Mono-tetrahydrofuran annonaceous acetogenins from Annona squamosa as cytotoxic agents and calcium ion chelators.
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.
Liaw
Chih-Chuang
CC
Graduate Institute of Pharmaceutical Chemistry, China Medical University, Taichung, Taiwan.
Yang
Yu-Liang
YL
Chen
Mei
M
Chang
Fang-Rong
FR
Chen
Shu-Li
SL
Wu
Shih-Hsiung
SH
Wu
Yang-Chang
YC
D054378:Acetogenins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D031041:Annona / Q000737:chemistry*; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D005260:Female; D006801:Humans; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry*; D013624:Taiwan
D054378:Acetogenins; D000972:Antineoplastic Agents, Phytogenic