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 fra...

Full description

Saved in:
Bibliographic Details
Published in:Journal of agricultural and food chemistry 2006-03, Vol.54 (6), p.2123-2128
Main Authors: Jeong, Jong Tae, Moon, Jae-Hak, Park, Keun-Hyung, Shin, Chul Soo
Format: Article
Language:English
Subjects:
Animals
anticarcinogenic activity
Antineoplastic Agents - isolation & purification
Antineoplastic Agents - pharmacology
apricots
Benzopyrans - isolation & purification
Benzopyrans - pharmacology
Biological and medical sciences
Butyrates - isolation & purification
Butyrates - pharmacology
Cell Division - drug effects
Cell Line, Tumor
cell lines
chemical structure
Chromatography, High Pressure Liquid
Chromatography, Thin Layer
Food industries
Fruit - chemistry
Fruit and vegetable industries
functional foods
Fundamental and applied biological sciences. Psychology
hepatoma
Humans
Kidney Neoplasms
kidneys
Laryngeal Neoplasms
larynx
Magnetic Resonance Spectroscopy
Mice
neoplasms
Neoplasms - pathology
NIH 3T3 Cells
organic compounds
plant extracts
Prunus - chemistry
Prunus mume
Spectrometry, Mass, Fast Atom Bombardment
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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 μg/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 μg/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 μg/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. Keywords: Prunus mume fruit; cancer cell-inhibiting compound; MTT assay; structure analysis
ISSN:0021-8561
1520-5118
DOI:10.1021/jf0523770