PhytophthoraV1, Main, Exploration, bibRecord, 000715

New Crambescidin-Type Alkaloids from the Indonesian Marine Sponge Clathria bulbotoxa.

Identifieur interne : 000715 ( Main/Exploration ); précédent : 000714; suivant : 000716

New Crambescidin-Type Alkaloids from the Indonesian Marine Sponge Clathria bulbotoxa.

Auteurs : Kasmiati Kasmiati [Japon, Indonésie] ; Yukio Yoshioka [Japon] ; Tetsuji Okamoto [Japon] ; Makoto Ojika [Japon]

Source :

Marine drugs [ 1660-3397 ] ; 2018.

RBID : pubmed:29518039

Descripteurs français

KwdFr :
- Alcaloïdes (composition chimique), Alcaloïdes (isolement et purification), Alcaloïdes (toxicité), Animaux (MeSH), Concentration inhibitrice 50 (MeSH), Guanidines (composition chimique), Humains (MeSH), Indonésie (MeSH), Lignée cellulaire tumorale (MeSH), Phytophthora (effets des médicaments et des substances chimiques), Porifera (composition chimique), Spiranes (composition chimique), Spiranes (isolement et purification), Spiranes (toxicité), Structure moléculaire (MeSH).
MESH :
- composition chimique : Alcaloïdes, Guanidines, Porifera, Spiranes.
- effets des médicaments et des substances chimiques : Phytophthora.
- isolement et purification : Alcaloïdes, Spiranes.
- toxicité : Alcaloïdes, Spiranes.
- Animaux, Concentration inhibitrice 50, Humains, Indonésie, Lignée cellulaire tumorale, Structure moléculaire.

English descriptors

KwdEn :
- Alkaloids (chemistry), Alkaloids (isolation & purification), Alkaloids (toxicity), Animals (MeSH), Cell Line, Tumor (MeSH), Guanidines (chemistry), Humans (MeSH), Indonesia (MeSH), Inhibitory Concentration 50 (MeSH), Molecular Structure (MeSH), Phytophthora (drug effects), Porifera (chemistry), Spiro Compounds (chemistry), Spiro Compounds (isolation & purification), Spiro Compounds (toxicity).
MESH :
- chemical , chemistry : Alkaloids, Guanidines, Spiro Compounds.
- chemical , isolation & purification : Alkaloids, Spiro Compounds.
- chemical , toxicity : Alkaloids, Spiro Compounds.
- chemistry : Porifera.
- drug effects : Phytophthora.
- Animals, Cell Line, Tumor, Humans, Indonesia, Inhibitory Concentration 50, Molecular Structure.

Abstract

A crude methanolic extract of the Indonesian sponge Clathria bulbotoxa showed a potent cytotoxic activity against the human epidermoid carcinoma A431 cells. An investigation of the active components led to the isolation of three new compounds named crambescidins 345 (1), 361 (2), and 373 (3), together with the known related metabolites crambescidins 359 (4), 657 (5), and 800 (6). The structures of the compounds were determined by spectroscopic analysis. These compounds 1-4 that possess a simple pentacyclic guanidine core exhibited moderate cytotoxicity against the A431 cells with the IC₅₀ values of 7.0, 2.5, 0.94, and 3.1 μM, respectively, while the known compounds 5 and 6 that possess a long aliphatic side chain were found to be significantly cytotoxic. On the other hand, in an anti-oomycete activity test against the fungus-like plant pathogen Phytophthora capsici, 1-4 showed a higher activity than that of 5 and 6, suggesting that the long aliphatic side chain plays a significant role for cytotoxicity, but is not effective or suppressive for anti-oomycete activity.

DOI: 10.3390/md16030084
PubMed: 29518039
PubMed Central: PMC5867628

Affiliations:

Indonésie, Japon

Links toward previous steps (curation, corpus...)

to stream Main, to step Corpus: 000811
to stream Main, to step Curation: 000811

Le document en format XML

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<term>Alkaloids (isolation & purification)</term>
<term>Alkaloids (toxicity)</term>
<term>Animals (MeSH)</term>
<term>Cell Line, Tumor (MeSH)</term>
<term>Guanidines (chemistry)</term>
<term>Humans (MeSH)</term>
<term>Indonesia (MeSH)</term>
<term>Inhibitory Concentration 50 (MeSH)</term>
<term>Molecular Structure (MeSH)</term>
<term>Phytophthora (drug effects)</term>
<term>Porifera (chemistry)</term>
<term>Spiro Compounds (chemistry)</term>
<term>Spiro Compounds (isolation & purification)</term>
<term>Spiro Compounds (toxicity)</term>
</keywords>
<keywords scheme="KwdFr" xml:lang="fr"><term>Alcaloïdes (composition chimique)</term>
<term>Alcaloïdes (isolement et purification)</term>
<term>Alcaloïdes (toxicité)</term>
<term>Animaux (MeSH)</term>
<term>Concentration inhibitrice 50 (MeSH)</term>
<term>Guanidines (composition chimique)</term>
<term>Humains (MeSH)</term>
<term>Indonésie (MeSH)</term>
<term>Lignée cellulaire tumorale (MeSH)</term>
<term>Phytophthora (effets des médicaments et des substances chimiques)</term>
<term>Porifera (composition chimique)</term>
<term>Spiranes (composition chimique)</term>
<term>Spiranes (isolement et purification)</term>
<term>Spiranes (toxicité)</term>
<term>Structure moléculaire (MeSH)</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Alkaloids</term>
<term>Guanidines</term>
<term>Spiro Compounds</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="isolation & purification" xml:lang="en"><term>Alkaloids</term>
<term>Spiro Compounds</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="toxicity" xml:lang="en"><term>Alkaloids</term>
<term>Spiro Compounds</term>
</keywords>
<keywords scheme="MESH" qualifier="chemistry" xml:lang="en"><term>Porifera</term>
</keywords>
<keywords scheme="MESH" qualifier="composition chimique" xml:lang="fr"><term>Alcaloïdes</term>
<term>Guanidines</term>
<term>Porifera</term>
<term>Spiranes</term>
</keywords>
<keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Phytophthora</term>
</keywords>
<keywords scheme="MESH" qualifier="effets des médicaments et des substances chimiques" xml:lang="fr"><term>Phytophthora</term>
</keywords>
<keywords scheme="MESH" qualifier="isolement et purification" xml:lang="fr"><term>Alcaloïdes</term>
<term>Spiranes</term>
</keywords>
<keywords scheme="MESH" qualifier="toxicité" xml:lang="fr"><term>Alcaloïdes</term>
<term>Spiranes</term>
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<term>Cell Line, Tumor</term>
<term>Humans</term>
<term>Indonesia</term>
<term>Inhibitory Concentration 50</term>
<term>Molecular Structure</term>
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<keywords scheme="MESH" xml:lang="fr"><term>Animaux</term>
<term>Concentration inhibitrice 50</term>
<term>Humains</term>
<term>Indonésie</term>
<term>Lignée cellulaire tumorale</term>
<term>Structure moléculaire</term>
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<front><div type="abstract" xml:lang="en">A crude methanolic extract of the Indonesian sponge <i>Clathria bulbotoxa</i>
 showed a potent cytotoxic activity against the human epidermoid carcinoma A431 cells. An investigation of the active components led to the isolation of three new compounds named crambescidins 345 (<b>1</b>
), 361 (<b>2</b>
), and 373 (<b>3</b>
), together with the known related metabolites crambescidins 359 (<b>4</b>
), 657 (<b>5</b>
), and 800 (<b>6</b>
). The structures of the compounds were determined by spectroscopic analysis. These compounds <b>1</b>
-<b>4</b>
 that possess a simple pentacyclic guanidine core exhibited moderate cytotoxicity against the A431 cells with the IC<sub>50</sub>
 values of 7.0, 2.5, 0.94, and 3.1 μM, respectively, while the known compounds <b>5</b>
 and <b>6</b>
 that possess a long aliphatic side chain were found to be significantly cytotoxic. On the other hand, in an anti-oomycete activity test against the fungus-like plant pathogen <i>Phytophthora capsici</i>
, <b>1</b>
-<b>4</b>
 showed a higher activity than that of <b>5</b>
 and <b>6</b>
, suggesting that the long aliphatic side chain plays a significant role for cytotoxicity, but is not effective or suppressive for anti-oomycete activity.</div>
</front>
</TEI>
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<DateCompleted><Year>2018</Year>
<Month>10</Month>
<Day>01</Day>
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<DateRevised><Year>2018</Year>
<Month>11</Month>
<Day>14</Day>
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<Issue>3</Issue>
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<Month>Mar</Month>
<Day>08</Day>
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<Title>Marine drugs</Title>
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</Journal>
<ArticleTitle>New Crambescidin-Type Alkaloids from the Indonesian Marine Sponge Clathria bulbotoxa.</ArticleTitle>
<ELocationID EIdType="pii" ValidYN="Y">E84</ELocationID>
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<Abstract><AbstractText>A crude methanolic extract of the Indonesian sponge <i>Clathria bulbotoxa</i>
 showed a potent cytotoxic activity against the human epidermoid carcinoma A431 cells. An investigation of the active components led to the isolation of three new compounds named crambescidins 345 (<b>1</b>
), 361 (<b>2</b>
), and 373 (<b>3</b>
), together with the known related metabolites crambescidins 359 (<b>4</b>
), 657 (<b>5</b>
), and 800 (<b>6</b>
). The structures of the compounds were determined by spectroscopic analysis. These compounds <b>1</b>
-<b>4</b>
 that possess a simple pentacyclic guanidine core exhibited moderate cytotoxicity against the A431 cells with the IC<sub>50</sub>
 values of 7.0, 2.5, 0.94, and 3.1 μM, respectively, while the known compounds <b>5</b>
 and <b>6</b>
 that possess a long aliphatic side chain were found to be significantly cytotoxic. On the other hand, in an anti-oomycete activity test against the fungus-like plant pathogen <i>Phytophthora capsici</i>
, <b>1</b>
-<b>4</b>
 showed a higher activity than that of <b>5</b>
 and <b>6</b>
, suggesting that the long aliphatic side chain plays a significant role for cytotoxicity, but is not effective or suppressive for anti-oomycete activity.</AbstractText>
</Abstract>
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<Initials>K</Initials>
<AffiliationInfo><Affiliation>Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa-ku, Nagoya 464-8601, Japan. kasmiati74@yahoo.com.</Affiliation>
</AffiliationInfo>
<AffiliationInfo><Affiliation>Faculty of Marine Science and Fishery, Hasanuddin University, Jalan Perintis Kemerdekaan KM. 10, Makassar 90245, Indonesia. kasmiati74@yahoo.com.</Affiliation>
</AffiliationInfo>
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<Author ValidYN="Y"><LastName>Yoshioka</LastName>
<ForeName>Yukio</ForeName>
<Initials>Y</Initials>
<AffiliationInfo><Affiliation>Graduate School of Biomedical and Health Sciences, Hiroshima University, Minami-ku, Hiroshima 734-8553, Japan. yyosioka@hiroshima-u.ac.jp.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Okamoto</LastName>
<ForeName>Tetsuji</ForeName>
<Initials>T</Initials>
<AffiliationInfo><Affiliation>Graduate School of Biomedical and Health Sciences, Hiroshima University, Minami-ku, Hiroshima 734-8553, Japan. tetsuok@hiroshima-u.ac.jp.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Ojika</LastName>
<ForeName>Makoto</ForeName>
<Initials>M</Initials>
<Identifier Source="ORCID">0000-0002-6671-8598</Identifier>
<AffiliationInfo><Affiliation>Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa-ku, Nagoya 464-8601, Japan. ojika@agr.nagoya-u.ac.jp.</Affiliation>
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<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D006801" MajorTopicYN="N">Humans</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D007214" MajorTopicYN="N">Indonesia</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D020128" MajorTopicYN="N">Inhibitory Concentration 50</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D015394" MajorTopicYN="N">Molecular Structure</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D010838" MajorTopicYN="N">Phytophthora</DescriptorName>
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</MeshHeading>
<MeshHeading><DescriptorName UI="D011161" MajorTopicYN="N">Porifera</DescriptorName>
<QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D013141" MajorTopicYN="N">Spiro Compounds</DescriptorName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
<QualifierName UI="Q000302" MajorTopicYN="N">isolation & purification</QualifierName>
<QualifierName UI="Q000633" MajorTopicYN="Y">toxicity</QualifierName>
</MeshHeading>
</MeshHeadingList>
<KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">Clathria bulbotoxa</Keyword>
<Keyword MajorTopicYN="N">Indonesian sponge</Keyword>
<Keyword MajorTopicYN="N">anti-oomycete activity</Keyword>
<Keyword MajorTopicYN="N">crambescidin</Keyword>
<Keyword MajorTopicYN="N">cytotoxicity</Keyword>
</KeywordList>
<CoiStatement>The authors declare no conflict of interest.</CoiStatement>
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<Day>01</Day>
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New Crambescidin-Type Alkaloids from the Indonesian Marine Sponge Clathria bulbotoxa.

New Crambescidin-Type Alkaloids from the Indonesian Marine Sponge Clathria bulbotoxa.

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