Isopimpinellin
(Synonyms: 异茴芹灵) 目录号 : GC39140
A furanocoumarin with diverse biological activities
Cas No.:482-27-9
Sample solution is provided at 25 µL, 10mM.
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Isopimpinellin is a furanocoumarin that has been found in H. persicum and has diverse biological activities.1,2,3 It inhibits lipid peroxidation in a cell-free assay.1 Isopimpinellin (20 ?M) prevents histamine release from, and activation of NF-κB in, RBL-2H3 cells.2 It also decreases the secretion of TNF-α, IL-1β, and IL-4 from RBL-2H3 cells. Isopimpinellin prevents benzo[a]pyrene-DNA adduct formation in sensitivity to carcinogenesis (SENCAR) mice when administered at a dose of 70 mg/kg and reduces the number of papillomas initiated and promoted by 7,12-dimethylbenz[a]anthracene in SENCAR mice when administered at 30, 70, or 150 mg/kg.3
1.Souri, E., Farsam, H., Sarkheil, P., et al.Antioxidant activity of some furanocoumarins isolated from Heracleum persicumPharm. Biol.42(6)396-399(2004) 2.Li, D., and Wu, L.Coumarins from the roots of Angelica dahurica cause anti-allergic inflammationExp. Ther. Med.14(1)874-880(2017) 3.Kleiner, H.E., Vulimiri, S.V., Starost, M.F., et al.Oral administration of the citrus coumarin, isopimpinellin, blocks DNA adduct formation and skin tumor initiation by 7,12-dimethylbenz[α]anthracene in SENCAR miceCarcinogenesis23(10)1667-1675(2002)
| Cas No. | 482-27-9 | SDF | |
| 别名 | 异茴芹灵 | ||
| Canonical SMILES | O=C1C=CC2=C(OC)C3=C(OC=C3)C(OC)=C2O1 | ||
| 分子式 | C13H10O5 | 分子量 | 246.22 |
| 溶解度 | DMSO : 50 mg/mL (203.07 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 | 4.0614 mL | 20.307 mL | 40.6141 mL |
| 5 mM | 0.8123 mL | 4.0614 mL | 8.1228 mL |
| 10 mM | 0.4061 mL | 2.0307 mL | 4.0614 mL |
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| 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 |
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| % DMSO % % Tween 80 % saline | ||||||||||
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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。
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Isopimpinellin extends antiangiogenic effect through overexpression of miR-15b-5p and downregulating angiogenic stimulators
Mol Biol Rep 2022 Jan;49(1):279-291.PMID:34709570DOI:10.1007/s11033-021-06870-4.
Background: Angiogenesis is the formation of new blood vessels from an existing vasculature through a series of processes such as activation, proliferation, and directed migration of endothelial cells. Angiogenesis is instrumental in the metastatic spread of tumors. Isopimpinellin, a furanocoumarin group of phytochemicals, is an anticarcinogenic agent. However, no studies have proven its antiangiogenic effects. The current study thus aimed to screen the antiangiogenic effect of Isopimpinellin. Methods and results: Human Umblical Vein Endothelial Cell (HUVEC) as an in vitro model and zebrafish embryos as an in vivo model was used in this study. The experimental results showed that Isopimpinellin effectively inhibited HUVEC proliferation, invasion, migration, and tube formation, which are the key steps in angiogenesis by markedly suppressing the expression of pro-angiogenic genes VEGF, AKT, and HIF-1α. In addition, Isopimpinellin exerts its anti-angiogenic effect through the regulation of miR-15b-5p and miR-542-3p. Furthermore, in zebrafish embryos, Isopimpinellin inhibited the development of intersegmental vessels (ISVs) through the significant downregulation of all pro-angiogenic genes vegf, vegfr2, survivin, angpt-1, angpt-2, and tie-2. Conclusion: Collectively, these experimental findings offer novel insights into the antiangiogenic nature of Isopimpinellin and open new avenues for therapeutic approaches.
The biosynthesis of Isopimpinellin
Can J Biochem 1977 Jul;55(7):686-92.PMID:890566DOI:10.1139/o77-099.
Bergapten and xanthotoxin, labelling in the methyl group wich carbon-14 or tritiated at three skeletal carbons, were administered to leaves of Heracleum lanatum and to cell cultures of Ruta graveolens. In all experiments xanthotoxin was the more efficient precursor of Isopimpinellin, although bergapten was always incorporated to a measurable extent. Double-labelling experiments showed that both precursors, especially bergapten, underwent considerable demethylation (and presumably remethylation) before conversion to Isopimpinellin. 5-Hydroxyxanthotoxin and 8-hydroxybergapten were both O-methylated by cell-free extracts of Ruta cells to Isopimpinellin, in reactions mediated by discrete O-methyltransferases. 8-Hydroxy[Me-14C]bergapten was converted with a high degree of incorporation to Isopimpinellin by Ruta cells in vivo, and it is suggested that the preference for the pathway via xanthotoxin may be due to more rapid hydroxylation of this substrate.
Microbial transformation of Isopimpinellin by Glomerella cingulata
J Oleo Sci 2011;60(11):575-8.PMID:22027023DOI:10.5650/jos.60.575.
Microbial transformation studies conducted on Isopimpinellin (1) by the fungus Glomerella cingulata have revealed that 1 was metabolized to give the corresponding reduced acid, 5,8-dimethoxy-6,7-furano-hydrocoumaric acid (2). The structure of metabolite 2 was elucidated by high-resolution mass spectrometry (HR-MS), extensive NMR techniques, including (1)H NMR, (13)C NMR, (1)H-(1)H correlation spectroscopy (COSY), heteronuclear multiple quantum coherence (HMQC) and heteonuclear multiple bond coherence (HMBC). The biotransformed product 2 showed weak a in vitro β-secretase (BACE1) inhibitory effect.
Oral administration of the citrus coumarin, Isopimpinellin, blocks DNA adduct formation and skin tumor initiation by 7,12-dimethylbenz[a]anthracene in SENCAR mice
Carcinogenesis 2002 Oct;23(10):1667-75.PMID:12376476DOI:10.1093/carcin/23.10.1667.
The current study was designed to evaluate the effects of oral administration of the citrus coumarin, Isopimpinellin, on skin tumor initiation by topically applied benzo[a]pyrene (B[a]P) and 7,12-dimethylbenz[a]anthracene (DMBA). To evaluate the effects of orally administered Isopimpinellin on skin tumor initiation by B[a]P and DMBA, its effects on DNA adduct formation were first evaluated. Female SENCAR mice were pre-treated twice with corn oil, or Isopimpinellin (70 mg/kg body wt per os) at 24 h and 2 h prior to topical treatment with B[a]P or DMBA. Another citrus coumarin, imperatorin, was also included in these experiments for comparison. Orally administered Isopimpinellin and imperatorin significantly inhibited B[a]P-DNA adduct formation by 37 and 26%, respectively. Imperatorin also blocked DMBA-DNA adduct formation by 43%. In a second dose-response study, orally administered Isopimpinellin (35, 70 and 150 mg/kg) blocked DMBA-DNA adduct formation by 23, 56 and 69%, respectively. For the tumor study, mice were pretreated orally with corn oil or Isopimpinellin at 24 and 2 h prior to initiation with DMBA, and 2 weeks later promotion began with 12-O-tetradecanoylphorbol-13-acetate (TPA). Isopimpinellin significantly reduced the mean number of papillomas per mouse by 49, 73 and 78% compared to corn oil controls at 30, 70 and 150 mg/kg body wt, respectively. Orally administered Isopimpinellin also significantly reduced the percentage of mice with papillomas at the highest dose tested (150 mg/kg). The effectiveness of Isopimpinellin given topically over a broad dose range against DMBA tumor initiation was also evaluated for comparison. As part of this study, several parameters of systemic toxicity were evaluated following oral dosing with Isopimpinellin and imperatorin. Mice were treated orally with corn oil, Isopimpinellin or imperatorin (35, 70 and 150 mg/kg body wt per os) once daily for four consecutive days, killed at 24 h after the last dose, and livers, lungs, and kidneys evaluated histologically. In addition, urinary parameters of nephrotoxicity, blood parameters of liver and kidney function, and thrombin clotting time were assayed. No significant changes in blood clotting, or renal or hepatic function were observed. There was, however, a significant increase in liver wt accompanied by cytoplasmic vacuolation of hepatocytes. There were no histopathological changes in lungs or kidneys. Overall, these data indicate that Isopimpinellin (and imperatorin) have chemopreventive effects when administered orally on skin tumor initiation by DMBA.
Simultaneous determination of osthole, bergapten and Isopimpinellin in rat plasma and tissues by liquid chromatography-tandem mass spectrometry
J Chromatogr B Analyt Technol Biomed Life Sci 2014 Nov 1;970:77-85.PMID:25240925DOI:10.1016/j.jchromb.2014.06.014.
A highly selective and sensitive method for simultaneous quantitation of osthole, bergapten and Isopimpinellin in rat plasma and tissues was developed by liquid chromatography-tandem quadrupole mass spectrometry (LC-MS/MS). After liquid-liquid extraction of samples with methyl tert-butyl ether, the analytes and dextrorphan (internal standard, IS) were separated by a Hypersil GOLD AQ C18 column with gradient elution of acetonitrile and water containing 0.5‰ formic acid. Three determinands were detected using an electrospray ionization (ESI) tandem mass spectrometry in the multiple reaction monitoring (MRM) modes with positive electrospray ionization. Calibration curves were recovered over the concentration ranges of 1-200 ng/ml, 1-500 ng/ml, 0.25-200 ng/ml for osthole, bergapten and Isopimpinellin in plasma; 1-100 ng/ml, 1-500 ng/ml, 0.5-100 ng/ml for osthole, bergapten and Isopimpinellin in tissues, respectively. The intra-day precision (R.S.D.) was within 13.90% and the intra-day accuracy (R.E.) was within -6.27 to 6.84% in all biological matrixes. The inter-day precision (R.S.D.) was less than 13.66% and the inter-day accuracy (R.E.) was within -10.64 to 13.04%. Then the method was successfully applied to investigate plasma pharmacokinetic study and tissue distribution of osthole, bergapten and Isopimpinellin in rats after oral administration of Fructus Cnidii extraction, especially for testis/uterus tissue distribution. The results demonstrated that osthole, bergapten and Isopimpinellin were absorbed and eliminated rapidly with wide distributions in rats. Distribution data of these three bioactive components in testis/uterus tissues could offer useful information for the further preclinical and clinical studies of Fructus Cnidii in the treatment of genital system disease.