Isobergapten
(Synonyms: 异佛手柑内酯) 目录号 : GC39026
A furanocoumarin with diverse biological activities.
Cas No.:482-48-4
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
Isobergapten is a furanocoumarin that has been found in H. persicum and has diverse biological activities.1,2,3 It inhibits α-glucosidase and scavenges DPPH radicals in cell-free assays (IC50s = 0.385 and 28.6 ?M, respectively).1 Isobergapten is active against S. aureus, B. cereus, P. aeruginosa, and S. entritidis (MICs = 125 ?g/ml for all).2 It reduces tumor growth in a B16/F10 murine melanoma model when administered at a dose of 0.5 mg/kg in combination with ultraviolet A (UVA) radiation.3
1.Dehghan, H., Sarrafi, Y., Salehi, P., et al.α-Glucosidase inhibitory and antioxidant activity of furanocoumarins from Heracleum persicumMed. Chem. Res.26849-855(2017) 2.Dehghan, H., Rezaee, P., and Aliahmadi, A.Bioassay screening of 12 Iranian plants and detection of antibacterial compounds from Heracleum persicum using a TLC bioautography methodJ. Liq. Chromatogr. R. T.43381-387(2020) 3.Sumiyoshi, M., Sakanaka, M., Taniguchi, M., et al.Anti-tumor effects of various furocoumarins isolated from the roots, seeds and fruits of Angelica and Cnidium species under ultraviolet A irradiationJ. Nat. Med.68(1)83-94(2014)
| Cas No. | 482-48-4 | SDF | |
| 别名 | 异佛手柑内酯 | ||
| Canonical SMILES | O=C1C=CC2=C(OC)C=C(OC=C3)C3=C2O1 | ||
| 分子式 | C12H8O4 | 分子量 | 216.19 |
| 溶解度 | DMSO : 5.88 mg/mL (27.20 mM; ultrasonic and warming and heat to 60°C) | 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。 |
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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 | 4.6256 mL | 23.1278 mL | 46.2556 mL |
| 5 mM | 0.9251 mL | 4.6256 mL | 9.2511 mL |
| 10 mM | 0.4626 mL | 2.3128 mL | 4.6256 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。
A New Anti-Inflammatory Alkaloid from Roots of Heracleum dissectum
Chem Biodivers 2017 Sep;14(9).PMID:28556437DOI:10.1002/cbdv.201700184.
Using various chromatographic methods, a new piperidinone alkaloid, (3S)-3-{4-[(1E)-3-hydroxyprop-1-en-1-yl]-2-methoxyphenoxy}piperidin-2-one (1), together with 10 known compounds, bergapten (2), xanthotoxol (3), isopimpinellin (4), Isobergapten (5), heratomol-6-O-β-d-glucopyranoside (6), scopoletin (7), apterin (8), 3-methoxy-4-β-d-glucopyranosyloxypropiophenone, (praeroside; 9), tachioside (10) and coniferin (11), were isolated from roots of Heracleum dissectum Ledeb. Their structures were elucidated on the basis of physicochemical properties and the detailed interpretation of various spectroscopic data. All the isolated compounds were screened for anti-inflammatory activity in vitro. As the results, compound 1 and 8 showed significantly inhibitory activity on nitric oxide production in RAW264.7 cells.
The Canadian medicinal plant Heracleum maximum contains antimycobacterial diynes and furanocoumarins
J Ethnopharmacol 2013 May 2;147(1):232-7.PMID:23501157DOI:10.1016/j.jep.2013.03.009.
Ethnopharmacological relevance: Heracleum maximum is amongst the most commonly used plants by the indigenous peoples of North America. The First Nations of the eastern Canada use infusions of Heracleum maximum roots for the treatment of respiratory ailments including tuberculosis. Previous investigations of extracts derived from the roots of Heracleum maximum have shown it to possess antimycobacterial activity. Aim of the study: To isolate and identify antimycobacterial constituents from the roots of Heracleum maximum. Materials and methods: A methanolic extract of Heracleum maximum roots was subjected to bioassay guided fractionation using the microplate resazurin assay (MRA) to assess inhibitory activity against Mycobacterium tuberculosis strain H37Ra. The antimycobacterial constituents were identified by NMR, MS and polarimetry. Results: The polyacetylene (3R,8S)-falcarindiol and the furanocoumarins bergapten, Isobergapten, angelicin, sphondin, pimpinellin, isopimpinellin and 6-isopentenyloxyisobergapten were isolated from the Heracleum maximum root extract. (3R,8S)-Falcarindiol and 6-isopentenyloxyisobergapten exhibited MICs of 24 μM and 167 μM and IC50s of 6 μM and 27 μM against Mycobacterium tuberculosis H37Ra respectively. The remaining furanocoumarins bergapten, Isobergapten, angelicin, sphondin, pimpinellin, and isopimpinellin were less active, with MICs of 925, 1850, 2149, 1859, 812 and 1625 μM and IC50s of 125, 344, 350, 351, 389 and 406 μM. Conclusions: (3R,8S)-Falcarindiol, bergapten, Isobergapten, angelicin, sphondin, pimpinellin, isopimpinellin and 6-isopentenyloxyisobergapten were identified as the principal constituents responsible for the antimycobacterial activity of the roots of Heracleum maximum. This work supports the ethnopharmacological use of Heracleum maximum by Canadian First Nations and Native American communities as a treatment for infectious diseases, specifically tuberculosis.
[Chemical constituents of Incarvillea younghusbandii]
Zhongguo Zhong Yao Za Zhi 2010 Jan;35(1):58-62.PMID:20349717DOI:10.4268/cjcmm20100112.
Objective: To study the chemical constituents of Incarvillea younghusbandii. Method: The chemical constituents were isolated by various column chromatographic methods and structurally identified by NMR and MS evidence. Result: Fifteen compounds were obtained and identified as Isobergapten (1), sphondin (2), imperatorin (3), xanthotoxin (4), phellopterin (5), heraclenol (6), rivulobirin A (7), methyl oleanolate (8), methyl caffeate (9), grevillic acid (10), boschniakinic acid (11), tert-O-beta-D-glucopyranosyl-(R)-heraclenol (12), 5-methoxy-8-O-beta-D-glucopyranosyloxypsoralen (13), 1'-O-beta-D-glucopyranosyl-3-hydroxynodakenetin (14) and phenylethyl-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranoside (15). Conclusion: All of these compounds were isolated from this plant for the first time and most of them are furocoumarins.
Anti-tumor effects of various furocoumarins isolated from the roots, seeds and fruits of Angelica and Cnidium species under ultraviolet A irradiation
J Nat Med 2014 Jan;68(1):83-94.PMID:23649674DOI:10.1007/s11418-013-0774-z.
We examined the effects on cell proliferation of 10 methoxyfurocoumarins and 7 dihydrofurocumarins isolated from Umbelliferae medicinal plants, and their mechanisms of action against B16F10 melanoma cells or in melanin-possessing hairless mice implanted with B16F10 melanoma cells, under UVA irradiation. Furocoumarins having a methoxy group, such as bergapten (1), xanthotoxin (2), phellopterin (4), byakangelicin (6), neobyakangelicin (8), Isobergapten (9) and sphondin (10), showed anti-proliferative activity and caused G2/M arrest at concentrations of 0.05-15.0 μM. The 7 dihydrofurocoumarins had no effect. UVA plus 1, 2, 4, 6 and sec-O-acetylbyakagelicin (7), having one methoxy group at the C-5 position and a linear-type conformation, reduced tumor growth and final tumor weight in B16F10-bearing mice at 0.5 or 1.0 mg/kg (intraperitoneal injection). UVA plus 1 and 2 increased Chk1 phosphorylation and decreased cdc2 (Thr 161) phosphorylation in the melanoma cells. The anti-tumor actions of UVA plus furocoumarins having a methoxy group might be due to the arrest of the cell cycle at G2/M through an increase in phospho-Chk1 and reduction in phospho-cdc2.
Furocoumarins of Heracleum laciniatum: isolation, phototoxicity, absorption and action spectra studies
Contact Dermatitis 1983 Jul;9(4):257-62.PMID:6617185DOI:10.1111/j.1600-0536.1983.tb04386.x.
Isolation of the furocoumarins (psoralens) bergapten, Isobergapten, sphondin, isopimpinellin and pimpinellin from the Umbilliferous plant Heracleum laciniatum was carried out by column chromatography, and the structure and absorption spectra for the 5 furocoumarins isolated are described. Photoepicutaneous testing showed the strongest phototoxic effects from bergapten, marked effects from pimpinellin, weak effects from sphondin and none from the others. These in vivo findings were confirmed by the in vitro Candida test. Action spectrum studies demonstrated peak photosensitivity in the range 330-335 nm, bergapten being more than twice as phototoxic as pimpinellin.