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Analysis of Mumefural in Mume Fruit Extract

COSMOSIL Application Note

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Mumefural is a furylaldehyde found in heated fruit of Prunus mume, commonly referred to as Japanese or Chinese plum. It is known to improve blood flow.1 Previous research has developed HPLC methods for analysis of mumefural,2 and this application note uses these methods to extract and determine mumefural from Prunus mume flesh extract and pickled plum.

About mumefural

Mumefural (MF) is an ester of 5-hydroxymethyl-2-furfural (HMF) and citric acid, and it is abundant in the flesh of Prunus mume fruit.

The flesh extract is made by heating the fresh juice until it turns to paste, and it has been used as a folk medicine for its antibacterial and intestine-regulating properties in Japan since the Edo Period. For 1 kg of fruit, about 20 g can be extracted.

HPLC-UV for Prunus mume Flesh Extract and Pickled Plum

Prunus mume Flesh Extract

flesh extract chromatogram

Pickled Plum

pickled plum chromatogram
Conditions
ColumnCOSMOSIL 2.5C18-MS-II 2.0 mm I.D. × 50 mm
Mobile phase Gradient:
A: 0.1% formic acid in MeCN/H2O = 2 / 98
B: 0.1% formic acid in MeCN 100%
B conc. 0% → 8% (0 → 10 min.), 8% → 100% (10 → 10.1 min.), 100% (10.1 → 13 min.), 100% → 0% (13 → 13.5 min.), 0% (13.5 → 21 min.)
Temperature40°C
Flow rate0.2 mL/min
DetectionUV 280 nm
Sample Prunus mume flesh extract and pickled plum, 2 µL injection
  1. 5-Hydroxymethyl-2-furfural
    furfural
  2. Mumefural
    mumefural

Observations

Both HMF and MF were found in Prunus mume flesh extract. Neither compound was contained in the pickled plums. It is thought that these compounds are not found in pickled plums because the fruit is not heated as part of the pickling process.

HPLC-MS for Prunus mume Flesh Extract

UV 280 nm

flesh extract chromatogram

MS ESI(+) m/z 127

MS ESI(+)

MS ESI(-) m/z 299

MS ESI(-)
Conditions
ColumnCOSMOSIL 2.5C18-MS-II 2.0 mm I.D. × 50 mm
Mobile phase Gradient:
A: 0.1% formic acid in MeCN/H2O = 2 / 98
B: 0.1% formic acid in MeCN 100%
B conc. 0% → 8% (0 → 10 min.), 8% → 100% (10 → 10.1 min.), 100% (10.1 → 13 min.), 100% → 0% (13 → 13.5 min.), 0% (13.5 → 21 min.)
Temperature40°C
Flow rate0.2 mL/min
DetectionMS (ESI probe, TIC(+) or (-), M.W. 50-500), UV 280 nm
Sample Prunus mume flesh extract, 2 µL injection
  1. 5-Hydroxymethyl-2-furfural, M.W. 126, m/z=[M+H]+=127
    furfural
  2. Mumefural, M.W. 300, m/z=[M-H]-=299
    mumefural

Sample Preparation

Prunus mume flesh sample preparation
  • Flesh extract
    Mix commercially available Prunus mume fruit extract in a bottle.
  • Pickled plum
    Scrape flesh off of one pickled plum, and homogenize by crushing and mixing with a microspatula and forceps.
Dissolution
  1. Measure 150 mg of flesh sample into a 15 mL centrifuge tube.
  2. Add 5 mL of Milli-Q® water, and vortex sample to homogenize.
  3. Centrifuge at 6,000 × g at room temperature for 10 min.
Solid Phase Extraction
  1. Wash an Oasis® HLB Plus Cartridge with 5 mL of acetonitrile.
  2. Condition the cartridge with 5 mL of Milli-Q® water.
  3. Load the supernatant from the dissolution procedure onto the cartridge. Push the plunger slowly to adsorb sample.
  4. Wash the cartridge with 5 mL of Milli-Q® water, ensuring that it drains to the last drop.
  5. Elute the sample using 5 mL of acetonitrile/water (20/80) mixture.
  6. Use the above eluate as sample.

Milli-Q® is a registered trademark of Merck KGaA.
Oasis® is a registered trademark of Waters Technologies Corporation.

References

  1. Chuda Y. et al. (1999) J. Agric. Food Chem. 47(3):828-831 
  2. H. Yada et al. (2003) Journal of the Japanese Society for Food Science and Technology 50(4):188-192 

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