100041-67-6Relevant articles and documents
Isolation and Identification of an Antiproliferative Compound from Fructose-Tryptophan Maillard Reaction Products
Lee, Sang Hoon,Jeong, Su Jeong,Jang, Gwi Yeong,Kim, Min Young,Hwang, In Guk,Kim, Hyun Young,Woo, Koan Sik,Hwang, Bang Yeon,Song, Jin,Lee, Junsoo,Jeong, Heon Sang
, p. 3041 - 3047 (2016)
This study was performed to isolate and identify a compound with antiproliferative activity against human stomach cancer cell lines, from fructose-tryptophan Maillard reaction products (MRPs). The MRPs, prepared from a fructose-tryptophan solution heated at 130 °C for 2 h, were fractionated into five solvent fractions: n-hexane, chloroform, ethyl acetate, butanol, and water. The highest antiproliferative activity was found in the chloroform fraction (85.93% at 200 μg/mL), and the active compound from this chloroform fraction was purified by silica gel column chromatography, TLC, and preparative HPLC. The antiproliferative activity (IC50) of the active compound was 42.24 μg/mL, and the active compound was identified as perlolyrine (C16H10N2O2) by 1H/13C NMR, DEPT, HMBC, and LC-ESI-MS. Therefore, this research may be useful in developing perlolyrine as a functional therapeutic agent.
Flazin as a Promising Nrf2 Pathway Activator
Fuda, Hirotoshi,Miyanaga, Satoshi,Furukawa, Takayuki,Umetsu, Satomi,Joko, Sae,Roan, Yuning,Suzuki, Hirotaka,Hui, Shu-Ping,Watanabe, Mitsugu,Chiba, Hitoshi
, p. 12844 - 12853 (2019)
Flazin is a β-carboline-derived alkaloid found in Japanese fermented foods. Here, the potential of flazin as an antioxidant food was studied with particular reference to its effect on the Kelch-like ECH-associated protein 1 (Keap1)-nuclear factor erythroid 2-related factor 2 (Nrf2) system in human hepatocytes (C3A). Flazin and flazin analogues including the decarboxylated derivative perlolyrine were chemically synthesized and compared with each other and with chlorogenic acid and curcumin. Among these compounds, flazin showed the lowest cytotoxicity (IC50 3-fold of the control) cytoprotection ability against a pro-oxidant, although its radical absorbance capacity was relatively low. Flazin increased the expressions of Nrf2-dependent phase II enzyme genes and their products (NQO1, GSTP, and GSH proteins). The strong cytoprotection ability of flazin associated with low log ?P (0-3) is shared by sulforaphane and 3,5-dihydroxy-4-methoxybenzyl alcohol, suggesting the potential value of flazin and flazin-rich foods for the prevention of oxidation-related health disorders.
Design and synthesis of furyl/thineyl pyrroloquinolones based on natural alkaloid perlolyrine, lead to the discovery of potent and selective PDE5 inhibitors
Zheng, Hongbo,Li, Lin,Sun, Bin,Gao, Yun,Song, Wei,Zhao, Xiaoyu,Gao, Yanhui,Xie, Zhiyu,Zhang, Nianzhao,Ji, Jianbo,Yuan, Huiqing,Lou, Hongxiang
supporting information, p. 30 - 38 (2018/03/08)
Based on perlolyrine (1), a natural alkaloid with weak PDE5 potency from the traditional Chinese aphrodisiac plant Tribulus terrestris L., a series α-substituted tetrahydro-β-carboline (THβC) derivatives were synthesized via T+BF4--mediated oxidative C–H functionalization of N-aryl THβCs with diverse potassium trifluoroborates. Following Winterfeldt oxidation afforded the corresponding furyl/thienyl pyrroloquinolones, of which 5-ethylthiophene/ethylfuran derivatives 20a–b were identified as the most potent and selective PDE5 inhibitors. Among the enantiomers, (S)-20a and (S)-20b (IC50 = 0.52 and 0.39 nM) were found to be more effective than their (R)-antipode, display favorable pharmacokinetic profiles, exert in vitro vasorelaxant effects on the isolated thoracic aorta, and exhibit in vivo efficacy in the anesthetized rabbit erectile model.
