Melanogenesis-Inhibitory and Cytotoxic Activities of Diarylheptanoids from Acer nikoense Bark and Their Derivatives
| Autor: | Toshihiro Akihisa, Motohiko Ukiya, Ayano Takeda, Makoto Fukatsu, Kensuke Watanabe, Satoru Yokokawa, Takashi Kikuchi, Hiroyuki Akazawa |
|---|---|
| Rok vydání: | 2012 |
| Předmět: |
Cell Survival
Stereochemistry HL60 Melanoma Experimental Acer Bioengineering Ether Biochemistry Melanin Mice chemistry.chemical_compound Diarylheptanoids Cell Line Tumor Neoplasms Animals Humans Viability assay Molecular Biology Melanins chemistry.chemical_classification Plant Extracts Diarylheptanoid Glycoside General Chemistry General Medicine Antineoplastic Agents Phytogenic chemistry visual_art Plant Bark visual_art.visual_art_medium Molecular Medicine Bark |
| Zdroj: | Chemistry & Biodiversity. 9:1475-1489 |
| ISSN: | 1612-1872 |
| Popis: | 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). |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Plný text