Kushenol A
(Synonyms: 苦参新醇A,Leachianone E) 目录号 : GC36402
Kushenol A 是从苦参 (Sophora flavescent) 的根中分离出来的，一种非竞争性酪氨酸酶 (tyrosinase) 抑制剂，IC50 和 Ki 值分别为 1.1 μM 和 0.4 μM。Kushenol A 是一种黄酮类抗氧化剂，对 α-葡萄糖苷酶 (alpha-glucosidase) 和 β-淀粉酶(beta-amylase)具有抑制作用。Kushenol A 被证实是可用于化妆品的针对皮肤美白和衰老的潜在物质。
Cas No.:99217-63-7
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
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- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Kushenol A is isolated from the root of Sophora flavescent, a non-competitive tyrosinase inhibitor with IC50 and Ki values of 1.1 μM and 0.4 μM, respectively[1].Kushenol A is a flavonoid antioxidant, has inhibitory effects on alpha-glucosidase and beta-amylase[2].Kushenol A is confirmed as potential inhibitors of enzymes targeted by cosmetics for skin whitening and aging[1].
[1]. Kim JH, et al. Kushenol A and 8-prenylkaempferol, tyrosinase inhibitors, derived from Sophora flavescens. J Enzyme Inhib Med Chem. 2018 Dec;33(1):1048-1054. [2]. Kim JH, et al. Glycosidase inhibitory flavonoids from Sophora flavescens. Biol Pharm Bull. 2006 Feb;29(2):302-5.
| Cas No. | 99217-63-7 | SDF | |
| 别名 | 苦参新醇A,Leachianone E | ||
| Canonical SMILES | O=C1C[C@@H](C2=CC=CC=C2O)OC3=C(C[C@H](C(C)=C)C/C=C(C)\C)C(O)=CC(O)=C13 | ||
| 分子式 | C25H28O5 | 分子量 | 408.49 |
| 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 | 2.448 mL | 12.2402 mL | 24.4804 mL |
| 5 mM | 0.4896 mL | 2.448 mL | 4.8961 mL |
| 10 mM | 0.2448 mL | 1.224 mL | 2.448 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。
Kushenol A and 8-prenylkaempferol, tyrosinase inhibitors, derived from Sophora flavescens
J Enzyme Inhib Med Chem 2018 Dec;33(1):1048-1054.PMID:29873272DOI:10.1080/14756366.2018.1477776.
Tyrosinase is known for an enzyme that plays a key role in producing the initial precursor of melanin biosynthesis. Inhibition of the catalytic reaction of this enzyme led to some advantage such as skin-whitening and anti-insect agents. To find a natural compound with inhibitory activity towards tyrosinase, the five flavonoids of Kushenol A (1), 8-prenylkaempferol (2), kushenol C (3), formononetin (4) and 8-prenylnaringenin (5) were isolated by column chromatography from a 95% methanol extract of Sophora flavescens. The ability of these flavonoids to block the conversion of L-tyrosine to L-DOPA by tyrosinase was tested in vitro. Compounds 1 and 2 exhibited potent inhibitory activity, with IC50 values less than 10 µM. Furthermore, enzyme kinetics and molecular docking analysis revealed the formation of a binary encounter complex between compounds 1-4 and the enzyme. Also, all of the isolated compounds (1-5) were confirmed to possess antioxidant activity.
A Novel Flavonoid Kushenol Z from Sophora flavescens Mediates mTOR Pathway by Inhibiting Phosphodiesterase and Akt Activity to Induce Apoptosis in Non-Small-Cell Lung Cancer Cells
Molecules 2019 Dec 4;24(24):4425.PMID:31817093DOI:10.3390/molecules24244425.
The roots of Sophora flavescens (SF) are clinically used as a traditional Chinese medicine for the treatment of various lung diseases. In this study, we investigated the mechanism by which SF inhibits proliferation and induces apoptosis in non-small-cell lung cancer (NSCLC) cells. A new compound, kushenol Z (KZ), and 14 known flavonoids were isolated from SF. KZ, sophoraflavanone G, and Kushenol A demonstrated potent cytotoxicity against NSCLC cells in a dose- and time-dependent manner; KZ showed a wide therapeutic window. We also found that KZ induced NSCLC cell apoptosis by increasing the Bax/Bcl-2 ratio and by activating caspase-3 and caspase-9 leading to mitochondrial apoptosis, and upregulated CHOP and activatedcaspase-7 and caspase-12, which triggered the endoplasmic reticulum stress pathway. After KZ treatment, we observed cAMP accumulation, which reflected the inhibition of cAMP-phosphodiesterase (PDE), along with the increase in PKA activity; additionally, phospho-p70 S6 kinase was downregulated. KZ also attenuated the phosphorylation of Akt and PRAS40, which was partially rescued by an Akt activator. This suggested that KZ mediated the antiproliferative activity in NSCLC cells by inhibiting the mTOR pathway through the inhibition of cAMP-PDE and Akt. These findings suggested that KZ may be used as a promising cAMP-PDE and Akt inhibitor in targeted chemotherapeutic drug development.
Flavonoid extract Kushenol A exhibits anti-proliferative activity in breast cancer cells via suppression of PI3K/AKT/mTOR pathway
Cancer Med 2023 Jan;12(2):1643-1654.PMID:35789211DOI:10.1002/cam4.4993.
Background: Kushenol A is natural flavonoid extract discovered in recent years, with potential anti-tumor activity. Its role in breast cancer is poorly understood. Methods: To investigate biological function of Kushenol A in breast cancer (BC), Cell Counting Kit-8 assay, colony formation assay, flow cytometry, western blotting, qPCR analysis, and xenograft mouse model were performed. Results: We found that Kushenol A treatment reduced proliferative capability and induced G0/G1 phase cell cycle arrest and apoptosis of BC cells in a concentration-dependent manner. Besides, Kushenol A treatment contributed to the upregulation of apoptosis-related and cell cycle-associated genes. In nude mice, Kushenol A administration repressed BC xenograft tumor growth. Mechanistically, phosphorylation levels of AKT and mTOR were markedly attenuated in Kushenol A-treated BC cells; however, there were no significant differences in total AKT and mTOR expressions. Moreover, PI3K inhibitor combined with Kushenol A exhibited synergistic inhibitory activity on cell proliferation. Conclusions: Taken together, our findings suggested that Kushenol A suppressed BC cell proliferation by modulating PI3K/AKT/mTOR signaling pathway. Kushenol A may be a promising therapeutic drug for treating BC.
Glycosidase inhibitory flavonoids from Sophora flavescens
Biol Pharm Bull 2006 Feb;29(2):302-5.PMID:16462036DOI:10.1248/bpb.29.302.
The methanol extract of Sophora flavescens showed a potent glycosidase inhibitory activity. Active components were identified as well-known flavonoid antioxidants: Kushenol A (1), (-)-kurarinone (2), sophoraflavanone G (3), 2'-methoxykurarinone (4), kurarinol (5), 8-prenylkaempferol (6), isoxanthohumol (7), kuraridin (8) and maackian (9). All flavonoids were effective inhibitors of alpha-glucosidase and beta-amylase. Interestingly, lavandulylated flavanones 1-5 had strong alpha-glucosidase inhibitory activities, with IC(50) values of 45 microM, 68 microM, 37 microM, 155 microM and 179 microM, respectively. Kushenol A (1) which does not bear a 4'-hydroxy group showed selective alpha-glucosidase inhibitory activity. Lavandulylated chalcone, kuraridine (8), exhibited IC(50) value of 57 microM against beta-glucosidase, which is the first report of a chalcone displaying glycosidase inhibition. Results showed that 8-lavandulyl group in B-ring was a key factor of the glycosidase inhibitory activities. The inhibition pattern was noncompetitive for alpha-glucosidase, whereas mixed inhibition was observed for beta-amylase.
Characterization of flavonoids in the extract of Sophora flavescens Ait. by high-performance liquid chromatography coupled with diode-array detector and electrospray ionization mass spectrometry
J Pharm Biomed Anal 2007 Sep 3;44(5):1019-28.PMID:17658714DOI:10.1016/j.jpba.2007.04.019.
A method coupling high-performance liquid chromatography (HPLC) with diode-array detector (DAD) and electrospray ionization mass spectrometry (ESI) was established for the separation and characterization of flavonoids in Sophora flavescens Ait. Based on the chromatographic separation of most flavonoids present in S. flavescens Ait., a total of 24 flavonoids were identified. Fourteen compounds were unambiguously identified comparing experimental data for retention time (t(R)), UV and MS spectra with those of the authentic compounds: 3',7-dihydroxy-4'-methoxy-isoflavone (13), trifolirhizin (14), kurarinol (18), formononetin (19), 7,4'-dihydroxy-5-methoxy-8-(gamma,gamma-dimethylallyl)-flavanone (22), maackiain (21), isoxanthohumol (23), kuraridine (26), kuraridinol (27), sophoraflavanone G (30), xanthohumol (31), isokurarinone (33), kurarinone (35) and kushenol D (38), and additional 10 compounds were tentatively identified as kushenol O (10), trifolirhizin-6''-malonate (15), sophoraisoflavanone A (20), norkurarinol/kosamol Q (24), kushenol I/N (25), kushenol C (28), 2'-methoxykurarinone (29), kosamol R (32), kushecarpin A (34) and Kushenol A (37) by comparing experimental data for UV and MS spectra with those of literature. Furthermore, fragmentation pathways in positive ions mode of 24 flavonoid compounds of types of flavanone, flavanonol, flavonol, chalcone, isoflavone, isoflavanone and ptercocarpane were summarized. Some common features, such as CH(3)., H(2)O, CO, CO(2), C(3)O(2) and C(2)H(2)O losses, together with Retro-Diels-Alder fragmentations were observed in the prenylated flavonoids in S. flavescens Ait. The loss of the lanandulyl chain was their characteristic fragmentation, which might help deducing the structure of unknown flavonoid compounds. The present study provided an approach to rapidly characterize bioactive constituents in S. flavescens Ait.