Isolation, characterization and cytotoxic activity of benzophenone glucopyranosides from Mahkota Dewa (Phaleria macrocarpa (Scheff.) Boerl)

• Published in: Bioorganic & medicinal chemistry letters 2012-11, Vol.22 (22), p.6862-6866
• Main Authors: Zhang, Sai-Yang, Zhang, Quan-Hai, Zhao, Wen, Zhang, Xiao, Zhang, Qi, Bi, Yue-Feng, Zhang, Yan-Bing
• Format: Article
• Language: English
• Subjects: benzophenone; Benzophenone glucopyranoside; Benzophenones - chemistry; Benzophenones - isolation & purification; Benzophenones - toxicity; Bioactivity; Biological and medical sciences; Cell Line, Tumor; Cell Survival - drug effects; chemistry; cytotoxicity; Drug Screening Assays, Antitumor; esophageal neoplasms; Glucosides - chemical synthesis; Glucosides - chemistry; Glucosides - isolation & purification; Glucosides - toxicity; Glycosides - chemistry; Glycosides - isolation & purification; Glycosides - toxicity; Humans; inhibitory concentration 50; Mahkota Dewa; Medical sciences; Nuts - chemistry; Phaleria macrocarpa; Pharmacology. Drug treatments; Phenols - chemistry; Phenols - isolation & purification; Phenols - toxicity; prostatic neoplasms; Reactive Oxygen Species - metabolism; stomach neoplasms; Synthesis; Thymelaeaceae - chemistry
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2012.09.038

Two benzophenone glucopyranosides have been isolated from the nut shell parts of Mahkota Dewa, identified as Mahkoside A and Mahkoside B. A series of benzophenone glucopyranoside derivatives (compounds 3–18) were synthesized. Compound 18 has significant cytotoxicity against four different cancer lines, with IC50 less than 10μM/L. Two benzophenone glucopyranosides have been isolated from the nut shell part of Mahkota Dewa. The structures were identified as 2,4′,6-trihydroxy-4-methoxy-benzophenone-2-O-β-d-glucoside (Mahkoside A) and 2,4′,6-trihydroxy-4-methoxy-6″-acetyl-benzophenone-2-O-β-d-glucoside (Mahkoside B). Mahkoside B was recognized as a novel compound. Furthermore, a series of benzophenone glucopyranoside derivatives (compounds 3–18) were synthesized and their bioactivities were characterized. Our results demonstrated that compound 18 has significant cytotoxicity against two esophageal cancer cell lines, stomach cancer cell line and prostate cancer cell line, with IC50 less than 10μM, indicating its potential activity against cancer cells.