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      Inhibitory Activity of Coumarins from Artemisia capillaris against Advanced Glycation Endproduct Formation

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      https://www.riss.kr/link?id=A103889554

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      Since glycation can lead to the onset of diabetic complications due to chronic hyperglycemia, several indigenous Artemisia species were evaluated as potential inhibitors of advanced glycation endproducts (AGE). Among them, the Artemisia capillaris plant demonstrated the highest AGE inhibitory activity. Repeated column chromatography was performed to isolate a new acylated flavonoid glycoside, acacetin-7-O-(6''-O-acetyl)-β-D-glucopyranosyl-(1→2)[α-L-rhamnopyranosyl]-(1→6)-β-D-glucopyranoside, along with 11 known flavonoids (acacetin-7-O-β-Dglucopyranosyl-(1→2)[α-L-rhamnopyranosyl]-(1→6)-β-D-glucopyranoside, linarin, quercetin, hyperoside, isorhamnetin, isorhamnetin 3-galactoside, isorhamnetin 3-glucoside, isorhamnetin 3-arabinoside, isorhamnetin 3-robinobioside, arcapillin, and cirsilineol), six coumarins (umbelliferone, esculetin, scopoletin, scopolin, isoscopolin, and scoparone), and two phenolic derivatives (4,5-di-O-caffeoylquinic acid and chlorogenic acid). In determining the structure-activity relationship (SAR), it was found that the presence and position of hydroxyl group of test coumarins (coumarin, esculin, isoscopoletin, daphnetin, 4-methylcoumarin, and six isolated coumarins) may play a crucial role in AGE inhibition. A free hydroxyl group at C-7 and a glucosyl group instead of a methoxyl group at C-6 are two important parameters for the inhibitory potential of coumarins on AGE formation. A. capillaris and five key AGE inhibitors, including 4,5-di-Ocaffeoylquinic acid, umbelliferone, esculetin, esculin, and scopoletin, were identified as potential candidates for use as therapeutic or preventive agents for diabetic complications and oxidative stress-related diseases. We understand this to be the first detailed study on the SAR of coumarins in AGE inhibition.
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      Since glycation can lead to the onset of diabetic complications due to chronic hyperglycemia, several indigenous Artemisia species were evaluated as potential inhibitors of advanced glycation endproducts (AGE). Among them, the Artemisia capillaris pla...

      Since glycation can lead to the onset of diabetic complications due to chronic hyperglycemia, several indigenous Artemisia species were evaluated as potential inhibitors of advanced glycation endproducts (AGE). Among them, the Artemisia capillaris plant demonstrated the highest AGE inhibitory activity. Repeated column chromatography was performed to isolate a new acylated flavonoid glycoside, acacetin-7-O-(6''-O-acetyl)-β-D-glucopyranosyl-(1→2)[α-L-rhamnopyranosyl]-(1→6)-β-D-glucopyranoside, along with 11 known flavonoids (acacetin-7-O-β-Dglucopyranosyl-(1→2)[α-L-rhamnopyranosyl]-(1→6)-β-D-glucopyranoside, linarin, quercetin, hyperoside, isorhamnetin, isorhamnetin 3-galactoside, isorhamnetin 3-glucoside, isorhamnetin 3-arabinoside, isorhamnetin 3-robinobioside, arcapillin, and cirsilineol), six coumarins (umbelliferone, esculetin, scopoletin, scopolin, isoscopolin, and scoparone), and two phenolic derivatives (4,5-di-O-caffeoylquinic acid and chlorogenic acid). In determining the structure-activity relationship (SAR), it was found that the presence and position of hydroxyl group of test coumarins (coumarin, esculin, isoscopoletin, daphnetin, 4-methylcoumarin, and six isolated coumarins) may play a crucial role in AGE inhibition. A free hydroxyl group at C-7 and a glucosyl group instead of a methoxyl group at C-6 are two important parameters for the inhibitory potential of coumarins on AGE formation. A. capillaris and five key AGE inhibitors, including 4,5-di-Ocaffeoylquinic acid, umbelliferone, esculetin, esculin, and scopoletin, were identified as potential candidates for use as therapeutic or preventive agents for diabetic complications and oxidative stress-related diseases. We understand this to be the first detailed study on the SAR of coumarins in AGE inhibition.

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      참고문헌 (Reference)

      1 서경순, "인진(茵蔯)으로 쓰이는 사철쑥과 더위지기 추출물의 항산화 활성" 한국자원식물학회 21 (21): 292-298, 2008

      2 Li, H., "XLF-III-43, a novel coumarin−aspirin compound, prevents diabetic nephropathy in rats via inhibiting advanced glycation end products" 627 : 340-347, 2010

      3 Altan, V. M., "The pharmacology of diabetic complications" 10 : 1317-1327, 2003

      4 Yamahara, J., "The effect of scoparone, a coumarin derivative isolated from the Chinese crude drug Artemisiae capillaris flos, on the heart" 37 : 1297-1299, 1989

      5 Hong, S. H., "The aqueous extract from Artemisia capillaris Thunb. inhibits lipopolysaccharide-induced inflammatory response through preventing NF-κB activation in human hepatoma cell line and rat liver" 13 : 717-720, 2004

      6 Park, K. H., "The antioxidative and anti-inflammatory effects of caffeoyl derivatives from the roots of Aconitum koreanum R. RAYMOND" 32 : 2029-2033, 2009

      7 여지영, "The anti-diabetic effects of ethanol extract from two variants of Artemisia princeps Pampanini in C57BL/KsJ-db/db mice" PERGAMON-ELSEVIER SCIENCE LTD 45 : 2022-2029, 200710

      8 Matsuda, H., "Structural requirements of flavonoids for inhibition of protein glycation and radical scavenging activities" 11 : 5317-5323, 2003

      9 Kordali, S., "Screening of chemical composition and antifungal and antioxidant activities of the essential oils from three Turkish Artemisia species" 53 : 1408-1416, 2005

      10 Seon Il Jang, "Scoparone from Artemisia capillaris Inhibits the Release of Inflammatory Mediators in RAW 264.7 Cells upon Stimulation Cells by Interferon-γ Plus LPS" 대한약학회 28 (28): 203-208, 2005

      1 서경순, "인진(茵蔯)으로 쓰이는 사철쑥과 더위지기 추출물의 항산화 활성" 한국자원식물학회 21 (21): 292-298, 2008

      2 Li, H., "XLF-III-43, a novel coumarin−aspirin compound, prevents diabetic nephropathy in rats via inhibiting advanced glycation end products" 627 : 340-347, 2010

      3 Altan, V. M., "The pharmacology of diabetic complications" 10 : 1317-1327, 2003

      4 Yamahara, J., "The effect of scoparone, a coumarin derivative isolated from the Chinese crude drug Artemisiae capillaris flos, on the heart" 37 : 1297-1299, 1989

      5 Hong, S. H., "The aqueous extract from Artemisia capillaris Thunb. inhibits lipopolysaccharide-induced inflammatory response through preventing NF-κB activation in human hepatoma cell line and rat liver" 13 : 717-720, 2004

      6 Park, K. H., "The antioxidative and anti-inflammatory effects of caffeoyl derivatives from the roots of Aconitum koreanum R. RAYMOND" 32 : 2029-2033, 2009

      7 여지영, "The anti-diabetic effects of ethanol extract from two variants of Artemisia princeps Pampanini in C57BL/KsJ-db/db mice" PERGAMON-ELSEVIER SCIENCE LTD 45 : 2022-2029, 200710

      8 Matsuda, H., "Structural requirements of flavonoids for inhibition of protein glycation and radical scavenging activities" 11 : 5317-5323, 2003

      9 Kordali, S., "Screening of chemical composition and antifungal and antioxidant activities of the essential oils from three Turkish Artemisia species" 53 : 1408-1416, 2005

      10 Seon Il Jang, "Scoparone from Artemisia capillaris Inhibits the Release of Inflammatory Mediators in RAW 264.7 Cells upon Stimulation Cells by Interferon-γ Plus LPS" 대한약학회 28 (28): 203-208, 2005

      11 Kheterpal, I., "Regulation of insulin action by an extract of Artemisia dracunculus L. in primary human skeletal muscle culture : a proteomics approach" 24 : 1278-1284, 2010

      12 Pari, L., "Protective role of coumarin on plasma and tissue glycoprotein components in streptozotocin-nicotinamide induced hyperglycemic rats" 1 : 61-65, 2010

      13 Choi, J. H., "Protective effects of hyperoside against carbon tetrachloride-induced liver damage in mice" 74 : 1055-1060, 2011

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      18 Li, H., "Nicousamide blocks the effects of advanced glycation end products on renal cells" 674 : 455-459, 2012

      19 Stefek, M., "Natural flavonoids as potential multifunctional agents in prevention of diabetic cataract" 4 : 69-77, 2011

      20 Chen, Y. L., "Morphological evidence for the antiatherogenic effect of scoparone in hyperlipidaemic diabetic rabbits" 28 : 1679-1685, 1994

      21 Seon Hwa Jeong, "Monoamine Oxidase Inhibitory Coumarins from the Aerial Parts of Dictamnus albus" 대한약학회 29 (29): 1119-1124, 2006

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      23 이연실, "Inhibitory effects of isorhamnetin-3-O-beta-D-glucoside from Salicornia herbacea on rat lens aldose reductase and sorbitol accumulation in streptozotocin-induced diabetic rat tissues" PHARMACEUTICAL SOC JAPAN 28 : 916-918, 200505

      24 Cheng-Bi Cui, "Inhibitory Activity of Caffeoylquinic Acids from the Aerial Parts of Artemisia princeps on Rat Lens Aldose Reductase and on the Formation of Advanced Glycation End Products" 한국응용생명화학회 52 (52): 655-662, 2009

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      27 Oh Song Kwon, "Inhibition of 5-Lipoxygenase and Skin Inflammation by the Aerial Parts of Artemisia capillaris and its Constituents" 대한약학회 34 (34): 1561-1569, 2011

      28 Ribnicky, D. M., "Improved absorption and bioactivity of active compounds from an anti-diabetic extract of Artemisia dracunculus L" 370 : 87-92, 2009

      29 Nakatani, N., "Identification, quantitative determination, and antioxidative activities of chlorogenic acid isomers in Prune(Prunus domestica L. )" 48 : 5512-5516, 2000

      30 Nicolle, E., "Flavonoids as promising lead compounds in type 2 diabetes mellitus : molecules of interest and structure-activity relationship" 18 : 2661-2672, 2011

      31 Veitch, N. C., "Flavonoid glycosides of the black locust tree, Robinia psedoacacia(Leguminosiae)" 71 : 479-486, 2010

      32 Nazaruk, J., "Flavonoid compounds from the flowers of Cirsium rivulare(Jacq. )All" 60 : 87-89, 2003

      33 Jung, H. A., "Extraction and identification of three major aldose reductase inhibitors from Artemisia montana" 49 : 376-384, 2011

      34 Cha, J. D., "Essential oil of Artemisia capillaris induces apoptosis in KB cells via mitochondrial stress and caspase activation mediated by MAPK-stimulated signaling pathway" 74 : T75-81, 2009

      35 Pari, L., "Efficacy of coumarin on hepatic key enzymes of glucose metabolism in chemical induced type 2 diabetic rats" 181 : 292-296, 2009

      36 Lee, C. J., "Effects of Artemisiae capillaris Fructus on experimental liver damage by carbon tetrachloride" 21 : 100-107, 2000

      37 Hong, J. H., "Effects of Artemisia capillaris ethyl acetate fraction on oxidative stress and antioxidant enzyme in high-fat diet induced obese mice" 179 : 88-93, 2009

      38 Ramesh, B., "Effect of umbelliferone on tail tendon collagen and haemostatic function in streptozotocindiabetic rats" 101 : 73-77, 2007

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      40 Tsukamoto, H., "Coumarin and secoiridoid glucosides from bark of Olea africana and Olea capensis" 33 : 396-399, 1985

      41 Hyun Young Park, "Constituents of the Stem of Angelica gigas with Rat Lens Aldose Reductase Inhibitory Activity" 한국응용생명화학회 54 (54): 194-199, 2011

      42 Bayoumi, S. A., "Constituents and secondary metabolite natural products in fresh and deteriorated cassava roots" 71 : 598-604, 2010

      43 Lee, H. -I., "Comparative study of the hepatoprotective efficacy of Artemisia iwayomogi and Artemisia capillaris on ethanoladministered mice" T207-T211, 2011

      44 Yook, C. S., "Coloured medicinal plants in Korea" Academic Publishing Co 431-432, 1989

      45 Kochakian, M., "Chronic dosing with aminoguanidine and novel advanced glycosylation end product-formation inhibitors ameliorates cross-linking of tail tendon collagen in STZ-induced diabetic rats" 45 : 1694-1700, 1996

      46 Okuno, I., "Choleretic effect of Artemisia capillaris extract in rats" 31 : 835-838, 1981

      47 Tang, W., "Chinese Drugs of Plant Origin, Chemistry, Phamacology and use in traditional and modern medicine" Springer Verlag 179-, 1992

      48 Kariyone, T., "Chemical constituents of the plants of Coniferae and allied orders XXXIII A new glycoside, distichin, and other constituents of the leaves of Taxodium distichum" 80 : 102-105, 1960

      49 Liu, Z. L., "Chemical composition and insecticidal activity against Sitophilus zeamais of the essential oils of Artemisia capillaris and Artemisia mongolica" 15 : 2600-2608, 2010

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      55 Jung-Hee Hong, "Artemisia capillaris Inhibits Lipid Accumulation in 3T3-L1 Adipocytes and Obesity in C57BL/6J Mice Fed a High Fat Diet" 한국식품영양과학회 12 (12): 736-745, 2009

      56 Hong, J. H., "Antioxidative and cytoprotective effects of Artemisia capillaris fractions" 31 : 43-53, 2007

      57 Rajarajeswari, N., "Antioxidant role of coumarin on streptozotocin−nicotinamide-induced type 2 diabetic rats" 25 : 355-361, 2011

      58 Yokozawa, T., "Antioxidant effects of isorhamnetin 3, 7-di-O-β-D-glucopyranoside isolated from mustard leaf(Brassica juncea)in rats with streptozotocin-induced diabetes" 50 : 5490-5495, 2002

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      62 서경순, "Antimicrobial activity and chemical components of two plants, Artemisia capillaris and Artemisia iwayomogi, used as Korean herbal Injin" 한국생태학회 33 (33): 141-147, 2010

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      65 Bum-Chun Lee, "Anti-oxidative and Photo-protective Effects of Coumarins Isolated from Fraxinus chinensis" 대한약학회 30 (30): 1293-1301, 2007

      66 de la Fuente, J. A., "Aldose reductase inhibitors from natural sources" 20 : 243-251, 2003

      67 Ahmed, N., "Advanced glycation endproducts--role in pathology of diabetic complications" 67 : 3-21, 2005

      68 Peyrou, J., "Advanced glycation endproducts(AGEs) : Pharmacological inhibition in diabetes" 54 : 405-419, 2006

      69 Ahmed, N., "Advanced glycation endproducts : what is their relevance to diabetic complications?" 9 : 233-245, 2007

      70 Sasaki, N., "Advanced glycation end products in Alzheimer's disease and other neurodegenerative diseases" 153 : 1149-1155, 1998

      71 Kato, A., "6, 7-Dihydroxy-4-phenylcoumarin as inhibitor of aldose reductase 2" 20 : 5630-5633, 2010

      72 Wawer, I., "13C CP/MAS NMR studies of flavonoids" 10 : 33-38, 2001

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