Penicilazaphilones D and E: two new azaphilones from a sponge-derived strain of the fungus Penicillium sclerotiorum
Two new azaphilones, penicilazaphilones D ( 1 ) and E ( 2 ), along with four known analogs ( 3–6 ), were obtained from the sponge-derived fungus Penicillium sclerotiorum . Their structures were elucidated on the basis of comprehensive spectroscopic analyses, ECD calculation, single-crystal X-ray dif...
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| Veröffentlicht in: | RSC advances 2018, Vol.8 (8), p.4348-4353 |
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| container_issue | 8 |
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| container_title | RSC advances |
| container_volume | 8 |
| creator | Wang, Chao-Yi Hao, Jun-Di Ning, Xing-Yan Wu, Jing-Shuai Zhao, Dong-Lin Kong, Chui-Jian Shao, Chang-Lun Wang, Chang-Yun |
| description | Two new azaphilones, penicilazaphilones D (
1
) and E (
2
), along with four known analogs (
3–6
), were obtained from the sponge-derived fungus
Penicillium sclerotiorum
. Their structures were elucidated on the basis of comprehensive spectroscopic analyses, ECD calculation, single-crystal X-ray diffraction and comparison to the biosynthetically related compound
5
. Compound
1
represents the second reported azaphilone with a C-4 aliphatic side chain, and
2
is the first azaphilone with a tetrahydrofuran ring at C-3. Compound
3
displayed strong antiviral activity against HSV (IC
50
= 19.5 μM) and EV71 (IC
50
= 132 μM), 16 and 3 fold more potent than the positive control ribavirin, respectively. |
| doi_str_mv | 10.1039/C7RA13327H |
| format | Article |
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1
) and E (
2
), along with four known analogs (
3–6
), were obtained from the sponge-derived fungus
Penicillium sclerotiorum
. Their structures were elucidated on the basis of comprehensive spectroscopic analyses, ECD calculation, single-crystal X-ray diffraction and comparison to the biosynthetically related compound
5
. Compound
1
represents the second reported azaphilone with a C-4 aliphatic side chain, and
2
is the first azaphilone with a tetrahydrofuran ring at C-3. Compound
3
displayed strong antiviral activity against HSV (IC
50
= 19.5 μM) and EV71 (IC
50
= 132 μM), 16 and 3 fold more potent than the positive control ribavirin, respectively.</description><identifier>ISSN: 2046-2069</identifier><identifier>EISSN: 2046-2069</identifier><identifier>DOI: 10.1039/C7RA13327H</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Aliphatic compounds ; Diffraction ; Fungi ; Single crystals ; Tetrahydrofuran ; X-rays</subject><ispartof>RSC advances, 2018, Vol.8 (8), p.4348-4353</ispartof><rights>Copyright Royal Society of Chemistry 2018</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c295t-cd5e8841eee04acf37d6c2930528d597a6152524e37af0db255bc0ffe82d89d13</citedby><cites>FETCH-LOGICAL-c295t-cd5e8841eee04acf37d6c2930528d597a6152524e37af0db255bc0ffe82d89d13</cites><orcidid>0000-0002-0236-1606</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,860,4010,27900,27901,27902</link.rule.ids></links><search><creatorcontrib>Wang, Chao-Yi</creatorcontrib><creatorcontrib>Hao, Jun-Di</creatorcontrib><creatorcontrib>Ning, Xing-Yan</creatorcontrib><creatorcontrib>Wu, Jing-Shuai</creatorcontrib><creatorcontrib>Zhao, Dong-Lin</creatorcontrib><creatorcontrib>Kong, Chui-Jian</creatorcontrib><creatorcontrib>Shao, Chang-Lun</creatorcontrib><creatorcontrib>Wang, Chang-Yun</creatorcontrib><title>Penicilazaphilones D and E: two new azaphilones from a sponge-derived strain of the fungus Penicillium sclerotiorum</title><title>RSC advances</title><description>Two new azaphilones, penicilazaphilones D (
1
) and E (
2
), along with four known analogs (
3–6
), were obtained from the sponge-derived fungus
Penicillium sclerotiorum
. Their structures were elucidated on the basis of comprehensive spectroscopic analyses, ECD calculation, single-crystal X-ray diffraction and comparison to the biosynthetically related compound
5
. Compound
1
represents the second reported azaphilone with a C-4 aliphatic side chain, and
2
is the first azaphilone with a tetrahydrofuran ring at C-3. Compound
3
displayed strong antiviral activity against HSV (IC
50
= 19.5 μM) and EV71 (IC
50
= 132 μM), 16 and 3 fold more potent than the positive control ribavirin, respectively.</description><subject>Aliphatic compounds</subject><subject>Diffraction</subject><subject>Fungi</subject><subject>Single crystals</subject><subject>Tetrahydrofuran</subject><subject>X-rays</subject><issn>2046-2069</issn><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNpNUF9LwzAcDKLgmHvxEwR8E6r506Stb2NuThgoos8la37ZMtqkJq1DP72VDdy93MEdd3AIXVNyRwkv7mfZ25RyzrLlGRoxksqEEVmcn-hLNIlxRwZIQZmkIxRfwdnK1upHtVtbewcRP2LlNJ4_4G7vsYM9PjVN8A1WOLbebSDREOwXaBy7oKzD3uBuC9j0btNHfKyubd_gWNUQfGd96JsrdGFUHWFy5DH6WMzfZ8tk9fL0PJuukooVoksqLSDPUwoAJFWV4ZmWg8OJYLkWRaYkFUywFHimDNFrJsS6IsZAznReaMrH6ObQ2wb_2UPsyp3vgxsmS0YoyXMpSTGkbg-pKvgYA5iyDbZR4bukpPz7tfz_lf8C0GprhQ</recordid><startdate>2018</startdate><enddate>2018</enddate><creator>Wang, Chao-Yi</creator><creator>Hao, Jun-Di</creator><creator>Ning, Xing-Yan</creator><creator>Wu, Jing-Shuai</creator><creator>Zhao, Dong-Lin</creator><creator>Kong, Chui-Jian</creator><creator>Shao, Chang-Lun</creator><creator>Wang, Chang-Yun</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><orcidid>https://orcid.org/0000-0002-0236-1606</orcidid></search><sort><creationdate>2018</creationdate><title>Penicilazaphilones D and E: two new azaphilones from a sponge-derived strain of the fungus Penicillium sclerotiorum</title><author>Wang, Chao-Yi ; Hao, Jun-Di ; Ning, Xing-Yan ; Wu, Jing-Shuai ; Zhao, Dong-Lin ; Kong, Chui-Jian ; Shao, Chang-Lun ; Wang, Chang-Yun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c295t-cd5e8841eee04acf37d6c2930528d597a6152524e37af0db255bc0ffe82d89d13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Aliphatic compounds</topic><topic>Diffraction</topic><topic>Fungi</topic><topic>Single crystals</topic><topic>Tetrahydrofuran</topic><topic>X-rays</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Chao-Yi</creatorcontrib><creatorcontrib>Hao, Jun-Di</creatorcontrib><creatorcontrib>Ning, Xing-Yan</creatorcontrib><creatorcontrib>Wu, Jing-Shuai</creatorcontrib><creatorcontrib>Zhao, Dong-Lin</creatorcontrib><creatorcontrib>Kong, Chui-Jian</creatorcontrib><creatorcontrib>Shao, Chang-Lun</creatorcontrib><creatorcontrib>Wang, Chang-Yun</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>RSC advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Chao-Yi</au><au>Hao, Jun-Di</au><au>Ning, Xing-Yan</au><au>Wu, Jing-Shuai</au><au>Zhao, Dong-Lin</au><au>Kong, Chui-Jian</au><au>Shao, Chang-Lun</au><au>Wang, Chang-Yun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Penicilazaphilones D and E: two new azaphilones from a sponge-derived strain of the fungus Penicillium sclerotiorum</atitle><jtitle>RSC advances</jtitle><date>2018</date><risdate>2018</risdate><volume>8</volume><issue>8</issue><spage>4348</spage><epage>4353</epage><pages>4348-4353</pages><issn>2046-2069</issn><eissn>2046-2069</eissn><abstract>Two new azaphilones, penicilazaphilones D (
1
) and E (
2
), along with four known analogs (
3–6
), were obtained from the sponge-derived fungus
Penicillium sclerotiorum
. Their structures were elucidated on the basis of comprehensive spectroscopic analyses, ECD calculation, single-crystal X-ray diffraction and comparison to the biosynthetically related compound
5
. Compound
1
represents the second reported azaphilone with a C-4 aliphatic side chain, and
2
is the first azaphilone with a tetrahydrofuran ring at C-3. Compound
3
displayed strong antiviral activity against HSV (IC
50
= 19.5 μM) and EV71 (IC
50
= 132 μM), 16 and 3 fold more potent than the positive control ribavirin, respectively.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/C7RA13327H</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-0236-1606</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2046-2069 |
| ispartof | RSC advances, 2018, Vol.8 (8), p.4348-4353 |
| issn | 2046-2069 2046-2069 |
| language | eng |
| recordid | cdi_proquest_journals_2010886609 |
| source | DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central; PubMed Central Open Access |
| subjects | Aliphatic compounds Diffraction Fungi Single crystals Tetrahydrofuran X-rays |
| title | Penicilazaphilones D and E: two new azaphilones from a sponge-derived strain of the fungus Penicillium sclerotiorum |
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