Costunolide
Costunolide, also known as (+)-Costunolide, CCRIS 6754 and NSC 106404, is a naturally occurring sesquiterpene lactone, first isolated in Saussurea costus roots in 1960. It is also found in lettuce. Costunolide has been reported for the wide spectrum of biological effects, including anti-inflammatory, anticancer, antiviral, antimicrobial, antifungal, antioxidant, antidiabetic, antiulcer, and anthelmintic activities. In recent years, it have caused extensive interest in researchers due to its potential anti-cancer activities for various types of cancer, and their anti-cancer mechanisms, including causing cell cycle arrest, inducing apoptosis and differentiation, promoting the aggregation of microtubule protein, inhibiting the activity of telomerase, inhibiting metastasis and invasion, reversing multidrug resistance, restraining angiogenesis has been studied.
1: Pavan Kumar C, Devi A, Ashok Yadav P, Rao Vadaparthi R, Shankaraiah G, Sowjanya P, Jain N, Suresh Babu K. "Click" reaction mediated synthesis of costunolide and dehydrocostuslactone derivatives and evaluation of their cytotoxic activity. J Asian Nat Prod Res. 2016 Jun 22:1-16. [Epub ahead of print] PubMed PMID: 27329166.
2: Zhang C, Lu T, Wang GD, Ma C, Zhou YF. Costunolide, an active sesquiterpene lactone, induced apoptosis via ROS-mediated ER stress and JNK pathway in human U2OS cells. Biomed Pharmacother. 2016 May;80:253-9. doi: 10.1016/j.biopha.2016.03.031. Epub 2016 Apr 1. PubMed PMID: 27133064.
3: Hua P, Sun M, Zhang G, Zhang Y, Song G, Liu Z, Li X, Zhang X, Li B. Costunolide Induces Apoptosis through Generation of ROS and Activation of P53 in Human Esophageal Cancer Eca-109 Cells. J Biochem Mol Toxicol. 2016 Apr 14. doi: 10.1002/jbt.21810. [Epub ahead of print] PubMed PMID: 27078502.
4: Hua P, Zhang G, Zhang Y, Sun M, Cui R, Li X, Li B, Zhang X. Costunolide induces G1/S phase arrest and activates mitochondrial-mediated apoptotic pathways in SK-MES 1 human lung squamous carcinoma cells. Oncol Lett. 2016 Apr;11(4):2780-2786. Epub 2016 Mar 1. PubMed PMID: 27073552; PubMed Central PMCID: PMC4812560.
5: Zheng H, Chen Y, Zhang J, Wang L, Jin Z, Huang H, Man S, Gao W. Evaluation of protective effects of costunolide and dehydrocostuslactone on ethanol-induced gastric ulcer in mice based on multi-pathway regulation. Chem Biol Interact. 2016 Apr 25;250:68-77. doi: 10.1016/j.cbi.2016.03.003. Epub 2016 Mar 10. PubMed PMID: 26970604.
6: Wang Z, Zhao X, Gong X. Costunolide induces lung adenocarcinoma cell line A549 cells apoptosis through ROS (reactive oxygen species)-mediated endoplasmic reticulum stress. Cell Biol Int. 2016 Mar;40(3):289-97. doi: 10.1002/cbin.10564. Epub 2016 Jan 21. PubMed PMID: 26609913.
7: Zhang JZ, Wang L, Jin ZX, Qu Z, Chen YL, Gao WY. [Pharmacokinetics study on costunolide and dehydrocostuslactone after administration of traditional Chinese medicine Weichang'an pills]. Zhongguo Zhong Yao Za Zhi. 2015 Mar;40(6):1173-8. Chinese. PubMed PMID: 26226766.
8: Yang ZJ, Ge WZ, Li QY, Lu Y, Gong JM, Kuang BJ, Xi X, Wu H, Zhang Q, Chen Y. Syntheses and Biological Evaluation of Costunolide, Parthenolide, and Their Fluorinated Analogues. J Med Chem. 2015 Sep 10;58(17):7007-20. doi: 10.1021/acs.jmedchem.5b00915. Epub 2015 Aug 20. PubMed PMID: 26226279.
9: Roy A, Manikkam R. Cytotoxic Impact of Costunolide Isolated from Costus speciosus on Breast Cancer via Differential Regulation of Cell Cycle-An In-vitro and In-silico Approach. Phytother Res. 2015 Oct;29(10):1532-9. doi: 10.1002/ptr.5408. Epub 2015 Jul 14. PubMed PMID: 26178525.
10: Lin X, Peng Z, Su C. Potential anti-cancer activities and mechanisms of costunolide and dehydrocostuslactone. Int J Mol Sci. 2015 May 13;16(5):10888-906. doi: 10.3390/ijms160510888. Review. PubMed PMID: 25984608; PubMed Central PMCID: PMC4463681.
11: Rao Vadaparthi PR, Kumar K, Sarma VU, Hussain QA, Babu KS. Estimation of Costunolide and Dehydrocostus Lactone in Saussurea lappa and its Polyherbal Formulations followed by their Stability Studies Using HPLC-DAD. Pharmacogn Mag. 2015 Jan-Mar;11(41):180-90. doi: 10.4103/0973-1296.149736. PubMed PMID: 25709231; PubMed Central PMCID: PMC4329622.
12: Yin H, Zhuang YB, Li EE, Bi HP, Zhou W, Liu T. Heterologous biosynthesis of costunolide in Escherichia coli and yield improvement. Biotechnol Lett. 2015 Jun;37(6):1249-55. doi: 10.1007/s10529-015-1784-6. Epub 2015 Feb 21. PubMed PMID: 25700819.
13: Dong GZ, Shim AR, Hyeon JS, Lee HJ, Ryu JH. Inhibition of Wnt/β-Catenin Pathway by Dehydrocostus Lactone and Costunolide in Colon Cancer Cells. Phytother Res. 2015 May;29(5):680-6. doi: 10.1002/ptr.5299. Epub 2015 Jan 27. PubMed PMID: 25625870.
14: Scarponi C, Butturini E, Sestito R, Madonna S, Cavani A, Mariotto S, Albanesi C. Inhibition of inflammatory and proliferative responses of human keratinocytes exposed to the sesquiterpene lactones dehydrocostuslactone and costunolide. PLoS One. 2014 Sep 16;9(9):e107904. doi: 10.1371/journal.pone.0107904. eCollection 2014. PubMed PMID: 25226283; PubMed Central PMCID: PMC4166670.
15: Peng Z, Wang Y, Gu X, Guo X, Yan C. Study on the pharmacokinetics and metabolism of costunolide and dehydrocostus lactone in rats by HPLC-UV and UPLC-Q-TOF/MS. Biomed Chromatogr. 2014 Oct;28(10):1325-34. doi: 10.1002/bmc.3167. Epub 2014 Jun 2. PubMed PMID: 24889523.
16: Pitchai D, Roy A, Banu S. In vitro and in silico evaluation of NF-κB targeted costunolide action on estrogen receptor-negative breast cancer cells--a comparison with normal breast cells. Phytother Res. 2014 Oct;28(10):1499-505. doi: 10.1002/ptr.5155. Epub 2014 Apr 15. PubMed PMID: 24733523.
17: Butturini E, Di Paola R, Suzuki H, Paterniti I, Ahmad A, Mariotto S, Cuzzocrea S. Costunolide and Dehydrocostuslactone, two natural sesquiterpene lactones, ameliorate the inflammatory process associated to experimental pleurisy in mice. Eur J Pharmacol. 2014 May 5;730:107-15. doi: 10.1016/j.ejphar.2014.02.031. Epub 2014 Mar 10. PubMed PMID: 24625594.
18: Zhang J, Hu X, Gao W, Qu Z, Guo H, Liu Z, Liu C. Pharmacokinetic study on costunolide and dehydrocostuslactone after oral administration of traditional medicine Aucklandia lappa Decne. by LC/MS/MS. J Ethnopharmacol. 2014;151(1):191-7. doi: 10.1016/j.jep.2013.10.024. Epub 2013 Nov 8. PubMed PMID: 24216164.
19: Whipple RA, Vitolo MI, Boggs AE, Charpentier MS, Thompson K, Martin SS. Parthenolide and costunolide reduce microtentacles and tumor cell attachment by selectively targeting detyrosinated tubulin independent from NF-κB inhibition. Breast Cancer Res. 2013;15(5):R83. PubMed PMID: 24028602; PubMed Central PMCID: PMC3979133.
20: Choi YK, Cho SG, Woo SM, Yun YJ, Jo J, Kim W, Shin YC, Ko SG. Saussurea lappa Clarke-Derived Costunolide Prevents TNF α -Induced Breast Cancer Cell Migration and Invasion by Inhibiting NF- κ B Activity. Evid Based Complement Alternat Med. 2013;2013:936257. doi: 10.1155/2013/936257. Epub 2013 Aug 13. PubMed PMID: 23997800; PubMed Central PMCID: PMC3755433.
2: Zhang C, Lu T, Wang GD, Ma C, Zhou YF. Costunolide, an active sesquiterpene lactone, induced apoptosis via ROS-mediated ER stress and JNK pathway in human U2OS cells. Biomed Pharmacother. 2016 May;80:253-9. doi: 10.1016/j.biopha.2016.03.031. Epub 2016 Apr 1. PubMed PMID: 27133064.
3: Hua P, Sun M, Zhang G, Zhang Y, Song G, Liu Z, Li X, Zhang X, Li B. Costunolide Induces Apoptosis through Generation of ROS and Activation of P53 in Human Esophageal Cancer Eca-109 Cells. J Biochem Mol Toxicol. 2016 Apr 14. doi: 10.1002/jbt.21810. [Epub ahead of print] PubMed PMID: 27078502.
4: Hua P, Zhang G, Zhang Y, Sun M, Cui R, Li X, Li B, Zhang X. Costunolide induces G1/S phase arrest and activates mitochondrial-mediated apoptotic pathways in SK-MES 1 human lung squamous carcinoma cells. Oncol Lett. 2016 Apr;11(4):2780-2786. Epub 2016 Mar 1. PubMed PMID: 27073552; PubMed Central PMCID: PMC4812560.
5: Zheng H, Chen Y, Zhang J, Wang L, Jin Z, Huang H, Man S, Gao W. Evaluation of protective effects of costunolide and dehydrocostuslactone on ethanol-induced gastric ulcer in mice based on multi-pathway regulation. Chem Biol Interact. 2016 Apr 25;250:68-77. doi: 10.1016/j.cbi.2016.03.003. Epub 2016 Mar 10. PubMed PMID: 26970604.
6: Wang Z, Zhao X, Gong X. Costunolide induces lung adenocarcinoma cell line A549 cells apoptosis through ROS (reactive oxygen species)-mediated endoplasmic reticulum stress. Cell Biol Int. 2016 Mar;40(3):289-97. doi: 10.1002/cbin.10564. Epub 2016 Jan 21. PubMed PMID: 26609913.
7: Zhang JZ, Wang L, Jin ZX, Qu Z, Chen YL, Gao WY. [Pharmacokinetics study on costunolide and dehydrocostuslactone after administration of traditional Chinese medicine Weichang'an pills]. Zhongguo Zhong Yao Za Zhi. 2015 Mar;40(6):1173-8. Chinese. PubMed PMID: 26226766.
8: Yang ZJ, Ge WZ, Li QY, Lu Y, Gong JM, Kuang BJ, Xi X, Wu H, Zhang Q, Chen Y. Syntheses and Biological Evaluation of Costunolide, Parthenolide, and Their Fluorinated Analogues. J Med Chem. 2015 Sep 10;58(17):7007-20. doi: 10.1021/acs.jmedchem.5b00915. Epub 2015 Aug 20. PubMed PMID: 26226279.
9: Roy A, Manikkam R. Cytotoxic Impact of Costunolide Isolated from Costus speciosus on Breast Cancer via Differential Regulation of Cell Cycle-An In-vitro and In-silico Approach. Phytother Res. 2015 Oct;29(10):1532-9. doi: 10.1002/ptr.5408. Epub 2015 Jul 14. PubMed PMID: 26178525.
10: Lin X, Peng Z, Su C. Potential anti-cancer activities and mechanisms of costunolide and dehydrocostuslactone. Int J Mol Sci. 2015 May 13;16(5):10888-906. doi: 10.3390/ijms160510888. Review. PubMed PMID: 25984608; PubMed Central PMCID: PMC4463681.
11: Rao Vadaparthi PR, Kumar K, Sarma VU, Hussain QA, Babu KS. Estimation of Costunolide and Dehydrocostus Lactone in Saussurea lappa and its Polyherbal Formulations followed by their Stability Studies Using HPLC-DAD. Pharmacogn Mag. 2015 Jan-Mar;11(41):180-90. doi: 10.4103/0973-1296.149736. PubMed PMID: 25709231; PubMed Central PMCID: PMC4329622.
12: Yin H, Zhuang YB, Li EE, Bi HP, Zhou W, Liu T. Heterologous biosynthesis of costunolide in Escherichia coli and yield improvement. Biotechnol Lett. 2015 Jun;37(6):1249-55. doi: 10.1007/s10529-015-1784-6. Epub 2015 Feb 21. PubMed PMID: 25700819.
13: Dong GZ, Shim AR, Hyeon JS, Lee HJ, Ryu JH. Inhibition of Wnt/β-Catenin Pathway by Dehydrocostus Lactone and Costunolide in Colon Cancer Cells. Phytother Res. 2015 May;29(5):680-6. doi: 10.1002/ptr.5299. Epub 2015 Jan 27. PubMed PMID: 25625870.
14: Scarponi C, Butturini E, Sestito R, Madonna S, Cavani A, Mariotto S, Albanesi C. Inhibition of inflammatory and proliferative responses of human keratinocytes exposed to the sesquiterpene lactones dehydrocostuslactone and costunolide. PLoS One. 2014 Sep 16;9(9):e107904. doi: 10.1371/journal.pone.0107904. eCollection 2014. PubMed PMID: 25226283; PubMed Central PMCID: PMC4166670.
15: Peng Z, Wang Y, Gu X, Guo X, Yan C. Study on the pharmacokinetics and metabolism of costunolide and dehydrocostus lactone in rats by HPLC-UV and UPLC-Q-TOF/MS. Biomed Chromatogr. 2014 Oct;28(10):1325-34. doi: 10.1002/bmc.3167. Epub 2014 Jun 2. PubMed PMID: 24889523.
16: Pitchai D, Roy A, Banu S. In vitro and in silico evaluation of NF-κB targeted costunolide action on estrogen receptor-negative breast cancer cells--a comparison with normal breast cells. Phytother Res. 2014 Oct;28(10):1499-505. doi: 10.1002/ptr.5155. Epub 2014 Apr 15. PubMed PMID: 24733523.
17: Butturini E, Di Paola R, Suzuki H, Paterniti I, Ahmad A, Mariotto S, Cuzzocrea S. Costunolide and Dehydrocostuslactone, two natural sesquiterpene lactones, ameliorate the inflammatory process associated to experimental pleurisy in mice. Eur J Pharmacol. 2014 May 5;730:107-15. doi: 10.1016/j.ejphar.2014.02.031. Epub 2014 Mar 10. PubMed PMID: 24625594.
18: Zhang J, Hu X, Gao W, Qu Z, Guo H, Liu Z, Liu C. Pharmacokinetic study on costunolide and dehydrocostuslactone after oral administration of traditional medicine Aucklandia lappa Decne. by LC/MS/MS. J Ethnopharmacol. 2014;151(1):191-7. doi: 10.1016/j.jep.2013.10.024. Epub 2013 Nov 8. PubMed PMID: 24216164.
19: Whipple RA, Vitolo MI, Boggs AE, Charpentier MS, Thompson K, Martin SS. Parthenolide and costunolide reduce microtentacles and tumor cell attachment by selectively targeting detyrosinated tubulin independent from NF-κB inhibition. Breast Cancer Res. 2013;15(5):R83. PubMed PMID: 24028602; PubMed Central PMCID: PMC3979133.
20: Choi YK, Cho SG, Woo SM, Yun YJ, Jo J, Kim W, Shin YC, Ko SG. Saussurea lappa Clarke-Derived Costunolide Prevents TNF α -Induced Breast Cancer Cell Migration and Invasion by Inhibiting NF- κ B Activity. Evid Based Complement Alternat Med. 2013;2013:936257. doi: 10.1155/2013/936257. Epub 2013 Aug 13. PubMed PMID: 23997800; PubMed Central PMCID: PMC3755433.
| Chemical | |
|---|---|
| CAS Num | 553-21-9 |
| Chemical Formula | C15H20O2 |
| Molecular Weight | 232.323 |
| IUPAC Chemical Name | (3aS,6E,10E,11aR)-6,10-dimethyl-3-methylene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one |
| Exact Mass | 232.1463 |
| Elemental Analysis | C, 77.55; H, 8.68; O, 13.77 |
| Synonym | CCRIS 6754; NSC 106404; Costunolide; Costus lactone; (+)-Costunolide. |
| Solubility | Soluble in DMSO |
| SMILES Code | O=C(O[C@@]1([H])[C@@]2([H])CC/C(C)=C/CC/C(C)=C/1)C2=C |
| Biological | |
| Targets and Effects | N/A |
| Pathways | Apoptosis |
| Physical | |
| Appearance | Solid powder |
| Purity | >98% (or refer to the Certificate of Analysis) |
| Shipping Condition | Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs. |
| Storage Condition | Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). |
| Shelf Life | >2 years if stored properly |
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