4-Hydroxylonchocarpin
(Synonyms: 异补骨脂色烯查耳酮) 目录号 : GC35132
4-Hydroxylonchocarpin 是一种查尔酮化合物，来自补骨脂 (Psoralea corylifolia) 提取物。4-Hydroxylonchocarpin 增强 p38 MAPK，JNK 和 ERK 的磷酸化。4-Hydroxylonchocarpin 具有多种药理活性，包括抗菌，抗癌，抗逆转录酶，抗结核，抗疟，抗炎和抗氧化活性。
Cas No.:56083-03-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
4-Hydroxylonchocarpin is a chalcone compound from an extract of Psoralea corylifolia. 4-Hydroxylonchocarpin increases phosphorylation of p38 MAPK, JNK and ERK. 4-Hydroxylonchocarpin has diverse pharmacological activities, including antibacterial, antifungal, anticancer, antireverse transcriptase, antitubercular, antimalarial, anti-inflammatory and antioxidant activities[1].
[1]. Lim J, et al. Antimelanogenic effect of 4-hydroxylonchocarpin through the inhibition of tyrosinase-related proteins and MAPK phosphatase. Exp Dermatol. 2016 Jul;25(7):574-6.
| Cas No. | 56083-03-5 | SDF | |
| 别名 | 异补骨脂色烯查耳酮 | ||
| Canonical SMILES | O=C(C1=CC=C2C(C=CC(C)(C)O2)=C1O)/C=C/C3=CC=C(O)C=C3.[(E)] | ||
| 分子式 | C20H18O4 | 分子量 | 322.35 |
| 溶解度 | DMSO : 50 mg/mL (155.11 mM; Need ultrasonic) | 储存条件 | 4°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 | 3.1022 mL | 15.5111 mL | 31.0222 mL |
| 5 mM | 0.6204 mL | 3.1022 mL | 6.2044 mL |
| 10 mM | 0.3102 mL | 1.5511 mL | 3.1022 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。
Chemistry and pharmacology of 4-Hydroxylonchocarpin: a review
Chin J Integr Med 2013 Jun;19(6):475-80.PMID:23784469DOI:10.1007/s11655-013-1195-7.
4-Hydroxylonchocarpin (LCP) or 2',4-dihydroxy-3',4'-(2,2-dimethylchromene) chalcone is a chalcone of the class flavonoid, with a molecular weight of 322 g/mol mostly isolated in the family Moraceae and Leguminosae. LCP was reported to have a variety of pharmacological activities such as antibacterial, antifungal, anticancer, anti-reverse transcriptase, antitubercular, antimalarial, anti-inflammatory, ornitnine decarboxylase activity and antioxidant. The hemisynthesis of the compound has been described. The present review was undertaken to bring out together the knowledge on LCP, and can serve as the start point for future research and valorization accomplishments.
Cytotoxic flavonoids from two Lonchocarpus species
Nat Prod Res 2019 Sep;33(18):2609-2617.PMID:29656660DOI:10.1080/14786419.2018.1462179.
A new isoflavone, 4'-prenyloxyvigvexin A (1) and a new pterocarpan, (6aR,11aR)-3,8-dimethoxybitucarpin B (2) were isolated from the leaves of Lonchocarpus bussei and the stem bark of Lonchocarpus eriocalyx, respectively. The extract of L. bussei also gave four known isoflavones, maximaisoflavone H, 7,2'-dimethoxy-3',4'-methylenedioxyisoflavone, 6,7,3'-trimethoxy-4',5'-methylenedioxyisoflavone, durmillone; a chalcone, 4-Hydroxylonchocarpin; a geranylated phenylpropanol, colenemol; and two known pterocarpans, (6aR,11aR)-maackiain and (6aR,11aR)-edunol. (6aR,11aR)-Edunol was also isolated from the stem bark of L. eriocalyx. The structures of the isolated compounds were elucidated by spectroscopy. The cytotoxicity of the compounds was tested by resazurin assay using drug-sensitive and multidrug-resistant cancer cell lines. Significant antiproliferative effects with IC50 values below 10 μM were observed for the isoflavones 6,7,3'-trimethoxy-4',5'-methylenedioxyisoflavone and durmillone against leukemia CCRF-CEM cells; for the chalcone, 4-Hydroxylonchocarpin and durmillone against its resistant counterpart CEM/ADR5000 cells; as well as for durmillone against the resistant breast adenocarcinoma MDA-MB231/BCRP cells and resistant gliobastoma U87MG.ΔEGFR cells.
Cytotoxicity and mode of action of four naturally occuring flavonoids from the genus Dorstenia: gancaonin Q, 4-Hydroxylonchocarpin, 6-prenylapigenin, and 6,8-diprenyleriodictyol
Planta Med 2011 Dec;77(18):1984-9.PMID:21800276DOI:10.1055/s-0031-1280023.
Several flavonoid-like compounds were found to possess good antiproliferative properties. Herein, we examined the ability of four naturally occuring and biologically active flavonoids from the genus Dorstenia, gancaonin Q (1), 6-prenylapigenin (2), 6,8-diprenyleriodictyol (3), and 4-Hydroxylonchocarpin ( 4), to inhibit the proliferation of a panel of fourteen cancer cell lines including leukemia and solid cancer cells, as well as AML12 normal hepatocytes. The study was extended to the analysis of cell cycle distribution, apoptosis induction, and caspase 3/7 activity and the antiangiogenic properties of the four compounds. The results of the cytotoxicity assays showed that more than 50 % inhibition of proliferation was obtained with compound 1 on all the fourteen studied cancer cell lines, with IC (50) values below 20 µg/mL. Compounds 2, 4, and 3 showed selective activity, with IC (50) values below 20 µg/mL being noted on 57.15 %, 71.42 %, and 85.71 % of the fourteen cancer cell lines, respectively. None of the compounds exhibited more than 50 % inhibition against AML12 normal hepatocytes cells at 20 µg/mL. IC (50) values below or around 4 µg/mL were recorded on 28.57 % of the tested cell lines for both compound 1 and 4 and 21.43 % for compound 3, which appeared to be the best cytotoxic compounds. This study indicates that caspase 3/7 activation is one of the modes of induction of apoptosis for compounds 1, 3, and 4 in CCRF-CEM cells. The results of the antiangiogenic assay indicated that compounds 1, 3, and 4 were also able to inhibit the growth of blood capillaries on the chorioallantoic membrane of quail eggs, the best effect being noted for compound 4 (54.1 % inhibition). The results of the present work provide evidence of the cytotoxic potential of the four studied flavonoids and supportive data for further investigations.
Millettia pachycarpa exhibits anti-inflammatory activity through the suppression of LPS-induced NO/iNOS expression
Am J Chin Med 2014;42(4):949-65.PMID:25004885DOI:10.1142/S0192415X14500608.
The present study was designed to investigate the in vitro and in vivo anti-inflammatory activity of flavonoids isolated from Millettia pachycarpa Benth. The seeds of M. pachycarpa Benth were extracted with ethanol and subjected to chromatographic separation for the isolation of bioactive compounds. Their structures were elucidated by spectroscopic methods. The anti-inflammatory activity of the compounds was investigated by evaluating the inhibition ability of NO production, iNOS activity and iNOS protein expression induced by LPS-stimulated RAW264.7 macrophages in vitro and the carrageenan-induced hind paw edema model in vivo. Molecular docking simulation was also employed to obtain the binding parameters in the binding pocket of iNOS. Thirteen compounds (1-13) were isolated from Chinese herbal medicine M. pachycarpa Benth. Among them, 4-Hydroxylonchocarpin (6) and deguelin (7) exhibited remarkable inhibitory rates of 66.5% and 57.7%, respectively, compared with that of 52.5% of indomethacin in LPS-induced macrophages cells. 4-Hydroxylonchocarpin (6) with low toxicity (IC50 > 100 μm) exhibited better inhibitory effects to positive control of 1400W on iNOS activity at the concentration of 10 μm. Western blot assay revealed that 4-Hydroxylonchocarpin (6) inhibited iNOS protein expression in RAW264.7 cells and molecular docking simulation showed that 4-Hydroxylonchocarpin (6) fit well into the binding pocket of iNOS. In the carrageenan-induced paw edema model, our data revealed that the anti-inflammatory potential of 4-Hydroxylonchocarpin (6) at 10 mg/kg showed comparable inhibitory ability to indomethacin at 5 h while a higher concentration of 4-Hydroxylonchocarpin (6) at 50 mg/kg showed higher inhibitory activity than indomethacin, which was further confirmed by plasma levels of nitrite. The overall results suggest that 4-Hydroxylonchocarpin (6) might be used as a potential therapeutic agent for inflammation-associated disorders.
Chalcones and other constituents of Dorstenia prorepens and Dorstenia zenkeri
Phytochemistry 2002 Apr;59(8):877-83.PMID:11937170DOI:10.1016/s0031-9422(01)00483-6.
The twigs of Dorstenia prorepens furnished the digeranylated chalcone, 5,3'-(3,7-dimethyl-2,6-octadienyl)-3,4, 2',4'-tetrahydroxychalcone while Dorstenia zenkeri yielded the 3',4'-(3-hydroxy-2,2-dimethyldihydropyrano)-4,2'-dihydroxychalcone and a bichalcone. 4-Hydroxylonchocarpin was found in both plants. D. prorepens also yielded the known compounds: psoralen, bergapten, beta-sitosterol and its D-glucopyranosyl derivative. D. zenkeri yielded p-hydroxybenzaldehyde, dorsmanin A, 4,2',4'-trihydroxychalcone and 4,2',4'-trihydroxy-3'-prenylchalcone. Structures of the new compounds were established by UV, IR, MS and 2-D NMR analysis.