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BioMed Research International
Volume 2013 (2013), Article ID 963248, 14 pages
http://dx.doi.org/10.1155/2013/963248
Review Article

Review on Natural Coumarin Lead Compounds for Their Pharmacological Activity

1Department of Biotechnology and Food Technology, Durban University of Technology, Durban 4001, South Africa
2Department of Public Health Medicine, University of KwaZulu-Natal, Howard College Campus, Durban 4001, South Africa

Received 7 October 2012; Accepted 4 February 2013

Academic Editor: Paul W. Doetsch

Copyright © 2013 K. N. Venugopala et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. Y. Aoyama, T. Katayama, M. Yamamoto, H. Tanaka, and K. Kon, “A new antitumor antibiotic product, demethylchartreusin. Isolation and biological activities,” The Journal of Antibiotics, vol. 45, no. 6, pp. 875–878, 1992. View at Google Scholar · View at Scopus
  2. M. Iranshahi, M. Askari, A. Sahebkar, and D. Hadjipavlou-Litina, “Evaluation of antioxidant, anti-inflammatory and lipoxygenase inhibitory activities of the prenylated coumarin umbelliprenin,” DARU, vol. 17, no. 2, pp. 99–103, 2009. View at Google Scholar · View at Scopus
  3. W. C. Evans, Trease and Evans Pharmacognosy, Elsevier Ltd., 16th edition, 2009.
  4. J. A. Mead, J. N. Smith, and R. T. Williams, “Studies in detoxication. 72. The metabolism of coumarin and of o-coumaric acid,” The Biochemical Journal, vol. 68, no. 1, pp. 67–74, 1958. View at Google Scholar · View at Scopus
  5. C. Spino, M. Dodier, and S. Sotheeswaran, “Anti-HIV coumarins from calophyllum seed oil,” Bioorganic and Medicinal Chemistry Letters, vol. 8, no. 24, pp. 3475–3478, 1998. View at Publisher · View at Google Scholar · View at Scopus
  6. S. Rosselli, A. M. Maggio, N. Faraone et al., “The cytotoxic properties of natural coumarins isolated from roots of Ferulago campestris (Apiaceae) and of synthetic ester derivatives of aegelinol,” Natural Product Communications, vol. 4, no. 12, pp. 1701–1706, 2009. View at Google Scholar · View at Scopus
  7. Atta-ur-Rahman, M. Shabbir, S. Ziauddin Sultani, A. Jabbar, and M. I. Choudhary, “Cinnamates and coumarins from the leaves of Murraya paniculata,” Phytochemistry, vol. 44, no. 4, pp. 683–685, 1997. View at Publisher · View at Google Scholar · View at Scopus
  8. A. J. Cohen, “Critical review of the toxicology of coumarin with special reference to interspecies differences in metabolism and hepatotoxic response and their significance to man,” Food and Cosmetics Toxicology, vol. 17, no. 3, pp. 277–289, 1979. View at Google Scholar · View at Scopus
  9. R. W. Fuller, H. R. Bokesch, K. R. Gustafson et al., “HIV-Inhibitory coumarins from latex of the tropical rainforest tree Calophyllum teysmannii var. inophylloide,” Bioorganic and Medicinal Chemistry Letters, vol. 4, no. 16, pp. 1961–1964, 1994. View at Publisher · View at Google Scholar · View at Scopus
  10. J. Choi, K. T. Lee, H. Ka, W. T. Jung, H. J. Jung, and H. J. Park, “Constituents of the essential oil of the Cinnamomum cassia stem bark and the biological properties,” Archives of Pharmacal Research, vol. 24, no. 5, pp. 418–423, 2001. View at Google Scholar · View at Scopus
  11. F. Bourgaud, A. Hehn, R. Larbat et al., “Biosynthesis of coumarins in plants: a major pathway still to be unravelled for cytochrome P450 enzymes,” Phytochemistry Reviews, vol. 5, no. 2-3, pp. 293–308, 2006. View at Publisher · View at Google Scholar · View at Scopus
  12. D. Bogdal, “Coumarins: fast synthesis by Knoevenagel condensation under microwave irradiation,” Journal of Chemical Research, Synopses, no. 8, pp. 468–469, 1998. View at Google Scholar · View at Scopus
  13. B. G. Lake, “Coumarin metabolism, toxicity and carcinogenicity: relevance for human risk assessment,” Food and Chemical Toxicology, vol. 37, no. 4, pp. 423–453, 1999. View at Publisher · View at Google Scholar · View at Scopus
  14. D. Egan, R. O'Kennedy, E. Moran, D. Cox, E. Prosser, and R. D. Thornes, “The pharmacology, metabolism, analysis, and applications of coumarin and coumarin-related compounds,” Drug Metabolism Reviews, vol. 22, no. 5, pp. 503–529, 1990. View at Google Scholar · View at Scopus
  15. M. E. Marshall, J. L. Mohler, K. Edmonds et al., “An updated review of the clinical development of coumarin (1,2-benzopyrone) and 7-hydroxycoumarin,” Journal of Cancer Research and Clinical Oncology, vol. 120, supplement, pp. S39–S42, 1994. View at Google Scholar · View at Scopus
  16. R. D. H. Murray, “Naturally occuring plant coumarins,” in Progress in the Chemistry of Organic Natural Products, pp. 2–105, Springer, New York, NY, USA, 1997. View at Google Scholar
  17. N. B. Piller, “A comparison of the effectiveness of some anti inflammatory drugs on thermal oedema,” British Journal of Experimental Pathology, vol. 56, no. 6, pp. 554–560, 1975. View at Google Scholar · View at Scopus
  18. A. Witaicenis, L. N. Seito, and L. C. Di Stasi, “Intestinal anti-inflammatory activity of esculetin and 4-methylesculetin in the trinitrobenzenesulphonic acid model of rat colitis,” Chemico-Biological Interactions, vol. 186, no. 2, pp. 211–218, 2010. View at Publisher · View at Google Scholar · View at Scopus
  19. K. Hodák, V. Jakesová, and V. Dadák, “On the antibiotic effects of natural coumarins. VI. The relation of structure to the antibacterial effects of some natural coumarins and the neutralization of such effects,” Cesko-Slovenska Farmacie, vol. 16, no. 2, pp. 86–91, 1967. View at Google Scholar
  20. C. M. Wang, W. Zhou, C. X. Li, H. Chen, Z. Q. Shi, and Y. J. Fan, “Efficacy of osthol, a potent coumarin compound, in controlling powdery mildew caused by Sphaerotheca fuliginea,” Journal of Asian Natural Products Research, vol. 11, no. 9, pp. 783–791, 2009. View at Publisher · View at Google Scholar · View at Scopus
  21. E. B. Chain, “Chemistry and biochemistry of antibiotics,” Annual Review of Biochemistry, vol. 27, no. 3, pp. 167–222, 1958. View at Google Scholar · View at Scopus
  22. M. Gellert, M. H. O'Dea, T. Itoh, and J. I. Tomizawa, “Novobiocin and coumermycin inhibit DNA supercoiling catalyzed by DNA gyrase,” Proceedings of the National Academy of Sciences of the United States of America, vol. 73, no. 12, pp. 4474–4478, 1976. View at Google Scholar · View at Scopus
  23. J. Portugal, “Chartreusin, elsamicin A and related anti-cancer antibiotics,” Current Medicinal Chemistry. Anti-Cancer Agents, vol. 3, no. 6, pp. 411–420, 2003. View at Publisher · View at Google Scholar · View at Scopus
  24. W. K. Whang, H. S. Park, I. Ham et al., “Natural compounds, fraxin and chemicals structurally related to fraxin protect cells from oxidative stress,” Experimental and Molecular Medicine, vol. 37, no. 5, pp. 436–446, 2005. View at Google Scholar · View at Scopus
  25. C. C. Chiang, M. J. Cheng, C. F. Peng, H. Y. Huang, and I. S. Chen, “A novel dimeric coumarin analog and antimycobacterial constituents from Fatoua pilosa,” Chemistry and Biodiversity, vol. 7, no. 7, pp. 1728–1736, 2010. View at Publisher · View at Google Scholar · View at Scopus
  26. M. I. Yusupov and G. P. Sidyakin, “Fraxidin and isofraxidin from Artemisia scotina,” Chemistry of Natural Compounds, vol. 11, no. 1, p. 94, 1975. View at Publisher · View at Google Scholar · View at Scopus
  27. E. Shin, K. M. Choi, H. S. Yoo, C. K. Lee, B. Y. Hwang, and M. K. Lee, “Inhibitory effects of coumarins from the stem barks of Fraxinus rhynchophylla on adipocyte differentiation in 3T3-L1 cells,” Biological and Pharmaceutical Bulletin, vol. 33, no. 9, pp. 1610–1614, 2010. View at Publisher · View at Google Scholar · View at Scopus
  28. B. R. Barik, A. K. Dey, and A. Chatterjee, “Murrayatin, a coumarin from Murraya exotica,” Phytochemistry, vol. 22, no. 10, pp. 2273–2275, 1983. View at Google Scholar · View at Scopus
  29. S. Farooq, 555 Medicinal Plants. Field and Laboratory Manual, International Book Distributors, Dehradun, India, 2005.
  30. E. D. Kharasch, D. C. Hankins, and J. K. Taraday, “Single-dose methoxsalen effects on human cytochrome P-450 2A6 activity,” Drug Metabolism and Disposition, vol. 28, no. 1, pp. 28–33, 2000. View at Google Scholar · View at Scopus
  31. S. Chakthong, P. Weaaryee, P. Puangphet et al., “Alkaloid and coumarins from the green fruits of Aegle marmelos,” Phytochemistry, vol. 75, pp. 108–113, 2012. View at Publisher · View at Google Scholar
  32. A. Basile, S. Sorbo, V. Spadaro et al., “Antimicrobial and antioxidant activities of coumarins from the roots of Ferulago campestris (apiaceae),” Molecules, vol. 14, no. 3, pp. 939–952, 2009. View at Publisher · View at Google Scholar · View at Scopus
  33. A. D. Patil, A. J. Freyer, D. S. Eggleston et al., “The inophyllums, novel inhibitors of HIV-1 reverse transcriptase isolated from the Malaysian tree, Calophyllum inophyllum Linn,” Journal of Medicinal Chemistry, vol. 36, no. 26, pp. 4131–4138, 1993. View at Google Scholar · View at Scopus
  34. Y. Kashman, K. R. Gustafson, R. W. Fuller et al., “The calanolides, a novel HIV-inhibitory class of coumarin derivatives from the tropical rainforest tree, Calophyllum lanigerum,” Journal of Medicinal Chemistry, vol. 35, no. 15, pp. 2735–2743, 1992. View at Google Scholar · View at Scopus
  35. R. A. Newman, W. Chen, and T. L. Madden, “Pharmaceutical properties of related calanolide compounds with activity against human immunodeficiency virus,” Journal of Pharmaceutical Sciences, vol. 87, no. 9, pp. 1077–1080, 1998. View at Publisher · View at Google Scholar · View at Scopus
  36. T. C. McKee, R. W. Fuller, C. D. Covington et al., “New pyranocoumarins isolated from Calophyllum lanigerum and Calophyllum teysmannii,” Journal of Natural Products, vol. 59, no. 8, pp. 754–758, 1996. View at Publisher · View at Google Scholar · View at Scopus
  37. L. Crombie, D. E. Games, and A. McCormick, “Isolation and structure of mammea A/BA, A/AB and A/BB: a group of 4-aryl-coumarin extractives of Mammea americana L,” Tetrahedron Letters, vol. 7, no. 2, pp. 145–149, 1966. View at Google Scholar · View at Scopus
  38. S. K. Poole and C. F. Poole, “Thin-layer chromatographic method for the determination of the principal polar aromatic flavour compounds of the cinnamons of commerce,” The Analyst, vol. 119, no. 1, pp. 113–120, 1994. View at Publisher · View at Google Scholar · View at Scopus
  39. G. J. Huang, J. S. Deng, J. C. Liao et al., “Inducible nitric oxide synthase and cyclooxygenase-2 participate in anti-inflammatory activity of imperatorin from Glehnia littoralis,” Journal of Agricultural and Food Chemistry, vol. 60, no. 7, pp. 1673–1681, 2012. View at Publisher · View at Google Scholar
  40. A. Nadkarni, Nadkarni's Indian Materia Medica, vol. 1, Popular Prakashan Pvt. Ltd., Bombay, India, 1976.
  41. W. S. Chang, Y. H. Chang, F. J. Lu, and H. C. Chiang, “Inhibitory effects of phenolics on xanthine oxidase,” Anticancer Research, vol. 14, no. 2A, pp. 501–506, 1994. View at Google Scholar · View at Scopus
  42. O. S. Kwon, J. S. Choi, M. N. Islam et al., “Inhibition of 5-lipoxygenase and skin inflammation by the aerial parts of Artemisia capillaris and its constituents,” Archives of Pharmacal Research, vol. 34, no. 9, pp. 1561–1569, 2011. View at Google Scholar
  43. K. C. Fylaktakidou, D. J. Hadjipavlou-Litina, K. E. Litinas, and D. N. Nicolaides, “Natural and synthetic coumarin derivatives with anti-inflammatory/antioxidant activities,” Current Pharmaceutical Design, vol. 10, no. 30, pp. 3813–3833, 2004. View at Publisher · View at Google Scholar · View at Scopus
  44. J. Hirsh, J. E. Dalen, D. R. Anderson et al., “Oral anticoagulants: mechanism of action, clinical effectiveness, and optimal therapeutic range,” Chest, vol. 119, no. 1, supplement, pp. 8S–21S, 2001. View at Google Scholar · View at Scopus
  45. G. L. Nelsestuen, T. H. Zytkovicz, and J. B. Howard, “The mode of action of vitamin K. Identification of γ carboxyglutamic acid as a component of prothrombin,” The Journal of Biological Chemistry, vol. 249, no. 19, pp. 6347–6350, 1974. View at Google Scholar · View at Scopus
  46. J. Stenflo, P. Fernlund, W. Egan, and P. Roepstorff, “Vitamin K dependent modifications of glutamic acid residues in prothrombin,” Proceedings of the National Academy of Sciences of the United States of America, vol. 71, no. 7, pp. 2730–2733, 1974. View at Google Scholar · View at Scopus
  47. D. S. Whitlon, J. A. Sadowski, and J. W. Suttie, “Mechanism of coumarin action: significance of vitamin K epoxide reductase inhibition,” Biochemistry, vol. 17, no. 8, pp. 1371–1377, 1978. View at Google Scholar · View at Scopus
  48. L. S. Trivedi, M. Rhee, J. H. Galivan, and M. J. Fasco, “Normal and warfarin-resistant rat hepatocyte metabolism of vitamin K 2,3-epoxide: evidence for multiple pathways of hydroxyvitamin K formation,” Archives of Biochemistry and Biophysics, vol. 264, no. 1, pp. 67–73, 1988. View at Google Scholar · View at Scopus
  49. M. J. Fasco, E. F. Hildebrandt, and J. W. Suttie, “Evidence that warfarin anticoagulant action involves two distinct reductase activities,” The Journal of Biological Chemistry, vol. 257, no. 19, pp. 11210–11212, 1982. View at Google Scholar · View at Scopus
  50. I. A. Choonara, R. G. Malia, B. P. Haynes et al., “The relationship between inhibition of vitamin K1 2,3-epoxide reductase and reduction of clotting factor activity with warfarin,” British Journal of Clinical Pharmacology, vol. 25, no. 1, pp. 1–7, 1988. View at Google Scholar · View at Scopus
  51. P. A. Friedman, R. D. Rosenberg, P. V. Hauschka, and A. Fitz-James, “A spectrum of partially carboxylated prothrombins in the plasmas of coumarin-treated patients,” Biochimica et Biophysica Acta, vol. 494, no. 1, pp. 271–276, 1977. View at Google Scholar · View at Scopus
  52. O. P. Malhotra, M. E. Nesheim, and K. G. Mann, “The kinetics of activation of normal and γ-carboxyglutamic acid-deficient prothrombins,” The Journal of Biological Chemistry, vol. 260, no. 1, pp. 279–287, 1985. View at Google Scholar · View at Scopus
  53. G. L. Nelsestuen, “Role of γ carboxyglutamic acid. An unusual protein transition required for the calcium dependent binding of prothrombin to phospholipid,” The Journal of Biological Chemistry, vol. 251, no. 18, pp. 5648–5656, 1976. View at Google Scholar · View at Scopus
  54. F. G. Prendergast and K. G. Mann, “Differentiation of metal ion induced transitions of prothrombin fragment 1,” The Journal of Biological Chemistry, vol. 252, no. 3, pp. 840–850, 1977. View at Google Scholar · View at Scopus
  55. M. Borowski, B. C. Furie, S. Bauminger, and B. Furie, “Prothrombin requires two sequential metal-dependent conformational transitions to bind phospholipid. Conformation-specific antibodies directed against the phospholipid-binding site on prothrombin,” The Journal of Biological Chemistry, vol. 261, no. 32, pp. 14969–14975, 1986. View at Google Scholar · View at Scopus
  56. N. I. Baek, E. M. Ahn, H. Y. Kim, and Y. D. Park, “Furanocoumarins from the root of Angelica dahurica,” Archives of Pharmacal Research, vol. 23, no. 5, pp. 467–470, 2000. View at Google Scholar · View at Scopus
  57. S. B. Raja, M. R. Murali, K. Roopa et al., “Imperatorin a furocoumarin inhibits periplasmic Cu-Zn SOD of Shigella dysenteriae their by modulates its resistance towards phagocytosis during host pathogen interaction,” Biomedicine & Pharmacotherapy, vol. 65, no. 8, pp. 560–568, 2011. View at Google Scholar
  58. S. Hestrin, D. S. Feingold, and G. Avigad, “Synthesis of sucrose and other β-D-fructofuranosyl aldosides by levansucrase,” Journal of the American Chemical Society, vol. 77, no. 24, p. 6710, 1955. View at Google Scholar · View at Scopus
  59. C. M. Teng, C. H. Lin, F. N. Ko, T. S. Wu, and T. F. Huang, “The relaxant action of osthole isolated from Angelica pubescens in guinea-pig trachea,” Naunyn-Schmiedeberg's Archives of Pharmacology, vol. 349, no. 2, pp. 202–208, 1994. View at Google Scholar · View at Scopus
  60. S. Y. Chou, C. S. Hsu, K. T. Wang, M. C. Wang, and C. C. Wang, “Antitumor effects of osthol from Cnidium monnieri: an in vitro and in vivo study,” Phytotherapy Research, vol. 21, no. 3, pp. 226–230, 2007. View at Publisher · View at Google Scholar · View at Scopus
  61. W. Cisowski, U. Sawicka, M. Mardarowicz, M. Asztemborska, and M. Luczkiewicz, “Essential oil from herb and rhizome of Peucedanum ostruthium (L. Koch.) ex DC,” Zeitschrift für Naturforschung C, vol. 56, no. 11-12, pp. 930–932, 2001. View at Google Scholar · View at Scopus
  62. G. H. Stout and K. L. Stevens, “The structure of costatolide,” Journal of Organic Chemistry, vol. 29, no. 12, pp. 3604–3609, 1964. View at Google Scholar · View at Scopus
  63. R. Sancho, N. Márquez, M. Gómez-Gonzalo et al., “Imperatorin inhibits HIV-1 replication through an Sp1-dependent pathway,” The Journal of Biological Chemistry, vol. 279, no. 36, pp. 37349–37359, 2004. View at Publisher · View at Google Scholar · View at Scopus
  64. K. W. Luo, J. G. Sun, J. Y. Chan et al., “Anticancer effects of imperatorin isolated from Angelica dahurica: induction of apoptosis in HepG2 cells through both death-receptor and mitochondria-mediated pathways,” Chemotherapy, vol. 57, no. 6, pp. 449–459, 2011. View at Publisher · View at Google Scholar
  65. D. Yang, T. Gu, T. Wang, Q. Tang, and C. Ma, “Effects of osthole on migration and invasion in breast cancer cells,” Bioscience, Biotechnology and Biochemistry, vol. 74, no. 7, pp. 1430–1434, 2010. View at Publisher · View at Google Scholar · View at Scopus
  66. E. S. Yun, S. S. Park, H. C. Shin et al., “p38 MAPK activation is required for esculetin-induced inhibition of vascular smooth muscle cells proliferation,” Toxicology in Vitro, vol. 25, no. 7, pp. 1335–1342, 2011. View at Publisher · View at Google Scholar
  67. C. R. Lee, E. J. Shin, H. C. Kim et al., “Esculetin inhibits N-methyl-D-aspartate neurotoxicity via glutathione preservation in primary cortical cultures,” Laboratory Animal Research, vol. 27, no. 3, pp. 259–263, 2011. View at Publisher · View at Google Scholar
  68. E. G. Crichton and P. G. Waterman, “Dihydromammea C/OB: a new coumarin from the seed of Mammea africana,” Phytochemistry, vol. 17, no. 10, pp. 1783–1786, 1978. View at Google Scholar · View at Scopus
  69. C. H. Schwalbe and P. G. Waterman, “Structure of 5, 7-dihydroxy-8-(2-methylbutyryl)-4-n-pentyl-3, 4-dihydrocoumarin (dihydromammea C/OB), C19H26O5,” Acta Crystallographica Section C, vol. 39, no. 4, pp. 499–502, 1983. View at Google Scholar
  70. P. E. Nguelefack-Mbuyo, T. B. Nguelefack, A. B. Dongmo et al., “Anti-hypertensive effects of the methanol/methylene chloride stem bark extract of Mammea africana in l-NAME-induced hypertensive rats,” Journal of Ethnopharmacology, vol. 117, no. 3, pp. 446–450, 2008. View at Publisher · View at Google Scholar · View at Scopus
  71. M. C. Tchamadeu, P. D. D. Dzeufiet, C. C. K. Nouga et al., “Hypoglycaemic effects of Mammea africana (Guttiferae) in diabetic rats,” Journal of Ethnopharmacology, vol. 127, no. 2, pp. 368–372, 2010. View at Publisher · View at Google Scholar · View at Scopus
  72. T. Namba, O. Morita, S. L. Huang, K. Goshima, M. Hattori, and N. Kakiuchi, “Studies on cardio-active crude drugs; I. Effect of coumarins on cultured myocardial cells,” Planta Medica, vol. 54, no. 4, pp. 277–282, 1988. View at Google Scholar · View at Scopus
  73. D. Gantimur, A. I. Syrchina, and A. A. Semenov, “Khellactone derivatives from Phlojodicarpus sibiricus,” Chemistry of Natural Compounds, vol. 22, no. 1, pp. 103–104, 1986. View at Publisher · View at Google Scholar · View at Scopus
  74. J. J. Luszczki, E. Wojda, M. Andres-Mach et al., “Anticonvulsant and acute neurotoxic effects of imperatorin, osthole and valproate in the maximal electroshock seizure and chimney tests in mice: a comparative study,” Epilepsy Research, vol. 85, no. 2-3, pp. 293–299, 2009. View at Publisher · View at Google Scholar · View at Scopus
  75. X. Chen, R. Pi, Y. Zou et al., “Attenuation of experimental autoimmune encephalomyelitis in C57 BL/6 mice by osthole, a natural coumarin,” European Journal of Pharmacology, vol. 629, no. 1–3, pp. 40–46, 2010. View at Publisher · View at Google Scholar · View at Scopus
  76. M. Tinel, J. Belghiti, V. Descatoire et al., “Inactivation of human liver cytochrome P-450 by the drug methoxsalen and other psoralen derivatives,” Biochemical Pharmacology, vol. 36, no. 6, pp. 951–955, 1987. View at Google Scholar · View at Scopus
  77. N. Y. Kim, H. O. Pae, Y. S. Ko et al., “In vitro inducible nitric oxide synthesis inhibitory active constituents from Fraxinus rhynchophylla,” Planta Medica, vol. 65, no. 7, pp. 656–658, 1999. View at Publisher · View at Google Scholar · View at Scopus
  78. D. M. Fort, K. Rao, S. D. Jolad, J. Luo, T. J. Carlson, and S. R. King, “Antihyperglycemic activity of Teramnus labialis (Fabaceae),” Phytomedicine, vol. 6, no. 6, pp. 465–467, 2000. View at Google Scholar · View at Scopus
  79. S. H. Kim, K. A. Kang, R. Zhang et al., “Protective effect of esculetin against oxidative stress-induced cell damage via scavenging reactive oxygen species,” Acta Pharmacologica Sinica, vol. 29, no. 11, pp. 1319–1326, 2008. View at Publisher · View at Google Scholar · View at Scopus
  80. A. M. Hirsch, A. Longeon, and M. Guyot, “Fraxin and esculin: two coumarins specific to Actinidia chinensis and A. deliciosa (kiwifruit),” Biochemical Systematics and Ecology, vol. 30, no. 1, pp. 55–60, 2002. View at Publisher · View at Google Scholar · View at Scopus
  81. C. Wang, A. Pei, J. Chen et al., “A natural coumarin derivative esculetin offers neuroprotection on cerebral ischemia/reperfusion injury in mice,” Journal of Neurochemistry, vol. 121, no. 6, pp. 1007–1013, 2012. View at Publisher · View at Google Scholar
  82. D. Guilet, D. Séraphin, D. Rondeau, P. Richomme, and J. Bruneton, “Cytotoxic coumarins from Calophyllum dispar,” Phytochemistry, vol. 58, no. 4, pp. 571–575, 2001. View at Publisher · View at Google Scholar · View at Scopus
  83. L. Crombie, D. E. Games, N. J. Haskins, and G. F. Reed, “Extractives of Mammea americana L—part III: Identification of new coumarin relatives of mammea B/BA, B/BB, and B/BC having 5,6-annulation and higher oxidation levels,” Journal of the Chemical Society, Perkin Transactions 1, vol. 1972, pp. 2241–2248, 1972. View at Publisher · View at Google Scholar · View at Scopus
  84. C. C. Chiang, M. J. Cheng, H. Y. Huang, H. S. Chang, C. J. Wang, and I. S. Chen, “Prenyl coumarins from Fatoua pilosa,” Journal of Natural Products, vol. 73, no. 10, pp. 1718–1722, 2010. View at Publisher · View at Google Scholar · View at Scopus
  85. A. V. Lozhkin and E. I. Sakanyan, “Natural coumarins: methods of isolation and analysis,” Pharmaceutical Chemistry Journal, vol. 40, no. 6, pp. 337–346, 2006. View at Publisher · View at Google Scholar · View at Scopus