Sophoflavescenol
(Synonyms: 槐苦参醇) 目录号 : GC33067
Sophoflavescenol是一种异戊烯基黄酮类化合物，能够抑制PDE5的活性，IC50值为0.013μM；同时抑制RLAR，HRAR，BACE1，AChE和BChE，IC50值分别为0.30µM，0.17µM，10.98µM，8.37µM和8.21µM。
Cas No.:216450-65-6
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
Kinase experiment: | Briefly, a mixture of 10 µL of assay buffer (50 mm sodium acetate, pH 4.5), 10 µL of BACE1 (1.0 U/mL), 10 µL of the substrate (750 nm Rh-EVNLDAEFK-Quencher in 50 mm, ammonium bicarbonate) and 10 µL of the tested samples [final concentration (f.c.) 100 µM for compounds] dissolved in 10% DMSO is incubated for 60 min at 25°C in the dark. The proteolysis of two fluorophores (Rh-EVNLDAEFK-Quencher) by BACE1 is monitored by formation of the fluorescent donor (Rh-EVNL) that increased in fluorescence wavelengths at 530-545 nm (excitation) and 570-590 nm (emission), respectively. Fluorescence is measured with a microplate spectrofluorometer. The mixture is irradiated at 545 nm and the emission intensity recorded at 585 nm. The percent inhibition (%) is obtained by the following equation: % Inhibition=[1 − (S60 − S0)/(C60 − C0)] × 100, where C60 is the fluorescence of the control (enzyme, buffer, substrate) after 60 min of incubation, C0 the initial fluorescence of the control, S60 the fluorescence of the tested samples (enzyme, sample solution, substrate) after 60 min of incubation, and S0 the initial fluorescence of the tested samples. To allow for the quenching effect of the samples, the sample solution is added to reaction mixture C, and any reduction in fluorescence by the sample is then investigated. The BACE1 inhibitory activity of each sample is expressed in terms of the IC50 value (µM required to inhibit proteolysis of the BACE1 substrate, by 50%), as calculated from the log-dose inhibition curve. |
References: [1]. Jung HA, et al. Anti-tumorigenic activity of sophoflavescenol against Lewis lung carcinoma in vitro and in vivo. Arch Pharm Res. 2011 Dec;34(12):2087-99 | |
Sophoflavescenol is a prenylated flavonol, which shows great inhibitory activity with IC50 of 0.013 μM against Phosphodiesterase 5 (PDE5), and also inhibits RLAR, HRAR, AGE, BACE1, AChE and BChE with IC50s of 0.30 µM, 0.17 µM, 17.89 µg/mL, 10.98 µM, 8.37 µM and 8.21 µM, respectively.
Sophoflavescenol shows cytotoxicity against human leukaemia (HL-60), Lewis lung carcinoma (LLC), and human lung adenocarcinoma epithelial (A549) cells. Sophoflavescenol exerts notable anti-inflammatory activity by inhibiting nitric oxide generation and tert-butylhydroperoxide-induced ROS generation rather than inhibiting nuclear factor kappa B activation in RAW 264.7 cells[1]. Sophoflavescenol exhibits remarkable inhibition of RLAR activity with an IC50 value of 0.30 µM, compared with 0.07 µM for epalrestat, a well known ARI. Sophoflavescenol also shows potent inhibitory activity with an IC50 value of 0.17 µM, comparable to epalrestat (0.15 µM) in the HRAR assay. In the AGE assay, sophoflavescenol (IC50 17.89 µg/mL) is a more potent inhibitor of AGE formation than aminoguanidine (IC50 81.05 µg/mL). Sophoflavescenol exerts both potent AChE and BChE inhibitory effects with respective IC50 values of 8.37 and 8.21 µM. Sophoflavescenol also exhibits good BACE1 inhibition in a dose-dependent manner with an IC50 value of 10.98 µM[2]. Sophoflavescenol is a mixed inhibitor (Ki=0.005 μM) against cGMP PDE5. Sophoflavescenol shows greatest selectivity toward PDE5, 31.5- and 196.2-fold over PDE3 and PDE4, respectively[3].
Sophoflavescenol exerts potent in vivo antitumor activity by tumor growth inhibition in the LLC tumor model as well as apoptotic activity by caspase-3 activation in HL-60 cells[1].
[1]. Jung HA, et al. Anti-tumorigenic activity of sophoflavescenol against Lewis lung carcinoma in vitro and in vivo. Arch Pharm Res. 2011 Dec;34(12):2087-99. [2]. Jung HA, et al. Antidiabetic complications and anti-Alzheimer activities of sophoflavescenol, a prenylated flavonol from Sophora flavescens, and its structure-activity relationship. Phytother Res. 2011 May;25(5):709-15. [3]. Shin HJ, et al. A prenylated flavonol, sophoflavescenol: a potent and selective inhibitor of cGMP phosphodiesterase 5. Bioorg Med Chem Lett. 2002 Sep 2;12(17):2313-6.
| Cas No. | 216450-65-6 | SDF | |
| 别名 | 槐苦参醇 | ||
| Canonical SMILES | O=C1C(O)=C(C2=CC=C(O)C=C2)OC3=C(C/C=C(C)\C)C(O)=CC(OC)=C13 | ||
| 分子式 | C21H20O6 | 分子量 | 368.38 |
| 溶解度 | Soluble in DMSO | 储存条件 | 4°C, away from moisture and 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 | 2.7146 mL | 13.5729 mL | 27.1459 mL |
| 5 mM | 0.5429 mL | 2.7146 mL | 5.4292 mL |
| 10 mM | 0.2715 mL | 1.3573 mL | 2.7146 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。
Anti-tumorigenic activity of Sophoflavescenol against Lewis lung carcinoma in vitro and in vivo
Arch Pharm Res 2011 Dec;34(12):2087-99.PMID:22210035DOI:10.1007/s12272-011-1212-y.
This study examined the in vitro cytotoxic activity and in vivo antitumor activity as well as intracellular apoptotic capacities of a prenylated flavonol, Sophoflavescenol from Sophora flavescens, to evaluate prospective anti-tumorigenic drugs, and antitumor potential. In addition, the in vitro antioxidant and anti-inflammatory capacities were evaluated. Despite the small effect on human breast adenocarcinoma (MCF-7), Sophoflavescenol showed cytotoxicity against human leukaemia (HL-60), Lewis lung carcinoma (LLC), and human lung adenocarcinoma epithelial (A549) cells. Interestingly, it also exerted potent in vivo antitumor activity by tumor growth inhibition in the LLC tumor model as well as apoptotic activity by caspase-3 activation in HL-60 cells. In addition, it exhibited potent antioxidant activities in 1,1-diphenyl-2-picrylhydrazyl, 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt radicals and lipid peroxidation assays. Sophoflavescenol exerted notable anti-inflammatory activity by inhibiting nitric oxide generation and tert-butylhydroperoxide-induced ROS generation rather than inhibiting nuclear factor kappa B activation in RAW 264.7 cells. The findings show that the antioxidant, anti-inflammatory, and apoptotic activities of Sophoflavescenol might contribute to the antitumor activity without severe side effects, highlighting its potential for chemoprevention and/or anticancer drugs due to multi-effective targets in almost all stages of tumorigenesis, including initiation, promotion, and progression.
Biologically active prenylated flavonoids from the genus Sophora and their structure-activity relationship-A review
Phytother Res 2019 Mar;33(3):546-560.PMID:30652369DOI:10.1002/ptr.6265.
The genus Sophora (Fabaceae) has been used in traditional medicine for years. Prenylated flavonoids are one of the constituents of Sophora species that play important roles in their biological properties. Different classes of prenylated flavonoids are produced by Sophora spp. including prenylated flavonol (e.g., Sophoflavescenol), prenylated flavanone (e.g., sophoraflavanone G), prenylated flavonostilbene (e.g., alopecurones A and B), and prenylated chalcone (kuraridin). Prenylated flavonoids have a more lipophilic structure, which leads to its high affinity to the cell membranes and enhancement of the biological activity, which includes cytotoxicity, antibacterial, anti-inflammatory, and estrogenic activities. However, it is reported that prenylation decreases the plasma absorption but increases the tissue accumulation. The presence of the prenyl or lavandulyl groups on C8 position of flavonoids plays an important role in the biological activity. It seems that prenylated flavonoids have the potential to be developed as new drugs or supplements for human health.
A prenylated flavonol, Sophoflavescenol: a potent and selective inhibitor of cGMP phosphodiesterase 5
Bioorg Med Chem Lett 2002 Sep 2;12(17):2313-6.PMID:12161123DOI:10.1016/s0960-894x(02)00401-8.
During the search for naturally occurring cyclic guanosine monophosphate (cGMP)-specific phosphodiesterase type 5 (PDE5) inhibitors, it was found that the extracts from Sophora flavescens exhibit potent inhibitory activity against cGMP PDE5 prepared from rat diaphragm. Therefore, the inhibitory activities of five flavonoids, kushenol H (1), kushenol K (2), kurarinol (3), Sophoflavescenol (4) and kuraridine (5), isolated from S. flavescens were measured against cGMP PDE5 to identify potent cGMP PDE5 inhibitory constituents. Among tested compounds, Sophoflavescenol (4), a C-8 prenylated flavonol, showed the most potent inhibitory activity (IC(50)=0.013 microM) against cGMP PDE5 with 31.5- and 196.2-fold selectivity over PDE3 and PDE4, respectively. Kinetic analysis revealed that Sophoflavescenol was a mixed inhibitor of PDE5 with a K(i) value of 0.005 microM.
Antidiabetic complications and anti-Alzheimer activities of Sophoflavescenol, a prenylated flavonol from Sophora flavescens, and its structure-activity relationship
Phytother Res 2011 May;25(5):709-15.PMID:21077260DOI:10.1002/ptr.3326.
It was previously reported that prenylated flavonols from Sophora flavescens are inhibitors of rat lens aldose reductase (RLAR), human recombinant aldose reductase (HRAR), advanced glycation endproducts (AGE), β-secretase (BACE1) and cholinesterases (ChE). Based upon structure-activity relationships, 3,4'-dihydroxy flavonols with a prenyl or lavandulyl group substitution at the C-8 position, and a hydroxy group at the C-5, are important for such inhibition. In our ongoing study to isolate active principles from S. flavescens by an activity-guided isolation procedure, further detailed phytochemical investigations of the CH(2)Cl(2) fraction were conducted via repeated chromatography over silica gel and Sephadex LH-20 columns. This ultimately resulted in the isolation of a promising active Sophoflavescenol with higher inhibitory activities among the current prenylated flavonols isolated from S. flavescens against RLAR, HRAR, AGE, BACE1 and ChEs. The results further support that 3,4'-dihydroxy flavonols with a prenyl or lavandulyl substitution at the C-8 position and a methoxy group at C-5 represent a new class of RLAR, HRAR and AGE inhibitors. Nevertheless, the C-5 hydroxyl group of prenylated flavonoids is important for inhibition of BACE1 and ChEs, indicating that the hydroxyl group at C-5 might be the main contributor to the augmentation and/or modification of prenylated flavonol activity.
Selectively recognizing heptad-interfaced G-quadruplexes by a molecular rotor with an ESIPT emission
Chem Commun (Camb) 2023 Jan 26;59(9):1189-1192.PMID:36629144DOI:10.1039/d2cc06156b.
Heptad-interfaced G-quadruplexes (G4s), formed with GGA repeats located in the nuclear proto-oncogene c-myb promoter, can be selectively targeted by a prenylated flavonol of Sophoflavescenol (Sop) with restriction of molecular rotation to trigger strong excited state intramolecular proton transfer (ESIPT) emission.