Name | Costunolide |
Synonyms | costunolid Costunolide COSTUNOLIDE Saussurea lappa Saussurea costus Costundide 553-21-9 Costunolide (NSC-106404) (e,e)-6-alpha-hydroxygermacra-1(10),4,11(13)-trien-12-oicacidgamma-lactone germacra-1(10),4,11(13)-trien-12-oicacid,6-alpha-hydroxy-,gamma-lactone,(e, (3aS,10E,11aR)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one (3AS,6E,10E,11AR)-3A,4,5,8,9,11A-HEXAHYDRO-6,10-DIMETHYL-3-METHYLENE-CYCLODECA[B]FURAN-2(3H)-ONE (3aS,6Z,10E,11aR)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one (3aS,6E,10E,11aR)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one |
CAS | 553-21-9 |
InChI | InChI=1/C15H20O2/c1-10-5-4-6-11(2)9-14-13(8-7-10)12(3)15(16)17-14/h5,9,13-14H,3-4,6-8H2,1-2H3/b10-5u,11-9+/t13-,14+/m0/s1 |
InChIKey | HRYLQFBHBWLLLL-GRFSRWIASA-N |
Molecular Formula | C15H20O2 |
Molar Mass | 232.32 |
Density | 1.03±0.1 g/cm3(Predicted) |
Melting Point | 106-107 °C |
Boling Point | 385.4±42.0 °C(Predicted) |
Specific Rotation(α) | (c, 0.45 in CHCl3)+128 |
Flash Point | 162°C |
Solubility | Soluble in chloroform, ethyl acetate, acetone, insoluble in water. |
Vapor Presure | 3.8E-06mmHg at 25°C |
Appearance | White powder |
Color | white to beige |
Storage Condition | -20°C |
Refractive Index | 1.519 |
MDL | MFCD00210262 |
Physical and Chemical Properties | White crystalline powder, soluble in chloroform, derived from radix aucklandiae, Inula micranifica, radix gentianae Kerria japonica, Makino grass. |
In vitro study | Coatenolide inhibited MCF-7 and MDA-MB-231 telomerase activity and cell proliferation in a concentration-and time-dependent manner. Costellones also inhibited farnesyl protein transferase (FPTase)-induced farnesylation of human lamin-B in a dose-dependent manner. Continuous treatment of human tumor cells (A549, SK-OV-3, SK-MEL-2, XF498 and HCT-1) for 48 hours with Coplestone reduced cell proliferation in a dose-dependent manner. The induction of HL-60 apoptosis in human leukemia cells by copline lactone can be triggered by reactive oxygen species-mediated changes in mitochondrial permeability and the release of cytochrome C into the cytoplasm. A recent study has shown that copline lactone has significant antifungal activity, including Trichophyton (Trichophyton mentagrophytes), Trichophyton (T.simlii ), Trichophyton rubrum (T.rubrum) etc. |
In vivo study | Agarolide inhibits angiogenesis by blocking the vascular growth factor signaling pathway. In a mouse corneal microcapsule model, cotholone reduces neovascularization induced by VEGF. |
Hazard Symbols | Xi - Irritant |
Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S24/25 - Avoid contact with skin and eyes. |
WGK Germany | 3 |
HS Code | 29322090 |
Reference Show more | 1. WANG Huipin MENG Jie. Effect of 60Co-gamma ray irradiation sterilization on five effective components in Xiangsha Zhizhu pills [J]. Chinese Journal of Modern Applied Pharmacy, 2019, 036(003):336-340. 2. Han Yujia, Zhang, Peng, dailong. Pharmacodynamic screening of asthma dropping pills by different preparation processes [J]. Journal of Liaoning University of Traditional Chinese Medicine 2015 017(012):51-53. 3. Lin Xuejing, Liu Chunying, Peng zhangxiao, Sun Bin, Wu Mengchao, Su Chang Qing. Effect of auckyllactone on biological behavior of human cholangiocarcinoma RBE cells and its mechanism [J]. Chinese Journal of tumor Biotherapy, 2018,25(07):687-692. 4. Wang Guiming, Shi Dongdong, Peng zhangxiao, etc. Study on the mechanism of cocitrolactone-induced apoptosis in human breast cancer cell line MCF-7 [J]. Journal of Analytical Chemistry, 2015(05):682-688. 5. Ma Ruili, Li Jintian, Ma Guizhi. Establishment of HPLC fingerprint and determination of four components of zachong Shisanwei pills [J]. Chinese patent medicine, 2020, v.42(06):38-42. 6. Peng, Zhang Xiao, et al. "Costunolide and dehydrocostuslactone combination treatment inhibit breast cancer by inducing cell cycle arrest and apoptosis through c-Myc/p53 and AKT/14-3-3 pathway." Scientific reports 7.1 (2017): 1-16.https://doi.org/10.1038/sre 7. Peng, Z.-x., Wang, Y., Gu, X., Wen, Y.-y. and Yan, C. (2013) A platform for fast screening potential anti-breast cancer compounds in traditional Chinese medicines. Biomed. Chromatogr., 27: 1759-1766. https://doi.org/10.1002/bmc.2990 8. [IF=6.762] Caiping Tian et al."Multiplexed Thiol Reactivity Profiling for Target Discovery of Electrophilic Natural Products."Cell Chem Biol. 2017 Nov;24:1416 9. [IF=4.011] Zhangxiao Peng et al."Costunolide and dehydrocostuslactone combination treatment inhibit breast cancer by inducing cell cycle arrest and apoptosis through c-Myc/p53 and AKT/14-3-3 pathway."Sci Rep-Uk. 2017 Jan;7(1):1-16 10. [IF=1.902] Zhang-xiao Peng et al."A platform for fast screening potential anti-breast cancer compounds in traditional Chinese medicines."Biomed Chromatogr. 2013 Dec;27(12):1759-1766 |
NIST chemical information | information provided by: webbook.nist.gov (external link) |
biological activity | costagolide (NSC 106404) is a natural sesquiterpene compound with a variety of biological activities, the IC50 is 20 μm and also inhibits telomerase (telomerase) with an IC50 of 65-90 μm. |
Target | Value |
FPTase | 20 μM |
Telomerase (MDA-MB-231) | 65 μM |
Telomerase (MCF-7) | 90 μM |
Use | cofenolactone has both excitatory and inhibitory effects on the gastrointestinal tract. for content determination/identification/pharmacological experiments. Pharmacological Efficacy: has a significant choleretic effect, bronchial smooth muscle and small intestine smooth muscle has good spasmolytic effect. |