Demethylsuberosin
(Synonyms: 7-去甲基软木花椒素; 7-Demethylsuberosin) 目录号 : GC38152
A prenylated coumarin with anti-inflammatory and neuroprotective activities
Cas No.:21422-04-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
7-Demethylsuberosin is a prenylated coumarin that has been found in Angelica tenuissima and has anti-inflammatory and neuroprotective activities.1,2 It inhibits histamine release induced by phorbol 12-myristate 13-acetate and A23187 from HMC-1 human mast cell leukemia cells when used at a concentration of 10 ?M.1 7-Demethylsuberosin (0.1-10 ?M) protects against glutamate-induced cytotoxicity in primary rat cortical cells.2
1.Choi, H.G., Je, I.-G., Kim, G.J., et al.Chemical constituents of the root of Angelica tenuissima and their anti-allergic inflammatory activityNat. Prod. Commun.12(5)779-780(2017) 2.Kang, S.Y., and Kim, Y.C.Neuroprotective coumarins from the root of Angelica gigas: Structure-activity relationshipsArch. Pharm. Res.30(11)1368-1373(2007)
| Cas No. | 21422-04-8 | SDF | |
| 别名 | 7-去甲基软木花椒素; 7-Demethylsuberosin | ||
| Canonical SMILES | O=C1C=CC2=CC(C/C=C(C)\C)=C(O)C=C2O1 | ||
| 分子式 | C14H14O3 | 分子量 | 230.26 |
| 溶解度 | DMSO: 250 mg/mL (1085.73 mM) | 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 | 4.3429 mL | 21.7146 mL | 43.4292 mL |
| 5 mM | 0.8686 mL | 4.3429 mL | 8.6858 mL |
| 10 mM | 0.4343 mL | 2.1715 mL | 4.3429 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。
Elicitor-induced biosynthesis of psoralens in Ammi majus L. suspension cultures. Microsomal conversion of Demethylsuberosin into (+)marmesin and psoralen
Eur J Biochem 1988 Jan 15;171(1-2):369-75.PMID:2828055DOI:10.1111/j.1432-1033.1988.tb13800.x.
Suspension cultures of Ammi majus L. cells produce various linear furanocoumarins in response to treatment with elicitor preparations from either Alternaria carthami Chowdhury or Phytophthora megasperma f.sp. glycinea. Microsomes which were isolated from these cells 14 h after addition of the elicitor efficiently catalyzed the conversion of demethyl [3-14C]suberosin into labelled (+)marmesin in the presence of NADPH and oxygen. In contrast to the chemical cyclization of Demethylsuberosin by m-chloroperoxybenzoic acid, the reaction catalyzed by the marmesin synthase proceeded rapidly and no intermediate Demethylsuberosin epoxide could be recovered. Significant blue-light-reversible inhibition by carbon monoxide and inhibition by various chemicals known to inhibit reactions dependent on cytochrome P450 suggested that the marmesin synthase is a cytochrome-P450-dependent monooxygenase. Upon prolonged incubation, a subsequent major labelled product originated from (+)marmesin, which was identified as psoralen. The psoralen synthase was also characterized as a cytochrome-P450-dependent monooxygenase. Both the marmesin synthase and the psoralen synthase, as well as enzymes catalyzing the formation of Demethylsuberosin and O-prenylumbelliferone from umbelliferone and dimethylallyl diphosphate, were associated with the endoplasmic reticulum in Ammi majus cells and their activities were concomitantly induced by elicitor treatment of the cells. We propose that in vivo these enzymes are active in the lumen of the endoplasmic reticulum from where the furanocoumarin phytoalexins are excreted into the cell culture fluid.
Molecular evolution of parsnip (Pastinaca sativa) membrane-bound prenyltransferases for linear and/or angular furanocoumarin biosynthesis
New Phytol 2016 Jul;211(1):332-44.PMID:26918393DOI:10.1111/nph.13899.
In Apiaceae, furanocoumarins (FCs) are plant defence compounds that are present as linear or angular isomers. Angular isomers appeared during plant evolution as a protective response to herbivores that are resistant to linear molecules. Isomeric biosynthesis occurs through prenylation at the C6 or C8 position of umbelliferone. Here, we report cloning and functional characterization of two different prenyltransferases, Pastinaca sativa prenyltransferase 1 and 2 (PsPT1 and PsPT2), that are involved in these crucial reactions. Both enzymes are targeted to plastids and synthesize osthenol and Demethylsuberosin (DMS) using exclusively umbelliferone and dimethylallylpyrophosphate (DMAPP) as substrates. Enzymatic characterization using heterologously expressed proteins demonstrated that PsPT1 is specialized for the synthesis of the linear form, Demethylsuberosin, whereas PsPT2 more efficiently catalyses the synthesis of its angular counterpart, osthenol. These results are the first example of a complementary prenyltransferase pair from a single plant species that is involved in synthesizing defensive compounds. This study also provides a better understanding of the molecular mechanisms governing the angular FC biosynthetic pathway in apiaceous plants, which involves two paralogous enzymes that share the same phylogenetic origin.
Chemical Constituents of the Root of Angelica tenuissima and their Anti-allergic Inflammatory Activity
Nat Prod Commun 2017 May;12(5):779-780.PMID:30496664doi
A phthalide, levistolide A (1), and six coumarins, Demethylsuberosin (2), fraxetin (3), (-)-marmesinin (4), 3'(S)-O-P-D-glucopyranosyl-3',4'-dihydroxanthyletin (5), 3'(R)-O-P-D-glucopyranosyl-3',4'-dihydroxanthyletin (6), and isopraeroside IV (7) were isolated from the methanolic extract of the roots of Angelica tenuissima Nakai. Their chemical structures were confirmed by comparing spectroscopic and reported data. All seven compounds were isolated for the first time from this plant source. The anti-allergic activities of compounds 1-7 were examined using human mast cells, and compounds 1-3 at 10 liM potently suppressed IL-6 expression and inhibited histamine release from human mast cells by more than 30%.
A coumarin-specific prenyltransferase catalyzes the crucial biosynthetic reaction for furanocoumarin formation in parsley
Plant J 2014 Feb;77(4):627-38.PMID:24354545DOI:10.1111/tpj.12409.
Furanocoumarins constitute a sub-family of coumarin compounds with important defense properties against pathogens and insects, as well as allelopathic functions in plants. Furanocoumarins are divided into two sub-groups according to the alignment of the furan ring with the lactone structure: linear psoralen and angular angelicin derivatives. Determination of furanocoumarin type is based on the prenylation position of the common precursor of all furanocoumarins, umbelliferone, at C6 or C8, which gives rise to the psoralen or angelicin derivatives, respectively. Here, we identified a membrane-bound prenyltransferase PcPT from parsley (Petroselinum crispum), and characterized the properties of the gene product. PcPT expression in various parsley tissues is increased by UV irradiation, with a concomitant increase in furanocoumarin production. This enzyme has strict substrate specificity towards umbelliferone and dimethylallyl diphosphate, and a strong preference for the C6 position of the prenylated product (Demethylsuberosin), leading to linear furanocoumarins. The C8-prenylated derivative (osthenol) is also formed, but to a much lesser extent. The PcPT protein is targeted to the plastids in planta. Introduction of this PcPT into the coumarin-producing plant Ruta graveolens showed increased consumption of endogenous umbelliferone. Expression of PcPT and a 4-coumaroyl CoA 2'-hydroxylase gene in Nicotiana benthamiana, which does not produce furanocoumarins, resulted in formation of Demethylsuberosin, indicating that furanocoumarin production may be reconstructed by a metabolic engineering approach. The results demonstrate that a single prenyltransferase, such as PcPT, opens the pathway to linear furanocoumarins in parsley, but may also catalyze the synthesis of osthenol, the first intermediate committed to the angular furanocoumarin pathway, in other plants.
Synergistic anti-colon cancer effect of glycyrol and butyrate is associated with the enhanced activation of caspase-3 and structural features of glycyrol
Food Chem Toxicol 2020 Feb;136:110952.PMID:31712101DOI:10.1016/j.fct.2019.110952.
Coumarin-based anti-cancer agents have attracted considerable attention recently. Butyrate, a major short-chain fatty acid produced in colon by gut microbiota, has been shown to exert anticancer activity both in vitro and in vivo. In this study, we evaluated the anti-cancer effect of combining glycyrol (GC), a representative of coumarin compounds in licorice, or its analogues Glycycoumarin/Demethylsuberosin/Coumestrol (GCM/De/Coum) with butyrate in HT29 and HCT116 cells, and explored the relationship between the combined anti-cancer effect and structural features of coumarin compounds. Results showed the strongest inhibitory effect on cancer cells was induced by GC/butyrate combination via enhanced activation of caspase-3. Our data indicated the benzofuranyl, isopentenyl and methoxy groups presented in GC played critical role in its anti-cancer activity, while the furan group led to the further enhancement. The findings of the present study will be beneficial for developing coumarin-based compounds and coumarin compound-based regimen to fight against colon cancer.