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Halistanol sulfates I and J, new SIRT1–3 inhibitory steroid sulfates from a marine sponge of the genus Halichondria
Two new analogs of halistanol sulfate ( 1 ) were isolated from a marine sponge Halichondria sp. collected at Hachijo-jima Island. Structures of these new halistanol sulfates I ( 2 ) and J ( 3 ) were elucidated by spectral analyses. Compounds 1 – 3 showed inhibitory activity against SIRT 1-3 with IC...
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| Published in: | Journal of antibiotics 2018-02, Vol.71 (2), p.273-278 |
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| Main Authors: | , , , , , , , , , , , |
| Format: | Article |
| Language: | English |
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| cites | cdi_FETCH-LOGICAL-c485t-96c476182610f9bd3dfde172600daf51e07c1ebfd5e5701af9f4fc491e5dc5673 |
| container_end_page | 278 |
| container_issue | 2 |
| container_start_page | 273 |
| container_title | Journal of antibiotics |
| container_volume | 71 |
| creator | Nakamura, Fumiaki Kudo, Norio Tomachi, Yuki Nakata, Akiko Takemoto, Misao Ito, Akihiro Tabei, Hodaka Arai, Daisuke de Voogd, Nicole Yoshida, Minoru Nakao, Yoichi Fusetani, Nobuhiro |
| description | Two new analogs of halistanol sulfate (
1
) were isolated from a marine sponge
Halichondria
sp. collected at Hachijo-jima Island. Structures of these new halistanol sulfates I (
2
) and J (
3
) were elucidated by spectral analyses. Compounds
1
–
3
showed inhibitory activity against SIRT 1-3 with IC
50
ranges of 45.9–67.9, 18.9–21.1 and 21.8-37.5 μ
M
, respectively. X-ray crystallography of the halistanol sulfate (
1
) and SIRT3 complex clearly indicates that
1
binds to the exosite of SIRT3 that we have discovered in this study. |
| doi_str_mv | 10.1038/ja.2017.145 |
| format | article |
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1
) were isolated from a marine sponge
Halichondria
sp. collected at Hachijo-jima Island. Structures of these new halistanol sulfates I (
2
) and J (
3
) were elucidated by spectral analyses. Compounds
1
–
3
showed inhibitory activity against SIRT 1-3 with IC
50
ranges of 45.9–67.9, 18.9–21.1 and 21.8-37.5 μ
M
, respectively. X-ray crystallography of the halistanol sulfate (
1
) and SIRT3 complex clearly indicates that
1
binds to the exosite of SIRT3 that we have discovered in this study.</description><identifier>ISSN: 0021-8820</identifier><identifier>EISSN: 1881-1469</identifier><identifier>DOI: 10.1038/ja.2017.145</identifier><identifier>PMID: 29184120</identifier><language>eng</language><publisher>London: Nature Publishing Group UK</publisher><subject><![CDATA[631/154/309/556 ; 631/535/1266 ; 631/92/349 ; 82/16 ; 82/58 ; Animals ; Antibiotics ; Antineoplastic Agents - isolation & purification ; Antineoplastic Agents - pharmacology ; Bacteriology ; Biochemistry ; Biomedical and Life Sciences ; Bioorganic Chemistry ; Crystallography ; Crystallography, X-Ray ; Drug Screening Assays, Antitumor ; Halichondria ; HeLa Cells ; Humans ; Life Sciences ; Magnetic Resonance Spectroscopy ; Medicinal Chemistry ; Microbiology ; Models, Molecular ; Molecular Structure ; Organic Chemistry ; original-article ; Porifera - chemistry ; SIRT1 protein ; Sirtuin 1 - antagonists & inhibitors ; Sirtuin 2 - antagonists & inhibitors ; Sirtuin 3 - antagonists & inhibitors ; Sirtuins - antagonists & inhibitors ; Spectrometry, Mass, Electrospray Ionization ; Spectrophotometry, Ultraviolet ; Steroids ; Sterols - isolation & purification ; Sterols - pharmacology ; Sulfates ; X-ray crystallography]]></subject><ispartof>Journal of antibiotics, 2018-02, Vol.71 (2), p.273-278</ispartof><rights>Japan Antibiotics Research Association 2018</rights><rights>Copyright Nature Publishing Group Feb 2018</rights><rights>Japan Antibiotics Research Association 2018.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c485t-96c476182610f9bd3dfde172600daf51e07c1ebfd5e5701af9f4fc491e5dc5673</citedby><cites>FETCH-LOGICAL-c485t-96c476182610f9bd3dfde172600daf51e07c1ebfd5e5701af9f4fc491e5dc5673</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27900,27901</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29184120$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nakamura, Fumiaki</creatorcontrib><creatorcontrib>Kudo, Norio</creatorcontrib><creatorcontrib>Tomachi, Yuki</creatorcontrib><creatorcontrib>Nakata, Akiko</creatorcontrib><creatorcontrib>Takemoto, Misao</creatorcontrib><creatorcontrib>Ito, Akihiro</creatorcontrib><creatorcontrib>Tabei, Hodaka</creatorcontrib><creatorcontrib>Arai, Daisuke</creatorcontrib><creatorcontrib>de Voogd, Nicole</creatorcontrib><creatorcontrib>Yoshida, Minoru</creatorcontrib><creatorcontrib>Nakao, Yoichi</creatorcontrib><creatorcontrib>Fusetani, Nobuhiro</creatorcontrib><title>Halistanol sulfates I and J, new SIRT1–3 inhibitory steroid sulfates from a marine sponge of the genus Halichondria</title><title>Journal of antibiotics</title><addtitle>J Antibiot</addtitle><addtitle>J Antibiot (Tokyo)</addtitle><description>Two new analogs of halistanol sulfate (
1
) were isolated from a marine sponge
Halichondria
sp. collected at Hachijo-jima Island. Structures of these new halistanol sulfates I (
2
) and J (
3
) were elucidated by spectral analyses. Compounds
1
–
3
showed inhibitory activity against SIRT 1-3 with IC
50
ranges of 45.9–67.9, 18.9–21.1 and 21.8-37.5 μ
M
, respectively. X-ray crystallography of the halistanol sulfate (
1
) and SIRT3 complex clearly indicates that
1
binds to the exosite of SIRT3 that we have discovered in this study.</description><subject>631/154/309/556</subject><subject>631/535/1266</subject><subject>631/92/349</subject><subject>82/16</subject><subject>82/58</subject><subject>Animals</subject><subject>Antibiotics</subject><subject>Antineoplastic Agents - isolation & purification</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Bacteriology</subject><subject>Biochemistry</subject><subject>Biomedical and Life Sciences</subject><subject>Bioorganic Chemistry</subject><subject>Crystallography</subject><subject>Crystallography, X-Ray</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Halichondria</subject><subject>HeLa Cells</subject><subject>Humans</subject><subject>Life Sciences</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medicinal Chemistry</subject><subject>Microbiology</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>Organic Chemistry</subject><subject>original-article</subject><subject>Porifera - chemistry</subject><subject>SIRT1 protein</subject><subject>Sirtuin 1 - antagonists & inhibitors</subject><subject>Sirtuin 2 - antagonists & inhibitors</subject><subject>Sirtuin 3 - antagonists & inhibitors</subject><subject>Sirtuins - antagonists & inhibitors</subject><subject>Spectrometry, Mass, Electrospray Ionization</subject><subject>Spectrophotometry, Ultraviolet</subject><subject>Steroids</subject><subject>Sterols - isolation & purification</subject><subject>Sterols - pharmacology</subject><subject>Sulfates</subject><subject>X-ray crystallography</subject><issn>0021-8820</issn><issn>1881-1469</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNp90c2KFDEUBeAgitOOrtxLwI3gVHtvKqkky2FQp2VA0HEd0pVkuprqpE2qkNn5Dr6hT2KaHn8QcZVFvpwb7iHkKcISoVWvtnbJAOUSubhHFqgUNsg7fZ8sABg2SjE4IY9K2QK0spXqITlhGhVHBgsyX9pxKJONaaRlHoOdfKEraqOj785o9F_ox9WHa_z-9VtLh7gZ1sOU8i0tk89pcL-fhJx21NKdzUP0tOxTvPE0BTptPL3xcS70MKjfpOjyYB-TB8GOxT-5O0_Jpzevry8um6v3b1cX51dNz5WYGt31XHaoWIcQ9Nq1LjiPknUAzgaBHmSPfh2c8EIC2qADDz3X6IXrRSfbU_LimLvP6fPsy2R2Q-n9ONro01wMaglMAues0ud_0W2ac6y_M0wKLbniSv1PodaoFYLQVb08qj6nUrIPZp-Huppbg2AOnZmtNYfOTO2s6md3mfN6590v-7OkCs6OoNSrutf8x9B_5P0AAOufhg</recordid><startdate>20180201</startdate><enddate>20180201</enddate><creator>Nakamura, Fumiaki</creator><creator>Kudo, Norio</creator><creator>Tomachi, Yuki</creator><creator>Nakata, Akiko</creator><creator>Takemoto, Misao</creator><creator>Ito, Akihiro</creator><creator>Tabei, Hodaka</creator><creator>Arai, Daisuke</creator><creator>de Voogd, Nicole</creator><creator>Yoshida, Minoru</creator><creator>Nakao, Yoichi</creator><creator>Fusetani, Nobuhiro</creator><general>Nature Publishing Group UK</general><general>Nature Publishing Group</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>3V.</scope><scope>7QL</scope><scope>7T5</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>88I</scope><scope>8FE</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AEUYN</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BHPHI</scope><scope>C1K</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>H94</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>LK8</scope><scope>M0S</scope><scope>M1P</scope><scope>M2P</scope><scope>M7P</scope><scope>PHGZM</scope><scope>PHGZT</scope><scope>PJZUB</scope><scope>PKEHL</scope><scope>PPXIY</scope><scope>PQEST</scope><scope>PQGLB</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>Q9U</scope><scope>7X8</scope></search><sort><creationdate>20180201</creationdate><title>Halistanol sulfates I and J, new SIRT1–3 inhibitory steroid sulfates from a marine sponge of the genus Halichondria</title><author>Nakamura, Fumiaki ; Kudo, Norio ; Tomachi, Yuki ; Nakata, Akiko ; Takemoto, Misao ; Ito, Akihiro ; Tabei, Hodaka ; Arai, Daisuke ; de Voogd, Nicole ; Yoshida, Minoru ; Nakao, Yoichi ; Fusetani, Nobuhiro</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c485t-96c476182610f9bd3dfde172600daf51e07c1ebfd5e5701af9f4fc491e5dc5673</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>631/154/309/556</topic><topic>631/535/1266</topic><topic>631/92/349</topic><topic>82/16</topic><topic>82/58</topic><topic>Animals</topic><topic>Antibiotics</topic><topic>Antineoplastic Agents - 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Academic</collection><jtitle>Journal of antibiotics</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nakamura, Fumiaki</au><au>Kudo, Norio</au><au>Tomachi, Yuki</au><au>Nakata, Akiko</au><au>Takemoto, Misao</au><au>Ito, Akihiro</au><au>Tabei, Hodaka</au><au>Arai, Daisuke</au><au>de Voogd, Nicole</au><au>Yoshida, Minoru</au><au>Nakao, Yoichi</au><au>Fusetani, Nobuhiro</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Halistanol sulfates I and J, new SIRT1–3 inhibitory steroid sulfates from a marine sponge of the genus Halichondria</atitle><jtitle>Journal of antibiotics</jtitle><stitle>J Antibiot</stitle><addtitle>J Antibiot (Tokyo)</addtitle><date>2018-02-01</date><risdate>2018</risdate><volume>71</volume><issue>2</issue><spage>273</spage><epage>278</epage><pages>273-278</pages><issn>0021-8820</issn><eissn>1881-1469</eissn><abstract>Two new analogs of halistanol sulfate (
1
) were isolated from a marine sponge
Halichondria
sp. collected at Hachijo-jima Island. Structures of these new halistanol sulfates I (
2
) and J (
3
) were elucidated by spectral analyses. Compounds
1
–
3
showed inhibitory activity against SIRT 1-3 with IC
50
ranges of 45.9–67.9, 18.9–21.1 and 21.8-37.5 μ
M
, respectively. X-ray crystallography of the halistanol sulfate (
1
) and SIRT3 complex clearly indicates that
1
binds to the exosite of SIRT3 that we have discovered in this study.</abstract><cop>London</cop><pub>Nature Publishing Group UK</pub><pmid>29184120</pmid><doi>10.1038/ja.2017.145</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0021-8820 |
| ispartof | Journal of antibiotics, 2018-02, Vol.71 (2), p.273-278 |
| issn | 0021-8820 1881-1469 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1970270442 |
| source | Springer Nature |
| subjects | 631/154/309/556 631/535/1266 631/92/349 82/16 82/58 Animals Antibiotics Antineoplastic Agents - isolation & purification Antineoplastic Agents - pharmacology Bacteriology Biochemistry Biomedical and Life Sciences Bioorganic Chemistry Crystallography Crystallography, X-Ray Drug Screening Assays, Antitumor Halichondria HeLa Cells Humans Life Sciences Magnetic Resonance Spectroscopy Medicinal Chemistry Microbiology Models, Molecular Molecular Structure Organic Chemistry original-article Porifera - chemistry SIRT1 protein Sirtuin 1 - antagonists & inhibitors Sirtuin 2 - antagonists & inhibitors Sirtuin 3 - antagonists & inhibitors Sirtuins - antagonists & inhibitors Spectrometry, Mass, Electrospray Ionization Spectrophotometry, Ultraviolet Steroids Sterols - isolation & purification Sterols - pharmacology Sulfates X-ray crystallography |
| title | Halistanol sulfates I and J, new SIRT1–3 inhibitory steroid sulfates from a marine sponge of the genus Halichondria |
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