Coscinoderines A–J: Trisubstituted Pyridinium-Containing Norterpenoids Isolated from Coscinoderma bakusi, a Tropical Marine Sponge

Ten new norterpene alkaloids, coscinoderines A–J (1–10), were isolated from the marine sponge Coscinoderma bakusi. Each coscinoderine contains a 1,2,5-trisubstituted pyridinium moiety bearing a terpene unit at the C-2 position. Their structures were elucidated by analysis of NMR and HRMS data, and t...

Full description

Saved in:
Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2023-09, Vol.86 (9), p.2145-2150
Main Authors: Tran, Huynh Nguyen Khanh, Kim, Min Jin, Shin, A-Young, Tran, Le Viet Ha, Lee, Jihoon, Lee, Yeon-Ju
Format: Article
Language:English
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by
cites cdi_FETCH-LOGICAL-a274t-aa7cd1d85eb1675967220c44b7fb522034426e14b2a4f8ed4401217997bda6fe3
container_end_page 2150
container_issue 9
container_start_page 2145
container_title Journal of natural products (Washington, D.C.)
container_volume 86
creator Tran, Huynh Nguyen Khanh
Kim, Min Jin
Shin, A-Young
Tran, Le Viet Ha
Lee, Jihoon
Lee, Yeon-Ju
description Ten new norterpene alkaloids, coscinoderines A–J (1–10), were isolated from the marine sponge Coscinoderma bakusi. Each coscinoderine contains a 1,2,5-trisubstituted pyridinium moiety bearing a terpene unit at the C-2 position. Their structures were elucidated by analysis of NMR and HRMS data, and the absolute stereochemistry of 4 with a 2-methylbutyl group attached to the nitrogen was determined from a comparison of the calculated and measured ECD spectra. The isolation of coscinoderines expands the repertoire of pyridinium alkaloids isolated from marine sponges.
doi_str_mv 10.1021/acs.jnatprod.3c00358
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2856320064</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2856320064</sourcerecordid><originalsourceid>FETCH-LOGICAL-a274t-aa7cd1d85eb1675967220c44b7fb522034426e14b2a4f8ed4401217997bda6fe3</originalsourceid><addsrcrecordid>eNp9kL1OwzAUhS0EEqXwBgweGUixHcdJ2aqKn6LyI1Hm6CZ2KpfEDnYydGPgDXhDngSXFrEx3SPdc87V_RA6pWRECaMXUPrRykDXOitHcUlInGR7aEATRiJBWLKPBoSKOIozwQ_RkfcrEjxknAzQx9T6UhsrldNGeTz5ev-8u8QLp31f-E53fackflo7LbXRfRNNrekgSLPED9Z1yrXKWC09nnlbw8ZcOdvgv9oGcAGvvdfnGEKvbXUJNb6HzT383FqzVMfooILaq5PdHKKX66vF9DaaP97MppN5BCzlXQSQlpLKLFEFFWkyFiljpOS8SKsiCTLmnAlFecGAV5mSnBPKaDoep4UEUal4iM62vQHUW698lzfal6quwSjb-5xliYgZIYIHK99aS2e9d6rKW6cbcOucknwDPQ_Q81_o-Q56iJFt7Gdre2fCP_9HvgG7sIzW</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2856320064</pqid></control><display><type>article</type><title>Coscinoderines A–J: Trisubstituted Pyridinium-Containing Norterpenoids Isolated from Coscinoderma bakusi, a Tropical Marine Sponge</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Tran, Huynh Nguyen Khanh ; Kim, Min Jin ; Shin, A-Young ; Tran, Le Viet Ha ; Lee, Jihoon ; Lee, Yeon-Ju</creator><creatorcontrib>Tran, Huynh Nguyen Khanh ; Kim, Min Jin ; Shin, A-Young ; Tran, Le Viet Ha ; Lee, Jihoon ; Lee, Yeon-Ju</creatorcontrib><description>Ten new norterpene alkaloids, coscinoderines A–J (1–10), were isolated from the marine sponge Coscinoderma bakusi. Each coscinoderine contains a 1,2,5-trisubstituted pyridinium moiety bearing a terpene unit at the C-2 position. Their structures were elucidated by analysis of NMR and HRMS data, and the absolute stereochemistry of 4 with a 2-methylbutyl group attached to the nitrogen was determined from a comparison of the calculated and measured ECD spectra. The isolation of coscinoderines expands the repertoire of pyridinium alkaloids isolated from marine sponges.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/acs.jnatprod.3c00358</identifier><language>eng</language><publisher>American Chemical Society and American Society of Pharmacognosy</publisher><ispartof>Journal of natural products (Washington, D.C.), 2023-09, Vol.86 (9), p.2145-2150</ispartof><rights>2023 American Chemical Society and American Society of Pharmacognosy</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-a274t-aa7cd1d85eb1675967220c44b7fb522034426e14b2a4f8ed4401217997bda6fe3</cites><orcidid>0000-0003-4814-943X ; 0000-0002-9799-7999</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Tran, Huynh Nguyen Khanh</creatorcontrib><creatorcontrib>Kim, Min Jin</creatorcontrib><creatorcontrib>Shin, A-Young</creatorcontrib><creatorcontrib>Tran, Le Viet Ha</creatorcontrib><creatorcontrib>Lee, Jihoon</creatorcontrib><creatorcontrib>Lee, Yeon-Ju</creatorcontrib><title>Coscinoderines A–J: Trisubstituted Pyridinium-Containing Norterpenoids Isolated from Coscinoderma bakusi, a Tropical Marine Sponge</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Ten new norterpene alkaloids, coscinoderines A–J (1–10), were isolated from the marine sponge Coscinoderma bakusi. Each coscinoderine contains a 1,2,5-trisubstituted pyridinium moiety bearing a terpene unit at the C-2 position. Their structures were elucidated by analysis of NMR and HRMS data, and the absolute stereochemistry of 4 with a 2-methylbutyl group attached to the nitrogen was determined from a comparison of the calculated and measured ECD spectra. The isolation of coscinoderines expands the repertoire of pyridinium alkaloids isolated from marine sponges.</description><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp9kL1OwzAUhS0EEqXwBgweGUixHcdJ2aqKn6LyI1Hm6CZ2KpfEDnYydGPgDXhDngSXFrEx3SPdc87V_RA6pWRECaMXUPrRykDXOitHcUlInGR7aEATRiJBWLKPBoSKOIozwQ_RkfcrEjxknAzQx9T6UhsrldNGeTz5ev-8u8QLp31f-E53fackflo7LbXRfRNNrekgSLPED9Z1yrXKWC09nnlbw8ZcOdvgv9oGcAGvvdfnGEKvbXUJNb6HzT383FqzVMfooILaq5PdHKKX66vF9DaaP97MppN5BCzlXQSQlpLKLFEFFWkyFiljpOS8SKsiCTLmnAlFecGAV5mSnBPKaDoep4UEUal4iM62vQHUW698lzfal6quwSjb-5xliYgZIYIHK99aS2e9d6rKW6cbcOucknwDPQ_Q81_o-Q56iJFt7Gdre2fCP_9HvgG7sIzW</recordid><startdate>20230922</startdate><enddate>20230922</enddate><creator>Tran, Huynh Nguyen Khanh</creator><creator>Kim, Min Jin</creator><creator>Shin, A-Young</creator><creator>Tran, Le Viet Ha</creator><creator>Lee, Jihoon</creator><creator>Lee, Yeon-Ju</creator><general>American Chemical Society and American Society of Pharmacognosy</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-4814-943X</orcidid><orcidid>https://orcid.org/0000-0002-9799-7999</orcidid></search><sort><creationdate>20230922</creationdate><title>Coscinoderines A–J: Trisubstituted Pyridinium-Containing Norterpenoids Isolated from Coscinoderma bakusi, a Tropical Marine Sponge</title><author>Tran, Huynh Nguyen Khanh ; Kim, Min Jin ; Shin, A-Young ; Tran, Le Viet Ha ; Lee, Jihoon ; Lee, Yeon-Ju</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a274t-aa7cd1d85eb1675967220c44b7fb522034426e14b2a4f8ed4401217997bda6fe3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tran, Huynh Nguyen Khanh</creatorcontrib><creatorcontrib>Kim, Min Jin</creatorcontrib><creatorcontrib>Shin, A-Young</creatorcontrib><creatorcontrib>Tran, Le Viet Ha</creatorcontrib><creatorcontrib>Lee, Jihoon</creatorcontrib><creatorcontrib>Lee, Yeon-Ju</creatorcontrib><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tran, Huynh Nguyen Khanh</au><au>Kim, Min Jin</au><au>Shin, A-Young</au><au>Tran, Le Viet Ha</au><au>Lee, Jihoon</au><au>Lee, Yeon-Ju</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Coscinoderines A–J: Trisubstituted Pyridinium-Containing Norterpenoids Isolated from Coscinoderma bakusi, a Tropical Marine Sponge</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2023-09-22</date><risdate>2023</risdate><volume>86</volume><issue>9</issue><spage>2145</spage><epage>2150</epage><pages>2145-2150</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><abstract>Ten new norterpene alkaloids, coscinoderines A–J (1–10), were isolated from the marine sponge Coscinoderma bakusi. Each coscinoderine contains a 1,2,5-trisubstituted pyridinium moiety bearing a terpene unit at the C-2 position. Their structures were elucidated by analysis of NMR and HRMS data, and the absolute stereochemistry of 4 with a 2-methylbutyl group attached to the nitrogen was determined from a comparison of the calculated and measured ECD spectra. The isolation of coscinoderines expands the repertoire of pyridinium alkaloids isolated from marine sponges.</abstract><pub>American Chemical Society and American Society of Pharmacognosy</pub><doi>10.1021/acs.jnatprod.3c00358</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0003-4814-943X</orcidid><orcidid>https://orcid.org/0000-0002-9799-7999</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 0163-3864
ispartof Journal of natural products (Washington, D.C.), 2023-09, Vol.86 (9), p.2145-2150
issn 0163-3864
1520-6025
language eng
recordid cdi_proquest_miscellaneous_2856320064
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
title Coscinoderines A–J: Trisubstituted Pyridinium-Containing Norterpenoids Isolated from Coscinoderma bakusi, a Tropical Marine Sponge
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-07T21%3A05%3A17IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Coscinoderines%20A%E2%80%93J:%20Trisubstituted%20Pyridinium-Containing%20Norterpenoids%20Isolated%20from%20Coscinoderma%20bakusi,%20a%20Tropical%20Marine%20Sponge&rft.jtitle=Journal%20of%20natural%20products%20(Washington,%20D.C.)&rft.au=Tran,%20Huynh%20Nguyen%20Khanh&rft.date=2023-09-22&rft.volume=86&rft.issue=9&rft.spage=2145&rft.epage=2150&rft.pages=2145-2150&rft.issn=0163-3864&rft.eissn=1520-6025&rft_id=info:doi/10.1021/acs.jnatprod.3c00358&rft_dat=%3Cproquest_cross%3E2856320064%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a274t-aa7cd1d85eb1675967220c44b7fb522034426e14b2a4f8ed4401217997bda6fe3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2856320064&rft_id=info:pmid/&rfr_iscdi=true