Structure and Absolute Configuration of Diterpenoids from Hymenaea stigonocarpa

Chemical investigations of the ethanolic extracts from the flowers and leaves of Hymenaea stigonocarpa Mart. ex Hayne afforded one new ent-halimane diterpenoid, 18-hydroxy-ent-halima-1­(10),13-(E)-dien-15-oic acid (1), together with five known compounds (2–6). The structural elucidation was performe...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of natural products (Washington, D.C.) D.C.), 2015-06, Vol.78 (6), p.1451-1455
Hauptverfasser: Monteiro, Afif F, Batista, João M, Machado, Michelle A, Severino, Richele P, Blanch, Ewan W, Bolzani, Vanderlan S, Vieira, Paulo C, Severino, Vanessa G. P
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 1455
container_issue 6
container_start_page 1451
container_title Journal of natural products (Washington, D.C.)
container_volume 78
creator Monteiro, Afif F
Batista, João M
Machado, Michelle A
Severino, Richele P
Blanch, Ewan W
Bolzani, Vanderlan S
Vieira, Paulo C
Severino, Vanessa G. P
description Chemical investigations of the ethanolic extracts from the flowers and leaves of Hymenaea stigonocarpa Mart. ex Hayne afforded one new ent-halimane diterpenoid, 18-hydroxy-ent-halima-1­(10),13-(E)-dien-15-oic acid (1), together with five known compounds (2–6). The structural elucidation was performed by means of NMR (COSY, HSQC, HMBC, and NOESY) and MS analyses. Complete 1H and 13C NMR data assignments are also reported for labd-13-en-8β-ol-15-oic (2) and labd-7,13-dien-15-oic (3) acids. The absolute configurations of 1 and 2 were established by comparison of experimental and calculated Raman optical activity spectra.
doi_str_mv 10.1021/acs.jnatprod.5b00166
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1691597173</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1691597173</sourcerecordid><originalsourceid>FETCH-LOGICAL-a348t-57d0e5c62f9f94aabbca2fd651faad8c06813f5a73d15aa36a0fb1a347fcd5a93</originalsourceid><addsrcrecordid>eNp9kMtOwzAQRS0EoqXwBwh5ySbFjmMnWVblKVXqAlhbEz-qVIldbGfRvyfQliWrkUb33NEchG4pmVOS0wdQcb51kHbB6zlvCKFCnKEp5TnJBMn5OZqOK5axShQTdBXjlhDCSM0v0SQXhNVVmU_R-j2FQaUhGAxO40UTfTckg5fe2XYzBEitd9hb_NgmE3bG-VZHbIPv8eu-Nw4M4JjajXdeQdjBNbqw0EVzc5wz9Pn89LF8zVbrl7flYpUBK6qU8VITw5XIbW3rAqBpFORWC04tgK4UERVllkPJNOUATACxDR3Z0irNoWYzdH_oHd__GkxMsm-jMl0HzvghSipqyuuSlmyMFoeoCj7GYKzchbaHsJeUyB-VclQpTyrlUeWI3R0vDE1v9B90cjcGyCHwi_shuPHh_zu_ASrRhZs</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1691597173</pqid></control><display><type>article</type><title>Structure and Absolute Configuration of Diterpenoids from Hymenaea stigonocarpa</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Monteiro, Afif F ; Batista, João M ; Machado, Michelle A ; Severino, Richele P ; Blanch, Ewan W ; Bolzani, Vanderlan S ; Vieira, Paulo C ; Severino, Vanessa G. P</creator><creatorcontrib>Monteiro, Afif F ; Batista, João M ; Machado, Michelle A ; Severino, Richele P ; Blanch, Ewan W ; Bolzani, Vanderlan S ; Vieira, Paulo C ; Severino, Vanessa G. P</creatorcontrib><description>Chemical investigations of the ethanolic extracts from the flowers and leaves of Hymenaea stigonocarpa Mart. ex Hayne afforded one new ent-halimane diterpenoid, 18-hydroxy-ent-halima-1­(10),13-(E)-dien-15-oic acid (1), together with five known compounds (2–6). The structural elucidation was performed by means of NMR (COSY, HSQC, HMBC, and NOESY) and MS analyses. Complete 1H and 13C NMR data assignments are also reported for labd-13-en-8β-ol-15-oic (2) and labd-7,13-dien-15-oic (3) acids. The absolute configurations of 1 and 2 were established by comparison of experimental and calculated Raman optical activity spectra.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/acs.jnatprod.5b00166</identifier><identifier>PMID: 26039872</identifier><language>eng</language><publisher>United States: American Chemical Society and American Society of Pharmacognosy</publisher><subject>Brazil ; Diterpenes - chemistry ; Diterpenes - isolation &amp; purification ; Flowers - chemistry ; Hymenaea - chemistry ; Molecular Structure ; Nuclear Magnetic Resonance, Biomolecular ; Plant Leaves - chemistry</subject><ispartof>Journal of natural products (Washington, D.C.), 2015-06, Vol.78 (6), p.1451-1455</ispartof><rights>Copyright © American Chemical Society and American Society of Pharmacognosy</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a348t-57d0e5c62f9f94aabbca2fd651faad8c06813f5a73d15aa36a0fb1a347fcd5a93</citedby><cites>FETCH-LOGICAL-a348t-57d0e5c62f9f94aabbca2fd651faad8c06813f5a73d15aa36a0fb1a347fcd5a93</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.jnatprod.5b00166$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.jnatprod.5b00166$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26039872$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Monteiro, Afif F</creatorcontrib><creatorcontrib>Batista, João M</creatorcontrib><creatorcontrib>Machado, Michelle A</creatorcontrib><creatorcontrib>Severino, Richele P</creatorcontrib><creatorcontrib>Blanch, Ewan W</creatorcontrib><creatorcontrib>Bolzani, Vanderlan S</creatorcontrib><creatorcontrib>Vieira, Paulo C</creatorcontrib><creatorcontrib>Severino, Vanessa G. P</creatorcontrib><title>Structure and Absolute Configuration of Diterpenoids from Hymenaea stigonocarpa</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Chemical investigations of the ethanolic extracts from the flowers and leaves of Hymenaea stigonocarpa Mart. ex Hayne afforded one new ent-halimane diterpenoid, 18-hydroxy-ent-halima-1­(10),13-(E)-dien-15-oic acid (1), together with five known compounds (2–6). The structural elucidation was performed by means of NMR (COSY, HSQC, HMBC, and NOESY) and MS analyses. Complete 1H and 13C NMR data assignments are also reported for labd-13-en-8β-ol-15-oic (2) and labd-7,13-dien-15-oic (3) acids. The absolute configurations of 1 and 2 were established by comparison of experimental and calculated Raman optical activity spectra.</description><subject>Brazil</subject><subject>Diterpenes - chemistry</subject><subject>Diterpenes - isolation &amp; purification</subject><subject>Flowers - chemistry</subject><subject>Hymenaea - chemistry</subject><subject>Molecular Structure</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Plant Leaves - chemistry</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kMtOwzAQRS0EoqXwBwh5ySbFjmMnWVblKVXqAlhbEz-qVIldbGfRvyfQliWrkUb33NEchG4pmVOS0wdQcb51kHbB6zlvCKFCnKEp5TnJBMn5OZqOK5axShQTdBXjlhDCSM0v0SQXhNVVmU_R-j2FQaUhGAxO40UTfTckg5fe2XYzBEitd9hb_NgmE3bG-VZHbIPv8eu-Nw4M4JjajXdeQdjBNbqw0EVzc5wz9Pn89LF8zVbrl7flYpUBK6qU8VITw5XIbW3rAqBpFORWC04tgK4UERVllkPJNOUATACxDR3Z0irNoWYzdH_oHd__GkxMsm-jMl0HzvghSipqyuuSlmyMFoeoCj7GYKzchbaHsJeUyB-VclQpTyrlUeWI3R0vDE1v9B90cjcGyCHwi_shuPHh_zu_ASrRhZs</recordid><startdate>20150626</startdate><enddate>20150626</enddate><creator>Monteiro, Afif F</creator><creator>Batista, João M</creator><creator>Machado, Michelle A</creator><creator>Severino, Richele P</creator><creator>Blanch, Ewan W</creator><creator>Bolzani, Vanderlan S</creator><creator>Vieira, Paulo C</creator><creator>Severino, Vanessa G. P</creator><general>American Chemical Society and American Society of Pharmacognosy</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>7X8</scope></search><sort><creationdate>20150626</creationdate><title>Structure and Absolute Configuration of Diterpenoids from Hymenaea stigonocarpa</title><author>Monteiro, Afif F ; Batista, João M ; Machado, Michelle A ; Severino, Richele P ; Blanch, Ewan W ; Bolzani, Vanderlan S ; Vieira, Paulo C ; Severino, Vanessa G. P</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a348t-57d0e5c62f9f94aabbca2fd651faad8c06813f5a73d15aa36a0fb1a347fcd5a93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Brazil</topic><topic>Diterpenes - chemistry</topic><topic>Diterpenes - isolation &amp; purification</topic><topic>Flowers - chemistry</topic><topic>Hymenaea - chemistry</topic><topic>Molecular Structure</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Plant Leaves - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Monteiro, Afif F</creatorcontrib><creatorcontrib>Batista, João M</creatorcontrib><creatorcontrib>Machado, Michelle A</creatorcontrib><creatorcontrib>Severino, Richele P</creatorcontrib><creatorcontrib>Blanch, Ewan W</creatorcontrib><creatorcontrib>Bolzani, Vanderlan S</creatorcontrib><creatorcontrib>Vieira, Paulo C</creatorcontrib><creatorcontrib>Severino, Vanessa G. P</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><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>Monteiro, Afif F</au><au>Batista, João M</au><au>Machado, Michelle A</au><au>Severino, Richele P</au><au>Blanch, Ewan W</au><au>Bolzani, Vanderlan S</au><au>Vieira, Paulo C</au><au>Severino, Vanessa G. P</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Structure and Absolute Configuration of Diterpenoids from Hymenaea stigonocarpa</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2015-06-26</date><risdate>2015</risdate><volume>78</volume><issue>6</issue><spage>1451</spage><epage>1455</epage><pages>1451-1455</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><abstract>Chemical investigations of the ethanolic extracts from the flowers and leaves of Hymenaea stigonocarpa Mart. ex Hayne afforded one new ent-halimane diterpenoid, 18-hydroxy-ent-halima-1­(10),13-(E)-dien-15-oic acid (1), together with five known compounds (2–6). The structural elucidation was performed by means of NMR (COSY, HSQC, HMBC, and NOESY) and MS analyses. Complete 1H and 13C NMR data assignments are also reported for labd-13-en-8β-ol-15-oic (2) and labd-7,13-dien-15-oic (3) acids. The absolute configurations of 1 and 2 were established by comparison of experimental and calculated Raman optical activity spectra.</abstract><cop>United States</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>26039872</pmid><doi>10.1021/acs.jnatprod.5b00166</doi><tpages>5</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0163-3864
ispartof Journal of natural products (Washington, D.C.), 2015-06, Vol.78 (6), p.1451-1455
issn 0163-3864
1520-6025
language eng
recordid cdi_proquest_miscellaneous_1691597173
source MEDLINE; American Chemical Society Journals
subjects Brazil
Diterpenes - chemistry
Diterpenes - isolation & purification
Flowers - chemistry
Hymenaea - chemistry
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Plant Leaves - chemistry
title Structure and Absolute Configuration of Diterpenoids from Hymenaea stigonocarpa
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-04T09%3A04%3A53IST&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=Structure%20and%20Absolute%20Configuration%20of%20Diterpenoids%20from%20Hymenaea%20stigonocarpa&rft.jtitle=Journal%20of%20natural%20products%20(Washington,%20D.C.)&rft.au=Monteiro,%20Afif%20F&rft.date=2015-06-26&rft.volume=78&rft.issue=6&rft.spage=1451&rft.epage=1455&rft.pages=1451-1455&rft.issn=0163-3864&rft.eissn=1520-6025&rft_id=info:doi/10.1021/acs.jnatprod.5b00166&rft_dat=%3Cproquest_cross%3E1691597173%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1691597173&rft_id=info:pmid/26039872&rfr_iscdi=true