Isolation and characterization of a new compound from Prunus mume fruit that inhibits cancer cells.
An active compound that inhibits cancer cells was isolated from the fruit of Prunus mume, and its structure and in vitro activities were characterized. The n-hexane fraction obtained from methanol extracts exhibited the strongest inhibitory effect on the growth of cancer cells. From the n-hexane fraction, a new compound named B-1 was purified through preparative thin-layer chromatography, ODS column chromatography, and reverse phase high-performance liquid chromatography and its structure was analyzed by fast atom bombardment mass spectrometry and 1H and 13C NMR. The molecular formula of B-1 was C19H22O6 {2-hydroxy-1-[(7-hydroxy-2-oxo-2H-chromen-6-yl)methyl]-2-methylpropyl-(2Z)-3-methyl-but-e-enoate:prunate}, and the IC50 value was in the range of 39-58 microg/mL in descending order of the cancer cell lines Hep-2, SW-156, HEC-1-B, and SK-OV-3. B-1 exhibited 81-96% inhibition at a concentration level of 100 microg/mL against all cells, based on an 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide assay. However, B-1 showed little effect against normal cells with only 23% or less growth inhibition at 100 microg/mL. Thus, B-1 has a highly specific inhibitory effect against cancer cells but little effect against normal cells. When the cancer cell lines Hep-2 and SK-OV-3 were incubated with B-1 for 72 h, most of the tested cells suffered strong growth inhibition. The compound has the potential to be developed as a nutraceutical.
Bohae R&D Center, Bohae Brewery Co. Ltd., Yongin 449-171, South Korea.
Jong Tae
JT
Jeong
Jae-Hak
JH
Moon
Keun-Hyung
KH
Park
Chul Soo
CS
Shin
D000818:Animals; D000970:Antineoplastic Agents / Q000302:isolation & purification / Q000494:pharmacology; D001578:Benzopyrans / Q000302:isolation & purification* / Q000494:pharmacology; D002087:Butyrates / Q000302:isolation & purification* / Q000494:pharmacology; D002455:Cell Division / Q000187:drug effects*; D045744:Cell Line, Tumor; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D005638:Fruit / Q000737:chemistry*; D006801:Humans; D007680:Kidney Neoplasms; D007822:Laryngeal Neoplasms; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D041681:NIH 3T3 Cells; D009369:Neoplasms / Q000473:pathology*; D027861:Prunus / Q000737:chemistry*; D016339:Spectrometry, Mass, Fast Atom Bombardment
C509593:2-hydroxy-1-((7-hydroxy-2-oxo-2H-chromen-6-yl)methyl)-2-methylpropyl-(2Z)-3-methyl-but-e-enoate; D000970:Antineoplastic Agents; D001578:Benzopyrans; D002087:Butyrates