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Isolation of C-29 oxygenated oleanane triterpenoids and a (+)-muurolene type sesquiterpenoid from the fruiting bodies of Fuscoporia torulosa and their bioactivities
Basidiomycetes with a wide variety of skeletons of secondary metabolites can be expected to be the source of new interesting biological compounds. During our research on basidiomycetes, two new C-29 oxygenated oleanane-type triterpenes ( 1 and 2 ) and torulosacid ( 3 ), a muurolene type sesquiterpen...
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| Published in: | Journal of natural medicines 2024-09, Vol.78 (4), p.919-928 |
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| container_title | Journal of natural medicines |
| container_volume | 78 |
| creator | Yoneyama, Tatsuro Chen, Chian Ichimura, Yoshihiro Nakashima, Katsuyuki Kenmoku, Hiromichi Imagawa, Hiroshi Umeyama, Akemi Noji, Masaaki |
| description | Basidiomycetes with a wide variety of skeletons of secondary metabolites can be expected to be the source of new interesting biological compounds. During our research on basidiomycetes, two new C-29 oxygenated oleanane-type triterpenes (
1
and
2
) and torulosacid (
3
), a muurolene type sesquiterpenoid with a five-membered ether ring along with nine known compounds (
4
–
12
), were isolated from the MeOH extract of the fruiting bodies of
Fuscoporia torulosa
. The structures of
1
–
3
were determined by NMR and HREIMS analysis. Further studies on the stereochemistry of
3
were conducted using X-ray crystallographic analysis and comparison of experimental and calculated ECD spectra. In the antimicrobial assay of isolates,
1
,
7
, and
9
showed growth inhibitory activity against methicillin-resistant
Staphylococcus aureus
and other gram-positive strains. Isolation of oleanane type triterpenes from fungi including basidiomycetes, is a unique report that could lead to further isolation of new compounds and the discovery of unique biosynthetic enzymes.
Graphical abstract |
| doi_str_mv | 10.1007/s11418-024-01832-z |
| format | article |
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1
and
2
) and torulosacid (
3
), a muurolene type sesquiterpenoid with a five-membered ether ring along with nine known compounds (
4
–
12
), were isolated from the MeOH extract of the fruiting bodies of
Fuscoporia torulosa
. The structures of
1
–
3
were determined by NMR and HREIMS analysis. Further studies on the stereochemistry of
3
were conducted using X-ray crystallographic analysis and comparison of experimental and calculated ECD spectra. In the antimicrobial assay of isolates,
1
,
7
, and
9
showed growth inhibitory activity against methicillin-resistant
Staphylococcus aureus
and other gram-positive strains. Isolation of oleanane type triterpenes from fungi including basidiomycetes, is a unique report that could lead to further isolation of new compounds and the discovery of unique biosynthetic enzymes.
Graphical abstract</description><identifier>ISSN: 1340-3443</identifier><identifier>ISSN: 1861-0293</identifier><identifier>EISSN: 1861-0293</identifier><identifier>DOI: 10.1007/s11418-024-01832-z</identifier><identifier>PMID: 39127865</identifier><language>eng</language><publisher>Singapore: Springer Nature Singapore</publisher><subject><![CDATA[Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - isolation & purification ; Anti-Bacterial Agents - pharmacology ; Antifungal agents ; Basidiomycota - chemistry ; Biomedical and Life Sciences ; Biomedicine ; Complementary & Alternative Medicine ; Crystallography, X-Ray ; Drug resistance ; Fruit bodies ; Fruiting Bodies, Fungal - chemistry ; Fuscoporia torulosa ; Medicinal Chemistry ; Methicillin ; Methicillin-Resistant Staphylococcus aureus - drug effects ; Microbial Sensitivity Tests ; Molecular Structure ; Oleanolic Acid - analogs & derivatives ; Oleanolic Acid - chemistry ; Oleanolic Acid - isolation & purification ; Oleanolic Acid - pharmacology ; Original Paper ; Pharmacology/Toxicology ; Pharmacy ; Plant Sciences ; Secondary metabolites ; Sesquiterpenes - chemistry ; Sesquiterpenes - isolation & purification ; Sesquiterpenes - pharmacology ; Stereochemistry ; Triterpenes ; Triterpenes - chemistry ; Triterpenes - isolation & purification ; Triterpenes - pharmacology ; Triterpenoids]]></subject><ispartof>Journal of natural medicines, 2024-09, Vol.78 (4), p.919-928</ispartof><rights>The Author(s) under exclusive licence to The Japanese Society of Pharmacognosy 2024. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.</rights><rights>2024. The Author(s) under exclusive licence to The Japanese Society of Pharmacognosy.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c256t-e65f4026dd0571c2b655f0f3f7cbe52326b5935b1ec3ff3d9390da0b1208fc9a3</cites><orcidid>0000-0001-7306-9015</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/39127865$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yoneyama, Tatsuro</creatorcontrib><creatorcontrib>Chen, Chian</creatorcontrib><creatorcontrib>Ichimura, Yoshihiro</creatorcontrib><creatorcontrib>Nakashima, Katsuyuki</creatorcontrib><creatorcontrib>Kenmoku, Hiromichi</creatorcontrib><creatorcontrib>Imagawa, Hiroshi</creatorcontrib><creatorcontrib>Umeyama, Akemi</creatorcontrib><creatorcontrib>Noji, Masaaki</creatorcontrib><title>Isolation of C-29 oxygenated oleanane triterpenoids and a (+)-muurolene type sesquiterpenoid from the fruiting bodies of Fuscoporia torulosa and their bioactivities</title><title>Journal of natural medicines</title><addtitle>J Nat Med</addtitle><addtitle>J Nat Med</addtitle><description>Basidiomycetes with a wide variety of skeletons of secondary metabolites can be expected to be the source of new interesting biological compounds. During our research on basidiomycetes, two new C-29 oxygenated oleanane-type triterpenes (
1
and
2
) and torulosacid (
3
), a muurolene type sesquiterpenoid with a five-membered ether ring along with nine known compounds (
4
–
12
), were isolated from the MeOH extract of the fruiting bodies of
Fuscoporia torulosa
. The structures of
1
–
3
were determined by NMR and HREIMS analysis. Further studies on the stereochemistry of
3
were conducted using X-ray crystallographic analysis and comparison of experimental and calculated ECD spectra. In the antimicrobial assay of isolates,
1
,
7
, and
9
showed growth inhibitory activity against methicillin-resistant
Staphylococcus aureus
and other gram-positive strains. Isolation of oleanane type triterpenes from fungi including basidiomycetes, is a unique report that could lead to further isolation of new compounds and the discovery of unique biosynthetic enzymes.
Graphical abstract</description><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - isolation & purification</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Antifungal agents</subject><subject>Basidiomycota - chemistry</subject><subject>Biomedical and Life Sciences</subject><subject>Biomedicine</subject><subject>Complementary & Alternative Medicine</subject><subject>Crystallography, X-Ray</subject><subject>Drug resistance</subject><subject>Fruit bodies</subject><subject>Fruiting Bodies, Fungal - chemistry</subject><subject>Fuscoporia torulosa</subject><subject>Medicinal Chemistry</subject><subject>Methicillin</subject><subject>Methicillin-Resistant Staphylococcus aureus - drug effects</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Structure</subject><subject>Oleanolic Acid - analogs & derivatives</subject><subject>Oleanolic Acid - chemistry</subject><subject>Oleanolic Acid - isolation & purification</subject><subject>Oleanolic Acid - pharmacology</subject><subject>Original Paper</subject><subject>Pharmacology/Toxicology</subject><subject>Pharmacy</subject><subject>Plant Sciences</subject><subject>Secondary metabolites</subject><subject>Sesquiterpenes - chemistry</subject><subject>Sesquiterpenes - isolation & purification</subject><subject>Sesquiterpenes - pharmacology</subject><subject>Stereochemistry</subject><subject>Triterpenes</subject><subject>Triterpenes - chemistry</subject><subject>Triterpenes - isolation & purification</subject><subject>Triterpenes - pharmacology</subject><subject>Triterpenoids</subject><issn>1340-3443</issn><issn>1861-0293</issn><issn>1861-0293</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNp9kctuFDEQRS0EIiHwAyyQJTZByOBHu6d7iUYEIkViA2vLbZcHR912xw_E5Hv4UDyZQCQWrFwqn3urVBehl4y-Y5Ru3mfGOjYQyjtC2SA4uX2ETtnQs9YaxeNWi44S0XXiBD3L-ZrSjgvBnqITMTK-GXp5in5d5jjr4mPA0eEt4SOOP_c7CLqAxXEGHXQAXJIvkFYI0duMdbBY4_O3b8hSa2rQgdivgDPkm_pAYpfigst3aEVr-7DDU7Qe8mHWRc0mrjF5jUtMdY5Z3xk33Cc8-ahN8T-aCvJz9MTpOcOL-_cMfbv4-HX7mVx9-XS5_XBFDJd9IdBL11HeW0vlhhk-9VI66oTbmAkkF7yf5CjkxMAI54QdxUitphPjdHBm1OIMnR991xRvKuSiFp8NzHM7QaxZCdruNgwdGxv6-h_0OtYU2nYHqmGS075R_EiZFHNO4NSa_KLTXjGqDhmqY4aqZajuMlS3TfTq3rpOC9i_kj-hNUAcgdy-wg7Sw-z_2P4GCWCqhQ</recordid><startdate>20240901</startdate><enddate>20240901</enddate><creator>Yoneyama, Tatsuro</creator><creator>Chen, Chian</creator><creator>Ichimura, Yoshihiro</creator><creator>Nakashima, Katsuyuki</creator><creator>Kenmoku, Hiromichi</creator><creator>Imagawa, Hiroshi</creator><creator>Umeyama, Akemi</creator><creator>Noji, Masaaki</creator><general>Springer Nature Singapore</general><general>Springer Nature B.V</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>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-7306-9015</orcidid></search><sort><creationdate>20240901</creationdate><title>Isolation of C-29 oxygenated oleanane triterpenoids and a (+)-muurolene type sesquiterpenoid from the fruiting bodies of Fuscoporia torulosa and their bioactivities</title><author>Yoneyama, Tatsuro ; Chen, Chian ; Ichimura, Yoshihiro ; Nakashima, Katsuyuki ; Kenmoku, Hiromichi ; Imagawa, Hiroshi ; Umeyama, Akemi ; Noji, Masaaki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c256t-e65f4026dd0571c2b655f0f3f7cbe52326b5935b1ec3ff3d9390da0b1208fc9a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - isolation & purification</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Antifungal agents</topic><topic>Basidiomycota - chemistry</topic><topic>Biomedical and Life Sciences</topic><topic>Biomedicine</topic><topic>Complementary & Alternative Medicine</topic><topic>Crystallography, X-Ray</topic><topic>Drug resistance</topic><topic>Fruit bodies</topic><topic>Fruiting Bodies, Fungal - chemistry</topic><topic>Fuscoporia torulosa</topic><topic>Medicinal Chemistry</topic><topic>Methicillin</topic><topic>Methicillin-Resistant Staphylococcus aureus - drug effects</topic><topic>Microbial Sensitivity Tests</topic><topic>Molecular Structure</topic><topic>Oleanolic Acid - analogs & derivatives</topic><topic>Oleanolic Acid - chemistry</topic><topic>Oleanolic Acid - isolation & purification</topic><topic>Oleanolic Acid - pharmacology</topic><topic>Original Paper</topic><topic>Pharmacology/Toxicology</topic><topic>Pharmacy</topic><topic>Plant Sciences</topic><topic>Secondary metabolites</topic><topic>Sesquiterpenes - chemistry</topic><topic>Sesquiterpenes - isolation & purification</topic><topic>Sesquiterpenes - pharmacology</topic><topic>Stereochemistry</topic><topic>Triterpenes</topic><topic>Triterpenes - chemistry</topic><topic>Triterpenes - isolation & purification</topic><topic>Triterpenes - pharmacology</topic><topic>Triterpenoids</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yoneyama, Tatsuro</creatorcontrib><creatorcontrib>Chen, Chian</creatorcontrib><creatorcontrib>Ichimura, Yoshihiro</creatorcontrib><creatorcontrib>Nakashima, Katsuyuki</creatorcontrib><creatorcontrib>Kenmoku, Hiromichi</creatorcontrib><creatorcontrib>Imagawa, Hiroshi</creatorcontrib><creatorcontrib>Umeyama, Akemi</creatorcontrib><creatorcontrib>Noji, Masaaki</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of natural medicines</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yoneyama, Tatsuro</au><au>Chen, Chian</au><au>Ichimura, Yoshihiro</au><au>Nakashima, Katsuyuki</au><au>Kenmoku, Hiromichi</au><au>Imagawa, Hiroshi</au><au>Umeyama, Akemi</au><au>Noji, Masaaki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Isolation of C-29 oxygenated oleanane triterpenoids and a (+)-muurolene type sesquiterpenoid from the fruiting bodies of Fuscoporia torulosa and their bioactivities</atitle><jtitle>Journal of natural medicines</jtitle><stitle>J Nat Med</stitle><addtitle>J Nat Med</addtitle><date>2024-09-01</date><risdate>2024</risdate><volume>78</volume><issue>4</issue><spage>919</spage><epage>928</epage><pages>919-928</pages><issn>1340-3443</issn><issn>1861-0293</issn><eissn>1861-0293</eissn><abstract>Basidiomycetes with a wide variety of skeletons of secondary metabolites can be expected to be the source of new interesting biological compounds. During our research on basidiomycetes, two new C-29 oxygenated oleanane-type triterpenes (
1
and
2
) and torulosacid (
3
), a muurolene type sesquiterpenoid with a five-membered ether ring along with nine known compounds (
4
–
12
), were isolated from the MeOH extract of the fruiting bodies of
Fuscoporia torulosa
. The structures of
1
–
3
were determined by NMR and HREIMS analysis. Further studies on the stereochemistry of
3
were conducted using X-ray crystallographic analysis and comparison of experimental and calculated ECD spectra. In the antimicrobial assay of isolates,
1
,
7
, and
9
showed growth inhibitory activity against methicillin-resistant
Staphylococcus aureus
and other gram-positive strains. Isolation of oleanane type triterpenes from fungi including basidiomycetes, is a unique report that could lead to further isolation of new compounds and the discovery of unique biosynthetic enzymes.
Graphical abstract</abstract><cop>Singapore</cop><pub>Springer Nature Singapore</pub><pmid>39127865</pmid><doi>10.1007/s11418-024-01832-z</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0001-7306-9015</orcidid></addata></record> |
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| ispartof | Journal of natural medicines, 2024-09, Vol.78 (4), p.919-928 |
| issn | 1340-3443 1861-0293 1861-0293 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_3091288419 |
| source | Springer Nature |
| subjects | Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - isolation & purification Anti-Bacterial Agents - pharmacology Antifungal agents Basidiomycota - chemistry Biomedical and Life Sciences Biomedicine Complementary & Alternative Medicine Crystallography, X-Ray Drug resistance Fruit bodies Fruiting Bodies, Fungal - chemistry Fuscoporia torulosa Medicinal Chemistry Methicillin Methicillin-Resistant Staphylococcus aureus - drug effects Microbial Sensitivity Tests Molecular Structure Oleanolic Acid - analogs & derivatives Oleanolic Acid - chemistry Oleanolic Acid - isolation & purification Oleanolic Acid - pharmacology Original Paper Pharmacology/Toxicology Pharmacy Plant Sciences Secondary metabolites Sesquiterpenes - chemistry Sesquiterpenes - isolation & purification Sesquiterpenes - pharmacology Stereochemistry Triterpenes Triterpenes - chemistry Triterpenes - isolation & purification Triterpenes - pharmacology Triterpenoids |
| title | Isolation of C-29 oxygenated oleanane triterpenoids and a (+)-muurolene type sesquiterpenoid from the fruiting bodies of Fuscoporia torulosa and their bioactivities |
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