Browse > Article
http://dx.doi.org/10.3839/jabc.2018.006

Chemical constituents of Dicentra spectabilis and their anti-inflammation effect  

Kim, A Hyeon (Division of Traditional Korean Medicine Resource, National Development Institute of Korea Medicine)
Jang, Ji Hun (Division of Traditional Korean Medicine Resource, National Development Institute of Korea Medicine)
Woo, Kyeong Wan (Division of Traditional Korean Medicine Resource, National Development Institute of Korea Medicine)
Park, Jong Eel (Division of Traditional Korean Medicine Resource, National Development Institute of Korea Medicine)
Lee, Ki Ho (Division of Traditional Korean Medicine Resource, National Development Institute of Korea Medicine)
Jung, Ho Kyung (Division of Traditional Korean Medicine Resource, National Development Institute of Korea Medicine)
An, Byeongkwan (Division of Traditional Korean Medicine Resource, National Development Institute of Korea Medicine)
Jung, Won Seok (Division of Traditional Korean Medicine Resource, National Development Institute of Korea Medicine)
Ham, Seong Ho (Division of Traditional Korean Medicine Resource, National Development Institute of Korea Medicine)
Cho, Hyun Woo (Division of Traditional Korean Medicine Resource, National Development Institute of Korea Medicine)
Publication Information
Journal of Applied Biological Chemistry / v.61, no.1, 2018 , pp. 39-46 More about this Journal
Abstract
Column chromatographic separation of the MeOH extract from the roots of Dicentra spectabilis yielded fourteen compounds, menisdaurin (1), menisdaurilide (2), trans-N-p-coumaroyltyramine (3), trans-N-p-feruloyltyramine (4), 4-O-feruloylquinicacid (5), chlorogenic acid (6), 3-O-feruloylquinicacid (7), ferulic acid (8), protopine (9), Kaempferol 3,7-di-O-${\beta}-{\text\tiny{D}}$-glucopyranoside (10), kaempferol 3-O-${\beta}-{\text\tiny{D}}$-glucopyranosyl-7-O-${\alpha}-{\text\tiny{L}}$-rhamnopyranoside (11), ${\alpha}-rhamnoisorobin$ (12), astragalin (13), and nicotiflorin (14). Their structures were determined on the basis of NMR spectroscopic data. Among them, compound 1, 3-8, and 10-14 isolated from this plant were reported for the first time. The isolated compounds (1-14) were tested for nitric oxide (NO) inhibitory activity on lipopolysaccharide-stimulated RAW 264.7 cells. Compound 3, 4 and 12 significantly inhibited NO production. Moreover, Compound 3 suppressed pro-inflammatory cytokines ($TNF-{\alpha}$, $IL-1{\beta}$ and IL-6) in a dose- dependent manner. These data suggest that compound 3 possess anti-inflammatory activity and might be useful natural materials for development of anti-inflammatory agent.
Keywords
Anti-inflammation effect; Dicentra spectabilis; Fumariaceae; Isolation; Structure elucidation;
Citations & Related Records
Times Cited By KSCI : 5  (Citation Analysis)
연도 인용수 순위
1 Zhao JW, Chen DS, Deng CS, Wang Q, Zhu W, Lin L (2017) Evaluation of anti-inflammatory activity of compounds isolated from the rhizome of Ophiopogon japonicas. BMC Complement Altern Med 17: 7   DOI
2 Ge F, Ke C, Tang W, Yang X, Tang C, Qin G, Xu R, Li T, Chen X, Zuo J, Ye Y (2007) Isolation of chlorogenic acids and their derivatives from Stemona japonica by preparative HPLC and evaluation of their anti-AIV (H5N1) activity in vitro. Phytochem Anal 18: 213-218   DOI
3 Han T, Li H, Zhang Q, Zheng H, Qin L (2006) New thiazinediones and other components from Xanthium strumarium. Chem Nat Comd 42: 567-570   DOI
4 Jang JH, Lee KH, Jung HK, Sim MO, Kim TM, Woo KW, An BK, Cho JH, Cho HW (2016) Anti-inflammatory effects of 6-O-acetyl mangiferin from Iris rossii Baker via NF-kb signal blocking in lipopolysaccharidestimulated RAW 264.7 cells. Chem Biol Interact 257: 54-60   DOI
5 Kim CS, Kim KH, Lee KR (2014) Phytochemical constituents of the leaves of Hosta longipes. Nat Prod Sci 20: 86-90
6 Kim JA, Jung BO, Chung SJ (2017) Antioxidant activity of water-soluble chitosan with Dicentra spectabilis. J Chitin Chitosan 22: 28-32   DOI
7 Lee HE, Kim JA, Whang WK (2017) Chemical constituents of Smilax china L. stems and their inhibitory activities against glycation, aldose reductase, $\alpha$-glucosidase, and lipase. Molecules 22: 451/1-451/18   DOI
8 Lee IK, Kim KH, Choi SU, Lee JH, Lee KR (2009) Phytochemical constituents of Thesuim chinensis TURCZ and their cytotoxic activities in vitro. Nat Prod Sci 15: 246-249
9 Lee KS, Sim OK, Shin JS, Choi YE, Kim EY (2004) Mass propagation of Dicentra spectabilis L. Lemaire through in vitro suspension culture. Korean J Plant Biotechnol 31: 121-126   DOI
10 Ma WG, Fukushi Y, Tahara S, Osawa T (2000) Fungitoxic alkaloids from Hokkaido Papaveraceae. Fitoterapia 71: 527-534   DOI
11 McNulty J, Poloczek J, Larichev V, Werstiuk NH, Griffin C, Pandey S (2007) Discovery of the apoptosis-inducing activity and high accumulation of the butenolides, menisdaurilide and aquilegiolide, in Dicentra spectabilis. Planta Med 73:1543-1547   DOI
12 Audran G, Mori K (1998) Synthesis of phyllanthurinolactone, the leaf-closing factor of Phyllanthus urinaria, and its three stereoisomers. Eur J Org Chem 1998: 57-62   DOI
13 Choi HS, Cho JY, Jin MR, Lee YG, Kim SJ, Ham KS, Moon JH (2016) Phenolics, acyl galactopyranosyl glycerol, and lignan amides from Tetragonia tetragonioides (Pall.) Kuntze. Food Sci Biotechnol 25: 1275-1281   DOI
14 Bradding P, Roberts JA, Britten KM, Montefort S, Djukanovic R, Mueller R, Heusser CH, Howarth PH, Holgate ST (1994) Interleukin-4, -5, and -6 and tumor necrosis factor-alpha in normal and asthmatic airways: Evidence for the human mast cell as a source of these cytokines. Am J Respir Cell Mol Biol 10: 471-480   DOI
15 Beutler B, Greenwald D, Hulmes JD, Chang M, Pan YC, Mathison J, Ulevitch R, Cerami A (1985) Identity of tumor necrosis factor and the macrophage-secreted factor cachectin. Nature 316: 552-554   DOI
16 Cha BC, Lee HE (2007) Antioxidant activities of flavonoids from the leaves of Smilax china Linne. Kor J Pharmacogn 38: 31-36
17 deRojas-Walker T, Tamir S, Ji H, Wishnok JS, Tannenbaum SR (1995) NO induces oxidative damage in addition to deamination in macrophage DNA. Chem Res Toxicol. 8: 473-477   DOI
18 Dinarello CA (1984) Interleukin-1 and the pathogenesis of acute phase response. N Engl J Med. 311: 1413-1418   DOI
19 Dunigan DD, Waters SB, Own TC (1995) Owen Aqueous Soluble Tetrazolium/Formazan MTS as an Indicator of NADH- and NADPHDependent Dehydrogenase Activity. Bio Techniques 19: 640-649
20 Ritchlin CT, Haas-Smith SA, Li P, Hicks DG, Schwarz EM (2003) Mechanisms of TNF-alpha- and RANKL-mediated osteoclastogenesis and bone resorption in psoriatic arthritis. J Clin Invest 111: 821-831   DOI
21 Seger C, Strum S, Strasser EM, Ellmerer E, Stuppner H (2004) $^1H$ and $^{13}C$ NMR signal assignment of benzylisoquiniline alkaloids from Fumaria officinalis L. (Papaveraceae). Magn Reson Chem 42: 882-886   DOI
22 Sim MO, Lee HJ, Jang JH, Lee HE, Jung HK, Kim TM, No JH, Junh JK, Jung DE, Cho HW (2017) Anti-inflammatory and antioxidant effects of Spiraea prunifolia Sieb. Et Zucc. var. simpliciflora Nakai in RAW 264.7 cells. Korean J. Plant Res 30:335-342
23 Seigler DS, Pauli GF, Frohlich R, Wegelius E, Nahrstedt A, Glander KE, Ebinger JE (2005) Cyanogenic glycosides and menisdaurin from Guazuma ulmifolia, Ostrya virginiana, Tiquilia plicata, and Tiquilia canescens. Phytochemistry 66: 1567-1580   DOI
24 Seo KH, Jung JW, Thi NN, Lee YH, Back NI (2016) Flavonoid glycosides from flowers of Pulsatilla koreana Nakai. Nat Prod Sci 22: 41-45   DOI
25 Serhan CN, Savill J (2005) Resolution of inflammation: the beginning programs the end. Nat Immunol 6: 1191-1197   DOI
26 Sim OK, Lee KS, Kim EY, Eun JS (2005) Formation of gametophytes and development of zygotic embryo in Dicentra spectabilis. Korean J Plant Res 18: 302-308
27 Tran TTT, Nguyen TY, Tran MH, Weon KY, Woo MH, Min BS (2014) Compounds from the aerial parts of Aceriphyllum rossii and their cytotoxic activity. Nat Prod Sci 20: 146-151
28 Medzhitov R, Janeway CA Jr (1997) Innate immunity: impact on the adaptive immune response. Curr Opin Immunol 9: 4-9   DOI
29 Woo KW, Lee KH, Jang JH, Kim MS, Cho HW, Cho JH, An B (2016) Antiinflammatory constituents from the aerial parts of Iris minutiaurea. Nat Prod Commun 11: 817-819