Mono-tetrahydrofuran Annonaceous Acetogenins from Annona squamosa as Cytotoxic Agents and Calcium Ion Chelators
Resource
Journal of Natural Products, 71(5), 764-771
Journal
Planta Medica
Date Issued
2008
Date
2008
Author(s)
Liaw, Chih-Chuang
Yang, Yu-Liang
Chen, Mei
Chang, Fang-Rong
Chen, Shu-Li
Wu, Shih-Hsiung
Wu, Yang-Chang
Abstract
Eight new mono-tetrahydrofuran (THF)-type annonaceous acetogenins, squafosacins B, C, F, and G (<b>1</b>−<b>4</b>), squadiolins A−C (<b>5</b>−<b>7</b>), and <i>cis</i>-annotemoyin-1 (<b>8</b>), as well as eight known annonaceous acetogenins, glabranin, annotemoyins-1 and -2, bullatencin, <i>cis</i>-bullatencin, and uvariamicins-I, -II, and -III, were isolated from the seeds of <i>Annona squamosa</i> by HPLC. The structures of all new isolates were elucidated by using spectroscopic and chemical methods. Squadiolins A (<b>5</b>) and B (<b>6</b>) showed ng/mL potency against human Hep G2 hepatoma cells and significant cytotoxic activity against human MDA-MB-231 breast cancer cells. Squafosacin B (<b>1</b>) also exhibited significant cytotoxic activity against human Hep G2 and 3B hepatoma and MCF-7 breast cancer cells. In addition, the chelation of mono-THF acetogenins with calcium ions was investigated using isothermal titration calorimetry.
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