Alopecurone A

High-Speed Counter-Current Chromatography with an Online Storage Technique for the Preparative Isolation and Purification of Dihydroflavonoids from Sophora alopecuroides L.[Pubmed:28589595]

Phytochem Anal. 2017 Nov;28(6):496-504.

INTRODUCTION: High-speed counter-current chromatography (HSCCC) is an efficient and non-absorption separation technique, but limitations still exist in simultaneous isolation of complex structures of natural products. Moreover, particular methods are various for different kinds of natural products. OBJECTIVE: A novel HSCCC strategy combined with an online storage recycling elution (OSR-CCC) technique was developed for the quick separation of naturally occurring dihydroflavonoids from the extract of the herb Sophora alopecuroides L. METHODOLOGY: In the separation procedure, a storage loop and two six-port valves were connected to a HSCCC system. Effluent A was subjected to an online storage loop and then to recycling separation three times after effluent B was collected in head-to-tail mode. After completion of the recycling separation of effluent A, the elution was switched to tail-to-head mode to collect effluent C. A biphasic solvent system of n-hexane/ethyl acetate/methanol/water (9:6:6:8, v/v/v/v) was used as the separation solvent during the whole elution. RESULTS: Six constituents were isolated simultaneously from the extract (200 mg) of S. alopecuroides by running HSCCC non-stop, and their purities were higher than 95.0%. Their structures were determined as the pterocarpan glycoside sophoratonkin (1) (10.0 mg) and five dihydroflavonoids, alopecurone F (2) (5.4 mg), lehmannin (3) (11.0 mg), Alopecurone A (4) (35.0 mg), sophoraflavanone G (5) (21.0 mg), alopecurone B (6) (31.0 mg). CONCLUSION: This recycling HSCCC method combined with an online storage technique could be a rapid, effective and simple approach to isolate stilbene-dihydroflavonoids from herbs of the Sophora genus simultaneously. Copyright (c) 2017 John Wiley & Sons, Ltd.

Dereplication of cytotoxic compounds from different parts of Sophora pachycarpa using an integrated method of HPLC, LC-MS and (1)H-NMR techniques.[Pubmed:27696895]

Nat Prod Res. 2017 Jun;31(11):1270-1276.

Sophora pachycarpa Schrenk ex C.A.Mey. is an annual plant belonging to the family Fabaceae. The cytotoxic activities of methanol-dichloromethane extracts (1:1) of different parts of S. pachycarpa were investigated on DU145 (prostate cancer cell line) and MCF-7 (breast cancer cell line) cell lines. The root extract of S. pachycarpa was the only extract that showed significant cytotoxic activity with IC50 values of 39.88 and 16.49 mug/mL on DU145 and MCF-7 cell lines, respectively. The root extract was then subjected to RP-HPLC for further fractionations. Among the isolated fractions from root extract, only one of them had remarkable cytotoxic effects with IC50 value of 26.43 on MCF-7 and 7.54 mug/mL on DU145 cell lines. Further purification led to isolation of a compound with IC50 values of 5.44 and 2.44 mug/mL on MCF-7 and DU145 cell lines, respectively. Based on (1)H NMR and (13)C NMR spectra, together with LC-MS, the structure of the purified compound was assigned as the flavonostilbene Alopecurone A.

Flavonostilbenes from Sophora alopecuroides L. as multidrug resistance associated protein 1 (MRP1) inhibitors.[Pubmed:24956120]

Nat Prod Res. 2014;28(23):2195-8.

Flavonoids have always attracted much attention due to their reversal activity on multidrug resistance (MDR). Eight flavonoids isolated from traditional Chinese medicine Sophora alopecuroides L. were applied to test their effect on MDR associated protein 1 (MRP1) through the established predicting assay. Three flavonostilbenes (Alopecurone A, B and D) were first found exhibiting potent inhibitory activity on MRP1. All of them dramatically increased 6-carboxyfluorescein diacetate and doxorubicin accumulation in MRP1-transfected U-2 OS cells. The compounds significantly increased the cytotoxicity and decreased the IC(5)(0) value of doxorubicin on the MDR cells (12-, 5- and 8-fold, respectively) at a non-toxic concentration (20 muM). Besides, Q-PCR analysis reveals that the MRP1 mRNA level in U-2 OS/MRP1 was also markedly decreased by the three compounds. These findings indicate a new therapeutic role of the herb. The three flavonostilbenes may have the possibility for further development as novel therapeutic reversal agents against MDR.

Antibacterial activity of flavanostilbenes against methicillin-resistant Staphylococcus aureus.[Pubmed:7576511]

Lett Appl Microbiol. 1995 Oct;21(4):219-22.

Three phytochemical compounds (Alopecurone A-C), flavanostilbenes which are produced by condensation between a hydroxyflavanone and a hydroxystilbene, were isolated as major components from the root of Sophora alopecuroides. They uniformly inhibited the growth of 21 strains of methicillin-resistant Staphylococcus aureus with minimum inhibitory concentrations of 3.13-6.25 micrograms ml-1.