Glycosyl flavones from Humulus japonicus suppress MMP-1 production via decreasing oxidative stress in UVB irradiated human dermal fibroblasts
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초록
Exposure to Ultraviolet (UV) light induces photoaging of skin, leading to wrinkles and sunburn. The perennial herb Humulus japonicus, widely distributed in Asia, is known to have antiinflammatory, antimicrobial, and antioxidant effects. However, the physiological activities of isolated compounds from H. japonicus have rarely been investigated. This study focused on the isolation of active compounds from H. japonicus and the evaluation of their effects on photoaging in UVB-irradiated human fibroblast (Hs68) cells. When the extract and four fractions of H. japonicus were treated respectively in UVB-irradiated Hs68 cells to investigate anti-photoaging effects, the ethyl acetate (EtOAc) fraction showed the strongest inhibitory effect on MMP- 1 secretion. From EtOAc fraction, we isolated luteolin-8-C-glucoside (1), apigenin-8-C-glucoside (2), and luteolin-7-O-glucoside (3). These compounds suppressed UVB-induced MMP-1 production by inhibiting the phosphorylation of the mitogen-activated protein kinases (MAPKs) and activator protein-1 (AP-1). When the antioxidant activity of the compounds were estimated by conducting western blot, calculating the bond dissociation energies of the O-H bond (BDE) at different grade, and measuring radical scavenging activity, we found luteolin-8-C-glucoside (1) showed the strongest activity on the suppression of UVB-induced photoaging. These results demonstrate the inhibitory effect of three flavone glycosides derived from H. japonicus on MMP-1 production, MAPK and AP-1 signaling, and oxidative stress; this could prove useful in suppressing UVB induced photoaging.
Abstract
Exposure to Ultraviolet (UV) light induces photoaging of skin, leading to wrinkles and sunburn. The perennial herb Humulus japonicus, widely distributed in Asia, is known to have antiinflammatory, antimicrobial, and antioxidant effects. However, the physiological activities of isolated compounds from H. japonicus have rarely been investigated. This study focused on the isolation of active compounds from H. japonicus and the evaluation of their effects on photoaging in UVB-irradiated human fibroblast (Hs68) cells. When the extract and four fractions of H. japonicus were treated respectively in UVB-irradiated Hs68 cells to investigate anti-photoaging effects, the ethyl acetate (EtOAc) fraction showed the strongest inhibitory effect on MMP- 1 secretion. From EtOAc fraction, we isolated luteolin-8-C-glucoside (1), apigenin-8-C-glucoside (2), and luteolin-7-O-glucoside (3). These compounds suppressed UVB-induced MMP-1 production by inhibiting the phosphorylation of the mitogen-activated protein kinases (MAPKs) and activator protein-1 (AP-1). When the antioxidant activity of the compounds were estimated by conducting western blot, calculating the bond dissociation energies of the O-H bond (BDE) at different grade, and measuring radical scavenging activity, we found luteolin-8-C-glucoside (1) showed the strongest activity on the suppression of UVB-induced photoaging. These results demonstrate the inhibitory effect of three flavone glycosides derived from H. japonicus on MMP-1 production, MAPK and AP-1 signaling, and oxidative stress; this could prove useful in suppressing UVB induced photoaging.
참고문헌 (27)
- Bosch R, "Mechanisms of photoaging and cutaneous photocarcinogenesis, and photoprotective strategies with phytochemicals", Antioxidants (Basel), 4, pp.248~268 (2015)
- Fisher GJ, "Pathophysiology of premature skin aging induced by ultraviolet light", N Engl J Med, 337, pp.1419~1428 (1997)
- Jenkins G, "Molecular mechanisms of skin ageing", Mech Ageing Dev, 123, pp.801~810 (2002)
- Narayanan DL, "Ultraviolet radiation and skin cancer", Int J Dermatol, 49, pp.978~986 (2010)
- Quan T, "Matrix-degrading metalloproteinases in photoaging", J Investig Dermatol Symp Proc, 14, pp.20~24 (2009)
- Fisher GJ, "Molecular mechanisms of photoaging and its prevention by retinoic acid : ultraviolet irradiation induces MAP kinase signal transduction cascades that induce Ap-1-regulated matrix metalloproteinases that degrade human skin in vivo", J Investig Dermatol Symp Proc, 3, pp.61~68 (1998)
- Naya Y, "Constituents of Hops. 5. volatile composition of humulus-japonicus sieb et zucc", Bull Chem Soc Jpn, 43, pp.3594~3596 (1970)
- 황순이, "葎草 추출물이 Rat의 paw edema에 미치는 영향", 한방안이비인후피부과학회지, 22(3), pp.71~79 (2009), 대한한방안이비인후피부과학회
- 이연리, "환삼덩굴 메탄올추출물의 In Vitro 항산화 및 항암 활성", 한국식품영양학회지, 25(2), pp.357~361 (2012), 한국식품영양학회
- Sung B, "Humulus japonicus extract exhibits antioxidative and anti-aging effects via modulation of the AMPK-SIRT1 pathway", Exp Ther Med, 9, pp.1819~1826 (2015)
- 이강로, "Norsesquiterpene and Steroid Constituents of Humulus japonicus", Natural Product Sciences, 13(4), pp.332~336 (2007), 한국생약학회
- Byung Chul Yu, "Two New Phenolic Constituents of Humulus japonicus and their Cytotoxicity Test In Vitro", Archives of Pharmacal Research, 30(11), pp.1471~1475 (2007), 대한약학회
- Kim JE, "Epigallocatechin-3-gallate prevents heat shock-induced MMP-1 expression by inhibiting AP-1 activity in human dermal fibroblasts", Arch Dermatol Res, 305, pp.595~602 (2013)
- Amic D, "Reliability of bond dissociation enthalpy calculated by the PM6 method and experimental TEAC values in antiradical QSAR of flavonoids", Bioorg Med Chem, 18, pp.28~35 (2010)
- Amic D, "PM6 study of free radical scavenging mechanisms of flavonoids: why does O-H bond dissociation enthalpy effectively represent free radical scavenging activity?", J Mol Model, 19, pp.2593~2603 (2013)
- Zhang HY, "Substituent effects on O--H bond dissociation enthalpies and ionization potentials of catechols : a DFT study and its implications in the rational design of phenolic antioxidants and elucidation of structure-activity relationships for flavonoid antioxidants", Chemistry, 9, pp.502~508 (2003)
- "Cancer Facts & Figures 2019"[URL]
- 심관섭, "Structure Activity Relationship of Antioxidative Property of Flavonoids and Inhibitory Effect on Matrix Metalloproteinase Activity in UVA-Irradiated Human Dermal Fibroblast", Archives of Pharmacal Research, 30(3), pp.290~298 (2007), 대한약학회
- Rittie L, "UV-light-induced signal cascades and skin aging", Ageing Res Rev, 1, pp.705~720 (2002)
- Benavente-Garcıa O, "Antioxidant activity of phenolics extracted from Olea europaea L. leaves", Food Chem, 68, pp.457~462 (2000)
- Perveen S, "Antioxidant and urease inhibitory C-glycosylflavonoids from Celtis africana", J Asian Nat Prod Res, 13, pp.799~804 (2011)
- Praveena R, "Antioxidant potential of orientin : A combined experimental and DFT approach", J Mol Struct, 1061, pp.114~123 (2014)
- Praveena R, "Experimental and DFT studies on the antioxidant activity of a C-glycoside from Rhynchosia capitata", Spectrochim Acta A Mol Biomol Spectrosc, 103, pp.442~452 (2013)
- Wang Y, "PubChem : a public information system for analyzing bioactivities of small molecules", Nucleic Acids Res, 37, pp.W623~W633 (2009)
- O'Boyle NM, "Open Babel : An open chemical toolbox", J Cheminform, 3, pp.1~ (2011)
- Stewart JJ, "Optimization of parameters for semiempirical methods VI : more modifications to the NDDO approximations and re-optimization of parameters", J Mol Model, 19, pp.1~32 (2013)
- Brand-Williams W, "Use of a free-radical method to evaluate antioxidant activity", Food Sci Technol-Leb, 28, pp.25~30 (1995)