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(-)-Calcaridine B, a new chiral aminoimidazole-containing alkaloid from the marine sponge Leucetta chagosensis
LC-DAD/MS-based dereplication of organic extract of a calcareous sponge Leucetta chagosensis afforded one new chiral aminoimidazole-containing alkaloid, (-)-calcaridine B (1), along with one achiral imidazole analog leucettamine E (2) as well as one known imidazole derivative (2E, 9E)-pyronaamidine-...
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Published in: | Journal of asian natural products research 2019-11, Vol.21 (11), p.1123-1128 |
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container_end_page | 1128 |
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container_title | Journal of asian natural products research |
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creator | Tang, Wei-Zhuo Yang, Zhong-Zhen Sun, Fan Wang, Shu-Ping Yang, Fan Jiao, Wei-Hua Lin, Hou-Wen |
description | LC-DAD/MS-based dereplication of organic extract of a calcareous sponge Leucetta chagosensis afforded one new chiral aminoimidazole-containing alkaloid, (-)-calcaridine B (1), along with one achiral imidazole analog leucettamine E (2) as well as one known imidazole derivative (2E, 9E)-pyronaamidine-9-(N-methylimine) (3). Their structures were elucidated on the basis of NMR spectroscopic analyses, and comparing with the literature. The cytotoxic activities of all isolates were evaluated against three human cancer cell lines, and compounds 1 and 3 exhibited mild cytotoxicities toward the MCF-7 cell line with IC
50
values of 25.3-24.2 μM, respectively. |
doi_str_mv | 10.1080/10286020.2018.1499729 |
format | article |
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values of 25.3-24.2 μM, respectively.</description><identifier>ISSN: 1028-6020</identifier><identifier>ISSN: 1477-2213</identifier><identifier>EISSN: 1477-2213</identifier><identifier>DOI: 10.1080/10286020.2018.1499729</identifier><identifier>PMID: 30415579</identifier><language>eng</language><publisher>England: Taylor & Francis</publisher><subject>Alkaloids ; Animals ; Antineoplastic Agents ; Biotechnology ; chiral imidazole alkaloid ; cytotoxicities ; Cytotoxicity ; human cell lines ; Humans ; Imidazole ; inhibitory concentration 50 ; Leucetta ; Leucetta chagosensis ; liquid chromatography ; Marine sponge ; MCF-7 Cells ; Molecular Structure ; neoplasm cells ; NMR ; Nuclear magnetic resonance ; nuclear magnetic resonance spectroscopy ; Porifera ; spectral analysis ; Tumor cell lines</subject><ispartof>Journal of asian natural products research, 2019-11, Vol.21 (11), p.1123-1128</ispartof><rights>2018 Informa UK Limited, trading as Taylor & Francis Group 2018</rights><rights>2018 Informa UK Limited, trading as Taylor & Francis Group</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c427t-a8005501ea981d36703b3c41bd21043bc81eb18ed437331c859197048a3a046e3</citedby><cites>FETCH-LOGICAL-c427t-a8005501ea981d36703b3c41bd21043bc81eb18ed437331c859197048a3a046e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30415579$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tang, Wei-Zhuo</creatorcontrib><creatorcontrib>Yang, Zhong-Zhen</creatorcontrib><creatorcontrib>Sun, Fan</creatorcontrib><creatorcontrib>Wang, Shu-Ping</creatorcontrib><creatorcontrib>Yang, Fan</creatorcontrib><creatorcontrib>Jiao, Wei-Hua</creatorcontrib><creatorcontrib>Lin, Hou-Wen</creatorcontrib><title>(-)-Calcaridine B, a new chiral aminoimidazole-containing alkaloid from the marine sponge Leucetta chagosensis</title><title>Journal of asian natural products research</title><addtitle>J Asian Nat Prod Res</addtitle><description>LC-DAD/MS-based dereplication of organic extract of a calcareous sponge Leucetta chagosensis afforded one new chiral aminoimidazole-containing alkaloid, (-)-calcaridine B (1), along with one achiral imidazole analog leucettamine E (2) as well as one known imidazole derivative (2E, 9E)-pyronaamidine-9-(N-methylimine) (3). Their structures were elucidated on the basis of NMR spectroscopic analyses, and comparing with the literature. The cytotoxic activities of all isolates were evaluated against three human cancer cell lines, and compounds 1 and 3 exhibited mild cytotoxicities toward the MCF-7 cell line with IC
50
values of 25.3-24.2 μM, respectively.</description><subject>Alkaloids</subject><subject>Animals</subject><subject>Antineoplastic Agents</subject><subject>Biotechnology</subject><subject>chiral imidazole alkaloid</subject><subject>cytotoxicities</subject><subject>Cytotoxicity</subject><subject>human cell lines</subject><subject>Humans</subject><subject>Imidazole</subject><subject>inhibitory concentration 50</subject><subject>Leucetta</subject><subject>Leucetta chagosensis</subject><subject>liquid chromatography</subject><subject>Marine sponge</subject><subject>MCF-7 Cells</subject><subject>Molecular Structure</subject><subject>neoplasm cells</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>nuclear magnetic resonance spectroscopy</subject><subject>Porifera</subject><subject>spectral analysis</subject><subject>Tumor cell lines</subject><issn>1028-6020</issn><issn>1477-2213</issn><issn>1477-2213</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFkU2P0zAQQCMEYj_gJ4AicdmVSJmxndq5ARVfUiUucLYmjtP14tjFTrRafj2u2uXAAU724c2zPK-qXiCsEBS8QWBqDQxWDFCtUHSdZN2j6hyFlA1jyB-Xe2GaA3RWXeR8C8AQ1-xpdcZBYNvK7rwKV811syFvKLnBBVu_f11THexdbW5cIl_T5EJ0kxvoV_S2MTHM5IILu5r8D_LRDfWY4lTPN7aeiqQo8j6Gna23djF2nqmYaBezDdnlZ9WTkXy2z0_nZfX944dvm8_N9uunL5t328YIJueGFEDbAlrqFA58LYH33AjsB4YgeG8U2h6VHQSXnKNRbYedBKGIE4i15ZfV1dG7T_HnYvOsJ5eN9Z6CjUvWjLdMiHUn2v-jyBkTnQJZ0Fd_obdxSaF8pAiRKwSpeKHaI2VSzDnZUe-TK6u51wj60E4_tNOHdvrUrsy9PNmXfrLDn6mHWAV4ewRcGGOa6C4mP-iZ7n1MY6JgXNb832_8BsRwpcg</recordid><startdate>20191102</startdate><enddate>20191102</enddate><creator>Tang, Wei-Zhuo</creator><creator>Yang, Zhong-Zhen</creator><creator>Sun, Fan</creator><creator>Wang, Shu-Ping</creator><creator>Yang, Fan</creator><creator>Jiao, Wei-Hua</creator><creator>Lin, Hou-Wen</creator><general>Taylor & Francis</general><general>Taylor & Francis Ltd</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7QR</scope><scope>7SN</scope><scope>7T5</scope><scope>7TO</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>H94</scope><scope>M7N</scope><scope>P64</scope><scope>7X8</scope><scope>7S9</scope><scope>L.6</scope></search><sort><creationdate>20191102</creationdate><title>(-)-Calcaridine B, a new chiral aminoimidazole-containing alkaloid from the marine sponge Leucetta chagosensis</title><author>Tang, Wei-Zhuo ; Yang, Zhong-Zhen ; Sun, Fan ; Wang, Shu-Ping ; Yang, Fan ; Jiao, Wei-Hua ; Lin, Hou-Wen</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c427t-a8005501ea981d36703b3c41bd21043bc81eb18ed437331c859197048a3a046e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Alkaloids</topic><topic>Animals</topic><topic>Antineoplastic Agents</topic><topic>Biotechnology</topic><topic>chiral imidazole alkaloid</topic><topic>cytotoxicities</topic><topic>Cytotoxicity</topic><topic>human cell lines</topic><topic>Humans</topic><topic>Imidazole</topic><topic>inhibitory concentration 50</topic><topic>Leucetta</topic><topic>Leucetta chagosensis</topic><topic>liquid chromatography</topic><topic>Marine sponge</topic><topic>MCF-7 Cells</topic><topic>Molecular Structure</topic><topic>neoplasm cells</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>nuclear magnetic resonance spectroscopy</topic><topic>Porifera</topic><topic>spectral analysis</topic><topic>Tumor cell lines</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tang, Wei-Zhuo</creatorcontrib><creatorcontrib>Yang, Zhong-Zhen</creatorcontrib><creatorcontrib>Sun, Fan</creatorcontrib><creatorcontrib>Wang, Shu-Ping</creatorcontrib><creatorcontrib>Yang, Fan</creatorcontrib><creatorcontrib>Jiao, Wei-Hua</creatorcontrib><creatorcontrib>Lin, Hou-Wen</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Chemoreception Abstracts</collection><collection>Ecology Abstracts</collection><collection>Immunology Abstracts</collection><collection>Oncogenes and Growth Factors Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><jtitle>Journal of asian natural products research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tang, Wei-Zhuo</au><au>Yang, Zhong-Zhen</au><au>Sun, Fan</au><au>Wang, Shu-Ping</au><au>Yang, Fan</au><au>Jiao, Wei-Hua</au><au>Lin, Hou-Wen</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>(-)-Calcaridine B, a new chiral aminoimidazole-containing alkaloid from the marine sponge Leucetta chagosensis</atitle><jtitle>Journal of asian natural products research</jtitle><addtitle>J Asian Nat Prod Res</addtitle><date>2019-11-02</date><risdate>2019</risdate><volume>21</volume><issue>11</issue><spage>1123</spage><epage>1128</epage><pages>1123-1128</pages><issn>1028-6020</issn><issn>1477-2213</issn><eissn>1477-2213</eissn><abstract>LC-DAD/MS-based dereplication of organic extract of a calcareous sponge Leucetta chagosensis afforded one new chiral aminoimidazole-containing alkaloid, (-)-calcaridine B (1), along with one achiral imidazole analog leucettamine E (2) as well as one known imidazole derivative (2E, 9E)-pyronaamidine-9-(N-methylimine) (3). 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50
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subjects | Alkaloids Animals Antineoplastic Agents Biotechnology chiral imidazole alkaloid cytotoxicities Cytotoxicity human cell lines Humans Imidazole inhibitory concentration 50 Leucetta Leucetta chagosensis liquid chromatography Marine sponge MCF-7 Cells Molecular Structure neoplasm cells NMR Nuclear magnetic resonance nuclear magnetic resonance spectroscopy Porifera spectral analysis Tumor cell lines |
title | (-)-Calcaridine B, a new chiral aminoimidazole-containing alkaloid from the marine sponge Leucetta chagosensis |
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