Bioactive Secondary Metabolites from Boesenbergia pandurata of Myanmar and Their Preferential Cytotoxicity against Human Pancreatic Cancer PANC-1 Cell Line in Nutrient-Deprived Medium

• Published in: Journal of natural products (Washington, D.C.) D.C.), 2007-10, Vol.70 (10), p.1582-1587
• Main Authors: Win, Nwet Nwet, Awale, Suresh, Esumi, Hiroyasu, Tezuka, Yasuhiro, Kadota, Shigetoshi
• Format: Article
• Language: English
• Subjects: anticarcinogenic activity; Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - isolation & purification; Antineoplastic Agents, Phytogenic - pharmacology; benzoic acid; Biological and medical sciences; Boesenbergia pandurata; Cell Line, Tumor; chalcones; Chalcones - chemistry; Chalcones - isolation & purification; Chalcones - pharmacology; chemical structure; cultured cells; cytotoxicity; Drug Screening Assays, Antitumor; flavanones; General pharmacology; Humans; Medical sciences; Molecular Structure; Myanmar; nicolaioidesin; pancreatic cancer; Pancreatic Neoplasms; panduratin; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; pinostrobin; Plants, Medicinal - chemistry; Rhizome - chemistry; secondary metabolites; spectral analysis; Terpenes - chemistry; Terpenes - isolation & purification; Terpenes - pharmacology; Zingiberaceae; Zingiberaceae - chemistry
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np070286m

The chloroform extract of rhizomes of Boesenbergia pandurata demonstrated marked preferential cytotoxicity against human pancreatic PANC-1 cancer cells in nutrient-deprived medium. Bioactivity-directed investigation of this extract yielded four new secondary metabolites, geranyl-2,4-dihydroxy-6-phenethylbenzoate (1), 2′,4′-dihydroxy-3′-(1′′-geranyl)-6′-methoxychalcone (2), (1′R,2′S,6′R)-2-hydroxyisopanduratin A (3), and (2R)-8-geranylpinostrobin (4), and twenty known compounds (5–24). Among the known compounds, (2S)-6-geranylpinostrobin (5), (±)-6-methoxypanduratin A (6), and (2S)-7,8-dihydro-5-hydroxy-2-methyl-2-(4′′-methyl-3′′-pentenyl)-8-phenyl-2H,6H-benzo[1,2-b:5,4-b′]dipyran-6-one (7) were isolated for the first time from a natural source. The structures of these compounds were elucidated using extensive spectroscopic techniques including CD measurements. All the isolated compounds showed varying degrees of in vitro preferential cytotoxicity against PANC-1 cells. Nicolaioidesin B (11) and panduratin A (17) were most potent, each showing a PC100 at 2.5 µM.