Isolation and Identification of Constituents Exhibiting Antioxidant, Antibacterial, and Antihyperuricemia Activities in <i>Piper methysticum</i> Root
The aqueous extract of kava (<i>Piper methysticum</i>) root is known as a traditional beverage for daily intake in the Western Pacific Islands, such as Fiji, Tonga, and Vanuatu, to induce relaxation and health-beneficial effects. In this study, the antioxidant, anti-hyperuricemia, and an...
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MDPI AG
2022-12-01
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| Series: | Foods |
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| Online Access: | https://www.mdpi.com/2304-8158/11/23/3889 |
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| author | Truong Ngoc Minh Truong Mai Van Tran Dang Khanh Tran Dang Xuan |
| author_facet | Truong Ngoc Minh Truong Mai Van Tran Dang Khanh Tran Dang Xuan |
| author_sort | Truong Ngoc Minh |
| collection | DOAJ |
| description | The aqueous extract of kava (<i>Piper methysticum</i>) root is known as a traditional beverage for daily intake in the Western Pacific Islands, such as Fiji, Tonga, and Vanuatu, to induce relaxation and health-beneficial effects. In this study, the antioxidant, anti-hyperuricemia, and antibacterial properties of kava root were investigated through the isolation and purification of bioactive compounds in ten fractions separated by column chromatography (CC). They included six flavonoids, 5-hydroxy-4′,7-dimethoxyflavanone (<b>C1</b>), matteucinol (<b>C2</b>), isosakuranetin (<b>C3</b>), 5,7- dimethoxyflavanone (<b>C4</b>), 2′,4′-dihydroxy-6′-methoxydihydrochalcone (in <b>MC5</b>) and alpinetin (<b>C10</b>), and seven kavalactones, 5,6-dehydrokawain (DK) (in <b>MC5</b> and <b>C6</b>), kavain (in <b>MC7</b>), yangonin (in <b>MC7</b> and <b>C8</b>), dihydro-5,6-dehydrokavain (DDK) (in <b>MC9</b>), 7,8-dihydromethysticin (in <b>MC9</b>), dihydromethysticin (in <b>MC9</b>), methysticin (in <b>MC9</b>). The chemical structures of the compounds were illustrated by the analyses of gas chromatography–mass spectrometry (GC–MS), electrospray ionization–mass spectrometry (ESI–MS), nuclear magnetic resonance (<sup>1</sup>H and <sup>13</sup>C-NMR), and X-ray diffraction. The evaluation of the free radical scavenging activity of the isolated substances via the DPPH and ABTS assays revealed that <b>C3</b> (IC<sub>50</sub>: ABTS = 76.5; DPPH = 74.8 µg/mL) possessed the strongest antioxidant property. In terms of anti-hyperuricemia activity evaluated via the xanthine oxidase inhibitory in vitro assay, the compound <b>C10</b> was the most promising inhibitor, revealing an IC<sub>50</sub> of 134.52 µg/mL. The two kavalactone mixtures in <b>MC5</b> and a pure compound <b>C6</b> inhibited the growth of bacteria <i>Listeria monocytogenes</i>, while <b>MC7</b> can constrain the development of <i>Klebsiella pneumoniae.</i> This is the first study to isolate, purify, and identify the flavonoids isosakuranetin, 2′,4′-dihydroxy-6′-methoxydihydrochalcone and alpinetin in kava root and report their pharmaceutical potential. The identified bioactive compounds showed potent antioxidant, anti-hyperuricemia, and antibacterial activity and thus can enhance the value of beverages and foods derived from kava root. |
| first_indexed | 2024-03-09T17:47:12Z |
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| last_indexed | 2024-03-09T17:47:12Z |
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| spelling | doaj.art-25604efe30644f898e42bf521a8c11e52023-11-24T11:00:17ZengMDPI AGFoods2304-81582022-12-011123388910.3390/foods11233889Isolation and Identification of Constituents Exhibiting Antioxidant, Antibacterial, and Antihyperuricemia Activities in <i>Piper methysticum</i> RootTruong Ngoc Minh0Truong Mai Van1Tran Dang Khanh2Tran Dang Xuan3Center for Research and Technology Transfer, Vietnam Academy of Science and Technology (VAST), Hanoi 122100, VietnamTransdisciplinary Science and Engineering Program, Graduate School of Advanced Science and Engineering, Hiroshima University, Hiroshima 739-8529, JapanAgricultural Genetic Institute, Pham Van Dong Street, Hanoi 122000, VietnamTransdisciplinary Science and Engineering Program, Graduate School of Advanced Science and Engineering, Hiroshima University, Hiroshima 739-8529, JapanThe aqueous extract of kava (<i>Piper methysticum</i>) root is known as a traditional beverage for daily intake in the Western Pacific Islands, such as Fiji, Tonga, and Vanuatu, to induce relaxation and health-beneficial effects. In this study, the antioxidant, anti-hyperuricemia, and antibacterial properties of kava root were investigated through the isolation and purification of bioactive compounds in ten fractions separated by column chromatography (CC). They included six flavonoids, 5-hydroxy-4′,7-dimethoxyflavanone (<b>C1</b>), matteucinol (<b>C2</b>), isosakuranetin (<b>C3</b>), 5,7- dimethoxyflavanone (<b>C4</b>), 2′,4′-dihydroxy-6′-methoxydihydrochalcone (in <b>MC5</b>) and alpinetin (<b>C10</b>), and seven kavalactones, 5,6-dehydrokawain (DK) (in <b>MC5</b> and <b>C6</b>), kavain (in <b>MC7</b>), yangonin (in <b>MC7</b> and <b>C8</b>), dihydro-5,6-dehydrokavain (DDK) (in <b>MC9</b>), 7,8-dihydromethysticin (in <b>MC9</b>), dihydromethysticin (in <b>MC9</b>), methysticin (in <b>MC9</b>). The chemical structures of the compounds were illustrated by the analyses of gas chromatography–mass spectrometry (GC–MS), electrospray ionization–mass spectrometry (ESI–MS), nuclear magnetic resonance (<sup>1</sup>H and <sup>13</sup>C-NMR), and X-ray diffraction. The evaluation of the free radical scavenging activity of the isolated substances via the DPPH and ABTS assays revealed that <b>C3</b> (IC<sub>50</sub>: ABTS = 76.5; DPPH = 74.8 µg/mL) possessed the strongest antioxidant property. In terms of anti-hyperuricemia activity evaluated via the xanthine oxidase inhibitory in vitro assay, the compound <b>C10</b> was the most promising inhibitor, revealing an IC<sub>50</sub> of 134.52 µg/mL. The two kavalactone mixtures in <b>MC5</b> and a pure compound <b>C6</b> inhibited the growth of bacteria <i>Listeria monocytogenes</i>, while <b>MC7</b> can constrain the development of <i>Klebsiella pneumoniae.</i> This is the first study to isolate, purify, and identify the flavonoids isosakuranetin, 2′,4′-dihydroxy-6′-methoxydihydrochalcone and alpinetin in kava root and report their pharmaceutical potential. The identified bioactive compounds showed potent antioxidant, anti-hyperuricemia, and antibacterial activity and thus can enhance the value of beverages and foods derived from kava root.https://www.mdpi.com/2304-8158/11/23/3889<i>Piper methysticum</i> L.antioxidant activityantibacterial activityflavonoidkavalactonebeverage |
| spellingShingle | Truong Ngoc Minh Truong Mai Van Tran Dang Khanh Tran Dang Xuan Isolation and Identification of Constituents Exhibiting Antioxidant, Antibacterial, and Antihyperuricemia Activities in <i>Piper methysticum</i> Root Foods <i>Piper methysticum</i> L. antioxidant activity antibacterial activity flavonoid kavalactone beverage |
| title | Isolation and Identification of Constituents Exhibiting Antioxidant, Antibacterial, and Antihyperuricemia Activities in <i>Piper methysticum</i> Root |
| title_full | Isolation and Identification of Constituents Exhibiting Antioxidant, Antibacterial, and Antihyperuricemia Activities in <i>Piper methysticum</i> Root |
| title_fullStr | Isolation and Identification of Constituents Exhibiting Antioxidant, Antibacterial, and Antihyperuricemia Activities in <i>Piper methysticum</i> Root |
| title_full_unstemmed | Isolation and Identification of Constituents Exhibiting Antioxidant, Antibacterial, and Antihyperuricemia Activities in <i>Piper methysticum</i> Root |
| title_short | Isolation and Identification of Constituents Exhibiting Antioxidant, Antibacterial, and Antihyperuricemia Activities in <i>Piper methysticum</i> Root |
| title_sort | isolation and identification of constituents exhibiting antioxidant antibacterial and antihyperuricemia activities in i piper methysticum i root |
| topic | <i>Piper methysticum</i> L. antioxidant activity antibacterial activity flavonoid kavalactone beverage |
| url | https://www.mdpi.com/2304-8158/11/23/3889 |
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