Methoxyflavones from Black Ginger (<i>Kaempferia parviflora</i> Wall. ex Baker) and their Inhibitory Effect on Melanogenesis in B16F10 Mouse Melanoma Cells
<i>Kaempferia parviflora</i> Wall. ex Baker (Zingiberaceae), commonly known as Thai ginseng or black ginger, is a tropical medicinal plant in many regions. It has been traditionally used to treat various ailments, including ulcers, dysentery, gout, allergies, abscesses, and osteoarthriti...
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MDPI AG
2023-03-01
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| Online Access: | https://www.mdpi.com/2223-7747/12/5/1183 |
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| author | Chen Huo Sullim Lee Min Jeong Yoo Bum Soo Lee Yoon Seo Jang Ho Kyong Kim Seulah Lee Han Yong Bae Ki Hyun Kim |
| author_facet | Chen Huo Sullim Lee Min Jeong Yoo Bum Soo Lee Yoon Seo Jang Ho Kyong Kim Seulah Lee Han Yong Bae Ki Hyun Kim |
| author_sort | Chen Huo |
| collection | DOAJ |
| description | <i>Kaempferia parviflora</i> Wall. ex Baker (Zingiberaceae), commonly known as Thai ginseng or black ginger, is a tropical medicinal plant in many regions. It has been traditionally used to treat various ailments, including ulcers, dysentery, gout, allergies, abscesses, and osteoarthritis. As part of our ongoing phytochemical study aimed at discovering bioactive natural products, we investigated potential bioactive methoxyflavones from <i>K. parviflora</i> rhizomes. Phytochemical analysis aided by liquid chromatography–mass spectrometry (LC-MS) led to the isolation of six methoxyflavones (<b>1</b>–<b>6</b>) from the <i>n</i>-hexane fraction of the methanolic extract of <i>K. parviflora</i> rhizomes. The isolated compounds were structurally determined to be 3,7-dimethoxy-5-hydroxyflavone (<b>1</b>), 5-hydroxy-7-methoxyflavone (<b>2</b>), 7,4′-dimethylapigenin (<b>3</b>), 3,5,7-trimethoxyflavone (<b>4</b>), 3,7,4′-trimethylkaempferol (<b>5</b>), and 5-hydroxy-3,7,3′,4′-tetramethoxyflavone (<b>6</b>), based on NMR data and LC-MS analysis. All of the isolated compounds were evaluated for their anti-melanogenic activities. In the activity assay, 7,4′-dimethylapigenin (<b>3</b>) and 3,5,7-trimethoxyflavone (<b>4</b>) significantly inhibited tyrosinase activity and melanin content in IBMX-stimulated B16F10 cells. In addition, structure–activity relationship analysis revealed that the methoxy group at C-5 in methoxyflavones is key to their anti-melanogenic activity. This study experimentally demonstrated that <i>K. parviflora</i> rhizomes are rich in methoxyflavones and can be a valuable natural resource for anti-melanogenic compounds. |
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| language | English |
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| spelling | doaj.art-d18369ead534457fb3719f12ea9ca4762023-11-17T08:25:16ZengMDPI AGPlants2223-77472023-03-01125118310.3390/plants12051183Methoxyflavones from Black Ginger (<i>Kaempferia parviflora</i> Wall. ex Baker) and their Inhibitory Effect on Melanogenesis in B16F10 Mouse Melanoma CellsChen Huo0Sullim Lee1Min Jeong Yoo2Bum Soo Lee3Yoon Seo Jang4Ho Kyong Kim5Seulah Lee6Han Yong Bae7Ki Hyun Kim8School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of KoreaDepartment of Life Science, College of Bio-Nano Technology, Gachon University, Seongnam 13120, Republic of KoreaSchool of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of KoreaSchool of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of KoreaSchool of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of KoreaSTL Company, Yongin 17086, Republic of KoreaSchool of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of KoreaDepartment of Chemistry, Sungkyunkwan University, Suwon 16419, Republic of KoreaSchool of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea<i>Kaempferia parviflora</i> Wall. ex Baker (Zingiberaceae), commonly known as Thai ginseng or black ginger, is a tropical medicinal plant in many regions. It has been traditionally used to treat various ailments, including ulcers, dysentery, gout, allergies, abscesses, and osteoarthritis. As part of our ongoing phytochemical study aimed at discovering bioactive natural products, we investigated potential bioactive methoxyflavones from <i>K. parviflora</i> rhizomes. Phytochemical analysis aided by liquid chromatography–mass spectrometry (LC-MS) led to the isolation of six methoxyflavones (<b>1</b>–<b>6</b>) from the <i>n</i>-hexane fraction of the methanolic extract of <i>K. parviflora</i> rhizomes. The isolated compounds were structurally determined to be 3,7-dimethoxy-5-hydroxyflavone (<b>1</b>), 5-hydroxy-7-methoxyflavone (<b>2</b>), 7,4′-dimethylapigenin (<b>3</b>), 3,5,7-trimethoxyflavone (<b>4</b>), 3,7,4′-trimethylkaempferol (<b>5</b>), and 5-hydroxy-3,7,3′,4′-tetramethoxyflavone (<b>6</b>), based on NMR data and LC-MS analysis. All of the isolated compounds were evaluated for their anti-melanogenic activities. In the activity assay, 7,4′-dimethylapigenin (<b>3</b>) and 3,5,7-trimethoxyflavone (<b>4</b>) significantly inhibited tyrosinase activity and melanin content in IBMX-stimulated B16F10 cells. In addition, structure–activity relationship analysis revealed that the methoxy group at C-5 in methoxyflavones is key to their anti-melanogenic activity. This study experimentally demonstrated that <i>K. parviflora</i> rhizomes are rich in methoxyflavones and can be a valuable natural resource for anti-melanogenic compounds.https://www.mdpi.com/2223-7747/12/5/1183<i>Kaempferia parviflora</i>ZingiberaceaeMethoxyflavonesAnti-melanogenesisB16F10 mouse melanoma cellsSAR |
| spellingShingle | Chen Huo Sullim Lee Min Jeong Yoo Bum Soo Lee Yoon Seo Jang Ho Kyong Kim Seulah Lee Han Yong Bae Ki Hyun Kim Methoxyflavones from Black Ginger (<i>Kaempferia parviflora</i> Wall. ex Baker) and their Inhibitory Effect on Melanogenesis in B16F10 Mouse Melanoma Cells Plants <i>Kaempferia parviflora</i> Zingiberaceae Methoxyflavones Anti-melanogenesis B16F10 mouse melanoma cells SAR |
| title | Methoxyflavones from Black Ginger (<i>Kaempferia parviflora</i> Wall. ex Baker) and their Inhibitory Effect on Melanogenesis in B16F10 Mouse Melanoma Cells |
| title_full | Methoxyflavones from Black Ginger (<i>Kaempferia parviflora</i> Wall. ex Baker) and their Inhibitory Effect on Melanogenesis in B16F10 Mouse Melanoma Cells |
| title_fullStr | Methoxyflavones from Black Ginger (<i>Kaempferia parviflora</i> Wall. ex Baker) and their Inhibitory Effect on Melanogenesis in B16F10 Mouse Melanoma Cells |
| title_full_unstemmed | Methoxyflavones from Black Ginger (<i>Kaempferia parviflora</i> Wall. ex Baker) and their Inhibitory Effect on Melanogenesis in B16F10 Mouse Melanoma Cells |
| title_short | Methoxyflavones from Black Ginger (<i>Kaempferia parviflora</i> Wall. ex Baker) and their Inhibitory Effect on Melanogenesis in B16F10 Mouse Melanoma Cells |
| title_sort | methoxyflavones from black ginger i kaempferia parviflora i wall ex baker and their inhibitory effect on melanogenesis in b16f10 mouse melanoma cells |
| topic | <i>Kaempferia parviflora</i> Zingiberaceae Methoxyflavones Anti-melanogenesis B16F10 mouse melanoma cells SAR |
| url | https://www.mdpi.com/2223-7747/12/5/1183 |
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