Pharmacological Effect of Decursin and Decursinol Angelate from Angelica gigas Nakai |
Son, Chu-Young
(Department of Pharmacy, Chungnam University)
Baek, In-Hwan (Department of Pharmacy, Chungnam University) Song, Gyu-Yong (Department of Pharmacy, Chungnam University) Kang, Jae-Seon (Department of Pharmacy, Kyungsung University) Kwon, Kwang-Il (Department of Pharmacy, Chungnam University) |
1 | 생약학교재편찬위원회 : 생약학 제5개정판, 동명사, 서울 (2006) |
2 | Jung, D. J., Porzel, A. and Huneck, S. : Gigasol and other coumarins from Angelica gigas. Phytochemistry 30, 710(1991) DOI ScienceOn |
3 | Rye, K. S., Hong, N. D., Kim, N. J. and Kong, Y. Y. : Studies on the coumarin constituents of the root of Angelica gigas Nakai Isolation of decursinol angelate and assay of decursinol angelate and decursin. Kor. J. Pharmacogn. 21, 64 (1990) |
4 | 한국보건산업진흥원 : 국내외 천연물의약품 연구개발 동향, 제 2차 천연물 신약 연구개발 촉진 계획 (2006) |
5 | Adams, J. D., Flora, K. P., Goldspiel, B. R., Wilson, J. W., Arbuck, S. G. and Finley, R. : Taxol: a history of pharmaceutical development and current pharmaceutical concerns. J. Nati. Cancer. Inst. 15, 141 (1993) |
6 | Hata, K. and Sano, K. : The constitution of decursin, a new coumarin isolated from the root of Angelica decursiva. Tetrahedron Lett. 14, 1461 (1996) |
7 | Ganbaatar, Z., Gantumur, B., Osadchii, S. A., Shul’ts, E. E., Shakirov, M. M. and Tolstikov, G. A. : Plant coumarins. 3. (+)- PTeryxin from Peucedanum terebinthaceum. Chemistry of Natural Compounds 44(5), 578 (2008) DOI ScienceOn |
8 | Ahn, K. S., Sim, W. S. and Kim, I. H. : Decursin: A cytotoxic agent and protein kinase C activator from the root of Angelica gigas. Plant. Medica 62(1), 7 (1995) DOI ScienceOn |
9 | Ng, T. B., Ling, J. M. L., Wang, Z. T., Cai, J. N. and Xu, G. J. : Examination of coumarins, flavonoid and polysaccharopeptide for antibacterial activity. Gen. Pharmac. 27(7), 1237 (1996) |
10 | Hentschel, E., Brandstatter, G., Dragosics, B., Hirschl, A. M., Nemec, H., Schutze, K., Taufer, M. and Wurzer, H. : Effect of ranitidine and amoxicillin plus metronidazole on the eradication of Helicobacter pylori and the recurrence of duodenal ulcer. N. Engl. J. Med. 328(5), 308 (1993) DOI ScienceOn |
11 | Yoo, H. H., Lee, M. W., Kim, Y. C., Yun, C. H. and Kim, D. H. : Mechanism-based inactivation of cytochrome P450 2A6 by decursinol angelate isolated from Angelica gigas. Drug. Metab. Dispos. 35(10), 1759 (2007) DOI ScienceOn |
12 | Chakraborti, S., Mandal, M., Das, S., Mandal, A. and Chakraborti, T. : Regulation of matrix metalloproteinases: an overview. Mol. Cell. Biochem. 253(1), 269 (2003) DOI ScienceOn |
13 | Tiano, H. F., Wang, R. L., Hosokawa, M., Crespi, C., Tindall, K. R. and Lanqenbach, R. : Human CYP2A6 activation of 4- (methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK): Mutational specificity in the GPT gene of AS52 cells. Carcinogenesis. 15(12), 2859 (1994) DOI ScienceOn |
14 | Ariyoshi, N., Miyamoto, M., Umetsu, Y., Kunitoh, H., Dosaka- Akita, H., Sawamura, Y. I., Yokota, J., Nemoto, N., Sato, K. and Kamataki, T. : Genetic polymorphism of CYP2A6 gene and tobacco-induced lung cancer risk in male smokers. Cancer. Epidemiol. Biomarkers. Prev. 11(9), 890 (2002) |
15 | Saidenbreg-Kermanac'h, N., Cohen-Solal, M., Bessis, N., De Vernejoul, M. C. and Boissier, M. C. : Role for osteoprotegerin in rheumatoid inflammation. Joint. Bone. Spine. 71(1), 9 (2004) DOI ScienceOn |
16 | Recknagel, R. O., Glende, E. A. Jr., Dolak, J. A. and Waller, R. L. : Mechanisms of carbon tetrachloride toxicity. Pharmacol. Therapeut. 43(1), 139 (1989) DOI ScienceOn |
17 | U. S Patent Application No. 2006/0159790 A1, Composition for preventing or treating dementia comprising a hydroxycinnamic acid derivative or an extract of a plant of genus Angelicae containing same |
18 | Vazquez-Mellado, J., Morales, E. M., Pacheco-Tena, C. and Vargas, R. B. : Relation between adverse events associated with allopurinol and renal function in patients with gout. Ann. Rheum Dis. 60, 981 (2001) DOI ScienceOn |
19 | Kang, S. Y. and Kim, Y. C. : Neuroprotective coumarins from the root of Angelica gigas: structure-activity relationships. Arch. Pharm. Res. 30(11), 1368 (2007) DOI ScienceOn |
20 | Fritsma, G., Engelmann, G. and Yousuf, M. : A review of platelet function and testing. Am. J. Med. Technol. 47(9), 723 (1981) |
21 | Lee, Y. Y., Lee, S., Jin, J. L. and Yun-Choi, H. S. : Platelet antiaggregatory effects of coumarins from the roots of Angelica genuflexa and A. gigas. Arch. Pharm. Res. 26(9), 723 (2003) DOI ScienceOn |
22 | Mace, K., Bowman, E. D., Vautravers, P., Shields, P. G., Harris, C. C. and Pfeifer, A. M. A. : Characterization of xenobioticmetabolising enzyme expression in human bronchial mucosa and peripheral lung tissues. Eur. J. Cancer. 34(6), 914 (1998) DOI ScienceOn |
23 | Kang, S. Y., Lee, K. Y., Sung, S. H., Park, M. J. and Kim, Y. C. : Coumarins isolated from Angelica gigas inhibit acetylcholinesterase: Structure-activity relationships. J. Nat. Prod. 64(5), 683 (2001) DOI ScienceOn |
24 | Adb El-Aty, A. M., Shah, S. S., Kim, B. M., Choi, J. H., Cho, H. J., Yi, H., Chang, B. J., Shin, H. C., Lee, K. B., Shimoda, M. and Shim, J. H. : In vitro inhibitory potential of decursin and decursinol angelate on the catalytic activity of cytochrome P- 450 1A1/2, 2D15, and 3A12 isoforms in canine hepatic microsomes. Arch. Pharm. Res. 31(11), 1425 (2008) DOI ScienceOn |
25 | Grana, X. and Premkumar Reddy, E. : Cell cycle control in mammalian cells: role of cyclins, cyclin-dependent kinase (CDKs), growth suppressor genes and cyclin-dependent kinase inhibitors (CDKIs). Oncogene. 11, 211 (1995) PUBMED |
26 | Yim, D., Singh, R. P., Agarwal, C., Lee, S., Chi, H. and Agarwal, R. : A novel anticancer agent, decursin, induces G1 arrest and apoptosis in human prostate carcinoma cells. Cancer. Res. 65(3), 1035 (2005) PUBMED |
27 | Feldman, B. J. and Feldman, D. : The development of androgen-independent prostate cancer: current status and future prospects. Prostate 61, 332 (2004) DOI ScienceOn |
28 | Lee, K. Y., Sung, S. H., Kim, S. H., Jang, Y. P., Oh, T. H. and Kim, Y. C. : Cognitive-enhancing activity of loganin isolated from Cornus officinalis in scopolamine-induced amnesic mice. Arch. Pharm. Res. 32(5), 677 (2009) DOI ScienceOn |
29 | Choi, Y. E., Ahn, H. and Ryu, J. H. : Polyacetylenes from Angelica gigas and their inhibitory activity on nitric oxide synthesis in activated macrophages. Biol. Pharm. Bull. 23, 884(2000) DOI PUBMED ScienceOn |
30 | Son, S. H., Kim, M. J., Chung, W. Y., Son, J. A., Kim, Y. S., Kim, Y. C., Kang, S. S., Lee, S. K. and Park, K. K. : Decursin and decursinol inhibit VEGF-induced angiogenesis by blocking the activation of extracellular signal-regulated kinase and c-Jun Nterminal kinase. Cancer Letters. 280(1), 86 (2009) DOI ScienceOn |
31 | Tsujii, M., Kawano, S., Tsuji, S., Fusamoto, H., Kamada, T. and Sata, N. : Mechanism of gastric mucosal damage induce by ammonia. Gastoenterol. 102(6), 1881 (1992) DOI PUBMED |
32 | Park, K. W., Choi, S. R., Hong, H. R., Kim, J. Y., Shon, M. Y. and Seo, K. I. : Biological activities of methanol extract of Angelica gigas Nakai. Korean J. Food Preserv. 14(6), 655 (2007) |
33 | Davies, P. and Maloney, A. J. : Selective loss of central cholinergic neurons in Alzheimer's disease. Lancet. 2(8000), 1403 (1976) PUBMED |
34 | Cushman, D. W. and Ondetti, M. A. : History of design of captopril and related inhibitors of angiotensin converting enzyme. Hypertension. 17, 589 (1991) DOI PUBMED |
35 | Lee, S., Shin, D. S., Kim, J. S., Oh, K. B. and Kang, S. S. : Antibacterial coumarins from Angelica gigas. Arch. Pharm. Res. 26(6), 449 (2003) DOI ScienceOn |
36 | 성상현, 박진호 : 천연물의약품의 현황과 전망. 보건벤처 최신 동향 및 이슈 리포트 14 (2007) |
37 | Park, K. W., Choi, S. R., Shon, M. Y., Jeong, I. Y., Kang, K. S., Lee, S. T., Shim, K. H. and Seo, K. I. : Cytotoxic effects of decursin from Angelica gigas Nakai in human cancer cells. J. Korean Soc. Food Sci. Nutr. 36(11), 1385 (2007) DOI ScienceOn |
38 | 김선우 : 제 2형 당뇨병에서 혈관 합병증의 병태생리. 대한내과학회지 64(1), 10 (2003) |
39 | Yang, X. F., Wang, N. P. and Zeng, F. D. : Effects of the active components of some Chinese herbs on drug-metabolizing enzymes. Zhongguo. Zhong. Yao. Za. Zhi. 27(5), 325 (2002) PUBMED |
40 | http://www.chemicalregister.com/Decursin/Suppliers/pid46920.htm |
41 | 한국약학대학협의회 위생약학분과회 : 예방약학 II 제3개정판., 신일상사, 서울 (2006) |
42 | Jung, M. H., Lee, S. H., Ahn, E. M. and Lee, Y. M. : Decursin and decursinol angelate inhibit VEGF-induced angiogenesis via suppression of the VEGFR-2-signaling pathway. Carcinogenesis 30(4), 655 (2009) DOI ScienceOn |
43 | Jedziniak, J. A. and Kinoshita, J. H. : Activators and inhibitors of lens aldose reductase. Invest. Ophthalmol. Vis. Sci. 10(5), 357 (1971) |
44 | Lee, S., Lee, Y. S., Jung, S. H., Shin, K. H., Kim, B. K. and Kang, S. S. : Anti-tumor activities of Decursinol angelate and decursin from Angelica gigas. Arch. Pharm. Res. 26(9), 727(2003) DOI ScienceOn |
45 | Eckardstein, A. Von., Nofer, J. R. and Assmann, G. : High density lipoprotein and arteriosclerosis: Role of cholesterol efflux and reverse cholesterol transport. Arterioscler. Thromb. Vasc. Biol. 21(1), 13 (2001) DOI PUBMED ScienceOn |
46 | F. Peter guengerich : Cytochrome P-450 3A4: Regulation and role in drug metabolism. Annu. Res. Pharmacol. Toxicol. 39(1), 1 (1999) DOI PUBMED ScienceOn |
47 | U. S Patent Application No. 2007/0264370 A1, Composition and methods for the treatment of joint pain using Angelica gigas Nakai extract and powder as combined with glucosamine sulfate, or chondroitin sulfate and HCl, of MSM, of aspirin, or celedrin, and as combinations thereof in powder, pill, capsule, spray, liquid, and gelcap form |
48 | Chi, H. J. and Kim, H. S. : Studies on essential oils of plants of Angelica genus in Korea (I)-essential oils of Angelicae gigantis radix. Kor. J. Pharmacogn. 19, 239 (1988) |
49 | 정세영 et al. : PCT/KR1999/00632, 데커신을 포함하는 의약조성물 |
50 | Bae, E. A., Han, M. J., Kim, N. J. and Kim, D. H. : Anti- Helicobacter pylori activity of herbal medicines. Biol. Pharm. Bull. 21(9), 990 (1998) DOI PUBMED ScienceOn |
51 | Chang, W. S. and Chiang, H. C. : Structure-activity relationship of coumarins in xanthine oxidase inhibition. Anticancer Research 15(5B), 1969 (1995) PUBMED |
52 | Rehman, S. U., Chohan, Z. H., Gulnaz, F. and Supuran, C. T. : In-vitro antibacterial, antifungal and cytotoxic activities of some coumarins and their metal complexes. J. Enzyme. Inhib. Med. Chem. 20(4), 333 (2005) DOI ScienceOn |
53 | Yang, E. J., Song, G. Y., Lee, J. S., Yun, C. Y. and Kim, I. S. : A novel (S)-(+)-Decursin derivative, (S)-(+)-3-(3,4-dihydroxyphenyl)- acrylic acid 2,2-dimethyl-8-oxo-3,4-dihydro-2H,8Hpyrano[3,2-g]-chromen-3-yl-ester, Inhibits ovalbumin-induced lung inflammation in a mouse model of asthma. Biol. Pharm. Bull 32(3), 444 (2009) DOI ScienceOn |
54 | http://www. healthpeople.co.kr |
55 | The American academy of veterinary pharmacology and therapeutics proceedings of the thirteenth biennial symposium, North Carolina (2003) |
56 | Kim, J. H., Jeong, J. H., Jeon, S. T., Kim, H., Ock, J. Y., Suk, K. H., Kim, S. I., Song, K. S. and Lee, W. H. : Decursin inhibits induction of inflammatory mediators by blocking nuclear factor-κB activation in macrophages. Mol. Pharmacol. 69(6), 1783 (2006) DOI ScienceOn |
57 | Heinlein, C. A. and Chang, C. : Androgen receptor in prostate cancer. Endocr. Res. 35, 276 (2004) |
58 | Pachaly, P., Treitner, A. and Sin, K. S. : New coumarin glycosides from Angelica gigas roots. Pharmazie. 51, 57 (1996) |
59 | http://www. Druginfo.co.kr |
60 | Caponigro, F., French, R. C. and Kaye, S. B. : Protein kinase C: a worthwhile target for anticancer drugs? Anticancer Drugs. 8(1), 26 (1887) DOI ScienceOn |
61 | Lee, S., Lee, Y. S., Jung, S. H., Shin, K. H. and Kim, B. K. : Antioxidant activities of decursinol angelate and decursin from Angelica gigas roots. Nat. Prod. Sci. 9(3), 170 (2003) |
62 | Kim, H. H., Ahn, K. S., Han, H., Choung, S. Y., Choi, S. Y. and Kim, I. H. : Decursin and PDBu: Two PKC activators distinctively acting in the megakaryocytic differentiation of K562 human erythroleukemia cells. Leuk. Res. 29, 1407(2005) DOI ScienceOn |
63 | Park, K W., Choi, S. R., Yang, H. S., Cho, H. W., Kang, K. S. and Seo, K. I. : Anti-proliferation effects of decursin from Angelica gigas Nakai in the MCF-7 cells treated with environmental hormones. J. Korean Soc. Food Sci. Nutr. 36(7), 825 (2007) DOI ScienceOn |
64 | Ohshiro, T., Namatame, I., Lee, E. W., Kawagishi, H. and Tomoda, H. : Molecular target of decursins in the inhibition of lipid droplet accumulation in macrophages. Biol. Pharm. Bull. 29(5), 981 (2006) DOI ScienceOn |
65 | Kang, S. Y., Lee, K. Y., Park, M. J., Kim, Y. C., Markelonis, G. J., Oh, T. H. and Kim, Y. C. : Decursin from Angelica gigas mitigates amnesia induced by scopolamine in mice. Neurobiol. Learn. Mem. 79(1), 11 (2003) DOI ScienceOn |
66 | Eaton, K. A., Brooks, C. L., Morgan, D. R. and Krakowka, S. : Essential role of urease in pathogenesis of gastritis induced by Helicobacter pylori in gnotobiotic piglets. Infec. Immun. 59(7), 2470 (1991) PUBMED |
67 | Konoshima, M., Chi, H. J. and Hata, K. : Coumarins from the root of Angelica gigas Nakai. Chem. Pharm. Bull. 16, 1139(1980) |
68 | 의약품등의 품목허가·신고·심사 규정, 식품의약품안전청 고시 제 2009-17호, (2009) |
69 | Jiang, C., Lee, H. J., Li, G. X., Gou, J., Malewicz, B., Zhao, Y., Lee, E. O., Lee, H. J., Lee, J. H., Kim, M. S., Kim, S. H. and Ju, J. : Potent antiandrogen and androgen receptor activities of an Angelica gigas-containing herbal formulation: Identification of Decursin as a novel and active compound with implications for prevention and treatment of prostate cancer. Cancer. Res. 66(1), 453, (2006) DOI ScienceOn |
70 | Moon, C. K., Lee, S. C., Yun, Y. P., Ha, B. J. and Yook, C. S. : Effect of some coumarin derivatives on the Bovine lens Aldose reductase activity. Arch. Pharm. Res. 11(4), 308 (1988) DOI ScienceOn |
71 | Libby, P., Ridker, P. M. and Maseri, A. : Inflammation and atherosclerosis. Circulation. 105(9), 1135 (2002) DOI ScienceOn |
72 | Kim, S. M., Yoon, S. H., Jeong, D. K., Han, J. H., Yu, W. Y., Lee, C. J., Kim, H. Y., Kang, S. J., Kim, D. S. and Kim, E. J. : A clinical study on the microvascular complication of Diabetes Mellitus. 당뇨병 17(3), 293 (1993) |
73 | Miles, J. S., Mclaren, A. W., Forrester, L. M., Glancey, M. J., Lang, M. A. and Wolf, C. R. : Identification of the human liver cytochrome P-450 responsible for coumarin 7-hydroxylase activity. Biochem. J. 267(2), 365 (1990) DOI |
74 | Lee, S. H., Kang, S. S. and Shin, K. H. : Coumarins and a pyrimidine from Angelica gigas roots. Nat. Prod. Sci. 8, 58 (2002) |
75 | Tepper, D., Ip, R. J. and Ip, J. H. : The use of antiplatelet agents in cardiac disease. Manag. Care. Interface. 13, 76 (2000) PUBMED |