4'-Demethylpodophyllotoxin
(Synonyms: 4'-去甲基鬼臼毒素) 目录号 : GC35129
A lignan with microtubule assembly inhibitory and anticancer activities
Cas No.:40505-27-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
4'-Demethylpodophyllotoxin is a lignan that has been found in D. versipellis and has microtubule assembly inhibitory and anticancer activities.1,2 It inhibits the assembly of isolated chicken brain tubulin (IC50 = 0.5 ?M) and the proliferation of LNCaP and PC3 prostate cancer cells (IC50s = 0.056 and 0.082 ?M, respectively).
1.Loike, J.D., Brewer, C.F., Sternlicht, H., et al.Structure-activity study of the inhibition of microtubule assembly in vitro by podophyllotoxin and its congenersCancer Res.38(9)2688-2693(1978) 2.Jiang, R.-W., Zhou, J.-R., Hon, P.-M., et al.Lignans from Dysosma versipellis with inhibitory effects on prostate cancer cell linesJ. Nat. Prod.70(2)283-286(2007)
| Cas No. | 40505-27-9 | SDF | |
| 别名 | 4'-去甲基鬼臼毒素 | ||
| Canonical SMILES | O=C1[C@]2([H])[C@H](C3=CC(OC)=C(O)C(OC)=C3)C(C=C(OCO4)C4=C5)=C5[C@H](O)[C@@]2([H])CO1 | ||
| 分子式 | C21H20O8 | 分子量 | 400.38 |
| 溶解度 | DMSO: 250 mg/mL (624.41 mM) | 储存条件 | Store at -20°C |
| 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 | 2.4976 mL | 12.4881 mL | 24.9763 mL |
| 5 mM | 0.4995 mL | 2.4976 mL | 4.9953 mL |
| 10 mM | 0.2498 mL | 1.2488 mL | 2.4976 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。
Ultrahigh pressure extraction of lignan compounds from Dysosma versipellis and purification by high-speed counter-current chromatography
J Chromatogr B Analyt Technol Biomed Life Sci 2012 Sep 15;905:145-9.PMID:22939268DOI:10.1016/j.jchromb.2012.08.016.
Ultrahigh pressure extraction (UPE) was employed to extract podophyllotoxin and 4'-Demethylpodophyllotoxin from Dysosma versipellis. The effects of extraction parameters including extraction solvents, pressure, time and solid/liquid ratio were investigated using a High Hydrostatic Pressure Processor. The optimal condition for UPE of the target compounds was 80% methanol, 200 MPa of pressure, 1 min of extraction time and 1:12 (g/mL) of solid/liquid ratio. Podophyllotoxin and 4'-Demethylpodophyllotoxin in the crude extract were purified by high-speed counter-current chromatography (HSCCC) with a two-phase solvent system composed of petroleum ether-ethyl acetate-methanol-water (10:10:8:12, v/v), and the fractions were analyzed by HPLC, ESI-MS and (1)H NMR. As a result, 73.7 mg podophyllotoxin and 16.5mg 4'-Demethylpodophyllotoxin with purities over 96% were obtained from 260 mg crude sample in one-step separation.
Liver-protective actions of desoxypodophyllotoxin and its analogs
J Pharmacobiodyn 1982 Aug;5(8):638-41.PMID:7153836DOI:10.1248/bpb1978.5.638.
Effects on CCl(4)-induced liver lesion in mice and on D-galactosamine-induced liver lesion in rats of desoxypodophyllotoxin (1) and its analogs, podophyllotoxin (2), podophyllotoxon (3), beta-peltatin (4), alpha-peltatin (5), 4'-Demethylpodophyllotoxin (6) and picropodophyllin (7), were investigated. 1 and 7 in CCl(4)-induced liver lesion and 1,4,5, and 6 in D-galactosamine-induced liver lesion have shown marked protective actions. These results suggest that these analogs have liver-protective actions in general and the substituents at C-4 in ring C, C-5 in ring B and C-4' in ring E, and the configuration at C-2 in ring C are important for the revelation of the activity.
[Dynamic study on two lignans contents in different parts of Sinopodophyllum hexandrum]
Zhongguo Zhong Yao Za Zhi 2015 May;40(9):1837-41.PMID:26323159doi
The contents of two lignans, namely 4'-Demethylpodophyllotoxin and podophyllotoxin in cultivated and wild Sinopodophyllum hexandrum plants were extracted by ultrasonicaction and determined by HPLC. According to the result showed, the order of parts of cultivated plants containing 4'-Demethylpodophyllotoxin from high to low is as follows: stem > root, no 4'-demethypodophyllotoxin was detected in leaves of cultivated plants; The order of parts of wild plants 4'-Demethylpodophyllotoxin from high to low is as follows: lateral root > petiole > rhizome > leaf, no 4'-demethypodophyllotoxin was detected in fruit. The order of parts of cultivated and wild S. hexandrum containing podophyllotoxin from high to low is as follows: root > petiole > leaf ( > fruit). Both of the lignan contents in different parts of cultivated plant varied in a " W" curve with the changes in seasons, with the highest content in July.
Antileishmanial and cytotoxic compounds from Valeriana wallichii and identification of a novel nepetolactone derivative
Molecules 2015 Apr 1;20(4):5740-53.PMID:25834987DOI:10.3390/molecules20045740.
The chloroform extract of Valeriana wallichii (V. wallichii) rhizomes was investigated to elucidate the structures responsible for reported antileishmanial activity. Besides bornyl caffeate (1, already been reported by us previously), bioassay-guided fractionation resulted in two additional cinnamic acid derivatives 2-3 with moderate leishmanicidal activity. The structure of a novel nepetolactone derivative 4 having a cinnamic acid moiety was elucidated by means of spectral analysis. To the best of our knowledge villoside aglycone (5) was isolated from this plant for the first time. The bioassay-guided fractionation yielded two new (compounds 6-7) and two known valtrates (compounds 8-9) with leishmanicidal potential against Leishmania major (L. major) promastigotes. In addition, β-bisabolol (10), α-kessyl alcohol (11), valeranone (12), bornyl isovalerate (13) and linarin-2-O-methylbutyrate (14) were identified. This is the first report on the isolation of 4'-Demethylpodophyllotoxin (15), podophyllotoxin (16) and pinoresinol (17) in V. wallichii. In total thirteen known and four new compounds were identified from the extract and their cytotoxic and antileishmanial properties were evaluated.
Simultaneous determination of three major lignans in rat plasma by LC-MS/MS and its application to a pharmacokinetic study after oral administration of Diphylleia sinensis extract
Biomed Chromatogr 2014 Apr;28(4):463-7.PMID:24122912DOI:10.1002/bmc.3066.
A sensitive and selective liquid chromatography tandem mass spectrometry was developed and validated for the simultaneous determination of three major lignans (podophyllotoxin, epipodophyllotoxin, and 4'-Demethylpodophyllotoxin) in rat plasma using diphenhydramine as the internal standard. The analytes were detected using a triple quadrupole mass spectrometer that was equipped with an electrospray ionization source in the positive ion and selected reaction monitoring modes. The linearity of the calibration curve was good, with coefficients of determination (r(2) ) >0.9914 for all of the analytes. The developed method was successfully applied for the simultaneous determination of the three lignans in rat plasma following oral administration of Diphylleia sinensis extract to rats.