Three-dimensional
conformation of the quassinoids aligned on the
lactone substructure: (A) overlay of the
biologically inactive picrasane quassinoids and
(B) overlay of the biologically active
chaparrinon-type quassinoids. Notice the
presence of the oxymethylene bridge between C8
and C11 in the active molecules and the absence
of the oxygen bridge in the inactive molecules.
Electrostatic
potential maps of the region of the oxymethylene
bridge in (A) the biologically inactive
picrasane-type quassinoids and (B) of the
biologically active chaparrinone-type
quassinoids. Notice the increased
electronegativity potential resulting from the
presence of the oxymethylene bridge.
Electrostatic potentials range from
electronegative (purple) to electropositive
(red).
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