Costunolide: A novel anti-cancer sesquiterpene lactone

Authors

  • Azhar Rasul Central Research Laboratory, Jilin University Bethune Second Hospital, Changchun 130041
  • Saima Parveen Department of Chemistry, Faculty of Science, The Islamia University of Bahawalpur, Bahawalpur 63100
  • Tonghui Ma Central Research Laboratory, Jilin University Bethune Second Hospital, Changchun 130041

DOI:

https://doi.org/10.3329/bjp.v7i1.10066

Keywords:

Anticancer, Apoptosis, Costunolide, Natural compound, Sesquiterpene lactone

Abstract

Currently an ample interest is found among oncologists to explore anticancer compounds from herbs. Sesquiterpene lactones have accredited significant attention in pharmacological research. Costunolide is a well-known sesquiterpene lactone present in plants used as popular herbal remedy. Several plant-derived compounds are currently successfully employed in cancer treatment. Growing evidences demonstrated that costunolide possesses anticancer activities by inhibiting cell proliferation, tumor invasion, angiogenesis, metastasis and inducing apoptosis of a variety of tumor cell lines. This review is aimed to summarize the recent researches about costunolide focusing on anti-tumor activity and to lay emphasis on its molecular targets and its mechanisms, which may help the further design and conduct of preclinical and clinical trials.

Downloads

Download data is not yet available.
Abstract
4814
Download
1953

Author Biography

Tonghui Ma, Central Research Laboratory, Jilin University Bethune Second Hospital, Changchun 130041

Director

References

Abbas T, Dutta A. p21 in cancer: Intricate networks and multiple activities. Nat Rev Cancer. 2009; 9: 400-14.

Amin AR, Kucuk O, Khuri FR, Shin DM. Perspectives for cancer prevention with natural compounds. J Clin Oncol. 2009; 27: 2712-25.

Barrero AF, Oltra JE, Alvarez M, Raslan DS, Saude DA, Akssira M. New sources and antifungal activity of sesquiterpene lactones. Fitoterapia 2000; 71: 60-64.

Bocca C, Gabriel L, Bozzo F, Miglietta A. A sesquiterpene lactone, costunolide, interacts with microtubule protein and inhibits the growth of MCF-7 cells. Chem Biol Interact. 2004; 147: 79-86.

Castro V, Murillo R, Klaas CA, Meunier C, Mora G, Pahl HL, Merfort I. Inhibition of the transcription factor NF-kappa B by sesquiterpene lactones from Podachaenium eminens. Planta Med. 2000; 66: 591-95.

Chen CN, Huang HH, Wu CL, Lin CP, Hsu JT, Hsieh HP, Chuang SE, Lai GM. Isocostunolide, a sesquiterpene lactone, induces mitochondrial membrane depolarization and caspase-dependent apoptosis in human melanoma cells. Cancer Lett. 2007; 246: 237-52.

Chen HC, Chou CK, Lee SD, Wang JC, Yeh SF. Active compounds from Saussurea lappa Clarks that suppress hepatitis B virus surface antigen gene expression in human hepatoma cells. Antiviral Res. 1995; 27: 99-109.

Choi JH, Ha J, Park JH, Lee JY, Lee YS, Park HJ, Choi JW, Masuda Y, Nakaya K, Lee KT. Costunolide triggers apoptosis in human leukemia U937 cells by depleting intracellular thiols. Jpn J Cancer Res. 2002a; 93: 1327-33.

Choi JH, Lee KT. Costunolide-induced apoptosis in human leukemia cells: Involvement of c-jun N-terminal kinase activation. Biol Pharm Bull. 2009; 32: 1803-08.

Choi JH, Seo BR, Seo SH, Lee KT, Park JH, Park HJ, Choi JW, Itoh Y, Miyamoto K. Costunolide induces differentiation of human leukemia HL-60 cells. Arch Pharm Res. 2002b; 25: 480-84.

Choi JY, Choi EH, Jung HW, Oh JS, Lee WH, Lee JG, Son JK, Kim Y, Lee SH. Melanogenesis inhibitory compounds from Saussureae Radix. Arch Pharm Res. 2008; 31: 294-99.

Choi SH, Im E, Kang HK, Lee JH, Kwak HS, Bae YT, Park HJ , Kim ND. Inhibitory effects of costunolide on the telomerase activity in human breast carcinoma cells. Cancer Lett. 2005; 227: 153-62.

Choi YK, Seo HS, Choi HS, Kim SR, Shin YC, Ko SG. Induction of Fas-mediated extrinsic apoptosis, p21WAF1-related G2/M cell cycle arrest and ROS generation by costunolide in estrogen receptor-negative breast cancer cells, MDA-MB-231. Mol Cell Biochem. 2011; 363: 119-28.

Corona D, Diaz E, Nava JL, Guzman A, Barrios H, Fuentes A, Hernandez-Plata SA, Allard J, Jankowski CK. (1)H, (13)C NMR and X-ray crystallographic studies of highly polyhalogenated derivatives of costunolide lactone. Spectrochim Acta A Mol Biomol Spectrosc. 2005; 62: 604-13.

Cragg GM, Newman DJ. Plants as a source of anti-cancer agents. J Ethnopharmacol. 2005; 100: 72-79.

De Marino S, Borbone N, Zollo F, Ianaro A, Di Meglio P, Iorizzi M. New sesquiterpene lactones from Laurus nobilis leaves as inhibitors of nitric oxide production. Planta Med. 2005; 71: 706-10.

el-Feraly FS, Chan YM. Isolation and characterization of the sesquiterpene lactones costunolide, parthenolide, costunolide diepoxide, santamarine, and reynosin from Magnolia grandiflora L. J Pharm Sci. 1978; 67: 347-50.

Ferlay J, Shin HR, Bray F, Forman D, Mathers C, Parkin DM. Estimates of worldwide burden of cancer in 2008: GLOBOCAN 2008. Int J Cancer. 2010; 127: 2893-917.

Ferrari B, Castilho P, Tomi F, Rodrigues AI, do Ceu Costa M, Casanova J. Direct identification and quantitative determination of costunolide and dehydrocostuslactone in the fixed oil of Laurus novocanariensis by 13C-NMR spectroscopy. Phytochem Anal. 2005; 16: 104-07.

Fischer NH, Lu T, Cantrell CL, Castaneda-Acosta J, Quijano L, Franzblau SG (1998). Antimycobacterial evaluation of germacranolides. Phytochemistry 1998; 49: 559-64.

Fukuda K, Akao S, Ohno Y, Yamashita K, Fujiwara H. Inhibition by costunolide of phorbol ester-induced transcriptional activation of inducible nitric oxide synthase gene in a human monocyte cell line THP-1. Cancer Lett. 2001; 164: 7-13.

Furuya Y, Lundmo P, Short AD, Gill DL, Isaacs JT. The role of calcium, pH, and cell proliferation in the programmed (apoptotic) death of androgen-independent prostatic cancer cells induced by thapsigargin. Cancer Res. 1994; 54: 6167-75.

Griffioen AW, Molema G. Angiogenesis: Potentials for pharmacologic intervention in the treatment of cancer, cardiovascular diseases, and chronic inflammation. Pharmacol Rev. 2000; 52: 237-68.

Harvey AL. Natural products in drug discovery. Drug Discov Today. 2008; 13: 894-901.

Hibasami H, Yamada Y, Moteki H, Katsuzaki H, Imai K, Yoshioka K, Komiya T. Sesquiterpenes (costunolide and zaluzanin D) isolated from laurel (Laurus nobilis L.) induce cell death and morphological change indicative of apoptotic chromatin condensation in leukemia HL-60 cells. Int J Mol Med. 2003; 12: 147-51.

Hoeben A, Landuyt B, Highley MS, Wildiers H, Van Oosterom AT, De Bruijn EA. Vascular endothelial growth factor and angiogenesis. Pharmacol Rev. 2004; 56: 549-80.

Hsu JL, Pan SL, Ho YF, Hwang TL, Kung FL, Guh JH. Costunolide induces apoptosis through nuclear calcium2+ overload and DNA damage response in human prostate cancer. J Urol. 2011; 185: 1967-74.

Jeong SJ, Itokawa T, Shibuya M, Kuwano M, Ono M, Higuchi R, Miyamoto T. Costunolide, a sesquiterpene lactone from Saussurea lappa, inhibits the VEGFR KDR/Flk-1 signaling pathway. Cancer Lett. 2002; 187: 129-33.

Kang JS, Yoon YD, Lee KH, Park SK, Kim HM. Costunolide inhibits interleukin-1beta expression by down-regulation of AP-1 and MAPK activity in LPS-stimulated RAW 264.7 cells. Biochem Biophys Res Commun. 2004; 313: 171-77.

Kanno S, Kitajima Y, Kakuta M, Osanai Y, Kurauchi K, Ujibe M, Ishikawa M. Costunolide-induced apoptosis is caused by receptor-mediated pathway and inhibition of telomerase activity in NALM-6 cells. Biol Pharm Bull. 2008; 31: 1024-28.

Kassuya CA, Cremoneze A, Barros LF, Simas AS, Lapa Fda R, Mello-Silva R, Stefanello ME, Zampronio AR. Antipyretic and anti-inflammatory properties of the ethanolic extract, dichloromethane fraction and costunolide from Magnolia ovata (Magnoliaceae). J Ethnopharmacol. 2009; 124: 369-76.

Kawamori T, Tanaka T, Hara A, Yamahara J, Mori H. Modifying effects of naturally occurring products on the development of colonic aberrant crypt foci induced by azoxymethane in F344 rats. Cancer Res. 1995; 55: 1277-82.

Kim JH, Yang YI, Lee KT, Park HJ, Choi JH. Costunolide induces apoptosis in human endometriotic cells through inhibition of the prosurvival Akt and nuclear factor kappa B signaling pathway. Biol Pharm Bull. 2011a; 34: 580-85.

Kim SH, Danilenko M, Kim TS. Differential enhancement of leukaemia cell differentiation without elevation of intracellular calcium by plant-derived sesquiterpene lactone compounds. Br J Pharmacol. 2008; 155: 814-25.

Kim SH, Kang SN, Kim HJ, Kim TS. Potentiation of 1,25-dihydroxyvitamin D(3)-induced differentiation of human promyelocytic leukemia cells into monocytes by costunolide, a germacranolide sesquiterpene lactone. Biochem Pharmacol. 2002; 64: 1233-42.

Kim TJ, Nam KW, Kim B, Lee SJ, Oh KB, Kim KH, Mar W, Shin J. Inhibitory Effects of costunolide Isolated from Laurus nobilis on IgE-induced degranulation of mast cell-like RBL-2H3 cells and the growth of Y16 pro-B Cells. Phytother Res. 2011b; 25: 139297.

Ko SG, Kim HP, Jin DH, Bae HS, Kim SH, Park CH, Lee JW. Saussurea lappa induces G2-growth arrest and apoptosis in AGS gastric cancer cells. Cancer Lett. 2005; 220: 11-19.

Komiya T, Yamada Y, Moteki H, Katsuzaki H, Imai K, Hibasami H. Hot water soluble sesquiterpenes [anhydroperoxy-costunolide and 3-oxoeudesma-1,4(15),11(13)triene-12,6alpha-olide] isolated from laurel (Laurus nobilis L.) induce cell death and morphological change indicative of apoptotic chromatin condensation in leukemia cells. Oncol Rep. 2004; 11: 85-88.

Koo TH, Lee JH, Park YJ, Hong YS, Kim HS, Kim KW, Lee JJ. A sesquiterpene lactone, costunolide, from Magnolia grandiflora inhibits NF-kappa B by targeting I kappa B phosphorylation. Planta Med. 2001; 67: 103-07.

Kroemer G, Petit P, Zamzami N, Vayssiere JL, Mignotte B. The biochemistry of programmed cell death. FASEB J. 1995; 9: 1277-87.

Lee MG, Lee KT, Chi SG, Park JH. Costunolide induces apoptosis by ROS-mediated mitochondrial permeability transition and cytochrome C release. Biol Pharm Bull. 2001; 24: 303-06.

Li A, Sun A, Liu R. Preparative isolation and purification of costunolide and dehydrocostuslactone from Aucklandia lappa Decne by high-speed counter-current chromatography. J Chromatogr A. 2005; 1076: 193-97.

Li S, An TY, Li J, Shen Q, Lou FC, Hu LH. PTP1B inhibitors from Saussrurea lappa. J Asian Nat Prod Res. 2006; 8: 281-86.

Liekens S, De Clercq E, Neyts J. Angiogenesis: regulators and clinical applications. Biochem Pharmacol. 2001; 61: 253-70.

Liu CY, Chang HS, Chen IS, Chen CJ, Hsu ML, Fu SL,

Chen YJ. Costunolide causes mitotic arrest and enhances radiosensitivity in human hepatocellular carcinoma cells. Radiat Oncol. 2011; 6: 56.

Liu ZL, He Q, Chu SS, Wang CF, Du SS, Deng ZW. Essential oil composition and larvicidal activity of Saussurea lappa roots against the mosquito Aedes albopictus (Diptera: Culicidae). Parasitol Res. 2012; 110: 2125-30.

Luna-Herrera J, Costa MC, Gonzalez HG, Rodrigues AI, Castilho PC. Synergistic antimycobacterial activities of sesquiterpene lactones from Laurus spp. J Antimicrob Chemother. 2007; 59: 548-52.

Macias FA, Galindo JC, Castellano D, Velasco RF. Sesquiterpene lactones with potential use as natural herbicide models (I): trans,trans-germacranolides. J Agric Food Chem. 1999; 47: 4407-14.

Mata R, Rivero-Cruz I, Rivero-Cruz B, Bye R, Timmermann BN. Sesquiterpene lactones and phenylpropanoids from Cosmos pringlei. J Nat Prod. 2002; 65: 1030-32.

Matsuda H, Kagerura T, Toguchida I, Ueda H, Morikawa T, Yoshikawa M. Inhibitory effects of sesquiterpenes from bay leaf on nitric oxide production in lipopolysaccharide-activated macrophages: Structure requirement and role of heat shock protein induction. Life Sci. 2000; 66: 2151-57.

Matsuda H, Shimoda H, Ninomiya K, Yoshikawa M. Inhibitory mechanism of costunolide, a sesquiterpene lactone isolated from Laurus nobilis, on blood-ethanol elevation in rats: Involvement of inhibition of gastric emptying and increase in gastric juice secretion. Alcohol Alcohol. 2002; 37: 121-27.

Mondranondra IO, Che CT, Rimando AM, Vajrodaya S, Fong HH, Farnsworth NR. Sesquiterpene lactones and other constituents from a cytotoxic extract of Michelia floribunda. Pharm Res. 1990; 7: 1269-72.

Mori H, Kawamori T, Tanaka T, Ohnishi M, Yamahara J. Chemopreventive effect of costunolide, a constituent of oriental medicine, on azoxymethane-induced intestinal carcinogenesis in rats. Cancer Lett. 1994; 83: 171-75.

Nam NH. Naturally occurring NF-kappaB inhibitors. Mini Rev Med Chem. 2006; 6: 945-51.

Newman DJ, Cragg GM. Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007; 70: 461-77.

Pae HO, Jeong GS, Kim HS, Woo WH, Rhew HY, Sohn DH, Kim YC, Chung HT. Costunolide inhibits production of tumor necrosis factor-alpha and interleukin-6 by inducing heme oxygenase-1 in RAW264.7 macrophages. Inflamm Res. 2007; 56: 520-26.

Pandey MM, Rastogi S, Rawat AK. Saussurea costus: Botanical, chemical and pharmacological review of an ayurvedic medicinal plant. J Ethnopharmacol. 2007; 110: 379-90.

Park HJ, Jung WT, Basnet P, Kadota S, Namba T. Syringin 4-O-beta-glucoside, a new phenylpropanoid glycoside, and costunolide, a nitric oxide synthase inhibitor, from the stem bark of Magnolia sieboldii. J Nat Prod. 1996; 59: 1128-30.

Park HJ, Kwon SH, Han YN, Choi JW, Miyamoto K, Lee SH, Lee KT. Apoptosis-Inducing costunolide and a novel acyclic monoterpene from the stem bark of Magnolia sieboldii. Arch Pharm Res. 2001a; 24: 342-48.

Park HW, Lee JH, Choi SU, Baek NI, Kim SH, Yang JH, Kim DK. Cytotoxic germacranolide sesquiterpenes from the bark of Magnolia kobus. Arch Pharm Res. 2010; 33: 71-74.

Park SH, Choi SU, Lee CO, Yoo SE, Yoon SK, Kim YK, Ryu SY. Costunolide, a sesquiterpene from the stem bark of Magnolia sieboldii, inhibits the RAS-farnesyl-proteintransferase. Planta Med. 2001b; 67: 358-59.

Rasul A, Yu B, Yang L, Arshad M, Khan M, Ma T, Yang H. Costunolide, a sesquiterpene lactone, induces G2/M phase arrest and mitochondria-mediated apoptosis in human gastric adenocarcinoma SGC-7901 cells. J Med Plants Res. 2011; 6: 1191-200.

Song XK, Tu PF, Wu LJ, Cai Y, Zhu H, Lu Y, Liu XY, Zheng QT. A new sesquiterpene lactone from Tsoongiodendron odorum Chun. J Asian Nat Prod Res. 2001; 3: 285-91.

Srivastava SK, Abraham A, Bhat B, Jaggi M, Singh AT, Sanna VK, Singh G, Agarwal SK, Mukherjee R, Burman AC. Synthesis of 13-amino costunolide derivatives as anticancer agents. Bioorg Med Chem Lett. 2006; 16: 4195-99.

Stefani R, Schorr K, Tureta JM, Vichnewski W, Merfort I, da Costa FB. Sesquiterpene lactones from Dimerostemma species (Asteraceae) and in vitro potential anti-inflammatory activities. Z Naturforsch C 2006; 61: 647-52.

Sun CM, Syu WJ, Don MJ, Lu JJ, Lee GH. Cytotoxic sesquiterpene lactones from the root of Saussurea lappa. J Nat Prod. 2003; 66: 1175-80.

Taylor WR, Stark GR. Regulation of the G2/M transition by p53. Oncogene 2001; 20: 1803-15.

Wedge DE, Galindo JC, Macias FA. Fungicidal activity of natural and synthetic sesquiterpene lactone analogs. Phytochemistry 2000; 53: 747-57.

Woynarowski JM, Napier C, Koester SK, Chen SF, Troyer D, Chapman W, MacDonald JR. Effects on DNA integrity and apoptosis induction by a novel antitumor sesquiterpene drug, 6-hydroxymethylacylfulvene (HMAF, MGI 114). Biochem Pharmacol. 1997; 54: 1181-93.

Wu SH, Luo XD, Ma YB, Hao XJ, Zhou J, Wu DG. Two new germacranolides from Magnolia grandiflora. J Asian Nat Prod Res. 2001; 3: 95-102.

Yang NY, Duan JA, Shang EX, Tian LJ. Analysis of sesquiterpene lactones in Eupatorium lindleyanum by HPLC-PDA-ESI-MS/MS. Phytochem Anal. 2010; 21: 144-49.

Yang YI, Kim JH, Lee KT, Choi JH. Costunolide induces apoptosis in platinum-resistant human ovarian cancer cells by generating reactive oxygen species. Gynecol Oncol. 2011; 123: 588-96.

Zhang Q, Cai D, Liu J. Matrix solid-phase dispersion extraction coupled with HPLC-diode array detection method for the analysis of sesquiterpene lactones in root of Saussurea lappa C.B. Clarke. J Chromatogr B Analyt Technol Biomed Life Sci. 2011; 879: 2809-14.

Zhang S, Won YK, Ong CN, Shen HM. Anti-cancer potential of sesquiterpene lactones: Bioactivity and molecular mechanisms. Curr Med Chem Anticancer Agents. 2005; 5: 239-49.

Downloads

Published

2012-03-11

How to Cite

Rasul, A., S. Parveen, and T. Ma. “Costunolide: A Novel Anti-Cancer Sesquiterpene Lactone”. Bangladesh Journal of Pharmacology, vol. 7, no. 1, Mar. 2012, pp. 6-13, doi:10.3329/bjp.v7i1.10066.

Issue

Section

Mini Review