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Molecules 2018, 23(8), 1907; https://doi.org/10.3390/molecules23081907

Isolation and Purification of Potent Growth Inhibitors from Piper methysticum Root

Graduate school for International Development and Cooperation, Hiroshima University, Hiroshima 739-8529, Japan
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Received: 10 July 2018 / Revised: 20 July 2018 / Accepted: 28 July 2018 / Published: 31 July 2018
(This article belongs to the Special Issue Discovery of Active Ingredients from Natural Products)
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Abstract

Piper methysticum (kava) root is known to possess promising weed suppressing activity. The present study was conducted to search for potent plant growth inhibitors from the root of this medicinal pepper plant. The ethyl acetate (EtOAc) extract exhibited the strongest reduction on growth of Raphanus sativus (radish) (IC50 shoot and root growth = 172.00 and 51.31 µg/mL respectively) among solvent extracts. From this active extract, nine potent growth inhibitors involved in the inhibitory activities of P. methysticum root were isolated, purified and characterized by column chromatography (CC), gas chromatography-mass spectrometry (GC-MS), electrospray ionization-mass spectrometry (ESI-MS) and nuclear magnetic resonance (NMR). The six fractions purified by CC included two flavanones: 5-hydroxy-4′,7-dimethoxyflavanone (C1) and 5,7-dihydroxy-4′-methoxy-6,8-dimethylflavanone (matteucinol, C2) and six kavalactones: 5,6-dehydro-kavain (C3), a mixture of kavain and yagonin (C4), yagonin (C5) and dihydro-5,6-dehydrokavain, 7,8-dihydrokavain, dihydromethysticin and methysticin (C6). The amounts of 5-hydroxy-4′,7-dimethoxyflavanone, matteucinol, 5,6-dehydrokavain and yangonin were 0.76, 2.50, 2.75 and 2.09 mg/g dry weight (DW), respectively. The two flavanones C1 and C2 exhibited the strongest inhibition on shoot elongation (IC50 = 120.22 and 248.03 µg/mL, respectively), whilst the two kavalactone mixtures C4 and C6 showed the highest suppression on root growth of R. sativus (IC50 = 7.70 and 15.67 µg/mL, respectively). This study was the first to report the purification and inhibitory activities of the two flavanones 5-hydroxy-4′,7-dimethoxyflavanone and matteucinol in P. methysticum root. The isolated constituents from P. methysticum root including the flavanones C1 and C2 and the mixtures C4 and C6 may possess distinct modes of action on plant growth. Findings of this study highlighted that the combinations of hexane-ethyl acetate by 9:1 and 8:2 ratios successfully purified flavanones and kavalactones in P. methysticum root. View Full-Text
Keywords: Piper methysticum L.; Raphanus sativus; growth inhibitor; flavanone; kavalactone; natural herbicide Piper methysticum L.; Raphanus sativus; growth inhibitor; flavanone; kavalactone; natural herbicide
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Van, T.M.; Xuan, T.D.; Minh, T.N.; Quan, N.V. Isolation and Purification of Potent Growth Inhibitors from Piper methysticum Root. Molecules 2018, 23, 1907.

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