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<document id="A88AE4388175207570FECF32A966C324" ID-DOI="10.1016/j.phytochem.2014.07.013" ID-ISSN="1873-3700" ID-Zenodo-Dep="10489523" IM.bibliography_approvedBy="carolina" IM.illustrations_approvedBy="carolina" IM.materialsCitations_approvedBy="felipe" IM.metadata_approvedBy="felipe" IM.tables_approvedBy="carolina" IM.taxonomicNames_approvedBy="carolina" IM.treatments_approvedBy="carolina" checkinTime="1704958063113" checkinUser="felipe" docAuthor="Yan, Zhiqiang, Guo, Hongru, Yang, Jiayue, Liu, Quan, Jin, Hui, Xu, Rui, Cui, Haiyan &amp; Qin, Bo" docDate="2014" docId="7B1D87B4335DFF90FFD5F922FE65901F" docLanguage="en" docName="Phytochemistry.106.61-68.pdf" docOrigin="Phytochemistry 106" docSource="http://dx.doi.org/10.1016/j.phytochem.2014.07.013" docStyle="DocumentStyle:9E596C34F4E94307D29315B03ACE1007.6:Phytochemistry.2014-2019.journal_article" docStyleId="9E596C34F4E94307D29315B03ACE1007" docStyleName="Phytochemistry.2014-2019.journal_article" docStyleVersion="6" docTitle="Stellera chamaejasme L." docType="treatment" docVersion="4" lastPageNumber="63" masterDocId="8724FFCC335CFF92FF82FF91FFC49674" masterDocTitle="Phytotoxic flavonoids from roots of Stellera chamaejasme L. (Thymelaeaceae)" masterLastPageNumber="68" masterPageNumber="61" pageNumber="62" updateTime="1706104341162" updateUser="carolina">
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<mods:title id="AAE13FB6D2031CB29AA4F2FE5AB718F6">Phytotoxic flavonoids from roots of Stellera chamaejasme L. (Thymelaeaceae)</mods:title>
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2.2. Phytotoxic activity of flavonoids from
<taxonomicName id="34B44D21335DFF93FE70F922FD4F90B3" ID-CoL="4ZRSY" authorityName="L." box="[498,651,1715,1735]" class="Magnoliopsida" family="Thymelaeaceae" genus="Stellera" kingdom="Plantae" order="Malvales" pageId="1" pageNumber="62" phylum="Tracheophyta" rank="species" species="chamaejasme">S. chamaejasme</taxonomicName>
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Flavonoids are known to exhibit a wide range of functions in plant physiology, biochemistry and ecology (
<bibRefCitation id="97254B53335DFF93FDF5F899FF3B9143" author="Taylor, L. P. &amp; Grotewold, E." pageId="1" pageNumber="62" pagination="317 - 323" refId="ref9582" refString="Taylor, L. P., Grotewold, E., 2005. Flavonoids as developmental regulators. Curr. Opin. Plant Biol. 8, 317 - 323." type="journal article" year="2005">Taylor and Grotewold, 2005</bibRefCitation>
). They have been reported to be involved in allelopathic effects (
<bibRefCitation id="97254B53335DFF93FE85F8D1FE5E9127" author="Treutter, D." box="[263,410,1856,1875]" pageId="1" pageNumber="62" pagination="147 - 157" refId="ref9614" refString="Treutter, D., 2006. Significance of flavonoids in plant resistance: a review. Environ. Chem. Lett. 4, 147 - 157." type="journal article" year="2006">Treutter, 2006</bibRefCitation>
). Thus, two flavone
<emphasis id="C1C0EAB0335DFF93FDF4F8AEFD419127" box="[630,645,1855,1875]" italics="true" pageId="1" pageNumber="62">O</emphasis>
-glycosides isolated from rice seedlings showed strong inhibition on the growth of
<emphasis id="C1C0EAB0335DFF93FF40F8E6FE5291FF" box="[194,406,1911,1931]" italics="true" pageId="1" pageNumber="62">
<taxonomicName id="34B44D21335DFF93FF40F8E6FEA191FF" box="[194,357,1911,1931]" class="Liliopsida" family="Poaceae" genus="Echinochloa" kingdom="Plantae" order="Poales" pageId="1" pageNumber="62" phylum="Tracheophyta" rank="species" species="crus">Echinochloa crus</taxonomicName>
-galli
</emphasis>
and
<taxonomicName id="34B44D21335DFF93FE48F8E6FF5791D3" authority="(Kong et al., 2007)" baseAuthorityName="Kong" baseAuthorityYear="2007" class="Liliopsida" family="Cyperaceae" genus="Cyperus" kingdom="Plantae" order="Poales" pageId="1" pageNumber="62" phylum="Tracheophyta" rank="species" species="difformis">
<emphasis id="C1C0EAB0335DFF93FE48F8E6FDB791FF" box="[458,627,1911,1931]" italics="true" pageId="1" pageNumber="62">Cyperus difformis</emphasis>
(
<bibRefCitation id="97254B53335DFF93FD01F8E9FF4D91D3" author="Kong, C. H. &amp; Zhao, H. &amp; Xu, X. H. &amp; Wang, P. &amp; Gu, Y." pageId="1" pageNumber="62" pagination="6007 - 6012" refId="ref8324" refString="Kong, C. H., Zhao, H., Xu, X. H., Wang, P., Gu, Y., 2007. Activity and allelopathy of soil of flavone O - glycosides from rice. J. Agric. Food Chem. 55, 6007 - 6012." type="journal article" year="2007">Kong et al., 2007</bibRefCitation>
)
</taxonomicName>
. The flavone luteolin from
<taxonomicName id="34B44D21335DFF93FE26F802FD7791D3" box="[420,691,1939,1959]" class="Magnoliopsida" family="Asteraceae" genus="Chrysanthemum" kingdom="Plantae" order="Asterales" pageId="1" pageNumber="62" phylum="Tracheophyta" rank="species" species="morifolium">
<emphasis id="C1C0EAB0335DFF93FE26F802FD7791D3" box="[420,691,1939,1959]" italics="true" pageId="1" pageNumber="62">Chrysanthemum morifolium</emphasis>
</taxonomicName>
L. significantly reduced the frond number and chlorophyll content of
<taxonomicName id="34B44D21335DFF93FFD5F85BFF1691AA" box="[87,210,1994,2014]" class="Liliopsida" family="Araceae" genus="Lemna" kingdom="Plantae" order="Alismatales" pageId="1" pageNumber="62" phylum="Tracheophyta" rank="species" species="gibba">
<emphasis id="C1C0EAB0335DFF93FFD5F85BFF1691AA" box="[87,210,1994,2014]" italics="true" pageId="1" pageNumber="62">Lemna gibba</emphasis>
</taxonomicName>
plants (
<bibRefCitation id="97254B53335DFF93FEA5F85AFDDF91AA" author="Beninger, C. W. &amp; Hall, J. C." box="[295,539,1995,2014]" pageId="1" pageNumber="62" pagination="103 - 111" refId="ref7541" refString="Beninger, C. W., Hall, J. C., 2005. Allelopathic activity of luteolin 7 - O - β- glucuronide isolated from Chrysanthemum morifolium L. Biochem. Syst. Ecol. 33, 103 - 111." type="journal article" year="2005">Beninger and Hall, 2005</bibRefCitation>
).
</paragraph>
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In the study herein, compounds
<emphasis id="C1C0EAB0335DFF93FB17F907FB7890DD" bold="true" box="[1173,1212,1686,1705]" pageId="1" pageNumber="62">18</emphasis>
were assayed for phenotypic and growth effects on seven-day-old
<taxonomicName id="34B44D21335DFF93FB68F920FA7B90B1" box="[1258,1471,1713,1733]" class="Magnoliopsida" family="Brassicaceae" genus="Arabidopsis" kingdom="Plantae" order="Brassicales" pageId="1" pageNumber="63" phylum="Tracheophyta" rank="subSpecies" species="thaliana" subSpecies="seedlings">
<emphasis id="C1C0EAB0335DFF93FB68F920FA9190B1" box="[1258,1365,1713,1733]" italics="true" pageId="1" pageNumber="62">A. thaliana</emphasis>
seedlings
</taxonomicName>
. Results indicated that all of the compounds isolated by the bioassay-guided fractionation of
<taxonomicName id="34B44D21335DFF93FBC9F978FB2D9089" box="[1099,1257,1769,1789]" class="Magnoliopsida" family="Thymelaeaceae" genus="Stellera" kingdom="Plantae" order="Malvales" pageId="1" pageNumber="62" phylum="Tracheophyta" rank="species" species="chamaejasme">
<emphasis id="C1C0EAB0335DFF93FBC9F978FB2D9089" box="[1099,1257,1769,1789]" italics="true" pageId="1" pageNumber="62">S. chamaejasme</emphasis>
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decreased the fresh weight of
<taxonomicName id="34B44D21335DFF93FC08F895FB90916C" box="[906,1108,1796,1816]" class="Magnoliopsida" family="Brassicaceae" genus="Arabidopsis" kingdom="Plantae" order="Brassicales" pageId="1" pageNumber="63" phylum="Tracheophyta" rank="subSpecies" species="thaliana" subSpecies="seedlings">
<emphasis id="C1C0EAB0335DFF93FC08F895FC35916C" box="[906,1009,1796,1816]" italics="true" pageId="1" pageNumber="62">A. thaliana</emphasis>
seedlings
</taxonomicName>
(
<tableCitation id="BE360319335DFF93FBE0F894FB68916D" box="[1122,1196,1797,1817]" captionStart="Table 1" captionStartId="2.[114,158,183,197]" captionTargetPageId="2" captionText="Table 1 Phytotoxic effect of flavonoids from root of S. chamaejasme on A. thaliana seedlings." pageId="1" pageNumber="62">Table 1</tableCitation>
). Among these compounds,
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and
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showed significant inhibitory effects, and the concentrations required for 50% inhibition in the assay (defined as IC
<subScript id="6F3034E7335DFF93FA2AF8D7FA7E9126" attach="left" box="[1448,1466,1862,1874]" fontSize="5" pageId="1" pageNumber="62">50</subScript>
) were 6.9, 12.1, 43.2, 74.8, 7.1 and 27.3 µg/mL, respectively. Compounds
<emphasis id="C1C0EAB0335DFF93FCFBF8E4FC4291FC" bold="true" box="[889,902,1909,1928]" pageId="1" pageNumber="62">4</emphasis>
and
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only showed slight inhibitory effects. After the administration of compounds
<emphasis id="C1C0EAB0335DFF93FBDBF800FBBB91D0" bold="true" box="[1113,1151,1937,1956]" pageId="1" pageNumber="62">13</emphasis>
and
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for 7 days, the treated plants showed wilting symptoms prior to senescence with morphological alteration of roots (data not shown). The fresh weights of the
<taxonomicName id="34B44D21335EFF90FF32FD33FEBD94C2" box="[176,377,674,694]" class="Magnoliopsida" family="Brassicaceae" genus="Arabidopsis" kingdom="Plantae" order="Brassicales" pageId="2" pageNumber="63" phylum="Tracheophyta" rank="subSpecies" species="thaliana" subSpecies="seedlings">
<emphasis id="C1C0EAB0335EFF90FF32FD33FED394C2" box="[176,279,674,694]" italics="true" pageId="2" pageNumber="63">A. thaliana</emphasis>
seedlings
</taxonomicName>
treated with compounds
<emphasis id="C1C0EAB0335EFF90FDF8FD32FD6494C2" bold="true" box="[634,672,675,695]" pageId="2" pageNumber="63">13</emphasis>
and
<emphasis id="C1C0EAB0335EFF90FD52FD32FD3294C2" bold="true" box="[720,758,675,695]" pageId="2" pageNumber="63">68</emphasis>
at 25 µg/mL were reduced by 94.1%, 59.8%, 25.9%, 6.2%, 85.7% and 38%, respectively, compared to that of the control. Compounds
<emphasis id="C1C0EAB0335EFF90FD7FFD4AFCCE949A" bold="true" box="[765,778,731,750]" pageId="2" pageNumber="63">1</emphasis>
,
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and
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showed significant activity on
<taxonomicName id="34B44D21335EFF90FD99FD67FD34957E" box="[539,752,758,778]" class="Magnoliopsida" family="Brassicaceae" genus="Arabidopsis" kingdom="Plantae" order="Brassicales" pageId="2" pageNumber="63" phylum="Tracheophyta" rank="subSpecies" species="thaliana" subSpecies="seedlings">
<emphasis id="C1C0EAB0335EFF90FD99FD67FD43957E" box="[539,647,758,778]" italics="true" pageId="2" pageNumber="63">A. thaliana</emphasis>
seedlings
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at low concentrations (
<emphasis id="C1C0EAB0335EFF90FECCFC82FE9B9552" bold="true" box="[334,351,787,806]" italics="true" pageId="2" pageNumber="63">6</emphasis>
50 µg/mL), and this resulted in arrested growth of treated plants at high concentrations (
<emphasis id="C1C0EAB0335EFF90FD02FCBFFD529536" bold="true" box="[640,662,814,834]" italics="true" pageId="2" pageNumber="63">À</emphasis>
100 µg/mL), but without mortality. Compounds
<emphasis id="C1C0EAB0335EFF90FE5FFCDAFE2E952A" bold="true" box="[477,490,843,862]" pageId="2" pageNumber="63">3</emphasis>
,
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and
<emphasis id="C1C0EAB0335EFF90FDBAFCDAFD81952A" bold="true" box="[568,581,843,862]" pageId="2" pageNumber="63">8</emphasis>
were not as phytotoxic as compounds
<emphasis id="C1C0EAB0335EFF90FEC8FCF7FE93950D" bold="true" box="[330,343,870,889]" pageId="2" pageNumber="63">1</emphasis>
,
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and
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at low concentrations, but were effective at high concentrations; compound
<emphasis id="C1C0EAB0335EFF90FDAAFC13FDF195E1" bold="true" box="[552,565,898,917]" pageId="2" pageNumber="63">3</emphasis>
even killed the plants at 100 µg/mL (data not shown).
</paragraph>
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<emphasis id="C1C0EAB0335EFF90FFF0FF26FF6A96B1" bold="true" box="[114,174,183,197]" pageId="2" pageNumber="63">Table 1</emphasis>
Phytotoxic effect of flavonoids from root of
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<emphasis id="C1C0EAB0335EFF90FE4CFF5DFD8296A8" box="[462,582,204,220]" italics="true" pageId="2" pageNumber="63">S. chamaejasme</emphasis>
</taxonomicName>
on
<taxonomicName id="34B44D21335EFF90FDE7FF5CFCC296A8" box="[613,774,205,220]" class="Magnoliopsida" family="Brassicaceae" genus="Arabidopsis" kingdom="Plantae" order="Brassicales" pageId="2" pageNumber="63" phylum="Tracheophyta" rank="subSpecies" species="thaliana" subSpecies="seedlings">
<emphasis id="C1C0EAB0335EFF90FDE7FF5CFD7396A8" box="[613,695,205,220]" italics="true" pageId="2" pageNumber="63">A. thaliana</emphasis>
seedlings
</taxonomicName>
.
</paragraph>
</caption>
<paragraph id="F30B36A2335EFF90FE19FF65FA559791" pageId="2" pageNumber="63">
<table id="81B4C402335E006DFF0AFF65FA019792" box="[136,1477,244,486]" gridcols="10" gridrows="10" pageId="2" pageNumber="63">
<tr id="4D8434E0335E006DFF0AFF65FA019770" box="[136,1477,244,260]" gridrow="0" pageId="2" pageNumber="63" rowspan-0="1" rowspan-4="1" rowspan-5="1" rowspan-6="1" rowspan-7="1" rowspan-8="1">
<th id="0E555D9C335E006DFE19FF65FCCB9770" box="[411,783,244,260]" colspan="3" colspanRight="2" gridcol="1" gridrow="0" pageId="2" pageNumber="63">Fresh weight, % of control (Mean ± SE)</th>
<th id="0E555D9C335E006DFAECFF65FA019770" box="[1390,1477,244,260]" gridcol="9" gridrow="0" pageId="2" pageNumber="63">IC50 values</th>
</tr>
<tr id="4D8434E0335E006DFF0AFE99FA019751" box="[136,1477,264,293]" gridrow="1" pageId="2" pageNumber="63" rowspan-0="1">
<td id="0E555D9C335E006DFE19FE99FDD59751" box="[411,529,264,293]" gridcol="1" gridrow="1" pageId="2" pageNumber="63">1.25 µg/mL</td>
<td id="0E555D9C335E006DFD9DFE99FD519751" box="[543,661,264,293]" gridcol="2" gridrow="1" pageId="2" pageNumber="63">2.5 µg/mL</td>
<td id="0E555D9C335E006DFD21FE99FCCB9751" box="[675,783,264,293]" gridcol="3" gridrow="1" pageId="2" pageNumber="63">5 µg/mL</td>
<td id="0E555D9C335E006DFC9FFE99FC429751" box="[797,902,264,293]" gridcol="4" gridrow="1" pageId="2" pageNumber="63">10 µg/mL</td>
<td id="0E555D9C335E006DFC16FE99FC399751" box="[916,1021,264,293]" gridcol="5" gridrow="1" pageId="2" pageNumber="63">25 µg/mL</td>
<td id="0E555D9C335E006DFB88FE99FBB79751" box="[1034,1139,264,293]" gridcol="6" gridrow="1" pageId="2" pageNumber="63">50 µg/mL</td>
<td id="0E555D9C335E006DFB03FE99FB2E9751" box="[1153,1258,264,293]" gridcol="7" gridrow="1" pageId="2" pageNumber="63">100 µg/mL</td>
<td id="0E555D9C335E006DFB75FE99FAA49751" box="[1271,1376,264,293]" gridcol="8" gridrow="1" pageId="2" pageNumber="63">200 µg/mL</td>
<td id="0E555D9C335E006DFAECFE99FA019751" box="[1390,1477,264,293]" gridcol="9" gridrow="1" pageId="2" pageNumber="63">(µg/mL)</td>
</tr>
<tr id="4D8434E0335E006DFF0AFEA2FA019732" box="[136,1477,307,326]" gridrow="2" pageId="2" pageNumber="63">
<th id="0E555D9C335E006DFF0AFEA2FE499732" box="[136,397,307,326]" gridcol="0" gridrow="2" pageId="2" pageNumber="63">
Neochamaejasmin B (
<emphasis id="C1C0EAB0335EFF90FEBBFEA6FE879731" bold="true" box="[313,323,311,325]" pageId="2" pageNumber="63">1</emphasis>
)
</th>
<td id="0E555D9C335E006DFE19FEA2FDD59732" box="[411,529,307,326]" gridcol="1" gridrow="2" pageId="2" pageNumber="63">90.13 ± 7.64</td>
<td id="0E555D9C335E006DFD9DFEA2FD519732" box="[543,661,307,326]" gridcol="2" gridrow="2" pageId="2" pageNumber="63">83.22 ± 9.58</td>
<td id="0E555D9C335E006DFD21FEA2FCCB9732" box="[675,783,307,326]" gridcol="3" gridrow="2" pageId="2" pageNumber="63">52.08 ± 8.44*</td>
<td id="0E555D9C335E006DFC9FFEA2FC429732" box="[797,902,307,326]" gridcol="4" gridrow="2" pageId="2" pageNumber="63">33.62 ± 3.66*</td>
<td id="0E555D9C335E006DFC16FEA2FC399732" box="[916,1021,307,326]" gridcol="5" gridrow="2" pageId="2" pageNumber="63">15.87 ± 1.30*</td>
<td id="0E555D9C335E006DFB88FEA2FBB79732" box="[1034,1139,307,326]" gridcol="6" gridrow="2" pageId="2" pageNumber="63">11.09 ± 2.97*</td>
<td id="0E555D9C335E006DFB03FEA2FB2E9732" box="[1153,1258,307,326]" gridcol="7" gridrow="2" pageId="2" pageNumber="63">4.25 ± 1.05*</td>
<td id="0E555D9C335E006DFB75FEA2FAA49732" box="[1271,1376,307,326]" gridcol="8" gridrow="2" pageId="2" pageNumber="63">2.20 ± 0.99*</td>
<td id="0E555D9C335E006DFAECFEA2FA019732" box="[1390,1477,307,326]" gridcol="9" gridrow="2" pageId="2" pageNumber="63">6.9</td>
</tr>
<tr id="4D8434E0335E006DFF0AFEDBFA019729" box="[136,1477,330,349]" gridrow="3" pageId="2" pageNumber="63">
<th id="0E555D9C335E006DFF0AFEDBFE499729" box="[136,397,330,349]" gridcol="0" gridrow="3" pageId="2" pageNumber="63">
Mesoneochamaejasmin A (
<emphasis id="C1C0EAB0335EFF90FEE1FEDFFEA99728" bold="true" box="[355,365,334,348]" pageId="2" pageNumber="63">2</emphasis>
)
</th>
<td id="0E555D9C335E006DFE19FEDBFDD59729" box="[411,529,330,349]" gridcol="1" gridrow="3" pageId="2" pageNumber="63">81.81 ± 4.84</td>
<td id="0E555D9C335E006DFD9DFEDBFD519729" box="[543,661,330,349]" gridcol="2" gridrow="3" pageId="2" pageNumber="63">64.86 ± 9.45*</td>
<td id="0E555D9C335E006DFD21FEDBFCCB9729" box="[675,783,330,349]" gridcol="3" gridrow="3" pageId="2" pageNumber="63">54.19 ± 3.34*</td>
<td id="0E555D9C335E006DFC9FFEDBFC429729" box="[797,902,330,349]" gridcol="4" gridrow="3" pageId="2" pageNumber="63">40.38 ± 4.28*</td>
<td id="0E555D9C335E006DFC16FEDBFC399729" box="[916,1021,330,349]" gridcol="5" gridrow="3" pageId="2" pageNumber="63">40.16 ± 1.79*</td>
<td id="0E555D9C335E006DFB88FEDBFBB79729" box="[1034,1139,330,349]" gridcol="6" gridrow="3" pageId="2" pageNumber="63">29.02 ± 1.23*</td>
<td id="0E555D9C335E006DFB03FEDBFB2E9729" box="[1153,1258,330,349]" gridcol="7" gridrow="3" pageId="2" pageNumber="63">9.72 ± 1.73*</td>
<td id="0E555D9C335E006DFB75FEDBFAA49729" box="[1271,1376,330,349]" gridcol="8" gridrow="3" pageId="2" pageNumber="63">6.02 ± 0.61*</td>
<td id="0E555D9C335E006DFAECFEDBFA019729" box="[1390,1477,330,349]" gridcol="9" gridrow="3" pageId="2" pageNumber="63">12.1</td>
</tr>
<tr id="4D8434E0335E006DFF0AFEF0FA019707" box="[136,1477,353,371]" gridrow="4" pageId="2" pageNumber="63">
<th id="0E555D9C335E006DFF0AFEF0FE499707" box="[136,397,353,371]" gridcol="0" gridrow="4" pageId="2" pageNumber="63">
Chamaejasmenin C (
<emphasis id="C1C0EAB0335EFF90FEADFEF4FEFD9707" bold="true" box="[303,313,357,371]" pageId="2" pageNumber="63">3</emphasis>
)
</th>
<td id="0E555D9C335E006DFE19FEF0FDD59707" box="[411,529,353,371]" gridcol="1" gridrow="4" pageId="2" pageNumber="63">83.91 ± 6.74</td>
<td id="0E555D9C335E006DFD9DFEF0FD519707" box="[543,661,353,371]" gridcol="2" gridrow="4" pageId="2" pageNumber="63">74.26 ± 7.12</td>
<td id="0E555D9C335E006DFD21FEF0FCCB9707" box="[675,783,353,371]" gridcol="3" gridrow="4" pageId="2" pageNumber="63">70.67 ± 4.23*</td>
<td id="0E555D9C335E006DFC9FFEF0FC429707" box="[797,902,353,371]" gridcol="4" gridrow="4" pageId="2" pageNumber="63">73.74 ± 5.11</td>
<td id="0E555D9C335E006DFC16FEF0FC399707" box="[916,1021,353,371]" gridcol="5" gridrow="4" pageId="2" pageNumber="63">74.11 ± 5.79</td>
<td id="0E555D9C335E006DFB88FEF0FBB79707" box="[1034,1139,353,371]" gridcol="6" gridrow="4" pageId="2" pageNumber="63">50.79 ± 1.54*</td>
<td id="0E555D9C335E006DFB03FEF0FB2E9707" box="[1153,1258,353,371]" gridcol="7" gridrow="4" pageId="2" pageNumber="63">3.90 ± 0.77*</td>
<td id="0E555D9C335E006DFB75FEF0FAA49707" box="[1271,1376,353,371]" gridcol="8" gridrow="4" pageId="2" pageNumber="63">2.11 ± 0.33*</td>
<td id="0E555D9C335E006DFAECFEF0FA019707" box="[1390,1477,353,371]" gridcol="9" gridrow="4" pageId="2" pageNumber="63">43.2</td>
</tr>
<tr id="4D8434E0335E006DFF0AFEEDFA0197FE" box="[136,1477,380,394]" gridrow="5" pageId="2" pageNumber="63">
<th id="0E555D9C335E006DFF0AFEEDFE4997FE" box="[136,397,380,394]" gridcol="0" gridrow="5" pageId="2" pageNumber="63">
7-Methoxylneochaejasmin A (
<emphasis id="C1C0EAB0335EFF90FEFEFEEDFE4297FE" bold="true" box="[380,390,380,394]" pageId="2" pageNumber="63">4</emphasis>
)
</th>
<td id="0E555D9C335E006DFE19FEEDFDD597FE" box="[411,529,380,394]" gridcol="1" gridrow="5" pageId="2" pageNumber="63">101.73 ± 12.37</td>
<td id="0E555D9C335E006DFD9DFEEDFD5197FE" box="[543,661,380,394]" gridcol="2" gridrow="5" pageId="2" pageNumber="63">102.16 ± 14.57</td>
<td id="0E555D9C335E006DFD21FEEDFCCB97FE" box="[675,783,380,394]" gridcol="3" gridrow="5" pageId="2" pageNumber="63">98.34 ± 11.43</td>
<td id="0E555D9C335E006DFC9FFEEDFC4297FE" box="[797,902,380,394]" gridcol="4" gridrow="5" pageId="2" pageNumber="63">89.59 ± 5.89</td>
<td id="0E555D9C335E006DFC16FEEDFC3997FE" box="[916,1021,380,394]" gridcol="5" gridrow="5" pageId="2" pageNumber="63">93.25 ± 4.69</td>
<td id="0E555D9C335E006DFB88FEEDFBB797FE" box="[1034,1139,380,394]" gridcol="6" gridrow="5" pageId="2" pageNumber="63">85.82 ± 6.90</td>
<td id="0E555D9C335E006DFB03FEEDFB2E97FE" box="[1153,1258,380,394]" gridcol="7" gridrow="5" pageId="2" pageNumber="63">88.62 ± 2.49</td>
<td id="0E555D9C335E006DFB75FEEDFAA497FE" box="[1271,1376,380,394]" gridcol="8" gridrow="5" pageId="2" pageNumber="63">78.03 ± 1.69</td>
<td id="0E555D9C335E006DFAECFEEDFA0197FE" box="[1390,1477,380,394]" gridcol="9" gridrow="5" pageId="2" pageNumber="63">&gt;200</td>
</tr>
<tr id="4D8434E0335E006DFF0AFE02FA0197D5" box="[136,1477,403,417]" gridrow="6" pageId="2" pageNumber="63">
<th id="0E555D9C335E006DFF0AFE02FE4997D5" box="[136,397,403,417]" gridcol="0" gridrow="6" pageId="2" pageNumber="63">
(+)-Epiafzelechin (
<emphasis id="C1C0EAB0335EFF90FE9FFE02FEE397D5" bold="true" box="[285,295,403,417]" pageId="2" pageNumber="63">5</emphasis>
)
</th>
<td id="0E555D9C335E006DFE19FE02FDD597D5" box="[411,529,403,417]" gridcol="1" gridrow="6" pageId="2" pageNumber="63">96.04 ± 15.4</td>
<td id="0E555D9C335E006DFD9DFE02FD5197D5" box="[543,661,403,417]" gridcol="2" gridrow="6" pageId="2" pageNumber="63">98.87 ± 3.78</td>
<td id="0E555D9C335E006DFD21FE02FCCB97D5" box="[675,783,403,417]" gridcol="3" gridrow="6" pageId="2" pageNumber="63">85.7 ± 7.36</td>
<td id="0E555D9C335E006DFC9FFE02FC4297D5" box="[797,902,403,417]" gridcol="4" gridrow="6" pageId="2" pageNumber="63">76.73 ± 9.21</td>
<td id="0E555D9C335E006DFC16FE02FC3997D5" box="[916,1021,403,417]" gridcol="5" gridrow="6" pageId="2" pageNumber="63">70.47 ± 4.91</td>
<td id="0E555D9C335E006DFB88FE02FBB797D5" box="[1034,1139,403,417]" gridcol="6" gridrow="6" pageId="2" pageNumber="63">77.87 ± 8.06</td>
<td id="0E555D9C335E006DFB03FE02FB2E97D5" box="[1153,1258,403,417]" gridcol="7" gridrow="6" pageId="2" pageNumber="63">66.84 ± 4.75</td>
<td id="0E555D9C335E006DFB75FE02FAA497D5" box="[1271,1376,403,417]" gridcol="8" gridrow="6" pageId="2" pageNumber="63">65.41 ± 2.32</td>
<td id="0E555D9C335E006DFAECFE02FA0197D5" box="[1390,1477,403,417]" gridcol="9" gridrow="6" pageId="2" pageNumber="63">&gt;200</td>
</tr>
<tr id="4D8434E0335E006DFF0AFE34FA0197CC" box="[136,1477,421,440]" gridrow="7" pageId="2" pageNumber="63">
<th id="0E555D9C335E006DFF0AFE34FE4997CC" box="[136,397,421,440]" gridcol="0" gridrow="7" pageId="2" pageNumber="63">
Genkwanol A (
<emphasis id="C1C0EAB0335EFF90FE83FE38FECF97C3" bold="true" box="[257,267,425,439]" pageId="2" pageNumber="63">6</emphasis>
)
</th>
<td id="0E555D9C335E006DFE19FE34FDD597CC" box="[411,529,421,440]" gridcol="1" gridrow="7" pageId="2" pageNumber="63">99.24 ± 6.81</td>
<td id="0E555D9C335E006DFD9DFE34FD5197CC" box="[543,661,421,440]" gridcol="2" gridrow="7" pageId="2" pageNumber="63">95.35 ± 2.47</td>
<td id="0E555D9C335E006DFD21FE34FCCB97CC" box="[675,783,421,440]" gridcol="3" gridrow="7" pageId="2" pageNumber="63">87.8 ± 10.52</td>
<td id="0E555D9C335E006DFC9FFE34FC4297CC" box="[797,902,421,440]" gridcol="4" gridrow="7" pageId="2" pageNumber="63">87.57 ± 4.59</td>
<td id="0E555D9C335E006DFC16FE34FC3997CC" box="[916,1021,421,440]" gridcol="5" gridrow="7" pageId="2" pageNumber="63">93.82 ± 7.11</td>
<td id="0E555D9C335E006DFB88FE34FBB797CC" box="[1034,1139,421,440]" gridcol="6" gridrow="7" pageId="2" pageNumber="63">81.00 ± 7.40</td>
<td id="0E555D9C335E006DFB03FE34FB2E97CC" box="[1153,1258,421,440]" gridcol="7" gridrow="7" pageId="2" pageNumber="63">25.90 ± 6.03 *</td>
<td id="0E555D9C335E006DFB75FE34FAA497CC" box="[1271,1376,421,440]" gridcol="8" gridrow="7" pageId="2" pageNumber="63">17.11 ± 1.22 *</td>
<td id="0E555D9C335E006DFAECFE34FA0197CC" box="[1390,1477,421,440]" gridcol="9" gridrow="7" pageId="2" pageNumber="63">74.8</td>
</tr>
<tr id="4D8434E0335E006DFF0AFE2DFA0197BB" box="[136,1477,444,463]" gridrow="8" pageId="2" pageNumber="63">
<th id="0E555D9C335E006DFF0AFE2DFE4997BB" box="[136,397,444,463]" gridcol="0" gridrow="8" pageId="2" pageNumber="63">
Daphnodorin B (
<emphasis id="C1C0EAB0335EFF90FE8CFE51FEDC97BA" bold="true" box="[270,280,448,462]" pageId="2" pageNumber="63">7</emphasis>
)
</th>
<td id="0E555D9C335E006DFE19FE2DFDD597BB" box="[411,529,444,463]" gridcol="1" gridrow="8" pageId="2" pageNumber="63">90.18 ± 6.06</td>
<td id="0E555D9C335E006DFD9DFE2DFD5197BB" box="[543,661,444,463]" gridcol="2" gridrow="8" pageId="2" pageNumber="63">87.57 ± 4.01</td>
<td id="0E555D9C335E006DFD21FE2DFCCB97BB" box="[675,783,444,463]" gridcol="3" gridrow="8" pageId="2" pageNumber="63">68.34 ± 7.30</td>
<td id="0E555D9C335E006DFC9FFE2DFC4297BB" box="[797,902,444,463]" gridcol="4" gridrow="8" pageId="2" pageNumber="63">39.59 ± 2.68*</td>
<td id="0E555D9C335E006DFC16FE2DFC3997BB" box="[916,1021,444,463]" gridcol="5" gridrow="8" pageId="2" pageNumber="63">14.27 ± 1.07*</td>
<td id="0E555D9C335E006DFB88FE2DFBB797BB" box="[1034,1139,444,463]" gridcol="6" gridrow="8" pageId="2" pageNumber="63">12.04 ± 4.75*</td>
<td id="0E555D9C335E006DFB03FE2DFB2E97BB" box="[1153,1258,444,463]" gridcol="7" gridrow="8" pageId="2" pageNumber="63">10.73 ± 2.38*</td>
<td id="0E555D9C335E006DFB75FE2DFAA497BB" box="[1271,1376,444,463]" gridcol="8" gridrow="8" pageId="2" pageNumber="63">4.06 ± 0.86*</td>
<td id="0E555D9C335E006DFAECFE2DFA0197BB" box="[1390,1477,444,463]" gridcol="9" gridrow="8" pageId="2" pageNumber="63">7.1</td>
</tr>
<tr id="4D8434E0335E006DFF0AFE42FA019792" box="[136,1477,467,486]" gridrow="9" pageId="2" pageNumber="63">
<th id="0E555D9C335E006DFF0AFE42FE499792" box="[136,397,467,486]" gridcol="0" gridrow="9" pageId="2" pageNumber="63">
Dihydrodaphnodorin B (
<emphasis id="C1C0EAB0335EFF90FECCFE46FE9C9791" bold="true" box="[334,344,471,485]" pageId="2" pageNumber="63">8</emphasis>
)
</th>
<td id="0E555D9C335E006DFE19FE42FDD59792" box="[411,529,467,486]" gridcol="1" gridrow="9" pageId="2" pageNumber="63">95.35 ± 3.48</td>
<td id="0E555D9C335E006DFD9DFE42FD519792" box="[543,661,467,486]" gridcol="2" gridrow="9" pageId="2" pageNumber="63">81.66 ± 8.47</td>
<td id="0E555D9C335E006DFD21FE42FCCB9792" box="[675,783,467,486]" gridcol="3" gridrow="9" pageId="2" pageNumber="63">69.77 ± 4.25*</td>
<td id="0E555D9C335E006DFC9FFE42FC429792" box="[797,902,467,486]" gridcol="4" gridrow="9" pageId="2" pageNumber="63">67.08 ± 4.76</td>
<td id="0E555D9C335E006DFC16FE42FC399792" box="[916,1021,467,486]" gridcol="5" gridrow="9" pageId="2" pageNumber="63">62.00 ± 5.33*</td>
<td id="0E555D9C335E006DFB88FE42FBB79792" box="[1034,1139,467,486]" gridcol="6" gridrow="9" pageId="2" pageNumber="63">40.43 ± 7.82*</td>
<td id="0E555D9C335E006DFB03FE42FB2E9792" box="[1153,1258,467,486]" gridcol="7" gridrow="9" pageId="2" pageNumber="63">24.37 ± 4.82*</td>
<td id="0E555D9C335E006DFB75FE42FAA49792" box="[1271,1376,467,486]" gridcol="8" gridrow="9" pageId="2" pageNumber="63">9.53 ± 1.64*</td>
<td id="0E555D9C335E006DFAECFE42FA019792" box="[1390,1477,467,486]" gridcol="9" gridrow="9" pageId="2" pageNumber="63">27.3</td>
</tr>
</table>
</paragraph>
<paragraph id="F30B36A2335EFF90FFF3FE6FFF119424" blockId="2.[113,1500,507,593]" pageId="2" pageNumber="63">
<tableNote id="0E52372C335EFF90FFF3FE6FFF119424" pageId="2" pageNumber="63" targetBox="[136,1477,244,486]" targetPageId="2">
Seven-day-old
<taxonomicName id="34B44D21335EFF90FF69FE6CFEFA9478" box="[235,318,509,524]" class="Magnoliopsida" family="Brassicaceae" genus="Arabidopsis" kingdom="Plantae" order="Brassicales" pageId="2" pageNumber="63" phylum="Tracheophyta" rank="species" species="thaliana">
<emphasis id="C1C0EAB0335EFF90FF69FE6CFEFA9478" box="[235,318,509,524]" italics="true" pageId="2" pageNumber="63">A. thaliana</emphasis>
</taxonomicName>
Col-0 seedlings were treated with compounds
<emphasis id="C1C0EAB0335EFF90FD43FE6FFD1B9478" bold="true" box="[705,735,510,524]" pageId="2" pageNumber="63">18</emphasis>
at concentrations of 1.25, 2.5, 5, 10, 25, 50, 100 and 200 µg/mL for 7 days, respectively. Fresh weight of the seedlings was collected. Values in the table are presented as percentage of the mean compared to the control. SE is one standard error of the mean,
<emphasis id="C1C0EAB0335EFF90FA0DFD85FA5D9457" box="[1423,1433,532,547]" italics="true" pageId="2" pageNumber="63">n</emphasis>
= 4. The IC
<subScript id="6F3034E7335EFF90FF03FDA3FF549448" attach="left" box="[129,144,562,572]" fontSize="4" pageId="2" pageNumber="63">50</subScript>
values of the phytotoxic flavonoids were calculated using SPSS 16.0 software.
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<emphasis id="C1C0EAB0335EFF90FF13FDD3FF5E9425" box="[145,154,578,593]" italics="true" pageId="2" pageNumber="63">P</emphasis>
&lt;0.05.
</tableNote>
</paragraph>
<paragraph id="F30B36A2335EFF90FF13FC2AFE5E9255" blockId="2.[113,783,674,1643]" pageId="2" pageNumber="63">
In contrast, compound
<emphasis id="C1C0EAB0335EFF90FEF4FC2BFE4795B9" bold="true" box="[374,387,954,973]" pageId="2" pageNumber="63">4</emphasis>
showed only a slight inhibitory activity and compound
<emphasis id="C1C0EAB0335EFF90FE91FC47FEE4959D" bold="true" box="[275,288,982,1001]" pageId="2" pageNumber="63">5</emphasis>
inhibited the growth of
<taxonomicName id="34B44D21335EFF90FDA3FC44FD4E959D" box="[545,650,981,1001]" class="Magnoliopsida" family="Brassicaceae" genus="Arabidopsis" kingdom="Plantae" order="Brassicales" pageId="2" pageNumber="63" phylum="Tracheophyta" rank="species" species="thaliana">
<emphasis id="C1C0EAB0335EFF90FDA3FC44FD4E959D" box="[545,650,981,1001]" italics="true" pageId="2" pageNumber="63">A. thaliana</emphasis>
</taxonomicName>
only at high concentrations (
<emphasis id="C1C0EAB0335EFF90FE94FC63FEE89272" bold="true" box="[278,300,1010,1030]" italics="true" pageId="2" pageNumber="63">À</emphasis>
100 µg/mL). The phytotoxicity of all eight compounds was dose-dependent.
</paragraph>
<paragraph id="F30B36A2335EFF90FF13FBBBFD7C9374" blockId="2.[113,783,674,1643]" pageId="2" pageNumber="63">
Previous studies showed that neochamaejasmin B (
<emphasis id="C1C0EAB0335EFF90FD1AFBBBFD619249" bold="true" box="[664,677,1066,1085]" pageId="2" pageNumber="63">1</emphasis>
) inhibited cellular
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H-thymidine incorporation and subsequent proliferation of human prostate cancer LNCaP cells (
<bibRefCitation id="97254B53335EFF90FD8BFBF3FD679201" author="Liu, W. &amp; Cheung, F. W. K. &amp; Liu, B. P. L. &amp; Li, C. &amp; Ye, W. &amp; Che, C. T." box="[521,675,1122,1141]" pageId="2" pageNumber="63" pagination="842 - 846" refId="ref8527" refString="Liu, W., Cheung, F. W. K., Liu, B. P. L., Li, C., Ye, W., Che, C. T., 2008. Involvement of p 21 and FasL in induction of cell cycle arrest and apoptosis by neochamaejasmin A in human prostate LNCaP cancer cells. J. Nat. Prod. 71, 842 - 846." type="journal article" year="2008">Liu et al., 2008</bibRefCitation>
), and also had antifungal activity (
<bibRefCitation id="97254B53335EFF90FEEEFBEFFDDE92E4" author="Yang, G. &amp; Liao, Z. &amp; Xu, Z. &amp; Zhang, H. &amp; Chen, D." box="[364,538,1149,1169]" pageId="2" pageNumber="63" pagination="776 - 779" refId="ref9781" refString="Yang, G., Liao, Z., Xu, Z., Zhang, H., Chen, D., 2005. Antimitotic and antifungal C- 3 / C- 300 - biflavanones from Stellera chamaejasme. Chem. Pharm. Bull. 53, 776 - 779." type="journal article" year="2005">Yang et al., 2005</bibRefCitation>
). Genkwanol A (
<emphasis id="C1C0EAB0335EFF90FD4EFBECFD1D92E4" bold="true" box="[716,729,1149,1168]" pageId="2" pageNumber="63">6</emphasis>
) and daphnodorin B (
<emphasis id="C1C0EAB0335EFF90FEA4FB0BFEF792D9" bold="true" box="[294,307,1178,1197]" pageId="2" pageNumber="63">7</emphasis>
) exhibited OE- glucosidase inhibitory activity (
<bibRefCitation id="97254B53335EFF90FFF8FB24FEE092BC" author="Zhou, T. &amp; Zhang, S. &amp; Liu, S. &amp; Cong, H. &amp; Xuan, L." box="[122,292,1205,1225]" pageId="2" pageNumber="63" pagination="242 - 247" refId="ref10058" refString="Zhou, T., Zhang, S., Liu, S., Cong, H., Xuan, L., 2010. Daphnodorin dimers from Edgeworthia chrysantha with OE- glucosidase inhibitory activity. Phytochem. Lett. 3, 242 - 247." type="journal article" year="2010">Zhou et al., 2010</bibRefCitation>
) and antitumor activity (
<bibRefCitation id="97254B53335EFF90FDABFB24FCCF92BC" author="Sakaguchi, M. &amp; Yamamoto, D. &amp; Takai, S. &amp; Jin, D. &amp; Taniguchi, M. &amp; Baba, K. &amp; Miyazaki, M." box="[553,779,1205,1225]" pageId="2" pageNumber="63" pagination="831 - 836" refId="ref9276" refString="Sakaguchi, M., Yamamoto, D., Takai, S., Jin, D., Taniguchi, M., Baba, K., Miyazaki, M., 2001. Inhibitory mechanism of daphnodorins for human chymase. Biochem. Biophys. Res. Commun. 283, 831 - 836." type="journal article" year="2001">Sakaguchi et al., 2001</bibRefCitation>
;
<bibRefCitation id="97254B53335EFF90FFF3FB40FEFB9290" author="Zheng, W. &amp; Gao, X. &amp; Chen, C. &amp; Tan, R." box="[113,319,1233,1253]" pageId="2" pageNumber="63" pagination="117 - 127" refId="ref9888" refString="Zheng, W., Gao, X., Chen, C., Tan, R., 2007 a. Total flavonoids of Daphne genkwa root significantly inhibit the growth and metastasis of Lewis lung carcinoma in C 57 BL 6 mice. Int. Immunopharmacol. 7, 117 - 127." type="journal article" year="2007">Zheng et al., 2007a</bibRefCitation>
,b;
<bibRefCitation id="97254B53335EFF90FEDCFB40FDC79290" author="Shu, Q. &amp; Fu, Y. &amp; Liu, T. &amp; Yu, Y." box="[350,515,1233,1253]" pageId="2" pageNumber="63" pagination="2149 - 2150" refId="ref9335" refString="Shu, Q., Fu, Y., Liu, T., Yu, Y., 2009. Study on antitumor effect of the Daphne odora ' s extracts on SMMC- 7721 and MCF- 7 cells. Li. Med. Mater. Med. Res. 20, 2149 - 2150." type="journal article" year="2009">Shu et al., 2009</bibRefCitation>
). Daphnodorin B (
<emphasis id="C1C0EAB0335EFF90FD4BFB40FD129290" bold="true" box="[713,726,1233,1252]" pageId="2" pageNumber="63">7</emphasis>
) was moderately active against HIV-
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1
<emphasis id="C1C0EAB0335EFF90FE42FB7DFE179374" box="[448,467,1260,1280]" italics="true" pageId="2" pageNumber="63">in</emphasis>
</quantity>
vitro (
<bibRefCitation id="97254B53335EFF90FD94FB7FFD6E9374" author="Hu, K. &amp; Kobayashi, H. &amp; Dong, A. &amp; Iwasaki, S. &amp; Yao, X." box="[534,682,1261,1281]" pageId="2" pageNumber="63" pagination="564 - 567" refId="ref8035" refString="Hu, K., Kobayashi, H., Dong, A., Iwasaki, S., Yao, X., 2000. Antifungal, antimitotic and anti-HIV- 1 agents from the roots of Wikstroemia indica. Planta Med. 66, 564 - 567." type="journal article" year="2000">Hu et al., 2000</bibRefCitation>
).
</paragraph>
<paragraph id="F30B36A2335EFF90FF13FA9BFE65901F" blockId="2.[113,783,674,1643]" pageId="2" pageNumber="63">
<bibRefCitation id="97254B53335EFF90FF13FA9BFE959368" author="Parvez, M. M. &amp; Tomita-Yokotani, K. &amp; Fujii, Y. &amp; Konishi, T. &amp; Iwashina, T." box="[145,337,1289,1309]" pageId="2" pageNumber="63" pagination="631 - 635" refId="ref8857" refString="Parvez, M. M., Tomita-Yokotani, K., Fujii, Y., Konishi, T., Iwashina, T., 2004. Effects of quercetin and its seven derivatives on the growth of Arabidopsis thaliana and Neurospora crassa. Biochem. Syst. Ecol. 32, 631 - 635." type="journal article" year="2004">Parvez et al. (2004)</bibRefCitation>
showed that the presence of a methyl group in the flavonoid nucleus enhances growth inhibition on
<taxonomicName id="34B44D21335EFF90FD25FAB5FCCB934C" box="[679,783,1316,1336]" class="Magnoliopsida" family="Brassicaceae" genus="Arabidopsis" kingdom="Plantae" order="Brassicales" pageId="2" pageNumber="63" phylum="Tracheophyta" rank="species" species="thaliana">
<emphasis id="C1C0EAB0335EFF90FD25FAB5FCCB934C" box="[679,783,1316,1336]" italics="true" pageId="2" pageNumber="63">A. thaliana</emphasis>
</taxonomicName>
and
<taxonomicName id="34B44D21335EFF90FF1DFAD1FE949320" box="[159,336,1344,1364]" class="Sordariomycetes" family="Sordariaceae" genus="Neurospora" kingdom="Fungi" order="Sordariales" pageId="2" pageNumber="63" phylum="Ascomycota" rank="species" species="crassa">
<emphasis id="C1C0EAB0335EFF90FF1DFAD1FE949320" box="[159,336,1344,1364]" italics="true" pageId="2" pageNumber="63">Neurospora crassa</emphasis>
</taxonomicName>
. Our results are consistent with this report as compound
<emphasis id="C1C0EAB0335EFF90FE82FACCFEC99304" bold="true" box="[256,269,1373,1392]" pageId="2" pageNumber="63">3</emphasis>
was a strong inhibitor of
<taxonomicName id="34B44D21335EFF90FD94FACDFDBB9304" box="[534,639,1372,1392]" class="Magnoliopsida" family="Brassicaceae" genus="Arabidopsis" kingdom="Plantae" order="Brassicales" pageId="2" pageNumber="63" phylum="Tracheophyta" rank="species" species="thaliana">
<emphasis id="C1C0EAB0335EFF90FD94FACDFDBB9304" box="[534,639,1372,1392]" italics="true" pageId="2" pageNumber="63">A. thaliana</emphasis>
</taxonomicName>
development, but compound
<emphasis id="C1C0EAB0335EFF90FE97FAE8FEE693F8" bold="true" box="[277,290,1401,1420]" pageId="2" pageNumber="63">4</emphasis>
was not. However, compounds
<emphasis id="C1C0EAB0335EFF90FDFCFAE8FD4F93F8" bold="true" box="[638,651,1401,1420]" pageId="2" pageNumber="63">1</emphasis>
,
<emphasis id="C1C0EAB0335EFF90FD19FAE8FD6C93F8" bold="true" box="[667,680,1401,1420]" pageId="2" pageNumber="63">2</emphasis>
and
<emphasis id="C1C0EAB0335EFF90FD66FAE8FCCE93F8" bold="true" box="[740,778,1401,1420]" pageId="2" pageNumber="63">68</emphasis>
, which have no methyl groups, also arrested the growth of
<taxonomicName id="34B44D21335EFF90FD40FA02FEC693B7" class="Magnoliopsida" family="Brassicaceae" genus="Arabidopsis" kingdom="Plantae" order="Brassicales" pageId="2" pageNumber="63" phylum="Tracheophyta" rank="subSpecies" species="thaliana" subSpecies="seedlings">
<emphasis id="C1C0EAB0335EFF90FD40FA02FF5193B7" italics="true" pageId="2" pageNumber="63">A. thaliana</emphasis>
seedlings
</taxonomicName>
. Therefore, the number and location of methyl groups and/or other substituents such as hydroxyl groups may influence the phytotoxicity of these compounds. Compounds
<emphasis id="C1C0EAB0335EFF90FC80FA79FCCB938F" bold="true" box="[770,783,1512,1531]" pageId="2" pageNumber="63">1</emphasis>
and
<emphasis id="C1C0EAB0335EFF90FF20F995FF6B9063" bold="true" box="[162,175,1540,1559]" pageId="2" pageNumber="63">2</emphasis>
had strong phytotoxic activities on
<taxonomicName id="34B44D21335EFF90FDBBF992FCCB9063" box="[569,783,1539,1559]" class="Magnoliopsida" family="Brassicaceae" genus="Arabidopsis" kingdom="Plantae" order="Brassicales" pageId="2" pageNumber="63" phylum="Tracheophyta" rank="subSpecies" species="thaliana" subSpecies="seedlings">
<emphasis id="C1C0EAB0335EFF90FDBBF992FD629063" box="[569,678,1539,1559]" italics="true" pageId="2" pageNumber="63">A. thaliana</emphasis>
seedlings
</taxonomicName>
despite the stereochemical configuration difference of the hydrogen at the C-
<superScript id="04C19BEA335EFF90FF74F9ADFECD9032" attach="left" box="[246,265,1593,1615]" fontSize="5" pageId="2" pageNumber="63">200</superScript>
position (
<figureCitation id="6B8F2A27335EFF90FEF0F9ADFE6D903B" box="[370,425,1596,1615]" captionStart="Fig" captionStartId="1.[845,871,1594,1608]" captionTargetBox="[795,1463,734,1563]" captionTargetId="graphics-925@1.[923,1047,1408,1509]" captionTargetPageId="1" captionText="Fig. 2. Structures of phytotoxic flavonoids from roots of S. chamaejasme." figureDoi="http://doi.org/10.5281/zenodo.10489527" httpUri="https://zenodo.org/record/10489527/files/figure.png" pageId="2" pageNumber="63">Fig. 2</figureCitation>
), indicating that the spatial configuration is not a critical factor.
</paragraph>
</subSubSection>
</treatment>
</document>