Rapanone
(Synonyms: 拉帕酮) 目录号 : GC63860
Rapanone 是一种天然苯醌。Rapanone 具有广泛的生物作用，包括抗肿瘤、抗氧化、抗炎、抗菌和抗寄生虫。Rapanone 还是一种有效和选择性的人滑膜 PLA2 抑制剂，IC50 值为 2.6 μM。
Cas No.:573-40-0
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Rapanone is a natural benzoquinone. Rapanone exhibits a broad spectrum of biological actions, including anti-tumor, antioxidant, anti-inflammatory, antibacterial and antiparasitic. Rapanone also is a potent and selective human synovial PLA2 inhibitor, with an IC50 of 2.6 μM[1][2][3][4].
Rapanone (10-40 μM; 24 h) inhibits the cell viability, with IC50s of 35.58 μM and 27.89 μM for primary rats hepatocytes and HepG2 cells, respectively[1].Rapanone (10-40 μM; 24 h) induces a concentration-dependent mitochondrial membrane potential dissipation, ATP depletion, hydrogen peroxide generation and, phosphatidyl serine externalization in HepG2 cells[1].Rapanone inhibits electron transport at Complex III and promotes mitochondrial dysfunction[1].
Rapanone (2.5-10 mg/kg; i.p.) exhibits anti-inflammatory effects in the carrageenan paw oedema model in mice[4].
[1]. Andreu GLP, et, al. Rapanone, a naturally occurring benzoquinone, inhibits mitochondrial respiration and induces HepG2 cell death. Toxicol In Vitro. 2020 Mar;63:104737.
[2]. Morais LS, et, al. Antileishmanial compounds from Connarus suberosus: Metabolomics, isolation and mechanism of action. PLoS One. 2020 Nov 6;15(11):e0241855.
[3]. Vega-HernÁndez K, et, al. Discerning the antioxidant mechanism of rapanone: A naturally occurring benzoquinone with iron complexing and radical scavenging activities. J Inorg Biochem. 2017 May;170:134-147.
[4]. Ospina LF, et, al. Inhibition of acute and chronic inflammatory responses by the hydroxybenzoquinonic derivative rapanone. Planta Med. 2001 Dec;67(9):791-5.
| Cas No. | 573-40-0 | SDF | Download SDF |
| 别名 | 拉帕酮 | ||
| 分子式 | C19H30O4 | 分子量 | 322.44 |
| 溶解度 | 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。 |
||
| 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 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 3.1014 mL | 15.5068 mL | 31.0135 mL |
| 5 mM | 0.6203 mL | 3.1014 mL | 6.2027 mL |
| 10 mM | 0.3101 mL | 1.5507 mL | 3.1014 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。
Rapanone, a naturally occurring benzoquinone, inhibits mitochondrial respiration and induces HepG2 cell death
Toxicol In Vitro 2020 Mar;63:104737.PMID:31756542DOI:10.1016/j.tiv.2019.104737.
Rapanone is a natural occurring benzoquinone with several biological effects including unclear cytotoxic mechanisms. Here we addressed if mitochondria are involved in the cytotoxicity of Rapanone towards cancer cells by employing hepatic carcinoma (HepG2) cells and isolated rat liver mitochondria. In the HepG2, Rapanone (20-40 μM) induced a concentration-dependent mitochondrial membrane potential dissipation, ATP depletion, hydrogen peroxide generation and, phosphatidyl serine externalization; the latter being indicative of apoptosis induction. Rapanone toxicity towards primary rats hepatocytes (IC50 = 35.58 ± 1.50 μM) was lower than that found for HepG2 cells (IC50 = 27.89 ± 0.75 μM). Loading of isolated mitochondria with Rapanone (5-20 μM) caused a concentration-dependent inhibition of phosphorylating and uncoupled respirations supported by complex I (glutamate and malate) or the complex II (succinate) substrates, being the latter eliminated by complex IV substrate (TMPD/ascorbate). Rapanone also dissipated mitochondrial membrane potential, depleted ATP content, released Ca2+ from Ca2+-loaded mitochondria, increased ROS generation, cytochrome c release and membrane fluidity. Further analysis demonstrated that Rapanone prevented the cytochrome c reduction in the presence of decylbenzilquinol, identifying complex III as the site of its inhibitory action. Computational docking results of Rapanone to cytochrome bc1 (Cyt bc1) complex from the human sources found spontaneous thermodynamic processes for the quinone-Qo and Qi binding interactions, supporting the experimental in vitro assays. Collectively, these observations suggest that Rapanone impairs mitochondrial respiration by inhibiting electron transport chain at Complex III and promotes mitochondrial dysfunction. This property is potentially involved in Rapanone toxicity on cancer cells.
Optimization of Extraction Conditions and Cytotoxic Activity of Rapanone in Comparison to Its Homologue, Embelin
Molecules 2022 Nov 16;27(22):7912.PMID:36432013DOI:10.3390/molecules27227912.
Rapanone is a plant-derived simple alkyl-dihydroxybenzoquinone structurally close to embelin, a well-known cytotoxic agent. The pharmacological characterization of Rapanone is still incomplete, and to fill the data gap, a good source for its acquisition is required to conduct further research. This study aimed to optimize the conditions for the extraction of Rapanone from the leaves of white-berried Ardisia crenata Sims. For this purpose, three methods were employed: heat reflux (HRE), shaking (SE), and ultrasound-assisted extraction (UAE), and such parameters as the extraction time, solvent, and the number of extractions from the same sample were set as experimental variables. Furthermore, cytotoxic activity toward prostate cancer, thyroid cancer, and colorectal carcinoma cell lines was investigated and compared with doxorubicin and embelin. The most effective and economical method for the extraction of Rapanone was shown to be 20 min UAE with ethyl acetate or chloroform. Rapanone exhibited high cytotoxic activity against PC3 (IC50 = 6.50 μg/mL), Du145 (IC50 = 7.68 μg/mL), FTC133 (IC50 = 6.01 μg/mL), 8505C (IC50 = 7.84 μg/mL), and Caco-2 (IC50 = 8.79 μg/mL) cell lines after 24 h and against the HT29 cell line after 48 h (IC50 = 11.67 μg/mL). Furthermore, it revealed a more favorable safety profile than either its homologue, embelin, or doxorubicin. The set of optimal extraction parameters obtained may be utilized for scientific and industrial purposes to achieve the best Rapanone yield. Moreover, this benzoquinone revealed a high cytotoxic activity with good selectivity.
Discerning the antioxidant mechanism of Rapanone: A naturally occurring benzoquinone with iron complexing and radical scavenging activities
J Inorg Biochem 2017 May;170:134-147.PMID:28237732DOI:10.1016/j.jinorgbio.2017.02.019.
Oxidative stress resulting from iron and reactive oxygen species (ROS) homeostasis breakdown has been implicated in several diseases. Therefore, molecules capable of binding iron and/or scavenging ROS may be reasonable strategies for protecting cells. Rapanone is a naturally occurring hydroxyl-benzoquinone with a privileged chelating structure. In this work, we addressed the antioxidant properties of Rapanone concerning its iron-chelating and scavenging activities, and its protective potential against iron and tert-butyl hydroperoxide-induced damage to mitochondria. Experimental determinations revealed the formation of rapanone-Fe(II)/Fe(III) complexes. Additionally, the electrochemical assays indicated that Rapanone oxidized Fe(II) and O2-, thus inhibiting Fenton-Haber-Weiss reactions. Furthermore, Rapanone displayed an increased 2,2-diphenyl-1-picrylhydrazyl radical scavenging ability in the presence of Fe(II). The above results explained the capacity of Rapanone to provide near-full protection against iron and tert-butyl hydroperoxide induced mitochondrial lipid peroxidation in energized organelles, which fail under non-energized condition. We postulate that Rapanone affords protection against iron and reactive oxygen species by means of both iron chelating and iron-stimulated free radical scavenging activity.
Anti-melanoma potential of two benzoquinone homologues embelin and Rapanone - a comparative in vitro study
Toxicol In Vitro 2020 Jun;65:104826.PMID:32169436DOI:10.1016/j.tiv.2020.104826.
Rapanone and embelin are simple alkyl benzoquinone derivatives, mainly distributed in the Primulaceae. They have an interesting scope of biological activities including cytotoxicity. As melanoma is one of the most common types of cancer, in many cases resistant to current treatment regimens, the aim of this study was to assess and compare anti-melanoma activity of the two benzoquinones. Cytotoxicity of both compounds towards different melanoma cell lines (A375, HTB140, WM793) and selectivity with respect to normal keratinocytes (HaCaT) were investigated. Furthermore, interactions with a reference chemotherapeutic, doxorubicine, were assessed. Finally, analysis of anti-inflammatory, antioxidant and anti-tyrosinase activities of both benzoquinones was conducted as well. Rapanone showed selective and higher than doxorubicine cytotoxic potential against primary melanoma cell line, WM793. Although embelin was also highly cytotoxic, its selectivity was much poorer. Interestingly, in case of HTB140 and HaCaT cell lines a combination of each benzoquinone with doxorubicine potentiated the cytotoxic potential in a synergistic manner. Embelin revealed higher albumin anti-denaturation potential than Rapanone but lower than diclofenac sodium. Anti-hyaluronidase effect of both benzoquinones was higher than quercetin. Both compounds showed antioxidant potential although significantly lower as compared to vitamin C. Finally, neither embelin nor Rapanone had any inhibitory effect on tyrosinase.
Discovery of the Rapanone and suberonone mixture as a motif for leishmanicidal and antifungal applications
Bioorg Med Chem 2014 Jan 1;22(1):135-40.PMID:24331757DOI:10.1016/j.bmc.2013.11.044.
Leishmaniasis and fungal infections are significant diseases impacting worldwide public health. Treatments have developed greatly over time, however, there is a necessity to discover less toxic drugs, which have greater efficacy and are more economically accessible. This work conducted a screening of Cerrado species extracts: Connarus suberosus Planch. (Connaraceae), Neea theifera Oerst. (Nyctaginaceae) and Myrcia linearifolia Cambess. (Myrtaceae) against Leishmania (Leishmania) amazonensis, dermatophytes and yeasts. Leishmanicidal and antifungal tests were conducted using MTT colorimetric assay and CLSI methodology, respectively. Connarus suberosus extracts presented the most promising results against the aforementioned microorganisms, which has not been described in the literature. The root bark EtOAc extract was selected for chemical fractionation resulting in a mixture of Rapanone (1) and a previously unreported compound named as suberonone (2); a mixture of β-sitosterol (3) and stigmasterol (4); oleic acid (5); geranilgeraniol (6); and two derivatives obtained from 1 and 2 mixture. The Rapanone and suberonone mixture demonstrated a MIC of 15.62 μg/mL against Candida albicans ATCC 10231.