Diacetylcurcumin: Its Potential Antiarthritic Effect on a Freund’s Complete Adjuvant-Induced Murine Model
Identifieur interne : 000823 ( Ncbi/Merge ); précédent : 000822; suivant : 000824Diacetylcurcumin: Its Potential Antiarthritic Effect on a Freund’s Complete Adjuvant-Induced Murine Model
Auteurs : Carolina Escobedo-Martínez [Mexique] ; Silvia Laura Guzmán-Gutiérrez [Mexique] ; María Isabel Carrillo-L Pez [Mexique] ; Martha Alicia Deveze-Álvarez [Mexique] ; Alfonso Trujillo-Valdivia [Mexique] ; William Meza-Morales [Mexique] ; Raúl G. Enríquez [Mexique]Source :
- Molecules [ 1420-3049 ] ; 2019.
Abstract
The present study aims to evaluate the antiarthritic activity of diacetylcurcumin (DAC), a synthetic derivative where the free phenolic groups of curcumin are derivatized by acetylation, thereby conferring greater lipophilicity to the parent molecule and partially overcoming the limited systemic bioavailability of curcumin. Antiarthritic activity was evaluated on a Freund’s complete adjuvant (FCA)-induced murine model of arthritis. Oral administration of DAC (60 and 120 mg/kg) resulted in a significant inhibition of inflammation in the acute and chronic phases, respectively, demonstrating an improved and sustained anti-inflammatory effect, comparable to that of curcumin (150 mg/kg) in the chronic stage at a lower dose. Phenylbutazone (80 mg/kg) was used as a reference drug. The pharmacological consequence of DAC or curcumin treatment is the prevention of secondary lesions commonly associated with this biological model.
Url:
DOI: 10.3390/molecules24142643
PubMed: 31330908
PubMed Central: 6680498
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CP 36050</wicri:noRegion></affiliation></author><author><name sortKey="Deveze Lvarez, Martha Alicia" sort="Deveze Lvarez, Martha Alicia" uniqKey="Deveze Lvarez M" first="Martha Alicia" last="Deveze-Álvarez">Martha Alicia Deveze-Álvarez</name><affiliation wicri:level="1"><nlm:aff id="af1-molecules-24-02643">Departamento de Farmacia, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Campus Guanajuato, Guanajuato, Gto. CP 36050, Mexico</nlm:aff><country xml:lang="fr">Mexique</country><wicri:regionArea>Departamento de Farmacia, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Campus Guanajuato, Guanajuato, Gto. CP 36050</wicri:regionArea><wicri:noRegion>Gto. CP 36050</wicri:noRegion></affiliation></author><author><name sortKey="Trujillo Valdivia, Alfonso" sort="Trujillo Valdivia, Alfonso" uniqKey="Trujillo Valdivia A" first="Alfonso" last="Trujillo-Valdivia">Alfonso Trujillo-Valdivia</name><affiliation wicri:level="1"><nlm:aff id="af1-molecules-24-02643">Departamento de Farmacia, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Campus Guanajuato, Guanajuato, Gto. CP 36050, Mexico</nlm:aff><country xml:lang="fr">Mexique</country><wicri:regionArea>Departamento de Farmacia, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Campus Guanajuato, Guanajuato, Gto. CP 36050</wicri:regionArea><wicri:noRegion>Gto. CP 36050</wicri:noRegion></affiliation></author><author><name sortKey="Meza Morales, William" sort="Meza Morales, William" uniqKey="Meza Morales W" first="William" last="Meza-Morales">William Meza-Morales</name><affiliation wicri:level="1"><nlm:aff id="af3-molecules-24-02643">Instituto de Química, Universidad Nacional Autónoma de México, México, CDMX. CP 04510, Mexico</nlm:aff><country xml:lang="fr">Mexique</country><wicri:regionArea>Instituto de Química, Universidad Nacional Autónoma de México, México, CDMX. CP 04510</wicri:regionArea><wicri:noRegion>CDMX. CP 04510</wicri:noRegion></affiliation></author><author><name sortKey="Enriquez, Raul G" sort="Enriquez, Raul G" uniqKey="Enriquez R" first="Raúl G." last="Enríquez">Raúl G. Enríquez</name><affiliation wicri:level="1"><nlm:aff id="af3-molecules-24-02643">Instituto de Química, Universidad Nacional Autónoma de México, México, CDMX. CP 04510, Mexico</nlm:aff><country xml:lang="fr">Mexique</country><wicri:regionArea>Instituto de Química, Universidad Nacional Autónoma de México, México, CDMX. CP 04510</wicri:regionArea><wicri:noRegion>CDMX. CP 04510</wicri:noRegion></affiliation></author></analytic><series><title level="j">Molecules</title><idno type="eISSN">1420-3049</idno><imprint><date when="2019">2019</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>The present study aims to evaluate the antiarthritic activity of diacetylcurcumin (DAC), a synthetic derivative where the free phenolic groups of curcumin are derivatized by acetylation, thereby conferring greater lipophilicity to the parent molecule and partially overcoming the limited systemic bioavailability of curcumin. Antiarthritic activity was evaluated on a Freund’s complete adjuvant (FCA)-induced murine model of arthritis. Oral administration of DAC (60 and 120 mg/kg) resulted in a significant inhibition of inflammation in the acute and chronic phases, respectively, demonstrating an improved and sustained anti-inflammatory effect, comparable to that of curcumin (150 mg/kg) in the chronic stage at a lower dose. Phenylbutazone (80 mg/kg) was used as a reference drug. The pharmacological consequence of DAC or curcumin treatment is the prevention of secondary lesions commonly associated with this biological model.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Asteriou, E" uniqKey="Asteriou E">E. Asteriou</name></author><author><name sortKey="Gkoutzourelas, A" uniqKey="Gkoutzourelas A">A. Gkoutzourelas</name></author><author><name sortKey="Mavropoulos, A" uniqKey="Mavropoulos A">A. Mavropoulos</name></author><author><name sortKey="Katsiari, C" uniqKey="Katsiari C">C. Katsiari</name></author><author><name sortKey="Sakkas, L I" uniqKey="Sakkas L">L.I. 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<front><journal-meta><journal-id journal-id-type="nlm-ta">Molecules</journal-id><journal-id journal-id-type="iso-abbrev">Molecules</journal-id><journal-id journal-id-type="publisher-id">molecules</journal-id><journal-title-group><journal-title>Molecules</journal-title></journal-title-group><issn pub-type="epub">1420-3049</issn><publisher><publisher-name>MDPI</publisher-name></publisher></journal-meta><article-meta><article-id pub-id-type="pmid">31330908</article-id><article-id pub-id-type="pmc">6680498</article-id><article-id pub-id-type="doi">10.3390/molecules24142643</article-id><article-id pub-id-type="publisher-id">molecules-24-02643</article-id><article-categories><subj-group subj-group-type="heading"><subject>Article</subject></subj-group></article-categories><title-group><article-title>Diacetylcurcumin: Its Potential Antiarthritic Effect on a Freund’s Complete Adjuvant-Induced Murine Model</article-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Escobedo-Martínez</surname><given-names>Carolina</given-names></name><xref ref-type="aff" rid="af1-molecules-24-02643">1</xref><xref rid="c1-molecules-24-02643" ref-type="corresp">*</xref></contrib><contrib contrib-type="author"><name><surname>Guzmán-Gutiérrez</surname><given-names>Silvia Laura</given-names></name><xref ref-type="aff" rid="af2-molecules-24-02643">2</xref></contrib><contrib contrib-type="author"><name><surname>Carrillo-López</surname><given-names>María Isabel</given-names></name><xref ref-type="aff" rid="af1-molecules-24-02643">1</xref></contrib><contrib contrib-type="author"><name><surname>Deveze-Álvarez</surname><given-names>Martha Alicia</given-names></name><xref ref-type="aff" rid="af1-molecules-24-02643">1</xref></contrib><contrib contrib-type="author"><name><surname>Trujillo-Valdivia</surname><given-names>Alfonso</given-names></name><xref ref-type="aff" rid="af1-molecules-24-02643">1</xref></contrib><contrib contrib-type="author"><contrib-id contrib-id-type="orcid" authenticated="true">https://orcid.org/0000-0002-2759-4334</contrib-id><name><surname>Meza-Morales</surname><given-names>William</given-names></name><xref ref-type="aff" rid="af3-molecules-24-02643">3</xref></contrib><contrib contrib-type="author"><name><surname>Enríquez</surname><given-names>Raúl G.</given-names></name><xref ref-type="aff" rid="af3-molecules-24-02643">3</xref><xref rid="c1-molecules-24-02643" ref-type="corresp">*</xref></contrib></contrib-group><aff id="af1-molecules-24-02643"><label>1</label>Departamento de Farmacia, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Campus Guanajuato, Guanajuato, Gto. CP 36050, Mexico</aff><aff id="af2-molecules-24-02643"><label>2</label>CONACyT-Instituto de Investigaciones Biomédicas, Departamento de Inmunología, Universidad Nacional Autónoma de México, CDMX. CP 04510, Mexico</aff><aff id="af3-molecules-24-02643"><label>3</label>Instituto de Química, Universidad Nacional Autónoma de México, México, CDMX. CP 04510, Mexico</aff><author-notes><corresp id="c1-molecules-24-02643"><label>*</label>Correspondence: <email>c.escobedo@ugto.mx</email> (C.E.-M.); <email>enriquezhabib@gmail.com</email> (R.G.E.); Tel.: +52-473-732-0006 (ext. 5415) (C.E.-M.); +52-555-622-4404 (R.G.E.)</corresp></author-notes><pub-date pub-type="epub"><day>21</day><month>7</month><year>2019</year></pub-date><pub-date pub-type="collection"><month>7</month><year>2019</year></pub-date><volume>24</volume><issue>14</issue><elocation-id>2643</elocation-id><history><date date-type="received"><day>25</day><month>6</month><year>2019</year></date><date date-type="accepted"><day>20</day><month>7</month><year>2019</year></date></history><permissions><copyright-statement>© 2019 by the authors.</copyright-statement><copyright-year>2019</copyright-year><license license-type="open-access"><license-p>Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (<ext-link ext-link-type="uri" xlink:href="http://creativecommons.org/licenses/by/4.0/">http://creativecommons.org/licenses/by/4.0/</ext-link>).</license-p></license></permissions><abstract><p>The present study aims to evaluate the antiarthritic activity of diacetylcurcumin (DAC), a synthetic derivative where the free phenolic groups of curcumin are derivatized by acetylation, thereby conferring greater lipophilicity to the parent molecule and partially overcoming the limited systemic bioavailability of curcumin. Antiarthritic activity was evaluated on a Freund’s complete adjuvant (FCA)-induced murine model of arthritis. Oral administration of DAC (60 and 120 mg/kg) resulted in a significant inhibition of inflammation in the acute and chronic phases, respectively, demonstrating an improved and sustained anti-inflammatory effect, comparable to that of curcumin (150 mg/kg) in the chronic stage at a lower dose. Phenylbutazone (80 mg/kg) was used as a reference drug. The pharmacological consequence of DAC or curcumin treatment is the prevention of secondary lesions commonly associated with this biological model.</p></abstract><kwd-group><kwd>diacetylcurcumin</kwd><kwd>curcumin</kwd><kwd>Freund’s complete adjuvant</kwd><kwd>antiarthritic</kwd></kwd-group></article-meta></front><floats-group><fig id="molecules-24-02643-f001" orientation="portrait" position="float"><label>Figure 1</label><caption><p>Acute effect of the oral administration of phenylbutazone (80 mg/kg), (<bold>A</bold>) curcumin, and (<bold>B</bold>) diacetylcurcumin (DAC) (60, 120, and 150 mg/kg) on the edema produced by intradermal injection of Freund’s complete adjuvant into the footpad of right rear limbs of Wistar rats. Each bar represents the mean ± SEM (<italic>n</italic> = 5). ANOVA followed by Tukey’s test. <italic>p</italic> < 0.05, 0.01 and 0.001 (*, ** and *** respectively).</p></caption><graphic xlink:href="molecules-24-02643-g001"></graphic></fig><fig id="molecules-24-02643-f002" orientation="portrait" position="float"><label>Figure 2</label><caption><p>Antiinflammatory effect during the chronic phase of the oral administration of phenylbutazone (80 mg/kg), (<bold>A</bold>) curcumin, and (<bold>B</bold>) diacetylcurcumin (DAC) (60, 120, and 150 mg/kg) upon the edema induced by intradermal injection of Freund’s complete adjuvant into the footpad of right rear limbs of Wistar rats. Each point represents the mean ± SEM (<italic>n</italic> = 5). ANOVA followed by Tukey’s test. <italic>p</italic> < 0.05, 0.01 and 0.001 (*, ** and *** respectively).</p></caption><graphic xlink:href="molecules-24-02643-g002"></graphic></fig><fig id="molecules-24-02643-f003" orientation="portrait" position="float"><label>Figure 3</label><caption><p>Edema status after oral treatment (on day 25) with curcumin at different doses. (<bold>A</bold>) Vehicle, (<bold>B</bold>) Curcumin 60 mg/kg, (<bold>C</bold>) Curcumin 120 mg/kg, (<bold>D</bold>) Curcumin 150 mg/kg, and Phenylbutazone (80 mg/kg) (<bold>E</bold>).</p></caption><graphic xlink:href="molecules-24-02643-g003"></graphic></fig><fig id="molecules-24-02643-f004" orientation="portrait" position="float"><label>Figure 4</label><caption><p>Edema status after oral treatment (on day 25) with diacetylcurcumin (DAC) at different doses. (<bold>A</bold>) Vehicle, (<bold>B</bold>) DAC 60 mg/kg, (<bold>C</bold>) DAC 120 mg/kg, (<bold>D</bold>) DAC 150 mg/kg and Phenylbutazone (80 mg/kg) (<bold>E</bold>).</p></caption><graphic xlink:href="molecules-24-02643-g004"></graphic></fig><fig id="molecules-24-02643-f005" orientation="portrait" position="float"><label>Figure 5</label><caption><p>Chromatogram of the curcumin (1) (t<sub>R</sub> = 4.873 min) sample, injected at a concentration of 0.25 mg/mL, with detection at a wavelength of 265 nm.</p></caption><graphic xlink:href="molecules-24-02643-g005"></graphic></fig><fig id="molecules-24-02643-f006" orientation="portrait" position="float"><label>Figure 6</label><caption><p>Chromatogram of diacetylcurcumin (2) (t<sub>R</sub> = 9.190 min) samples, injected at a concentration of 0.25 mg/mL, with detection at a wavelength of 257 nm.</p></caption><graphic xlink:href="molecules-24-02643-g006"></graphic></fig><table-wrap id="molecules-24-02643-t001" orientation="portrait" position="float"><object-id pub-id-type="pii">molecules-24-02643-t001_Table 1</object-id><label>Table 1</label><caption><p><sup>1</sup>H-NMR spectral data of curcumin and diacetylcurcumin (DAC) (500 MHz) <sup>a</sup>.</p></caption><table frame="hsides" rules="groups"><thead><tr><th rowspan="2" align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" colspan="1"><sup>1</sup>H <sup>a</sup></th><th colspan="4" align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1">Curcumin</th><th colspan="4" align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1">Diacetylcurcumin</th></tr><tr><th align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Chemical Shift</th><th align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Multiplicity</th><th align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Integral</th><th align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Coupling Constant (Hz)</th><th align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Chemical Shift</th><th align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Multiplicity</th><th align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Integral</th><th align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Coupling Constant (Hz)</th></tr></thead><tbody><tr><td align="center" valign="middle" rowspan="1" colspan="1">CH<sub>3</sub>-2‴</td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1">s</td><td align="center" valign="middle" rowspan="1" colspan="1">6</td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1">2.33</td><td align="center" valign="middle" rowspan="1" colspan="1">s</td><td align="center" valign="middle" rowspan="1" colspan="1">6</td><td align="center" valign="middle" rowspan="1" colspan="1"></td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1">CH<sub>3</sub>-2″</td><td align="center" valign="middle" rowspan="1" colspan="1">3.93</td><td align="center" valign="middle" rowspan="1" colspan="1">s</td><td align="center" valign="middle" rowspan="1" colspan="1">6</td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1">3.88</td><td align="center" valign="middle" rowspan="1" colspan="1">s</td><td align="center" valign="middle" rowspan="1" colspan="1">6</td><td align="center" valign="middle" rowspan="1" colspan="1"></td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1">H-4</td><td align="center" valign="middle" rowspan="1" colspan="1">5.82</td><td align="center" valign="middle" rowspan="1" colspan="1">s</td><td align="center" valign="middle" rowspan="1" colspan="1">1</td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1">5.85</td><td align="center" valign="middle" rowspan="1" colspan="1">s</td><td align="center" valign="middle" rowspan="1" colspan="1">1</td><td align="center" valign="middle" rowspan="1" colspan="1"></td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1">H-2/H-6</td><td align="center" valign="middle" rowspan="1" colspan="1">6.48</td><td align="center" valign="middle" rowspan="1" colspan="1">d</td><td align="center" valign="middle" rowspan="1" colspan="1">2</td><td align="center" valign="middle" rowspan="1" colspan="1"><italic>J</italic> = 15.72</td><td align="center" valign="middle" rowspan="1" colspan="1">6.56</td><td align="center" valign="middle" rowspan="1" colspan="1">d</td><td align="center" valign="middle" rowspan="1" colspan="1">2</td><td align="center" valign="middle" rowspan="1" colspan="1"><italic>J</italic> = 15.86</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1">H-5′</td><td align="center" valign="middle" rowspan="1" colspan="1">6.91</td><td align="center" valign="middle" rowspan="1" colspan="1">d</td><td align="center" valign="middle" rowspan="1" colspan="1">2</td><td align="center" valign="middle" rowspan="1" colspan="1"><italic>J</italic> = 8.01</td><td align="center" valign="middle" rowspan="1" colspan="1">7.06</td><td align="center" valign="middle" rowspan="1" colspan="1">d</td><td align="center" valign="middle" rowspan="1" colspan="1">2</td><td align="center" valign="middle" rowspan="1" colspan="1"><italic>J</italic> = 8.11</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1">H-2’/H-6′</td><td align="center" valign="middle" rowspan="1" colspan="1">7.07</td><td align="center" valign="middle" rowspan="1" colspan="1">m</td><td align="center" valign="middle" rowspan="1" colspan="1">4</td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1"></td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1">H-2′</td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1">7.12</td><td align="center" valign="middle" rowspan="1" colspan="1">d</td><td align="center" valign="middle" rowspan="1" colspan="1">2</td><td align="center" valign="middle" rowspan="1" colspan="1"><italic>J</italic> = 1.81</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1">H-6′</td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1">7.15</td><td align="center" valign="middle" rowspan="1" colspan="1">dd</td><td align="center" valign="middle" rowspan="1" colspan="1">2</td><td align="center" valign="middle" rowspan="1" colspan="1"><italic>J</italic> = 8.15, 1.82</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1">H-1/H-7</td><td align="center" valign="middle" rowspan="1" colspan="1">7.57</td><td align="center" valign="middle" rowspan="1" colspan="1">d</td><td align="center" valign="middle" rowspan="1" colspan="1">2</td><td align="center" valign="middle" rowspan="1" colspan="1"><italic>J</italic> = 15.72</td><td align="center" valign="middle" rowspan="1" colspan="1">7.61</td><td align="center" valign="middle" rowspan="1" colspan="1">d</td><td align="center" valign="middle" rowspan="1" colspan="1">2</td><td align="center" valign="middle" rowspan="1" colspan="1"><italic>J</italic> = 15.78</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1">O-H<sub>aryl</sub></td><td align="center" valign="middle" rowspan="1" colspan="1">8.04</td><td align="center" valign="middle" rowspan="1" colspan="1">Wide signal</td><td align="center" valign="middle" rowspan="1" colspan="1">2</td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1"></td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">O-H</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">16.11</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Wide signal</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">1</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">15.85</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Wide signal</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">1</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"></td></tr></tbody></table><table-wrap-foot><fn><p><sup>a</sup> Data recorded in CDCl<sub>3</sub>. Chemical shifts (δ) are expressed in ppm with respect to tetramethylsilane (TMS). Assigned coupling patterns: s = singlet, d = doublet, dd = doublet of doublets, m = multiplet. All assignments were derived from experiments: <sup>1</sup>H-<sup>1</sup>H, <sup>13</sup>C-<sup>1</sup>H, HSQC (heteronuclear single quantum coherence; couplings <sup>1</sup>H-<sup>13</sup>C to a bond) and HMBC (heteronuclear multiple bond correlation; couplings <sup>1</sup>H-<sup>13</sup>C to 2 and 3 bonds). See <xref ref-type="app" rid="app1-molecules-24-02643">Supplementary Material</xref>.</p></fn></table-wrap-foot></table-wrap><table-wrap id="molecules-24-02643-t002" orientation="portrait" position="float"><object-id pub-id-type="pii">molecules-24-02643-t002_Table 2</object-id><label>Table 2</label><caption><p><sup>13</sup>C-NMR spectral data of curcumin and diacetylcurcumin (DAC) (125.7 MHz) <sup>a</sup>.</p></caption><table frame="hsides" rules="groups"><thead><tr><th rowspan="2" align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" colspan="1">Carbon <sup>a</sup></th><th colspan="2" align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1">Chemical Shift</th></tr><tr><th align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Curcumin</th><th align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Diacetylcurcumin</th></tr></thead><tbody><tr><td align="center" valign="middle" rowspan="1" colspan="1">C-2‴</td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1">20.87</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1">C-2″</td><td align="center" valign="middle" rowspan="1" colspan="1">55.42</td><td align="center" valign="middle" rowspan="1" colspan="1">56.11</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1">C-4</td><td align="center" valign="middle" rowspan="1" colspan="1">100.62</td><td align="center" valign="middle" rowspan="1" colspan="1">102.01</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1">C-2′</td><td align="center" valign="middle" rowspan="1" colspan="1">109.66</td><td align="center" valign="middle" rowspan="1" colspan="1">111.63</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1">C-5′</td><td align="center" valign="middle" rowspan="1" colspan="1">114.99</td><td align="center" valign="middle" rowspan="1" colspan="1">123.48</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1">C-2 and C-6</td><td align="center" valign="middle" rowspan="1" colspan="1">120.75</td><td align="center" valign="middle" rowspan="1" colspan="1">124.45</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1">C-6′</td><td align="center" valign="middle" rowspan="1" colspan="1">122.40</td><td align="center" valign="middle" rowspan="1" colspan="1">121.27</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1">C-1′</td><td align="center" valign="middle" rowspan="1" colspan="1">126.55</td><td align="center" valign="middle" rowspan="1" colspan="1">134.15</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1">C-1 and C-7</td><td align="center" valign="middle" rowspan="1" colspan="1">140.17</td><td align="center" valign="middle" rowspan="1" colspan="1">140.14</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1">C-4′</td><td align="center" valign="middle" rowspan="1" colspan="1">147.12</td><td align="center" valign="middle" rowspan="1" colspan="1">141.49</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1">C-3′</td><td align="center" valign="middle" rowspan="1" colspan="1">148.31</td><td align="center" valign="middle" rowspan="1" colspan="1">151.59</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1">C-1‴</td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1">169.00</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">C-3 and C-5</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">182.76</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">183.28</td></tr></tbody></table><table-wrap-foot><fn><p><sup>a</sup> Data recorded in CDCl<sub>3</sub>. Chemical shifts (δ) are expressed in ppm with respect to tetramethylsilane (TMS). All assignments were derived from experiments: <sup>1</sup>H-<sup>1</sup>H, <sup>13</sup>C-<sup>1</sup>H, HSQC (heteronuclear single quantum coherence; couplings <sup>1</sup>H-<sup>13</sup>C to a bond) and HMBC (heteronuclear multiple bond correlation; couplings <sup>1</sup>H-<sup>13</sup>C to 2 and 3 bonds) 2D NMR spectra. See <xref ref-type="app" rid="app1-molecules-24-02643">Supplementary Material</xref>.</p></fn></table-wrap-foot></table-wrap></floats-group></pmc><affiliations><list><country><li>Mexique</li></country></list><tree><country name="Mexique"><noRegion><name sortKey="Escobedo Martinez, Carolina" sort="Escobedo Martinez, Carolina" uniqKey="Escobedo Martinez C" first="Carolina" last="Escobedo-Martínez">Carolina Escobedo-Martínez</name></noRegion><name sortKey="Carrillo L Pez, Maria Isabel" sort="Carrillo L Pez, Maria Isabel" uniqKey="Carrillo L Pez M" first="María Isabel" last="Carrillo-L Pez">María Isabel Carrillo-L Pez</name><name sortKey="Deveze Lvarez, Martha Alicia" sort="Deveze Lvarez, Martha Alicia" uniqKey="Deveze Lvarez M" first="Martha Alicia" last="Deveze-Álvarez">Martha Alicia Deveze-Álvarez</name><name sortKey="Enriquez, Raul G" sort="Enriquez, Raul G" uniqKey="Enriquez R" first="Raúl G." last="Enríquez">Raúl G. Enríquez</name><name sortKey="Guzman Gutierrez, Silvia Laura" sort="Guzman Gutierrez, Silvia Laura" uniqKey="Guzman Gutierrez S" first="Silvia Laura" last="Guzmán-Gutiérrez">Silvia Laura Guzmán-Gutiérrez</name><name sortKey="Meza Morales, William" sort="Meza Morales, William" uniqKey="Meza Morales W" first="William" last="Meza-Morales">William Meza-Morales</name><name sortKey="Trujillo Valdivia, Alfonso" sort="Trujillo Valdivia, Alfonso" uniqKey="Trujillo Valdivia A" first="Alfonso" last="Trujillo-Valdivia">Alfonso Trujillo-Valdivia</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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