90632-20-5Relevant academic research and scientific papers
Total Synthesis of the Neuroprotective Agent Cudraisoflavone J
Lu, Qili,Harmalkar, Dipesh S.,Quan, Guofeng,Kwon, Haeun,Cho, Jungsook,Choi, Yongseok,Lee, Dongho,Lee, Kyeong
, p. 1359 - 1365 (2021/05/07)
Cudraisoflavone J (1), isolated fromCudrania tricuspidata, is a potent neuroprotective compound with a chiral center. Herein, we report the first total synthesis of racemic cudraisoflavone J (1) using a Claisen rearrangement and a Suzuki coupling reaction as the key steps. Racemic secondary alcohol was kinetically resolved to give (+)- and (?)-cudraisoflavone J with up to 97 and 88% enantiomeric excess, respectively. The modified Mosher’s method was used to elucidate the absolute configuration of naturally occurring cudraisoflavone J.
Synthesis method and uses of natural product Xanthohumol D and analogue thereof
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, (2019/12/31)
The invention discloses a synthesis method and uses of a natural product Xanthohumol D (I) and an analogue (II) thereof, wherein the structural formula is defined the specification, the novel isopentenyl chalcone compound is obtained, and Xanthohumol D has good inhibitory activity on bacillus subtilis. According to the invention, the preparation method has advantages of few process steps and easily available raw materials, and is suitable for industrial production.
Synthesis and antiangiogenic activity study of new hop chalcone Xanthohumol analogues
Nuti, Elisa,Bassani, Barbara,Camodeca, Caterina,Rosalia, Lea,Cantelmo, AnnaRita,Gallo, Cristina,Baci, Denisa,Bruno, Antonino,Orlandini, Elisabetta,Nencetti, Susanna,Noonan, Douglas M.,Albini, Adriana,Rossello, Armando
, p. 890 - 899 (2017/07/26)
Angiogenesis induction is a hallmark of cancer. Antiangiogenic properties of Xanthohumol (XN), a naturally occurring prenylated chalcone from hops, have been widely reported. Here we describe the synthesis and study the antiangiogenic activity in vitro of
Total Synthesis and in Vitro Anti-Tumor-Promoting Activities of Racemic Acetophenone Monomers from Acronychia trifoliolata
Morita, Chihiro,Kobayashi, Yukiko,Saito, Yohei,Miyake, Katsunori,Tokuda, Harukuni,Suzuki, Nobutaka,Ichiishi, Eiichiro,Lee, Kuo-Hsiung,Nakagawa-Goto, Kyoko
, p. 2890 - 2897 (2016/12/07)
Six acetophenone derivatives, acronyculatins I (1), J (2), K (3), L (4), N (5), and O (6), were recently isolated from Acronychia trifoliolata, and the structure of the known acronyculatin B (7) was revised. Because of the limited quantities of isolated p
Xanthohumol, a polyphenol chalcone present in hops, activating nrf2 enzymes to confer protection against oxidative damage in pc12 cells
Yao, Juan,Zhang, Baoxin,Ge, Chunpo,Peng, Shoujiao,Fang, Jianguo
, p. 1521 - 1531 (2015/03/05)
Xanthohumol (2a?2,4a?2,4-trihydroxy-6a?2-methoxy-3a?2-prenylchalcone, Xn), a polyphenol chalcone from hops (Humulus lupulus), has received increasing attention due to its multiple pharmacological activities. As an active component in beers, its presence has been suggested to be linked to the epidemiological observation of the beneficial effect of regular beer drinking. In this work, we synthesized Xn with a total yield of 5.0% in seven steps and studied its neuroprotective function against oxidative-stress-induced neuronal cell damage in the neuronlike rat pheochromocytoma cell line PC12. Xn displays moderate free-radical-scavenging capacity in vitro. More importantly, pretreatment of PC12 cells with Xn at submicromolar concentrations significantly upregulates a panel of phase II cytoprotective genes as well as the corresponding gene products, such as glutathione, heme oxygenase, NAD(P)H:quinone oxidoreductase, thioredoxin, and thioredoxin reductase. A mechanistic study indicates that the ?±,?2-unsaturated ketone structure in Xn and activation of the transcription factor Nrf2 are key determinants for the cytoprotection of Xn. Targeting the Nrf2 by Xn discloses a previously unrecognized mechanism underlying the biological action of Xn. Our results demonstrate that Xn is a novel small-molecule activator of Nrf2 in neuronal cells and suggest that Xn might be a potential candidate for the prevention of neurodegenerative disorders.
Synthesis of xanthohumol analogues and discovery of potent thioredoxin reductase inhibitor as potential anticancer agent
Zhang, Baoxin,Duan, Dongzhu,Ge, Chunpo,Yao, Juan,Liu, Yaping,Li, Xinming,Fang, Jianguo
, p. 1795 - 1805 (2015/04/27)
The selenoprotein thioredoxin reductases (TrxRs) are attractive targets for anticancer drugs development. Xanthohumol (Xn), a naturally occurring polyphenol chalcone from hops, has received increasing attention because of its multiple pharmacological activities. We synthesized Xn and its 43 analogues and discovered that compound 13n displayed the highest cytotoxicity toward HeLa cells (IC50 = 1.4 μM). Structure-activity relationship study indicates that the prenyl group is not necessary for cytotoxicity, and introducing electron-withdrawing group, especially on the meta-position, is favored. In addition, methylation of the phenoxyl groups generally improves the potency. Mechanistic study revealed that 13n selectively inhibits TrxR and induces reactive oxygen species and apoptosis in HeLa cells. Cells overexpressing TrxR are resistant to 13n insult, while knockdown of TrxR sensitizes cells to 13n treatment, highlighting the physiological significance of targeting TrxR by 13n. The clarification of the structural determinants for the potency would guide the design of novel potent molecules for future development.
SYNTHETIC ANALOGUES OF XANTHOHUMOL
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, (2014/10/29)
The present invention relates to novel synthetic analogues of xanthohumol and the use thereof.
A one-pot synthesis of aurones from substituted acetophenones and benzaldehydes: A concise synthesis of aureusidin
Zhao, Xiaolong,Liu, Jie,Xie, Zhixiang,Li, Ying
, p. 2217 - 2224 (2012/09/22)
A one-pot synthesis of aurones from substituted acetophenone and benzaldehyde has been developed on the basis of an improved Algar-Flynn-Oyamada reaction. By using this method, several aurones were prepared in three steps from commercial starting materials. The usefulness of this one-pot strategy was confirmed by a synthesis of aureusidin, an inhibitor of iodothyronine deiodinase, in 41% overall yield. In comparison with a two-step synthesis of this product from the same substrates, the one-pot strategy was more effective, giving a higher yield and requiring fewer and simpler operations. Georg Thieme Verlag Stuttgart New York.
Flavonoids as vasorelaxant agents: Synthesis, biological evaluation and quantitative structure activities relationship (QSAR) studies
Dong, Xiaowu,Wang, Yanming,Liu, Tao,Wu, Peng,Gao, Jiadi,Xu, Jianchao,Yang, Bo,Hu, Yongzhou
experimental part, p. 8257 - 8272 (2011/12/15)
A series of 2-(2-diethylamino)-ethoxychalcone and 6-prenyl(or its isomers)-flavanones 10a,b and 11a-g were synthesized and evaluated for their vasorelaxant activities against rat aorta rings pretreated with 1 μM phenylephrine (PE). Several compounds showe
Natural and non-natural prenylated chalcones: Synthesis, cytotoxicity and anti-oxidative activity
Vogel, Susanne,Ohmayer, Susanne,Brunner, Gabi,Heilmann, Joerg
, p. 4286 - 4293 (2008/12/20)
A general strategy for the synthesis of 3′-prenylated chalcones was established and a series of prenylated hydroxychalcones, including the hop (Humulus lupulus L.) secondary metabolites xanthohumol (1), desmethylxanthohumol (2), xanthogalenol (3), and 4-methylxanthohumol (4) were synthesized. The influence of the A-ring hydroxylation pattern on the cytotoxic activity of the prenylated chalcones was investigated in a HeLa cell line and revealed that non-natural prenylated chalcones, like 2′,3,4′,5-tetrahydroxy-6′-methoxy-3′-prenylchalcone (9, IC50 3.2 ± 0.4 μM) as well as the phase 1 metabolite of xanthohumol (1), 3-hydroxyxanthohumol (8, IC50 2.5 ± 0.5 μM), were more active in comparison to 1 (IC50 9.4 ± 1.4 μM). A comparison of the cytotoxic activity of xanthohumol (1) and 3-hydroxyxanthohumol (8) with the non-prenylated analogs helichrysetin (12, IC50 5.2 ± 0.8) and 3-hydroxyhelichrysetin (13, IC50 14.8 ± 2.1) showed that the prenyl side chain at C-3′ has an influence on the cytotoxicity against HeLa cells only for the dihydroxylated derivative. This offers interesting synthetic possibilities for the development of more potent compounds. The ORAC activity of the synthesized compounds was also investigated and revealed the highest activity for compounds 12, 4′-methylxanthohumol (4), and desmethylxanthohumol (2), with 4.4 ± 0.6, 3.8 ± 0.4, and 3.8 ± 0.5 Trolox equivalents, respectively.
