Dihydrosanguinarine (13,14-Dihydrosanguinarine)
(Synonyms: 二氢血根碱; 13,14-Dihydrosanguinarine) 目录号 : GC33965
A metabolite of sanguinarine with diverse biological activities
Cas No.:3606-45-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Dihydrosanguinarine is an alkaloid and a metabolite of the alkaloid sanguinarine that has diverse biological activities, including anticancer, fungicidal, and antiprotozoal properties.1,2,3 It inhibits proliferation of PANC-1, SW 1990, and HPDE6c7 cancer cells when used at concentrations of 10, 20, and 30 ?M.1 It also reduces the levels of phosphorylated ERK and C-RAF, halts the cell cycle at the G0/G1 and G2/M phases, and induces apoptosis in PANC-1 cells. Dihydrosanguinarine inhibits spore germination of the phytopathogenic fungi B. cinerea and E. graminis in vitro (EC50s = 56.35 and 95.75 ?g/ml, respectively).2 It has protective and curative effects against B. cinerea and E. graminis when applied as a spray to plants either before or after infection, respectively, at concentrations of 100 and 500 ?g/ml. Dihydrosanguinarine is also effective against I. multifiliis infestation in S. curriculus (EC50 = 5.18 mg/L) with an LC50 value of 13.3 mg/L.3
1.Wu, S.-Z., Xu, H.-C., Wu, X.-L., et al.Dihydrosanguinarine suppresses pancreatic cancer cells via regulation of mut-p53/WT-p53 and the Ras/Raf/Mek/Erk pathwayPhytomedicine59152895(2019) 2.Feng, G., Zhang, J., and Liu, Y.-Q.Inhibitory activity of dihydrosanguinarine and dihydrochelerythrine against phytopathogenic fungiNat. Prod. Res.25(11)1082-1089(2011) 3.Yao, J.-Y., Zhou, Z.-M., Li, X.-L., et al.Antiparasitic efficacy of dihydrosanguinarine and dihydrochelerythrine from Macleaya microcarpa against Ichthyophthirius multifiliis in richadsin (Squaliobarbus curriculus)Vet. Parasitol.183(1-2)8-13(2011)
| Cas No. | 3606-45-9 | SDF | |
| 别名 | 二氢血根碱; 13,14-Dihydrosanguinarine | ||
| Canonical SMILES | CN1C2=C(C=C(OCO3)C3=C4)C4=CC=C2C5=CC=C6C(OCO6)=C5C1 | ||
| 分子式 | C20H15NO4 | 分子量 | 333.34 |
| 溶解度 | DMSO : 5.2 mg/mL (15.60 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 | 2.9999 mL | 14.9997 mL | 29.9994 mL |
| 5 mM | 0.6 mL | 2.9999 mL | 5.9999 mL |
| 10 mM | 0.3 mL | 1.5 mL | 2.9999 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。
Antiparasitic efficacy of Dihydrosanguinarine and dihydrochelerythrine from Macleaya microcarpa against Ichthyophthirius multifiliis in richadsin (Squaliobarbus curriculus)
Vet Parasitol 2011 Dec 29;183(1-2):8-13.PMID:21813242DOI:10.1016/j.vetpar.2011.07.021.
Ichthyophthirius multifiliis is a holotrichous protozoan that invades the gills and skin surfaces of fish and can cause morbidity and high mortality in most species of freshwater fish worldwide. The present study was undertaken to investigate the antiparasitic activity of crude extracts and pure compounds from the leaves of Macleaya microcarpa. The chloroform extract showed a promising antiparasitic activity against I. multifiliis. Based on these finding, the chloroform extract was fractionated on silica gel column chromatography in a bioactivity-guided isolation affording two compounds showing potent activity. The structures of the two compounds were elucidated as Dihydrosanguinarine and dihydrochelerythrine by hydrogen and carbon-13 nuclear magnetic resonance spectrum and electron ionization mass spectrometry. The in vivo tests revealed that Dihydrosanguinarine and dihydrochelerythrine were effective against I. multifiliis with median effective concentration (EC(50)) values of 5.18 and 9.43 mg/l, respectively. The acute toxicities (LC(50)) of Dihydrosanguinarine and dihydrochelerythrine for richadsin were 13.3 and 18.2mg/l, respectively. The overall results provided important information for the potential application of Dihydrosanguinarine and dihydrochelerythrine in the therapy of serious infection caused by I. multifiliis.
Mild C(sp3)-H functionalization of Dihydrosanguinarine and dihydrochelerythrine for development of highly cytotoxic derivatives
Eur J Med Chem 2017 Sep 29;138:1-12.PMID:28641156DOI:10.1016/j.ejmech.2017.06.021.
A series of C(6)-substituted dihydrobenzo[c]phenanthridines were synthesized by mild copper-catalyzed C(sp3)-H functionalization of Dihydrosanguinarine (2) and dihydrochelerythrine (3) with certain nucleophiles selected to enhance cytotoxicity against human breast, colorectal, and prostate cancer cell lines. We also investigated the cytotoxicity of our previously reported C(6)-functionalized N-methyl-5,6-dihydrobenzo[c]phenanthridines 1a-1e to perform structure-activity relationship (SAR) studies. Among the target compounds, five β-aminomalonates (1a, 1b, 2a, 2b, and 3b), one α-aminophosphonate (2c), and one nitroalkyl derivative (2h) exhibited half maximal inhibitory concentration (IC50) values in the range of 0.6-8.2 μM. Derivatives 1b, 2b and 2h showed the lowest IC50 values, with 2b being the most potent with values comparable to those of the positive control doxorubicin. On the basis of their IC50 values, derivatives 1a, 1b, 2a, 2b, 2h, and 3b were selected to evaluate the apoptotic PC-3 cell death at 10 μM by flow cytometry using propidium iodide and fluorescein isothiocyanate-conjugated Annexin V dual staining. The results indicated that the cytotoxic activity of the tested compounds in PC-3 cells is due to the induction of apoptosis, with 1a and 2h being the most active (55% of early apoptosis induction). Our preliminary SAR study showed that the incorporation of specific malonic esters, dialkyl phosphites and nitro alkanes on scaffolds 1-3 significantly enhanced their cytotoxic properties. Moreover, it appears that the electron donating 7,8-methylenedioxy group allowed derivatives of 2 to exhibit higher cytotoxicity than derivatives of 1 and 3. The present results suggest that derivatives 2b and 2h may be considered as potential lead compounds for the development of new anticancer agents.
Molecular cloning and characterization of a cytochrome P450 in sanguinarine biosynthesis from Eschscholzia californica cells
Phytochemistry 2013 Jul;91:100-8.PMID:22421633DOI:10.1016/j.phytochem.2012.02.013.
Benzophenanthridine alkaloids, such as sanguinarine, are produced from reticuline, a common intermediate in benzylisoquinoline alkaloid biosynthesis, via protopine. Four cytochrome P450s are involved in the biosynthesis of sanguinarine from reticuline; i.e. cheilanthifoline synthase (CYP719A5; EC 1.14.21.2.), stylopine synthase (CYP719A2/A3; EC 1.14.21.1.), N-methylstylopine hydroxylase (MSH) and protopine 6-hydroxylase (P6H; EC 1.14.13.55.). In this study, a cDNA of P6H was isolated from cultured Eschscholzia californica cells, based on an integrated analysis of metabolites and transcript expression profiles of transgenic cells with Coptis japonica scoulerine-9-O-methyltransferase. Using the full-length candidate cDNA for P6H (CYP82N2v2), recombinant protein was produced in Saccharomyces cerevisiae for characterization. The microsomal fraction containing recombinant CYP82N2v2 showed typical reduced CO-difference spectra of P450, and production of Dihydrosanguinarine and dihydrochelerythrine from protopine and allocryptopine, respectively. Further characterization of the substrate-specificity of CYP82N2v2 indicated that 6-hydroxylation played a role in the reaction.
Chemical Study of Alkaloids from Corydalis bungeana
Planta Med 1987 Oct;53(5):418-20.PMID:17269058DOI:10.1055/s-2006-962761.
From the herbs of CORYDALIS BUNGEANA, 16 alkaloids were isolated; 3 of them were identical with acetylcorynoline ( 2), corynoline ( 5), protopine ( 9), which had been obtained before from this plant. A further 11 known alkaloids: Dihydrosanguinarine ( 1), acetylisocorynoline ( 3), 11-epicorynoline ( 4), corycavine ( 6), bicuculine ( 7), 12-hydroxycorynoline ( 8), scoulerine ( 12), cheilanthifoline ( 13), yuziphine ( 14), isoboldine ( 15), noryuziphine ( 16) were isolated for the first time from this plant. The tenth, named (+)-bungeanine, is a new alkaloid. Its structure has been established to be N-nor-5,14-dehydroacetylcorynoline. The conformation of (+)-bungeanine in solution is also discussed.
Benzophenanthridine alkaloids from the roots of Thalictrum microgynum Lecoy.ex Oliv
Nat Prod Res 2019 Oct;33(20):2964-2969.PMID:30306799DOI:10.1080/14786419.2018.1512991.
A new benzophenanthridine alkaloid, 2,3,9-trimethoxy-7,8-methylenedioxy-5-methylbenzo[c]-6(5H) phenanthridone (2) and a benzophenanthridine alkaloid first found from natural sources, 2,3-dimethoxy-7,8- methylenedioxy-5-methylbenzo[c]-6(5H)- phenanthridone (1) together with two known benzophenanthridine alkaloids, Dihydrosanguinarine (3) and Dihydrochelilutine (4) were isolated from the roots of Thalictrum microgynum Lecoy.ex Oliv. The structures of 1 and 2 were elucidated using various spectroscopic techniques including HRESIMS and 1 D and 2 D NMR. Antibacterial activity of these compounds were tested. Compound 1, 3 and 4 showed antibacterial activity against Staphylococcus aureus with MIC values of 50, 100, 25 μg/mL, respectively.