A (
, 19.0 μM), and B (
, 24.0 μM), kayeassamins E (
, 33.8 μM), F (
, 15.9 μM), and G (
, 17.7 μM), surangin C (
, 5.9 μM), and mammeas A/AA (
, 19.5 μM), E/BB (
, 16.8 μM), and A/AA cyclo F (
, 23.6 μM), were found to inhibit testosterone 5α-reductase.</abstract><cop>Switzerland</cop><pub>Frontiers Media S.A</pub><pmid>32266216</pmid><doi>10.3389/fchem.2020.00199</doi><tpages>1</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Frontiers in chemistry, 2020-03, Vol.8, p.199-199 |
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| language | eng |
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| source | PubMed Central |
| subjects | 5α-reductase inhibitor calophyllaceae Chemistry geranylated coumarin Mammea siamensis mammeasin |
| title | Geranylated Coumarins From Thai Medicinal Plant Mammea siamensis With Testosterone 5α-Reductase Inhibitory Activity |
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