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Asperglaucide Sale

(Synonyms: 金色酰胺醇酯,Asperglaucide) 目录号 : GC46885

An amide with diverse biological activities

Asperglaucide Chemical Structure

Cas No.:56121-42-7

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500 μg
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1 mg
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产品描述

Asperglaucide is an amide originally isolated from P. aurantiacum that has diverse biological activities, including anti-inflammatory, antibacterial, antioxidant, and anticancer properties.1,2,3,4 Asperglaucide inhibits production of nitric oxide (NO), prostaglandin E2 , and IL-1β in LPS-stimulated BV-2 microglial cells (IC50s = 49.7, 51.5, and 40.4 µM, respectively).2 It is active against Gram-negative bacteria (MICs = 0.05-0.10 mg/ml) and has antioxidant activity in 2,2-diphenyl-1-picrylhydrazyl and Trolox equivalent antioxidant capacity (TEAC) assays (EC50s = 9.51-78.81 µg/ml).3 Asperglaucide decreases viability of U87 and U251 cancer cells in vitro when used at concentrations ranging from 10 to 100 µM and reduces tumor growth when administered at a dose of 1 mg via intratumoral injection in a U87 mouse xenograft model.4

1.Banerji, A., and Ray, R.Aurantiamides: A new class of modified dipeptides from Piper aurantiacumPhytochemistry20(9)2217-2220(1981) 2.Yoon, C.S., Kim, D.C., Lee, D.S., et al.Anti-neuroinflammatory effect of aurantiamide acetate from the marine fungus Aspergillus sp. SF-5921: Inhibition of NF-κB and MAPK pathways in lipopolysaccharide-induced mouse BV2 microglial cellsInt. Immunopharmacol.23(2)568-574(2014) 3.Tamokou, J.D., Simo Mpetga, D.J., Keilah Lunga, P., et al.Antioxidant and antimicrobial activities of ethyl acetate extract, fractions and compounds from stem bark of Albizia adianthifolia (Mimosoideae)BMC Complement. Altern. Med.1299(2012) 4.Yang, Y., Zhang, L.H., Yang, B.X., et al.Aurantiamide acetate suppresses the growth of malignant gliomas in vitro and in vivo by inhibiting autophagic fluxJ. Cell. Mol. Med.19(5)1055-1064(2015)

Chemical Properties

Cas No. 56121-42-7 SDF
别名 金色酰胺醇酯,Asperglaucide
Canonical SMILES O=C(N[C@@H](CC1=CC=CC=C1)C(N[C@@H](CC2=CC=CC=C2)COC(C)=O)=O)C3=CC=CC=C3
分子式 C27H28N2O4 分子量 444.5
溶解度 DMSO: soluble,Ethanol: soluble 储存条件 Store at -20°C
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1 mM 2.2497 mL 11.2486 mL 22.4972 mL
5 mM 0.4499 mL 2.2497 mL 4.4994 mL
10 mM 0.225 mL 1.1249 mL 2.2497 mL
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Research Update

Effect of different storage conditions on the stability and safety of almonds

J Food Sci 2023 Feb;88(2):848-859.PMID:36633227DOI:10.1111/1750-3841.16453.

Almond production in Portugal is of great importance for the economy of their main producing areas. However, the contamination of these nut fruits with fungi and mycotoxins poses a significant risk to food safety and security. This work intended to evaluate the influence of storage conditions on the microbial and mycotoxin stability and safety of almonds throughout long-term storage. Two almond varieties-Lauranne and Guara-were submitted to three different storage conditions, namely, 4°C with noncontrolled relative humidity (RH), 60% RH at 25°C, and 70% RH at 25°C, for a storage period of 9 months. Samples were collected after 0, 3, 6, and 9 months of storage and analyzed for microbial loads (aerobic mesophiles, yeasts, and molds), mold incidence and diversity, and mycotoxin contamination. In total, 26 species were identified belonging to 6 genera: Aspergillus, Cladosporium, Fusarium, Penicillium, Paecilomyces, and Talaromyces. For the variety Guara, mycotoxins related to Aspergillus sect. Flavi, such as aflatoxins, averufin, versicolorin C, and norsolorinic acid, were detected only after 9 months of storage at 70% and 60% RH. Penicillium mycotoxins, such as quinolactacin A and roquefortine C, were also detected. For the variety Lauranne, Penicillium mycotoxins were detected, such as citrinin, quinolactacins A and B, roquefortines C and D, cyclopenin, cyclopenol, penitrem A, viridicatin, and viridicatol. Mycotoxins related to Aspergillus, such as aspulvinone E, flavoglaucin, paspalin, Asperglaucide, asperphenamate, cyclo(L-Pro-L-Tyr), and cyclo(L-Pro-L-Val), were also detected. PRACTICAL APPLICATION: (Optional, for JFS Research Articles ONLY) The quality of almonds depends on the storage period and the RH and temperature at which they are stored. Storage of almonds at 60% RH at 25°C is a good storage condition to maintain the stability and safety of nuts in terms of microbial and mycotoxin contaminations.

Lignans and other constituents from the roots of the Vietnamese medicinal plant Pseuderanthemum palatiferum

Planta Med 2011 Jun;77(9):951-4.PMID:21243588DOI:10.1055/s-0030-1250683.

Two new lignans, palatiferin A (1) and palatiferin B (2), were isolated from the roots of Pseuderanthemum palatiferum, together with five known triterpenes, epifriedelanol (3), lupeol (4), lupenone (5), betulin (6), pomolic acid (7), and a dipeptide Asperglaucide (8). Their structures were established from 2D NMR and mass spectroscopy. The absolute configuration of 1 and 2 was proposed based on the comparison of their optical rotation activities with those of compounds with similar structures such as wodeshiol and paulownin. The new lignans, palatiferin A (1) and palatiferin B (2) exhibited a moderate cytotoxicity against KB and HepG2 cell lines. However, betulin and lupeol, two abundant compounds from the roots of P. palatiferum, showed cytotoxic and antimicrobial activities.

Integrated Network Pharmacology Analysis and In Vitro Validation Revealed the Potential Active Components and Underlying Mechanistic Pathways of Herba Patriniae in Colorectal Cancer

Molecules 2021 Oct 5;26(19):6032.PMID:34641576DOI:10.3390/molecules26196032.

Herba Patriniae (HP) are medicinal plants commonly used in colorectal cancer (CRC) patients. In this study, network pharmacology was used to predict the active components and key signaling pathways of HP in CRC. Patrinia heterophylla, one type of HP, was chosen for validation of the network pharmacology analysis. The phytochemical profile of Patrinia heterophylla water extract (PHW) was determined by UHPLC-MS. MTT, RT-PCR, and Western blot assays were performed to evaluate the bioactivities of PHW in colon cancer cells. Results showed that 15 potentially active components of HP interacted with 28 putative targets of CRC in the compound-target network, of which Asperglaucide had the highest degree. Furthermore, the ErbB signaling pathway was identified as the pathway mediated by HP with the most potential against CRC. Both RT-PCR and Western blot results showed that PHW significantly downregulated the mRNA and protein levels of EGFR, PI3K, and AKT in HCT116 cells. Asperglaucide, present in PHW, exhibited an anti-migratory effect in HCT116 cells, suggesting that it could be an active component of PHW in CRC treatment. In conclusion, this study has provided the first scientific evidence to support the use of PHW in CRC and paved the way for further research into the underlying mechanisms of PHW against CRC.

Effect of storage temperature and duration on concentrations of 27 fungal secondary metabolites spiked into floor dust from an office building

J Occup Environ Hyg 2020 May;17(5):220-230.PMID:32275482DOI:10.1080/15459624.2020.1734205.

Fungi are ubiquitous in environments and produce secondary metabolites that are usually low-molecular-weight organic compounds during growth processes. Dust samples containing these fungal secondary metabolites collected from study sites are often stored in certain temperature conditions for an extended period until laboratory analysis resources are available. However, there is little information on how stable fungal secondary metabolites are over time at different storage temperatures. We examined the stability of 27 fungal secondary metabolites spiked into floor dust samples collected from a moisture-damaged office building. Ninety-five dust aliquots were made from the spiked dust; five replicates were randomly assigned to a baseline (time = 0) and each of the 18 combinations of three temperatures (room temperature, 4 °C, or -80 °C) and six time points (2, 12, 25, 56, 79, and 105 weeks). At the baseline and each subsequent time point, we extracted and analyzed the fungal secondary metabolites from the spiked dust using ultra-performance liquid chromatograph-tandem mass spectrometer. To estimate change in concentration over storage time at each temperature condition, we applied multiple linear regression models with interaction effect between storage temperature and duration. For 10 of the 27 fungal secondary metabolites, the effect of time was significantly (p-values <0.05) or marginally (p-values <0.1) modified by temperature, but not for the remaining 17 metabolites. Generally, for most fungal secondary metabolites, storage at room temperature was significantly (p-values <0.05) associated with a larger decline in concentration (up to 83% for 3-nitropropionic acid at about 11 months) than storing at 4 °C (up to 55% for emodin) or -80 °C (55% for Asperglaucide). We did not observe significant differences between storage at 4 °C, or -80 °C. Storage temperature influenced degradation of fungal secondary metabolites more than storage time. Our study indicates that fungal secondary metabolites, including mycotoxins in floor dust, quickly degrade at room temperature. However, storing dust samples at 4 °C might be adequate given that storing them at -80 °C did not further reduce degradation of fungal secondary metabolites.

Anti-inflammatory and antiproliferative compounds from Sphaeranthus africanus

Phytomedicine 2019 Sep;62:152951.PMID:31136898DOI:10.1016/j.phymed.2019.152951.

Background: Sphaeranthus africanus has been used in traditional Vietnamese medicine to treat sore throat, and to relieve pain and swelling. However, the anti-inflammatory activity of this plant had not yet been investigated. Previously, we isolated five carvotacetones (1-5) from this plant that displayed cytotoxicity against several cancer cell lines. Purpose: The objective of this study was to isolate further constituents from S. africanus and to investigate the anti-inflammatory activity of all constituents. Furthermore, the anti-proliferative activity of the newly isolated compounds was evaluated. Study design and methods: Compounds were isolated from the upper parts of S. africanus by chromatographic methods. Structures were determined using spectroscopic techniques, like NMR and MS. All nine compounds isolated from S. africanus were evaluated for inhibitory activity against COX-1 and COX-2 isoenzymes in-vitro, COX-2 mRNA expression and influence on NO production. The anti-proliferative activities of newly isolated compounds (6-9) were evaluated by XTT viability assay with four cancer cell lines, namely CCRF-CEM, MDA-MB-231, HCT-116, and U-251 cells. Results: Two diastereomeric carvotacetones (3-angeloyloxy-5-[2″S,3″R-dihydroxy-2″-methyl-butanoyloxy]-7-hydroxycarvotacetone (6) and 3-angeloyloxy-5-[2″R,3″R-dihydroxy-2″-methyl-butanoyloxy]-7-hydroxycarvotacetone (7), Asperglaucide (8) and chrysoplenol D (9) were isolated from S. africanus. COX-1 and COX-2 assays of compounds 1-9 revealed that compounds 1 and 2 possess potent and selective COX-2 inhibitory activity with IC50 values of 3.6 and 0.5 μM, respectively. COX-2 gene expression assay showed that some carvotacetones exhibited inhibitory effects on COX-2 gene expression in THP-1 macrophages. Compound 4 is the most active compound inhibiting the synthesis of COX-2 by 55% at 2.06 μM. In the iNOS assay, all seven carvotacetones inhibited NO production in BV2 and RAW cell lines with IC50 values ranging from 0.2 to 2.9 μM. Compound 4 showed potent inhibitory activity with IC50 values of 0.2 μM in both BV2 and RAW cell lines. Molecular docking studies revealed the binding orientations of 1 and 2 in the active sites of COX-2. XTT assay of the newly isolated compounds revealed that the two isomeric carvotacetones (6-7) exhibited considerable anti-proliferative activity against four cancer cell lines (CCRF-CEM, MDA-MB-231, HCT-116, U-251) with IC50 values ranging from 1.23 to 8 μM. Conclusion: For the first-time, the diastereomeric carvotacetones (6-7) were isolated as separate compounds, and their anti-proliferative activity was determined. Selective COX-2 inhibitory, COX-2 mRNA expression and NO production inhibitory activities by some of the major constituents of S. africanus supports the traditional medical application of this plant for the treatment of inflammation-related disorders.