Antioxidant, anti-adipocyte differentiation, antitumor activity and anthelmintic activities against Anisakis simplex and Hymenolepis nana of yakuchinone A from Alpinia oxyphylla

BMC Complementary and Alternative Medicine

Chia-Hua Liang⁸  Hsiou-Yu Ding⁴  Leong-Perng Chan²  Hui-Chuan Wang⁴  Ting-Wei Huang⁵  Lin Wang⁶  Ya-Ping Tseng¹  Guey-Horng Wang⁸  Feng-Yu Chiang⁹  Tzung-Han Chou⁷  Chuan-Min Yen³  Rong-Jyh Lin³ 

[1]Institute of Basic Medical Sciences, National Cheng Kung University, Tainan,Taiwan

[2]Institute of Clinical Medicine, Kaohsiung Medical University, Kaohsiung,Taiwan

[3]Department of Parasitology, Faculty of Medicine, Kaohsiung Medical University,Kaohsiung, Taiwan

[4]Institute of Cosmetic Science, Chia Nan University of Pharmacy and Science,Tainan, Taiwan

[5]Department of Public Health, Kaohsiung Medical University, Kaohsiung, Taiwan

[6]Department of Medical Laboratory Science and Biotechnology, Kaohsiung MedicalUniversity, Kaohsiung, Taiwan

[7]Department of Chemical and Materials Engineering, National Yunlin University ofScience and Technology, Yunlin, Taiwan

[8]Department of Cosmetic Science, Chia Nan University of Pharmacy and Science,Tainan, Taiwan

[9]Department of Otolaryngology-Head and Neck Surgery, Kaohsiung Medical UniversityHospital, Kaohsiung Medical University, Kaohsiung, Taiwan

关键词: Anisakis simplex;    Hymenolepis nana;    Apoptosis;    Adipogenesis;    Antioxidant;    Yakuchinone A;   

Others  :  1220983
DOI  :  10.1186/1472-6882-13-237

 received in 2013-06-20, accepted in 2013-09-23,  发布年份 2013

【 摘 要 】

Background

Alpinia oxyphylla is a common remedy in traditional Chinese medicine. Yakuchinone A is a major constituent of A. oxyphylla and exhibits anti-inflammatory, antitumor, antibacterial, and gastric protective activities.

Methods

Antioxidant and antitumor characteristics of yakuchinone A in skin cancer cells as well as novel mechanisms for the inhibition of adipocyte differentiation, cestocidal activities against Hymenolepis nana adults, and nematocidal activities against Anisakis simplex larvae are investigated.

Results

Yakuchinone A presents the ability of the removal of DPPH·and ABTS⁺ free radicals and inhibition of lipid peroxidation. Yakuchinone A suppresses intracellular lipid accumulation during adipocyte differentiation in 3 T3-L1 cells and the expressions of leptin and peroxisome proliferator-activated receptor γ (PPARγ). Yakuchinone A induces apoptosis and inhibits cell proliferation in skin cancer cells. The inhibition of cell growth by yakuchinone A is more significant for non-melanoma skin cancer (NMSC) cells than for melanoma (A375 and B16) and noncancerous (HaCaT and BNLCL2) cells. Treatment BCC cells with yakuchinone A shows down-regulation of Bcl-2, up-regulation of Bax, and an increase in cleavage poly (ADP-ribose) polymerase (PARP). This suggests that yakuchinone A induces BCC cells apoptosis through the Bcl-2-mediated signaling pathway. The anthelmintic activities of yakuchinone A for A. simplex are better than for H. nana.

Conclusions

In this work, yakuchinone A exhibits antioxidative properties, anti-adipocyte differentiation, antitumor activity, and anthelmintic activities against A.simplex and H. nana.

【 授权许可】

   
2013 Lin et al.; licensee BioMed Central Ltd.

【 图 表 】

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【 参考文献 】

• [1]Jia J, Zhang X, Hu YS, Wu Y, Wang QZ, Li NN, Guo QC, Dong XC: Evaluation of in vivo antioxidant activities of Ganoderma lucidum polysaccharides in STZ-diabetic rats. Food Chem 2009, 115(1):32-36.
• [2]Alfadda AA, Sallam RM: Reactive oxygen species in health and disease. J Biomed Biotechnol 2012, 2012:936486.
• [3]Seo JB, Park SW, Choe SS, Jeong HW, Park JY, Choi EW, Seen DS, Jeong JY, Lee TG: Foenumoside B from Lysimachia foenum-graecum inhibits adipocyte differentiation and obesity induced by high-fat diet. Biochem Biophys Res Commun 2012, 417(2):800-806.
• [4]Hsu CL, Lin YJ, Ho CT, Yen GC: Inhibitory effects of garcinol and pterostilbene on cell proliferation and adipogenesis in 3T3-L1 cells. Food Funct 2012, 3(1):49-57.
• [5]Cho S, Choi Y, Park S, Park T: Carvacrol prevents diet-induced obesity by modulating gene expressions involved in adipogenesis and inflammation in mice fed with high-fat diet. J Nutr Biochem 2012, 23(2):192-201.
• [6]Lee YK, Lee WS, Hwang JT, Kwon DY, Surh YJ, Park OJ: Curcumin exerts antidifferentiation effect through AMPKalpha-PPAR-gamma in 3T3-L1 adipocytes and antiproliferatory effect through AMPKalpha-COX-2 in cancer cells. J Agric Food Chem 2009, 57(1):305-310.
• [7]Lee YS, Kim WS, Kim KH, Yoon MJ, Cho HJ, Shen Y, Ye JM, Lee CH, Oh WK, Kim CT, Hohnen-Behrens C, Gosby A, Kraegen EW, James DE, Kim JB: Berberine, a natural plant product, activates AMP-activated protein kinase with beneficial metabolic effects in diabetic and insulin-resistant states. Diabetes 2006, 55(8):2256-2264.
• [8]Zang M, Xu S, Maitland-Toolan KA, Zuccollo A, Hou X, Jiang B, Wierzbicki M, Verbeuren TJ, Cohen RA: Polyphenols stimulate AMP-activated protein kinase, lower lipids, and inhibit accelerated atherosclerosis in diabetic LDL receptor-deficient mice. Diabetes 2006, 55(8):2180-2191.
• [9]De S, Adhikari S, Tilak-Jain J, Menon VP, Devasagayam TP: Antioxidant activity of an aminothiazole compound: possible mechanisms. Chem Biol Interact 2008, 173(3):215-223.
• [10]Chitchang S, Piamjinda T, Yodmani B, Radomyos P: Relationship between severity of the symptom and the number of Hymenolepis nana after treatment. J Med Assoc Thai 1985, 68:423-426.
• [11]Smyth JD, McManus DP: The physiology and biochemistry of cestodes. Cambridge: Cambridge University Press; 1989.
• [12]Ito A: Basic and applied immunology in cestode infections: from hymenolepis to taenia and echinococcus. Int J Parasitol 1997, 27(10):1203-1211.
• [13]Shih HH, Ku CC, Wang CS: Anisakis simplex (Nematoda: Anisakidae) third-stage larval infections of marine cage cultured cobia, Rachycentron canadum L., in Taiwan. Vet Parasitol 2010, 171:277-285.
• [14]Karl H, Baumann F, Ostermeyer U, Kuhn T, Klimpel S: Anisakis simplex (s.s.) larvae in wild Alaska salmon: no indication of post-mortem migration from viscera into flesh. Dis Aquat Organ 2010, 94(3):201-209.
• [15]Takei H, Powell SZ: Intestinal anisakidosis (anisakiosis). Ann Diagn Pathol 2007, 11:350-352.
• [16]Gamboa PM, Asturias J, Martínez R, Antépara I, Jáuregui I, Urrutia I, Fernández J, Sanz ML: Diagnostic utility of components in allergy to Anisakis simplex. J Investig Allergol Clin Immunol 2012, 22(1):13-19.
• [17]Sakanari JA, McKerrow JH: Anisakiasis. Clin Microbiol Rev 1989, 2(3):278-284.
• [18]Lin RJ, Chen CY, Lee JD, Lu CM, Chung LY, Yen CM: Larvicidal Constituents of Zingiber officinale (Ginger) against Anisakis simplex. Planta Med 2010, 76:1852-1858.
• [19]An LJ, Guan S, Shi GF, Bao YM, Duan YL, Jiang B: Protocatechuic acid from Alpinia oxyphylla against MPP + -induced neurotoxicity in PC12 cells. Food Chem Toxicol 2006, 44(3):436-443.
• [20]Zhang ZJ, Cheang LC, Wang MW, Li GH, Chu IK, Lin ZX, Lee SM: Ethanolic extract of fructus Alpinia oxyphylla protects against 6-hydroxydopamine-induced damage of PC12 cells in vitro and dopaminergic neurons in zebrafish. Cell Mol Neurobiol 2012, 32(1):27-40.
• [21]Jang S, Jung JC, Oh S: Synthesis of 1,3-diphenyl-2-propen-1-one derivatives and evaluation of their biological activities. Bioorg Med Chem 2007, 15(12):4098-4105.
• [22]Flynn DL, Rafferty MF, Boctor AM: Inhibition of 5-hydroxy-eicosatetraenoic acid (5-HETE) formation in intact human neutrophils by naturally-occurring diarylheptanoids: inhibitory activities of curcuminoids and yakuchinones. Prostaglandins Leukot Med 1986, 22(3):357-360.
• [23]Surh Y: Molecular mechanisms of chemopreventive effects of selected dietary and medicinal phenolic substances. Mutat Res 1999, 428(1–2):305-327.
• [24]Chun KS, Sohn Y, Kim HS, Kim OH, Park KK, Lee JM, Moon A, Lee SS, Surh YJ: Anti-tumor promoting potential of naturally occurring diarylheptanoids structurally related to curcumin. Mutat Res 1999, 428(1–2):49-57.
• [25]Zhang Q, Luo S, Wang H, Fun D: Studies on the chemical constituents of Yizhiren (Alpinia oxyphylla). Zhong Cao Yao 1997, 28:131-133.
• [26]Liang CH, Chan LP, Ding HY, So EC, Lin RJ, Wang HM, Chen YG, Chou TH: Free radical scavenging activity of 4-(3,4-dihydroxybenzoyloxymethyl)phenyl-O-β-D-glucopyranoside from Origanum vulgare and its protection against oxidative damage. J Agric Food Chem 2012, 60(31):7690-7696.
• [27]Chou TH, Ding HY, Lin RJ, Liang JY, Liang CH: Inhibition of melanogenesis and oxidation by protocatechuic acid from Origanum vulgare (oregano). J Nat Prod 2010, 73(11):1767-1774.
• [28]Thounaojam MC, Jadeja RN, Ramani UV, Devkar RV, Ramachandran AV: Sida rhomboidea. Roxb leaf extract down-regulates expression of PPARγ2 and leptin genes in high fat diet fed C57BL/6J mice and retards in vitro 3T3L1 pre-adipocyte differentiation. Int J Mol Sci 2011, 12(7):4661-4677.
• [29]Naowaboot J, Chung CH, Pannangpetch P, Choi R, Kim BH, Lee MY, Kukongviriyapan U: Mulberry leaf extract increases adiponectin in murine 3T3-L1 adipocytes. Nutr Res 2011, 32(1):39-44.
• [30]Chou TH, Liang CH: The molecular effects of aloe-emodin (AE)/liposome-AE on human nonmelanoma skin cancer cells and skin permeation. Chem Res Toxicol 2009, 22(12):2017-2028.
• [31]Kundu S, Roy S, Lyndem LM: Cassia alata L: potential role as anthelmintic agent against Hymenolepis diminuta. Parasitol Res 2012, 111(3):1187-1192.
• [32]Iglesias L, Valero A, Benitez R, Adroher FJ: In vitro cultivation of Anisakis simplex: pepsin increases survival and moulting from fourth larval to adult stage. Parasitology 2001, 123:285-291.
• [33]Kiuchi F, Miyashita N, Tsuda Y, Kondo K, Yoshimura H: Studies on crude drugs effective on visceral larva migrans. I. Identification of larvicidal principles in betel nuts. Chem Pharm Bull 1987, 35:2880-2886.
• [34]Đorđević TM, Šiler-Marinković SS, Dimitrijević-Branković SI: Effect of fermentation on antioxidant properties of some cereals and pseudo cereals. Food Chem 2010, 119:957-963.
• [35]Chou TH, Ding HY, Chan LP, Liang JY, Liang CH: Novel phenolic glucoside, origanoside, protects against oxidative damage and modulates antioxidant enzyme activity. Food Res Int 2011, 44:1496-1503.
• [36]Wu SJ, Ng LT: Antioxidant and free radical scavenging activities of wild bitter melon (Monordica charantia Linn. Var. abbreviate Ser.) in Taiwan. LWT 2008, 41:323-330.
• [37]Zou Y, Lu Y, Wei D: Antioxidant activity of a flavonoid-rich extract of Hypericum perforatum L. in vitro. J Agric Food Chem 2004, 52(16):5032-5039.
• [38]Lee MH, Chen YY, Tsai JW, Wang SC, Watanabe T, Tsai YC: Inhibitory effect of β-asarone, a component of Acorus calamus essential oil, on inhibition of adipogenesis in 3T3-L1 cells. Food Chem 2011, 126:1-7.
• [39]Chun KS, Kang JY, Kim OH, Kang H, Surh YJ: Effects of yakuchinone A and yakuchinone B on the phorbol ester-induced expression of COX-2 and iNOS and activation of NF-kappaB in mouse skin. J Environ Pathol Toxicol Oncol 2002, 21(2):131-139.
• [40]Liang CH, Wang GH, Chou TH, Wang SH, Lin RJ, Chan LP, So EC, Sheu JH: 5-epi-Sinuleptolide induces cell cycle arrest and apoptosis through tumor necrosis factor/mitochondria-mediated caspase signaling pathway in human skin cancer cells. Biochim Biophys Acta 2012, 1820(7):1149-1157.