Mono-tetrahydrofuran Annonaceous Acetogenins from Annona squamosa as Cytotoxic Agents and Calcium Ion Chelators

• Published in: Journal of natural products (Washington, D.C.) Vol. 71; no. 5; pp. 764 - 771
• Main Authors: Liaw, Chih-Chuang, Yang, Yu-Liang, Chen, Mei, Chang, Fang-Rong, Chen, Shu-Li, Wu, Shih-Hsiung, Wu, Yang-Chang
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society and American Society of Pharmacognosy 01.05.2008; Amer Chemical Soc; American Society of Pharmacognosy; American Chemical Society
• Subjects: acetogenin; Acetogenins - chemistry; Acetogenins - isolation & purification; Acetogenins - pharmacology; Annona - chemistry; Annona squamosa; Annonaceae; annotemoyin; anticarcinogenic activity; Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - isolation & purification; Antineoplastic Agents, Phytogenic - pharmacology; Biological and medical sciences; calcium channels; chelating agents; chemical structure; Chemistry, Medicinal; cultured cells; cytotoxicity; Drug Screening Assays, Antitumor; Female; furans; General pharmacology; Humans; Life Sciences & Biomedicine; Medical sciences; Molecular Structure; Pharmacognosy. Homeopathy. Health food; Pharmacology & Pharmacy; Pharmacology. Drug treatments; phytochemicals; Plant Sciences; Plants, Medicinal - chemistry; Science & Technology; spectral analysis; squadiolin; squafosacin; Taiwan; Taiwan; SEEDS; BISTETRAHYDROFURAN; APOPTOSIS; ABSOLUTE-CONFIGURATION; ANALOGS; LEAVES; RELATIVE CONFIGURATION; BULLATACIN; Seeds; Liver; Furan derivatives; Cytotoxicity; Medicinal plant; Calcium ion; Hepatocyte; Dicotyledones; Angiospermae; Annonaceae; Mammary gland; Acetogenin; Tumor cell; Human; Pharmacognosy; Lactone; Annona squamosa; In vitro; Biological activity; Polyketide; Cell line; Plant origin; Chelating agent; Isolation; Spermatophyta; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np0704957

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.