Sophorabioside
(Synonyms: 槐属双苷) 目录号 : GC61283Sophorabioside是一种从Sophorajaponica分离的黄酮苷。
Cas No.:2945-88-2
Sample solution is provided at 25 µL, 10mM.
Quality Control & SDS
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- Purity: >98.00%
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Sophorabioside is a flavonoid-glycoside isolated from Sophora japonica[1].
[1]. Kim JM, et al. Anti-platelet effects of flavonoids and flavonoid-glycosides from Sophora japonica. Arch Pharm Res. 2008;31(7):886-890.
Cas No. | 2945-88-2 | SDF | |
别名 | 槐属双苷 | ||
Canonical SMILES | O=C1C(C2=CC=C(O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O[C@H]4[C@@H]([C@@H]([C@H]([C@H](C)O4)O)O)O)C=C2)=COC5=CC(O)=CC(O)=C15 | ||
分子式 | C27H30O14 | 分子量 | 578.52 |
溶解度 | DMSO : 50 mg/mL (86.43 mM; Need ultrasonic) | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg | |
1 mM | 1.7285 mL | 8.6427 mL | 17.2855 mL |
5 mM | 0.3457 mL | 1.7285 mL | 3.4571 mL |
10 mM | 0.1729 mL | 0.8643 mL | 1.7285 mL |
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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 | |||
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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。
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Determination of Sophorabioside in Rat Plasma by UPLC-MS/MS and its Application to a Pharmacokinetic Study
J Chromatogr Sci 2018 Feb 1;56(2):154-159.PMID:29190333DOI:10.1093/chromsci/bmx097.
A ultra-performance liquid chromatography tandem mass spectrometry method was initially developed and validated for quantification of Sophorabioside in rat plasma using kaempferol-3-O-β-D-rutinoside as the internal standard (IS). Analyte and IS were preparation through a protein precipitation procedure with 1.0 mL of methanol to a 0.1 mL plasma sample. The processed samples were separated by C18 analytical column using methanol/water containing 0.1% formic acid with gradient elution as the mobile phase at a flow rate of 0.3 mL/min. Sophorabioside (m/z 577.15 → 269.45) and kaempferol-3-O-β-D-rutinoside (m/z 593.15 → 285.84) were detected by a triple quadrupole tandem mass spectrometer in negative electrospray ionization mode using multiple reaction monitoring. The calibration curve for Sophorabioside was linear in the range of 6-1,200 ng/mL (r2 > 0.995) with a lower limit of quantification of 6 ng/mL. The inter- and intra-day precision and accuracy were well within the acceptable limits. The matrix effects were satisfactory in all of the biological matrices examined. The mean recovery of Sophorabioside was always >90%. This method was successfully applied to a pharmacokinetic study of Sophorabioside in rats after an oral administration of 90 mg/kg Sophorabioside. The main pharmacokinetic parameters: Tmax, Cmax and t1/2 were 6.2 ± 0.8 h, 1430.83 ± 183.25 ng/mL, 7.2 ± 0.5 h, respectively.
Isolation of antiosteoporotic compounds from seeds of Sophora japonica
PLoS One 2014 Jun 3;9(6):e98559.PMID:24892557DOI:10.1371/journal.pone.0098559.
Chemical investigation of Sophora japonica seeds resulted in the isolation of seven metabolites identified as: genistin (1), sophoricoside (2), Sophorabioside (3), sophoraflavonoloside (4), genistein 7,4'-di-O-β-D-glucopyransoide (5), kaempferol 3-O-α-L-rhamnopyranosyl(1 → 6)β-D-glucopyranosyl(1 → 2)β-D-glucopyranoside (6) and rutin (7). Compounds 1, 2 and 5 showed significant estrogenic proliferative effect in MCF-7 cell in sub-cytotoxic concentration range. Compounds 1 and 2 showed minimal cell membrane damaging effect using LDH leakage assay. Accordingly, compound 2 (sophoricoside, (SPH)) was selected for further in-vivo studies as a potential anti-osteoporosis agent. The anti-osteoporotic effect of SPH was assessed in ovarectomized (OVX) rats after oral administration (15 mg/kg and 30 mg/kg) for 45 days compared to estradiol (10 µg/kg) as a positive control. Only in a dose of 30 mg/kg, SPH regained the original mechanical bone hardness compared to normal non-osteoporotic group. However, SPH (15 mg/kg) significantly increased the level of alkaline phosphatase (ALP) to normal level. Treatment with SPH (30 mg/kg) increased the level of ALP to be higher than normal group. SPH (15 mg/kg) did not significantly increase the serum level of osteocalcin (OC) compared to OVX group. On the other hand, treatment with SPH (30 mg/kg) significantly increased the level of OC to 78% higher than normal non-ovarectomized animals group. In addition, SPH (15 mg/kg) decreased the bone resorption marker, acid phosphatase (ACP) to normal level and SPH (30 mg/kg) further diminished the level of serum ACP. Histopathologically, sophoricoside ameliorated the ovarectomy induced osteoporosis in a dose dependent manner. The drug showed thicker bony trabeculae, more osteoid, and more osteoblastic rimming compared to OVX group.
UPLC-MS identification and anticomplement activity of the metabolites of Sophora tonkinensis flavonoids treated with human intestinal bacteria
J Pharm Biomed Anal 2020 May 30;184:113176.PMID:32092632DOI:10.1016/j.jpba.2020.113176.
Anticomplement activity played an important role in anti-inflammatory effects of traditional Chinese herbs. The total flavonoids of Sophora tonkinensis (TFST) were inactive on the complement system but showed obvious anticomplement activity after incubated with human intestinal bacteria in vitro. In order to discover the metabolic activation of TFST by intestinal flora, the constituents of TFST and its metabolites were identified by UPLC-ESI-LTQ/MS. Their anticomplement activities were evaluated through the classical and alternative pathway. As a result, eighteen flavonoids were identified, including seven flavonoid glycosides, five aglycones and six isoprenylated flavonoids. All the glycosides (daidzein-4'-glucoside-rhamnoside, Sophorabioside, rutin, isoquercitrin, quercitrin, ononin, trifolirhizin) were metabolized into their corresponding aglycones in different extent by human intestinal bacteria, resulting in the contents of the five aglycones were highly increased in 24 h. However, no changes have occurred on the six isoprenylated flavonoids. Interestingly, three aglycones (quercetin, formononetin and maackiain) had significantly more potent anticomplement activities than their prototype glycosides. The results indicated that the enhancement of TFST anticomplement activity was attributed to the active aglycones, especially formononetin and quercetin, produced by human intestinal bacteria. These aglycones are likely to be among the potential active components of S. tonkinensis for its inhibiting inflammation effects.
Four new isoflavone triglycosides from Sophora japonica
J Nat Prod 2001 Aug;64(8):1107-10.PMID:11520241DOI:10.1021/np010081s.
Four new isoflavone triglycosides, genistein 7-O-beta-D-glucopyranoside-4'-O-[(alpha-L-rhamnopyranosyl)-(1-->2)-beta-D-glucopyranoside] (1), genistein 7-O-beta-D-glucopyranoside-4'-O-[(beta-D-glucopyranosyl)-(1-->2)-beta-D-glucopyranoside] (2), genistein 7-O-alpha-L-rhamnopyranoside-4'-O-[(alpha-L-rhamnopyranosyl)-(1-->2)-beta-D-glucopyranoside] (3), and genistein 7-O-alpha-L-rhamnopyranoside-4'-O-[(beta-D-glucopyranosyl)-(1-->2)-beta-D-glucopyranoside] (4), together with nine known compounds, namely, genistein 7-O-beta-D-glucopyranoside-4'-O-beta-D-glucopyranoside, Sophorabioside, prunetin 4'-O-beta-D-glucopyranoside, sophororicoside, genistin, rutin, kaempferol 3-O-beta-rutinoside, quercetin 3-O-beta-D-glucopyranoside, and kaempferol 3-O-beta-D-glucopyranoside, were isolated from the pericarps of Sophora japonica. The structures of 1-4 were determined by spectroscopic methods.
Anti-platelet effects of flavonoids and flavonoid-glycosides from Sophora japonica
Arch Pharm Res 2008 Jul;31(7):886-90.PMID:18704331DOI:10.1007/s12272-001-1242-1.
A methanol extract of Sophora japonica was subjected to anti-platelet activity guided fractionation affording the isolation of four flavonoids and six flavonoid-glycosides: biochanin A (1), irisolidone (2), genistein (3), sissotrin (4), Sophorabioside (5), genistin (6), tectoridin (7), apigenin (8), quercitrin (9), and rutin (10). The structure of each compound was determined by a variety of spectroscopic methods. Among the compounds, 1, 3, and 7 showed approximately 2.5-6.5 fold greater inhibitory effects on arachidonic acid (AA) and U46619 induced platelet aggregation (IC50: 19.9 and 99.8 microM; 20.3 and 53.8 microM; 25.9 and 123.4 microM, respectively) than acetylsalicylic acid (ASA, IC50: 63.0 and 350.0 microM). Compound 2 was an approximately 22-40 fold stronger inhibitor than ASA on AA and U46619 induced aggregation (IC50: 1.6 and 15.6 microM, respectively).