Natural products triggering biological targets-A review of the anti-inflammatory phytochemicals targeting the arachidonic acid pathway in allergy asthma and rheumatoid arthritis

Current Drug Targets

Volumn 12, Issue 3, 2011, Pages 288-301

  Chen, Sophie ^a  

^a UNIVERSITY OF SURREY   (United Kingdom)

Author keywords

Anti inflammation; Cyclooxygenase; Lipoxygenase; Nuclear factor kappa b; Phospholipase a2; Phytochemicals; Tumor necrosis factor

Indexed keywords

ANTIINFLAMMATORY AGENT; APIGENIN; ARACHIDONATE 12 LIPOXYGENASE; ARACHIDONATE 15 LIPOXYGENASE; ARACHIDONATE 2 LIPOXYGENASE; ARACHIDONATE 5 LIPOXYGENASE; ARACHIDONIC ACID; BAICALEIN; COLCHICINE; COUMARIN DERIVATIVE; CYCLOOXYGENASE 1; CYCLOOXYGENASE 1 INHIBITOR; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITOR; FISETIN; FLAVONOID; GALANGIN; INTERLEUKIN 13; INTERLEUKIN 4; INTERLEUKIN 6; LIPOXYGENASE; LIPOXYGENASE INHIBITOR; NATURAL PRODUCT; PHOSPHOLIPASE A2; PHOSPHOLIPASE A2 INHIBITOR; PLANT MEDICINAL PRODUCT; POLYPHENOL; TERPENOID; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ALLERGIC ASTHMA; ANTIINFLAMMATORY ACTIVITY; ARTICLE; HISTAMINE RELEASE; HUMAN; IC 50; IMMUNOMODULATION; MUCUS; NONHUMAN; RETICULOCYTE; RHEUMATOID ARTHRITIS; TH1 CELL; TH2 CELL;

EID: 79551646077     PISSN: 13894501     EISSN: None     Source Type: Journal    
DOI: 10.2174/138945011794815347     Document Type: Article

References (172)

1. Toratora GJ, Grabowski SR. In: Principles of anatomy and physiology, 8th ed. Harper Collins College 1996; pp. 684-685.
2. Leirisalo-Repo M. The present knowledge of the inflammatory process and the inflammatory mediators. Pharmacol Toxicol 1994; 75(Suppl 2): 1-3.
3. Tak PP, Firestein GS. NF-κB: a key role in inflammatory diseases. J Clin Invest 2001; 107: 7-11.
4. Fujisawa K, Aono H, Hasunuma T, Yamamoto K, Mita S, Mishioka K. Activation of transcription factor NF-κB in human synovial cells in response to tumor necrosis factor. Arthritis Rheum 1996; 39: 197-203.
5. Nam NH. Natur ally occurring NF-κB inhibitors. Mini Rev Med Chem 2006; 6: 945-951.
6. Gagliardo R, Chanez P, Mathieu M, et al. Persistent activation of NF-κB signaling pathway in severe uncontrolled asthma. Am J Respir Crit Care Med 2003; 168: 1190-1198.
7. Lee KM, Kang BS, Lee HL, et al. Spinal NF-κB activation induces COX-2 upregulation and contributes to inflammatory pain hypersensitivity. Eur J Neurosci 2004; 19: 3375-3381.
8. Brennan FM, McInnes JB. Evidence that cytokines play a role in rheumatoid arthritis. J Clin Investig 2008; 118: 3537-3545.
9. Murakami M, Kudo I. Phospholipase A2. J Biochem 2002; 131: 285-292.
10. Funk CD. Prostaglandins and leukotrienes: advances in eicosanoid biology. Science 2001; 294: 1871-1875.
11. Hi T, Bishop-Bailey D, Liu CH, Schaefers HJ, Trifan OC. Minireview Cyclooxygenase-1 and -2 isoenzymes. Int J Biochem Cell Biol 1999; 31: 551-557.
12. Kim DC, Hsu FI, Barrett NA, et al. Cysteinyl leukotrienes regulate Th2 inflammation cell-dependent pulmonary. J Immunol 2006; 76: 4440-4448.
13. Miyashita T, Kawakami A, Tamai M, et al. Akt is an endogenous inhibitor toward tumor necrosis factor-related apoptosis inducing ligand-mediated apoptosis in rheumatoid synovial cells. Biochem Biophys Res Commun 2003; 312: 397-404.
14. Krause A, Scaletta N, Ji JD, Ivashkiv LB. Rheumatoid arthritis synoviocyte survival is dependent on stat 3. J Immunol 2002; 169: 6610-6616.
15. Feldmann M, Brennan FM, Maini RN. Rheumatoid arthritis. Cell 1996; 85: 307-310.
16. Bartok B, Firestein GS. Fibroblast-like synoviocytes: key effector cells in rheumatoid arthritis. Immunol Rev 2010; 233: 233-255.
17. Abbas AK, Murphy KM, Sher A. Functional diversity of helper T lymphocytes. Nature 1996; 383: 787-793.
18. Quayle AJ, Chomarat P, Miossec P, Kjeldsen-Kragh J, Førre O, Natvig JB. Rheumatoid inflammatory T-cell clones express mostly Th1 but also Th2 and mixed (Th0-like) cytokine patterns. Scand J Immunol 1993; 38: 75-82.
19. Miossec P, van den Berg W. Th1/Th2 cytokine balance in arthritis. Arthritis Rheum 1997; 40: 2105-2115.
20. Barnes PJ. Th2 cytokines and asthma: an introduction. Respir Res 2001; 2: 64-65.
21. Feldmann M, Brennan FM, Maini RN. Role of cytokines in rheumatoid arthritis. Annu Rev Immunol 1996; 14: 397-440.
22. Rosenberg HF, Phipps S, Foster PS. Eosinophil trafficking in allergy and asthma. J Allergy Clin Immunol 2007; 119: 1303-1310.
23. Hallett MB, Williams AS. Stopping the traffic: a route to arthritis therapy. Eur J Immunol 2008; 38: 2650-2653.
24. Falus A, Meterey K. Histamine: an early messenger in inflammatory and immune reactions. Immunol Today 1990; 13: 154-156.
25. Lee CJ, Lee JH, Seok JH, et al. Effects of baicalein, berberine, curcumin and hesperidin on mucin release from airway goblet cells. Planta Med 2003; 69: 523-5256.
26. Chen HJ, Shih CK, Hsu HY, Chiang W. Mast cell-dependent allergic responses are inhibited by ethanolic extract of Adlay (Coix lachryma-jobi L. var. ma-yuen Stapf) Testa. J Agric Food Chem 2010; 58: 2596-2601.
27. Vane JR, Botting RM. Mechanism of action of anti-inflammatory drugs. Scand J Rheum 1996; 25: 9-21.
28. Cashman JN. The mechanisms of action of NSAIDs in analgesia. Drugs 1996; 52(Suppl 5): 13-23.
29. Rang HP, Dale MM. Local Harmones, Inflammation and Allergy. In: Pharmacology. 2nd ed. Churchill Livingstone ELBS. 1999; pp. 243-279.
30. Charlier C, Michaux C. Dual inhibition of cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX) as a new strategy to provide safer non-steroidal anti-inflammatory drugs. Eur J Med Chem 2003; 29: 645-659.
31. Izuhara K, Ohta S, Shiraishi H, et al. The mechanism of mucus production in bronchial asthma. Curr Med Chem 2009; 16: 2867-7285.
32. Yedgar S, Lichtenberg D, Schnitzer E. Inhibition of phospholipase A2 as a therapeutic target. Biochem Biophys Acta 2000; 1488: 182-187.
33. Romano A, Freudenthal R, Merlo E, Routtenberg A. Evolutionarily-conserved role of the NF-κB transcription factor in neural plasticity and memory. Eur J Neurosci 2006; 24: 1507-1516.
34. Haridas V, Arntzen CJ, Gutterman JU. Avicins, a family of triterpenoid saponins from Acacia victoriae (Bentham), inhibit activation of nuclear factor-κB by inhibiting both its nuclear localization and ability to bind DNA. Proc Natl Acad Sci USA 2001; 98: 11557-11562.
35. Yamaza T, Masuda KF, Tsukiyama Y, et al. NF-{kappa}B activation and iNOS expression in the synovial membrane of rat temporomandibular joints after induced synovitis. J Dent Res 2003; 82: 183-188.
36. Levy BD, Clish CB, Schmidt B, Gronert K, Serhan CN. Lipid mediator class switching during acute inflammation: signals in resolution. Nat Immunol 2001; 2: 612-619.
37. Ruminy P, Gangneux C, Claeyssens S, ScottelM, Daveau M, Salier JP. Gene transcription in hepatocytes during the acute phase of a systemic inflammation: from transcription factors to target genes. Inflamm Res 2000; 50: 383-390.
38. Bainbridge J, Madden L, Binks M, Malhotra R, Paleolog E. NOS inhibition as a target in arthritis, inflammation and angiogenesis. Vas Pharm 2006; 45: 10-14.
39. Bongartz T, Sutton AJ, Sweeting MJ, Buchan I, Matteson EL, Montori V. Anti-TNF antibody therapy in rheumatoid arthritis and the risk of serious infections and malignancies. Systematic review and meta-analysis of rare harmful effects in randomized controlled trials. JAMA 2006; 295: 2275-2285.
40. Marjanovic N, Dave M, Park J, et al. Prostaglandin e2 dissociates nuclear trafficking of individual nf-{kappa}b subunits (p65, p50) in stimulated rheumatoid synovial fibroblasts. J Immunol 2005; 175:6924-6930.
41. Courtois G. The N F-B signaling pathway in human genetic diseases. Cell Mol Life Sci 2005; 62: 1682-1691.
42. Willard T. Textbook of advanced hebology Wild Rose College of natual healing, Ltd 1992; pp. 159-314.
43. Lättig J, Böhl M, Fischer P, et al. Mechanism of inhibition of human secretory phospholipase A2 by flavonoids: rationale for lead design. J Comput Aided Mol Des 2007; 21: 473-483.
44. Thwin MM, Douni E, Arjunan P, Kollias G, Kumar PV, Gopalakrishnakone P. Suppressive effect of secretory phospholipase A2 inhibitory peptide on interleukin-1β-induced matrix metalloproteinase production in rheumatoid synovial fibroblasts, and its antiarthritic activity in hTNFtg mice. Arthritis Res Ther 2009; 11: R138.
45. Singh N, Jabeen T, Pal A, et al. Crystal structures of the complexes of a group IIA phospholipase A2 with two natural antiinflammatory agents, anisic acid, and atropine reveal a similar mode of binding. Proteins 2006; 64: 89-100.
46. Gil B, Sanz MJ, Terencio MC, Gunasegaran R, Payá M, Alcaraz MJ. Morelloflavone, a novel biflavonoid inhibitor of human secretory phospholipase A2 with anti-inflammatory activity. Biochem Pharmacol 1997; 53: 733-740.
47. Rosenthal MD, Vishwanath BS, Franson RC. Effects of aristolochic acid on phospholipase A2 activity and arachidonate metabolism of human neutrophils. Biochem Biophys Acta 1989; 1001: 1-8.
48. Penzo D, Petronilli V, Angelin A, et al. Arachidonic acid released by phospholipase A2 activation triggers Ca2+-dependent apoptosis through the mitochondrial pathway. J Biol Chem 2004; 279: 25219-2525.
49. Yamaguchi S, Kawamura T, Noro Y, Tanaka T. Berberine contents in phellodendron leaves. Nat Med 1998; 52: 452-424.
50. Nirmal N, Praba GO, Velmurugan D. Modeling studies on phospholipase A2-inhibitor complexes. Indian J Biochem Biophys 2008; 45: 256-262.
51. Sohn HY, Son KH, Kwon CS, Kwon GS, Kang SS. Antimicrobial and cytotoxic activity of 18 prenylated flavonoids isolated from medicinal plants: Morus alba L., Morus mongolica Schneider, Broussnetia papyrifera (L.) Vent, Sophora flavescens Ait and Echinosophora koreensis Nakai. Phytomedicine 2004; 11: 666-672.
52. Monti MC, Chini MG, Margarucci L, et al. The molecular mechanism of human group IIA phospholipase A2 inactivation by bolinaquinone. J Mol Recognit 2009; 22: 530-537.
53. Calixto JB, Otuki MF, Santos ARS. Antiinflammtory compounds of plant origin. Part 1. Action on arachidonin acid pathway, nitric oxide and nuclear factor κB (NF-κB). Planta Med 2003; 69: 973-983.
54. Jain MK, Yu B, Rogers JM, et al. Acidic triterpenoids have emerged as a new class of PLA2 inhibitors. Phytochemistry 1995; 39: 537-547.
55. Ammon HP. Boswellic acids in chronic inflammatory diseases. Planta Med 2006; 72: 1100-1116.
56. Sciorb T, Didierc B, Hibertb M, Berthon JY. Ethnopharmacology and bioinformatic combination for leads discovery: application to phospholipase A2 inhibitors. Phytochemistry 2001; 58: 865-874.
57. Okimasu E, Moromizato Y, Watanabe S, et al. Inhibition of phospholipase A2 and platelet aggregation by glycyrrhizin, an antiinflammation drug. Acta Med Okayama 1983; 37: 385-391.
58. Shimoyama Y, Sakamoto R, Akaboshi T, Tanaka M, Ohtsuki K. Characterization of secretory type IIA phospholipase A2 (sPLA2-IIA) as a glycyrrhizin (GL)-binding protein and the GL-induced inhibition of the CK-II-mediated stimulation of sPLA2-IIA activity in vitro. Biol Pharm Bull 2001; 24: 1004-1008.
59. Honda T, Gribble GW, Suh N, et al. Novel synthetic oleanane and ursane triterpenoids with various enone functionalities in ring A as inhibitors of flavonoids with modified rings A and C: a series of highly active inhibitors of nitric oxide production in mouse macrophages. J Med Chem 2000; 43: 4233-46.
60. Subbaramaiah K, Michaluart P, Sporn MB, Dannenberg AJ. Ursolic acid inhibits cyclooxygenase-2 transcription in human mammary epithelial cells. Cancer Res 2000; 60: 2399-2404.
61. Lee CJ, Seok JH, Hur GM, et al. Effects of ursolic acid betulin and sulphur containing compounds on mucin release from airway goblet cells. Planta Med 2004; 70: 1119-11122.
62. Bang JS, Oh da H, Choi HM, et al. Anti-inflammatory and antiarthritic effects of piperine in human interleukin 1betastimulated fibroblast-like synoviocytes and in rat arthritis models. Arthritis Res Ther 2009; 11: R49.
63. Danz H, Stoyanova S, Thomet OA, et al. Inhibitory activity of tryptanthrin on prostaglandin and leukotriene synthesis. Planta Med 2002; 68: 875-880.
64. Liao YH, Houghton PJ, Hoult JRS. Novel and known constituents from buddleja species and their activity against leukocyte eicosanoid generation. J Nat Prod 1999; 62: 1241-1245.
65. Lee JH, Zhou HY, Cho SY, Kim YS, Lee YS, Jeong CS. Antiinflammatory mechanisms of apigenin: inhibition of cyclooxygenase-2 expression, adhesion of monocytes to human umbilical vein endothelial cells, and expression of cellular adhesion molecules. Arch Pharm Res 2007; 30: 1318-1327.
66. Miguel López-Lázaro. Distribution and biological activities of the flavonoid luteolin, mini-review. Med Chem 2009; 9: 31-59.
67. Reddy GR, Ueda N, Hada T, et al. A prenylflavone, artonin E, as arachidonate 5-lipoxygenase inhibitor. Biochem Pharmacol 1991; 41: 115-118.
68. Jia Q. Generating and screening a natural product library for cyclooxygenase and lipoxyenase dual inhibitors. Studies Nat Products Chem 2003; 29: 643-718.
69. Kim HP, Son KH, Chang HW, Kang SS. Antiinflammaory plant flavonoids and cellular action mechanism. J Pharmacol Sci 2004; 96: 229-245.
70. Bai HW, Zhu BT. Strong activation of cyclooxygenase I and II catalytic activity by dietary bioflavonoids. J Lipid Res 2008; 49: 26557-26570.
71. Chen S, Gao J, Halicka HD, Huang X, Traganos F, Darzynkiewicz Z. Down-regulation 470 of androgen-receptor and PSA by phytochemicals. Int J Oncol 2008; 32: 405-11.
72. Chi YS, Jong HG, Son KH, Chang HW, Kang SS, Kim HP. Effects of naturally occurring prenylated flavonoids on enzymes metabolizing arachidonic acid: cyclooxygenases and lipoxygenases. Bioch Pharm 2001; 62: 1185-1191.
73. Hong CH, Hur SK, Oh OJ, Kim SS, Nam KA, Le SK. Evaluation of natural products on inhibition of inducible cyclooxygenase (COX-2) and nitric oxide synthase (iNOS) in cultured mouse macrophage cells. J Ethnopharm 2002; 83: 153-159.
74. Swami S, Krishnan AV, Moreno C, Bhattacharyya RB, Peehl DM, Feldman D. Calcitriol and genistein actions to inhibit the prostaglandin pathway: potential combination therapy to treat prostate cancer. J Nutr 2007; 137: 205S-210S.
75. Crescente M, Jessen G, Momi S, et al. Interactions of gallic acid, resveratrol, quercetin and aspirin at the platelet cyclooxygenase-1 level - Functional and modelling studies. Thromb Haemost 2009; 102: 336-346.
76. Kim DW, Chi YS, Son KH, et al. Effects of sophoraflavanone G, a prenylated flavonoid from Sophora flavescens, on cyclooxygenase-2 and in vivo inflammatory response. Arch Pharm Res 2002; 25: 329-335.
77. Koeberle A, Bauer J, Verhoff M, Hoffmann M, Northoff H, Werz O. Green tea epigallocatechin-3-gallate inhibits microsomal prostaglandin E(2) synthase-1. Biochem Biophys Res Commun 2009; 8: 350-354.
78. Park IJ, Lee YK, Hwang JT, Kwon DY, Ha J, Park OJ. Green tea catechin controls apoptosis in colon cancer cells by attenuation of H2O2-stimulated COX-2 expression via the AMPK signaling pathway at low-dose H2O2. Ann N Y Acad Sci 2009; 1171: 538-544.
79. Adhikari DP, Francis JA, Schutzki RE, Chandra A, Nair MG. Quantification and characterisation of cyclo-oxygenase and lipid peroxidation inhibitory anthocyanins in fruits of Amelanchier. Phytochem Anal 2005; 16: 175-180.
80. Koeberle A, Northoff H, Werz O. Curcumin blocks prostaglandin E2 biosynthesis through direct inhibition of the microsomal prostaglandin E2 synthase-1. Mol Cancer Ther 2009; 8: 2348-2355.
81. Raghavendra RH, Naidu KA. Spice active principles as the inhibitors of human platelet aggregation and thromboxane biosynthesis. Prostaglandins Leukot Essent Fatty Acids 2009; 81: 73-8.
82. Likhitwitayawoid K, Sawasdee K, Kirtikara K. Flavonoids and stilbenoids with COX-1 and COX-2 inhibitory activity from Drrcaena loureiri. Planta Med 2002; 68: 841-843.
83. Burnett BP, Jia Q, Zho Y, Levy RM. A medical extract of Scutellaria baicalensis and ACAcia catechu acts a dual inhibition of cycloxygenase and 5-lipoxygenase to reduce inflammation. J Medicinal Food 2007; 10: 442-451.
84. Takada Y, Aggarwal BB. Betulinic acid suppresses metalloprotease- 9, cyclooxygenase-2 and matrix phosphorylation: abrogation of I{kappa}B{alpha} kinase and p65 activation through inhibition of carcinogen-induced NF-{kappa}B. J Immunol 2003; 171: 3278-3286.
85. Sethi G, Ahn KS, Pandey MK, Aggarwal BB. Celastrol, a novel triterpene, potentiates TNF-induced apoptosis and suppresses invasion of tumor cells by inhibiting NF-κB-regulated gene products and TAK1-mediated NF-κB activation. Blood 2007; 109: 2727-2735.
86. Kim SS, Oh OJ, Min HY, et al. Eugenol suppresses cyclooxygenase-2 expression in lipopolysaccharide-stimulated mouse macrophage RAW264.7 cells. Life Sci 2003; 73: 337-348.
87. Wang X, Chen Y, Han QB, et al. Proteomic identification of molecular targets of gambogic acid: role of stathmin in hepatocellular carcinoma. Proteomics 2009; 9: 242-253.
88. Li Q, Cheng H, Zhu G, et al. Gambogenic acid inhibits proliferation of A549 cells through apoptosis-inducing and cell cycle arresting. Biol Pharm Bull 2010, 33: 415-420.
89. Chen W, Shen YD, Zhao GS, Yao HP. Inhibitory effect of sinomenine on expression of cyclooxygenase-2 in lipopolysaccharide-induced PC-12 cells. Zhongguo Zhong Yao Za Zhi 2004; 29: 900-903.
90. Liu Q, Chen T, Chen G, et al. Triptolide impairs dendritic cell migration by inhibiting CCR7 and COX-2 expression through PI3K/Akt and NF-kB pathways. Mol Immunol 2007; 44: 2686-2696.
91. Yang CW, Chuang TH, Wu PL, Huang WH, Lee SJ. Anti-inflammatory effects of 7-methoxycryptopleurine and structure-activity relations of phenanthroindolizidines and phenanthroquinolizidines. Bioch Biophys Res Commun 2007; 354: 942-948.
92. Smolinski AT, Pestka JJ. Modulation of lipopolysaccharideinduced proinflammatory cytokine production in vitro and in vivo by the herbal constituents apigenin (chamomile), ginsenoside Rb1 (ginseng) and parthenolide (feverfew). Food Chem Toxicol 2003; 41: 1381-1390.
93. Woo KJ, Lim JH, Suh S, et al. Differential inhibitory effects of baicalein and baicalin on LPS-induced cyclooxygenase-2 expression through inhibition of C/EBPβ DNA-binding activity. Immunobiology 2006; 211: 359-368.
94. Błach-Olszewska Z, Lamer-Zarawska E. Come Back to Root-Therapeutic activities of scutellaria baicalensis root in aspect of innate immunity regulation-Part I. Adv Clin Exp Med 2008; 173:337-435.
95. Yamaki K, Kim DH, Ryu N, Kim YP, Kim SC, Ohuchi K. Effects of naturally occurring isoflavones on prostaglandin E2 production. Planta Med 2002; 68: 97-100.
96. Hermenegildo C, Oviedo PJ, García-Pérez MA,Tarín JJ, Cano A. Effects of phytoestrogens genistein and daidzein on prostacyclin production by human endothelial cells. JPET 2005; 315: 722-728.
97. Hooshmand S, Soung Y, Lucas EA, Madihally SV, Levenson CW, Arjmandi BH. Genistein reduces the production of proinflammatory molecules in human chondrocytes. J Nutr Biochem 2007; 18: 609-614.
98. Lim YH, Kim IH, Seo JJ. In vitro activity of kaempferol isolated from the impatiens balsamina alone and in combination with erythromycin or clindamycin against propionibacterium acnes. J Microbiol 2007; 45: 473-47.
99. Lee KM, Kang NJ, Han JH, Lee KW, Lee HJ. Myricetin downregulates phorbol ester-induced cyclooxygenase-2 expression in mouse epidermal cells by blocking activation of nuclear factor kappa B. J Agric Food Chem 2007; 55: 9678-9684.
100. Wilcox LJ, Borradaile NM, Huff NW. Antiatherogenic Properties of Naringenin, a Citrus Flavonoid. Cardiovas Drug Rev 1999, 17: 160-178.
101. Chen Y, Yang L, Lee TJ. Oroxylin A inhibition of lipopolysaccharide-induced iNOS and COX-2 gene expression via suppression of nuclear factor-kappaB activation. Biochem Pharmacol 2000; 59: 445-457.
102. Szewczuk LM, Forti L, Stivala LA, Penning TM. Resveratrol is a peroxidase-mediated inactivator of cox-1 but not cox-2. a mechanistic approach to the design of cox-1 selective agents. J Biol Chem 2004; 279: 22727-22737.
103. Zykova TA, Zhu F, Zhai X, et al. Resveratrol directly targets COX- 2 to inhibit carcinogenesis. Mol Carcinog 2008; 47: 797-805.
104. Hernández V, del Carmen RM, Máñez S, Prieto JM, Giner RM, Ríos JL. A mechanistic approach to the in vivo anti-inflammatory activity of sesquiterpenoid compounds isolated from inula viscose. Planta Med 2001; 67: 726-731.
105. Kaneko K, Chiba H, Horie N, et al. Inhibition of prostaglandin E2 production by flavone and its related compounds. In Vivo 2010; 24: 55-58.
106. Rao CV. Regulation of COX and LOX by curcumin. Adv Exp Med Biol 2007; 595: 213-226.
107. Magalhães CB, Riva DR, DePaula LJ, et al. In vivo anti-inflammatory action of eugenol on lipopolysaccharide-induced lung injury. J Appl Physiol 2010; 108: 845-851.
108. Lai CS, Lee JH, Ho CT, et al. Rosmanol potently inhibits lipopolysaccharide-induced iNOS and COX-2 expression through downregulating MAPK, NF-kappaB, STAT3 and C/EBP signaling pathways. J Agric Food Chem 2009; 57: 10990-10998.
109. Chen YC, Shen SC, Chen LG, Lee TJF, Yang LL. Wogonin, baicalin, baicalein inhibition of inducible nitric oxide synthase and cyclooxygenae-2 gene expressions induced by nitric oxide sythase inhibitors and lipopolysaccharide. Biochem Pharma 2001; 61: 1417-1427.
110. Takada Y, Aggarwal BB. Betulinic acid suppresses metalloprotease-9, cyclooxygenase-2 and matrix phosphorylation: abrogation of I{kappa}B{alpha} kinase and p65 activation through inhibition of carcinogen-induced NF-{kappa}B. J Immunol 2003; 171: 3278-3286.
111. Pinnaa GF, Fiorucci M, Reimund JM, Taquet N, Arondel Y, Muller CD. Celastrol inhibits pro-inflammatory cytokine secretion in Crohn's disease biopsies. Biochem Biophys Res Commun 2004; 322: 778-786.
112. Park W, Lim W, Cho J, Inoue H, Rhyu MR, Lee Y. Inhibitory effects of ginsenoside-Rb1 on activation of the 12-O-tetradecanoyl-phorbol 13-acetate-induced cyclooxygenase-2 promoter. Planta Med 2006; 72: 272-275.
113. Menegazzi M, Di Paolab R, Mazzon E, et al. Glycyrrhizin attenuates the development of carrageenan-induced lung injury in mice. Pharmacol Res 2008; 58: 22-31.
114. Li W, Tsubouchi R, Qiao S, Haneda M, Murakami K, Yoshino M. Inhibitory action of eugenol compounds on the production of nitric oxide in RAW264.7 macrophages. Biomed Res 2006; 27: 69-74.
115. de las Heras B, Rodríguez B., Boscá L, Villar AM. Terpenoids: sources, structure elucidation and therapeutic potential in inflammation. Curr Top Med Chem 2003; 3: 171-185.
116. Smolinski AT, Pestka JJ. Comparative effects of the herbal constituent parthenolide (Feverfew) on lipopolysaccharide-induced inflammatory gene expression in murine spleen and liver. J Inflamm 2005; 2: 26-32.
117. Alexandrakis M, Letourneau R, Kempuraj D, et al. Flavones inhibit proliferation and increase mediator content in human leukemic mast cells (HMC-1). Eur J Haematol 2003; 71: 448-454.
118. Xiao C, Zhou J, He Y, et al. Effects of triptolide from radix tripterygium wilfordii (Leigongteng) on cartilage cytokines and transcription factor NF-κB: a study on induced arthritis in rats. Chin Med 2009; 4: 13.
119. McNish PGM, Davis JA, Blackwood RA, Brock TG. Colchicine inhibits arachidonate release and 5-lipoxygenase action in alveolar macrophages. Cell Mol Physiol 1996; 271: 1004-1013.
120. Werz O. Inhibition of 5-lipoxygenase product synthesis by natural compounds of plant origin. Planta Med 2007; 73: 1331-1357.
121. Seeram NP, Momin RA, Nair MG, Bourquin LD. Cyclooxygenase inhibitory and antioxidant cyanidin glycosides in cherries and berries. Phytomedicine 2001; 8: 362-369.
122. Bang JS, Oh DH, Choi HM, et al. Anti-inflammatory and antiarthritic effects of piperine in human interleukin 1betastimulated fibroblast-like synoviocytes and in rat arthritis models. Arthritis Res Ther 2009; 11: R49.
123. Stöhr JR, Xiao PG, Bauer R. Constituents of Chinese Piper species and their inhibitory activity on prostaglandin and leukotriene biosynthesis in vitro. J Ethnopharmacol 2001; 75: 133-139.
124. Hong J, Bose M, Ju J, et al. Modulation of arachidonic acid metabolism by curcumin and related b-diketone derivatives: effects on cytosolic phospholipase A2, cyclooxygenases and 5-lipoxygenase. Carcinogenesis 2004; 25: 1671-1679.
125. Wadsworth TL, McDonald TL, Koop DR. Effects of Ginkgo biloba extract (EG761) and Quercetin on lipopolysaccharide-induced signaling pathways involved in the release of tumor necrosis factor-α. Biochem Pharm 2001; 62: 963-974.
126. Rackova L, Oblozinsky M, Kostalova D, Kettmann V, Bezakova L. Free radical scavenging activity and lipoxygenase inhibition of Mahonia aquifolium extract and isoquinoline alkaloids. J Inflamm (Lond) 2007; 4: 15-20.
127. Kim HK, Son HK, Chang HW, Kang SS, Kim HP. Inhibition of rat adjuvant-induced arthritis by Ginkgetin a bioflavone from Ginkgo bilba leaves. Planta Med 1999; 65: 465-467.
128. Mastuda H, Morikawa T, Ueda K, Managi H, Yoshikawa M. Structural requirements of flavonoids for inhibition of antigen-Induced degranulation, TNF-α and IL-4 production from RBL-2H3 cells. Bioorg Med Chem 2002; 10: 3123-318.
129. Nishimura OD, Khiba K, Nakai M, et al. Sesquiterpene lactone parthenolide suppresses tumor growth in a xenograft model of renal cell carcinoma by inhibiting the activation of NF-κB. Int J Cancer 2007; 120: 2576-2581.
130. Máñez S, Hernández V, Giner RM, Ríos JL, del Carmen RM. Inhibition of pro-inflammatory enzymes by inuviscolide, a sesquiterpene lactone from Inula viscose. Fitoterapia 2007; 78: 329-331.
131. Yokohira M, Yamakawa K, Saoo K, et al. Antioxidant effects of flavonoids used as food additives (purple corn color, enzymatically modified isoquercitrin, and isoquercitrin) on liver carcinogenesis in a rat medium-term bioassay. Food Sci 2008; 73: C561-C568.
132. Xu YW, Sun L, Liang, H, Sun GM, Cheng Y. 12/15-Lipoxygenase inhibitor baicalein suppresses PPAR gamma expression and nuclear translocation induced by cerebral ischemia/reperfusion. Brain Res 2010; 1307: 149-157.
133. Gutierrez-Lugo MT, Descharmps JD, Holman TR, Suarez E, Timmermann BN. Lipoxygenase inhibition by anadanthiflavone, a new flavonoid from the aerial parts of anadenanthera colubrine. Planta Med 2004; 70: 263-265.
134. Hirotani M, Aska I, Ino C, Furuya T, Shiro M. Ganoderic acid derivatives and ergosta-4,7,22-triene-3,6-dione from Ganoderma lucidum. Phytochemistry 1987; 26: 2797-2803.
135. Agarwal S, Chandrani A, Praveen D, Karnati RR, Venkateswara GR, Pallu R. Inhibition of 12-LOX and COX-2 reduces the proliferation of human epidermoid carcinoma cells (A431) by modulating the ERK and PI3K-Akt signaling pathways. Exp Dermatol 2009; 8: 939-946.
136. Sadik CD, Sies H, Schewe T. Inhibition of 15-lipoxygenases by flavonoids: structure-activity relations and mode of action. Biochem Pharmacol 2003; 65: 773-781.
137. Lapchak PA, Maherd P, Schubertd D, Zivin JA. Baicalein, an antioxidant 12/15-lipoxygenase inhibitor improves clinical rating scores following multiple infarct embolic strokes. Neuroscience 2007; 150: 585-591.
138. Deschamps JD, Kenyon VA, Holman TR. Baicalein is a potent in vitro inhibitor against both reticulocyte 15-human and platelet 12-human lipoxygenases. Bioorg Med Chem 2006; 14: 4295-4301.
139. Hsieh RJ, German JB, Kinsella JE. Relative inhibitory potencies of flavonoids on 12-lipoxygenase of fish gill. Lipids 1998; 23: 322-326.
140. Redrejo-Rodriguez M, Tejeda-Cano A, del Carmen PM, Macías P. Lipoxygenase inhibition by flavonoids: semiempirical study of the structure-activity relation. J Mol Structure: THEOCHEM 2004; 674: 121-124.
141. Tosuna A, Akkolb EK, Bahadira O, Yeşilada E. Evaluation of anti-inflammatory and antinociceptive activities of some Onosma L. species growing in Turkey. J Ethnopharmacol 2008; 120: 378-81.
142. Schneider I, Bucar F. Lipoxygenase inhibitors from natural plant sources. Part 2: medicinal plants with inhibitory activity on arachidonate 12-lipoxygenase, 15-lipoxygenase and leukotriene receptor antagonists. Phytother Res 2005; 19: 263-272.
143. Rajic A, Kweifio-Okai G, Macrides T, Sandeman RM, Chandler DS, Polya GM. Inhibition of serine proteases by anti-inflammatory triterpenoids. Planta Med 2000; 66: 206-210.
144. Yoshimoto T, Furukawa M, Yamamoto S, Horie T, Watanabe-Kohno S. Flavonoids: potent inhibitors of arachidonate 5-lipoxygenase. Biochem Biophys Res Commun 1983; 116: 612-618.
145. Hirano T, Higa S, Arimitsu J, et al. Flavonoids such as luteolin, fisetin and apigenin are inhibitors of interleukin-4 and interleukin-13 production by activated human basophils. Int Arch Allergy Immunol 2004; 134: 135-140.
146. Mihara M, Shiina M, Nishimoto N, Yoshizaki K, Kishimoto T, Akamatsu KI. Anti-interleukin 6 receptor antibody inhibits murine AA-amyloidosis. Rheumatol 2004; 31: 1132-1138.
147. Fattori E, Cappelletti M, Costa P, et al. Defective inflammatory response in interleukin 6-deficient mice. J Cell Biol 1994; 180: 1243-1250.
148. Elliott MJ, Maini RN, Feldmann M, et al. Repeated therapy with monoclonal antibody to tumour necrosis factor α (cA2) in patients with rheumatoid arthritis. Lancet 1994; 344: 1125-1127.
149. Kishimoto T. Interleukin-6: from basic science to medicine -- 40 years in immunology. Annu Rev Immunol 2005; 23: 1-21.
150. Habtemarian S. Natural inhibitors of tumor necrosis factor αproduction secretion and function. Planta Med 2000; 66: 303-313.
151. Gulcubuk A, Altunatmaz K, Sonmez K, et al. Effects of curcumin on tumour necrosis factor-α and interleukin-6 in the late phase of experimental acute pancreatitis. J Vet Med Series A 2006; 53: 49-54.
152. Ikezoe T, Yang Y, Bandobashi K, et al. Oridonin, a diterpenoid purified from Rabdosia rubescens, inhibits the proliferation of cells from lymphoid malignancies in association with blockade of the NF-κB signal pathways. Mol Cancer Ther 2005; 4: 578-586.
153. Wakabayashi C, Hasegawa H, Murata J, Saiki I. In vivo antimetastatic action of ginseng protopanaxadiol saponins is basedon their intestinal bacterial metabolites after oral administration. Oncol Res 1998; 9: 411-417.
154. Kim HA, Kim S, Chang SH, Hwang HJ, Choi YN. Anti-arthritic effect of ginsenoside Rb1 on collagen induced arthritis in mice. Int Immunopharm 2007; 7: 1286-1291.
155. Kim SH, Lee YC. Piperine inhibits eosinophil infiltration and airway hyperresponsiveness by suppressing T cell activity and Th2 cytokine production in the ovalbumin-induced asthma model. J Pharm Pharmacol 2009; 61: 353-359.
156. De Silva1 C, Stevens R, Jordan KM. Inflammatory aortitis controlled by the Chinese herbal remedy Donglingcao Pian. Rheumatology 2008; 47: 1257-1259.
157. Cheong H, Ryu SY, Oak MH, Cheon SH, Yoo GS, Kim KM. Studies of structure activity relationship of flavonoids for the antiallergic actions. Arch Pharm Res 1998, 21: 478-480.
158. Arntz OJ, Geurts J, Veenbergen S, et al. A crucial role for tumor necrosis factor receptor 1 in synovial lining cells and the reticuloendothelial system in mediating experimental arthritis. Arthritis Res Ther 2010; 12: R61.
159. Hu JM, Du J, Li Y, Liu JW. Oridonin promotes CD4+/CD25+ Treg differentiation, modulates Th1/Th2 balance and induces HO-1 in rat splenic lymphocytes. Inflam Res 2008; 57: 163-170.
160. Jayaprakasam B, Doddaga S, Wang R, Holmes D, Goldfarb J, Li XM. Licorice flavonoids inhibit eotaxin-1 secretion by human fetal lung fibroblast in vitro. J Agric Food Chem 2009; 57: 820-825.
161. Rankin SM, Conroy DM, Williams TJ. Eotaxin and eosinophil recruitment: implications for human disease. Trend Mol Med 2000; 6: 20-27.
162. Nakajima T, Imanishi M, Yamamoto K, Cyong JC, Hirai K. Inhibitory effect of baicalein, a flavonoids in Scutellaria root, on eotaxin production by human dermal fibroblasts. Planta Med 2001; 67: 132-135.
163. Yano S, Umeda D, Maeda N, Fujimura Y, Yamada K, Tachibana H. Dietary apigenin suppresses IgE and inflammatory cytokines production in C57BL/6N Mice. J Agric Food Chem 2006; 54: 5203-5207.
164. Cohn L, Homer RJ, Marinov A, Rankin J, Bottomly K. Induction of airway mucus production by T helper 2 (Th2) cells: a critical role for interleukin 4 in cell recruitment but not mucus production. J Exp Med 1997; 186: 1737-1747.
165. Krishnamoorthy S, Jin R, Cai Y, et al. 12-Lipoxygenase and the regulation of hypoxia-inducible factor 3 in prostate cancer cells. Exp Cell Res 2010; 316: 1706-1715.
166. Smith WL, DeWitt DL, Garavito RM. Cyclooxygenases: structural, cellular, and molecular biology. Annu Rev Biochem 2000; 69: 145-182.
167. Amanda R, Hajek BS, Alexa R, et al. 12/15-Lipoxygenase deficiency protects mice from allergic airways inflammation and increases secretory IgA levels. J Allergy Clin Immunol 2008; 22: 633-639.
168. Israel E, Dermarkarian R, Rosenberg M, et al. The effects of a 5-lipoxygenase inhibitor on asthma induced by cold, dry air. NEJM 1990; 323: 1740-1744.
169. Peters-Golden M. Cell biology of the 5-lipoxygenase pathway. Am J Respir Crit Care Med 1998; 157: S227-S232.
170. Woodruff PG, Modrek B, Choy DF, et al. T-helper type 2-driven inflammation defines major subphenotypes of asthma. Am J Respir Crit Care Med 2009; 180: 388-395.
171. Furse KE, Pratt DA, Porter NA, Lybrand TP. Molecular dynamics simulations of arachidonic acid complexes with COX-1 and COX-2: insights into equilibrium behavior. Biochemistry 2006; 45: 3189-31205.
172. Yang K, Ma W, Liang H, Quyang Q, Tang C, Lai L. Dynamic simulations on the arachidonic acid metabolic network. PLoS Comput Biol 2007; 3: 523-530.