Isolation and Characterization of a New Compound from Prunus mume Fruit that Inhibits Cancer Cells

Abstract

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.

Extract from Prunus mume Sieb. et Zucc. Fruit Prevents LPS-induced Homotypic Aggregation of Monocytic THP-1 Cells via Suppression of Nitric Oxide Production and NF-κB Activation

“…It has long been used as a traditional remedy and health food in Korea, China, Vietnam, and Japan [6,21,26,34]. To date, a number of phytochemical, pharmacological, biological, and clinical studies on Maesil have been reported [5,7,13,16,17]. Many chemical constituents have been isolated from Maesil extract including volatile compounds [27], hydroxycinnamic acid derivatives [26], citric acid derivative (mumefural) [7], and triterpenoids [16].…”

Screening of Korean medicinal plants for possible osteoclastogenesis effects in vitro

“…The kaempferol derived from Polygonatum odoratum has been used for the treatment of chronic airway diseases [33]. Euphoria longana and Prunus mume fruit was reported to have an anti-cancer effects [34,35]. The naphthoquinone pigment, shikonin, isolated from Lithospermum erythrorhizon, has several therapeutic potential including anti-inflammatory and anti-tumor effects [36].…”

Effects of Prunus mume Siebold & Zucc. in the pacemaking activity of interstitial cells of Cajal in murine small intestine

“…(PM) is used across East Asia, particularly in Korea and Japan (1), as a traditional herbal medicine for the relief of digestive problems, fatigue and fever. PM contains a number of phenolic compounds, including phenolic acids and flavonoids (1,2), which have antioxidant and free radical scavenging activities in vivo (3)(4)(5)(6).…”

“…(PM) is used across East Asia, particularly in Korea and Japan (1), as a traditional herbal medicine for the relief of digestive problems, fatigue and fever. PM contains a number of phenolic compounds, including phenolic acids and flavonoids (1,2), which have antioxidant and free radical scavenging activities in vivo (3)(4)(5)(6). Furthermore, PM extracts exhibit many pharmacological activities, including antimicrobial (7-10), immune enhancing (11), anti-cancer (1,12,13), and anti-fatigue (14) effects, and have been demonstrated to enhance osteoclast differentiation (15) and improve blood flow (16).…”

“…PM contains a number of phenolic compounds, including phenolic acids and flavonoids (1,2), which have antioxidant and free radical scavenging activities in vivo (3)(4)(5)(6). Furthermore, PM extracts exhibit many pharmacological activities, including antimicrobial (7-10), immune enhancing (11), anti-cancer (1,12,13), and anti-fatigue (14) effects, and have been demonstrated to enhance osteoclast differentiation (15) and improve blood flow (16). Additionally, previous studies have reported that using PM extracts with probiotics inhibits the development of atopic dermatitis (17) and enhances immunity (18).…”