14065-83-9Relevant articles and documents
Antiproliferative effect and ultrastructural alterations induced by 5-O-methylembelin on Trypanosoma cruzi
Spina, Renata María,Lozano, Esteban,Barrera, Patricia Andrea,Agüero, María Belén,Tapia, Alejandro,Feresin, Gabriela Egly,Sosa, Miguel ángel
, p. 111 - 118 (2018)
Background: Embelin (EMB), obtained from Oxalis erythrorhiza Gillies ex Hooker et Arnott (Oxalidaceae), was reported against Trypanosoma cruzi and Leishmania spp. Additionally, antiprotozoan activity against Plasmodium falciparum was reported for its methylated derivative (ME). Purpose: To evaluate the potential anti-Trypanosoma cruzi activity of EMB, ME and 2,5-di-O-methylembelin (DME) and analyze the possible mechanism of action. Study design/Methods: EMB was isolated by a chromatographic method from the air-dried ground whole plant. To evaluate the effects of methylation, ME and DME were synthesized and tested against T. cruzi epimastigotes and trypomastigotes. The most active compound ME was evaluated against amastigotes. Ultrastructural alterations, ROS generation and the effect on mitochondrial activity of ME were measured. Results: Compounds inhibited the proliferation of epimastigotes. ME was also active against intracellular amastigotes. Mitochondrial alterations were observed by TEM. Additionally, ME modified the mitochondrial activity, and induced an increase in ROS levels. These evidences postulate the mitochondrion as a possible target of ME. Conclusion: ME inhibited amastigotes proliferation, thus being a potential lead compound for the treatment of Chagas’ disease.
Design, synthesis and α-glucosidase inhibition study of novel embelin derivatives
Chen, Wenhua,Chen, Xiaole,Gao, Min,Hong, Weiqian David,Jian, Rongchao,Li, Yuling,Sheng, Zhaojun,Tang, Xiaowen,Wu, Panpan,Zhang, Kun,Zhao, Denggao,Zheng, Xi
, p. 565 - 573 (2020/02/15)
Embelin is a naturally occurring para-benzoquinone isolated from Embelia ribes (Burm. f.) of the Myrsinaceae family. It was first discovered to have potent inhibitory activity (IC50 = 4.2 μM) against α-glucosidase in this study. Then, four seri
Novel series of benzoquinones with high potency against 5-lipoxygenase in human polymorphonuclear leukocytes
Filosa, Rosanna,Peduto, Antonella,Schaible, Anja M.,Krauth, Verena,Weinigel, Christina,Barz, Dagmar,Petronzi, Carmen,Bruno, Ferdinando,Roviezzo, Fiorentina,Spaziano, Giuseppe,D'Agostino, Bruno,De Rosa, Mario,Werz, Oliver
, p. 132 - 139 (2015/04/14)
5-Lipoxygenase (5-LO) is a potential target for pharmacological intervention with various inflammatory and allergic diseases. Starting from the natural dual 5-LO/microsomal prostaglandin E2 synthase (mPGES)-1 inhibitor embelin (2,5-dihydroxy-3-
Design, synthesis, and SAR of embelin analogues as the inhibitors of PAI-1 (plasminogen activator inhibitor-1)
Chen, Fanglei,Zhang, Guiping,Hong, Zebin,Lin, Zhonghui,Lei, Min,Huang, Mingdong,Hu, Lihong
, p. 2379 - 2382 (2014/05/20)
The natural product embelin was found to have PAI-1 inhibitory activity with the IC50 value of 4.94 μM. Based on the structure of embelin, a series of analogues were designed, synthesized, and evaluated for their ability to inhibit PAI-1. The SAR study on these compounds disclosed that the inhibitory potency largely depended on the hydroxyl groups at C2 and C5, and the length of the alkyl chains at C3 and C6. Compound 11 displayed the best PAI-1 inhibitory potency with the IC50 value of 0.18 μM.
Hemisynthesis of selected embelin analogs and investigation of their proapoptotic activity against cancer cells
Viault, Guillaume,Babu, Katragadda Suresh,Gautier, Fabien,Barille-Nion, Sophie,Juin, Philippe,Tasseau, Olivier,Gree, Rene
, p. 1028 - 1034 (2014/01/06)
Embelin is a natural product, inhibitor of XIAP (X-chromosome-linked Inhibitor of APoptosis) with strong proapoptotic properties on cancer cells. In order to clarify the role of two OH groups on benzoquinone core, we have prepared by hemisynthesis close analogs of embelin, where these OH groups have been replaced in a systematic manner by OMe and OAc groups. Proapoptotic activities of six embelin derivatives have been studied as single agent, or in combination with TRAIL, and their abilities to interact with XIAP have been evaluated by Surface Plasmon Biacore. Our results show that these new embelin analogs have good proapoptotic properties against selected cancer cells, often higher than the natural product itself. Further, this activity is not directly mediated by XIAP. Altogether these preliminary results demonstrate that for active embelin analogs, the two OH groups are not absolutely required for anticancer activity, opening new possibilities for the design of proapoptotic derivatives in these series.
Phytotoxic activity of quinones and resorcinolic lipid derivatives
Mizuno, Cassia S.,Rimando, Agnes M.,Duke, Stephen O.
experimental part, p. 4353 - 4355 (2011/08/05)
On the basis of the reported phytotoxic activity of sorgoleone and resorcinolic lipids identified from the root extracts of Sorghum bicolor, 8 resorcinolic lipid derivatives and 10 quinones with various side chain sizes were synthesized. The phytotoxicity of the compounds was tested against a monocot and a dicot species. The quinones were phytotoxic, whereas the resorcinolic lipids were not. Of the quinones, 2-hydroxy-5-methoxy-3- pentylcyclohexa-2,5-diene-1,4-dione, having a five-carbon side chain, showed phytotoxic activity similar to that of natural compound sorgoleone. This article not subject to U.S. Copyright. Published 2010 by the American Chemical Society.
Chemical transformation of embelin through dimerization during preparation of a decoction
Kiuchi, Fumiyuki,Suzuki, Noriko,Fukumoto, Yumiko,Goto, Yoshihisa,Mitsui, Mariko,Tsuda, Yoshisuke
, p. 1225 - 1128 (2007/10/03)
Embelin, a major constituent of Embelia ribes BURM. (Myrsinaceae) was transformed into different types of compounds through dimerization during preparation of a decoction. Two of the products are proposed to have furanylidene benzofuranone and 1,4-dibenzofurandione skeletons on the basis of spectroscopic means. The transformation of embelin in boiling water is markedly accelerated by the presence of fatty acids.
Total synthesis of maesanin and analogues
Poigny, Stephane,Guyot, Michele,Samadi, Mohammad
, p. 14791 - 14802 (2007/10/03)
An efficient total synthesis of maesanin and related quinones is reported, through direct alkylation of 1,2,4,5-tetramethoxybenzene with alkylbromides, followed by oxidation with ceric ammonium nitrate (CAN) which provokes formation of the quinone and dep
Synthesis of Natural Compounds with Alkyl-methoxy-1,4-benzoquinone Structure
Pfeifer, Jochen,Gerlach, Hans
, p. 131 - 138 (2007/10/02)
The 1,4-benzoquinones 1-7 occurring in various plants and having interesting biological properties have been synthesized from the tetrahydropyranyl ethers 17 and 21.Reaction with n-butyllithium gave selectively the ortho-lithiated compounds.These could be alkylated with the haloalkenes 13-16 and haloalkanes to give the substituted phenols 18-20 and 22-25 in high yield after methanolysis.Alkylations of the methoxyisopropylether 8 of 10-undecyn-1-ol with bromobutane and bromohexane gave 9 and 10.These alkynols could be selectively hydrogenated with Lindlar-Palladium catalyst to give the (Z)-alkenols 11 and 12 which could be converted into the bromoalkenes 13, 14 and the iodoalkenes 15, 16.Oxidation of the phenols 18-20 and 22-25 with molecular oxygen in the presence of salcomine as catalyst produced the substituted 1,4-benzoquinones 1-3 and 26-29 in high yield.Selective hydrolysis with perchloric acid converted 26-29 into the natural products 4-7. - Key Words: Tetrahydropyranyl-ethers / ortho-Lithiation / ortho-Alkylation / 1,4-Benzoquinones, alkyl-methoxy- / 1,4-Benzoquinones, alkyl-hydroxy-methoxy-
