Genomes and Genes
Summary: 7-Hydroxycoumarins. Substances present in many plants, especially umbelliferae. Umbelliferones are used in sunscreen preparations and may be mutagenic. Their derivatives are used in liver therapy, as reagents, plant growth factors, sunscreens, insecticides, parasiticides, choleretics, spasmolytics, etc.
- Kai K, Shimizu B, Mizutani M, Watanabe K, Sakata K. Accumulation of coumarins in Arabidopsis thaliana. Phytochemistry. 2006;67:379-86 pubmed..thaliana are strongly dependent on the 3'-hydroxylation of p-coumarate units catalyzed by CYP98A3. We also found that the level of skimmin, a beta-d-glucopyranoside of umbelliferone, was slightly increased in the mutant roots. ..
- Gaidukov L, Tawfik D. The development of human sera tests for HDL-bound serum PON1 and its lipolactonase activity. J Lipid Res. 2007;48:1637-46 pubmed..80). These new tests indicate the levels and activity of PON1 in a physiologically relevant context as well as the levels and quality of the HDL particles with which the enzyme is associated. ..
- Jiménez Orozco F, Rosales A, Vega López A, Domínguez López M, García Mondragón M, Maldonado Espinoza A, et al. Differential effects of esculetin and daphnetin on in vitro cell proliferation and in vivo estrogenicity. Eur J Pharmacol. 2011;668:35-41 pubmed publisher..Daphnetin-based antiproliferative selectivity with MCF-7 cells showed that daphnetin is a promising antitumoral agent also acting on estrogen dependent tumors. ..
- Kaneko T, Tahara S, Takabayashi F. Suppression of lipid hydroperoxide-induced oxidative damage to cellular DNA by esculetin. Biol Pharm Bull. 2003;26:840-4 pubmed
- Sollai F, Zucca P, Sanjust E, Steri D, Rescigno A. Umbelliferone and esculetin: inhibitors or substrates for polyphenol oxidases?. Biol Pharm Bull. 2008;31:2187-93 pubmed..A possible role of PPO in the esculetin fate along biosynthesis pathway of coumarin derivatives is also discussed. ..
- Masamoto Y, Ando H, Murata Y, Shimoishi Y, Tada M, Takahata K. Mushroom tyrosinase inhibitory activity of esculetin isolated from seeds of Euphorbia lathyris L. Biosci Biotechnol Biochem. 2003;67:631-4 pubmed..The structure-activity relationships among five esculetin analogs suggest that hydroxyl groups at the C6 and C7 positions of the coumarin skeleton played an important role in the expression of tyrosinase inhibitory activity. ..
- Rosenberg D, Roque H, Kappas A. A fluorometric method for measuring ethoxycoumarin O-deethylase activity by reversed-phase high performance liquid chromatography. Anal Biochem. 1990;191:354-8 pubmed..The wide range of linearity afforded by this method allows a reliable estimation of cytochrome P450-dependent function in samples containing varying concentrations of protein. ..
- Ramesh B, Pugalendi K. Effect of umbelliferone on tail tendon collagen and haemostatic function in streptozotocin-diabetic rats. Basic Clin Pharmacol Toxicol. 2007;101:73-7 pubmed..e. collagen related parameters, in the tail tendon, which indicates recovery from the risk (recovery of animals from the risk of complications) of collagen-mediated diabetic polyneuropathy and diabetic nephropathy. ..
- Kim H, Yu Y, Park H, Lee Y. HIV gp41 binding phenolic components from Fraxinus sieboldiana var. angustata. Planta Med. 2002;68:1034-6 pubmed..1 mg/ml and 0.5 mg/ml, respectively. Calceolarioside A ( 1), calceolarioside B ( 2), acteoside ( 3), and (-)-olivil ( 8) were isolated for the first time from this plant...
- Pfeiffer E, Metzler M. Effect of bisphenol A on drug metabolising enzymes in rat hepatic microsomes and precision-cut rat liver slices. Arch Toxicol. 2004;78:369-77 pubmed..In conclusion, this study has shown that BPA causes a selective and irreversible inhibition of certain CYP forms and interferes with the conjugation of other drugs. ..
- Dhalwal K, Shinde V, Mahadik K, Namdeo A. Rapid densitometric method for simultaneous analysis of umbelliferone, psoralen, and eugenol in herbal raw materials using HPTLC. J Sep Sci. 2007;30:2053-8 pubmed..It can be used for routine quality control of herbal raw materials as well as formulations containing any or all of these compounds. ..
- Huang G. Synthesis and stability assay of 4-methylumbelliferyl (1-->3)-beta-D-pentaglucoside. J Enzyme Inhib Med Chem. 2009;24:453-6 pubmed..Activity assays with beta-glucosidase indicated that compound 3 was much more stable than the corresponding pentasaccharide. ..
- Joseph K, Moser A, Basiaga S, Schiel J, Hage D. Evaluation of alternatives to warfarin as probes for Sudlow site I of human serum albumin: characterization by high-performance affinity chromatography. J Chromatogr A. 2009;1216:3492-500 pubmed publisher..These results also provided information on how the major structural components of warfarin contribute to the binding of this drug at Sudlow site I. ..
- Liu J, Tian J, Li Y, Yao X, Hu Z, Chen X. Binding of the bioactive component daphnetin to human serum albumin demonstrated using tryptophan fluorescence quenching. Macromol Biosci. 2004;4:520-5 pubmed..In addition, the binding distance between daphnetin and HSA was obtained (4.02 nm) based on the Forster energy transfer theory. ..
- Vasconcelos J, Teixeira M, Barbosa Filho J, Agra M, Nunes X, Giulietti A, et al. Effects of umbelliferone in a murine model of allergic airway inflammation. Eur J Pharmacol. 2009;609:126-31 pubmed publisher..The investigation of the mechanisms of action of this molecule may contribute for the development of new drugs for the treatment of asthma. ..
- Martignoni M, Monshouwer M, de Kanter R, Pezzetta D, Moscone A, Grossi P. Phase I and phase II metabolic activities are retained in liver slices from mouse, rat, dog, monkey and human after cryopreservation. Toxicol In Vitro. 2004;18:121-8 pubmed..Finally, cryopreserved liver slices from mouse, rat, dog, monkey and human with good phase I and II metabolism activities are a useful in vitro tool to compare metabolite profiles of new chemical entities between species. ..
- Neeley E, Fritch G, Fuller A, Wolfe J, Wright J, FLURKEY W. Variations in IC(50) values with purity of mushroom tyrosinase. Int J Mol Sci. 2009;10:3811-23 pubmed publisher..Organic solvents (DMSO and ethanol) had IC(50) values that were similar for some of the tyrosinase samples. Depending of the source of tyrosinase and choice of inhibitor, variations in IC(50) values were observed. ..
- Abu Mraheil M, Heisig A, Heisig P. An improved assay for the detection of alterations in bacterial DNA supercoiling in vivo. Pharmazie. 2013;68:541-8 pubmed
- Gagnaire B, Geffard O, Noury P, Garric J. In vivo indirect measurement of cytochrome P450-associated activities in freshwater gastropod molluscs. Environ Toxicol. 2010;25:545-53 pubmed publisher..Such an in vivo assay must be further developed to be valuably used to screen the exposure of gastropod species to CYP inducer chemicals and its consequences in terms of fitness of the organisms and of the population. ..
- Kharasch E, Hankins D, Taraday J. Single-dose methoxsalen effects on human cytochrome P-450 2A6 activity. Drug Metab Dispos. 2000;28:28-33 pubmed..Alternative doses, timing, and/or routes of methoxsalen administration are required for greater, longer, and more reproducible CYP2A6 inhibition than that provided by single-dose methoxsalen. ..
- Mercolini L, Mandrioli R, Ferranti A, Sorella V, Protti M, Epifano F, et al. Quantitative evaluation of auraptene and umbelliferone, chemopreventive coumarins in citrus fruits, by HPLC-UV-FL-MS. J Agric Food Chem. 2013;61:1694-701 pubmed publisher..Thus, this approach is suitable for the identification and simultaneous quantitation of auraptene and umbelliferone in citrus fruits, with the aim of evaluating their nutraceutical potential. ..
- Sinko G, Bosak A, Kovarik Z, Simeon Rudolf V. Structure-inhibition relationships in the interaction of butyrylcholinesterase with bambuterol, haloxon and their leaving groups. Chem Biol Interact. 2005;157-158:421-3 pubmed
- Lee M, Chou F, Tseng T, Hsieh M, Lin M, Wang C. Hibiscus protocatechuic acid or esculetin can inhibit oxidative LDL induced by either copper ion or nitric oxide donor. J Agric Food Chem. 2002;50:2130-6 pubmed..Additionally, their nontoxic characteristics elevated the possibility for their use in the daily diet; and should further prevent atherosclerosis effectively...
- Ekiert H, Abou Mandour A, Czygan F. Accumulation of biologically active furanocoumarins in Ruta graveolens ssp. divaricata (Tenore) Gams in vitro culture. Pharmazie. 2005;60:66-8 pubmed..3, 76.2 and 84.0mg/100g d.w., respectively) and maximum total content of all metabolites (283.4 mg/100 g d.w.), obtained on 35th culture day, are interesting from practical point of view...
- Cunha E, Pinto P, Carvalho J, Saraiva M. Automated carboxylesterase assay for the evaluation of ionic liquids' human toxicity. J Hazard Mater. 2013;244-245:563-9 pubmed publisher..0%, n=10). At the same time a reduction of costs was attained by reduced consumption of reagents and minimal effluent production (2 mL per cycle). ..
- Pachernik J, Hampl A, Soucek K, Kovaríková M, Andrysik Z, Hofmanova J, et al. Multiple biological effects of inhibitors of arachidonic acid metabolism on human keratinocytes. Arch Dermatol Res. 2002;293:626-33 pubmed..Our findings indicate that, in addition to their ability to inhibit cell proliferation and to induce apoptosis, lipoxygenase inhibitors and/or ETYA may also elicit other important physiological responses in HaCaT keratinocytes. ..
- Liu X, Xia Y, Fang Y, Zou L, Liu L. [Interaction between bovine serum albumin and umbelliferone with/without metal ions of Cu2+ or Zn2+]. Guang Pu Xue Yu Guang Pu Fen Xi. 2005;25:1301-5 pubmed..The interaction of the umbelliferone-BSA was driven mainly by electrostatic force which was enhanced by Cu2+ and Zn2+, thus the contribution of AH to AG increased in the presence of metal ions. ..
- Elinos Báez C, Leon F, Santos E. Effects of coumarin and 7OH-coumarin on bcl-2 and Bax expression in two human lung cancer cell lines in vitro. Cell Biol Int. 2005;29:703-8 pubmed..We conclude that 7-OHC is a more potent inhibitor of cell proliferation than coumarin and has more marked effects on oncoprotein expression. Also, the A427 cell line was more sensitive to the drugs than Calu-1. ..
- Wang Q, Ni Y, Guo J, Wu J, Qian Y. Comparative study on schizontocidal activity of recrystallized or crude daphnetin against malaria parasites. Biomed Environ Sci. 2004;17:397-401 pubmed..96-56.54 mg/kg while ED50 of recrystallized daphnetin was 11.46 mg/kg, with 95% confidence limit of 8.63-15.22 mg/kg. The results indicate that the efficacy of recrystallized daphnetin is 37.6% higher than that of crude daphnetin. ..
- Duncan S, Leitch E, Stanley K, Richardson A, Laven R, Flint H, et al. Effects of esculin and esculetin on the survival of Escherichia coli O157 in human faecal slurries, continuous-flow simulations of the rumen and colon and in calves. Br J Nutr. 2004;91:749-55 pubmed..Coumarin compounds that occur naturally in dietary plants or when supplemented in the diet probably inhibit the survival of E. coli O157 in the gut. ..
- Durmuş Y, Büyükgüzel E, Terzi B, Tunaz H, Stanley D, Büyükgüzel K. Eicosanoids mediate melanotic nodulation reactions to viral infection in larvae of the parasitic wasp, Pimpla turionellae. J Insect Physiol. 2008;54:17-24 pubmed
- Shahverdi A, Saadat F, Khorramizadeh M, Iranshahi M, Khoshayand M. Two matrix metalloproteinases inhibitors from Ferula persica var. persica. Phytomedicine. 2006;13:712-7 pubmed..persica var. latisecta. Since inhibition of MMP activity has been employed in modality therapy in diseases such as cancer, this compound might be promising in the preparation of anti-MMP therapeutic derivatives. ..
- den Braver Sewradj S, den Braver M, Vermeulen N, Commandeur J, Richert L, Vos J. Inter-donor variability of phase I/phase II metabolism of three reference drugs in cryopreserved primary human hepatocytes in suspension and monolayer. Toxicol In Vitro. 2016;33:71-9 pubmed publisher..As CYP, UGT and SULT metabolism may lead to bioactivation and/or detoxification of drugs, a changed ratio in phase I/phase II metabolism may have important consequences for metabolism-related toxicity. ..
- Zingue S, Michel T, Tchatchou J, Chantal Beatrice Magne N, Winter E, Monchot A, et al. Estrogenic effects of Ficus umbellata Vahl. (Moraceae) extracts and their ability to alleviate some menopausal symptoms induced by ovariectomy in Wistar rats. J Ethnopharmacol. 2016;179:332-44 pubmed publisher..These aforementioned results suggest that F. umbellata extracts as used by the traditional practitioner have estrogen-like effects and may alleviate some menopausal problems such as vaginal dryness and hot flushes. ..
- Gulaka P, Yu J, Liu L, Mason R, Kodibagkar V. Novel S-Gal(®) analogs as (1)H MRI reporters for in vivo detection of ?-galactosidase. Magn Reson Imaging. 2013;31:1006-11 pubmed publisher..Thus, C3-GD successfully detects ?-galactosidase activity in vivo and shows promise as a lacZ gene (1)H MR reporter molecule. ..
- Feng W, Wang Y, Zheng X, Bi Y. [Isolation and structure identification of the chemical constituents from pine needles of Pinus massoniana Lamb]. Yao Xue Xue Bao. 2004;39:190-3 pubmed..Compound I is a new compound, and compounds II, III and IV were isolated from this plant for the first time. ..
- Clarke Pearson M, Brady S. Paerucumarin, a new metabolite produced by the pvc gene cluster from Pseudomonas aeruginosa. J Bacteriol. 2008;190:6927-30 pubmed publisher..Our reinvestigation of the role this gene cluster plays in P. aeruginosa secondary metabolite biosynthesis shows that its major product is actually paerucumarin, a novel isonitrile functionalized cumarin. ..
- Zhao D, Zou L, Lin S, Shi J, Zhu H. 6,7-di-O-glucopyranosyl-esculetin protects SH-SY5Y cells from dopamine-induced cytotoxicity. Eur J Pharmacol. 2008;580:329-38 pubmed publisher..These data indicate that 6,7-di-O-glucopyranosyl-esculetin may provide a useful therapeutic strategy for the treatment of progressive neurodegenerative diseases such as Parkinson's disease. ..
- Yang J, Della Fera M, Baile C. Esculetin induces mitochondria-mediated apoptosis in 3T3-L1 adipocytes. Apoptosis. 2006;11:1371-8 pubmed..These results indicate that esculetin mediated adipocyte apoptosis involves the mitochondrial pathway. Esculetin thus decreases adipocyte number by initiating this apoptotic process in 3T3-L1 adipocytes. ..
- Ramesh B, Pugalendi K. Antihyperlipidemic and antidiabetic effects of umbelliferone in streptozotocin diabetic rats. Yale J Biol Med. 2005;78:189-96 pubmed..Thus, reduction of blood glucose and lipid profiles indicates that UMB has antidiabetic and antihyperlipidemic effects in diabetic rats. ..
- Lavis L, Chao T, Raines R. Latent blue and red fluorophores based on the trimethyl lock. Chembiochem. 2006;7:1151-4 pubmed
- Tunaz H. Eicosanoid biosynthesis inhibitors influence mortality of Pieris brassicae larvae co-injected with fungal conidia. Arch Insect Biochem Physiol. 2006;63:93-100 pubmed..These findings support the idea that virulent effects of entomopathogenic, fungal species can be increased when P. brassicae immune systems are suppressed. ..
- Kurata S, Hirano H, Nagai M. Development of micromarkers with various photoluminescence colors as tracers for shadowing pursuits. Anal Sci. 2008;24:193-200 pubmed..The markers were non-destructively identified using a microscopic FT-IR spectrometer and a microscopic spectrometer equipped with a fluorescence detector. ..
- Barthomeuf C, Lim S, Iranshahi M, Chollet P. Umbelliprenin from Ferula szowitsiana inhibits the growth of human M4Beu metastatic pigmented malignant melanoma cells through cell-cycle arrest in G1 and induction of caspase-dependent apoptosis. Phytomedicine. 2008;15:103-11 pubmed..In vivo investigations are needed to test these hypotheses. ..
- Koebe H, Deglmann C, Metzger R, Hoerrlein S, Schildberg F. In vitro toxicology in hepatocyte bioreactors-extracellular acidification rate (EAR) in a target cell line indicates hepato-activated transformation of substrates. Toxicology. 2000;154:31-44 pubmed..11%+/-4.74 (mean+/-SD) after 7 h. Thus the presented model of hepato-activated toxicity showed an EAR decrease in the ZR 751 cell line that reflected the toxic activation of the predrug by the bioreactor. ..
- Martignoni M, de Kanter R, Moscone A, Grossi P, Monshouwer M. Lack of strain-related differences in drug metabolism and efflux transporter characteristics between CD-1 and athymic nude mice. Cancer Chemother Pharmacol. 2005;55:129-35 pubmed..No significant differences in enzymatic activities and metabolite formation were observed between the two strains. Also mRNA expression profiles of cyp and drug transporter genes were similar between CD-1 and nude mice. ..
- Sebastian S, Sylvestre S, Jayarajan D, Amalanathan M, Oudayakumar K, Gnanapoongothai T, et al. Molecular structure, Normal Coordinate Analysis, harmonic vibrational frequencies, Natural Bond Orbital, TD-DFT calculations and biological activity analysis of antioxidant drug 7-hydroxycoumarin. Spectrochim Acta A Mol Biomol Spectrosc. 2013;101:370-81 pubmed publisher
- Kohno S, Murata T, Sugiura A, Ito C, Iranshahi M, Hikita K, et al. Methyl galbanate, a novel inhibitor of nitric oxide production in mouse macrophage RAW264.7 cells. J Nat Med. 2011;65:353-9 pubmed publisher..Our finding suggests that methyl galbanate may be useful for developing a new drug against neurodegenerative diseases. ..
- Yang X, Xu B, Ran F, Wang R, Wu J, Cui J. [Inhibitory effects of 11 coumarin compounds against growth of human bladder carcinoma cell line E-J in vitro]. Zhong Xi Yi Jie He Xue Bao. 2007;5:56-60 pubmed..These findings indicate that forbesoside, columbianadin, esculin, decursin and umbelliferone would be effective or regarded as potent drug-like or leading compounds against human bladder carcinoma. ..
- Honda Y, Kitaoka M, Hayashi K. Kinetic evidence related to substrate-assisted catalysis of family 18 chitinases. FEBS Lett. 2004;567:307-10 pubmed..These results indicate that the anchimeric assistance of the C2 N-acetamide group at GlcNAc plays a key role in the hydrolytic reactions catalyzed by family 18 chitinases. ..
- Sun Q, Harper T, Dierks E, Zhang L, Chang S, Rodrigues A, et al. 1-Aminobenzotriazole, a known cytochrome P450 inhibitor, is a substrate and inhibitor of N-acetyltransferase. Drug Metab Dispos. 2011;39:1674-9 pubmed publisher..Such an interaction should be considered when using ABT as a nonselective inhibitor of P450, especially when NAT-dependent metabolism is also involved. ..
- Kaneko T, Tahara S, Takabayashi F, Harada N. Suppression of 8-oxo-2'-deoxyguanosine formation and carcinogenesis induced by N-nitrosobis (2-oxopropyl)amine in hamsters by esculetin and esculin. Free Radic Res. 2004;38:839-46 pubmed..These results suggest that the intake of esculin has an inhibitory effect on BOP-induced oxidative DNA damage and carcinogenesis in hamster pancreas. ..
- Macakova K, Rehakova Z, Mladenka P, Karlíčková J, Filipský T, Ríha M, et al. In vitro platelet antiaggregatory properties of 4-methylcoumarins. Biochimie. 2012;94:2681-6 pubmed publisher..5,7-Dihydroxy-4-methylcoumarins appear to be promising candidates for the extension of the current spectrum of antiplatelet drugs. ..
- Mutsaers H, Wilmer M, Reijnders D, Jansen J, van den Broek P, Forkink M, et al. Uremic toxins inhibit renal metabolic capacity through interference with glucuronidation and mitochondrial respiration. Biochim Biophys Acta. 2013;1832:142-50 pubmed publisher..This may have a significant impact on drug and uremic retention solute disposition in CKD patients...
- Ramesh B, Pugalendi K. Influence of umbelliferone on membrane-bound ATPases in streptozotocin-induced diabetic rats. Pharmacol Rep. 2007;59:339-48 pubmed..Thus, our results show that the normalization of membrane-bound ATPases in various tissues, is due to improved glycemic control and antioxidant activity by UMB. ..
- Ding X, Feng X, Dong Y, Zhao X, Chen Y, Wang M. [Studies on chemical constituents of the roots of Angelica pubescens]. Zhong Yao Cai. 2008;31:516-8 pubmed..O-beta-D- glucopyranosyl -(R)-by-akangelicin (VI) and sec. -O-beta-D- glucopyranosyl-(R) -byakangelicin (VII). Compound IV, VI and VII are isolated from Angelica pubescens for the first time. ..
- Xiang T, Xiong Q, Ketut A, Tezuka Y, Nagaoka T, Wu L, et al. Studies on the hepatocyte protective activity and the structure-activity relationships of quinic acid and caffeic acid derivatives from the flower buds of Lonicera bournei. Planta Med. 2001;67:322-5 pubmed
- Mazzei M, Nieddu E, Miele M, Balbi A, Ferrone M, Fermeglia M, et al. Activity of Mannich bases of 7-hydroxycoumarin against Flaviviridae. Bioorg Med Chem. 2008;16:2591-605 pubmed..The good correlation between calculated molecular modeling IC(50) and experimental EC(50) indicates that DNA polymerase is potentially involved in the inhibition of surrogate HCV viruses...
- Pan S, Huang Y, Guh J, Chang Y, Peng C, Teng C. Esculetin inhibits Ras-mediated cell proliferation and attenuates vascular restenosis following angioplasty in rats. Biochem Pharmacol. 2003;65:1897-905 pubmed..It also inhibits intimal hyperplasia after balloon vascular injury in the rat, indicating the therapeutic potential for treating restenosis after arterial injury. ..