194 lines
20 KiB
XML
194 lines
20 KiB
XML
<document id="46A5CA91D003BC87B21946EC5483FE07" ID-DOI="10.1016/j.phytochem.2020.112555" ID-ISSN="1873-3700" ID-Zenodo-Dep="8291168" IM.bibliography_approvedBy="felipe" IM.illustrations_approvedBy="juliana" IM.materialsCitations_approvedBy="felipe" IM.metadata_approvedBy="felipe" IM.tables_approvedBy="juliana" IM.taxonomicNames_approvedBy="juliana" IM.treatments_approvedBy="juliana" checkinTime="1693244706570" checkinUser="felipe" docAuthor="Isaka, Masahiko, Palasarn, Somporn, Sakayaroj, Jariya, Srichomthong, Kitlada, Nithithanasilp, Sutichai & Sappan, Malipan" docDate="2021" docId="03900A2CFF88FFF7FCBA98618D9F841C" docLanguage="en" docName="Phytochemistry.181.112555.pdf" docOrigin="Phytochemistry (112555) 181" docSource="http://dx.doi.org/10.1016/j.phytochem.2020.112555" docStyle="DocumentStyle:F36D69FC8B198FBE91029DF9C24697D3.5:Phytochemistry.2020-.journal_article" docStyleId="F36D69FC8B198FBE91029DF9C24697D3" docStyleName="Phytochemistry.2020-.journal_article" docStyleVersion="5" docTitle="Fulvifomes xylocarpicola T. Hatt, Sakayaroj & E. B. G. Jones" docType="treatment" docVersion="1" lastPageNumber="6" masterDocId="FFA97254FF8CFFF2FF889D1C8F03803F" masterDocTitle="Limonoids from fruiting bodies of the wood-rot basidiomycete Fulvifomes xylocarpicola associated with the mangrove tree Xylocarpus granatum" masterLastPageNumber="6" masterPageNumber="1" pageNumber="5" updateTime="1693397028374" updateUser="juliana">
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<mods:title id="1AD99A27FA87A41E82CE3DA5382ED30D">Limonoids from fruiting bodies of the wood-rot basidiomycete Fulvifomes xylocarpicola associated with the mangrove tree Xylocarpus granatum</mods:title>
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<mods:namePart id="291C33FABF6CA1466B2E86D2A64C12AE">Isaka, Masahiko</mods:namePart>
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<mods:affiliation id="160FB71F769453FA14DF8D3408B1F9B4">* & National Center for Genetic Engineering and Biotechnology (BIOTEC), 113 Thailand Science Park, Phaholyothin Road, Klong Luang, Pathumthani, 12120, Thailand</mods:affiliation>
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<mods:namePart id="E87230F4B1746CE9B8109754944AFEEF">Palasarn, Somporn</mods:namePart>
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<mods:namePart id="ECFBE09CB8AA4352F0421F3B4D5921AB">Sakayaroj, Jariya</mods:namePart>
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<mods:namePart id="9045B905F3F7C66EDC427728CD5E05E8">Srichomthong, Kitlada</mods:namePart>
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<mods:namePart id="ACDC9FDAAF315A697708C21837F7DF96">Nithithanasilp, Sutichai</mods:namePart>
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<mods:namePart id="71185ABB37F66929B9BE3AA041B10606">Sappan, Malipan</mods:namePart>
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<mods:title id="DE08A17EBC5E2013E6BCEEC907DB844C">Phytochemistry</mods:title>
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<mods:part id="37290527223624A08FE4205F681A2E3E">
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<mods:date id="14411DA3325E3C2BFB19B99D9738F26B">2021</mods:date>
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<mods:title id="5F4BD55F6AA8DADF7D8B70E8395326AE">112555</mods:title>
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<mods:number id="66E7C292AA899BEACDF622F5006334A3">2021-01-31</mods:number>
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<mods:url id="2CBE0A97CEFF753788C6BBCE6D712AB3">http://dx.doi.org/10.1016/j.phytochem.2020.112555</mods:url>
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<mods:classification id="4D6EFAB241E7E0B171F27EB18FD21CF6">journal article</mods:classification>
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<mods:identifier id="6D0822AF7BEBDE46743BD7B419EC1BD9" type="DOI">10.1016/j.phytochem.2020.112555</mods:identifier>
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<mods:identifier id="0187CD3CF7801CBACE7390B5E33AF8C8" type="ISSN">1873-3700</mods:identifier>
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<treatment id="03900A2CFF88FFF7FCBA98618D9F841C" LSID="urn:lsid:plazi:treatment:03900A2CFF88FFF7FCBA98618D9F841C" httpUri="http://treatment.plazi.org/id/03900A2CFF88FFF7FCBA98618D9F841C" lastPageId="5" lastPageNumber="6" pageId="4" pageNumber="5">
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<subSubSection id="C323E8B1FF88FFF6FCBA98618BB18593" pageId="4" pageNumber="5" type="nomenclature">
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<emphasis id="B94D6728FF88FFF6FCBA98618BB18593" bold="true" italics="true" pageId="4" pageNumber="5">
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||
4.5. LCMS analysis of the extracts from the fruiting body of
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<taxonomicName id="4C39C0B9FF88FFF6FAD198618CAA8594" ID-CoL="6JRY2" authority="T. Hatt, Sakayaroj & E. B. G. Jones" authorityName="T. Hatt, Sakayaroj & E. B. G. Jones" class="Agaricomycetes" family="Hymenochaetaceae" genus="Fulvifomes" kingdom="Fungi" order="Hymenochaetales" pageId="4" pageNumber="5" phylum="Basidiomycota" rank="species" species="xylocarpicola">F. xylocarpicola</taxonomicName>
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and the bark of
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<taxonomicName id="4C39C0B9FF88FFF6FBCA98858BB18593" authority="Koenig" authorityName="Koenig" box="[1090,1202,1433,1452]" class="Magnoliopsida" family="Meliaceae" genus="Xylocarpus" kingdom="Plantae" order="Sapindales" pageId="4" pageNumber="5" phylum="Tracheophyta" rank="species" species="granatum">X. granatum</taxonomicName>
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</emphasis>
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</paragraph>
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</subSubSection>
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<subSubSection id="C323E8B1FF88FFF7FCD998CD8D9F841C" lastPageId="5" lastPageNumber="6" pageId="4" pageNumber="5" type="description">
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<paragraph id="8B86BB3AFF88FFF6FCD998CD8CC28771" blockId="4.[818,1488,1488,1984]" pageId="4" pageNumber="5">
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In the collection of
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<taxonomicName id="4C39C0B9FF88FFF6FB8B98CD8B9385DC" box="[1027,1168,1488,1508]" class="Agaricomycetes" family="Hymenochaetaceae" genus="Fulvifomes" kingdom="Fungi" order="Hymenochaetales" pageId="4" pageNumber="5" phylum="Basidiomycota" rank="species" species="xylocarpicola">
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<emphasis id="B94D6728FF88FFF6FB8B98CD8B9385DC" bold="true" box="[1027,1168,1488,1508]" italics="true" pageId="4" pageNumber="5">F. xylocarpicola</emphasis>
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</taxonomicName>
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, after stripping off the mushroom, the plant side (bark) of the mushroom-bonded surface was scrapped to collect small crops (
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<figureCitation id="1302A7BFFF88FFF6FC629B148B2A8624" box="[1002,1065,1544,1563]" captionStart="Fig" captionStartId="1.[632,662,1964,1981]" captionTargetBox="[340,1248,975,1935]" captionTargetId="figure-695@1.[339,1249,974,1936]" captionTargetPageId="1" captionText="Fig. 1. Structures of compounds 1–5." figureDoi="http://doi.org/10.5281/zenodo.8291170" httpUri="https://zenodo.org/record/8291170/files/figure.png" pageId="4" pageNumber="5">Fig. S1</figureCitation>
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||
). Dried crops from plant bark (
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<quantity id="4CC116DFFF88FFF6FAC19B148A708624" box="[1353,1395,1544,1563]" metricMagnitude="-2" metricUnit="kg" metricValue="2.4" pageId="4" pageNumber="5" unit="g" value="24.0">24 g</quantity>
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) were cut into small pieces and extracted with
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<collectingCountry id="F32EFBAAFF88FFF6FB0C9B388BA28608" box="[1156,1185,1572,1591]" name="Switzerland" pageId="4" pageNumber="5">CH</collectingCountry>
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<subScript id="17BDB97FFF88FFF6FB299B378BA98606" attach="both" box="[1185,1194,1579,1593]" fontSize="6" pageId="4" pageNumber="5">2</subScript>
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Cl
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<subScript id="17BDB97FFF88FFF6FB369B378BC48606" attach="left" box="[1214,1223,1579,1593]" fontSize="6" pageId="4" pageNumber="5">2</subScript>
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(400 ml, room temperature, 7 days; twice), and combined
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<collectingCountry id="F32EFBAAFF88FFF6FBD89B5C8B6E866C" box="[1104,1133,1600,1619]" name="Switzerland" pageId="4" pageNumber="5">CH</collectingCountry>
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<subScript id="17BDB97FFF88FFF6FBE59B5B8B75866A" attach="both" box="[1133,1142,1607,1621]" fontSize="6" pageId="4" pageNumber="5">2</subScript>
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Cl
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<subScript id="17BDB97FFF88FFF6FB029B5B8B90866A" attach="left" box="[1162,1171,1607,1621]" fontSize="6" pageId="4" pageNumber="5">2</subScript>
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solution was concentrated under reduced pressure to obtain a
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<collectingCountry id="F32EFBAAFF88FFF6FBB69B408B588650" box="[1086,1115,1628,1647]" name="Switzerland" pageId="4" pageNumber="5">CH</collectingCountry>
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<subScript id="17BDB97FFF88FFF6FBD39B7F8B67864E" attach="both" box="[1115,1124,1635,1649]" fontSize="6" pageId="4" pageNumber="5">2</subScript>
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Cl
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<subScript id="17BDB97FFF88FFF6FBF09B7F8B82864E" attach="left" box="[1144,1153,1635,1649]" fontSize="6" pageId="4" pageNumber="5">2</subScript>
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extract (
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<quantity id="4CC116DFFF88FFF6FB5B9B408A1D8650" box="[1235,1310,1628,1647]" metricMagnitude="-4" metricUnit="kg" metricValue="3.03" pageId="4" pageNumber="5" unit="mg" value="303.0">303 mg</quantity>
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). The plant residue was then extracted with MeOH (500 ml, room temperature, 7 days; twice), and combined MeOH solution was concentrated under reduced pressure. The residue was dissolved in EtOAc (600 ml) and washed with
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<collectionCode id="ED2823FFFF88FFF6FCBA9BD08C4186E0" box="[818,834,1740,1759]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="4" pageNumber="5" type="Herbarium">H</collectionCode>
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<subScript id="17BDB97FFF88FFF6FCC99BCF8C4986DE" attach="both" box="[833,842,1747,1761]" fontSize="6" pageId="4" pageNumber="5">2</subScript>
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<collectionCode id="ED2823FFFF88FFF6FCC29BD08C5986E0" box="[842,858,1740,1759]" country="Norway" lsid="urn:lsid:biocol.org:col:13093" name="Botanical Museum - University of Oslo" pageId="4" pageNumber="5" type="Herbarium">O</collectionCode>
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(30 ml). The organic layer was concentrated under reduced pressure to obtain a MeOH extract (
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<quantity id="4CC116DFFF88FFF6FBDE9BFB8BA286C5" box="[1110,1185,1767,1786]" metricMagnitude="-4" metricUnit="kg" metricValue="4.17" pageId="4" pageNumber="5" unit="mg" value="417.0">417 mg</quantity>
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). These extracts and the extracts from
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<taxonomicName id="4C39C0B9FF88FFF6FCED9A1F8CF08729" box="[869,1011,1795,1814]" class="Agaricomycetes" family="Hymenochaetaceae" genus="Fulvifomes" kingdom="Fungi" order="Hymenochaetales" pageId="4" pageNumber="5" phylum="Basidiomycota" rank="species" species="xylocarpicola">
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<emphasis id="B94D6728FF88FFF6FCED9A1F8CF08729" bold="true" box="[869,1011,1795,1814]" italics="true" pageId="4" pageNumber="5">F. xylocarpicola</emphasis>
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</taxonomicName>
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fruiting body (described above) were subjected to LC-MS analysis for detection of fulvifomin A (
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<emphasis id="B94D6728FF88FFF6FB699A038BEE870D" bold="true" box="[1249,1261,1823,1842]" pageId="4" pageNumber="5">1</emphasis>
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), the major limonoid in the mushroom.
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</paragraph>
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<paragraph id="8B86BB3AFF88FFF7FCD99A4B8DAD810D" blockId="4.[818,1488,1488,1984]" lastBlockId="5.[100,770,148,307]" lastPageId="5" lastPageNumber="6" pageId="4" pageNumber="5">
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LC-MS analysis was performed using Bruker MicrOTOF mass spectrometer connected to Agilent 1200 Series
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<taxonomicName id="4C39C0B9FF88FFF6FB379A6F8BF787B9" box="[1215,1268,1907,1926]" pageId="4" pageNumber="5" rank="series" series="Hplc">HPLC</taxonomicName>
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system.
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<taxonomicName id="4C39C0B9FF88FFF6FACB9A6F8A7887B9" box="[1347,1403,1907,1926]" pageId="4" pageNumber="5" rank="series" series="Hplc">HPLC</taxonomicName>
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: column, Dionex Acclaim 120 C18, 4.6 ×
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<quantity id="4CC116DFFF88FFF6FBEF9A938BBA879D" box="[1127,1209,1935,1954]" metricMagnitude="-1" metricUnit="m" metricValue="1.5" pageId="4" pageNumber="5" unit="mm" value="150.0">150 mm</quantity>
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, 3 μm; mobile phase, MeCN/
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<collectionCode id="ED2823FFFF88FFF6FCBA9AB78C418781" box="[818,834,1963,1982]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="4" pageNumber="5" type="Herbarium">H</collectionCode>
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<subScript id="17BDB97FFF88FFF6FCC99AAE8C4987FF" attach="both" box="[833,842,1970,1984]" fontSize="6" pageId="4" pageNumber="5">2</subScript>
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<collectionCode id="ED2823FFFF88FFF6FCC29AB78C598781" box="[842,858,1963,1982]" country="Norway" lsid="urn:lsid:biocol.org:col:13093" name="Botanical Museum - University of Oslo" pageId="4" pageNumber="5" type="Herbarium">O</collectionCode>
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+0.05% formic acid, gradient from 5:95 to 95:5 over 50 min; flow rate, 0.3 ml/min; UV detection,
|
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<quantity id="4CC116DFFF89FFF7FE139D888EE48098" box="[411,487,148,167]" metricMagnitude="-7" metricUnit="m" metricValue="2.1" pageId="5" pageNumber="6" unit="nm" value="210.0">210 nm</quantity>
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. ESI-TOF (positive ion mode) mass trace was obtained for identification of fulvifomin A (
|
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<emphasis id="B94D6728FF89FFF7FD229DAC8DB580FC" bold="true" box="[682,694,176,195]" pageId="5" pageNumber="6">1</emphasis>
|
||
):
|
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<taxonomicName id="4C39C0B9FF89FFF7FD459DAC8C0180FC" box="[717,770,176,195]" pageId="5" pageNumber="5" rank="series" series="Hplc">HPLC</taxonomicName>
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retention time, 44.9 min; ESI-MS, [M+
|
||
<collectionCode id="ED2823FFFF89FFF7FE549DD08EEC80E0" box="[476,495,204,223]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="5" pageNumber="6" type="Herbarium">H</collectionCode>
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]
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<superScript id="7C4C1672FF89FFF7FE7D9DD48D0780EB" attach="left" box="[501,516,200,212]" fontSize="6" pageId="5" pageNumber="6">+</superScript>
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= 571 (Fig. S29). A 20 μl portion from
|
||
<quantity id="4CC116DFFF89FFF7FF699DFB8E2780C5" box="[225,292,231,250]" metricMagnitude="-7" metricUnit="kg" metricValue="5.0" pageId="5" pageNumber="6" unit="mg" value="0.5">0.5 mg</quantity>
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/ml MeOH solution of each extract was injected for the LC-MS. Compound
|
||
<emphasis id="B94D6728FF89FFF7FEC99C1F8E4E8129" bold="true" box="[321,333,259,278]" pageId="5" pageNumber="6">1</emphasis>
|
||
was detected in the extracts from the fungus, but, not in the extracts from the plant (Fig. S30 and Fig. S31).
|
||
</paragraph>
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<paragraph id="8B86BB3AFF89FFF7FFEC9C4B8E2581BA" blockId="5.[100,675,337,362]" lastBlockId="5.[100,294,370,390]" pageId="5" pageNumber="6">
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<heading id="D0CE0C56FF89FFF7FFEC9C4B8E2581BA" bold="true" fontSize="36" level="1" pageId="5" pageNumber="6" reason="1">
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<emphasis id="B94D6728FF89FFF7FFEC9C4B8E2581BA" bold="true" italics="true" pageId="5" pageNumber="6">
|
||
4.6. Fermentation of
|
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<taxonomicName id="4C39C0B9FF89FFF7FEA19C4B8EB98155" ID-CoL="6JRY2" box="[297,442,343,362]" class="Agaricomycetes" family="Hymenochaetaceae" genus="Fulvifomes" kingdom="Fungi" order="Hymenochaetales" pageId="5" pageNumber="6" phylum="Basidiomycota" rank="species" species="xylocarpicola">F. xylocarpicola</taxonomicName>
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, extraction, and
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H NMR spectroscopic analysis
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</emphasis>
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||
</heading>
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||
</paragraph>
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<paragraph id="8B86BB3AFF89FFF7FF0C9CB78D9F841C" blockId="5.[100,771,426,1060]" pageId="5" pageNumber="6">
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Four strains of
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<taxonomicName id="4C39C0B9FF89FFF7FE929CB78EA98182" box="[282,426,426,446]" class="Agaricomycetes" family="Hymenochaetaceae" genus="Fulvifomes" kingdom="Fungi" order="Hymenochaetales" pageId="5" pageNumber="6" phylum="Basidiomycota" rank="species" species="xylocarpicola">
|
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<emphasis id="B94D6728FF89FFF7FE929CB78EA98182" bold="true" box="[282,426,426,446]" italics="true" pageId="5" pageNumber="6">F. xylocarpicola</emphasis>
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</taxonomicName>
|
||
, which have been preserved at the BIOTEC Culture Collection (BCC 42654, BCC 47460, BCC 47461, and BCC 47478), were fermented using three different liquid media: malt extract broth (MEB; malt extract 6.0 g/l, yeast extract
|
||
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|
||
/l, maltose
|
||
<quantity id="4CC116DFFF89FFF7FFEC9F068F968212" box="[100,149,538,557]" metricMagnitude="-3" metricUnit="kg" metricValue="1.8" pageId="5" pageNumber="6" unit="g" value="1.8">1.8 g</quantity>
|
||
/l, dextrose 6.0 g/l), potato dextrose broth (PDB; potato starch 4.0 g/l, dextrose 20.0 g/l), and peptone yeast glucose medium (PYGM; bacteriological peptone 5.0 g/l, yeast extract 20.0 g/l, glucose 10.0 g/l, KH
|
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PO
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||
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||
1.0 g/l, MgSO
|
||
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⋅7H
|
||
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O
|
||
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|
||
/l). Each strain was fermented in a 1000 ml Erlenmeyer flask containing 250 ml of the liquid media under static conditions until good mycelial growth (19–32 days). Among 12 cultures, there were 4 cases of insufficient mycelial growth, and such cultures were discarded. Each culture was filtered to separate broth (filtrate) and mycelia (residue). The broth was extracted with EtOAc (250 ml), and the organic layer was concentrated under reduced pressure to obtain a broth extract (
|
||
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|
||
). The wet mycelia were macerated in MeOH (100 ml, room temperature, 2 days), then filtered. The filtrate was defatted by partitioning with hexane (50 ml). The aqueous MeOH (bottom) layer was concentrated under reduced pressure. The residue was dissolved in EtOAc (200 ml), washed with H
|
||
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||
O (50 ml), and concentrated under reduced pressure to obtain a mycelial extract (
|
||
<quantity id="4CC116DFFF89FFF7FF3A9EC58E0483D3" box="[178,263,985,1004]" metricMagnitude="-6" metricUnit="kg" metricValue="9.5" metricValueMax="16.0" metricValueMin="3.0" pageId="5" pageNumber="6" unit="mg" value="9.5" valueMax="16.0" valueMin="3.0">3–16 mg</quantity>
|
||
). The broth and mycelial extracts were subjected to
|
||
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|
||
H NMR spectroscopic analysis. The spectra strongly suggested that none of the extracts contained any limonoids in detectable quantity.
|
||
</paragraph>
|
||
</subSubSection>
|
||
</treatment>
|
||
</document> |