Melanogenesis‐Inhibitory and Cytotoxic Activities of Diarylheptanoids from Acer nikoense Bark and Their Derivatives

Abstract

Nine cyclic diarylheptanoids, 1-9, including two new compounds, i.e., 9-oxoacerogenin A (8) and 9-O-β-D-glucopyranosylacerogenin K (9), along with three acyclic diarylheptanoids, 10-12, and four phenolic compounds, 13-16, were isolated from a MeOH extract of the bark of Acer nikoense (Aceraceae). Acid hydrolysis of 9 yielded acerogenin K (17) and D-glucose. Two of the cyclic diarylheptanoids, acerogenin A (1) and (R)-acerogenin B (5), were converted to their ether and ester derivatives, 18-24 and 27-33, respectively, and to the dehydrated derivatives, 25, 26, 34, and 35. Upon evaluation of compounds 1-16 and 18-35 for their inhibitory activities against melanogenesis in B16 melanoma cells, induced with α-melanocyte-stimulating hormone (α-MSH), eight natural glycosides, i.e., six diarylheptanoid glycosides, 2-4, 6, 9, and 12, and two phenolic glycosides, 15 and 16, exhibited inhibitory activities with 24-61% reduction of melanin content at 100 μM concentration with no or almost no toxicity to the cells (88-106% of cell viability at 100 μM). In addition, when compounds 1-16 and 18-35 were evaluated for cytotoxic activity against human cancer cell lines, two natural acyclic diarylheptanoids, 10 and 11, ten ether and ester derivatives, 18-22 and 27-31, and two dehydrated derivatives, 34 and 35, exhibited potent cytotoxicities against HL60 human leukemia cell line (IC(50) 8.1-19.3 μM), and five compounds, 10, 11, 20, 29, and 30, against CRL1579 human melanoma cell line (IC(50) 10.1-18.4 μM).

The Chemistry and Biological Activities of Natural Products from Northern African Plant Families: From Taccaceae to Zygophyllaceae

“…Although the authors did not report any biological tests, this plant together with the sister species C. comosa are known to be rich sources of diarylheptanoids (e.g. Curcumin, 253 ) [ 193 , 194 ], which are known for their antioxidant [ 195 ], antiviral [ 196 ], melanogenesis-inhibitory and cytotoxic [ 197 – 200 ], anti-Leishmanial [ 201 ] and anti-Trypanosomal [ 202 ] activities, just to mention these ones.…”

Inhibitory Effect of (2R)-4-(4-hydroxyphenyl)-2-butanol 2-O-β-d-apiofuranosyl-(1→6)-β-d-glucopyranoside on RANKL-Induced Osteoclast Differentiation and ROS Generation in Macrophages

“…japonica led to the isolation of an arylbutanoid glycoside, (2R)-4-(4-hydroxyphenyl)-2-butanol 2-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (BAG). In previous pharmacological studies, BAG showed significantly inhibitory activity on lipid peroxidation as well as α-tocopherol, BHA and BHT [18] and also exhibited melanogenesisinhibitory activity with no toxicity to the B16 melanoma cells [19]. BAG was reported to show remarkable inhibitory activity against the degranulation of RBL-2H3 by antigen stimulation, which can potentially be used for the treatment of IgE-FcεRI interaction-related allergic disorders [20].…”

Acylated Triterpene Saponins from the Stem Bark of <i>Acer nikoense</i> (Aceraceae)

“…1) A variety of phenolic compounds including diarylheptanoids, [2][3][4][5][6][7][8][9][10][11] phenylbutanoids, 4,12) coumarinolignans, 13) neolignans, 14) tannins 15) and flavonoids 12) have been reported as the constituents of A. nikoense. Some of these compounds show various biological activities such as anti-oxidant, 16) anti-inflammatory, 9) hepatoprotective, 17) osteogenic, 18) vasorelaxant, 19) melanogenesis inhibitory, 11,16) nitric oxide (NO) production inhibitory 8,20) and sodium glucose cotransporter (SGLT) inhibitory activities. 10) We have been investigating edible and medicinal plants effective for the suppression of genotoxicity to discover new chemopreventive agents.…”