Enantioselective Dehydroxylation of Enterodiol and Enterolactone Precursors by Human Intestinal Bacteria
During the course of experiments on the transformation of lignans to phytoestrogenic substances, such as enterodiol (END) and enterolactone (ENL), a previously isolated bacterium, Eubacterium (E.) sp. strain SDG-2, capable of phenolic p-dehydroxylation in the biotransformation of secoisolariciresino...
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| Veröffentlicht in: | Biological & Pharmaceutical Bulletin 2007/11/01, Vol.30(11), pp.2113-2119 |
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| creator | Jin, Jong-Sik Zhao, Yu-Feng Nakamura, Norio Akao, Teruaki Kakiuchi, Nobuko Min, Byung-Sun Hattori, Masao |
| description | During the course of experiments on the transformation of lignans to phytoestrogenic substances, such as enterodiol (END) and enterolactone (ENL), a previously isolated bacterium, Eubacterium (E.) sp. strain SDG-2, capable of phenolic p-dehydroxylation in the biotransformation of secoisolariciresinol diglucoside to END and ENL, was concluded to be Eggerthella (Eg.) lenta (Eg. sp. SDG-2) on the basis of 16S rRNA gene sequence analysis. The bacterium could transform (+)-dihydroxyenterodiol (DHEND, 3a) to (+)-END (1a), but not for (−)-DHEND (3b) to (−)-END (1b) under anaerobic conditions. By incubation of a mixture of (+)- and (−)-dihydroxyenterolactone (DHENL, 4a and 4b) with Eg. sp. SDG-2, only (−)-DHENL (4b) was converted to (−)-ENL (2b), selectively. On the other hand, we isolated a different bacterium, strain ARC-1, capable of dehydroxylating (−)-DHEND (3b) to (−)-END (1b) from human feces. Strain ARC-1 could transform not only (−)-DHEND (3b) to (−)-END (1b), but also (+)-DHENL (4a) to (+)-ENL (2b). However, the bacterium could not transform (+)-DHEND (3a) and (−)-DHENL (4b). Both bacterial strains demonstrated different enantioselective dehydroxylation. |
| doi_str_mv | 10.1248/bpb.30.2113 |
| format | Article |
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SDG-2) on the basis of 16S rRNA gene sequence analysis. The bacterium could transform (+)-dihydroxyenterodiol (DHEND, 3a) to (+)-END (1a), but not for (−)-DHEND (3b) to (−)-END (1b) under anaerobic conditions. By incubation of a mixture of (+)- and (−)-dihydroxyenterolactone (DHENL, 4a and 4b) with Eg. sp. SDG-2, only (−)-DHENL (4b) was converted to (−)-ENL (2b), selectively. On the other hand, we isolated a different bacterium, strain ARC-1, capable of dehydroxylating (−)-DHEND (3b) to (−)-END (1b) from human feces. Strain ARC-1 could transform not only (−)-DHEND (3b) to (−)-END (1b), but also (+)-DHENL (4a) to (+)-ENL (2b). However, the bacterium could not transform (+)-DHEND (3a) and (−)-DHENL (4b). Both bacterial strains demonstrated different enantioselective dehydroxylation.</description><identifier>ISSN: 0918-6158</identifier><identifier>EISSN: 1347-5215</identifier><identifier>DOI: 10.1248/bpb.30.2113</identifier><identifier>PMID: 17978485</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>4-Butyrolactone - analogs & derivatives ; 4-Butyrolactone - chemistry ; 4-Butyrolactone - metabolism ; Bacteria, Anaerobic - genetics ; Bacteria, Anaerobic - isolation & purification ; Bacteria, Anaerobic - metabolism ; Biotransformation ; Butylene Glycols - chemistry ; Butylene Glycols - metabolism ; dehydroxylation ; enantioselectivity ; Eubacterium ; Eubacterium - genetics ; Eubacterium - isolation & purification ; Eubacterium - metabolism ; Feces - microbiology ; Glucosides - chemistry ; Glucosides - metabolism ; human intestinal bacteria ; Humans ; Hydroxylation ; Intestines - microbiology ; lignan ; Lignans - chemistry ; Lignans - metabolism ; Molecular Structure ; Phylogeny ; RNA, Bacterial - genetics ; RNA, Ribosomal, 16S - genetics ; Stereoisomerism</subject><ispartof>Biological and Pharmaceutical Bulletin, 2007/11/01, Vol.30(11), pp.2113-2119</ispartof><rights>2007 The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 2007</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c721t-9747b6cd7df76ad624de0a845447141a3e369210ba418c4c891e35f468b3d0353</citedby><cites>FETCH-LOGICAL-c721t-9747b6cd7df76ad624de0a845447141a3e369210ba418c4c891e35f468b3d0353</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1877,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17978485$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Jin, Jong-Sik</creatorcontrib><creatorcontrib>Zhao, Yu-Feng</creatorcontrib><creatorcontrib>Nakamura, Norio</creatorcontrib><creatorcontrib>Akao, Teruaki</creatorcontrib><creatorcontrib>Kakiuchi, Nobuko</creatorcontrib><creatorcontrib>Min, Byung-Sun</creatorcontrib><creatorcontrib>Hattori, Masao</creatorcontrib><creatorcontrib>Kanazawa University</creatorcontrib><creatorcontrib>aInstitute of Natural Medicine</creatorcontrib><creatorcontrib>cFaculty of Pharmaceutical Sciences</creatorcontrib><creatorcontrib>dGraduate School of Natural Science and Technology</creatorcontrib><creatorcontrib>Catholic University of Daegue</creatorcontrib><creatorcontrib>eCollege of Phannacy</creatorcontrib><creatorcontrib>University of Toyama</creatorcontrib><creatorcontrib>bFaculty of Pharnwaceutical Sciences</creatorcontrib><creatorcontrib>Doshisha Women's College of Liberal Arts</creatorcontrib><title>Enantioselective Dehydroxylation of Enterodiol and Enterolactone Precursors by Human Intestinal Bacteria</title><title>Biological & Pharmaceutical Bulletin</title><addtitle>Biol Pharm Bull</addtitle><description>During the course of experiments on the transformation of lignans to phytoestrogenic substances, such as enterodiol (END) and enterolactone (ENL), a previously isolated bacterium, Eubacterium (E.) sp. strain SDG-2, capable of phenolic p-dehydroxylation in the biotransformation of secoisolariciresinol diglucoside to END and ENL, was concluded to be Eggerthella (Eg.) lenta (Eg. sp. SDG-2) on the basis of 16S rRNA gene sequence analysis. The bacterium could transform (+)-dihydroxyenterodiol (DHEND, 3a) to (+)-END (1a), but not for (−)-DHEND (3b) to (−)-END (1b) under anaerobic conditions. By incubation of a mixture of (+)- and (−)-dihydroxyenterolactone (DHENL, 4a and 4b) with Eg. sp. SDG-2, only (−)-DHENL (4b) was converted to (−)-ENL (2b), selectively. On the other hand, we isolated a different bacterium, strain ARC-1, capable of dehydroxylating (−)-DHEND (3b) to (−)-END (1b) from human feces. Strain ARC-1 could transform not only (−)-DHEND (3b) to (−)-END (1b), but also (+)-DHENL (4a) to (+)-ENL (2b). However, the bacterium could not transform (+)-DHEND (3a) and (−)-DHENL (4b). Both bacterial strains demonstrated different enantioselective dehydroxylation.</description><subject>4-Butyrolactone - analogs & derivatives</subject><subject>4-Butyrolactone - chemistry</subject><subject>4-Butyrolactone - metabolism</subject><subject>Bacteria, Anaerobic - genetics</subject><subject>Bacteria, Anaerobic - isolation & purification</subject><subject>Bacteria, Anaerobic - metabolism</subject><subject>Biotransformation</subject><subject>Butylene Glycols - chemistry</subject><subject>Butylene Glycols - metabolism</subject><subject>dehydroxylation</subject><subject>enantioselectivity</subject><subject>Eubacterium</subject><subject>Eubacterium - genetics</subject><subject>Eubacterium - isolation & purification</subject><subject>Eubacterium - metabolism</subject><subject>Feces - microbiology</subject><subject>Glucosides - chemistry</subject><subject>Glucosides - metabolism</subject><subject>human intestinal bacteria</subject><subject>Humans</subject><subject>Hydroxylation</subject><subject>Intestines - microbiology</subject><subject>lignan</subject><subject>Lignans - chemistry</subject><subject>Lignans - metabolism</subject><subject>Molecular Structure</subject><subject>Phylogeny</subject><subject>RNA, Bacterial - genetics</subject><subject>RNA, Ribosomal, 16S - genetics</subject><subject>Stereoisomerism</subject><issn>0918-6158</issn><issn>1347-5215</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc1vEzEQxS0EoqFw4o5WQuJSbfDYXn8caZvSSpXgAGfL63WII8cO9i4i_z1ON6USFy5j2fObN896CL0FvATC5Md-3y8pXhIA-gwtgDLRdgS652iBFciWQyfP0KtSthhjgQl9ic5AKCGZ7BZos4omjj4VF5wd_S_XXLvNYcjp9yGY-h6btG5WcXQ5DT6FxsThdA3Gjim65mt2dsol5dL0h-Z22pnY3FWijD6a0FxWzGVvXqMXaxOKe3M6z9H3m9W3q9v2_svnu6tP960VBMZWCSZ6bgcxrAU3AydscNhI1jEmgIGhjnJFAPeGgbTMSgWOdmvGZU8HTDt6jj7Muvucfk7Vhd75Yl0IJro0Fc0l44QT-C8ISknFBK_g-3_AbZpy_VtlGFOU047jSl3MlM2plOzWep_9zuSDBqyPOemak6ZYH3Oq9LuT5tTv3PDEnoKpwM0M1K63JqQYfHRPm20Rfc0jaVJD1RhTDKAxmeWPRTFK4cH95Sy0LaP54f5uMnn0NrhHV3V6rg_zj027MVm7SP8AkSi7iQ</recordid><startdate>20071101</startdate><enddate>20071101</enddate><creator>Jin, Jong-Sik</creator><creator>Zhao, Yu-Feng</creator><creator>Nakamura, Norio</creator><creator>Akao, Teruaki</creator><creator>Kakiuchi, Nobuko</creator><creator>Min, Byung-Sun</creator><creator>Hattori, Masao</creator><general>The Pharmaceutical Society of Japan</general><general>Pharmaceutical Society of Japan</general><general>Japan Science and Technology Agency</general><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>7QP</scope><scope>7QR</scope><scope>7TK</scope><scope>7U9</scope><scope>8FD</scope><scope>FR3</scope><scope>H94</scope><scope>P64</scope><scope>7QL</scope><scope>7T7</scope><scope>C1K</scope><scope>7X8</scope></search><sort><creationdate>20071101</creationdate><title>Enantioselective Dehydroxylation of Enterodiol and Enterolactone Precursors by Human Intestinal Bacteria</title><author>Jin, Jong-Sik ; Zhao, Yu-Feng ; Nakamura, Norio ; Akao, Teruaki ; Kakiuchi, Nobuko ; Min, Byung-Sun ; Hattori, Masao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c721t-9747b6cd7df76ad624de0a845447141a3e369210ba418c4c891e35f468b3d0353</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>4-Butyrolactone - 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SDG-2) on the basis of 16S rRNA gene sequence analysis. The bacterium could transform (+)-dihydroxyenterodiol (DHEND, 3a) to (+)-END (1a), but not for (−)-DHEND (3b) to (−)-END (1b) under anaerobic conditions. By incubation of a mixture of (+)- and (−)-dihydroxyenterolactone (DHENL, 4a and 4b) with Eg. sp. SDG-2, only (−)-DHENL (4b) was converted to (−)-ENL (2b), selectively. On the other hand, we isolated a different bacterium, strain ARC-1, capable of dehydroxylating (−)-DHEND (3b) to (−)-END (1b) from human feces. Strain ARC-1 could transform not only (−)-DHEND (3b) to (−)-END (1b), but also (+)-DHENL (4a) to (+)-ENL (2b). However, the bacterium could not transform (+)-DHEND (3a) and (−)-DHENL (4b). Both bacterial strains demonstrated different enantioselective dehydroxylation.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>17978485</pmid><doi>10.1248/bpb.30.2113</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | 4-Butyrolactone - analogs & derivatives 4-Butyrolactone - chemistry 4-Butyrolactone - metabolism Bacteria, Anaerobic - genetics Bacteria, Anaerobic - isolation & purification Bacteria, Anaerobic - metabolism Biotransformation Butylene Glycols - chemistry Butylene Glycols - metabolism dehydroxylation enantioselectivity Eubacterium Eubacterium - genetics Eubacterium - isolation & purification Eubacterium - metabolism Feces - microbiology Glucosides - chemistry Glucosides - metabolism human intestinal bacteria Humans Hydroxylation Intestines - microbiology lignan Lignans - chemistry Lignans - metabolism Molecular Structure Phylogeny RNA, Bacterial - genetics RNA, Ribosomal, 16S - genetics Stereoisomerism |
| title | Enantioselective Dehydroxylation of Enterodiol and Enterolactone Precursors by Human Intestinal Bacteria |
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