Bu məqalənin sonunda mənbə siyahısı var, lakin mətndaxili mənbələr heç və ya kifayət qədər istifadə edilmədiyi üçün bəzi məlumatların mənbəsi bilinmir. |
Kumarin (2H-chromene-2one ya 2H-1-benzopyranon-2) — lactone o-hydroxycinnamic turşusu.
Kumarin | |
---|---|
Ümumi | |
Kimyəvi formulu | C₉H₆O₂ |
Molyar kütlə | 146,14 q/mol |
Fiziki xassələri | |
Sıxlıq | 0,935 q/sm³ |
Termik xüsusiyyətlər | |
Ərimə nöqtəsi | 71 °S |
Qaynama nöqtəsi | 301 °S |
Təsnifatı | |
CAS-da qeyd. nöm. | 91-64-5 |
PubChem | 323 |
SMILES | C1=CC=C2C(=C1)C=CC(=O)O2 |
RTECS | GN4200000 |
ChEBI | 28794 |
ChemSpider | 13848793 |
Xüsusiyyətləri
Yeni kəsilmiş otların qoxusunu verən rəngsiz kristallardır; ərimə temperaturu 70 ° C, qaynama temperaturu 291 ° C-dir. Kumarin spirt və efirdə yaxşı, suda zəif həll olur ,4-hidroksillə yüngül turşu xassəsi göstərdiyi üçün, bir qədər qələvi mühitdə həll edilə bilər.
Kimyəvi xassələr
Kumarin benzoldan fərqli olaraq doymamış laktonlar və ya benzoləvəzləyicilərlə daha az reaksiya qabiliyyətinə malikdir. A
Təbiətdə olması
Kumarin glikosidlər şəklində bir çox bitkilərin tərkibində aşkar edilmişdir - onların nümayəndələri arasında Astrov ailə ( gerbera, chamomile, civanperçemi ), eləcə də yonca, bizon, darçını göstərmək olar.
Alınması
Sənayedə coumarin salisilik aldehid və asatik anhidritdən əldə edilir (bax) Perkin reaksiya ).
Tətbiqi
Kumarindən tütün məhsullarının istehsalında və ətir sənayesində istifadə olunur. Törəmələridən (coumarins) boya lazerlərində istifadə olunur. Qalvanika sənayesində də güclü parlayıcı kimi istifadə olunur. Kumarinin bir insana fizioloji təsiri çox zəifdir. Bununla birlikdə, coumarin müxtəlif bitkilər üzərində nəzərə çarpacaq dərəcədə təsir göstərir. Koumarin törəmələrində fizioloji təsiri daha qabarıqdır. Məsələn, coumarin-3-karboksilik turşusu törəmələri hipnotikdir. Dikumarol (3,3'-metilen-bis-4-hidroksikumarin) qan laxtalanmasına müdaxilə edir.
Mənbə
- Химическая энциклопедия / Редкол.: Кнунянц И.Л. и др.. — М.: Советская энциклопедия, 1990. — Т. 2 (Даф-Мед). — 671 с. — .
- Lake B.G. Coumarin metabolism toxicity and carcinogenicity: relevance for human risk assessment / B.G. Lake // Food and Chemical Toxicology. –1999. –№ 37. –Р. 423–453.
- Carlton B. D. Effects of Coumarin Following Perinatal and Chronic Exposure in SpragueWDawley Rats and CDW1 Mice / B. D. Carlton, J.–C. Auburn, G. S. Simon //Fundamental and Applied Toxicology. W1996. – № 30. –P. 145–151.
- Opdyke D. L. J. Monographs on fragrance raw materials: coumarin/ D. L. J. Opdyke// Food and cosmetics Toxicology . –1974. –№ 12. –P. 385–388.
- Качественное обнаружение кумаринов в растительном сырье / Г.А. Дрозд, Н.Ф. Комиссаренко // IV Всесоюзный симпоз. по фенольным соединениям. –Ташкент. –1982. –С. 27–28.
- The pharmacology, metabolism, analysis and applications of coumarin and coumarinWrelated compounds / D. Egan, R. O'Kennedy, E. Moran [et al.] // Drug. Metab. Rev. 1990. –№ 22. –P. 503–529.
- Phase II study of coumarin and cimetidine in patients with metastatic renal cell сarcinoma / F. H. Dexeus, С. J. Logothetis, F. Sella, A. [et al.] // J. Clin. Oncol. 1990. –№ 8. –P. 325–329.
- Cox D. The relevancy of liver toxicity in patients treated with coumarin (1,2WbenzoWpyron) / D.Cox, R. O'Kennedy, R. D. Thornes // Hum. Toxicol..–1989. –№
- –P. 501–506. 8. Morris L. SideWeffects of coumarin / L .Morris, P.D.Welsby // Postgrad. Med. J. –1995. –№ 71. – P. 701–702.
- Toxicity of coumarin / L. W. Hazleton, T. W. Tusing, , Zeitlin M.K. [et al.] // J. Pharmacol. Exp. Ther. –1956. –№ 118. –P. 348–358.
- Cohen A.J. Critical review of the toxicology of coumarin with special references to interspecies differW ences in metabolism and hepatotoxic response and their significance to man / A. J. Cohen // Food Chem. Toxicol. –1979. –№ 17. –P. 277–289.
- Lake B. G. Investigations into the mechanism of coumarinWinduced hepatotoxicity in the rat / B. G. Lake // Arch. Toxicol. Suppl. –1984. –№ 7. –P. 16–29.
- Lake B. G. Effect of pretreatment with some mixedWfunction oxidase enzyme inducers on the acute hepatotoxicity of coumarin in the rat / B. G. Lake, J. G. Evans, // Food Chem. Toxicol. –1993. –№ 31. – P. 963–970.
- Comparative metabolism and kinetics of coumarin in mice and rats / S. L. Born, A. M. Api, R. A. Ford, [et al.] // Food Chem. Toxicol. –2003. –№41. –P. 247–258.
- BeckleyWKartey S. A. J. Comparative in vitro skin absorption and metabolism of coumarin (1,2WbenzopyW rone) in human, rat and mouse / S. A. J. BeckleyWKartey, S. A. M. Hotchkins, M. Capel // Toxicology and Applied Pharmacology . –1997. –№ 145. –P. 34–42.
- Metabolism and toxicity of coumarin on cultured human, rat, mouse and rabbit hepatocytes / D.Ratanasavanh, D. Lamiable, M. Biour [et al.] // Fundam. Clin. Pharmacol. –1996. –V.10(6). – P. 504–510.
- Born S. L. OWhydroxyphenylacetaldehyde (oWHPA) is a hepatotoxic metabolite of coumarin / S. L. Born, J. K. Hu, L. D. LehmanWMcKeeman // Toxicological Sciences. –1998. –V. 42. –№ 1–S. –P. 400–403.
- MechanismWbased inactivation of human liver cytochrome P450 2A6 by 8Wmethoxypsoralen / L. L. Koenigs, R. M. Peter, S. J. Thompson [et al.] // Drug Metabolism and Disposition . –1997. –№ 25. – P. 1407–1415.
- Fentem J. H. Species differences in the metabolism and hepatotoxicity of coumarin / J. H. Fentem, J. R. Fry // Comp. Biochem. Physiol. –1993. –№ 104. –P. 1–8.
- Fentem J. H. Species differences in the hepatotoxicity of coumarin: A comparison of rat and Mongolian gerbil / J. H.Fentem, J. R. Fry, N. W. Thomas // Toxicology. –1992. –№ 71. –P. 129–136.
- iquid chromatographic determination оf the glutathione conjugate and ring opened metabolites formed from coumarin epoxidation. / Vassallo, J. D., Morall, S. W., Fliter, [et al.] // J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. –2003. –№ 794. –P. 257–271.
- Gangolli S. D. Studies on the metabolism and hepatotoxicity of coumarin in the baboon / S. D.Gangolli, W. H . Shilling, P.Grasso , L. F. Gaunt //Biochem. Soc Trans. –1974. –№ 2. –P. 310–312.
- 22. Evans J. G. TwoWyear toxicity study on coumarin in the baboon / J. G. Evans, I. F. Gaunt, B. G. Lake // Food Cosmet. Toxicol. –1979. –№ 17. –P. 187–193.
- 23. Ueno I. NonWcarcinogenic response to coumarin in Syrian golden hamsters / I.Ueno, I. Hirono // Food Cosmet. Toxicol. –1980. –№ 19. –P. 353–355.
- 24. Wood A. W. Genetic variation in coumarin hydroxylase activity in the mouse (mus musculus) / A. W. Wood, A. H. Conney // Science. –1974. –№ 185 (4151). –P. 612–614.
- 25. Endell W. Coumarin toxicity in different strains of mice. / W. Endell, Seidel G. // Agents Actions. –1978. –№8. –P. 299–302.
- 26. Metabolism of coumarin and 7Wethoxycoumarin by rat, mouse, guinea pig, Cynomolgus monkey and human precisionWcut liver slices / A. Steensma, J. A. Beamand, D. G. Walters [et al.] // Xenobiotica . –1994. –№ 24. –P. 893W907.
- 27. Pelkonen O. CYP2A6: a human coumarin 7Whydroxylase / Pelkonen O., Rautio A., Raunio H., Pasanen M. // Toxicology . –2000. –V. 144. –Issues 1–3. –P. 139–147.
- 28. A single amino acid substitution (Leu160His) in cytochrome P450 CYP2A6 causes switching from 7W hydroxylation to 3Whydroxylation of coumarin / H.Hadidi, K.Zahlsen, J. R. Idle [et al.] // Food and Chemical Toxicology . –1997. –№ 35. –P. 903–907.
- 29. Studies on the mechanism of coumarinWindiced toxicity in rat hepatocytes: Comparison with dihydroW coumarin and other coumarin metabolites / B. G. Lake, T. J. Gray, J. G.Evans [et al.] // Toxicol. Appl. Pharmacol. –1989. –№ 97. –P. 311–323.
- 30. Studies on the induction of cholangiofibrosis by coumarine on the rat / J. G. Evans, E. C. Appleby, B. G. Lake [et al.] // Toxicology. –1989. –№ 55. – P. 207–224.
- 31. Effect of inducers of cytochrome P450 on the metabolism of [3WHC] coumarin by rat hepatic microsomes / M. M. Peters, D. G.Walters, B. van Ommen [et al.] // Xenobiotica. –1991. –№ 21. –P. 499–514.
- 32. Identification of the human liver cytochrome PW450 responsible for coumarin 7Whydroxylase activity/ J. S. Miles, A. W. McLaren , L. M. Forrester [et al.] // Biochem. J. –1990. –№ 267. –P. 365–371.
- 33. Williams R. T. The influence of enterohepatic circulation on toxicity of drugs/ R. T. Williams, P. Millburn, R. L. Smith //Ann. N. Y. Acad. Sci. –1965. –123. –P. 110–113.
- 34. Shilling W. H. Metabolism of coumarin in man / W. H. Shilling, R. F. Crampton, R. C. Longland // Nature. –1969. –№ 221. –P. 664–665.
- 35. Feuer G. Liver response tests. VII Coumarin metabolism in relation to the inhibition of ratWliver glucose 6W phosphatase / G. Feuer, Golberg L., Gibson K. //Food. Cosmet. Toxicol. –1966. –№ 4. –P. 157–167.
- 36. Berenbaum M. Coumarins and caterpillars: a case for coevolution. / M.Berenbaum // Evolution. –1983. –№ 37(1). –P. 163–179.
- 37. Guilbault G.G Practical fluorescence / edited by George G. Guilbault . –New York. USA. –1990. –249 p.
- 38. Marshall M. E. Growth–inhibitory effects of coumarin (1,2Wbenzopyrone) and 7Whydroxycoumarin on human malignant cell lines in vitro /M. E. Marshall , K. Kervin, C. Benefield // J. Cancer Res. Clin. Oncol . –1994, V. 120. –suppl.1. –P. 3–10.
- 39. Seliger B. 7WHydroxycoumarin inhibits oncogeneWinduced transformation of murine fibroblasts / B. Seliger, H. Pettersson // J. Cancer Res. Clin. Oncol . –1994. –№ 20 (Suppl). –P. 23–27.
- 40. Antitumor and immunomodulatory affect of coumarin and 7Whydroxycoumarin against Sarcoma 180 in mice / T.N. Stefanova, N.J. Nikolova, R.A. Toshkova [et al.] // Journal of experimental therapeutics & oncology. –2007. –№ 6(2). –P. 107–115.
- 41. Hoult J. Pharmacological and biochemical actions of simple coumarins:natural products with therapeutic potential / J. Hoult, M. Paya // Gen. Pharmacol. –1996. –№ 7. –P. 713–722.
- 42. Kostova I. Synthetic and natural coumarins as cytotoxic agents / I. Kostova // Curr. Med. Chem. –AntiW Cancer Agents. –2005. –V. 5. –№. 1. –P. 29–46
- 43. Umbelliferone analogs and their potential to inhibit benzo(a)pyreneW and hydrogen peroxideWinduced mutations / S.P. Pillai, S.R.Menon, L.A.Mitscher [et al.] // J. Nat. Prod. –1999. –V. 62. –P. 1358–1362.
- 44. Evaluation of antigenotoxicity effects of umbelliprenin on human peripheral lymphocytes exposed to oxidative stress / F. Soltani, F. Mosaffa, M. Iranshahi [et al.] //Cell. Biol. Toxicol. –2009. –№ 25(3). –P. 291–296.
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- 46. Effects of umbelliferone in a murine model of allergic airway inflammation / J. F. Vasconcelos, M. M. Teixeira, J. M. BarbosaWFilho [et al.] // European Journal of Pharmacology. –2009. –V. 609. –Issues 1–3. – P. 126–131
- 47. Effect of umbelliferone (7Whydroxycoumarin, 7WHOC) on the enzymatic, edematogenic and necrotic activW ities of secretory phospholipase A2 (sPLA2) isolated from Crotalus durissus collilineatus venom / D.O. Toyamaa, S. Marangonib, E.B.S. DizWFilhob [et al.] // Toxicon. –2009. –V. 53. –Issue 4. –P. 417–426. 44 Проблеми харчування 34/2009
- 48. Hardt T.J. Investigation of the dose response relationship upon intraperitoneal administration of coumarin and 7Whydroxycoumarin on the carrageenan induced edema of the rats hind paw / T.J. Hardt , W.A. Ritschell // Arzneim. Forsch. –1983. –V. 33. –issue 12. –P. 1662–1666.
- 49. Янченко П.С. Виділення та вивчення деяких кумаринів і хромонів із рослин родин бобові та селеW рові та їх ліпазотропна активність / П.С. Янченко, А.М. Ковальова, Г.В. Георгієвський, А.М. КомісаW ренко // ФАРМАКОМ. –2004. –№ 2. –C. 1–7.
- 50. Ramesh B. Protective effect of umbelliferone on membranous fatty acid composition in streptozotocinW induced diabetic rats / B.Ramesh, P. Viswanathan P., K.V.Pugalendi // European Journal of Pharmacology. –2007. –V. 566. –Issues 1–3. –P. 231–239.
- 51. Ramesh B. Impact of umbelliferone (7–hydroxycoumarin) on hepatic marker enzymes in streptozotocin diabetic rats /B. Ramesh , K.V. Pugalendi // Indian J. Pharmacol. –2006. –№ 38. –P. 209–210.
- 52. Ramesh B. Antihyperglycemic effect of umbelliferone in STZWdiabetic rats. / B. Ramesh, K.V. Pugalendi // J. Med. Food . –2006. –№ 9 (4). –P. 562–566.
- 53. Ramesh B. Influence of umbelliferone on membrane–bound ATPases in streptozotocinWinduced diabetic rats / B. Ramesh , K.V. Pugalendi // Pharmacol. Rep. –2004. –№ 59 (3). –P. 339–348.
- 54. Ramesh B. Antihyperlipidemic and antidiabetic effects of umbelliferone in streptozotocin diabetic rats / B. Ramesh , K.V. Pugalendi // Yale J. Biol. Med. –2005. –№ 78(4). –P. 189–196.
- 55. Ramesh B. Impact of umbelliferone on erythrocyte redox status in STZWdiabetic rats / B. Ramesh, K.V. Pugalendi // Yale Journal of Biology and Medicine. –2005. –№ 78. –P. 11–18.
- 56. Ramesh B. Effect of umbelliferone on tail tendon collagen and haemostatic function in streptozotocinW diabetic rats / B. Ramesh , K.V. Pugalendi // Basic Clin. Pharmacol. Toxicol. –2007. –V. 101. –№ 2. – P. 73–77.
İstinadlar
- coumarin (ing.).
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Bu meqalenin sonunda menbe siyahisi var lakin metndaxili menbeler hec ve ya kifayet qeder istifade edilmediyi ucun bezi melumatlarin menbesi bilinmir Lutfen menbeleri uygun sekilde metnin daxilinde yerlesdirerek meqalenin tekmillesdirilmesine komek edin Kumarin 2H chromene 2one ya 2H 1 benzopyranon 2 lactone o hydroxycinnamic tursusu KumarinUmumiKimyevi formulu C H O Molyar kutle 146 14 q molFiziki xasseleriSixliq 0 935 q sm Termik xususiyyetlerErime noqtesi 71 SQaynama noqtesi 301 STesnifatiCAS da qeyd nom 91 64 5PubChem 323SMILES C1 CC C2C C1 C CC O O2RTECS GN4200000ChEBI 28794ChemSpider 13848793XususiyyetleriYeni kesilmis otlarin qoxusunu veren rengsiz kristallardir erime temperaturu 70 C qaynama temperaturu 291 C dir Kumarin spirt ve efirde yaxsi suda zeif hell olur 4 hidroksille yungul tursu xassesi gosterdiyi ucun bir qeder qelevi muhitde hell edile biler Kimyevi xasselerKumarin benzoldan ferqli olaraq doymamis laktonlar ve ya benzolevezleyicilerle daha az reaksiya qabiliyyetine malikdir ATebietde olmasiKumarin glikosidler seklinde bir cox bitkilerin terkibinde askar edilmisdir onlarin numayendeleri arasinda Astrov aile gerbera chamomile civanpercemi elece de yonca bizon darcini gostermek olar AlinmasiSenayede coumarin salisilik aldehid ve asatik anhidritden elde edilir bax Perkin reaksiya TetbiqiKumarinden tutun mehsullarinin istehsalinda ve etir senayesinde istifade olunur Toremeleriden coumarins boya lazerlerinde istifade olunur Qalvanika senayesinde de guclu parlayici kimi istifade olunur Kumarinin bir insana fizioloji tesiri cox zeifdir Bununla birlikde coumarin muxtelif bitkiler uzerinde nezere carpacaq derecede tesir gosterir Koumarin toremelerinde fizioloji tesiri daha qabariqdir Meselen coumarin 3 karboksilik tursusu toremeleri hipnotikdir Dikumarol 3 3 metilen bis 4 hidroksikumarin qan laxtalanmasina mudaxile edir MenbeHimicheskaya enciklopediya Redkol Knunyanc I L i dr M Sovetskaya enciklopediya 1990 T 2 Daf Med 671 s ISBN 5 82270 035 5 Lake B G Coumarin metabolism toxicity and carcinogenicity relevance for human risk assessment B G Lake Food and Chemical Toxicology 1999 37 R 423 453 Carlton B D Effects of Coumarin Following Perinatal and Chronic Exposure in SpragueWDawley Rats and CDW1 Mice B D Carlton J C Auburn G S Simon Fundamental and Applied Toxicology W1996 30 P 145 151 Opdyke D L J Monographs on fragrance raw materials coumarin D L J Opdyke Food and cosmetics Toxicology 1974 12 P 385 388 Kachestvennoe obnaruzhenie kumarinov v rastitelnom syre G A Drozd N F Komissarenko IV Vsesoyuznyj simpoz po fenolnym soedineniyam Tashkent 1982 S 27 28 The pharmacology metabolism analysis and applications of coumarin and coumarinWrelated compounds D Egan R O Kennedy E Moran et al Drug Metab Rev 1990 22 P 503 529 Phase II study of coumarin and cimetidine in patients with metastatic renal cell sarcinoma F H Dexeus S J Logothetis F Sella A et al J Clin Oncol 1990 8 P 325 329 Cox D The relevancy of liver toxicity in patients treated with coumarin 1 2WbenzoWpyron D Cox R O Kennedy R D Thornes Hum Toxicol 1989 P 501 506 8 Morris L SideWeffects of coumarin L Morris P D Welsby Postgrad Med J 1995 71 P 701 702 Toxicity of coumarin L W Hazleton T W Tusing Zeitlin M K et al J Pharmacol Exp Ther 1956 118 P 348 358 Cohen A J Critical review of the toxicology of coumarin with special references to interspecies differW ences in metabolism and hepatotoxic response and their significance to man A J Cohen Food Chem Toxicol 1979 17 P 277 289 Lake B G Investigations into the mechanism of coumarinWinduced hepatotoxicity in the rat B G Lake Arch Toxicol Suppl 1984 7 P 16 29 Lake B G Effect of pretreatment with some mixedWfunction oxidase enzyme inducers on the acute hepatotoxicity of coumarin in the rat B G Lake J G Evans Food Chem Toxicol 1993 31 P 963 970 Comparative metabolism and kinetics of coumarin in mice and rats S L Born A M Api R A Ford et al Food Chem Toxicol 2003 41 P 247 258 BeckleyWKartey S A J Comparative in vitro skin absorption and metabolism of coumarin 1 2WbenzopyW rone in human rat and mouse S A J BeckleyWKartey S A M Hotchkins M Capel Toxicology and Applied Pharmacology 1997 145 P 34 42 Metabolism and toxicity of coumarin on cultured human rat mouse and rabbit hepatocytes D Ratanasavanh D Lamiable M Biour et al Fundam Clin Pharmacol 1996 V 10 6 P 504 510 Born S L OWhydroxyphenylacetaldehyde oWHPA is a hepatotoxic metabolite of coumarin S L Born J K Hu L D LehmanWMcKeeman Toxicological Sciences 1998 V 42 1 S P 400 403 MechanismWbased inactivation of human liver cytochrome P450 2A6 by 8Wmethoxypsoralen L L Koenigs R M Peter S J Thompson et al Drug Metabolism and Disposition 1997 25 P 1407 1415 Fentem J H Species differences in the metabolism and hepatotoxicity of coumarin J H Fentem J R Fry Comp Biochem Physiol 1993 104 P 1 8 Fentem J H Species differences in the hepatotoxicity of coumarin A comparison of rat and Mongolian gerbil J H Fentem J R Fry N W Thomas Toxicology 1992 71 P 129 136 iquid chromatographic determination of the glutathione conjugate and ring opened metabolites formed from coumarin epoxidation Vassallo J D Morall S W Fliter et al J Chromatogr B Analyt Technol Biomed Life Sci 2003 794 P 257 271 Gangolli S D Studies on the metabolism and hepatotoxicity of coumarin in the baboon S D Gangolli W H Shilling P Grasso L F Gaunt Biochem Soc Trans 1974 2 P 310 312 22 Evans J G TwoWyear toxicity study on coumarin in the baboon J G Evans I F Gaunt B G Lake Food Cosmet Toxicol 1979 17 P 187 193 23 Ueno I NonWcarcinogenic response to coumarin in Syrian golden hamsters I Ueno I Hirono Food Cosmet Toxicol 1980 19 P 353 355 24 Wood A W Genetic variation in coumarin hydroxylase activity in the mouse mus musculus A W Wood A H Conney Science 1974 185 4151 P 612 614 25 Endell W Coumarin toxicity in different strains of mice W Endell Seidel G Agents Actions 1978 8 P 299 302 26 Metabolism of coumarin and 7Wethoxycoumarin by rat mouse guinea pig Cynomolgus monkey and human precisionWcut liver slices A Steensma J A Beamand D G Walters et al Xenobiotica 1994 24 P 893W907 27 Pelkonen O CYP2A6 a human coumarin 7Whydroxylase Pelkonen O Rautio A Raunio H Pasanen M Toxicology 2000 V 144 Issues 1 3 P 139 147 28 A single amino acid substitution Leu160His in cytochrome P450 CYP2A6 causes switching from 7W hydroxylation to 3Whydroxylation of coumarin H Hadidi K Zahlsen J R Idle et al Food and Chemical Toxicology 1997 35 P 903 907 29 Studies on the mechanism of coumarinWindiced toxicity in rat hepatocytes Comparison with dihydroW coumarin and other coumarin metabolites B G Lake T J Gray J G Evans et al Toxicol Appl Pharmacol 1989 97 P 311 323 30 Studies on the induction of cholangiofibrosis by coumarine on the rat J G Evans E C Appleby B G Lake et al Toxicology 1989 55 P 207 224 31 Effect of inducers of cytochrome P450 on the metabolism of 3WHC coumarin by rat hepatic microsomes M M Peters D G Walters B van Ommen et al Xenobiotica 1991 21 P 499 514 32 Identification of the human liver cytochrome PW450 responsible for coumarin 7Whydroxylase activity J S Miles A W McLaren L M Forrester et al Biochem J 1990 267 P 365 371 33 Williams R T The influence of enterohepatic circulation on toxicity of drugs R T Williams P Millburn R L Smith Ann N Y Acad Sci 1965 123 P 110 113 34 Shilling W H Metabolism of coumarin in man W H Shilling R F Crampton R C Longland Nature 1969 221 P 664 665 35 Feuer G Liver response tests VII Coumarin metabolism in relation to the inhibition of ratWliver glucose 6W phosphatase G Feuer Golberg L Gibson K Food Cosmet Toxicol 1966 4 P 157 167 36 Berenbaum M Coumarins and caterpillars a case for coevolution M Berenbaum Evolution 1983 37 1 P 163 179 37 Guilbault G G Practical fluorescence edited by George G Guilbault New York USA 1990 249 p 38 Marshall M E Growth inhibitory effects of coumarin 1 2Wbenzopyrone and 7Whydroxycoumarin on human malignant cell lines in vitro M E Marshall K Kervin C Benefield J Cancer Res Clin Oncol 1994 V 120 suppl 1 P 3 10 39 Seliger B 7WHydroxycoumarin inhibits oncogeneWinduced transformation of murine fibroblasts B Seliger H Pettersson J Cancer Res Clin Oncol 1994 20 Suppl P 23 27 40 Antitumor and immunomodulatory affect of coumarin and 7Whydroxycoumarin against Sarcoma 180 in mice T N Stefanova N J Nikolova R A Toshkova et al Journal of experimental therapeutics amp oncology 2007 6 2 P 107 115 41 Hoult J Pharmacological and biochemical actions of simple coumarins natural products with therapeutic potential J Hoult M Paya Gen Pharmacol 1996 7 P 713 722 42 Kostova I Synthetic and natural coumarins as cytotoxic agents I Kostova Curr Med Chem AntiW Cancer Agents 2005 V 5 1 P 29 46 43 Umbelliferone analogs and their potential to inhibit benzo a pyreneW and hydrogen peroxideWinduced mutations S P Pillai S R Menon L A Mitscher et al J Nat Prod 1999 V 62 P 1358 1362 44 Evaluation of antigenotoxicity effects of umbelliprenin on human peripheral lymphocytes exposed to oxidative stress F 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