Marrubiin
(Synonyms: 夏至草素) 目录号 : GC61517
A labdane diterpenoid lactone with diverse biological activities
Cas No.:465-92-9
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
Marrubiin is a labdane diterpenoid lactone originally isolated from M. vulgare that has diverse biological activities.1,2,3 It inhibits potassium chloride-induced contractions of rat aortic rings (IC50 = 24 ?M).1 Marrubiin (100 mg/kg) inhibits ovalbumin-induced allergic ear edema in mice.2 It inhibits acetic acid-induced writhing and capsaicin-induced paw licking in mice with ID50 values of 2.2 and 28.8 ?mol/kg, respectively.3
1.El Bardai, S., Morel, N., Wibo, M., et al.The vasorelaxant activity of marrubenol and marrubiin from Marrubium vulgarePlanta Med.69(1)75-77(2003) 2.Stulzer, H.K., Tagliari, M.P., Zampirolo, J.A., et al.Antioedematogenic effect of marrubiin obtained from Marrubium vulgareJ. Ethnopharmacol.108(3)379-384(2006) 3.De Jesus, R.A., Cechinel-Filho, V., Oliveira, A.E., et al.Analysis of the antinociceptive properties of marrubiin isolated from Marrubium vulgarePhytomedicine7(2)111-115(2000)
| Cas No. | 465-92-9 | SDF | |
| 别名 | 夏至草素 | ||
| Canonical SMILES | O=C1[C@]2(C)[C@]3([H])[C@](C[C@@H](C)[C@](O)(CCC4=COC=C4)[C@@]3(C)CCC2)([H])O1 | ||
| 分子式 | C20H28O4 | 分子量 | 332.43 |
| 溶解度 | DMSO: 100 mg/mL (300.82 mM) | 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 | 3.0082 mL | 15.0408 mL | 30.0815 mL |
| 5 mM | 0.6016 mL | 3.0082 mL | 6.0163 mL |
| 10 mM | 0.3008 mL | 1.5041 mL | 3.0082 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。
Marrubiin
Molecules 2013 Jul 29;18(8):9049-60.PMID:23899837DOI:10.3390/molecules18089049.
The ethno-medicinal approach to drug discovery represents one of the most important sources of new and safe therapeutic agents to the challenges confronting modern medicine and daily life. Many of the traditionally important medicinal plants contain active molecules or ones that serve as precursors to biosynthesised secondary metabolites to which the biological activity could be attributed. Marrubiin is one such compound and is a potential valuable compound which exists in high concentrations in many traditionally important Lamiaceae species which have demonstrated excellent pharmacological properties with commendably high safety margins. Marrubiin's attributes include a low turnover, high stability and little catabolism, which are core characteristics required for therapeutic compounds and nutraceuticals of economic importance. In addition, Marrubiin is considered a potential substrate for potent active compounds viz; marrubiinic acid, and marrubenol. The contribution of Marrubiin to drug discovery thus needs to be put into prospective due to its ready availability, high potential applications and ease of modification. In this short review we highlight the most important chemical and pharmacological aspects reported on Marrubiin since it was discovered.
Marrubiin, a constituent of Leonotis leonurus, alleviates diabetic symptoms
Phytomedicine 2012 Apr 15;19(6):488-93.PMID:22326550DOI:10.1016/j.phymed.2011.12.008.
Aims: Marrubiin and an organic extract of Leonotis leonurus were tested in vitro and in vivo for their antidiabetic and anti-inflammatory activities. Materials and methods: INS-1 cells were cultured under normo- and hyperglycemic conditions conditions. An in vivo animal model confirmed the biological activities of Marrubiin and the organic extract observed in the studies in vitro. Results: The stimulatory index of INS-1 cells cultured under hyperglycemic conditions was significantly increased in cells exposed to the organic extract and Marrubiin, relative to the hyperglycaemic conditions. Insulin and glucose transporter-2 gene expressions were significantly increased by the organic extract and Marrubiin. Similarly, the extract and Marrubiin resulted in an increase in respiratory rate and mitochondrial membrane potential under hyperglycaemic conditions. Marrubiin increased insulin secretion, HDL-cholesterol, while it normalized total cholesterol, LDL-cholesterol, atherogenic index, IL-1β and IL-6 levels in an obese rat model. Conclusion: The results provide evidence that Marrubiin, a constituent of Leonotis leonurus, alleviates diabetic symptoms.
Protective effects of Marrubiin improve endometriosis through suppression of the expression of RANTES
Mol Med Rep 2017 Sep;16(3):3339-3344.PMID:28713901DOI:10.3892/mmr.2017.6969.
Marrubiin can improve blood and lymph microcirculation disturbance, and has pharmacological effects in myocardial protection, anti‑inflammation and anti‑oxidation. The aim of the present study was to evaluate the protective effects of Marrubiin on endometriosis through suppression of the expression of regulated on activation, normal T cell expressed and secreted (RANTES). Endometriotic cells were implanted into the peritoneal cavity of mice, and these mice were injected estradiol benzoate (30 µg/kg) once each day for 14 days. The mice with endometriosis were then treated with 12, 25 or 50 mg/kg Marrubiin. Reverse transcription‑quantitative polymerase chain reaction was used to assess the mRNA expression of RANTES, and western blot analysis was used to analyze the protein expression of RANTES, TNF‑α and PGE2. Inflammation factors were measured by ELISA. Treatment with Marrubiin effectively improved lesion regression and inhibited toxicity in the mouse model of endometriosis. Marrubiin significantly inhibited endometrial lesions and monocyte chemotaxis in the mice with endometriosis, and reduced U937 cell migration. Calcium mobilization, levels of tumor necrosis factor‑α and the secretion of RANTES were effectively suppressed by Marrubiin treatment. The calcium levels were effectively induced, whereas the protein expression of prostaglandin E2 (PGE2) and formation of thromboxane B2 (TXB2) were effectively inhibited by Marrubiin treatment. These findings indicated that the protective effect of Marrubiin improved endometriosis in the mice through the suppression of inflammation and downregulation of the expression of RANTES, followed by mediation of the levels of calcium, PGE2 and TXB2.
Supercritical CO2 extraction of Marrubium vulgare: intensification of Marrubiin
RSC Adv 2021 Mar 1;11(16):9067-9075.PMID:35423440DOI:10.1039/d0ra10253a.
Supercritical carbon dioxide and Soxhlet extraction were employed for delivering Marrubium vulgare extracts. By varying process temperature and pressure, the impact of different densities of carbon dioxide on the extraction yield and chemical profile of the extracts was investigated. The highest extraction yields of M. vulgare were obtained by supercritical carbon dioxide extraction (3.51%) at 300 bar and 60 °C, while the yield obtained with the Soxhlet extraction was 3.23%. The chemical profiles of these two extracts were significantly different and Marrubiin, the most dominant component of supercritical extracts was not present in extracts obtained by this conventional method. This labdane diterpene was the most abundant in extracts obtained at 200 bar and temperatures of 40, 50, and 60 °C (62.60, 68.41, and 71.96%, respectively). For the intensification of Marrubiin, supercritical fractions were collected in successive time intervals over the course of the extraction (300 bar/60 °C). It was determined that after 1 h of extraction the highest content of Marrubiin (75.14%) can be achieved. The similarities between the obtained extracts were estimated and the correlations to the content of identified lipophilic compounds were established using multivariate data analysis tools.
Total Syntheses of Marrubiin and Related Labdane Diterpene Lactones
Molecules 2020 Apr 1;25(7):1610.PMID:32244661DOI:10.3390/molecules25071610.
Total syntheses of the labdane diterpene lactones Marrubiin, marrulibacetal, desertine, marrulibacetal A, marrubasch F, cyllenine C, marrulanic acid, and marrulactone are described. The trans-decalin moiety of these molecules was constructed in a stereoselective manner by a Pauson-Khand reaction, and the resultant cyclopentenone was oxidatively cleaved for formation of the lactone ring. Elongation of the side chain at C9 was achieved by an epoxide-opening reaction with a variety of nucleophiles, and the functional group manipulations completed the syntheses of these natural products. Stereochemistries of desertine could be established by the transformations.