Cytotoxic labdane diterpenes and bisflavonoid atropisomers from leaves of Araucaria bidwillii

Sherif S. Ebada, Aya N. Talaat, Rola M. Labib, Attila Mándi, T. Kurtán, Werner E.G. Müller, Abdel Nasser Singab, Peter Proksch

Research output: Article

3 Citations (Scopus)

Abstract

Chemical investigation of a methanolic extract of leaves from Araucaria bidwillii (Araucariaceae) from Egypt afforded four new labdane diterpenoidal metabolites (1–4) together with one known diterpene, 7-oxocallitrisic acid (5), two triterpenoidal metabolites, 2-O-acetyl-11-keto-boswellic acid (6) and β-sitosterol-3-O-glucopyranoside (7), phloretic acid (8), and two methylated bisflavonoids, agathisflavone-4′,7,7″-trimethyl ether (9) and cupressuflavone-4′,7,7″-trimethyl ether (10). The new metabolites 1–4 were unambiguously identified by applying extensive 1D and 2D NMR spectroscopic studies as well as HRESIMS. The relative and absolute configurations of 1–4 were determined using ROESY and the modified Mosher's method, respectively. All isolated compounds were assessed for their antimicrobial, antitubercular and cytotoxic activities. Among the tested compounds, the new labdane diterpenes 1–4 revealed significant cytotoxic activity against mouse lymphoma L5178Y cell line with IC50 values ranging from 1.4 to 12.9 μM, respectively.

Original languageEnglish
Pages (from-to)3048-3055
Number of pages8
JournalTetrahedron
Volume73
Issue number21
DOIs
Publication statusPublished - jan. 1 2017

Fingerprint

Diterpenes
Metabolites
Ether
Egypt
Inhibitory Concentration 50
Lymphoma
Cell Line
Acids
Cells
Nuclear magnetic resonance
acetyl-11-ketoboswellic acid
phloretic acid
sitosterol-3-O-glucopyranoside
labdane
agathisflavone
cupressuflavone

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Ebada, S. S., Talaat, A. N., Labib, R. M., Mándi, A., Kurtán, T., Müller, W. E. G., ... Proksch, P. (2017). Cytotoxic labdane diterpenes and bisflavonoid atropisomers from leaves of Araucaria bidwillii. Tetrahedron, 73(21), 3048-3055. https://doi.org/10.1016/j.tet.2017.04.015

Cytotoxic labdane diterpenes and bisflavonoid atropisomers from leaves of Araucaria bidwillii. / Ebada, Sherif S.; Talaat, Aya N.; Labib, Rola M.; Mándi, Attila; Kurtán, T.; Müller, Werner E.G.; Singab, Abdel Nasser; Proksch, Peter.

In: Tetrahedron, Vol. 73, No. 21, 01.01.2017, p. 3048-3055.

Research output: Article

Ebada, SS, Talaat, AN, Labib, RM, Mándi, A, Kurtán, T, Müller, WEG, Singab, AN & Proksch, P 2017, 'Cytotoxic labdane diterpenes and bisflavonoid atropisomers from leaves of Araucaria bidwillii', Tetrahedron, vol. 73, no. 21, pp. 3048-3055. https://doi.org/10.1016/j.tet.2017.04.015
Ebada, Sherif S. ; Talaat, Aya N. ; Labib, Rola M. ; Mándi, Attila ; Kurtán, T. ; Müller, Werner E.G. ; Singab, Abdel Nasser ; Proksch, Peter. / Cytotoxic labdane diterpenes and bisflavonoid atropisomers from leaves of Araucaria bidwillii. In: Tetrahedron. 2017 ; Vol. 73, No. 21. pp. 3048-3055.
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