Contrasting chemistry of fruits and leaves of two Pseudowintera species: Sesquiterpene dialdehyde cinnamates and prenylated flavonoids

Two new sesquiterpene dialdehydes, cinnamate 7 and coumarate 8, were isolated from the fruits of Pseudowintera colorata. The known sesquiterpene dialdehydes polygodial 1 and 9-deoxymuzigadial 2 were also found in these fruits, at 5% w/w compared to 0.5% in the leaves. Fruits of Pseudowintera axillaris contained no sesquiterpene dialdehyde cinnamates, even though these are present in the leaves, but did contain prenylated flavanones 11–13. Compounds 7 and 8 are further examples of the rare sesquiterpene dialdehyde cinnamate combination, found exclusively in the family Winteraceae. This is the first report of the uncommon prenylated flavanones in Winteraceae.