Honokiol, a multifunctional antiangiogenic and antitumor agent

Antioxidants and Redox Signaling

Volumn 11, Issue 5, 2009, Pages 1139-1148

  Fried, Levi E ^a   Arbiser, Jack L ^a  

^a EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CISPLATIN; CYCLOPHILIN D; CYCLOSPORIN A; DOCETAXEL; HONOKIOL; PHOSPHOLIPASE D; PROTEIN P53; PROTEIN TYROSINE KINASE INHIBITOR; RAS PROTEIN; REACTIVE OXYGEN METABOLITE; ANGIOGENESIS INHIBITOR; ANTINEOPLASTIC AGENT; ANTIVIRUS AGENT; BIPHENYL DERIVATIVE; LIGNAN;

ANTIANGIOGENIC ACTIVITY; ANTIBACTERIAL ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; APOPTOSIS; CANCER CELL; CELL PROTECTION; CONCENTRATION RESPONSE; DRUG ANTAGONISM; DRUG ISOLATION; DRUG POTENTIATION; DRUG STRUCTURE; DRUG SYNTHESIS; GRAFT REJECTION; HUMAN; HYPERTENSION; KIDNEY DYSFUNCTION; LUNG CANCER; LYMPHOMA; MITOCHONDRIAL PERMEABILITY; NONHUMAN; PRIORITY JOURNAL; PROTEIN FUNCTION; PROTEIN PROTEIN INTERACTION; REVIEW; SIGNAL TRANSDUCTION; SKIN CANCER; ANIMAL; METABOLISM; MOUSE; TUMOR CELL LINE;

ANGIOGENESIS INHIBITORS; ANIMALS; ANTINEOPLASTIC AGENTS; ANTIVIRAL AGENTS; BIPHENYL COMPOUNDS; CELL LINE, TUMOR; LIGNANS; MICE; REACTIVE OXYGEN SPECIES;

MAGNOLIA;

EID: 64749084915     PISSN: 15230864     EISSN: None     Source Type: Journal    
DOI: 10.1089/ars.2009.2440     Document Type: Review

References (62)

1. Ahn KS, Sethi G, Shishodia S, Sung B, Arbiser JL, and Aggarwal BB. Honokiol potentiates apoptosis, suppresses osteoclastogenesis, and inhibits invasion through modulation of nuclear factor-kappaB activation pathway. Mol Cancer Res 4: 621-633, 2006.
2. Ai J, Wang X, and Nielsen M. Honokiol and magnolol selectively interact with GABAA receptor subtypes in vitro. Pharmacology 63: 34-41, 2001.
3. Amblard F, Delinsky D, Arbiser JL, and Schinazi RF. Facile purification of honokiol and its antiviral and cytotoxic properties. J Med Chem 49: 3426-3427, 2006.
4. Amblard F, Govindarajan B, Lefkove B, Rapp KL, Detorio M, Arbiser JL, and Schinazi RF. Synthesis, cytotoxicity, and antiviral activities of new neolignans related to honokiol and magnolol. Bioorg Med Chem Lett 17: 4428-4431, 2007.
5. Aoshima H and Hamamoto K. Potentiation of GABAA receptors expressed in Xenopus oocytes by perfume and phytoncid. Biosci Biotechnol Biochem 63: 743-748, 1999.
6. Arbiser JL. Why targeted therapy hasn't worked in advanced cancer. J Clin Invest 117: 2762-2765, 2007.
7. Arbiser JL, Bingaman A, Durham M, Cowan S, Cohen C, Zarnegar E, Varma V, and Larsen CP. SVR angiosarcomas can be rejected by CD4 costimulation dependent and CD8 costimulation independent pathways. Mol Med 8: 551-558, 2002.
8. Arican O, Aral M, Sasmaz S, and Ciragil P. Serum levels of TNF-alpha, IFN-gamma, IL-6, IL-8, IL-12, IL-17, and IL-18 in patients with active psoriasis and correlation with disease severity. Mediators Inflamm 2005: 273-279, 2005.
9. Bai X, Cerimele F, Ushio-Fukai M, Waqas M, Campbell PM, Govindarajan B, Der CJ, Battle T, Frank DA, Ye K, Murad E, Dubiel W, Soff G, and Arbiser JL. Honokiol, a small molecular weight natural product, inhibits angiogenesis in vitro and tumor growth in vivo. J Biol Chem 278: 35501-35507, 2003.
10. Battle TE, Arbiser J, and Frank DA. The natural product honokiol induces caspase-dependent apoptosis in B-cell chronic lymphocytic leukemia (B-CLL) cells. Blood 106: 690- 697, 2005.
11. Chang B, Lee Y, Ku Y, Bae K, and Chung C. Antimicrobial activity of magnolol and honokiol against periodontopathic microorganisms. Planta Med 64: 367-369, 1998.
12. Chiu JH, Ho CT, Wei YH, Lui WY, and Hong CY. In vitro and in vivo protective effect of honokiol on rat liver from peroxidative injury. Life Sci 61: 1961-1971, 1997.
13. Choi MS, Lee SH, Cho HS, Kim Y, Yun YP, Jung HY, Jung JK, Lee BC, Pyo HB, and Hong JT. Inhibitory effect of obovatol on nitric oxide production and activation of NF-kappaB/MAP kinases in lipopolysaccharide-treated RAW 264.7cells. Eur J Pharmacol 556: 181-189, 2007.
14. Clark AM, El-Feraly FS, and Li WS. Antimicrobial activity of phenolic constituents of Magnolia grandiflora L. J Pharm Sci 70: 951-952, 1981.
15. Dikalov S, Losik T, and Arbiser JL. Honokiol is a potent scavenger of superoxide and peroxyl radicals. Biochem Pharmacol 76: 589-596, 2008.
16. Esumi T, Makado G, Zhai H, Shimizu Y, Mitsumoto Y, and Fukuyama Y. Efficient synthesis and structure-activity relationship of honokiol, a neurotrophic biphenyl-type neolignan. Bioorg Med Chem Lett 14: 2621-2625, 2004.
17. Fujita M, Itokawa H, and Sashida Y. [Studies on the components of Magnolia obovata Thunb, 3: occurrence of magnolol and honokiol in M. obovata and other allied plants]. Yakugaku Zasshi 93: 429-434, 1973.
18. Funa NS, Reddy K, Bhandarkar S, Kurenova EV, Yang L, Cance WG, Welsh M, and Arbiser JL. Shb gene knockdown increases the susceptibility of SVR endothelial tumor cells to apoptotic stimuli in vitro and in vivo. J Invest Dermatol 2007.
19. Garcia A, Zheng Y, Zhao C, Toschi A, Fan J, Shraibman N, Brown HA, Bar-Sagi D, Foster DA, and Arbiser JL. Honokiol suppresses survival signals mediated by Ras-dependent phospholipase D activity in human cancer cells. Clin Cancer Res 14: 4267-4274, 2008.
20. Hahm ER, Arlotti JA, Marynowski SW, and Singh SV. Honokiol, a constituent of oriental medicinal herb Magnolia officinalis, inhibits growth of PC-3 xenografts in vivo in association with apoptosis induction. Clin Cancer Res 14: 1248- 1257, 2008.
21. Hamasaki Y, Muro E, Miyanji S, Yamamoto S, Kobayashi I, Sato R, Zaitu M, Matsuo M, Ichimaru T, Tasaki H, and Miyazaki S. Inhibition of leukotriene synthesis by honokiol in rat basophilic leukemia cells. Int Arch Allergy Immunol 110: 278-281, 1996.
22. Hibasami H, Achiwa Y, Katsuzaki H, Imai K, Yoshioka K, Nakanishi K, Ishii Y, Hasegawa M, and Komiya T. Honokiol induces apoptosis in human lymphoid leukemia Molt 4B cells. Int J Mol Med 2: 671-673, 1998.
23. Ho KY, Tsai CC, Chen CP, Huang JS, and Lin CC. Antimicrobial activity of honokiol and magnolol isolated from Magnolia officinalis. Phytother Res 15: 139-141, 2001.
24. Hui L, Zheng Y, Yan Y, Bargonetti J, and Foster DA. Mutant p53 in MDA-MB-231 breast cancer cells is stabilized by elevated phospholipase D activity and contributes to survival signals generated by phospholipase D. Oncogene 25: 7305- 7310, 2006. Epub June 19, 2006.
25. Ishigame H, Nakajima A, Saijo S, Komiyama Y, Nambu A, Matsuki T, Nakae S, Horai R, Kakuta S, and Iwakura Y. The role of TNFalpha and IL-17 in the development of excess IL- 1 signaling-induced inflammatory diseases in IL-1 receptor antagonist-deficient mice. Ernst Schering Res Found Workshop 129-153, 2006.
26. Ishitsuka K, Hideshima T, Hamasaki M, Raje N, Kumar S, Hideshima H, Shiraishi N, Yasui H, Roccaro AM, Richardson P, Podar K, Le GS, Chauhan D, Tamura K, Arbiser J, and Anderson KC. Honokiol overcomes conventional drug resistance in human multiple myeloma by induction of caspase-dependent and -independent apoptosis. Blood 106: 1794-1800, 2005.
27. Jacamo R, Jiang X, Lunn JA, and Rozengurt E. FAK phosphorylation at Ser-843 inhibits Tyr-397 phosphorylation, cell spreading and migration. J Cell Physiol 210: 436-444, 2007.
28. Ko CH, Chen HH, Lin YR, and Chan MH. Inhibition of smooth muscle contraction by magnolol and honokiol in porcine trachea. Planta Med 69: 532-536, 2003.
29. Konoshima T, Kozuka M, Tokuda H, Nishino H, Iwashima A, Haruna M, Ito K, and Tanabe M. Studies on inhibitors of skin tumor promotion, IX: neolignans from Magnolia officinalis. J Nat Prod 54: 816-822, 1991.
30. Kuribara H, Kishi E, Kimura M, Weintraub ST, and Maruyama Y. Comparative assessment of the anxiolytic-like activities of honokiol and derivatives. Pharmacol Biochem Behav 67: 597-601, 2000.
31. Li L, Han W, Gu Y, Qiu S, Lu Q, Jin J, Luo J, and Hu X. Honokiol induces a necrotic cell death through the mitochondrial permeability transition pore. Cancer Res 67: 4894- 4903, 2007.
32. Liou KT, Shen YC, Chen CF, Tsao CM, and Tsai SK. The anti-inflammatory effect of honokiol on neutrophils: mechanisms in the inhibition of reactive oxygen species production. Eur J Pharmacol 475: 19-27, 2003.
33. Liu Y, Chen L, He X, Fan L, Yang G, Chen X, Lin X, DU L, Li Z, Ye H, Mao Y, Zhao X, and Wei Y. Enhancement of therapeutic effectiveness by combining liposomal honokiol with cisplatin in ovarian carcinoma. Int J Gynecol Cancer 18: 652- 659, 2008. Epub September 24, 2007.
34. Lo YC, Teng CM, Chen CF, Chen CC, and Hong CY. Magnolol and honokiol isolated from Magnolia officinalis protect rat heart mitochondria against lipid peroxidation. Biochem Pharmacol 47: 549-553, 1994.
35. Luvisetto S, Basso E, Petronilli V, Bernardi P, and Forte M. Enhancement of anxiety, facilitation of avoidance behavior, and occurrence of adult-onset obesity in mice lacking mitochondrial cyclophilin D. Neuroscience 155: 585-596, 2008.
36. Maruyama Y, Kuribara H, Morita M, Yuzurihara M, and Weintraub ST. Identification of magnolol and honokiol as anxiolytic agents in extracts of saiboku-to, an oriental herbal medicine. J Nat Prod 61: 135-138, 1998.
37. Mattioli E, Vogiatzi P, Sun A, Abbadessa G, Angeloni G, D'Ugo D, Trani D, Gaughan JP, Vecchio FM, Cevenini G, Persiani R,Giordano A, and Claudio PP. Immunohistochemical analysis of pRb2/p130, VEGF, EZH2, p53, p16(INK4A), p27(KIP1), p21(WAF1), Ki-67 expression patterns in gastric cancer. J Cell Physiol 210: 183-191, 2007.
38. Munroe ME, Arbiser JL, and Bishop GA. Honokiol, a natural plant product, inhibits inflammatory signals and alleviates inflammatory arthritis. J Immunol 179: 753-763, 2007.
39. Otley CC and Pittelkow MR. Skin cancer in liver transplant recipients. Liver Transpl 6: 253-262, 2000.
40. Ou HC, Chou FP, Sheu WH, Hsu SL, and Lee WJ. Protective effects of magnolol against oxidized LDL-induced apoptosis in endothelial cells. Arch Toxicol 81: 421-432, 2007.
41. Park EJ, Kim SY, Zhao YZ, and Sohn DH. Honokiol reduces oxidative stress, c-jun-NH2-terminal kinase phosphorylation and protects against glycochenodeoxycholic acid-induced apoptosis in primary cultured rat hepatocytes. Planta Med 72: 661-664, 2006.
42. Park EJ, Zhao YZ, Na M, Bae K, Kim YH, Lee BH, and Sohn DH. Protective effects of honokiol and magnolol on tertiary butyl hydroperoxide- or D-galactosamine-induced toxicity in rat primary hepatocytes. Planta Med 69: 33-37, 2003.
43. Shen YC, Sung YJ, and Chen CF. Magnolol inhibits Mac-1 (CD11b/CD18)-dependent neutrophil adhesion: relationship with its antioxidant effect. Eur J Pharmacol 343: 79-86, 1998.
44. Sheu ML, Chiang CK, Tsai KS, Ho FM, Weng TI, Wu HY, and Liu SH. Inhibition of NADPH oxidase-related oxidative stress-triggered signaling by honokiol suppresses high glucose-induced human endothelial cell apoptosis. Free Radic Biol Med 44: 2043-2050, 2008.
45. Sheu ML, Liu SH, and Lan KH. Honokiol induces calpainmediated glucose-regulated protein-94 cleavage and apoptosis in human gastric cancer cells and reduces tumor growth. PLoS ONE 2: e1096, 2007.
46. Shigemura K, Arbiser JL, Sun SY, Zayzafoon M, Johnstone PA, Fujisawa M, Gotoh A, Weksler B, Zhau HE, and Chung LW. Honokiol, a natural plant product, inhibits the bone metastatic growth of human prostate cancer cells. Cancer 109: 1279-1289, 2007.
47. Squires RF and Saederup E. Additivities of compounds that increase the numbers of high affinity [3H]muscimol binding sites by different amounts define more than 9 GABA(A) receptor complexes in rat forebrain: implications for schizophrenia and clozapine research. Neurochem Res 25: 1587-1601, 2000.
48. Sukumaran K, Unnikrishnan MC, and Kuttan R. Inhibition of tumour promotion in mice by eugenol. Indian J Physiol Pharmacol 38: 306-308, 1994.
49. Syu WJ, Shen CC, Lu JJ, Lee GH, and Sun CM. Antimicrobial and cytotoxic activities of neolignans from Magnolia officinalis. Chem Biodivers 1: 530-537, 2004.
50. Takeya, T, Okubo, T, and Tobinaga, S. Synthesis of unsymmetrical biphenyl lignans, honokiol and related compounds, utilizing quinol-acetates as reactive intermediates. Chem Pharm Bull 34: 2066-2075. 1986.
51. Taniguchi C, Homma M, Takano O, Hirano T, Oka K, Aoyagi Y, Niitsuma T, and Hayashi T. Pharmacological effects of urinary products obtained after treatment with saiboku-to, a herbal medicine for bronchial asthma, on type IV allergic reaction. Planta Med 66: 607-611, 2000.
52. Tsai SK, Huang SS, and Hong CY. Myocardial protective effect of honokiol: an active component in Magnolia officinalis. Planta Med 62: 503-506, 1996.
53. Tse AK, Wan CK, Shen XL, Yang M, and Fong WF. Honokiol inhibits TNF-alpha-stimulated NF-kappaB activation and NF-kappaB-regulated gene expression through suppression of IKK activation. Biochem Pharmacol 70: 1443-1457, 2005.
54. Wang T, Chen F, Chen Z, Wu YF, Xu XL, Zheng S, and Hu X. Honokiol induces apoptosis through p53-independent pathway in human colorectal cell line RKO. World J Gastroenterol 10: 2205-2208, 2004.
55. Wang X, Mu H, Chai H, Liao D, Yao Q, and Chen C. Human immunodeficiency virus protease inhibitor ritonavir inhibits cholesterol efflux from human macrophage-derived foam cells. Am J Pathol 171: 304-314, 2007.
56. Watanabe H, Watanabe K, and Hagino K. Chemostructural requirement for centrally acting muscle relaxant effect of magnolol and honokiol, neolignane derivatives. J Pharmacobiodyn 6: 184-190, 1983.
57. Watanabe K, Watanabe HY, Goto Y, Yamamoto N, and Yoshizaki M. Studies on the active principles of magnolia bark: centrally acting muscle relaxant activity of magnolol and honokiol. Jpn J Pharmacol 25: 605-607, 1975.
58. Withers BE, Hanks SK, and Fry DW. Correlations between the expression, phosphotyrosine content and enzymatic activity of focal adhesion kinase, pp125FAK, in tumor and nontransformed cells. Cancer Biochem Biophys 15: 127-139, 1996.
59. Wolf I, O'Kelly J, Wakimoto N, Nguyen A, Amblard F, Karlan BY, Arbiser JL, and Koeffler HP. Honokiol, a natural biphenyl, inhibits in vitro and in vivo growth of breast cancer through induction of apoptosis and cell cycle arrest. Int J Oncol 30: 1529-1537, 2007.
60. Xu D, Lu Q, and Hu X. Down-regulation of P-glycoprotein expression in MDR breast cancer cell MCF-7/ADR by honokiol. Cancer Lett 18: 274-280, 2006. Epub January 10, 2006.
61. Yamazaki R, Sugatani J, Fujii I, Kuroyanagi M, Umehara K, Ueno A, Suzuki Y, and Miwa M. Development of a novel method for determination of acetyl-CoA:1-alkyl-sn-glycero- 3-phosphocholine acetyltransferase activity and its application to screening for acetyltransferase inhibitors: inhibition by magnolol and honokiol from magnoliae cortex. Biochem Pharmacol 47: 995-1006, 1994.
62. Zhong M, Shen Y, Zheng Y, Joseph T, Jackson D, and Foster DA. Phospholipase D prevents apoptosis in v-Srctransformed rat fibroblasts and MDA-MB-231 breast cancer cells. Biochem Biophys Res Commun 302: 615-619, 2003.