TY - JOUR
T1 - Methoxyflavones from Black Ginger (Kaempferia parviflora Wall. ex Baker) and their Inhibitory Effect on Melanogenesis in B16F10 Mouse Melanoma Cells
AU - Huo, Chen
AU - Lee, Sullim
AU - Yoo, Min Jeong
AU - Lee, Bum Soo
AU - Jang, Yoon Seo
AU - Kim, Ho Kyong
AU - Lee, Seulah
AU - Bae, Han Yong
AU - Kim, Ki Hyun
N1 - Publisher Copyright:
© 2023 by the authors.
PY - 2023/3
Y1 - 2023/3
N2 - Kaempferia parviflora 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 K. parviflora rhizomes. Phytochemical analysis aided by liquid chromatography–mass spectrometry (LC-MS) led to the isolation of six methoxyflavones (1–6) from the n-hexane fraction of the methanolic extract of K. parviflora rhizomes. The isolated compounds were structurally determined to be 3,7-dimethoxy-5-hydroxyflavone (1), 5-hydroxy-7-methoxyflavone (2), 7,4′-dimethylapigenin (3), 3,5,7-trimethoxyflavone (4), 3,7,4′-trimethylkaempferol (5), and 5-hydroxy-3,7,3′,4′-tetramethoxyflavone (6), 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 (3) and 3,5,7-trimethoxyflavone (4) 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 K. parviflora rhizomes are rich in methoxyflavones and can be a valuable natural resource for anti-melanogenic compounds.
AB - Kaempferia parviflora 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 K. parviflora rhizomes. Phytochemical analysis aided by liquid chromatography–mass spectrometry (LC-MS) led to the isolation of six methoxyflavones (1–6) from the n-hexane fraction of the methanolic extract of K. parviflora rhizomes. The isolated compounds were structurally determined to be 3,7-dimethoxy-5-hydroxyflavone (1), 5-hydroxy-7-methoxyflavone (2), 7,4′-dimethylapigenin (3), 3,5,7-trimethoxyflavone (4), 3,7,4′-trimethylkaempferol (5), and 5-hydroxy-3,7,3′,4′-tetramethoxyflavone (6), 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 (3) and 3,5,7-trimethoxyflavone (4) 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 K. parviflora rhizomes are rich in methoxyflavones and can be a valuable natural resource for anti-melanogenic compounds.
KW - Anti-melanogenesis
KW - B16F10 mouse melanoma cells
KW - Kaempferia parviflora
KW - Methoxyflavones
KW - SAR
KW - Zingiberaceae
UR - http://www.scopus.com/inward/record.url?scp=85150158395&partnerID=8YFLogxK
U2 - 10.3390/plants12051183
DO - 10.3390/plants12051183
M3 - Article
AN - SCOPUS:85150158395
SN - 2223-7747
VL - 12
JO - Plants
JF - Plants
IS - 5
M1 - 1183
ER -