Two New Antibacterial Flavanones from Sophoraflavescens

The dry root of Sophora flavescens, which is a well-known Chinese herbal medicine, has been used for the treatment of diarrhea, gastrointestinal hemorrhage and eczema1. Here we report the structure elucidation of two new flavanones isolated from this plan…     

Two New Isoprenoid Flavonoids from Sophora flavescens with Antioxidant and Cytotoxic Activities

Sophora flavescens is a regularly used traditional Chinese medicine. In an attempt to discover adequate active agents, the isoprenoid flavonoids from S. flavescens were further investigated. In this work, two new compounds (1–2, kurarinol A-B) together with 26 known ones (3–28) were isolated and elucidated on the basis of extensive NMR, UV and MS analyses. Furthermore, the antioxidant activity of all constituents was assessed through ABTS, PTIO and DPPH methodologies and also were evaluated for cytotoxic activity by three tumor cell lines (HepG2, A549 and MCF7) and one human normal cell line (LO2 cells). As a result, a multitude of components revealed significant inhibitory activity. In particular, compound 1–2 (kurarinol A-B), two new flavanonols derivatives, exhibited the most potent ABTS inhibitory activity with IC₅₀ of 1.21 µg/mL and 1.81 µg/mL, respectively. Meanwhile, the new compound 1 demonstrated remarkable cytotoxicity against three cancer cells lines with IC₅₀ values ranging from 7.50–10.55 μM but showed little effect on the normal cell. The two new isoprenoid flavonoids could be promising antioxidant and anti-tumor nature agents.     

Structural determination of flavonoids from Sophora flavescens

Eight flavonoids were isolated from Sophora flavescens. Among them, three prenylflavanones: (2S)-6[2(3-hydroxyisopropyl)-5-methyl-4-hexenyl]-5-methoxy-7,2', 4'-trihydroxyflavanone (1), (2S)-5, 4'-dimethoxy-8-lavandulyl-7, 2'-dihydroxy flavanone (2) and (2S)-8-(5-hydroxy-2-isopropenyl-5-methylhexyl)-7-methoxy-5,2', 4'-trihydroxyflavanone (3) are new compounds. Their chemical structures were determined by spectral methods including 2D NMR.     

Determination of quinolizidine alkaloids in Sophora flavescens and its preparation using capillary electrophoresis

A simple and accurate capillary electrophoresis method was developed for the determination of four quinolizidine alkaloids in Sophora flavescens and Kuhuang injection. Optimum separation of the analytes was obtained on a 65 cm x 75 microm i.d. uncoated fused-silica capillary using a aqueous buffer system of 60 mmol L(-1) sodium borate at pH 8.5, with applied voltage and capillary temperature of 12 kV and 25 degrees C, respectively. Detection wavelength was set at 204 nm and jatrorrhizine was used as the internal standard. Good linear relationships between peak-area ratios and concentrations of the analytes were observed over the concentration range 0.044-0.792 mg mL(-1) for matrine, 0.142-1.926 mg mL(-1) for oxymatrine, 0.0377-0.3393 mg mL(-1) for sophocarpine and 0.0664-1.062 mg mL(-1) for sophoridine. The recoveries of four alkaloids ranged between 93.08 and 101.4% with relative standard deviations from 0.7 to 9.2% (n = 6) as determined by standard addition. The limits of detection for four alkaloids were determined to be over the range 8.8-48.0 microg mL(-1). Contents of four alkaloids in Sophora flavescens and three alkaloids in Kuhuang injection were successfully determined under the optimum conditions.     

LC-MS characterization of efficacy substances in serum of experimental animals treated with Sophora flavescens extracts

Anti-DHBV (duck hepatitis B virus) activity was found in the aqueous extracts of Sophora flavescens Ait. in vivo. Liquid chromatography/electrospray ionization ion trap mass spectrometry was applied to characterize the components in duck serum after oral administration of S. flavescens extract. Oxymatrine (1), sophoranol (2), sophoridine (3) and matrine (4) were identified in the serum. Further research on the four compounds was evaluated for their antiviral activity against HBV (hepatitis B virus) in cell culture. The results suggested that oxymatrine, sophoranol and matrine were the efficacy substances for anti-HBV activity in aqueous extracts of S. flavescens Ait.     

秦岭苦参中苦参碱立体异构体晶体结构研究

从秦岭地区苦参中经过溶剂提取和酸化分离得到一种生物碱盐酸盐结晶1，该 晶体不对称单元含有一对新的苦参碱非对映异构体，绝对构型分别是1S，5S6S， 7R，11R，16S和1S，5S，6S，7R，11R，16R，命名为顺式新苦参碱(cis- neomatrine)和反式新苦参碱(trans-neomatrine)。1的晶体结构(C_(15)H_(24) N_2O·C_(15)H_(24)N_2O·2HCl·5H_2O)属正交晶系，空间群P2_12_12_1, a = 0. 8053(2) nm, b = 1.3464(5) nm, c = 3.0971(9) nm, V = 3.3580(18)nm~3, Z = 4, μ=0.244 mm~(-1), F(000) = 1432, R = 0.0467, wR = 0.1129。顺式新苦参 碱和反式新苦参碱的A环、B环和C环为式构象，D环为半椅式构象，其中A／B为反式 稠合，A／C和B／C为顺式稠合，两种立异构体的区别是顺式新苦参碱的C／D顺式稠 合，反式新苦参碱的C／D反式稠合。     

The colonic metabolism differences of main alkaloids in normal and colitis mice treated with Coptis chinensis Franch. and Sophora flavescens Ait. herbal pair using liquid chromatography-high resolution mass spectrometry method combined with chemometrics

Coptis chinensis Franch. and Sophora flavescens Ait. is a herbal pair frequently used in treating ulcerative colitis. However, the bio-disposition profile of the major components in the inflamed gut remains unclear, which is essential to understand the pharmacological material basis of this herb pair. Here we established an integral quantitative and chemometric method to deduce the colonic metabolism differences of this herbal pair in normal and colitis mice. With this LC-MS method, a total of 41 components have been found in the Coptis chinensis Franch. and Sophora flavescens Ait. extract, and 28 metabolites were found in the colon after oral administration. Alkaloid and its phase I metabolites were the main components in the colon of normal and colitis mice. The results of principal component analysis at 6 h after oral administration showed significant colonic metabolism differences between normal and colitis mice. Heamap results showed that colitis induced significant changes in the colonic bio-disposition of this herbal pair extract. In particular, in the context of colitis, the phase I metabolism of berberine, coptisine, jatrorrhizine, palmatine,and epiberberine has been inhibited. These results may provide a basis for understanding the pharmacological material basis of Coptis chinensis Franch. and Sophora flavescens Ait. in treating ulcerative colitis.     

Phenolic Derivatives from the Root Bark of Oplopanax horridus

Four new phenolic derivatives, including two phenylpropanoid glycosides, one benzoate glycoside, and one lignan glycoside, together with one known glyceride, were isolated from the root bark of Oplopanax horridus. The structures of the new compounds were elucidated as 3‐{4‐[(6‐O‐acetyl‐β‐D ‐glucopyranosyl)oxy]‐3,5‐dimethoxyphenyl}propanoic acid ( 1 ), (+)‐[5,6,7,8‐tetrahydro‐7‐(hydroxymethyl)‐10,11‐dimehoxydibenzo[a,c][8]annulen‐6‐yl]methyl β‐D ‐glucopyranoside ( 2 ), (+)‐methyl 4‐[6‐O‐{3‐hydroxy‐3‐methyl‐5‐(1‐methylpropyl)oxy]‐5‐oxopentanoyl}‐4‐O‐(β‐D ‐glucopyranosyl)‐β‐D ‐glucopyranosyl)oxy]‐3‐methoxybenzoate ( 3 ), and 2‐methoxy‐4‐[(1E)‐3‐methoxy‐3‐oxoprop‐1‐en‐1‐yl]phenyl 6‐O‐{3‐hydroxy‐3‐methyl‐5‐[(1‐methylpropyl)oxy]‐5‐oxopentanoyl‐4‐O‐β‐d‐ glucopyranosyl‐β‐d‐ glucopyranoside ( 4 ) on the basis of spectroscopic techniques including NMR and MS analyses. The known compound was identified as glycer‐2‐yl ferulate ( 5 ) by comparing its physical and spectral data with those reported in the literature.     

Microwave-assisted extraction of oxymatrine from Sophora flavescens

In this paper, microwave-assisted extraction (MAE) of oxymatrine from Sophora flavescens were studied by HPLC-photodiode array detection. Effects of several experimental parameters, such as concentration of extraction solvent, ratio of liquid to material, microwave power, extraction temperature, and extraction time on the extraction efficiencies of oxymatrine were evaluated. The optimal extraction conditions were 60% ethanol, a 20:1 (v/v) ratio of liquid to material and extraction for 10 min at 50 °C under 500 W microwave irradiation. Under the optimum conditions, the yield of oxymatrine was 14.37 mg/g. The crude extract obtained could be used as either a component of some complex traditional medicines or for further isolation and purification of bioactive compounds. The results, which indicated that MAE is a very useful tool for the extraction of important phytochemicals from plant materials, should prove helpful for the full utilization of Sophora flavescens.     

Cytotoxic Isoprenylated Flavonoids from the Roots of Sophora flavescens

Three new flavonoids, which are isoprenylated by fused 2,2‐dimethyl‐3,4‐dihydro‐2H‐pyran moieties, were isolated from the roots of Sophora flavescens and named flavenochromanes A–C ( 1 – 3 ). Their structures were elucidated by spectroscopic methods, including 2D‐NMR techniques. Flavenochromane C ( 3 ) showed strong cytotoxic activity against A549 (lung carcinoma), 1A9 (ovarian carcinoma), KB (epidermoid carcinoma of the nasopharynx), and KB‐Vin (drug‐resistant variant KB) cell lines with IC₅₀ values ≤1.7 μM , and significant activity against the MCF‐7 (breast adenocarcinoma) cell line with an IC₅₀ value of 3.6 μM . Flavenochromane B ( 2 ) displayed slightly lower inhibitory effects (IC₅₀ 3.2–6.9 μM ) as compared with 3 .     

Three Cyclized Isoprenylated Flavonoids from the Roots and Rhizomes of Sophora tonkinensis

Two new flavanones, tonkinochromanes D ( 1 ) and E ( 2 ), and a new chalcone, tonkinochromane F ( 3 ), were isolated from the roots and rhizomes of Sophora tonkinensis. Their structures were elucidated by spectroscopic methods, including 2D‐NMR and circular‐dichroism (CD) techniques, in combination with HR‐MS analysis. Compounds 1 – 3 , as well the previously reported tonkinochromanes A–C, were shown by LC‐MS analysis to be ‘artifacts’ resulting from acid‐catalyzed electrophilic cyclization of isoprenyl side chains during extraction.     

A new di-C-prenylated coumarin from Sophora interrupta

A new di-C-prenylated coumarin, 7-methoxy-6,8-bis-(2,3-dihydroxy-3-methylbutyl)-coumarin (1), together with seven known compounds, isopimpinellin (2), an arylbenzofuran (3), three flavonoids (4–6), (+)-maackianin (7) and echinoisoflavanone (8), were isolated from the leaves of Sophora interrupta Bedd. The structure of the new compound 1 as well as known compounds was elucidated by extensive 1D and 2D NMR spectral studies.     

A new lavandulyl flavonoid from Sorphora flavescens Ait

A new lavandulyl flavonoid was isolated from the rhizome of Sorphora flavescens. The structure of new compound was elucidated on the basis of spectral methods including 2D NMR. And it showed potent cytotoxic activity against Hela cells with IC50 of 1.1 μmol/L.     

从苦参中提取总生物碱的微型化学实验研究

采用常量法和微量法对苦参中的总生物碱进行提取,比较这2种方法在提取率、试剂用量和提取时间方面的不同。结果表明,微量法的提取效果略高于常量法,其提取率为0.565%;微量法的苦参用量是常量法的10%,所用试剂乙醇、氯仿、氨水只占常量法的30%左右;完成本次实验微量法共需要6.5 h,而常量法则需29 h。     

New Phenolic Constituents from the Stems of Spatholobus suberectus

Three new phenolic compounds, 5‐O‐(β‐apiosyl‐(1 → 2)‐O‐β‐xylopyranosyl)gentisic acid ( 1 ), 1‐O‐(β‐apiosyl‐(1 → 6)‐O‐β‐glucopyranosyl)‐3‐O‐methylphloroglucinol ( 2 ), and 15‐O‐(α‐rhamnopyranosyl)aloe‐emodin ( 3 ), together with the known compound aloe emodin ( 4 ), were isolated from the stems of Spatholobus suberectus. Their structures were characterized by chemical and spectroscopic methods. The absolute configurations of the sugar units were not determined.     

超临界二氧化碳流体萃取中药苦参的生物总碱

超临界ＣＯ2流体萃取(ＣＯ2 ＳｕｐｅｒｃｒｉｔｉｃａｌＦｌｕｉｄＥｘｔｒａｃｔｉｏｎ,ＳＦＥ ＣＯ2)技术是一种新型分离提取技术,其选择分离效果好,提取率高,产物没有有机溶剂残留,有利于热敏性物质和易氧化物质的萃取[1]。苦参为豆科植物,是传统的清热燥湿类中药,其有效成分主要为生物碱。苦参生物碱具有抗肿瘤、平喘、升白、抗菌、抗病毒、抗原虫等多种功能[2]。由于生物碱在植物中多数以盐的形式存在,若直接用极性较弱的溶剂提取往往提取不完全,故在提取前需碱化,使之成为游离碱[3]。本实验用氨水作碱化剂,选用无水甲醇为夹带剂,…     

Simultaneous determination of matrine, sophoridine and oxymatrine in Sophora flavescens Ait. by high performance liquid chromatography

Following a detailed study, a reversed-phase high performance liquid chromatographic method (HPLC) has been developed and validated for analysis of three bioactive alkaloids, matrine, sophoridine and oxymatrine, in Sophora flavescens Ait. HPLC separation of the alkaloids was performed on a Kromasil C(18) column and detected by ultraviolet absorbance at 208 nm. The column temperature was maintained at 40 degrees C. A mobile phase composed of 0.01 mol/L KH(2)PO(4) buffer-methanol-triethylamine in the ratios 94:6:0.01 (v/v) was found to be the most suitable for this separation at a fl ow-rate of 1.0 mL/min and enabled the baseline separation of the three analytes free from interferences with isocratic elution. The analysis time was 24 min per injection. The calibration was linear in the range of 0.2-120.0 micro g/mL for matrine, 0.2-115.2 micro g/mL for sophoridine and 0.2-110.4 micro g/mL for oxymatrine, respectively. For assaying Sophora Flavescens Ait. samples, the relative standard deviations were 2.0% for matrine, 2.8% for sophoridine and 1.8% for oxymatrine analysis. The average recoveries of matrine, sophoridine and oxymatrine were 93.9, 95.3 and 93.5% for the Sophora flavescens Ait. samples, respectively. The method has been successfully applied to the simultaneous determination of matrine, sophoridine and oxymatrine in Sophora Flavescens Ait. samples collected in different habitats.     

Alkaloids from the Leaves and Stems of Daphniphyllum calycinum

One new alkaloid, named caldaphnidine H ( 1 ), together with eight known ones, daphnioldhanin G ( 2a ), methyl homosecodaphniphyllate ( 3 ), daphnezomine M ( 4 ), daphniyunine A ( 5 ), calyciphylline A ( 6 ), deoxycalyciphylline B ( 7 ), deoxyisocalyciphylline B ( 8 ), and calyciphylline B ( 9 ) was isolated from the leaves and stems of Daphniphyllum calycinum. The structure of 1 was established by spectral methods, especially 2D‐NMR techniques. The structure of daphnioldhanin G ( 2b ) reported previously was revised to 2a mainly by single‐crystal X‐ray diffraction and spectral analysis.     

A New Alkaloid from the Seeds of Sophora alopecuroides L.

Alopecurin A, an alkaloid with an unprecedented skeleton, was isolated from the seeds of Sophora alopecuroides L. The absolute configuration and structure of this compound was identified as (3S,12R)‐3‐hydroxy‐1,7‐diazatricyclo[10.4.0.1^3,7]heptadecane‐11,16,17‐trione (=(7S,15aR)‐decahydro‐7‐hydroxy‐6H‐7,11‐methano‐4H‐pyrido[1,2‐a][1,7]diazacyclododecine‐4,15,16(12H)‐trione). The structure and absolute configuration was elucidated by spectroscopic methods, mainly HR‐ESI‐TOF‐MS, IR, 1D‐NMR (¹H‐ and ¹³C‐NMR), 2D‐NMR (COSY, NOESY, HSQC, HMBC), and particularly X‐ray crystal‐diffraction and CD spectral analysis.