Remisporine B
目录号 : GC48420
A polyketide with immunosuppressant activity
Cas No.:571194-06-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Remisporine B is a polyketide and derivative of remisporine A that has been found in Penicillium and has immunosuppressant activity.1,2 It inhibits LPS- or concanavalin A-induced proliferation of isolated mouse splenic lymphocytes (IC50s = 30.1 and 32.4 µg/ml, respectively).1
1.Liu, H., Chen, S., Liu, W., et al.Polyketides with immunosuppressive activities from mangrove endophytic fungus Penicillium sp. ZJ-SY2Mar. Drugs14(12)217(2016) 2.Kong, F., and Carter, G.T.Remisporine B, a novel dimeric chromenone derived from spontaneous Diels-Alder reaction of remisporine ATetrahedron Lett.44(15)3119-3122(2003)
| Cas No. | 571194-06-4 | SDF | |
| Canonical SMILES | COC([C@]12[C@]3([H])[C@](C4=C(OC5=CC(C)=CC(O)=C5C4=O)C[C@@]3([H])[C@](O)(O2)C(OC)=O)([H])C6=C1C(C7=C(O)C=C(C)C=C7O6)=O)=O | ||
| 分子式 | C30H24O12 | 分子量 | 576.5 |
| 溶解度 | 储存条件 | -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 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 1.7346 mL | 8.673 mL | 17.3461 mL |
| 5 mM | 0.3469 mL | 1.7346 mL | 3.4692 mL |
| 10 mM | 0.1735 mL | 0.8673 mL | 1.7346 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。
Absolute configuration of remisporines A & B
Org Biomol Chem 2015 Apr 14;13(14):4169-73.PMID:25735997DOI:10.1039/c5ob00082c.
The absolute configuration of Remisporine B was determined based on a comparison of experimental and calculated electronic circular dichroism (ECD) spectra. Density functional theory (DFT) was used to calculate the ECD spectra varying the parameter controlling the number of calculated electronic transitions. Mapping the reaction surface provided support for the proposed Diels-Alder dimerization of remisporine A to form Remisporine B.
Rare Chromones from a Fungal Mutant of the Marine-Derived Penicillium purpurogenum G59
Mar Drugs 2015 Aug 18;13(8):5219-36.PMID:26295241DOI:10.3390/md13085219.
Three new and rare chromones, named epiremisporine B (2), epiremisporine B1 (3) and isoconiochaetone C (4), along with three known Remisporine B (1), coniochaetone A (5) and methyl 8-hydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate (6) were isolated from a mutant from the diethyl sulfate (DES) mutagenesis of a marine-derived Penicillium purpurogenum G59. The structures of 2-4 including the absolute configurations were determined by spectroscopic methods, especially by NMR analysis and electronic circular dichroism (ECD) experiments in conjunction with calculations. The absolute configuration of the known Remisporine B (1) was determined for the first time. Compounds 2 and 3 have a rare feature that has only been reported in one example so far. The compounds 1-6 were evaluated for their cytotoxicity against several human cancer cell lines. The present work explored the great potential of our previous DES mutagenesis strategy for activating silent fungal pathways, which has accelerated the discovery of new bioactive compounds.
WYE-120318, a ring contraction product of methylnaltrexone, and structure revision of coniothyrione
Magn Reson Chem 2012 Dec;50(12):829-33.PMID:23135875DOI:10.1002/mrc.3892.
A contracted ring degradation product, WYE-120318 (compound 2), was discovered during the development phase for methylnaltrexone bromide (compound 1) drug substance. The compound was isolated by high-performance liquid chromatography fractionation, and its structure was determined by spectroscopic data analyses. WYE-120318 is formed from methylnaltrexone through a benzyl-benzilic acid type rearrangement reaction to yield an α-hydroxy-cyclopentanecarboxylic acid substructure. The proposed structure and the formation mechanism are confirmed by the synthesis of WYE-120318 from methylnaltrexone (compound 1). A similar benzyl-benzilic acid type rearrangement reaction can be envisioned as the biological origin of remisporine A (compound 3), a naturally occurring cyclopentadienyl compound that autocatalytically dimerizes to Remisporine B (compound 4). The structure of remisporine A was deduced from its dimer 4. Coniothyione (compound 5) can be considered as the first example of a stable natural product bearing the remisporine A skeleton. However, the regiochemistry of the chlorosubstitution in the coniothyrione structure needs to be revised to compound 6 on the basis of the nuclear magnetic resonance data and biogenesis analysis.