Chemical-microbiological synthesis of ent-13- epi-manoyl oxides with biological activities
The biotransformation of ent-13- epi-3-keto manoyl oxide, which possesses antileishmania activity, with Curvularia lunata produced ent-6β-hydroxy, ent-1βa-hydroxy, ent-11β-hydroxy and Δ 1- derivatives, as well as a reduction product at C-3 (S-alcohol) with another hydroxyl group at C-6 ( ent-6β) or...
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| Veröffentlicht in: | Phytochemistry (Oxford) 1994-10, Vol.37 (3), p.741-747 |
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| container_title | Phytochemistry (Oxford) |
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| creator | García-Granados, Andrés Belinda Jiménez, M a Martínez, Antonio Parra, Andrés Rivas, Francisco María Arias, José |
| description | The biotransformation of
ent-13-
epi-3-keto manoyl oxide, which possesses antileishmania activity, with
Curvularia lunata produced
ent-6β-hydroxy,
ent-1βa-hydroxy,
ent-11β-hydroxy and Δ
1- derivatives, as well as a reduction product at C-3 (S-alcohol) with another hydroxyl group at C-6 (
ent-6β) or C-11 (
ent-11β). The
ent-6β- hydroxy and Δ
1-derivatives inhibited growth ofthe pathogenic protozoa,
Leishmania donovani. The biotransformation of
ent- 12α-acetoxy-3β-hydroxy-13-
epi-manoyl oxide and
ent-3β-acetoxy-12-oxo-13-
epi-manoyl oxide gave the
ent-6β- hydroxyl derivatives. The incubation of
ent-3β-acetoxy -12β-dihydroxy-13-
epi-manoyl oxide gave
ent-3β,12β- dihydroxy-13-
epi-manoyl oxide and
ent-3β,6β,12β - trihydroxy-13-
epi-manoyl oxide (trimanoyl). Both products increased the activity of adenylatecyclase. |
| doi_str_mv | 10.1016/S0031-9422(00)90350-9 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_76925120</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0031942200903509</els_id><sourcerecordid>76925120</sourcerecordid><originalsourceid>FETCH-LOGICAL-c384t-2dabe2c809b32a3fb38de4fc2e87e707ea97cea08fc248fa1f0867b2ff2b20f3</originalsourceid><addsrcrecordid>eNqFkMtOxCAUhonR6Hh5BGNXRhfoAdpCV8ZMvCUmLkY3bgilBwfTlrF01Hl7O5cYd24gnPP9cPgIOWZwwYDllxMAwWiRcn4GcF6AyIAWW2TElBRUSIBtMvpF9sh-jO8AkGV5vkt2pcyzXKkReR1PsfHW1HRYu1D6UIe35TmJi7afYvQxCS7BtqdM0ARnnjamDYs6Cd--wph8-X6a_IkZ2_tP33uMh2THmTri0WY_IM-3N8_je_r4dPcwvn6kVqi0p7wyJXKroCgFN8KVQlWYOstRSZQg0RTSogE1lFLlDHOgclly53jJwYkDcrq-dtaFjznGXjc-Wqxr02KYRy3zgmeMwwBma3D4Z4wdOj3rfGO6hWagl0r1Sqle-tIAeqVUF0PuePPAvGyw-k1tHA79k3XfmaDNW-ejfplwYAJYWuSZWBJXawIHDZ8eOx2tx9Zi5Tu0va6C_2eGH9otkLk</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>76925120</pqid></control><display><type>article</type><title>Chemical-microbiological synthesis of ent-13- epi-manoyl oxides with biological activities</title><source>MEDLINE</source><source>Elsevier ScienceDirect Journals Complete</source><creator>García-Granados, Andrés ; Belinda Jiménez, M a ; Martínez, Antonio ; Parra, Andrés ; Rivas, Francisco ; María Arias, José</creator><creatorcontrib>García-Granados, Andrés ; Belinda Jiménez, M a ; Martínez, Antonio ; Parra, Andrés ; Rivas, Francisco ; María Arias, José</creatorcontrib><description>The biotransformation of
ent-13-
epi-3-keto manoyl oxide, which possesses antileishmania activity, with
Curvularia lunata produced
ent-6β-hydroxy,
ent-1βa-hydroxy,
ent-11β-hydroxy and Δ
1- derivatives, as well as a reduction product at C-3 (S-alcohol) with another hydroxyl group at C-6 (
ent-6β) or C-11 (
ent-11β). The
ent-6β- hydroxy and Δ
1-derivatives inhibited growth ofthe pathogenic protozoa,
Leishmania donovani. The biotransformation of
ent- 12α-acetoxy-3β-hydroxy-13-
epi-manoyl oxide and
ent-3β-acetoxy-12-oxo-13-
epi-manoyl oxide gave the
ent-6β- hydroxyl derivatives. The incubation of
ent-3β-acetoxy -12β-dihydroxy-13-
epi-manoyl oxide gave
ent-3β,12β- dihydroxy-13-
epi-manoyl oxide and
ent-3β,6β,12β - trihydroxy-13-
epi-manoyl oxide (trimanoyl). Both products increased the activity of adenylatecyclase.</description><identifier>ISSN: 0031-9422</identifier><identifier>EISSN: 1873-3700</identifier><identifier>DOI: 10.1016/S0031-9422(00)90350-9</identifier><identifier>PMID: 7765688</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>adenylatecyclase activator ; Animals ; antileishmanic activity ; antiprotozoal agents ; Antiprotozoal Agents - chemical synthesis ; Antiprotozoal Agents - metabolism ; Antiprotozoal Agents - pharmacology ; biosynthesis ; Biotechnology ; biotransformation ; Carbohydrate Sequence ; chemical reactions ; chemical structure ; Cochliobolus lunatus ; Curvularia lunata ; ent-13- epi-manoyl oxides ; Leishmania donovani - drug effects ; Leishmania donovani - metabolism ; leishmaniasis ; Magnetic Resonance Spectroscopy ; metabolites ; Mitosporic Fungi - metabolism ; molecular conformation ; Molecular Sequence Data ; oxides ; Oxides - metabolism ; precursors ; spectral analysis ; Spectrophotometry, Infrared ; Terpenes - chemical synthesis ; Terpenes - metabolism ; Terpenes - pharmacology</subject><ispartof>Phytochemistry (Oxford), 1994-10, Vol.37 (3), p.741-747</ispartof><rights>1994</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c384t-2dabe2c809b32a3fb38de4fc2e87e707ea97cea08fc248fa1f0867b2ff2b20f3</citedby><cites>FETCH-LOGICAL-c384t-2dabe2c809b32a3fb38de4fc2e87e707ea97cea08fc248fa1f0867b2ff2b20f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/S0031-9422(00)90350-9$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/7765688$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>García-Granados, Andrés</creatorcontrib><creatorcontrib>Belinda Jiménez, M a</creatorcontrib><creatorcontrib>Martínez, Antonio</creatorcontrib><creatorcontrib>Parra, Andrés</creatorcontrib><creatorcontrib>Rivas, Francisco</creatorcontrib><creatorcontrib>María Arias, José</creatorcontrib><title>Chemical-microbiological synthesis of ent-13- epi-manoyl oxides with biological activities</title><title>Phytochemistry (Oxford)</title><addtitle>Phytochemistry</addtitle><description>The biotransformation of
ent-13-
epi-3-keto manoyl oxide, which possesses antileishmania activity, with
Curvularia lunata produced
ent-6β-hydroxy,
ent-1βa-hydroxy,
ent-11β-hydroxy and Δ
1- derivatives, as well as a reduction product at C-3 (S-alcohol) with another hydroxyl group at C-6 (
ent-6β) or C-11 (
ent-11β). The
ent-6β- hydroxy and Δ
1-derivatives inhibited growth ofthe pathogenic protozoa,
Leishmania donovani. The biotransformation of
ent- 12α-acetoxy-3β-hydroxy-13-
epi-manoyl oxide and
ent-3β-acetoxy-12-oxo-13-
epi-manoyl oxide gave the
ent-6β- hydroxyl derivatives. The incubation of
ent-3β-acetoxy -12β-dihydroxy-13-
epi-manoyl oxide gave
ent-3β,12β- dihydroxy-13-
epi-manoyl oxide and
ent-3β,6β,12β - trihydroxy-13-
epi-manoyl oxide (trimanoyl). Both products increased the activity of adenylatecyclase.</description><subject>adenylatecyclase activator</subject><subject>Animals</subject><subject>antileishmanic activity</subject><subject>antiprotozoal agents</subject><subject>Antiprotozoal Agents - chemical synthesis</subject><subject>Antiprotozoal Agents - metabolism</subject><subject>Antiprotozoal Agents - pharmacology</subject><subject>biosynthesis</subject><subject>Biotechnology</subject><subject>biotransformation</subject><subject>Carbohydrate Sequence</subject><subject>chemical reactions</subject><subject>chemical structure</subject><subject>Cochliobolus lunatus</subject><subject>Curvularia lunata</subject><subject>ent-13- epi-manoyl oxides</subject><subject>Leishmania donovani - drug effects</subject><subject>Leishmania donovani - metabolism</subject><subject>leishmaniasis</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>metabolites</subject><subject>Mitosporic Fungi - metabolism</subject><subject>molecular conformation</subject><subject>Molecular Sequence Data</subject><subject>oxides</subject><subject>Oxides - metabolism</subject><subject>precursors</subject><subject>spectral analysis</subject><subject>Spectrophotometry, Infrared</subject><subject>Terpenes - chemical synthesis</subject><subject>Terpenes - metabolism</subject><subject>Terpenes - pharmacology</subject><issn>0031-9422</issn><issn>1873-3700</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1994</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkMtOxCAUhonR6Hh5BGNXRhfoAdpCV8ZMvCUmLkY3bgilBwfTlrF01Hl7O5cYd24gnPP9cPgIOWZwwYDllxMAwWiRcn4GcF6AyIAWW2TElBRUSIBtMvpF9sh-jO8AkGV5vkt2pcyzXKkReR1PsfHW1HRYu1D6UIe35TmJi7afYvQxCS7BtqdM0ARnnjamDYs6Cd--wph8-X6a_IkZ2_tP33uMh2THmTri0WY_IM-3N8_je_r4dPcwvn6kVqi0p7wyJXKroCgFN8KVQlWYOstRSZQg0RTSogE1lFLlDHOgclly53jJwYkDcrq-dtaFjznGXjc-Wqxr02KYRy3zgmeMwwBma3D4Z4wdOj3rfGO6hWagl0r1Sqle-tIAeqVUF0PuePPAvGyw-k1tHA79k3XfmaDNW-ejfplwYAJYWuSZWBJXawIHDZ8eOx2tx9Zi5Tu0va6C_2eGH9otkLk</recordid><startdate>19941001</startdate><enddate>19941001</enddate><creator>García-Granados, Andrés</creator><creator>Belinda Jiménez, M a</creator><creator>Martínez, Antonio</creator><creator>Parra, Andrés</creator><creator>Rivas, Francisco</creator><creator>María Arias, José</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>7X8</scope></search><sort><creationdate>19941001</creationdate><title>Chemical-microbiological synthesis of ent-13- epi-manoyl oxides with biological activities</title><author>García-Granados, Andrés ; Belinda Jiménez, M a ; Martínez, Antonio ; Parra, Andrés ; Rivas, Francisco ; María Arias, José</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c384t-2dabe2c809b32a3fb38de4fc2e87e707ea97cea08fc248fa1f0867b2ff2b20f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1994</creationdate><topic>adenylatecyclase activator</topic><topic>Animals</topic><topic>antileishmanic activity</topic><topic>antiprotozoal agents</topic><topic>Antiprotozoal Agents - chemical synthesis</topic><topic>Antiprotozoal Agents - metabolism</topic><topic>Antiprotozoal Agents - pharmacology</topic><topic>biosynthesis</topic><topic>Biotechnology</topic><topic>biotransformation</topic><topic>Carbohydrate Sequence</topic><topic>chemical reactions</topic><topic>chemical structure</topic><topic>Cochliobolus lunatus</topic><topic>Curvularia lunata</topic><topic>ent-13- epi-manoyl oxides</topic><topic>Leishmania donovani - drug effects</topic><topic>Leishmania donovani - metabolism</topic><topic>leishmaniasis</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>metabolites</topic><topic>Mitosporic Fungi - metabolism</topic><topic>molecular conformation</topic><topic>Molecular Sequence Data</topic><topic>oxides</topic><topic>Oxides - metabolism</topic><topic>precursors</topic><topic>spectral analysis</topic><topic>Spectrophotometry, Infrared</topic><topic>Terpenes - chemical synthesis</topic><topic>Terpenes - metabolism</topic><topic>Terpenes - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>García-Granados, Andrés</creatorcontrib><creatorcontrib>Belinda Jiménez, M a</creatorcontrib><creatorcontrib>Martínez, Antonio</creatorcontrib><creatorcontrib>Parra, Andrés</creatorcontrib><creatorcontrib>Rivas, Francisco</creatorcontrib><creatorcontrib>María Arias, José</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>MEDLINE - Academic</collection><jtitle>Phytochemistry (Oxford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>García-Granados, Andrés</au><au>Belinda Jiménez, M a</au><au>Martínez, Antonio</au><au>Parra, Andrés</au><au>Rivas, Francisco</au><au>María Arias, José</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chemical-microbiological synthesis of ent-13- epi-manoyl oxides with biological activities</atitle><jtitle>Phytochemistry (Oxford)</jtitle><addtitle>Phytochemistry</addtitle><date>1994-10-01</date><risdate>1994</risdate><volume>37</volume><issue>3</issue><spage>741</spage><epage>747</epage><pages>741-747</pages><issn>0031-9422</issn><eissn>1873-3700</eissn><abstract>The biotransformation of
ent-13-
epi-3-keto manoyl oxide, which possesses antileishmania activity, with
Curvularia lunata produced
ent-6β-hydroxy,
ent-1βa-hydroxy,
ent-11β-hydroxy and Δ
1- derivatives, as well as a reduction product at C-3 (S-alcohol) with another hydroxyl group at C-6 (
ent-6β) or C-11 (
ent-11β). The
ent-6β- hydroxy and Δ
1-derivatives inhibited growth ofthe pathogenic protozoa,
Leishmania donovani. The biotransformation of
ent- 12α-acetoxy-3β-hydroxy-13-
epi-manoyl oxide and
ent-3β-acetoxy-12-oxo-13-
epi-manoyl oxide gave the
ent-6β- hydroxyl derivatives. The incubation of
ent-3β-acetoxy -12β-dihydroxy-13-
epi-manoyl oxide gave
ent-3β,12β- dihydroxy-13-
epi-manoyl oxide and
ent-3β,6β,12β - trihydroxy-13-
epi-manoyl oxide (trimanoyl). Both products increased the activity of adenylatecyclase.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>7765688</pmid><doi>10.1016/S0031-9422(00)90350-9</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0031-9422 |
| ispartof | Phytochemistry (Oxford), 1994-10, Vol.37 (3), p.741-747 |
| issn | 0031-9422 1873-3700 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_76925120 |
| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | adenylatecyclase activator Animals antileishmanic activity antiprotozoal agents Antiprotozoal Agents - chemical synthesis Antiprotozoal Agents - metabolism Antiprotozoal Agents - pharmacology biosynthesis Biotechnology biotransformation Carbohydrate Sequence chemical reactions chemical structure Cochliobolus lunatus Curvularia lunata ent-13- epi-manoyl oxides Leishmania donovani - drug effects Leishmania donovani - metabolism leishmaniasis Magnetic Resonance Spectroscopy metabolites Mitosporic Fungi - metabolism molecular conformation Molecular Sequence Data oxides Oxides - metabolism precursors spectral analysis Spectrophotometry, Infrared Terpenes - chemical synthesis Terpenes - metabolism Terpenes - pharmacology |
| title | Chemical-microbiological synthesis of ent-13- epi-manoyl oxides with biological activities |
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