Bergamottin (5-Geranoxypsoralen)
(Synonyms: 佛手柑素,5-Geranoxypsoralen; Bergamotine; Bergaptin) 目录号 : GC34132
A naturally occurring furanocoumarin with diverse biological activities
Cas No.:7380-40-7
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Kinase experiment: | CYP1A1 Supersomes and different concentrations of 7-ethoxyresorufin (ER) are used to determine CYP1A1 enzymatic kinetics. A typical Michaelis-Menten curve is found. The final reaction mixture contains: 1 pmol CYP1A1, 0.5 mM NADPH, different ER concentrations and 0, 4, 8 and 16 nM of Bergamottin (BG). The reaction is started with the addition of NADPH. Kinetic constants are obtained by a nonlinear regression analysis of experimental data fitted to Michaelis-Menten equation with competitive-type inhibition. Kinetic analysis is also shown by using the Lineweaver-Burk, Dixon and replot of the slopes of the Dixon plot[1]. |
Cell experiment: | Inhibition of cell proliferation by Bergamottin is measured by the MTT assay. Briefly, the human lung adenocarcinoma cancer A549 cells are plated in 96-well culture plates (1×105 cells/well). After 24 h of incubation, the cells are treated with Bergamottin (0, 5, 10, 25, 50, 75 and 100 μM) for 24 and 48 h, MTT solution (10 mg/mL) is then added to each well. After a 4-h incubation, the formazan precipitate is dissolved in 100 μL DMSO, and then the absorbance is measured in an automated microplated reader at 570 nm. The cell viability ratio is calculated. Cytotoxicity is expressed as the concentration of Bergamottin needed to inhibit cell growth by 50% (IC50 value)[2]. |
Animal experiment: | Mice[2]Female BALB/c nude mice (six weeks old) (a total of 20 are obtained) are maintained with water and food ad libitum in a pathogen-free environment with a 12 h light and 12 h dark cycle in an animal care facility. Human non‑small cell lung carcinoma A549 cells (2×106 cells/mouse) are injected into the right axilla of the nude mice (5 mice/group) to create tumors in the mice. Subsequent to tumor development, the mice are divided into 4 groups and treated with Bergamottin injected intraperitoneally. The control group in the study is treated with an equal amount of PBS while the other three groups are treated with 25, 50 and 100 mg/kg of Bergamottin. Afterwards, the mice are sacrificed after 18 days, and the tumor weight and volume of each mouse are evaluated. Tumor length and width are measured using a Vernier caliper and the tumor volume (TV) is calculated[2]. |
References: [1]. Olguín-Reyes S, et al. Bergamottin is a competitive inhibitor of CYP1A1 and is antimutagenic in the Ames test. Food Chem Toxicol. 2012 Sep;50(9):3094-9. | |
Bergamottin is a furanocoumarin found in grapefruit juice and lemon, lime, and bergamot oils that has diverse biological activities.1 In vitro, bergamottin inhibits migration and invasion of HT-1080 fibrosarcoma cells at sub-cytotoxic concentrations via inhibition of matrix metalloproteinase-9 (MMP-9) expression.2 It shows antiproliferative activity against HepG2 liver, HL-60 leukemia, and BGC-823 gastric cancer cell lines in a dose-dependent manner and induces cell death of CHO cells following near ultraviolet irradiation.1,3 Bergamottin inhibits the cytochrome P450 isoform 3A4 (CYP3A4; Ki = 7.7 μM) and is a mixed inhibitor of simvastatin drug metabolism (Ki = 174 μM).4,5 It also increases glucose consumption in HepG2 cells in a dose-dependent manner.3
1.Ashwood-Smith, M.J., Ceska, O., Warrington, P.J., et al.The photobiological activity of 5-geranoxypsoralen and its photoproductsPhotochem. Photobiol.55(4)529-532(1992) 2.Hwang, Y.P., Yun, H.J., Choi, J.H., et al.Suppression of phorbol-12-myristate-13-acetate-induced tumor cell invasion by bergamottin via the inhibition of protein kinase Cdelta/p38 mitogen-activated protein kinase and JNK/nuclear factor-kappaB-dependent matrix metalloproteinase-9 expressionMol. Nutr. Food Res.54(7)977-990(2010) 3.Liu, Y., Ren, C., Cao, Y., et al.Characterization and purification of bergamottin from Citrus grandis (L.) Osbeck cv. Yongjiazaoxiangyou and its antiproliferative activity and effect on glucose consumption in HepG2 cellsMolecules22(7)(2017) 4.He, K., Iyer, K.R., Hayes, R.N., et al.Inactivation of cytochrome P450 3A4 by bergamottin, a component of grapefruit juiceChem. Res. Toxicol.11(4)252-259(1998) 5.Le Goff-Klein, N., Koffel, J.C., Jung, L., et al.In vitro inhibition of simvastatin metabolism, a HMG-CoA reductase inhibitor in human and rat liver by bergamottin, a component of grapefruit juiceEur. J. Pharm. Sci.18(1)31-35(2003)
| Cas No. | 7380-40-7 | SDF | |
| 别名 | 佛手柑素,5-Geranoxypsoralen; Bergamotine; Bergaptin | ||
| Canonical SMILES | O=C1C=CC2=C(OC/C=C(C)/CC/C=C(C)/C)C3=C(OC=C3)C=C2O1 | ||
| 分子式 | C21H22O4 | 分子量 | 338.4 |
| 溶解度 | DMSO: 50 mg/mL (147.75 mM); Water: < 0.1 mg/mL (insoluble) | 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 | 2.9551 mL | 14.7754 mL | 29.5508 mL |
| 5 mM | 0.591 mL | 2.9551 mL | 5.9102 mL |
| 10 mM | 0.2955 mL | 1.4775 mL | 2.9551 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。
Bergamottin and 5-Geranyloxy-7-methoxycoumarin Cooperate in the Cytotoxic Effect of Citrus bergamia (Bergamot) Essential Oil in Human Neuroblastoma SH-SY5Y Cell Line
Toxins (Basel) 2021 Apr 10;13(4):275.PMID:33920139DOI:10.3390/toxins13040275.
The plant kingdom has always been a treasure trove for valuable bioactive compounds, and Citrus fruits stand out among the others. Bergamottin (BRG) and 5-geranyloxy-7-methoxycoumarin (5-G-7-MOC) are two coumarins found in different Citrus species with well-acknowledged pharmacological properties. Previously, they have been claimed to be relevant in the anti-proliferative effects exerted by bergamot essential oil (BEO) in the SH-SY5Y human neuroblastoma cells. This study was designed to verify this assumption and to assess the mechanisms underlying the anti-proliferative effect of both compounds. Our results demonstrate that BRG and 5-G-7-MOC are able to reduce the proliferation of SH-SY5Y cells, inducing apoptosis and increasing cell population in sub-G0/G1 phase. Moreover, we demonstrated the pro-oxidant activity of the two coumarins that increased reactive oxygen species and impaired mitochondrial membrane potential. From a molecular point of view, BRG and 5-G-7-MOC were able to modulate apoptosis related factors at both protein and gene levels. Lastly, we evaluated the synergistic effect of their combination, finding that the highest synergy was observed at a concentration ratio similar to that occurring in the BEO, supporting our initial hypothesis. Taken together, our results deepen the knowledge regarding the effect of BRG and 5-G-7-MOC in SH-SY5Y cells, emphasizing the relevance of their cooperation in achieving this effect.
Pharmacokinetics and pharmacodynamic interaction of Bergamottin with atorvastatin in rats
Xenobiotica 2022 May;52(5):463-467.PMID:35699169DOI:10.1080/00498254.2022.2090301.
1. The pharmacokinetics and pharmacodynamic of concomitant administration of atorvastatin with Bergamottin were investigated perspectives to reveal the potential herb-drug interaction between these two drugs.2. The hyperlipidaemia-induced Wistar rats received atorvastatin with or without Bergamottin (2.5 mg/kg). The concentration of atorvastatin in the rats' serum was determined using an established HPLC/MS/MS method. The pharmacokinetic parameters were calculated using DAS software. Lipid levels were determined.3. Bergamottin increases the Cmax (from 48 ± 5 ng/mL to 89 ± 7 ng/mL), AUC0-∞ (from 176 ± 27 to 552 ± 131 h∗μg/L), and the elimination half-life of atorvastatin (t1/2) of atorvastatin. Co-administration of atorvastatin with Bergamottin decreased total cholesterol (by 14%), low-density lipoproteins-cholesterol (by 20%), and triglyceride (by 12%), but increased thigh-density lipoprotein-cholesterol, when compared with atorvastatin alone.4. Co-administration of Bergamottin and atorvastatin alters both pharmacokinetics and pharmacodynamics of atorvastatin. This study provides pre-clinical information evidence that Bergamottin could potentiate the therapeutic efficacy of atorvastatin or increase its accumulation and adverse effects.
Bergamottin protects against LPS-induced endotoxic shock by regulating the NF-κB signaling pathway
Immunol Res 2022 Feb;70(1):33-43.PMID:34632552DOI:10.1007/s12026-021-09235-y.
Bergamottin is a natural furanocoumarin compound that possesses antioxidative and anti-cancer properties; however, the effect of Bergamottin on lipopolysaccharide (LPS)-induced inflammation response is unknown. In this study, we investigated the protective effects and mechanisms of Bergamottin against LPS-induced inflammatory responses.Raw264.7 cells were pre-treated with Bergamottin, then stimulated with LPS. Morphologic analysis and flow cytometry were used to measure Bergamottin-related cytotoxicity. ELISA and qPCR were performed to measure secretion and transcription activities of inflammatory cytokines. Biochemical analysis was used to determine the expression of tissues damage indicators. Western blots were used to determine protein expression, and immunofluorescence staining was used to determine the co-localization of NF-κB and RelA. Hematoxylin and eosin staining was used to show the pathological damages.Bergamottin had no cytotoxic effects on Raw264.7 cells. Pre-treatment with Bergamottin inhibited inflammatory cytokines expression and secretion induced by LPS, due to the inhibition of LPS-induced NF-κB signaling pathway activation, and improved pathological damages. These findings suggest that Bergamottin protects against LPS-induced endotoxin shock by regulating the NF-κB signaling pathway.
Photoreactivity of 5-Geranoxypsoralen and lack of photoreaction with DNA
Photochem Photobiol 1991 Jan;53(1):13-9.PMID:2027902DOI:10.1111/j.1751-1097.1991.tb08461.x.
5-Geranoxypsoralen, commonly called Bergamottin, a major furocoumarin contained in bergamot oil, is reported in vitro as a highly photoreactive psoralen. In ethanol, it exhibits quite a high triplet state quantum yield (approximately 0.37). The triplet state is involved in subsequent photochemistry which depends on the initial concentration and on the presence of oxygen. In contrast to most psoralens, absorption and fluorescence data suggest that 5-Geranoxypsoralen does not interact with DNA in the dark. No UVA-induced interstrand cross-links in DNA were shown.
Bergamottin, a bioactive component of bergamot, inhibits SARS-CoV-2 infection in golden Syrian hamsters
Antiviral Res 2022 Aug;204:105365.PMID:35732228DOI:10.1016/j.antiviral.2022.105365.
Severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2) has caused an ongoing pandemic, coronavirus disease-2019 (COVID-19), which has become a major global public health event. Antiviral compounds remain the predominant means of treating COVID-19. Here, we reported that Bergamottin, a furanocoumarin originally found in bergamot, exhibited inhibitory activity against SARS-CoV-2 in vitro, ex vivo, and in vivo. Bergamottin interfered with multiple stages of virus life cycles, specifically blocking the SARS-CoV-2 spike-mediated membrane fusion and effectively reducing viral RNA synthesis. Oral delivery of Bergamottin to golden Syrian hamsters at dosages of both 50 mg/kg and 75 mg/kg reduced the SARS-CoV-2 load in nasal turbinates and lung tissues. Pathological damage caused by viral infection was also ameliorated after Bergamottin treatment. Overall, our study provides evidence of Bergamottin as a promising natural compound, with broad-spectrum anti-coronavirus activity, that could be further developed in the fight against COVID-19 infection during the current pandemic.