Muriceanol, a 24(28)-Epoxide Sterol Link in the Carbon Flux Toward Side-Chain Dealkylation of Sterols
Side‐chain‐oxidized C‐28‐sterol 1 and one new pregnane metabolite 2 were isolated from eastern Pacific Muricea spp. The C‐24(28)‐epoxide functionality is a key intermediate in the C‐24‐dealkylation mechanism of the conversion of phytosterol to cholesterol by phytophagous insects. Certain marine inve...
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| Veröffentlicht in: | European Journal of Organic Chemistry 2006-02, Vol.2006 (3), p.582-585 |
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| container_title | European Journal of Organic Chemistry |
| container_volume | 2006 |
| creator | Lorenzo, Manuel Cueto, Mercedes D'Croz, Luis Maté, Juan L. San-Martín, Aurelio Darias, José |
| description | Side‐chain‐oxidized C‐28‐sterol 1 and one new pregnane metabolite 2 were isolated from eastern Pacific Muricea spp. The C‐24(28)‐epoxide functionality is a key intermediate in the C‐24‐dealkylation mechanism of the conversion of phytosterol to cholesterol by phytophagous insects. Certain marine invertebrates share this dealkylation pathway; however, such a key epoxide feature has not yet been found in a naturally occurring sterol from marine invertebrates. The unusual oxidation pattern of the side chain of 1 encourages speculation about its biogenesis and converts this non‐zooxanthellate gorgonia into an interesting candidate organism for biosynthetic studies on C‐24‐dealkylation of phytosterols in octocorals. The (22S)‐22‐hydroxy group, after 24‐dealkylation of 1, may be an advantageous functionalization in the side‐chain cleavage to C‐21‐pregnane steroids in Muricea spp. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006) |
| doi_str_mv | 10.1002/ejoc.200500775 |
| format | Article |
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Certain marine invertebrates share this dealkylation pathway; however, such a key epoxide feature has not yet been found in a naturally occurring sterol from marine invertebrates. The unusual oxidation pattern of the side chain of 1 encourages speculation about its biogenesis and converts this non‐zooxanthellate gorgonia into an interesting candidate organism for biosynthetic studies on C‐24‐dealkylation of phytosterols in octocorals. The (22S)‐22‐hydroxy group, after 24‐dealkylation of 1, may be an advantageous functionalization in the side‐chain cleavage to C‐21‐pregnane steroids in Muricea spp. (© Wiley‐VCH Verlag GmbH & Co. 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KGaA, 69451 Weinheim, Germany, 2006)</description><subject>24-Epoxisterol</subject><subject>Biogenesis</subject><subject>Muricea spp</subject><subject>Non-zooxanthellate gorgonia</subject><subject>Octocoral</subject><subject>Pregnanes</subject><subject>Side-chain dealkylation</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><recordid>eNqFkM1PwjAYhxujiYhePfeoicW269b1aCYfEpREMHhr3q1dKExGuhHgv3cEQrx5et_D8_wOD0L3jHYYpfzZLsqswykNKZUyvEAtRpUiNFL0svlFIAhTwfc1uqmqBaVURRFrIfu-8S6zsCqLJwyYiwceP5Luutw5Y_Gktr4s8MitltitcD23OAGflivcKzY7PC234A2eNChJ5tAQrxaK5b6A2jVMmZ8Gqlt0lUNR2bvTbaOvXneaDMho3H9LXkYkC7gMSaoUy4Q0xrBcWiPDEAzPc2MgEqGBGGIp4tSI2IpI2VzY0KRAOaQsMEKkELRR57ib-bKqvM312rsf8HvNqD5E0odI-hypEdRR2LrC7v-hdXc4Tv665Oi6qra7swt-qSMZNPjso685GwwT-TnQs-AXZqF7Ew</recordid><startdate>200602</startdate><enddate>200602</enddate><creator>Lorenzo, Manuel</creator><creator>Cueto, Mercedes</creator><creator>D'Croz, Luis</creator><creator>Maté, Juan L.</creator><creator>San-Martín, Aurelio</creator><creator>Darias, José</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>200602</creationdate><title>Muriceanol, a 24(28)-Epoxide Sterol Link in the Carbon Flux Toward Side-Chain Dealkylation of Sterols</title><author>Lorenzo, Manuel ; Cueto, Mercedes ; D'Croz, Luis ; Maté, Juan L. ; San-Martín, Aurelio ; Darias, José</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3275-b991c47ddd1f7ed755ad2ffdda645da8a8748bd48e469ef4e5dba02ab13d44ba3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>24-Epoxisterol</topic><topic>Biogenesis</topic><topic>Muricea spp</topic><topic>Non-zooxanthellate gorgonia</topic><topic>Octocoral</topic><topic>Pregnanes</topic><topic>Side-chain dealkylation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lorenzo, Manuel</creatorcontrib><creatorcontrib>Cueto, Mercedes</creatorcontrib><creatorcontrib>D'Croz, Luis</creatorcontrib><creatorcontrib>Maté, Juan L.</creatorcontrib><creatorcontrib>San-Martín, Aurelio</creatorcontrib><creatorcontrib>Darias, José</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>European Journal of Organic Chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lorenzo, Manuel</au><au>Cueto, Mercedes</au><au>D'Croz, Luis</au><au>Maté, Juan L.</au><au>San-Martín, Aurelio</au><au>Darias, José</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Muriceanol, a 24(28)-Epoxide Sterol Link in the Carbon Flux Toward Side-Chain Dealkylation of Sterols</atitle><jtitle>European Journal of Organic Chemistry</jtitle><addtitle>Eur. 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The (22S)‐22‐hydroxy group, after 24‐dealkylation of 1, may be an advantageous functionalization in the side‐chain cleavage to C‐21‐pregnane steroids in Muricea spp. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.200500775</doi><tpages>4</tpages></addata></record> |
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| subjects | 24-Epoxisterol Biogenesis Muricea spp Non-zooxanthellate gorgonia Octocoral Pregnanes Side-chain dealkylation |
| title | Muriceanol, a 24(28)-Epoxide Sterol Link in the Carbon Flux Toward Side-Chain Dealkylation of Sterols |
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