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Kushenol A Sale

(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。

Kushenol A Chemical Structure

Cas No.:99217-63-7

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产品描述

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.

Chemical Properties

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
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Research Update

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.