Xylochemical Synthesis and Biological Evaluation of Shancigusin C and Bletistrin G

Publication type:
Journal article
Metadata:
Autoren
  • Leander Geske
  • Ulrich Kauhl
  • Mohamed EM Saeed
  • Anja Schueffler
  • Eckhard Thines
  • Thomas Efferth
  • Till Opatz
Autoren-URL
https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000660415700001&DestLinkType=FullRecord&DestApp=WOS_CPL
DOI
10.3390/molecules26113224
eISSN
1420-3049
Externe Identifier
  • Clarivate Analytics Document Solution ID: SQ5SO
  • PubMed Identifier: 34072126
Ausgabe der Veröffentlichung
11
Zeitschrift
MOLECULES
Schlüsselwörter
  • shancigusin C
  • bletistrin G
  • total synthesis
  • biological activity
  • natural products
Artikelnummer
ARTN 3224
Datum der Veröffentlichung
2021
Status
Published
Titel
Xylochemical Synthesis and Biological Evaluation of Shancigusin C and Bletistrin G
Sub types
  • Article
Ausgabe der Zeitschrift
26

Data source: Web of Science (Lite)

Other metadata sources:
Abstract
<jats:p>The biological activities of shancigusin C (1) and bletistrin G (2), natural products isolated from orchids, are reported along with their first total syntheses. The total synthesis of shancigusin C (1) was conducted by employing the Perkin reaction to forge the central stilbene core, whereas the synthesis of bletistrin G (2) was achieved by the Wittig olefination followed by several regioselective aromatic substitution reactions. Both syntheses were completed by applying only renewable starting materials according to the principles of xylochemistry. The cytotoxic properties of shancigusin C (1) and bletistrin G (2) against tumor cells suggest suitability as a starting point for further structural variation.</jats:p>
Autoren
  • Leander Geske
  • Ulrich Kauhl
  • Mohamed Saeed
  • Anja Schüffler
  • Eckhard Thines
  • Thomas Efferth
  • Till Opatz
DOI
10.3390/molecules26113224
eISSN
1420-3049
Ausgabe der Veröffentlichung
11
Zeitschrift
Molecules
Sprache
en
Online publication date
2021
Paginierung
3224 - 3224
Status
Published online
Herausgeber
MDPI AG
Herausgeber URL
http://dx.doi.org/10.3390/molecules26113224
Datum der Datenerfassung
2021
Titel
Xylochemical Synthesis and Biological Evaluation of Shancigusin C and Bletistrin G
Ausgabe der Zeitschrift
26

Data source: Crossref

Abstract
The biological activities of shancigusin C (<b>1</b>) and bletistrin G (<b>2</b>), natural products isolated from orchids, are reported along with their first total syntheses. The total synthesis of shancigusin C (<b>1</b>) was conducted by employing the Perkin reaction to forge the central stilbene core, whereas the synthesis of bletistrin G (<b>2</b>) was achieved by the Wittig olefination followed by several regioselective aromatic substitution reactions. Both syntheses were completed by applying only renewable starting materials according to the principles of xylochemistry. The cytotoxic properties of shancigusin C (<b>1</b>) and bletistrin G (<b>2</b>) against tumor cells suggest suitability as a starting point for further structural variation.
Addresses
  • Department of Chemistry, Organic Chemistry Section, Johannes Gutenberg University, Duesbergweg 10-14, 55128 Mainz, Germany.
Autoren
DOI
10.3390/molecules26113224
eISSN
1420-3049
Externe Identifier
  • PubMed Identifier: 34072126
  • PubMed Central ID: PMC8198954
Funding acknowledgements
  • Bundesministerium für Bildung, Wissenschaft und Forschung: 01DG17013
  • Rhineland Palatinate Center for Natural Products Research: Rhineland Palatinate Center for Natural Products Research
Open access
true
ISSN
1420-3049
Ausgabe der Veröffentlichung
11
Zeitschrift
Molecules (Basel, Switzerland)
Schlüsselwörter
  • Cell Line, Tumor
  • Humans
  • Orchidaceae
  • Leukemia
  • Stilbenes
  • Plant Extracts
  • Antineoplastic Agents
  • Biological Products
  • Magnetic Resonance Spectroscopy
  • Drug Resistance, Multiple
  • Molecular Structure
  • Molecular Conformation
  • Drug Design
  • Drug Resistance, Neoplasm
  • Stereoisomerism
  • Chemistry, Pharmaceutical
  • Models, Chemical
  • Chemistry Techniques, Synthetic
  • Dihydrostilbenoids
Sprache
eng
Medium
Electronic
Online publication date
2021
Open access status
Open Access
Paginierung
3224
Datum der Veröffentlichung
2021
Status
Published
Publisher licence
CC BY
Datum der Datenerfassung
2021
Titel
Xylochemical Synthesis and Biological Evaluation of Shancigusin C and Bletistrin G.
Sub types
  • research-article
  • Journal Article
Ausgabe der Zeitschrift
26

Files

https://www.mdpi.com/1420-3049/26/11/3224/pdf?version=1622196179 https://europepmc.org/articles/PMC8198954?pdf=render

Data source: Europe PubMed Central

Abstract
The biological activities of shancigusin C (1) and bletistrin G (2), natural products isolated from orchids, are reported along with their first total syntheses. The total synthesis of shancigusin C (1) was conducted by employing the Perkin reaction to forge the central stilbene core, whereas the synthesis of bletistrin G (2) was achieved by the Wittig olefination followed by several regioselective aromatic substitution reactions. Both syntheses were completed by applying only renewable starting materials according to the principles of xylochemistry. The cytotoxic properties of shancigusin C (1) and bletistrin G (2) against tumor cells suggest suitability as a starting point for further structural variation.
Date of acceptance
2021
Autoren
  • Leander Geske
  • Ulrich Kauhl
  • Mohamed EM Saeed
  • Anja Schüffler
  • Eckhard Thines
  • Thomas Efferth
  • Till Opatz
Autoren-URL
https://www.ncbi.nlm.nih.gov/pubmed/34072126
DOI
10.3390/molecules26113224
eISSN
1420-3049
Externe Identifier
  • PubMed Central ID: PMC8198954
Funding acknowledgements
  • Bundesministerium für Bildung, Wissenschaft und Forschung: 01DG17013
  • Rhineland Palatinate Center for Natural Products Research: Rhineland Palatinate Center for Natural Products Research
Ausgabe der Veröffentlichung
11
Zeitschrift
Molecules
Schlüsselwörter
  • biological activity
  • bletistrin G
  • natural products
  • shancigusin C
  • total synthesis
  • Antineoplastic Agents
  • Biological Products
  • Cell Line, Tumor
  • Chemistry Techniques, Synthetic
  • Chemistry, Pharmaceutical
  • Dihydrostilbenoids
  • Drug Design
  • Drug Resistance, Multiple
  • Drug Resistance, Neoplasm
  • Humans
  • Leukemia
  • Magnetic Resonance Spectroscopy
  • Models, Chemical
  • Molecular Conformation
  • Molecular Structure
  • Orchidaceae
  • Plant Extracts
  • Stereoisomerism
  • Stilbenes
Sprache
eng
Country
Switzerland
PII
molecules26113224
Datum der Veröffentlichung
2021
Status
Published online
Datum, an dem der Datensatz öffentlich gemacht wurde
2021
Titel
Xylochemical Synthesis and Biological Evaluation of Shancigusin C and Bletistrin G.
Sub types
  • Journal Article
Ausgabe der Zeitschrift
26

Data source: PubMed

Author's licence
CC-BY
Autoren
  • Leander Geske
  • Ulrich Kauhl
  • Mohamed EM Saaed
  • Anja Schüffler
  • Eckhard Thines
  • Thomas Efferth
  • Till Opatz
Hosting institution
Universitätsbibliothek Mainz
Sammlungen
  • JGU-Publikationen
Resource version
Published version
DOI
10.3390/molecules26113224
Funding acknowledgements
  • Open Access-Publizieren Universität Mainz / Universitätsmedizin Mainz
File(s) embargoed
false
Open access
true
ISSN
1420-3049
Ausgabe der Veröffentlichung
11
Zeitschrift
Molecules
Schlüsselwörter
  • 570 Biowissenschaften
  • 570 Life sciences
Sprache
eng
Open access status
Open Access
Paginierung
3224
Datum der Veröffentlichung
2021
Public URL
https://openscience.ub.uni-mainz.de/handle/20.500.12030/6518
Herausgeber
MDPI
Herausgeber URL
https://doi.org/10.3390/molecules26113224
Datum der Datenerfassung
2021
Datum, an dem der Datensatz öffentlich gemacht wurde
2021
Zugang
Public
Titel
Xylochemical synthesis and biological evaluation of shancigusin C and bletistrin G ‡
Ausgabe der Zeitschrift
26

Files

geske_leander-xylochemical_s-20211115110748732.pdf

Data source: OPENSCIENCE.UB

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