A New Lignan (Polonilignan) and Inhibitors of Nitric Oxide Production from Penicillium polonicum, an Endophytic Fungi of Piper nigrum
Inhibiting nitric oxide (NO) or its production is found to be of therapeutic benefit. To discover natural small molecule inhibitors of NO production, a bioassay‐ and LC/MS‐guided chemical investigation was done on the metabolites of endophytic fungus isolated from fresh Piper nigrum fruits. The isol...
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| Veröffentlicht in: | Chemistry & biodiversity 2023-03, Vol.20 (3), p.e202200840-n/a |
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| creator | Pal, Pragya Paramita Begum, Sajeli A. Basha, Ameer S. Araya, Hiroshi Fujimoto, Yoshinori |
| description | Inhibiting nitric oxide (NO) or its production is found to be of therapeutic benefit. To discover natural small molecule inhibitors of NO production, a bioassay‐ and LC/MS‐guided chemical investigation was done on the metabolites of endophytic fungus isolated from fresh Piper nigrum fruits. The isolated pure strain was identified as Penicillium polonicum by 16S rDNA sequence comparison. The culture broth extract of P. polonicum (EEPP) exhibited a significant reduction of NO production (Griess method) in LPS‐stimulated RAW 264.7 cells (P |
| doi_str_mv | 10.1002/cbdv.202200840 |
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To discover natural small molecule inhibitors of NO production, a bioassay‐ and LC/MS‐guided chemical investigation was done on the metabolites of endophytic fungus isolated from fresh Piper nigrum fruits. The isolated pure strain was identified as Penicillium polonicum by 16S rDNA sequence comparison. The culture broth extract of P. polonicum (EEPP) exhibited a significant reduction of NO production (Griess method) in LPS‐stimulated RAW 264.7 cells (P<0.0001). To understand the chemical constituents of bioactive EEPP, column chromatography and p‐TLC studies were carried out, which yielded eight pure compounds. They were characterised as botryosphaeridione (1), 3‐(3,5‐di‐tert‐butyl‐4‐hydroxy)phenylpropionic acid (2), variabilone (3), 2,4‐di‐tert‐butylphenol (4), indole‐3‐carboxylic acid (5), tyrosol (6), ethyl ferulate (7) and a new lignan (8) based on the spectral analysis. The structure elucidation of the new lignan, named polonilignan (8), was based on HR‐MS, 1H‐ & 13C‐NMR, H−H COSY, HSQC and HMBC spectra. Compounds 2, 4, 5 and 6 showed a significant decrease (P<0.0001) in the production of NO in LPS‐induced RAW 264.7 cells. Tyrosol (6) and indole‐3‐carboxylic acid (5) controlled nitrite release with IC50 values of 22.84 and 55.01 μM, respectively. This is the first report of (i) P. polonicum as an endophytic fungus of pepper fruits, (ii) isolation of compounds 1–8 except 6 from P. polonicum culture broth extract and (iii) NO inhibition effect of 2, 4, 5 and 6.</description><identifier>ISSN: 1612-1872</identifier><identifier>EISSN: 1612-1880</identifier><identifier>DOI: 10.1002/cbdv.202200840</identifier><identifier>PMID: 36662670</identifier><language>eng</language><publisher>Switzerland: Wiley Subscription Services, Inc</publisher><subject>Bioassays ; Carboxylic acids ; Cell culture ; Column chromatography ; Endophytes ; endophytic fungi ; Fruits ; Fungi ; Inhibitors ; Lignans ; Lignans - metabolism ; Lignans - pharmacology ; lignin ; Lipopolysaccharides ; Lipopolysaccharides - pharmacology ; Metabolites ; Nitric oxide ; Nitric Oxide - metabolism ; nitric oxide inhibition ; NMR ; Nuclear magnetic resonance ; Penicillium ; Penicillium - chemistry ; Penicillium polonicum ; Peridinium polonicum ; Piper nigrum ; Plant Extracts - metabolism ; polonilignan ; rRNA 16S ; Spectral analysis ; Spectrum analysis ; Tyrosol</subject><ispartof>Chemistry & biodiversity, 2023-03, Vol.20 (3), p.e202200840-n/a</ispartof><rights>2023 Wiley‐VHCA AG, Zurich, Switzerland</rights><rights>2023 Wiley-VHCA AG, Zurich, Switzerland.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3730-25f319b34afa4213d08ff162db040534ca5429a80fbe7467e7b9d8a821b444023</citedby><cites>FETCH-LOGICAL-c3730-25f319b34afa4213d08ff162db040534ca5429a80fbe7467e7b9d8a821b444023</cites><orcidid>0000-0002-1673-8873</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcbdv.202200840$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcbdv.202200840$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36662670$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Pal, Pragya Paramita</creatorcontrib><creatorcontrib>Begum, Sajeli A.</creatorcontrib><creatorcontrib>Basha, Ameer S.</creatorcontrib><creatorcontrib>Araya, Hiroshi</creatorcontrib><creatorcontrib>Fujimoto, Yoshinori</creatorcontrib><title>A New Lignan (Polonilignan) and Inhibitors of Nitric Oxide Production from Penicillium polonicum, an Endophytic Fungi of Piper nigrum</title><title>Chemistry & biodiversity</title><addtitle>Chem Biodivers</addtitle><description>Inhibiting nitric oxide (NO) or its production is found to be of therapeutic benefit. To discover natural small molecule inhibitors of NO production, a bioassay‐ and LC/MS‐guided chemical investigation was done on the metabolites of endophytic fungus isolated from fresh Piper nigrum fruits. The isolated pure strain was identified as Penicillium polonicum by 16S rDNA sequence comparison. The culture broth extract of P. polonicum (EEPP) exhibited a significant reduction of NO production (Griess method) in LPS‐stimulated RAW 264.7 cells (P<0.0001). To understand the chemical constituents of bioactive EEPP, column chromatography and p‐TLC studies were carried out, which yielded eight pure compounds. They were characterised as botryosphaeridione (1), 3‐(3,5‐di‐tert‐butyl‐4‐hydroxy)phenylpropionic acid (2), variabilone (3), 2,4‐di‐tert‐butylphenol (4), indole‐3‐carboxylic acid (5), tyrosol (6), ethyl ferulate (7) and a new lignan (8) based on the spectral analysis. The structure elucidation of the new lignan, named polonilignan (8), was based on HR‐MS, 1H‐ & 13C‐NMR, H−H COSY, HSQC and HMBC spectra. Compounds 2, 4, 5 and 6 showed a significant decrease (P<0.0001) in the production of NO in LPS‐induced RAW 264.7 cells. Tyrosol (6) and indole‐3‐carboxylic acid (5) controlled nitrite release with IC50 values of 22.84 and 55.01 μM, respectively. This is the first report of (i) P. polonicum as an endophytic fungus of pepper fruits, (ii) isolation of compounds 1–8 except 6 from P. polonicum culture broth extract and (iii) NO inhibition effect of 2, 4, 5 and 6.</description><subject>Bioassays</subject><subject>Carboxylic acids</subject><subject>Cell culture</subject><subject>Column chromatography</subject><subject>Endophytes</subject><subject>endophytic fungi</subject><subject>Fruits</subject><subject>Fungi</subject><subject>Inhibitors</subject><subject>Lignans</subject><subject>Lignans - metabolism</subject><subject>Lignans - pharmacology</subject><subject>lignin</subject><subject>Lipopolysaccharides</subject><subject>Lipopolysaccharides - pharmacology</subject><subject>Metabolites</subject><subject>Nitric oxide</subject><subject>Nitric Oxide - metabolism</subject><subject>nitric oxide inhibition</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Penicillium</subject><subject>Penicillium - chemistry</subject><subject>Penicillium polonicum</subject><subject>Peridinium polonicum</subject><subject>Piper nigrum</subject><subject>Plant Extracts - metabolism</subject><subject>polonilignan</subject><subject>rRNA 16S</subject><subject>Spectral analysis</subject><subject>Spectrum analysis</subject><subject>Tyrosol</subject><issn>1612-1872</issn><issn>1612-1880</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkUtP3DAURi0EAkq7ZYkssaFSZ-pXEmdJp1CQRjAL6DZy_BiMEjvYcen8gP7vehgYpG66ug-de3SlD4BjjKYYIfJVturXlCBCEOIM7YBDXGIywZyj3W1fkQPwIcbHzOc93wcHtCxLUlboEPw5hzf6Gc7t0gkHzxa-8852L9NnKJyC1-7Btnb0IUJv4I0dg5Xw9rdVGi6CV0mO1jtogu_hQjsrbdfZ1MPhRSRT_yVb4IVTfnhYjfn0MrmlXasWdtABOrsMqf8I9ozoov70Wo_A_eXF3exqMr_9cT07n08krSiakMJQXLeUCSMYwVQhbgwuiWoRQwVlUhSM1IIj0-qKlZWu2lpxwQluGWOI0CNwtvEOwT8lHcemt1HqrhNO-xQbUpWc0IKwKqOn_6CPPgWXv8sUr4sCcYozNd1QMvgYgzbNEGwvwqrBqFkH1KwDarYB5YOTV21qe622-FsiGag3wLPt9Oo_umb27fvPd_lfSVqb_w</recordid><startdate>202303</startdate><enddate>202303</enddate><creator>Pal, Pragya Paramita</creator><creator>Begum, Sajeli A.</creator><creator>Basha, Ameer S.</creator><creator>Araya, Hiroshi</creator><creator>Fujimoto, Yoshinori</creator><general>Wiley Subscription Services, Inc</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>7QO</scope><scope>7TM</scope><scope>8FD</scope><scope>FR3</scope><scope>K9.</scope><scope>M7N</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-1673-8873</orcidid></search><sort><creationdate>202303</creationdate><title>A New Lignan (Polonilignan) and Inhibitors of Nitric Oxide Production from Penicillium polonicum, an Endophytic Fungi of Piper nigrum</title><author>Pal, Pragya Paramita ; Begum, Sajeli A. ; Basha, Ameer S. ; Araya, Hiroshi ; Fujimoto, Yoshinori</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3730-25f319b34afa4213d08ff162db040534ca5429a80fbe7467e7b9d8a821b444023</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Bioassays</topic><topic>Carboxylic acids</topic><topic>Cell culture</topic><topic>Column chromatography</topic><topic>Endophytes</topic><topic>endophytic fungi</topic><topic>Fruits</topic><topic>Fungi</topic><topic>Inhibitors</topic><topic>Lignans</topic><topic>Lignans - metabolism</topic><topic>Lignans - pharmacology</topic><topic>lignin</topic><topic>Lipopolysaccharides</topic><topic>Lipopolysaccharides - pharmacology</topic><topic>Metabolites</topic><topic>Nitric oxide</topic><topic>Nitric Oxide - metabolism</topic><topic>nitric oxide inhibition</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Penicillium</topic><topic>Penicillium - chemistry</topic><topic>Penicillium polonicum</topic><topic>Peridinium polonicum</topic><topic>Piper nigrum</topic><topic>Plant Extracts - metabolism</topic><topic>polonilignan</topic><topic>rRNA 16S</topic><topic>Spectral analysis</topic><topic>Spectrum analysis</topic><topic>Tyrosol</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pal, Pragya Paramita</creatorcontrib><creatorcontrib>Begum, Sajeli A.</creatorcontrib><creatorcontrib>Basha, Ameer S.</creatorcontrib><creatorcontrib>Araya, Hiroshi</creatorcontrib><creatorcontrib>Fujimoto, Yoshinori</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry & biodiversity</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pal, Pragya Paramita</au><au>Begum, Sajeli A.</au><au>Basha, Ameer S.</au><au>Araya, Hiroshi</au><au>Fujimoto, Yoshinori</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A New Lignan (Polonilignan) and Inhibitors of Nitric Oxide Production from Penicillium polonicum, an Endophytic Fungi of Piper nigrum</atitle><jtitle>Chemistry & biodiversity</jtitle><addtitle>Chem Biodivers</addtitle><date>2023-03</date><risdate>2023</risdate><volume>20</volume><issue>3</issue><spage>e202200840</spage><epage>n/a</epage><pages>e202200840-n/a</pages><issn>1612-1872</issn><eissn>1612-1880</eissn><abstract>Inhibiting nitric oxide (NO) or its production is found to be of therapeutic benefit. To discover natural small molecule inhibitors of NO production, a bioassay‐ and LC/MS‐guided chemical investigation was done on the metabolites of endophytic fungus isolated from fresh Piper nigrum fruits. The isolated pure strain was identified as Penicillium polonicum by 16S rDNA sequence comparison. The culture broth extract of P. polonicum (EEPP) exhibited a significant reduction of NO production (Griess method) in LPS‐stimulated RAW 264.7 cells (P<0.0001). To understand the chemical constituents of bioactive EEPP, column chromatography and p‐TLC studies were carried out, which yielded eight pure compounds. They were characterised as botryosphaeridione (1), 3‐(3,5‐di‐tert‐butyl‐4‐hydroxy)phenylpropionic acid (2), variabilone (3), 2,4‐di‐tert‐butylphenol (4), indole‐3‐carboxylic acid (5), tyrosol (6), ethyl ferulate (7) and a new lignan (8) based on the spectral analysis. The structure elucidation of the new lignan, named polonilignan (8), was based on HR‐MS, 1H‐ & 13C‐NMR, H−H COSY, HSQC and HMBC spectra. Compounds 2, 4, 5 and 6 showed a significant decrease (P<0.0001) in the production of NO in LPS‐induced RAW 264.7 cells. Tyrosol (6) and indole‐3‐carboxylic acid (5) controlled nitrite release with IC50 values of 22.84 and 55.01 μM, respectively. This is the first report of (i) P. polonicum as an endophytic fungus of pepper fruits, (ii) isolation of compounds 1–8 except 6 from P. polonicum culture broth extract and (iii) NO inhibition effect of 2, 4, 5 and 6.</abstract><cop>Switzerland</cop><pub>Wiley Subscription Services, Inc</pub><pmid>36662670</pmid><doi>10.1002/cbdv.202200840</doi><tpages>12</tpages><orcidid>https://orcid.org/0000-0002-1673-8873</orcidid></addata></record> |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | Bioassays Carboxylic acids Cell culture Column chromatography Endophytes endophytic fungi Fruits Fungi Inhibitors Lignans Lignans - metabolism Lignans - pharmacology lignin Lipopolysaccharides Lipopolysaccharides - pharmacology Metabolites Nitric oxide Nitric Oxide - metabolism nitric oxide inhibition NMR Nuclear magnetic resonance Penicillium Penicillium - chemistry Penicillium polonicum Peridinium polonicum Piper nigrum Plant Extracts - metabolism polonilignan rRNA 16S Spectral analysis Spectrum analysis Tyrosol |
| title | A New Lignan (Polonilignan) and Inhibitors of Nitric Oxide Production from Penicillium polonicum, an Endophytic Fungi of Piper nigrum |
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