Heraclenin
(Synonyms: 独活内酯) 目录号 : GC36220
Heraclenin，是一种天然呋喃香豆素，可从 Prangos pabularia 根部分离出来。Heraclenin 通过靶向激活的 T 细胞核因子 (NFAT) 来抑制人原代 T 细胞中 T 细胞受体介导的增殖，这种作用存在浓度依赖性。
Cas No.:2880-49-1
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
Heraclenin, a natural furanocoumarin, isolated from the root parts of the plant Prangos pabularia. Heraclenin significantly inhibits T cell receptor-mediated proliferation in human primary T cells in a concentration-dependent manner by targeting nuclear factor of activated T-cells (NFAT)[1]. NFAT[1]
[1]. MÁrquez N, et al. Imperatorin inhibits T-cell proliferation by targeting the transcription factor NFAT. Planta Med. 2004 Nov;70(11):1016-21.
| Cas No. | 2880-49-1 | SDF | |
| 别名 | 独活内酯 | ||
| Canonical SMILES | CC1(C)[C@H](O1)COC2=C(OC=C3)C3=CC(C=C4)=C2OC4=O | ||
| 分子式 | C16H14O5 | 分子量 | 286.28 |
| 溶解度 | Soluble in DMSO | 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 | 3.4931 mL | 17.4654 mL | 34.9308 mL |
| 5 mM | 0.6986 mL | 3.4931 mL | 6.9862 mL |
| 10 mM | 0.3493 mL | 1.7465 mL | 3.4931 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。
Osteogenic stimulatory effect of Heraclenin purified from bael in mouse mesenchymal stem cells in vitro
Chem Biol Interact 2019 Sep 1;310:108750.PMID:31319076DOI:10.1016/j.cbi.2019.108750.
Osteoporosis is a major health concern occurring to the aging adult population across the globe. Currently, there is an increasing demand for treatment of osteoporosis with plant-based medicines. In the present study, we report that Heraclenin was extracted and purified from unripe fruit portion of Bael (Aegle marmelos Corr.) using silica gel column chromatography. The identification and characterization of Heraclenin were carried out by UV-Vis, HPLC, LC-MS, NMR, FT-IR, and XRD analyses. The standardized purification method recorded a yield efficiency of 42% Heraclenin microcrystals with 99% purity from bael fruit. SEM image revealed the shape of the purified compound to be an orthorhombic-sphenoid prism. Cytotoxicity studies indicated that heraclenin-treatment did not alter cell viability in mouse mesenchymal stem cells (mMSCs, C3H10T1/2). The mRNA expression of Runx2, a bone transcription factor was found to be stimulated by Heraclenin in these cells. At the cellular level, heraclenin-treatment enhanced osteoblast differentiation and mineralization in mMSCs. Thus, these results suggested that Heraclenin purified from bael fruit has an osteogenic effect, indicating its potential towards bone regeneration.
Mutagenicity of a furocoumarin epoxide, Heraclenin, in Chlamydomonas reinhardii
Mutat Res 1986 Jan-Feb;169(1-2):47-50.PMID:3945236DOI:10.1016/0165-1218(86)90017-0.
Treatment of arg- or strd mutant cells of Chlamydomonas reinhardii with a furocoumarin epoxide, Heraclenin, plus UV-A resulted in a decrease in survival and a UV-A dose-dependent increase in induced Arg+ or Strs revertants. Imperatorin, a furocoumarin with a very similar structure but lacking an epoxide group showed a very similar phototoxic and photomutagenic activity in these mutant strains. Treating the mutant cells with Heraclenin or imperatorin in the dark neither influenced survival nor mutation induction. The results are discussed with respect to the involvement of the epoxide moiety of Heraclenin in mutagenicity.
Chromosome-damaging effects of Heraclenin in human lymphocytes in vitro
Mutat Res 1986 Jan-Feb;169(1-2):51-4.PMID:3945237DOI:10.1016/0165-1218(86)90018-2.
Heraclenin, a furocoumarin with an epoxide group in its side chain, was analyzed to see if it induced structural chromosome aberrations and sister-chromatid exchanges (SCEs) in human lymphocytes in vitro. The results were compared directly with those of imperatorin, which differs from Heraclenin only in lacking an epoxide group. An equally strong clastogenic effect was found for both Heraclenin and imperatorin: the number of metaphases with breaks was increased in both cases by approximately a factor of 6. Heraclenin produced a considerable dose-dependent increase in the SCE rate, i.e., by about 60 induced SCEs/metaphase, whereas imperatorin induced only about 4 SCEs/metaphase. The results are discussed with respect to the occurrence of structural aberrations, which are primarily due to the basic furocoumarin structure itself, whereas the large increase in the SCE rate produced by Heraclenin is most probably significantly influenced by its epoxide group.
Coumarins from Opopanax chironium. New dihydrofuranocoumarins and differential induction of apoptosis by imperatorin and Heraclenin
J Nat Prod 2004 Apr;67(4):532-6.PMID:15104479DOI:10.1021/np0340652.
Opopanax chironium is a rich source of furano- and dihydrofuranocoumarins, whose accumulation in all plant parts and especially the roots is presumably responsible for the poisonous properties of the species. The presence of two distinct chemotypes was evidenced, with the one from Sicily affording the new dihydrofuranocoumarins 5d and 5e, while extracts from the Sardinian chemotype showed powerful apoptotic activity, which was traced to the prenylated furanocoumarins Heraclenin (2a) and imperatorin (2b). Despite a close structural similarity, compounds 2a and 2b induced apoptosis in Jurkat leukemia cells in mechanistically different ways.
New coumarin from the roots of Prangos pabularia
Nat Prod Res 2018 Oct;32(19):2325-2332.PMID:29224384DOI:10.1080/14786419.2017.1413558.
The new coumarin 1, yuganin A (7-methoxy-8-((1S,2S)-1,2,3-trihydroxy-3-methylbutyl)-2H-chromen-2-one) along with nine known coumarins, heraclenol 3'-O-β-D-glucopyranoside (2), oxypeucedanin hydrate 3'-O-β-D-glucopyranoside (3), heraclenol (4), oxypeucedanin hydrate (5), osthole (6), oxypeucedanin (7), Heraclenin (8), isoimperatorin (9), imperatorin (10) and the disaccharide sucrose (11), have been isolated from the roots of Prangos pabularia, and the structures of these isolated compounds were elucidated by spectroscopic means, especially, UV, HR-ESIMS, and 1D and 2D NMR spectroscopy. Furthermore, the anti-melanogenic effect of yuganin A and its inhibitory effect on B16 cells were evaluated. Yuganin A may be useful in the treatment of hyperpigmentation and as a skin-whitening agent in the cosmetics industry.