Planta Med 2008; 74 - PB154
DOI: 10.1055/s-0028-1084499

Mono-tetrahydrofuran annonaceous acetogenins from Annona squamosa as cytotoxic agents and calcium ion chelators

CC Liaw 1, 2, YL Yang 2, 3, M Chen 1, FR Chang 2, 4, SL Chen 2, SH Wu 3, YC Wu 2, 4
  • 1Graduate Institute of Pharmaceutical Chemistry, China Medical University, 91 Hsueh-Shih Rd., Taichung 40402, Taiwan
  • 2Graduate Institute of Natural Products, School of Pharmacy, Kaohsiung Medical University, 100 Shih Chuan 1st Rd., Kaohsiung 807, Taiwan
  • 3Institute of Biological Chemistry, Academia Sinica, 128 Academia Rd., Section 2, Nankang, Taipei 115, Taiwan
  • 4Center of Excellence for Environmental Medicine, Kaohsiung Medical University, 100 Shih Chuan 1st Rd., Kaohsiung 807, Taiwan

Eight new mono-tetrahydrofuran (THF)-type annonaceous acetogenins, squafosacins B, C, F, and G (1–4), squadiolins A-C (5–7), and cis-annotemoyin-1 (8), as well as eight known annonaceous acetogenins, glabranin, annotemoyins-1 and -2, bullatencin, cis-bullatencin, and uvariamicins-I, -II, and -III, were isolated from the seeds of Annona squamosa [1] by HPLC. The structures of all new isolates were elucidated using spectroscopic and chemical methods. Squadiolins A (5) and B (6) showed ng/mL potency against human Hep G2 hepatoma cells and significant cytotoxic activity against human MDA-MB-231 breast cancer cells. Squafosacin B (1) 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.

Acknowledgements: National Science Technology Program/Biotechnology and Pharmaceuticals, N.S.C., Taiwan.

References: 1. Wu, Y. C. (2006) In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Biomedical: Amsterdam, Vol. 33, pp 957–1024.