60503-28-8Relevant academic research and scientific papers
Structures of new cyclic diarylheptanoids and inhibitors of nitric oxide production from Japanese folk medicine Acer nikoense
Morikawa, Toshio,Tao, Jing,Toguchida, Iwao,Matsuda, Hisashi,Yoshikawa, Masayuki
, p. 86 - 91 (2003)
Three new cyclic diarylheptanoids, acerosides B1 and B2 and aceroketoside, were isolated together with 20 known compounds from a Japanese folk medicine, the stem bark of Acer nikoense. The absolute stereostructures of the new compounds were determined on the basis of chemical and physicochemical evidence. In addition, the principal diarylheptanoid constituents were found to exhibit inhibitory activity on nitric oxide production in lipopolysaccharide-activated macrophages.
Melanogenesis-inhibitory and cytotoxic activities of diarylheptanoids from acer nikoense bark and their derivatives
Akihisa, Toshihiro,Takeda, Ayano,Akazawa, Hiroyuki,Kikuchi, Takashi,Yokokawa, Satoru,Ukiya, Motohiko,Fukatsu, Makoto,Watanabe, Kensuke
, p. 1475 - 1489 (2012/10/30)
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 (IC50 8.1-19.3 μM), and five compounds, 10, 11, 20, 29, and 30, against CRL1579 human melanoma cell line (IC50 10.1-18.4 μM). Copyright
Studies on the Constituents of Aceraceae Plants. V. Two Diarylheptanoid glycosides and an Arylbutanol Apiosylglucoside from Acer nikoense
Nagai, Masahiro,Kubo, Masayoshi,Takahashi, Kunio,Fujita, Masao,Inoue, Takao
, p. 1923 - 1928 (2007/10/02)
From the stem bark of Acer nikoense Maxim. (Aceraceae), three glycosides were isolated, namely aceroside III (1), C30H40O12, mp 138-141 deg C, D -98.4 deg, aceroside VI (2), C25H32O8*1/2H2O, mp 124-125 deg C, D -69.3 deg, and apiosylepirhododendrin (3), amorphous film (C21H32O11), D -59.5 deg.On acid hydrolysis, 1 yielded acerogenin A (4), apiose, glucose, and a partially hydrolyzed product 2, while 3 afforded (+)-rhododendrol (11), apiose, and glucose.Inspection of the carbon-13 nuclear magnetic resonance (13C NMR) and the PRFT-NMR spectra of 1 and 3 disclosed that they are apiosyl-(1->6)-glucosides.The proton nuclear magnetic resonance (1H NMR) spectral data of their permethylates (6 and 12) and the analytical data of methanolysis products of 6 and 12 established the structures of 1, 2 and 3 as acerogenin A 11-O-β-D-apiofuranosyl-(1->6)-β-D-glucopyranoside, acerogenin A 11-O-β-D-glucopyranoside and (+)-rhododendrol 2-O-β-D-apiofuranosyl-(1->6)-β-D-glucanopyranoside, respectively.Keywords - Acer nikoense; Aceraceae; diarylheptanoid; arylbutanol; apiosylglucoside; aceroside (III, VI); apiosylepirhododendrin; (+)-rhododendrol; PRFT-NMR
