Sophoranone A and B: two new cytotoxic prenylated metabolites and their analogs from the root bark of Sophora flavescens

Abstract Sophora flavescens Ait. has been utilized as an anticarcinogen, antibacterial and insecticide. Two new prenylflavonoids, Sophoflavonoid A (1) and Sophoflavonoid B (2), together with four known analogues were isolated from the root bark of S. flavescens. The structures of these compounds were elucidated by the interpretation of spectroscopic data and chemical evidence. Their absolute configurations were determined by ECD analysis. The inhibitory effects of compounds 1–6 against three lung carcinoma cells were determined using the MTT assay. The results revealed that compound 3 displayed strong cytotoxic effect against H460 cell line (IC50, 4.67 μM), while compounds 1, 4–6 exhibited significant inhibitory effects against three tumor cells. Therefore, this study suggests that the isopentenyl flavonoid-rich products of S. flavescens, including the new compounds, could be valuable candidates for the development of pharmaceuticals in the prevention and treatment for tumors. GRAPHICAL ABSTRACT

[1]  Zhi‐Jun Zhang,et al.  Quinolizidine alkaloids from the roots of Sophora flavescens , 2020, Natural product research.

[2]  Anhua Wang,et al.  Chemical constituents of Sophora flavescens Ait. and cytotoxic activities of two new compounds , 2020, Natural product research.

[3]  Luo-wei Yuan,et al.  Cytotoxic effects of flavonoids from root of Sophora flavescens in cancer cells , 2020, Natural product research.

[4]  V. Pham,et al.  Antimicrobial Lavandulylated Flavonoids from a Sponge-Derived Streptomyces sp. G248 in East Vietnam Sea , 2019, Marine drugs.

[5]  V. Pham,et al.  Antimicrobial lavandulylated flavonoids from a sponge-derived actinomycete , 2018, Natural product research.

[6]  Shu-Chen Cheng,et al.  Fisetin inhibits the generation of inflammatory mediators in interleukin‐1&bgr;–induced human lung epithelial cells by suppressing the NF‐&kgr;B and ERK1/2 pathways , 2018, International immunopharmacology.

[7]  Lei Chen,et al.  A new flavonoid from Sophora flavescens Ait. , 2017, Natural product research.

[8]  H. Oh,et al.  Protein Tyrosine Phosphatase 1B Inhibitors from the Roots of Cudrania tricuspidata , 2015, Molecules.

[9]  Li Huang,et al.  Identification and synthesis of quinolizidines with anti-influenza a virus activity. , 2014, ACS medicinal chemistry letters.

[10]  J. Choi,et al.  Antidiabetic complications and anti‐alzheimer activities of sophoflavescenol, a prenylated flavonol from Sophora flavescens, and its structure–activity relationship , 2011, Phytotherapy research : PTR.

[11]  L. Yu,et al.  Anti-Inflammatory and antiproliferative activities of trifolirhizin, a flavonoid from Sophora flavescens roots. , 2009, Journal of agricultural and food chemistry.

[12]  Ik-Soo Lee,et al.  Microbial metabolites of 8-prenylnaringenin, an estrogenic prenylflavanone , 2008, Archives of pharmacal research.

[13]  Chenggang Huang,et al.  Antiviral effects of sophoridine against coxsackievirus B3 and its pharmacokinetics in rats. , 2006, Life sciences.

[14]  M. Wink,et al.  Binding of Flavonoids from Sophora flavescens to the Rat Uterine Estrogen Receptor , 2005, Planta medica.

[15]  M. Boyd,et al.  Anti-HIV Prenylated Flavonoids from Monotes africanus1 , 2001 .

[16]  M. Boyd,et al.  Anti-HIV prenylated flavonoids from Monotes africanus. , 2001, Journal of natural products.

[17]  T Hayashi,et al.  Antibacterial and antiandrogen flavonoids from Sophora flavescens. , 1999, Journal of natural products.

[18]  Y. Shirataki,et al.  Studies on the Constituents of Sophora Species. XXIII. : Constituents of the Root of Sphora chrysophylla SEEM. (1) , 1990 .

[19]  Y. Shirataki,et al.  Studies on the Constituents of Sophora Species. XXII. : Constituents of the Root of Sophora moorcroftiang BENTH. ex BAKER. (1) , 1988 .