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The Biological and Chemical Diversity of Tetramic Acid Compounds from Marine-Derived Microorganisms

Identifieur interne : 000A58 ( Pmc/Curation ); précédent : 000A57; suivant : 000A59

The Biological and Chemical Diversity of Tetramic Acid Compounds from Marine-Derived Microorganisms

Auteurs : Minghua Jiang [République populaire de Chine] ; Senhua Chen [République populaire de Chine] ; Jing Li [République populaire de Chine] ; Lan Liu [République populaire de Chine]

Source :

RBID : PMC:7074263

Abstract

Tetramic acid (pyrrolidine-2,4-dione) compounds, isolated from a variety of marine and terrestrial organisms, have attracted considerable attention for their diverse, challenging structural complexity and promising bioactivities. In the past decade, marine-derived microorganisms have become great repositories of novel tetramic acids. Here, we discuss the biological activities of 277 tetramic acids of eight classifications (simple 3-acyl tetramic acids, 3-oligoenoyltetramic acids, 3-decalinoyltetramic acid, 3-spirotetramic acids, macrocyclic tetramic acids, N-acylated tetramic acids, α-cyclopiazonic acid-type tetramic acids, and other tetramic acids) from marine-derived microbes, including fungi, actinobacteria, bacteria, and cyanobacteria, as reported in 195 research studies up to 2019.


Url:
DOI: 10.3390/md18020114
PubMed: 32075282
PubMed Central: 7074263

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PMC:7074263

Le document en format XML

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<p>Tetramic acid (pyrrolidine-2,4-dione) compounds, isolated from a variety of marine and terrestrial organisms, have attracted considerable attention for their diverse, challenging structural complexity and promising bioactivities. In the past decade, marine-derived microorganisms have become great repositories of novel tetramic acids. Here, we discuss the biological activities of 277 tetramic acids of eight classifications (simple 3-acyl tetramic acids, 3-oligoenoyltetramic acids, 3-decalinoyltetramic acid, 3-spirotetramic acids, macrocyclic tetramic acids,
<italic>N</italic>
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</TEI>
<pmc article-type="review-article">
<pmc-dir>properties open_access</pmc-dir>
<front>
<journal-meta>
<journal-id journal-id-type="nlm-ta">Mar Drugs</journal-id>
<journal-id journal-id-type="iso-abbrev">Mar Drugs</journal-id>
<journal-id journal-id-type="publisher-id">marinedrugs</journal-id>
<journal-title-group>
<journal-title>Marine Drugs</journal-title>
</journal-title-group>
<issn pub-type="epub">1660-3397</issn>
<publisher>
<publisher-name>MDPI</publisher-name>
</publisher>
</journal-meta>
<article-meta>
<article-id pub-id-type="pmid">32075282</article-id>
<article-id pub-id-type="pmc">7074263</article-id>
<article-id pub-id-type="doi">10.3390/md18020114</article-id>
<article-id pub-id-type="publisher-id">marinedrugs-18-00114</article-id>
<article-categories>
<subj-group subj-group-type="heading">
<subject>Review</subject>
</subj-group>
</article-categories>
<title-group>
<article-title>The Biological and Chemical Diversity of Tetramic Acid Compounds from Marine-Derived Microorganisms</article-title>
</title-group>
<contrib-group>
<contrib contrib-type="author">
<contrib-id contrib-id-type="orcid" authenticated="true">https://orcid.org/0000-0002-3036-3879</contrib-id>
<name>
<surname>Jiang</surname>
<given-names>Minghua</given-names>
</name>
<xref ref-type="aff" rid="af1-marinedrugs-18-00114">1</xref>
<xref ref-type="aff" rid="af2-marinedrugs-18-00114">2</xref>
<xref ref-type="author-notes" rid="fn1-marinedrugs-18-00114">†</xref>
</contrib>
<contrib contrib-type="author">
<contrib-id contrib-id-type="orcid" authenticated="true">https://orcid.org/0000-0002-5498-0206</contrib-id>
<name>
<surname>Chen</surname>
<given-names>Senhua</given-names>
</name>
<xref ref-type="aff" rid="af1-marinedrugs-18-00114">1</xref>
<xref ref-type="aff" rid="af2-marinedrugs-18-00114">2</xref>
<xref ref-type="aff" rid="af3-marinedrugs-18-00114">3</xref>
<xref rid="c1-marinedrugs-18-00114" ref-type="corresp">*</xref>
<xref ref-type="author-notes" rid="fn1-marinedrugs-18-00114">†</xref>
</contrib>
<contrib contrib-type="author">
<name>
<surname>Li</surname>
<given-names>Jing</given-names>
</name>
<xref ref-type="aff" rid="af1-marinedrugs-18-00114">1</xref>
<xref ref-type="aff" rid="af2-marinedrugs-18-00114">2</xref>
<xref ref-type="aff" rid="af3-marinedrugs-18-00114">3</xref>
</contrib>
<contrib contrib-type="author">
<contrib-id contrib-id-type="orcid" authenticated="true">https://orcid.org/0000-0003-2765-4015</contrib-id>
<name>
<surname>Liu</surname>
<given-names>Lan</given-names>
</name>
<xref ref-type="aff" rid="af1-marinedrugs-18-00114">1</xref>
<xref ref-type="aff" rid="af2-marinedrugs-18-00114">2</xref>
<xref ref-type="aff" rid="af3-marinedrugs-18-00114">3</xref>
<xref rid="c1-marinedrugs-18-00114" ref-type="corresp">*</xref>
</contrib>
</contrib-group>
<aff id="af1-marinedrugs-18-00114">
<label>1</label>
School of Marine Sciences, Sun Yat-sen University, Guangzhou 510006, China;
<email>jiangmh23@mail2.sysu.edu.cn</email>
(M.J.);
<email>lijing356@mail.sysu.edu.cn</email>
(J.L.)</aff>
<aff id="af2-marinedrugs-18-00114">
<label>2</label>
South China Sea Bio-Resource Exploitation and Utilization Collaborative Innovation Center, Guangzhou 510006, China</aff>
<aff id="af3-marinedrugs-18-00114">
<label>3</label>
Southern Laboratory of Ocean Science and Engineering (Guangdong, Zhuhai), Zhuhai 519000, China</aff>
<author-notes>
<corresp id="c1-marinedrugs-18-00114">
<label>*</label>
Correspondence:
<email>chensenh@mail.sysu.edu.cn</email>
(S.C.);
<email>cesllan@mail.sysu.edu.cn</email>
(L.L.); Tel.: +86-020-84725459 (S.C. & L.L.)</corresp>
<fn id="fn1-marinedrugs-18-00114">
<label>†</label>
<p>These authors contributed equally to this work.</p>
</fn>
</author-notes>
<pub-date pub-type="epub">
<day>15</day>
<month>2</month>
<year>2020</year>
</pub-date>
<pub-date pub-type="collection">
<month>2</month>
<year>2020</year>
</pub-date>
<volume>18</volume>
<issue>2</issue>
<elocation-id>114</elocation-id>
<history>
<date date-type="received">
<day>25</day>
<month>1</month>
<year>2020</year>
</date>
<date date-type="accepted">
<day>14</day>
<month>2</month>
<year>2020</year>
</date>
</history>
<permissions>
<copyright-statement>© 2020 by the authors.</copyright-statement>
<copyright-year>2020</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>Tetramic acid (pyrrolidine-2,4-dione) compounds, isolated from a variety of marine and terrestrial organisms, have attracted considerable attention for their diverse, challenging structural complexity and promising bioactivities. In the past decade, marine-derived microorganisms have become great repositories of novel tetramic acids. Here, we discuss the biological activities of 277 tetramic acids of eight classifications (simple 3-acyl tetramic acids, 3-oligoenoyltetramic acids, 3-decalinoyltetramic acid, 3-spirotetramic acids, macrocyclic tetramic acids,
<italic>N</italic>
-acylated tetramic acids, α-cyclopiazonic acid-type tetramic acids, and other tetramic acids) from marine-derived microbes, including fungi, actinobacteria, bacteria, and cyanobacteria, as reported in 195 research studies up to 2019.</p>
</abstract>
<kwd-group>
<kwd>tetramic acid</kwd>
<kwd>bioactivity</kwd>
<kwd>marine natural product</kwd>
<kwd>marine-derived microorganisms</kwd>
</kwd-group>
</article-meta>
</front>
<floats-group>
<fig id="marinedrugs-18-00114-f001" orientation="portrait" position="float">
<label>Figure 1</label>
<caption>
<p>Classification of the 277 tetramic acids (TAs) from marine microorganisms into eight classes. Some examples of typical molecules belonging to these classes are illustrated: simple 3-acyl-tetramic acids (penicillenol A
<sub>1</sub>
), 3-oligoenoyltetramic acids (tirandamycin A), 3-decalinoyltetramic acids (equisetin), 3-spirotetramic acids (pseurotin A), macrocyclic tetramic acids (from left to right, ikarugamycin, GKK1032A
<sub>2</sub>
),
<italic>N</italic>
-acylated tetramic acids (symplostatin 4), α-cyclopiazonic acid (CPA)-type tetramic acids (
<italic>α</italic>
-cyclopiazonic acid), and other tetramic acids (vermelhotin). The main characteristics of each chemical class are highlighted in red.</p>
</caption>
<graphic xlink:href="marinedrugs-18-00114-g001"></graphic>
</fig>
<fig id="marinedrugs-18-00114-f002" orientation="portrait" position="float">
<label>Figure 2</label>
<caption>
<p>Chemical structures of simple 3-acyl tetramic acids (
<bold>1</bold>
–
<bold>26</bold>
).</p>
</caption>
<graphic xlink:href="marinedrugs-18-00114-g002"></graphic>
</fig>
<fig id="marinedrugs-18-00114-f003" orientation="portrait" position="float">
<label>Figure 3</label>
<caption>
<p>Chemical structures of 3-oligoenoyltetramic acids (
<bold>27</bold>
–
<bold>39</bold>
).</p>
</caption>
<graphic xlink:href="marinedrugs-18-00114-g003"></graphic>
</fig>
<fig id="marinedrugs-18-00114-f004" orientation="portrait" position="float">
<label>Figure 4</label>
<caption>
<p>Chemical structures of 3-decalinoyltetramic acids (
<bold>40</bold>
–
<bold>74</bold>
).</p>
</caption>
<graphic xlink:href="marinedrugs-18-00114-g004a"></graphic>
<graphic xlink:href="marinedrugs-18-00114-g004b"></graphic>
</fig>
<fig id="marinedrugs-18-00114-f005" orientation="portrait" position="float">
<label>Figure 5</label>
<caption>
<p>Chemical structures of 3-spirotetramic acids (
<bold>75</bold>
–
<bold>108</bold>
).</p>
</caption>
<graphic xlink:href="marinedrugs-18-00114-g005a"></graphic>
<graphic xlink:href="marinedrugs-18-00114-g005b"></graphic>
</fig>
<fig id="marinedrugs-18-00114-f006" orientation="portrait" position="float">
<label>Figure 6</label>
<caption>
<p>Chemical structures of macrocyclic tetramic acids-polycyclic tetramate macrolactams (
<bold>109</bold>
–
<bold>146</bold>
).</p>
</caption>
<graphic xlink:href="marinedrugs-18-00114-g006a"></graphic>
<graphic xlink:href="marinedrugs-18-00114-g006b"></graphic>
</fig>
<fig id="marinedrugs-18-00114-f007" orientation="portrait" position="float">
<label>Figure 7</label>
<caption>
<p>Chemical structures of macrocyclic tetramic acids-pyrrocidine tetramate alkaloids (
<bold>147</bold>
–
<bold>165).</bold>
</p>
</caption>
<graphic xlink:href="marinedrugs-18-00114-g007"></graphic>
</fig>
<fig id="marinedrugs-18-00114-f008" orientation="portrait" position="float">
<label>Figure 8</label>
<caption>
<p>Chemical structures of
<italic>N</italic>
-acylated tetramic acids (
<bold>166</bold>
–
<bold>209</bold>
).</p>
</caption>
<graphic xlink:href="marinedrugs-18-00114-g008a"></graphic>
<graphic xlink:href="marinedrugs-18-00114-g008b"></graphic>
</fig>
<fig id="marinedrugs-18-00114-f009" orientation="portrait" position="float">
<label>Figure 9</label>
<caption>
<p>Chemical structures of CPA-type tetramic acids (
<bold>210</bold>
–
<bold>235).</bold>
</p>
</caption>
<graphic xlink:href="marinedrugs-18-00114-g009"></graphic>
</fig>
<fig id="marinedrugs-18-00114-f010" orientation="portrait" position="float">
<label>Figure 10</label>
<caption>
<p>Chemical structures of other tetramic acids (
<bold>236</bold>
–
<bold>277</bold>
).</p>
</caption>
<graphic xlink:href="marinedrugs-18-00114-g010a"></graphic>
<graphic xlink:href="marinedrugs-18-00114-g010b"></graphic>
</fig>
<fig id="marinedrugs-18-00114-f011" orientation="portrait" position="float">
<label>Figure 11</label>
<caption>
<p>(
<bold>a</bold>
) The tetramic acids (TAs) from marine microorganisms in this review divided by the origin of microorganisms, indicating that fungi are the dominant source. (
<bold>b</bold>
) The pie chart provides more in-depth insight into the fungi.</p>
</caption>
<graphic xlink:href="marinedrugs-18-00114-g011"></graphic>
</fig>
<fig id="marinedrugs-18-00114-f012" orientation="portrait" position="float">
<label>Figure 12</label>
<caption>
<p>The relationship between different chemical groups of TAs and their producer (marine microorganisms). This number corresponds to the number of TA compounds in different chemical classes.</p>
</caption>
<graphic xlink:href="marinedrugs-18-00114-g012"></graphic>
</fig>
<fig id="marinedrugs-18-00114-f013" orientation="portrait" position="float">
<label>Figure 13</label>
<caption>
<p>The TAs from marine microorganisms were divided by their sources (habitats); 277 TAs were isolated from 120 species of microorganisms in 120 habitats.</p>
</caption>
<graphic xlink:href="marinedrugs-18-00114-g013"></graphic>
</fig>
<fig id="marinedrugs-18-00114-f014" orientation="portrait" position="float">
<label>Figure 14</label>
<caption>
<p>The percentage represents the proportion of one activity compared to the whole occurrence of activities of 202 bioactive TAs from marine microorganisms (
<italic>n</italic>
= 327). Some compounds present various activities and are counted in more than one category.</p>
</caption>
<graphic xlink:href="marinedrugs-18-00114-g014"></graphic>
</fig>
<fig id="marinedrugs-18-00114-f015" orientation="portrait" position="float">
<label>Figure 15</label>
<caption>
<p>Classification of the 202 bioactive TAs according to their activities and chemical classes. The number of compounds is symbolized by the disc diameters for each bioactivity and each chemical class. The colors correspond to the different categories of the activity targets. Gray represents a mixed target; yellow mainly represents a cell line target, blue primarily represents the specific cellular mechanism, green represents the enzyme target, and purple represents the entire organism target.</p>
</caption>
<graphic xlink:href="marinedrugs-18-00114-g015"></graphic>
</fig>
</floats-group>
</pmc>
</record>

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