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    Natural Products
    (+)-Epipinoresinol
    Information
    CAS No. 24404-50-0 Price $338 / 5mg
    Catalog No.CFN92288Purity>=98%
    Molecular Weight358.4Type of CompoundLignans
    FormulaC20H22O6Physical DescriptionPowder
    Download Manual    COA    MSDS    SDFSimilar structuralComparison (Web)  (SDF)
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    According to end customer requirements, ChemFaces provide solvent format. This solvent format of product intended use: Signaling Inhibitors, Biological activities or Pharmacological activities.
    Size /Price /Stock 10 mM * 1 mL in DMSO / $287.3 / In-stock
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    (+)-Epipinoresinol

    (+)-Epipinoresinol
    Product Name (+)-Epipinoresinol
    CAS No.: 24404-50-0
    Catalog No.: CFN92288
    Molecular Formula: C20H22O6
    Molecular Weight: 358.4 g/mol
    Purity: >=98%
    Type of Compound: Lignans
    Physical Desc.: Powder
    Source: The heartwoods of Picea excelsa
    Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
    Price: $338 / 5mg
    Inquire / Order: manager@chemfaces.com
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  • Related Screening Libraries
    Size /Price /Stock 10 mM * 100 uL in DMSO / Inquiry / In-stock
    10 mM * 1 mL in DMSO / Inquiry / In-stock
    Related Libraries
  • Lignans Compound Library
  • Biological Activity
    Description: Reference standards.
    In vitro:
    Zhongguo Zhong yao za zhi,2013, 38(14):2321-2324.
    Chemical constituents from stems of Brucea mollis and their cytotoxic activity.[Reference: WebLink]

    METHODS AND RESULTS:
    Ten compounds were isolated from the stems of Brucea mollis by various chromatographic techniques such as column chromatography on silica gel and Sephadex LH-20, and preparative HPLC, and their structures were elucidated as deacetylated isobrucein B (1), indaquassin X (2), cleomiscosin A (3), cleomiscosin B (4), (+)-lyoniresinol (5), (+)-Epipinoresinol(6), (+)-pinoresinol (7), (+)-syringaresinol (8), 4,5-dihydroblumenol A (9) and adenosine (10) on the basis of spectroscopic data analysiS. All compounds were obtained from this plant for the first time, moreover, compound 1 was a new natural product.
    CONCLUSIONS:
    Compound 2 showed significant cytotoxic activities against the human cell lines HT-29, HepG2, BGC-823 and SKOV3 with IC50 values of 0.84-3.97 micromol x L(-1).
    Plant Cell Physiol . 2018 Nov 1;59(11):2278-2287.
    Formation of a Methylenedioxy Bridge in (+)-Epipinoresinol by CYP81Q3 Corroborates with Diastereomeric Specialization in Sesame Lignans[Pubmed: 30085233]
    Abstract Plant specialized metabolites are often found as lineage-specific diastereomeric isomers. For example, Sesamum alatum accumulates the specialized metabolite (+)-2-episesalatin, a furofuran-type lignan with a characteristic diastereomeric configuration rarely found in other Sesamum spp. However, little is known regarding how diastereomeric specificity in lignan biosynthesis is implemented in planta. Here, we show that S. alatum CYP81Q3, a P450 orthologous to S. indicum CYP81Q1, specifically catalyzes methylenedioxy bridge (MDB) formation in (+)-Epipinoresinol to produce (+)-pluviatilol. Both (+)-Epipinoresinol and (+)-pluviatilol are putative intermediates of (+)-2-episesalatin based on their diastereomeric configurations. On the other hand, CYP81Q3 accepts neither (+)- nor (-)-pinoresinol as a substrate. This diastereomeric selectivity of CYP81Q3 is in clear contrast to that of CYP81Q1, which specifically converts (+)-pinoresinol to (+)-sesamin via (+)-piperitol by the sequential formation of two MDBs but does not accept (+)-Epipinoresinol as a substrate. Moreover, (+)-pinoresinol does not interfere with the conversion of (+)-Epipinoresinol to (+)-pluviatilol by CYP81Q3. Amino acid substitution and CO difference spectral analyses show that polymorphic residues between CYP81Q1 and CYP81Q3 proximal to their putative substrate pockets are crucial for the functional diversity and stability of these two enzymes. Our data provide clues to understanding how the lineage-specific functional differentiation of respective biosynthetic enzymes substantiates the stereoisomeric diversity of lignan structures.
    (+)-Epipinoresinol Description
    Source: The heartwoods of Picea excelsa
    Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
    Storage: Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

    Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

    Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com

    After receiving: The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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    Calculate Dilution Ratios(Only for Reference)
    1 mg 5 mg 10 mg 20 mg 25 mg
    1 mM 2.7902 mL 13.9509 mL 27.9018 mL 55.8036 mL 69.7545 mL
    5 mM 0.558 mL 2.7902 mL 5.5804 mL 11.1607 mL 13.9509 mL
    10 mM 0.279 mL 1.3951 mL 2.7902 mL 5.5804 mL 6.9754 mL
    50 mM 0.0558 mL 0.279 mL 0.558 mL 1.1161 mL 1.3951 mL
    100 mM 0.0279 mL 0.1395 mL 0.279 mL 0.558 mL 0.6975 mL
    * Note: If you are in the process of experiment, it's need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
    Protocol
    Kinase Assay:
    Frontiers in Pharmacology, 2018, 9:401.
    Lignans From Forsythia x Intermedia Leaves and Flowers Attenuate the Pro-inflammatory Function of Leukocytes and Their Interaction With Endothelial Cells.[Reference: WebLink]
    Taking into account that overactivated leukocytes are an important factor in the development of many chronic diseases, we investigated the activity of phytochemically characterized (HPLC-DAD-MSⁿ) extracts from forsythia leaves and flowers on the pro- and anti-inflammatory functions of leukocytes (effects on IL-1β, IL-8, TNF-α, and TGFβ release) and their adherence to endothelial cells. Using bio-guided fractionation, we isolated the active compounds and determined their biological activity, and we included the positive control quercetin.
    METHODS AND RESULTS:
    The effect on IL-1β, TNF-α, IL-8, and TGF-α production by leukocytes was measured by enzyme-linked immunosorbent assay (ELISA). The surface expression of adhesion molecules was analyzed with flow cytometry, and the neutrophil attachment to the endothelial cells was assessed fluorimetrically. The effects on p38MAPK, ERK1/2 and JNK phosphorylation were determined using western blots. Leaf extracts had the effect of decreasing TNF-α production in neutrophils and monocyte/macrophage cells. The bio-guided fractionation led to the isolation of the following lignan aglycones: (+)-pinoresinol, (+)-Epipinoresinol, (−)-matairesinol, (+)-phillygenin, and (−)-arctigenin. Only phillygenin was able to stimulate the anti-inflammatory function of macrophages by inducing TGF-β release and IL-10 receptor surface expression. Arctigenin, phillygenin, and a metabolite produced by the gut microbiota, enterolactone, decreased TNF-α and IL-1β production and neutrophil adhesion to endothelial cells, probably by attenuating the p38 and ERK kinase pathways.
    CONCLUSIONS:
    Forsythia x intermedia is a valuable source of active lignans, which may be potential candidates for treating inflammatory diseases that are associated with the excessive production of cytokines such as TNF-α and IL-1β.
    Animal Research:
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1995, 43(12):2200-2204.
    Pharmacologically active components of Todopon Puok (Fagraea racemosa), a medicinal plant from Borneo.[Reference: WebLink]

    METHODS AND RESULTS:
    The lignans of (+)-pinoresinol, (+)-Epipinoresinol, (+)-lariciresinol and (+)-isolariciresinol together with phenols such as syringaldehyde and 7,8-dihydro-7-oxy-coniferyl alcohol were isolated from Todopon Puok (Fagraea racemosa JACK ex WALL.), a medicinal plant from Borneo, using a bioassay of the relaxation effect on norepinephrine (NE)-induced contraction in rat aortic strips. The plant extract also exhibited analgesic properties in the acetic acid-induced writhing and tail pressure tests in mice, with the activity being concentrated in the lignan fraction.
    CONCLUSIONS:
    (+)-Pinoresinol showed analgesic effect on writhing symptoms in mice which were dose-dependent, and produced local anesthesia in guinea pigs.
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