Loading…
Chemical constituents, the stereochemistry of 3-hydroxy furonaphthoquinones from the root bark of Newbouldialaevis Seem (Bignoniaceae), and screening against Onchocercaochengi parasites
Through bioassay-guided fractionation, 13 compounds ( 1 – 13 ) were isolated from the CH 2 Cl 2 /MeOH (1:1) extracts of the root bark of Newbouldia leavis and characterized mainly by NMR and X-ray spectroscopy. Among these, nine quinone derivatives ( 1 – 7 , 12 – 13 ), one triterpeniod ( 8 ), and th...
Saved in:
Published in: | Medicinal chemistry research 2015, Vol.24 (3), p.965-969 |
---|---|
Main Authors: | , , , |
Format: | Article |
Language: | English |
Subjects: | |
Online Access: | Get full text |
Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
cited_by | |
---|---|
cites | |
container_end_page | 969 |
container_issue | 3 |
container_start_page | 965 |
container_title | Medicinal chemistry research |
container_volume | 24 |
creator | Eyong, Kenneth O. Ketsemen, Herve L. Ghansenyuy, Salome Y. Folefoc, Gabriel N. |
description | Through bioassay-guided fractionation, 13 compounds (
1
–
13
) were isolated from the CH
2
Cl
2
/MeOH (1:1) extracts of the root bark of
Newbouldia
leavis
and characterized mainly by NMR and X-ray spectroscopy. Among these, nine quinone derivatives (
1
–
7
,
12
–
13
), one triterpeniod (
8
), and three steroids (
9
–
11
) were isolated. The stereochemistry of 3-hydroxy furonaphthoquinones isolated from this plant has been established for the first time as (2
S
,3
R
) on the basis of single X-ray crystal structure analysis and show marked
3
J
H,H
deviations from the Karplus curve from
1
H-NMR spectral analysis. The fractions together with three of the isolated compounds namely lapachol, 2-acetyl-naphtho [2,3-
b
]furan-4,9-dione, and 2-(1-hydroxyethyl)-2-acetyl-naphtho[2,3-
b
]furan-4,9-dione were screened against
Onchocerca
ochengi
parasites. Lapachol and 2-(1-hydroxyethyl)-2-acetyl-naphtho[2,3-
b
]furan-4,9-dione showed 100 % inhibition at a concentration of 5 μg/mL after 5 days. |
doi_str_mv | 10.1007/s00044-014-1173-z |
format | article |
fullrecord | <record><control><sourceid>springer</sourceid><recordid>TN_cdi_springer_journals_10_1007_s00044_014_1173_z</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>10_1007_s00044_014_1173_z</sourcerecordid><originalsourceid>FETCH-LOGICAL-s76z-278ff4ca7ee911d3b2088d9cb33836f5808ed700c957d955c7643d59738627023</originalsourceid><addsrcrecordid>eNotkMtOwzAQRSMEEqXwAey8BKmBcRzXyRIqXlJFF3QfOc4kcWntYjtA-2f8HQllNXcxZ-bqRNElhRsKIG49AKRpDDSNKRUs3h9FI8p5Gmc0geM-Q58TnrDT6Mz7FQATkPJR9DNrcaOVXBNljQ86dGiCn5DQIvEBHVo1LPjgdsTWhMXtrnL2e0fqzlkjt21o7UenjTXoSe3s5o901gZSSvc-MK_4VdpuXWm5lvipPXlD3JCre930lJYKJV5PiDQV8cohGm0aIhup-zpkYVRrFTolhx6m0WQrnfQ6oD-PTmq59njxP8fR8vFhOXuO54unl9ndPPZiuo8TkdV1qqRAzCmtWJlAllW5KhnL2LTmGWRYCQCVc1HlnCsxTVnFc8GyaSIgYeMoOZz1W9c3Q1esbOdM_7GgUAzui4P7ondfDO6LPfsFKNp88w</addsrcrecordid><sourcetype>Publisher</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Chemical constituents, the stereochemistry of 3-hydroxy furonaphthoquinones from the root bark of Newbouldialaevis Seem (Bignoniaceae), and screening against Onchocercaochengi parasites</title><source>Springer Nature</source><creator>Eyong, Kenneth O. ; Ketsemen, Herve L. ; Ghansenyuy, Salome Y. ; Folefoc, Gabriel N.</creator><creatorcontrib>Eyong, Kenneth O. ; Ketsemen, Herve L. ; Ghansenyuy, Salome Y. ; Folefoc, Gabriel N.</creatorcontrib><description>Through bioassay-guided fractionation, 13 compounds (
1
–
13
) were isolated from the CH
2
Cl
2
/MeOH (1:1) extracts of the root bark of
Newbouldia
leavis
and characterized mainly by NMR and X-ray spectroscopy. Among these, nine quinone derivatives (
1
–
7
,
12
–
13
), one triterpeniod (
8
), and three steroids (
9
–
11
) were isolated. The stereochemistry of 3-hydroxy furonaphthoquinones isolated from this plant has been established for the first time as (2
S
,3
R
) on the basis of single X-ray crystal structure analysis and show marked
3
J
H,H
deviations from the Karplus curve from
1
H-NMR spectral analysis. The fractions together with three of the isolated compounds namely lapachol, 2-acetyl-naphtho [2,3-
b
]furan-4,9-dione, and 2-(1-hydroxyethyl)-2-acetyl-naphtho[2,3-
b
]furan-4,9-dione were screened against
Onchocerca
ochengi
parasites. Lapachol and 2-(1-hydroxyethyl)-2-acetyl-naphtho[2,3-
b
]furan-4,9-dione showed 100 % inhibition at a concentration of 5 μg/mL after 5 days.</description><identifier>ISSN: 1054-2523</identifier><identifier>EISSN: 1554-8120</identifier><identifier>DOI: 10.1007/s00044-014-1173-z</identifier><language>eng</language><publisher>Boston: Springer US</publisher><subject>Biochemistry ; Biomedical and Life Sciences ; Biomedicine ; Cell Biology ; Original Research ; Pharmacology/Toxicology</subject><ispartof>Medicinal chemistry research, 2015, Vol.24 (3), p.965-969</ispartof><rights>Springer Science+Business Media New York 2014</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids></links><search><creatorcontrib>Eyong, Kenneth O.</creatorcontrib><creatorcontrib>Ketsemen, Herve L.</creatorcontrib><creatorcontrib>Ghansenyuy, Salome Y.</creatorcontrib><creatorcontrib>Folefoc, Gabriel N.</creatorcontrib><title>Chemical constituents, the stereochemistry of 3-hydroxy furonaphthoquinones from the root bark of Newbouldialaevis Seem (Bignoniaceae), and screening against Onchocercaochengi parasites</title><title>Medicinal chemistry research</title><addtitle>Med Chem Res</addtitle><description>Through bioassay-guided fractionation, 13 compounds (
1
–
13
) were isolated from the CH
2
Cl
2
/MeOH (1:1) extracts of the root bark of
Newbouldia
leavis
and characterized mainly by NMR and X-ray spectroscopy. Among these, nine quinone derivatives (
1
–
7
,
12
–
13
), one triterpeniod (
8
), and three steroids (
9
–
11
) were isolated. The stereochemistry of 3-hydroxy furonaphthoquinones isolated from this plant has been established for the first time as (2
S
,3
R
) on the basis of single X-ray crystal structure analysis and show marked
3
J
H,H
deviations from the Karplus curve from
1
H-NMR spectral analysis. The fractions together with three of the isolated compounds namely lapachol, 2-acetyl-naphtho [2,3-
b
]furan-4,9-dione, and 2-(1-hydroxyethyl)-2-acetyl-naphtho[2,3-
b
]furan-4,9-dione were screened against
Onchocerca
ochengi
parasites. Lapachol and 2-(1-hydroxyethyl)-2-acetyl-naphtho[2,3-
b
]furan-4,9-dione showed 100 % inhibition at a concentration of 5 μg/mL after 5 days.</description><subject>Biochemistry</subject><subject>Biomedical and Life Sciences</subject><subject>Biomedicine</subject><subject>Cell Biology</subject><subject>Original Research</subject><subject>Pharmacology/Toxicology</subject><issn>1054-2523</issn><issn>1554-8120</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNotkMtOwzAQRSMEEqXwAey8BKmBcRzXyRIqXlJFF3QfOc4kcWntYjtA-2f8HQllNXcxZ-bqRNElhRsKIG49AKRpDDSNKRUs3h9FI8p5Gmc0geM-Q58TnrDT6Mz7FQATkPJR9DNrcaOVXBNljQ86dGiCn5DQIvEBHVo1LPjgdsTWhMXtrnL2e0fqzlkjt21o7UenjTXoSe3s5o901gZSSvc-MK_4VdpuXWm5lvipPXlD3JCre930lJYKJV5PiDQV8cohGm0aIhup-zpkYVRrFTolhx6m0WQrnfQ6oD-PTmq59njxP8fR8vFhOXuO54unl9ndPPZiuo8TkdV1qqRAzCmtWJlAllW5KhnL2LTmGWRYCQCVc1HlnCsxTVnFc8GyaSIgYeMoOZz1W9c3Q1esbOdM_7GgUAzui4P7ondfDO6LPfsFKNp88w</recordid><startdate>2015</startdate><enddate>2015</enddate><creator>Eyong, Kenneth O.</creator><creator>Ketsemen, Herve L.</creator><creator>Ghansenyuy, Salome Y.</creator><creator>Folefoc, Gabriel N.</creator><general>Springer US</general><scope/></search><sort><creationdate>2015</creationdate><title>Chemical constituents, the stereochemistry of 3-hydroxy furonaphthoquinones from the root bark of Newbouldialaevis Seem (Bignoniaceae), and screening against Onchocercaochengi parasites</title><author>Eyong, Kenneth O. ; Ketsemen, Herve L. ; Ghansenyuy, Salome Y. ; Folefoc, Gabriel N.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-s76z-278ff4ca7ee911d3b2088d9cb33836f5808ed700c957d955c7643d59738627023</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Biochemistry</topic><topic>Biomedical and Life Sciences</topic><topic>Biomedicine</topic><topic>Cell Biology</topic><topic>Original Research</topic><topic>Pharmacology/Toxicology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Eyong, Kenneth O.</creatorcontrib><creatorcontrib>Ketsemen, Herve L.</creatorcontrib><creatorcontrib>Ghansenyuy, Salome Y.</creatorcontrib><creatorcontrib>Folefoc, Gabriel N.</creatorcontrib><jtitle>Medicinal chemistry research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Eyong, Kenneth O.</au><au>Ketsemen, Herve L.</au><au>Ghansenyuy, Salome Y.</au><au>Folefoc, Gabriel N.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chemical constituents, the stereochemistry of 3-hydroxy furonaphthoquinones from the root bark of Newbouldialaevis Seem (Bignoniaceae), and screening against Onchocercaochengi parasites</atitle><jtitle>Medicinal chemistry research</jtitle><stitle>Med Chem Res</stitle><date>2015</date><risdate>2015</risdate><volume>24</volume><issue>3</issue><spage>965</spage><epage>969</epage><pages>965-969</pages><issn>1054-2523</issn><eissn>1554-8120</eissn><abstract>Through bioassay-guided fractionation, 13 compounds (
1
–
13
) were isolated from the CH
2
Cl
2
/MeOH (1:1) extracts of the root bark of
Newbouldia
leavis
and characterized mainly by NMR and X-ray spectroscopy. Among these, nine quinone derivatives (
1
–
7
,
12
–
13
), one triterpeniod (
8
), and three steroids (
9
–
11
) were isolated. The stereochemistry of 3-hydroxy furonaphthoquinones isolated from this plant has been established for the first time as (2
S
,3
R
) on the basis of single X-ray crystal structure analysis and show marked
3
J
H,H
deviations from the Karplus curve from
1
H-NMR spectral analysis. The fractions together with three of the isolated compounds namely lapachol, 2-acetyl-naphtho [2,3-
b
]furan-4,9-dione, and 2-(1-hydroxyethyl)-2-acetyl-naphtho[2,3-
b
]furan-4,9-dione were screened against
Onchocerca
ochengi
parasites. Lapachol and 2-(1-hydroxyethyl)-2-acetyl-naphtho[2,3-
b
]furan-4,9-dione showed 100 % inhibition at a concentration of 5 μg/mL after 5 days.</abstract><cop>Boston</cop><pub>Springer US</pub><doi>10.1007/s00044-014-1173-z</doi><tpages>5</tpages></addata></record> |
fulltext | fulltext |
identifier | ISSN: 1054-2523 |
ispartof | Medicinal chemistry research, 2015, Vol.24 (3), p.965-969 |
issn | 1054-2523 1554-8120 |
language | eng |
recordid | cdi_springer_journals_10_1007_s00044_014_1173_z |
source | Springer Nature |
subjects | Biochemistry Biomedical and Life Sciences Biomedicine Cell Biology Original Research Pharmacology/Toxicology |
title | Chemical constituents, the stereochemistry of 3-hydroxy furonaphthoquinones from the root bark of Newbouldialaevis Seem (Bignoniaceae), and screening against Onchocercaochengi parasites |
url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-10T21%3A32%3A22IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-springer&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Chemical%20constituents,%20the%20stereochemistry%20of%203-hydroxy%20furonaphthoquinones%20from%20the%20root%20bark%20of%20Newbouldialaevis%20Seem%20(Bignoniaceae),%20and%20screening%20against%20Onchocercaochengi%20parasites&rft.jtitle=Medicinal%20chemistry%20research&rft.au=Eyong,%20Kenneth%20O.&rft.date=2015&rft.volume=24&rft.issue=3&rft.spage=965&rft.epage=969&rft.pages=965-969&rft.issn=1054-2523&rft.eissn=1554-8120&rft_id=info:doi/10.1007/s00044-014-1173-z&rft_dat=%3Cspringer%3E10_1007_s00044_014_1173_z%3C/springer%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-s76z-278ff4ca7ee911d3b2088d9cb33836f5808ed700c957d955c7643d59738627023%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true |