(+)-Tephrodin - A New Flavone from Tephrosia purpurea
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Date
1972Author
Heydenreich, Matthias
Koch, Andreas
Macharia, Bernard
Muiva-Mutisya, Lois
Yenesew, Abiy
Language
enMetadata
Show full item recordAbstract
Tephrosia species are widely used
in East African traditional medicinal
practice to treat various infectious
diseases. In our continued search
for antiplasmodial agents from
Tephrosia species found in Kenya a
new flavone [(+)-Tephrodin] from
the stem of T. purpurea was
isolated.1
Its 1H NMR spectrum is identical
with the spectrum reported for
tephrodin which was isolated from
T. polystachyoides.2
1 Muiva-Mutisya L., Macharia B., Heydenreich M., Koch A., Akala H.M., Derese S., Omosa L.K., Yusuf A.O., Kamau E., Yenesew, A. Phytochem. Lett., in press.
2 Vleggar R., Smalberger T.M., de Waal H.L. Tetrahedron Lett. 13 (1972) 703
However, in contrast to the
levorotatory tephrodin found by Vleggar
et al. our compound showed
dextrorotatory behaviour ([α]D20 = +4.7°).
This suggests that both compounds must
be stereoisomers.
To clarify the relative configuration of
our compound experimental data are
compared with theoretical quantum
chemical calculations (DFT B3LYP 6311G**).
For configurational and conformational
analysis the coupling constants between
H-3“ and both protons H-2“ (2.3 and 1.0
Hz, resp.) can be used: