Passifetilactones A-E, Fatty Acid Lactones from the Fruit and Flowers of Passiflora foetida with Cytotoxic Activity.

Phytochemical investigation of the fruit and flowers of Passiflora foetida led to the isolation of 14 compounds, of which five are previously undescribed fatty acid lactones. Four 2-pyrones, passifetilactones A-D ( 1 - 4 ), and one furanone, passifetilactone E ( 5 ), were identified by analysis of spectroscopic and spectrometric data. The previously undescribed lactones were tested for cytotoxic activities against the cancer cell lines HeLa, A549, PC-3, KKU-055, and KKU-213A and two normal cell lines, Vero and MMNK-1. Passifetilactones B ( 2 ) and C ( 3 ) displayed good to mild cytotoxic activity, at IC 50 3.7-25.9 μM and 12.2-19.8 μM, respectively, against six cell lines, but were weakly active against the MMNK-1 cell line. Passifetilactones B and C ( 2 and 3 ) showed cell apoptosis induction on the KKU-055 cell line in a flow cytometry experiment. Passifetilactone D ( 4 ) is an isolation artifact produced by purification over silica gel, but we demonstrated that it can also be slowly formed within the crude EtOAc extract. This is the first investigation of the flowers and the fruit of this plant.