Isomucronulatol
(Synonyms: 7,2'-二羟基-3',4'-二甲氧基异黄烷) 目录号 : GC39099Isomucronulatol 是从 A. membranaceus 根中分离得到的一种黄酮类化合物。Isomucronulatol 在体外对 LPS 刺激产生的 IL-12 p40 有抑制作用,具有潜在的抗炎活性。
Cas No.:52250-35-8
Sample solution is provided at 25 µL, 10mM.
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Isomucronulatol is a flavonoid isolated from the roots of A. membranaceus. Isomucronulatol exhibits inhibitory effects on LPS-stimulated production IL-12 p40 in vitro and has potential anti-inflammatory effect[1].
[1]. Li W, et al. Flavonoids from Astragalus membranaceus and their inhibitory effects on LPS-stimulated pro-inflammatory cytokine production in bone marrow-derived dendritic cells. Arch Pharm Res. 2014 Feb;37(2):186-92.
Cas No. | 52250-35-8 | SDF | |
别名 | 7,2'-二羟基-3',4'-二甲氧基异黄烷 | ||
Canonical SMILES | OC1=CC=C2CC(C3=CC=C(OC)C(OC)=C3O)COC2=C1 | ||
分子式 | C17H18O5 | 分子量 | 302.32 |
溶解度 | Soluble in DMSO | 储存条件 | Store at -20°C |
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1 mM | 3.3078 mL | 16.5388 mL | 33.0775 mL |
5 mM | 0.6616 mL | 3.3078 mL | 6.6155 mL |
10 mM | 0.3308 mL | 1.6539 mL | 3.3078 mL |
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Inhibition of Osteoarthritis-Related Molecules by Isomucronulatol 7- O-β-d-glucoside and Ecliptasaponin A in IL-1β-Stimulated Chondrosarcoma Cell Model
Molecules 2018 Oct 29;23(11):2807.PMID:30380653DOI:10.3390/molecules23112807.
Osteoarthritis (OA) is the common form of arthritis and is characterized by disability and cartilage degradation. Although natural product extracts have been reported to have anti-osteoarthritic effects, the potential bioactivity of Ryupunghwan (RPH), a traditional Korean medicinal botanical formula that contains Astragalus membranaceus, Turnera diffusa, Achyranthes bidentata, Angelica gigas, Eclipta prostrata, Eucommia ulmoides, and Ilex paraguariensis, is not known well. Therefore, the inhibitory effects of single compounds isolated from RPH on the OA-related molecules were investigated using IL-1β-stimulated chondrosarcoma SW1353 (SW1353) cell model. Two bioactive compounds, Isomucronulatol 7-O-β-d-glucoside (IMG) and ecliptasaponin A (ES) were isolated and purified from RPH using column chromatography, and then the structures were analyzed using ESI-MS, ¹H-NMR, and 13C-NMR spectrum. The expression or amount of matrix metalloproteinase 13 (MMP13), COX1/2, TNF-α, IL-1β or p65 was determined by RT-PCR, Western blot, and enzyme-linked immunosorbent assay (ELISA). RPH pretreatment reduced the expression and amounts of MMP13, and the expression of collagen II, COX1/2, TNF-α, IL-1β or p65, which were increased in IL-1β-stimulated SW1353 cells. IMG reduced the expression of all OA-related molecules, but the observed inhibitory effect was less than that of RPH extract. The other single compound ES showed the reduced expression of all OA-related molecules, and the effect was stronger than that in IMG (approximately 100 fold). Combination pretreatment of both single components remarkably reduced the expression of MMP13, compared to each single component. These synergic effects may provide potential molecular modes of action for the anti-osteoarthritic effects of RPH observed in clinical and animal studies.
Machaerium opacum Vogel (Fabaceae): phytochemical study and toxicity to Atta sexdens Linnaeus (Hymenoptera: Formicidae)
Nat Prod Res 2022 Nov;36(22):5762-5765.PMID:34903130DOI:10.1080/14786419.2021.2013213.
In this work was described the phytochemical investigation of Machaerium opacum Vogel (Fabaceae) leaves as well as the insecticidal activity of its crude extract and fractions against Atta sexdens Linnaeus (Hymenoptera: Formicidae). The phytochemical study led to the identification of α-amyrin, β-amyrin, lupeol, phytol, Isomucronulatol and rutin, described for the first time in M. opacum and mucronulatol. Insecticidal activity was assessed by the ingestion of the crude extract and fractions incorporated into an artificial diet at three different concentrations (0.2, 1.0 and 2.0 mg mL-1). Statistical analysis revealed that all the samples of M. opacum at all concentrations tested showed significant results when compared to the pure diet control.
Rapid Quantitative Analysis of 19 Bioactive Components in Fangji Huangqi Decoction Based on UHPLC-MS/MS
J Chromatogr Sci 2022 Oct 15;bmac085.PMID:36250324DOI:10.1093/chromsci/bmac085.
Fangji Huangqi Decoction (FHD) is a classic prescription of traditional Chinese medicine which is recorded in "Jin Gui Yao Lue". The purpose of this study is to develop a method for simultaneous determination multicomponent in FHD. The separation of the 19 compounds that included calycosin, calycosin-7-O-β-D-glucoside, formononetin, ononin, methylnissolin, methylnissolin-3-O-glucoside, Isomucronulatol, tetrandrine, fangchinoline, atractylenolide-I, atractylenolide-III, liquiritigenin, liquiritin, isomucronulatol-7-O-β-D-glucoside, astragaloside-I, astragaloside-II, astragaloside-III, astragaloside-IV and glycyrrhetinic acid were achieved by linear gradient elution. The 19 components were identified by comparing the chromatographic peaks with the reference compounds and were quantitatively analyzed by multiple reaction monitoring. This method was strict validated with recovery (96.10-101.70%), precision [relative standard deviation (RSD), 1.34-3.34%], stability (RSD, 1.49-3.80%) and repeatability (RSD, 1.60-3.49%), respectively. All the compounds showed good linearities (R2 > 0.999). The limit of detection (LOD) and limit of quantitation (LOQ) for the 19 compounds were in the range of 0.03-0.27 μg/mL (LODs) and 0.05-1.23 μg/mL (LOQs). The correlation analysis indicated that astragalus flavonoids were negatively correlated with astragalosides, tetrandrine and their corresponding flavonoid glycosides, and atractylenolides were positively correlated with astragalosides and fangchinoline. This method proved to be reliable and effective, which would give a helpful basis for the quality control, pharmacological and pharmacokinetic of FHD.
Flavonoids from Astragalus membranaceus and their inhibitory effects on LPS-stimulated pro-inflammatory cytokine production in bone marrow-derived dendritic cells
Arch Pharm Res 2014 Feb;37(2):186-92.PMID:23771500DOI:10.1007/s12272-013-0174-7.
Radix Astragali (Astragalus membranaceus) is an important traditional Chinese medicine that is widely used as a tonic to enhance the body's natural defense mechanisms. In this phytochemical study, 12 flavonoids, isoliquiritigenin (1), liquiritigenin (2), calycosin (3), calycosin 7-O-β-D-glucoside (4), formononetin (5), formononetin 7-O-β-D-glucoside (6), daidzein (7), daidzein 7-O-β-D-glucoside (8), methylnissolin (9), methylnissolin 3-O-β-D-glucoside (10), Isomucronulatol (11), and Isomucronulatol 7-O-β-D-glucoside (12), were isolated from the roots of A. membranaceus. Their structures were elucidated by comparing spectroscopic data with reported values. The effects of the isolated compounds on lipopolysaccharide (LPS)-stimulated bone marrow-derived dendritic cells were investigated. Compounds 1 and 2 exhibited significant inhibitory effects on LPS-induced IL-6 and IL-12 p40 production, with IC50 values ranging from 2.7 to 6.1 μM. Compound 1 also showed a moderate inhibitory effect on LPS-stimulated production of TNF-α with an IC50 value of 20.1 μM. Further studies of the potential anti-inflammatory effects and benefits of flavonoids from A. membranaceus are warranted.
A new indolizinone from Polygonatum kingianum
Planta Med 2003 Nov;69(11):1066-8.PMID:14735451DOI:10.1055/s-2003-45160.
A new indolizinone, namely kinganone (1) together with 3-ethoxymethyl-5,6,7,8-tetrahydro-8-indolizinone (2) and Isomucronulatol (3) were isolated from the rhizome of Polygonatum kingianum. Their structures were elucidated mainly on the basis of spectral data. Indolizinones 1 and 2 showed weak antibacterial and antifungal activities when compared to rifampicin and amphotericin, respectively, in the agar diffusion assay.