Isocurcumenol
(Synonyms: 异莪术烯醇) 目录号 : GC48900
A sesquiterpene with diverse biological activities
Cas No.:24063-71-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Isocurcumenol is a sesquiterpene that has been found in C. zedoaria rhizomes and has diverse biological activities.1,2,3 It inhibits mycelial growth of the plant pathogenic fungus F. graminearum when used at a concentration of 0.5 mg/ml.1 Isocurcumenol is cytotoxic to DLA, A549, KB, and K562 cancer cells (IC50s = 75.3, 75.7, 142.2, and 45.83 µg/ml, respectively).2 It inhibits LPS-induced production of nitric oxide (NO) in isolated mouse peritoneal macrophages.3 Isocurcumenol (50 mg/kg) reduces LPS/D-galactosamine-induced increases in serum levels of glutamic oxaloacetic transaminase (GOT) and glutamic pyruvic transaminase (GPT) in a mouse model of liver injury.
1.Chen, C., Long, L., Zhang, F., et al.Antifungal activity, main active components and mechanism of Curcuma longa extract against Fusarium graminearumPLoS One13(3)e0194284(2018) 2.Lakshmi, S., Padmaja, G., and Remani, P.Antitumour effects of isocurcumenol isolated from Curcuma zedoaria rhizomes on human and murine cancer cellsInt. J. Med. Chem.253962(2011) 3.Matsuda, H., Ninomiya, K., Morikawa, T., et al.Inhibitory effect and action mechanism of sesquiterpenes from zedoariae rhizoma on D-galactosamine/lipopolysaccharide-induced liver injuryBioorg. Med. Chem. Lett.8(4)339-344(1998)
| Cas No. | 24063-71-6 | SDF | |
| 别名 | 异莪术烯醇 | ||
| Canonical SMILES | C=C([C@@]1([H])[C@]([C@@H](C)CC1)(O2)C/3)C[C@]2(O)C3=C(C)/C | ||
| 分子式 | C15H22O2 | 分子量 | 234.3 |
| 溶解度 | DMF: 1 mg/ml,DMSO: 1 mg/ml,Ethanol: slightly soluble | 储存条件 | -20°C, protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 4.268 mL | 21.3402 mL | 42.6803 mL |
| 5 mM | 0.8536 mL | 4.268 mL | 8.5361 mL |
| 10 mM | 0.4268 mL | 2.134 mL | 4.268 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Antitumour Effects of Isocurcumenol Isolated from Curcuma zedoaria Rhizomes on Human and Murine Cancer Cells
Int J Med Chem 2011;2011:253962.PMID:27429805DOI:10.1155/2011/253962.
Curcuma zedoaria belonging to the family Zingiberaceae has been used in the traditional system of medicine in India and Southwest Asia in treating many human ailments and is found to possess many biological activities. The rationale of the present study was to isolate, identify, and characterize antitumour principles from the rhizomes of Curcuma zedoaria, to assess its cytotoxic effects on human and murine cancer cells, to determine its apoptosis inducing capacity in cancer cells, and to evaluate its tumour reducing properties in in vivo mice models. Isocurcumenol was characterized as the active compound by spectroscopy and was found to inhibit the proliferation of cancer cells without inducing significant toxicity to the normal cells. Fluorescent staining exhibited the morphological features of apoptosis in the compound-treated cancer cells. In vivo tumour reduction studies revealed that a dose of 35.7 mg/kg body weight significantly reduced the ascitic tumour in DLA-challenged mice and increased the lifespan with respect to untreated control mice.
Antifungal activity, main active components and mechanism of Curcuma longa extract against Fusarium graminearum
PLoS One 2018 Mar 15;13(3):e0194284.PMID:29543859DOI:10.1371/journal.pone.0194284.
Curcuma longa possesses powerful antifungal activity, as demonstrated in many studies. In this study, the antifungal spectrum of Curcuma longa alcohol extract was determined, and the resulting EC50 values (mg/mL) of its extract on eleven fungi, including Fusarium graminearum, Fusarium chlamydosporum, Alternaria alternate, Fusarium tricinctum, Sclerotinia sclerotiorum, Botrytis cinerea, Fusarium culmorum, Rhizopus oryzae, Cladosporium cladosporioides, Fusarium oxysporum and Colletotrichum higginsianum, were 0.1088, 0.1742, 0.1888, 0.2547, 0.3135, 0.3825, 0.4229, 1.2086, 4.5176, 3.8833 and 5.0183, respectively. Among them, F. graminearum was selected to determine the inhibitory effects of the compounds (including curdione, Isocurcumenol, curcumenol, curzerene, β-elemene, curcumin, germacrone and curcumol) derived from Curcuma longa. In addition, the antifungal activities of curdione, curcumenol, curzerene, curcumol and Isocurcumenol and the synergies of the complexes of curdione and seven other chemicals were investigated. Differential proteomics of F. graminearum was also compared, and at least 2021 reproducible protein spots were identified. Among these spots, 46 were classified as differentially expressed proteins, and these proteins are involved in energy metabolism, tRNA synthesis and glucose metabolism. Furthermore, several fungal physiological differences were also analysed. The antifungal effect included fungal cell membrane disruption and inhibition of ergosterol synthesis, respiration, succinate dehydrogenase (SDH) and NADH oxidase.
Cucurbituril and zwitterionic surfactant-based matrix solid-phase dispersion microextraction to simultaneously determine terpenoids from Radix Curcumae
J Sep Sci 2021 Apr;44(7):1361-1370.PMID:33432733DOI:10.1002/jssc.202001067.
A rapid, efficient, and environmentally friendly matrix solid-phase dispersion microextraction was established to determine and quantify terpenoids in Radix Curcumae using ultra-high-performance liquid chromatography with a diode array detector. Various parameters affecting the extraction were investigated in detail, such as the grinding time, amount of adsorbent, type and concentration of elution solvent, and pH. The optimization of single-factor and response surface methodology was performed to confirm the best conditions in this procedure. The final optimized conditions were obtained by applying 70 mg of cucurbituril as adsorbent, 149 s as the optimum grinding time, and 228 mM of 3-(N,N-dimethylpalmitylammonio)propanesulfonate aqueous solution (pH 6.5) as the optimal elution solvent. The validated method showed a satisfactory linear range of 0.10-10 µg/mL for curdione and furanodiene, 0.01-10 µg/mL for Isocurcumenol and germacrone, and 0.05-10 µg/mL for furanodienone, while the correlation coefficients ranged from 0.9945 to 0.9970. The recoveries of the investigated analytes at two spiked concentration levels (0.1 and 1.0 µg/mL) ranged from 96.53 to 104.60%. In addition, this method displayed acceptable reproducibility (relative standard deviation ≤ 3.66%). The results showed that the newly proposed matrix solid-phase dispersion microextraction method was successfully applied to analyze curdione, Isocurcumenol, furanodienone, germacrone and furanodiene in Radix Curcumae samples.
Modulation of radioligand binding to the GABA(A)-benzodiazepine receptor complex by a new component from Cyperus rotundus
Biol Pharm Bull 2002 Jan;25(1):128-30.PMID:11824542DOI:10.1248/bpb.25.128.
Four sesquiterpenes, beta-selinene, Isocurcumenol, nootkatone and aristolone and one triterpene, oleanolic acid were isolated from the ethylacetate fraction of the rhizomes of Cyperus rotundus and tested for their ability to modulate gamma-aminobutyric acid (GABA(A))-benzodiazepine receptor function by radioligand binding assays using rat cerebrocortical membranes. Among these compounds, only Isocurcumenol, one of the newly identified constituents of this plant, was found to inhibit [3H]Ro15-1788 binding and enhance [3H]flunitrazepam binding in the presence of GABA. These results suggest that Isocurcumenol may serve as a benzodiazepine receptor agonist and allosterically modulate GABAergic neurotransmission via enhancement of endogenous receptor ligand binding.
Bioactive sesquiterpenes from Curcuma ochrorhiza and Curcuma heyneana
Nat Prod Res 2010 May;24(9):838-45.PMID:20461629DOI:10.1080/14786410903052951.
Curcuma ochrorhiza ('temu putih') and C. heyneana ('temu giring') are two Zingiberaceous species which are commonly used in traditional medicine in Malaysia and Indonesia. Phytochemical investigations on these Curcuma species have resulted in the isolation of six sesquiterpenes, namely zerumbone (1), furanodienone (2), zederone (3), oxycurcumenol epoxide (4), curcumenol (5) and Isocurcumenol (6), along with phytosterols stigmasterol and alpha-sitosterol. Compounds 1 and 2 were obtained for the first time for C. ochrorhiza while 4 was new to C. heyneana. The hexane extract of C. ochrorhiza and sesquiterpenes 1 and 3 showed very strong cytotoxicity activity against T-acute lymphoblastic leukaemia cells (CEM-SS), with IC(50) values of 6.0, 0.6 and 1.6 microg mL(-1), respectively. Meanwhile, constituents from C. heyneana (4-6) demonstrated moderate inhibition against CEM-SS in cytotoxic assay, with IC(50) values of 11.9, 12.6 and 13.3 microg mL(-1), respectively. The crude extracts and sesquiterpenes isolated were moderately active against certain bacteria tested in antimicrobial screening.