A new ursane-type triterpene oxoglucopyranoside from Crossopteryx febrifuga

Publikationstyp:
Zeitschriftenaufsatz
Metadaten:
Autoren
  • Modjinan Kayangar
  • Raymond Ngansop Nono
  • Jonas Kuehlborn
  • Roland Tchuenguem
  • Beaudelaire K Ponou
  • Kristina Jenett-Siems
  • Remy B Teponno
  • Jean R Dzoyem
  • Till Opatz
  • Matthias F Melzig
  • Leon A Tapondjou
Autoren-URL
https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000494939800002&DestLinkType=FullRecord&DestApp=WOS_CPL
DOI
10.1515/znc-2019-0113
eISSN
1865-7125
Externe Identifier
  • Clarivate Analytics Document Solution ID: JK6GN
  • PubMed Identifier: 31525160
ISSN
0939-5075
Ausgabe der Veröffentlichung
11-12
Zeitschrift
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION C-A JOURNAL OF BIOSCIENCES
Schlüsselwörter
  • 3 beta-D-3-oxo-glucopyranosyl-ursa-12
  • antibacterial properties
  • Crossopteryx febrifuga
  • 20(30)-diene-27
  • 28-dioic acid
Paginierung
289 - 293
Datum der Veröffentlichung
2019
Status
Published
Titel
A new ursane-type triterpene oxoglucopyranoside from <i>Crossopteryx febrifuga</i>
Sub types
  • Article
Ausgabe der Zeitschrift
74

Datenquelle: Web of Science (Lite)

Andere Metadatenquellen:
Abstract
<jats:title>Abstract</jats:title> <jats:p>A new saponin, 3-<jats:italic>O</jats:italic>-β-<jats:sc>d</jats:sc>-3-oxo-glucopyranosyl-ursa-12,20(30)-diene-27,28-dioic acid (<jats:bold>1</jats:bold>), was isolated from the methanol extract of stem bark of <jats:italic>Crossopteryx febrifuga</jats:italic> together with the known 3β-<jats:sc>d</jats:sc>-glucopyranosyl-ursa-12,20(30)-diene-27,28-dioic acid (<jats:bold>2</jats:bold>), shanzhiside methyl ester (<jats:bold>3</jats:bold>), shanzhiside (<jats:bold>4</jats:bold>), β-sitosterol (<jats:bold>5</jats:bold>), β-sitosterol-3-<jats:italic>O</jats:italic>-β-<jats:sc>d</jats:sc>-glucopyranoside (<jats:bold>6</jats:bold>), ursa-12,20(30)-diene-27,28-dioic acid (<jats:bold>7</jats:bold>), hederagenin (<jats:bold>8</jats:bold>), and oleanolic acid (<jats:bold>9</jats:bold>). The structures were established by comprehensive interpretation of their spectral data 1D- (<jats:sup>1</jats:sup>H and <jats:sup>13</jats:sup>C), 2D-NMR (<jats:sup>1</jats:sup>H-<jats:sup>1</jats:sup>H COSY, HMQC, HMBC), spectroscopic, and electrospray ionisation time-of-flight mass spectrometry analysis. The isolated compounds and extracts were screened for their antibacterial properties. Although the EtOAc and <jats:italic>n</jats:italic>-BuOH extracts exhibited considerable antibacterial activity against <jats:italic>Pseudomonas aeruginosa</jats:italic> with minimum inhibitory concentration (MIC) value of 32 μg/mL, compounds <jats:bold>2</jats:bold> and <jats:bold>8</jats:bold> showed moderate activity against <jats:italic>Enterococcus faecalis</jats:italic> with MIC values of 256 and 128 μg/mL, respectively. The new compound (<jats:bold>1</jats:bold>) exhibited a moderate antibacterial activity against <jats:italic>Staphylococcus aureus</jats:italic> with an MIC value of 512 μg/mL.</jats:p>
Autoren
  • Modjinan Kayangar
  • Raymond Ngansop Nono
  • Jonas Kühlborn
  • Roland Tchuenguem
  • Beaudelaire K Ponou
  • Kristina Jenett-Siems
  • Rémy B Teponno
  • Jean P Dzoyem
  • Till Opatz
  • Matthias F Melzig
  • Léon A Tapondjou
DOI
10.1515/znc-2019-0113
eISSN
1865-7125
ISSN
0939-5075
Ausgabe der Veröffentlichung
11-12
Zeitschrift
Zeitschrift für Naturforschung C
Sprache
en
Online publication date
2019
Paginierung
289 - 293
Datum der Veröffentlichung
2019
Status
Published
Herausgeber
Walter de Gruyter GmbH
Herausgeber URL
http://dx.doi.org/10.1515/znc-2019-0113
Datum der Datenerfassung
2023
Titel
A new ursane-type triterpene oxoglucopyranoside from <i>Crossopteryx febrifuga</i>
Ausgabe der Zeitschrift
74

Datenquelle: Crossref

Abstract
A new saponin, 3-O-β-d-3-oxo-glucopyranosyl-ursa-12,20(30)-diene-27,28-dioic acid (1), was isolated from the methanol extract of stem bark of Crossopteryx febrifuga together with the known 3β-d-glucopyranosyl-ursa-12,20(30)-diene-27,28-dioic acid (2), shanzhiside methyl ester (3), shanzhiside (4), β-sitosterol (5), β-sitosterol-3-O-β-d-glucopyranoside (6), ursa-12,20(30)-diene-27,28-dioic acid (7), hederagenin (8), and oleanolic acid (9). The structures were established by comprehensive interpretation of their spectral data 1D- (1H and 13C), 2D-NMR (1H-1H COSY, HMQC, HMBC), spectroscopic, and electrospray ionisation time-of-flight mass spectrometry analysis. The isolated compounds and extracts were screened for their antibacterial properties. Although the EtOAc and n-BuOH extracts exhibited considerable antibacterial activity against Pseudomonas aeruginosa with minimum inhibitory concentration (MIC) value of 32 μg/mL, compounds 2 and 8 showed moderate activity against Enterococcus faecalis with MIC values of 256 and 128 μg/mL, respectively. The new compound (1) exhibited a moderate antibacterial activity against Staphylococcus aureus with an MIC value of 512 μg/mL.
Addresses
  • Department of Chemistry, Faculty of Science, University of Dschang, P.O. Box 67, Dschang, Cameroon.
Autoren
  • Modjinan Kayangar
  • Raymond Ngansop Nono
  • Jonas Kühlborn
  • Roland Tchuenguem
  • Beaudelaire K Ponou
  • Kristina Jenett-Siems
  • Rémy B Teponno
  • Jean P Dzoyem
  • Till Opatz
  • Matthias F Melzig
  • Léon A Tapondjou
DOI
10.1515/znc-2019-0113
eISSN
1865-7125
Externe Identifier
  • PubMed Identifier: 31525160
Open access
false
ISSN
0939-5075
Ausgabe der Veröffentlichung
11-12
Zeitschrift
Zeitschrift fur Naturforschung. C, Journal of biosciences
Schlüsselwörter
  • Bacteria
  • Rubiaceae
  • Triterpenes
  • Glucosides
  • Microbial Sensitivity Tests
  • Carbohydrate Conformation
  • Proton Magnetic Resonance Spectroscopy
  • Carbon-13 Magnetic Resonance Spectroscopy
Sprache
eng
Medium
Print
Paginierung
289 - 293
Datum der Veröffentlichung
2019
Status
Published
Datum der Datenerfassung
2019
Titel
A new ursane-type triterpene oxoglucopyranoside from Crossopteryx febrifuga.
Sub types
  • Journal Article
Ausgabe der Zeitschrift
74

Datenquelle: Europe PubMed Central

Abstract
A new saponin, 3-O-β-d-3-oxo-glucopyranosyl-ursa-12,20(30)-diene-27,28-dioic acid (1), was isolated from the methanol extract of stem bark of Crossopteryx febrifuga together with the known 3β-d-glucopyranosyl-ursa-12,20(30)-diene-27,28-dioic acid (2), shanzhiside methyl ester (3), shanzhiside (4), β-sitosterol (5), β-sitosterol-3-O-β-d-glucopyranoside (6), ursa-12,20(30)-diene-27,28-dioic acid (7), hederagenin (8), and oleanolic acid (9). The structures were established by comprehensive interpretation of their spectral data 1D- (1H and 13C), 2D-NMR (1H-1H COSY, HMQC, HMBC), spectroscopic, and electrospray ionisation time-of-flight mass spectrometry analysis. The isolated compounds and extracts were screened for their antibacterial properties. Although the EtOAc and n-BuOH extracts exhibited considerable antibacterial activity against Pseudomonas aeruginosa with minimum inhibitory concentration (MIC) value of 32 μg/mL, compounds 2 and 8 showed moderate activity against Enterococcus faecalis with MIC values of 256 and 128 μg/mL, respectively. The new compound (1) exhibited a moderate antibacterial activity against Staphylococcus aureus with an MIC value of 512 μg/mL.
Date of acceptance
2019
Autoren
  • Modjinan Kayangar
  • Raymond Ngansop Nono
  • Jonas Kühlborn
  • Roland Tchuenguem
  • Beaudelaire K Ponou
  • Kristina Jenett-Siems
  • Rémy B Teponno
  • Jean P Dzoyem
  • Till Opatz
  • Matthias F Melzig
  • Léon A Tapondjou
Autoren-URL
https://www.ncbi.nlm.nih.gov/pubmed/31525160
DOI
10.1515/znc-2019-0113
eISSN
1865-7125
Ausgabe der Veröffentlichung
11-12
Zeitschrift
Z Naturforsch C J Biosci
Schlüsselwörter
  • 3β-d-3-oxo-glucopyranosyl-ursa-12,20(30)-diene-27,28-dioic acid
  • Crossopteryx febrifuga
  • antibacterial properties
  • Bacteria
  • Carbohydrate Conformation
  • Carbon-13 Magnetic Resonance Spectroscopy
  • Glucosides
  • Microbial Sensitivity Tests
  • Proton Magnetic Resonance Spectroscopy
  • Rubiaceae
  • Triterpenes
Sprache
eng
Country
Germany
Paginierung
289 - 293
PII
/j/znc.ahead-of-print/znc-2019-0113/znc-2019-0113.xml
Datum der Veröffentlichung
2019
Status
Published
Datum, an dem der Datensatz öffentlich gemacht wurde
2020
Titel
A new ursane-type triterpene oxoglucopyranoside from Crossopteryx febrifuga.
Sub types
  • Journal Article
Ausgabe der Zeitschrift
74

Datenquelle: PubMed

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