Open AccessMono-tetrahydrofuran Annonaceous Acetogenins from Annona squamosa as Cytotoxic Agents and Calcium Ion Chelators
Author(s) -
ChihChuang Liaw,
Yuliang Yang,
Mei Chen,
FangRong Chang,
ShuLi Chen,
Shih-Hsiung Wu,
YangChang Wu
Publication year - 2008
Publication title -
journal of natural products
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.976
H-Index - 139
eISSN - 1520-6025
pISSN - 0163-3864
DOI - 10.1021/np0704957
Subject(s) - annona squamosa , acetogenin , tetrahydrofuran , cytotoxic t cell , chemistry , stereochemistry , annonaceae , chelation , calcium , in vitro , biochemistry , biology , botany , organic chemistry , solvent
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 by HPLC. The structures of all new isolates were elucidated by 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.
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