Styryllactones from Goniothalamus tamirensis

Synthesis and crystal structure of (±)-Goniotamirenone C

“…The independent molecules are hydrogen bonded with -OHÁ Á ÁO C linkages into chains that run parallel to the a axis. This structural analysis corrects our previous assignment as the syn isomer [Meesakul et al (2020). Phytochemistry, 171, 112248-112255].…”

“…The reaction was quenched by the addition of saturated aqueous NaHCO 3 (3 mL) then extracted using EtOAc and purified by column chromatography (EtOAc/n-hexane, 2:5) to yield (AE)-Goniotamireone C (10.7 mg, 89%) as a white solid. The NMR spectroscopic data were identical to that of natural Goniotamirenone C (Meesakul et al, 2020).…”

“…Many species of Goniothalamus have been used as folk medicines for the treatment of common illnesses and as a tonic. Goniothalamus is well known as a rich source of styryllactones, with over 100 compounds isolated and identified (Meesakul et al, 2020;Jaidee et al, 2019, Bihud et al, 2019. However, chlorinated styryllactones are rarely reported in the Annonaceae family.…”

“…However, chlorinated styryllactones are rarely reported in the Annonaceae family. To the best of our knowledge, only two compounds, Parvistone A and Goniotamirenone C, have been isolated and identified from Polyalthia parviflora (Liou et al, 2014) and Goniothalamus tamirensis (Meesakul et al, 2020), respectively. Styryllactones show interesting pharmacological activities, such as cytotoxic activity against several tumor cell lines (Lan et al, 2005;Tian et al, 2006;Prawat et al, 2012), antimycobacterial (Lekphrom et al, 2009;Prawat et al, 2012) and antiplasmodial activities (Lekphrom et al, 2009;Prawat et al, 2012).…”

“…Crystals suitable for analysis by single crystal X-ray diffraction grew from slow evaporation of a 1:4 dichloromethane:methanol solution. (E)-6-Styrylpyran-2-one (1) 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ; 52.8 mg, 0.52 mmol) was added to a solution of Goniothalamin (44.0 mg, 0.44 mmol), isolated as described previously (Meesakul et al, 2020), in anhydrous benzene (5 mL) and the solution heated at reflux for 3 h. The cooled crude mixture was filtered through Celite and concentrated under reduced pressure. Purification of the residue by column chromatography (EtOAc/n-hexane, 1:5) yielded 1 (43.8 mg, 92%) as a yellow solid after evaporation of the solvent.…”