Aplysinopsin-type and Bromotyrosine-derived Alkaloids from the South China Sea Sponge Fascaplysinopsis reticulata View Full Text


Ontology type: schema:ScholarlyArticle      Open Access: True


Article Info

DATE

2019-12

AUTHORS

Qi Wang, Xu-Li Tang, Xiang-Chao Luo, Nicole J. de Voog, Ping-Lin Li, Guo-Qiang Li

ABSTRACT

Seven pairs of new oxygenated aplysinopsin-type enantiomers, (+)- and (-)-oxoaplysinopsins A‒G (1‒7), two new bromotyrosine-derived alkaloids, subereamollines C and D (18 and 19), together with ten known compounds (8‒17) were isolated from the Xisha Islands sponge Fascaplysinopsis reticulata. The planar structures were determined by extensive NMR and MS spectroscopic data. Each of the optically pure enantiomers was achieved by chiral HPLC separation. The absolute configurations were assigned by the quantum chemical calculation methods. Compound 19 showed cytotoxicity against Jurkat cell lines with IC50 value of 0.88 μM. Compounds 2, 16 and 17 showed tyrosine phosphatase 1B (PTP1B) inhibition activity with IC50 value ranging from 7.67 to 26.5 μM, stronger than the positive control of acarbose and 1-deoxynojirimycin. A structural activity relationship for the aplysinopsin-type enantiomers were observed in PTP1B inhibition activity of 2 and cytotoxicity of 3 that the dextrorotary (+)-2 and (+)-3 showed stronger activity than the levorotary (-)-2 and (-)-3. More... »

PAGES

2248

Journal

TITLE

Scientific Reports

ISSUE

1

VOLUME

9

Author Affiliations

Identifiers

URI

http://scigraph.springernature.com/pub.10.1038/s41598-019-38696-3

DOI

http://dx.doi.org/10.1038/s41598-019-38696-3

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1112221709

PUBMED

https://www.ncbi.nlm.nih.gov/pubmed/30783134


Indexing Status Check whether this publication has been indexed by Scopus and Web Of Science using the SN Indexing Status Tool
Incoming Citations Browse incoming citations for this publication using opencitations.net

JSON-LD is the canonical representation for SciGraph data.

TIP: You can open this SciGraph record using an external JSON-LD service: JSON-LD Playground Google SDTT

[
  {
    "@context": "https://springernature.github.io/scigraph/jsonld/sgcontext.json", 
    "about": [
      {
        "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/0305", 
        "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
        "name": "Organic Chemistry", 
        "type": "DefinedTerm"
      }, 
      {
        "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/03", 
        "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
        "name": "Chemical Sciences", 
        "type": "DefinedTerm"
      }
    ], 
    "author": [
      {
        "affiliation": {
          "name": [
            "Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 266003, Qingdao, Republic of China", 
            "Laboratory of Marine Drugs and Biological Products, National Laboratory for Marine Science and Technology, 266235, Qingdao, Republic of China", 
            "College of Chemistry and Chemical Engineering, Ocean University of China, 266100, Qingdao, Republic of China"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Wang", 
        "givenName": "Qi", 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "name": [
            "Institute of Chronic Diseases, Qingdao University, 266071, Qingdao, Republic of China"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Tang", 
        "givenName": "Xu-Li", 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "name": [
            "Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 266003, Qingdao, Republic of China", 
            "Laboratory of Marine Drugs and Biological Products, National Laboratory for Marine Science and Technology, 266235, Qingdao, Republic of China"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Luo", 
        "givenName": "Xiang-Chao", 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Naturalis Biodiversity Center", 
          "id": "https://www.grid.ac/institutes/grid.425948.6", 
          "name": [
            "National Museum of Natural History, 2300 RA, Leiden, The Netherlands"
          ], 
          "type": "Organization"
        }, 
        "familyName": "de Voog", 
        "givenName": "Nicole J.", 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "name": [
            "Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 266003, Qingdao, Republic of China", 
            "Laboratory of Marine Drugs and Biological Products, National Laboratory for Marine Science and Technology, 266235, Qingdao, Republic of China"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Li", 
        "givenName": "Ping-Lin", 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "name": [
            "Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 266003, Qingdao, Republic of China", 
            "Laboratory of Marine Drugs and Biological Products, National Laboratory for Marine Science and Technology, 266235, Qingdao, Republic of China"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Li", 
        "givenName": "Guo-Qiang", 
        "type": "Person"
      }
    ], 
    "citation": [
      {
        "id": "https://doi.org/10.1351/pac198254101907", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1010187507"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.3390/md7020166", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1019202857"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1002/hlca.19890720703", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1022797851"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/s0040-4039(01)92550-x", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1024327454"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.3390/md14010018", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1026405932"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.3390/md8122961", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1027228143"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1039/c2np20112g", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1027808495"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1039/c3np70117d", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1028954886"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1039/c4np00144c", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1032753543"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/0305-0491(86)90184-7", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1034186153"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/0305-0491(86)90184-7", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1034186153"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/s0040-4039(03)00331-9", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1035801200"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1002/anie.201107204", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1040340725"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1002/hlca.19880710412", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1052512478"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/acs.jnatprod.5b00369", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1055100625"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/acs.jnatprod.5b00883", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1055100799"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/acs.jnatprod.5b01012", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1055100845"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/acs.jnatprod.6b00204", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1055100960"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/acs.orglett.5b01503", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1055123937"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/jo00249a025", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1055975299"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/jo01292a044", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056011267"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/np010471e", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056228403"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/np010471e", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056228403"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/np020589a", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056228892"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/np020589a", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056228892"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/np030233e", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056229079"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/np030233e", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056229079"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/np040233u", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056229572"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/np040233u", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056229572"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/np070371u", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056230907"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/np070371u", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056230907"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/np50042a006", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056233943"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/np5009152", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056236138"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/np50101a015", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056236498"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/np50108a004", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056236710"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/np50109a023", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056236765"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/np800142n", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056237375"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/np800142n", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056237375"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/np960095b", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056238220"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/np960095b", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056238220"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/np9805138", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056239539"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/np9805138", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056239539"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/np9901938", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056239711"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/np9901938", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056239711"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/np990343e", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056239815"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/np990343e", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056239815"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/ol702221v", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056257278"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/ol702221v", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056257278"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/ol801750y", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056258511"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/ol801750y", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056258511"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/ol9011019", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056259565"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/ol9011019", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056259565"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1126/science.1255677", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1062470063"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.2174/138955712800626719", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1069183355"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/acs.jnatprod.6b01038", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1074219144"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://app.dimensions.ai/details/publication/pub.1079692388", 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/acs.jnatprod.6b00838", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1083804635"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/acs.jnatprod.6b00673", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1084122883"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/acs.jnatprod.6b00789", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1084122889"
        ], 
        "type": "CreativeWork"
      }
    ], 
    "datePublished": "2019-12", 
    "datePublishedReg": "2019-12-01", 
    "description": "Seven pairs of new oxygenated aplysinopsin-type enantiomers, (+)- and (-)-oxoaplysinopsins A\u2012G (1\u20127), two new bromotyrosine-derived alkaloids, subereamollines C and D (18 and 19), together with ten known compounds (8\u201217) were isolated from the Xisha Islands sponge Fascaplysinopsis reticulata. The planar structures were determined by extensive NMR and MS spectroscopic data. Each of the optically pure enantiomers was achieved by chiral HPLC separation. The absolute configurations were assigned by the quantum chemical calculation methods. Compound 19 showed cytotoxicity against Jurkat cell lines with IC50 value of 0.88\u2009\u03bcM. Compounds 2, 16 and 17 showed tyrosine phosphatase 1B (PTP1B) inhibition activity with IC50 value ranging from 7.67 to 26.5\u2009\u03bcM, stronger than the positive control of acarbose and 1-deoxynojirimycin. A structural activity relationship for the aplysinopsin-type enantiomers were observed in PTP1B inhibition activity of 2 and cytotoxicity of 3 that the dextrorotary (+)-2 and (+)-3 showed stronger activity than the levorotary (-)-2 and (-)-3.", 
    "genre": "research_article", 
    "id": "sg:pub.10.1038/s41598-019-38696-3", 
    "inLanguage": [
      "en"
    ], 
    "isAccessibleForFree": true, 
    "isPartOf": [
      {
        "id": "sg:journal.1045337", 
        "issn": [
          "2045-2322"
        ], 
        "name": "Scientific Reports", 
        "type": "Periodical"
      }, 
      {
        "issueNumber": "1", 
        "type": "PublicationIssue"
      }, 
      {
        "type": "PublicationVolume", 
        "volumeNumber": "9"
      }
    ], 
    "name": "Aplysinopsin-type and Bromotyrosine-derived Alkaloids from the South China Sea Sponge Fascaplysinopsis reticulata", 
    "pagination": "2248", 
    "productId": [
      {
        "name": "readcube_id", 
        "type": "PropertyValue", 
        "value": [
          "078b31dbae341f01ed5890349134fc8446fc113be595138f0e23e0ac2593c1e5"
        ]
      }, 
      {
        "name": "pubmed_id", 
        "type": "PropertyValue", 
        "value": [
          "30783134"
        ]
      }, 
      {
        "name": "nlm_unique_id", 
        "type": "PropertyValue", 
        "value": [
          "101563288"
        ]
      }, 
      {
        "name": "doi", 
        "type": "PropertyValue", 
        "value": [
          "10.1038/s41598-019-38696-3"
        ]
      }, 
      {
        "name": "dimensions_id", 
        "type": "PropertyValue", 
        "value": [
          "pub.1112221709"
        ]
      }
    ], 
    "sameAs": [
      "https://doi.org/10.1038/s41598-019-38696-3", 
      "https://app.dimensions.ai/details/publication/pub.1112221709"
    ], 
    "sdDataset": "articles", 
    "sdDatePublished": "2019-04-11T09:42", 
    "sdLicense": "https://scigraph.springernature.com/explorer/license/", 
    "sdPublisher": {
      "name": "Springer Nature - SN SciGraph project", 
      "type": "Organization"
    }, 
    "sdSource": "s3://com-uberresearch-data-dimensions-target-20181106-alternative/cleanup/v134/2549eaecd7973599484d7c17b260dba0a4ecb94b/merge/v9/a6c9fde33151104705d4d7ff012ea9563521a3ce/jats-lookup/v90/0000000346_0000000346/records_99843_00000004.jsonl", 
    "type": "ScholarlyArticle", 
    "url": "https://www.nature.com/articles/s41598-019-38696-3"
  }
]
 

Download the RDF metadata as:  json-ld nt turtle xml License info

HOW TO GET THIS DATA PROGRAMMATICALLY:

JSON-LD is a popular format for linked data which is fully compatible with JSON.

curl -H 'Accept: application/ld+json' 'https://scigraph.springernature.com/pub.10.1038/s41598-019-38696-3'

N-Triples is a line-based linked data format ideal for batch operations.

curl -H 'Accept: application/n-triples' 'https://scigraph.springernature.com/pub.10.1038/s41598-019-38696-3'

Turtle is a human-readable linked data format.

curl -H 'Accept: text/turtle' 'https://scigraph.springernature.com/pub.10.1038/s41598-019-38696-3'

RDF/XML is a standard XML format for linked data.

curl -H 'Accept: application/rdf+xml' 'https://scigraph.springernature.com/pub.10.1038/s41598-019-38696-3'


 

This table displays all metadata directly associated to this object as RDF triples.

246 TRIPLES      21 PREDICATES      74 URIs      21 LITERALS      9 BLANK NODES

Subject Predicate Object
1 sg:pub.10.1038/s41598-019-38696-3 schema:about anzsrc-for:03
2 anzsrc-for:0305
3 schema:author Na48dd5afb4bb454488fb7554e7fa61a8
4 schema:citation https://app.dimensions.ai/details/publication/pub.1079692388
5 https://doi.org/10.1002/anie.201107204
6 https://doi.org/10.1002/hlca.19880710412
7 https://doi.org/10.1002/hlca.19890720703
8 https://doi.org/10.1016/0305-0491(86)90184-7
9 https://doi.org/10.1016/s0040-4039(01)92550-x
10 https://doi.org/10.1016/s0040-4039(03)00331-9
11 https://doi.org/10.1021/acs.jnatprod.5b00369
12 https://doi.org/10.1021/acs.jnatprod.5b00883
13 https://doi.org/10.1021/acs.jnatprod.5b01012
14 https://doi.org/10.1021/acs.jnatprod.6b00204
15 https://doi.org/10.1021/acs.jnatprod.6b00673
16 https://doi.org/10.1021/acs.jnatprod.6b00789
17 https://doi.org/10.1021/acs.jnatprod.6b00838
18 https://doi.org/10.1021/acs.jnatprod.6b01038
19 https://doi.org/10.1021/acs.orglett.5b01503
20 https://doi.org/10.1021/jo00249a025
21 https://doi.org/10.1021/jo01292a044
22 https://doi.org/10.1021/np010471e
23 https://doi.org/10.1021/np020589a
24 https://doi.org/10.1021/np030233e
25 https://doi.org/10.1021/np040233u
26 https://doi.org/10.1021/np070371u
27 https://doi.org/10.1021/np50042a006
28 https://doi.org/10.1021/np5009152
29 https://doi.org/10.1021/np50101a015
30 https://doi.org/10.1021/np50108a004
31 https://doi.org/10.1021/np50109a023
32 https://doi.org/10.1021/np800142n
33 https://doi.org/10.1021/np960095b
34 https://doi.org/10.1021/np9805138
35 https://doi.org/10.1021/np9901938
36 https://doi.org/10.1021/np990343e
37 https://doi.org/10.1021/ol702221v
38 https://doi.org/10.1021/ol801750y
39 https://doi.org/10.1021/ol9011019
40 https://doi.org/10.1039/c2np20112g
41 https://doi.org/10.1039/c3np70117d
42 https://doi.org/10.1039/c4np00144c
43 https://doi.org/10.1126/science.1255677
44 https://doi.org/10.1351/pac198254101907
45 https://doi.org/10.2174/138955712800626719
46 https://doi.org/10.3390/md14010018
47 https://doi.org/10.3390/md7020166
48 https://doi.org/10.3390/md8122961
49 schema:datePublished 2019-12
50 schema:datePublishedReg 2019-12-01
51 schema:description Seven pairs of new oxygenated aplysinopsin-type enantiomers, (+)- and (-)-oxoaplysinopsins A‒G (1‒7), two new bromotyrosine-derived alkaloids, subereamollines C and D (18 and 19), together with ten known compounds (8‒17) were isolated from the Xisha Islands sponge Fascaplysinopsis reticulata. The planar structures were determined by extensive NMR and MS spectroscopic data. Each of the optically pure enantiomers was achieved by chiral HPLC separation. The absolute configurations were assigned by the quantum chemical calculation methods. Compound 19 showed cytotoxicity against Jurkat cell lines with IC<sub>50</sub> value of 0.88 μM. Compounds 2, 16 and 17 showed tyrosine phosphatase 1B (PTP1B) inhibition activity with IC<sub>50</sub> value ranging from 7.67 to 26.5 μM, stronger than the positive control of acarbose and 1-deoxynojirimycin. A structural activity relationship for the aplysinopsin-type enantiomers were observed in PTP1B inhibition activity of 2 and cytotoxicity of 3 that the dextrorotary (+)-2 and (+)-3 showed stronger activity than the levorotary (-)-2 and (-)-3.
52 schema:genre research_article
53 schema:inLanguage en
54 schema:isAccessibleForFree true
55 schema:isPartOf N012840f37e1b4e00ad51b89ebdf1f858
56 Nd22b2bb96dff4c69a5e88f20a19661f8
57 sg:journal.1045337
58 schema:name Aplysinopsin-type and Bromotyrosine-derived Alkaloids from the South China Sea Sponge Fascaplysinopsis reticulata
59 schema:pagination 2248
60 schema:productId N1ce253844206498ba66da54b68f14db0
61 N289acf7aa5e142709be38ea347077a1f
62 N61dfd8d93cb04201be359dfb6e0d2b75
63 Ncebceafc7da143ceb3f561a97fb450d5
64 Nf6be6f77ff234eefbd677a5d9add8a32
65 schema:sameAs https://app.dimensions.ai/details/publication/pub.1112221709
66 https://doi.org/10.1038/s41598-019-38696-3
67 schema:sdDatePublished 2019-04-11T09:42
68 schema:sdLicense https://scigraph.springernature.com/explorer/license/
69 schema:sdPublisher Ne6c7baadd0764e46a79d47cb80eb1efb
70 schema:url https://www.nature.com/articles/s41598-019-38696-3
71 sgo:license sg:explorer/license/
72 sgo:sdDataset articles
73 rdf:type schema:ScholarlyArticle
74 N012840f37e1b4e00ad51b89ebdf1f858 schema:issueNumber 1
75 rdf:type schema:PublicationIssue
76 N0b0ea96e59624a4d8cc525037764007b rdf:first Nb931d2db463446b69e1425b54b1db041
77 rdf:rest rdf:nil
78 N1571fd470f6643f6ab5cdb2b829b5f9b rdf:first Ndc657d5e99464f969784db82a695ca14
79 rdf:rest Nca51bccbccd44d0898a1908b904c7cb9
80 N1ce253844206498ba66da54b68f14db0 schema:name pubmed_id
81 schema:value 30783134
82 rdf:type schema:PropertyValue
83 N289acf7aa5e142709be38ea347077a1f schema:name doi
84 schema:value 10.1038/s41598-019-38696-3
85 rdf:type schema:PropertyValue
86 N341f21f63e7a497b88fb8788f975cc69 schema:affiliation Na5b68c78dd0044e0868d64351c5750d6
87 schema:familyName Li
88 schema:givenName Ping-Lin
89 rdf:type schema:Person
90 N344318b56de443c587a3c4d05d079fec rdf:first N3c89f2c396704511837e69d5bd978360
91 rdf:rest N1571fd470f6643f6ab5cdb2b829b5f9b
92 N3a9348e3a8c443999f4b77dc5f18e23d schema:name Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 266003, Qingdao, Republic of China
93 Laboratory of Marine Drugs and Biological Products, National Laboratory for Marine Science and Technology, 266235, Qingdao, Republic of China
94 rdf:type schema:Organization
95 N3c89f2c396704511837e69d5bd978360 schema:affiliation N3a9348e3a8c443999f4b77dc5f18e23d
96 schema:familyName Luo
97 schema:givenName Xiang-Chao
98 rdf:type schema:Person
99 N61dfd8d93cb04201be359dfb6e0d2b75 schema:name dimensions_id
100 schema:value pub.1112221709
101 rdf:type schema:PropertyValue
102 N79a37b7e584748c0950d22137eed1247 schema:affiliation Ne5d110c2dabf4b7dbd60f3b799ba3c8a
103 schema:familyName Tang
104 schema:givenName Xu-Li
105 rdf:type schema:Person
106 N9a3f01b182e941f385122df11cdb0a4d schema:name Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 266003, Qingdao, Republic of China
107 Laboratory of Marine Drugs and Biological Products, National Laboratory for Marine Science and Technology, 266235, Qingdao, Republic of China
108 rdf:type schema:Organization
109 N9d6856255d5a40ba96ace9166db974c8 schema:name College of Chemistry and Chemical Engineering, Ocean University of China, 266100, Qingdao, Republic of China
110 Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 266003, Qingdao, Republic of China
111 Laboratory of Marine Drugs and Biological Products, National Laboratory for Marine Science and Technology, 266235, Qingdao, Republic of China
112 rdf:type schema:Organization
113 Na48dd5afb4bb454488fb7554e7fa61a8 rdf:first Nd7c667ea578b466f9872b121b8fda8b3
114 rdf:rest Nb0eb60667d5f4dce885a2f5613f751a0
115 Na5b68c78dd0044e0868d64351c5750d6 schema:name Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 266003, Qingdao, Republic of China
116 Laboratory of Marine Drugs and Biological Products, National Laboratory for Marine Science and Technology, 266235, Qingdao, Republic of China
117 rdf:type schema:Organization
118 Nb0eb60667d5f4dce885a2f5613f751a0 rdf:first N79a37b7e584748c0950d22137eed1247
119 rdf:rest N344318b56de443c587a3c4d05d079fec
120 Nb931d2db463446b69e1425b54b1db041 schema:affiliation N9a3f01b182e941f385122df11cdb0a4d
121 schema:familyName Li
122 schema:givenName Guo-Qiang
123 rdf:type schema:Person
124 Nca51bccbccd44d0898a1908b904c7cb9 rdf:first N341f21f63e7a497b88fb8788f975cc69
125 rdf:rest N0b0ea96e59624a4d8cc525037764007b
126 Ncebceafc7da143ceb3f561a97fb450d5 schema:name readcube_id
127 schema:value 078b31dbae341f01ed5890349134fc8446fc113be595138f0e23e0ac2593c1e5
128 rdf:type schema:PropertyValue
129 Nd22b2bb96dff4c69a5e88f20a19661f8 schema:volumeNumber 9
130 rdf:type schema:PublicationVolume
131 Nd7c667ea578b466f9872b121b8fda8b3 schema:affiliation N9d6856255d5a40ba96ace9166db974c8
132 schema:familyName Wang
133 schema:givenName Qi
134 rdf:type schema:Person
135 Ndc657d5e99464f969784db82a695ca14 schema:affiliation https://www.grid.ac/institutes/grid.425948.6
136 schema:familyName de Voog
137 schema:givenName Nicole J.
138 rdf:type schema:Person
139 Ne5d110c2dabf4b7dbd60f3b799ba3c8a schema:name Institute of Chronic Diseases, Qingdao University, 266071, Qingdao, Republic of China
140 rdf:type schema:Organization
141 Ne6c7baadd0764e46a79d47cb80eb1efb schema:name Springer Nature - SN SciGraph project
142 rdf:type schema:Organization
143 Nf6be6f77ff234eefbd677a5d9add8a32 schema:name nlm_unique_id
144 schema:value 101563288
145 rdf:type schema:PropertyValue
146 anzsrc-for:03 schema:inDefinedTermSet anzsrc-for:
147 schema:name Chemical Sciences
148 rdf:type schema:DefinedTerm
149 anzsrc-for:0305 schema:inDefinedTermSet anzsrc-for:
150 schema:name Organic Chemistry
151 rdf:type schema:DefinedTerm
152 sg:journal.1045337 schema:issn 2045-2322
153 schema:name Scientific Reports
154 rdf:type schema:Periodical
155 https://app.dimensions.ai/details/publication/pub.1079692388 schema:CreativeWork
156 https://doi.org/10.1002/anie.201107204 schema:sameAs https://app.dimensions.ai/details/publication/pub.1040340725
157 rdf:type schema:CreativeWork
158 https://doi.org/10.1002/hlca.19880710412 schema:sameAs https://app.dimensions.ai/details/publication/pub.1052512478
159 rdf:type schema:CreativeWork
160 https://doi.org/10.1002/hlca.19890720703 schema:sameAs https://app.dimensions.ai/details/publication/pub.1022797851
161 rdf:type schema:CreativeWork
162 https://doi.org/10.1016/0305-0491(86)90184-7 schema:sameAs https://app.dimensions.ai/details/publication/pub.1034186153
163 rdf:type schema:CreativeWork
164 https://doi.org/10.1016/s0040-4039(01)92550-x schema:sameAs https://app.dimensions.ai/details/publication/pub.1024327454
165 rdf:type schema:CreativeWork
166 https://doi.org/10.1016/s0040-4039(03)00331-9 schema:sameAs https://app.dimensions.ai/details/publication/pub.1035801200
167 rdf:type schema:CreativeWork
168 https://doi.org/10.1021/acs.jnatprod.5b00369 schema:sameAs https://app.dimensions.ai/details/publication/pub.1055100625
169 rdf:type schema:CreativeWork
170 https://doi.org/10.1021/acs.jnatprod.5b00883 schema:sameAs https://app.dimensions.ai/details/publication/pub.1055100799
171 rdf:type schema:CreativeWork
172 https://doi.org/10.1021/acs.jnatprod.5b01012 schema:sameAs https://app.dimensions.ai/details/publication/pub.1055100845
173 rdf:type schema:CreativeWork
174 https://doi.org/10.1021/acs.jnatprod.6b00204 schema:sameAs https://app.dimensions.ai/details/publication/pub.1055100960
175 rdf:type schema:CreativeWork
176 https://doi.org/10.1021/acs.jnatprod.6b00673 schema:sameAs https://app.dimensions.ai/details/publication/pub.1084122883
177 rdf:type schema:CreativeWork
178 https://doi.org/10.1021/acs.jnatprod.6b00789 schema:sameAs https://app.dimensions.ai/details/publication/pub.1084122889
179 rdf:type schema:CreativeWork
180 https://doi.org/10.1021/acs.jnatprod.6b00838 schema:sameAs https://app.dimensions.ai/details/publication/pub.1083804635
181 rdf:type schema:CreativeWork
182 https://doi.org/10.1021/acs.jnatprod.6b01038 schema:sameAs https://app.dimensions.ai/details/publication/pub.1074219144
183 rdf:type schema:CreativeWork
184 https://doi.org/10.1021/acs.orglett.5b01503 schema:sameAs https://app.dimensions.ai/details/publication/pub.1055123937
185 rdf:type schema:CreativeWork
186 https://doi.org/10.1021/jo00249a025 schema:sameAs https://app.dimensions.ai/details/publication/pub.1055975299
187 rdf:type schema:CreativeWork
188 https://doi.org/10.1021/jo01292a044 schema:sameAs https://app.dimensions.ai/details/publication/pub.1056011267
189 rdf:type schema:CreativeWork
190 https://doi.org/10.1021/np010471e schema:sameAs https://app.dimensions.ai/details/publication/pub.1056228403
191 rdf:type schema:CreativeWork
192 https://doi.org/10.1021/np020589a schema:sameAs https://app.dimensions.ai/details/publication/pub.1056228892
193 rdf:type schema:CreativeWork
194 https://doi.org/10.1021/np030233e schema:sameAs https://app.dimensions.ai/details/publication/pub.1056229079
195 rdf:type schema:CreativeWork
196 https://doi.org/10.1021/np040233u schema:sameAs https://app.dimensions.ai/details/publication/pub.1056229572
197 rdf:type schema:CreativeWork
198 https://doi.org/10.1021/np070371u schema:sameAs https://app.dimensions.ai/details/publication/pub.1056230907
199 rdf:type schema:CreativeWork
200 https://doi.org/10.1021/np50042a006 schema:sameAs https://app.dimensions.ai/details/publication/pub.1056233943
201 rdf:type schema:CreativeWork
202 https://doi.org/10.1021/np5009152 schema:sameAs https://app.dimensions.ai/details/publication/pub.1056236138
203 rdf:type schema:CreativeWork
204 https://doi.org/10.1021/np50101a015 schema:sameAs https://app.dimensions.ai/details/publication/pub.1056236498
205 rdf:type schema:CreativeWork
206 https://doi.org/10.1021/np50108a004 schema:sameAs https://app.dimensions.ai/details/publication/pub.1056236710
207 rdf:type schema:CreativeWork
208 https://doi.org/10.1021/np50109a023 schema:sameAs https://app.dimensions.ai/details/publication/pub.1056236765
209 rdf:type schema:CreativeWork
210 https://doi.org/10.1021/np800142n schema:sameAs https://app.dimensions.ai/details/publication/pub.1056237375
211 rdf:type schema:CreativeWork
212 https://doi.org/10.1021/np960095b schema:sameAs https://app.dimensions.ai/details/publication/pub.1056238220
213 rdf:type schema:CreativeWork
214 https://doi.org/10.1021/np9805138 schema:sameAs https://app.dimensions.ai/details/publication/pub.1056239539
215 rdf:type schema:CreativeWork
216 https://doi.org/10.1021/np9901938 schema:sameAs https://app.dimensions.ai/details/publication/pub.1056239711
217 rdf:type schema:CreativeWork
218 https://doi.org/10.1021/np990343e schema:sameAs https://app.dimensions.ai/details/publication/pub.1056239815
219 rdf:type schema:CreativeWork
220 https://doi.org/10.1021/ol702221v schema:sameAs https://app.dimensions.ai/details/publication/pub.1056257278
221 rdf:type schema:CreativeWork
222 https://doi.org/10.1021/ol801750y schema:sameAs https://app.dimensions.ai/details/publication/pub.1056258511
223 rdf:type schema:CreativeWork
224 https://doi.org/10.1021/ol9011019 schema:sameAs https://app.dimensions.ai/details/publication/pub.1056259565
225 rdf:type schema:CreativeWork
226 https://doi.org/10.1039/c2np20112g schema:sameAs https://app.dimensions.ai/details/publication/pub.1027808495
227 rdf:type schema:CreativeWork
228 https://doi.org/10.1039/c3np70117d schema:sameAs https://app.dimensions.ai/details/publication/pub.1028954886
229 rdf:type schema:CreativeWork
230 https://doi.org/10.1039/c4np00144c schema:sameAs https://app.dimensions.ai/details/publication/pub.1032753543
231 rdf:type schema:CreativeWork
232 https://doi.org/10.1126/science.1255677 schema:sameAs https://app.dimensions.ai/details/publication/pub.1062470063
233 rdf:type schema:CreativeWork
234 https://doi.org/10.1351/pac198254101907 schema:sameAs https://app.dimensions.ai/details/publication/pub.1010187507
235 rdf:type schema:CreativeWork
236 https://doi.org/10.2174/138955712800626719 schema:sameAs https://app.dimensions.ai/details/publication/pub.1069183355
237 rdf:type schema:CreativeWork
238 https://doi.org/10.3390/md14010018 schema:sameAs https://app.dimensions.ai/details/publication/pub.1026405932
239 rdf:type schema:CreativeWork
240 https://doi.org/10.3390/md7020166 schema:sameAs https://app.dimensions.ai/details/publication/pub.1019202857
241 rdf:type schema:CreativeWork
242 https://doi.org/10.3390/md8122961 schema:sameAs https://app.dimensions.ai/details/publication/pub.1027228143
243 rdf:type schema:CreativeWork
244 https://www.grid.ac/institutes/grid.425948.6 schema:alternateName Naturalis Biodiversity Center
245 schema:name National Museum of Natural History, 2300 RA, Leiden, The Netherlands
246 rdf:type schema:Organization
 




Preview window. Press ESC to close (or click here)


...