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    CAS No. 66777-70-6 Price
    Catalog No.CFN97705Purity>=98%
    Molecular Weight422.48Type of CompoundFlavonoids
    FormulaC25H26O6Physical DescriptionYellow powder
    Download Manual    COA    MSDSSimilar structuralComparison (Web)
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  • Biological Activity
    Description: 6,8-Diprenylorobol possesses weaker anti-H. pylori activity, it may be a useful chemopreventive agent for peptic ulcer or gastric cancer in H. pylori-infected individuals; it is evaluated against the AIDS-related opportunistic fungal pathogens, Candida albicans and Cryptococcus neoformans. 6,8-Diprenylorobol shows anti-estrogenic activity comparable to that of 4-hydroxytamoxifen, a typical estrogen receptor (ER) antagonist. 6,8-Diprenylorobol shows promising cytotoxic effects toward HL-60 cells (IC50 4.3 ± 0.7 to 18.0 ± 1.7 uM), it also may be a possible candidate for the treatment of neurodegenerative diseases. 6,8-Diprenylorobol has antioxidant activity, it can reduce A2E photooxidation in a dose dependent manner.
    Targets: Estrogen receptor | Antifection | HIV | Progestogen receptor
    In vitro:
    Life Sci. 2002 Aug 9;71(12):1449-63.
    Anti-Helicobacter pylori flavonoids from licorice extract.[Pubmed: 12127165]
    Licorice is the most used crude drug in Kampo medicines (traditional Chinese medicines modified in Japan). The extract of the medicinal plant is also used as the basis of anti-ulcer medicines for treatment of peptic ulcer.
    Among the chemical constituents of the plant, glabridin and glabrene (components of Glycyrrhiza glabra), licochalcone A (G. inflata), licoricidin and licoisoflavone B (G. uralensis) exhibited inhibitory activity against the growth of Helicobacter pylori in vitro. These flavonoids also showed anti-H. pylori activity against a clarithromycin (CLAR) and amoxicillin (AMOX)-resistant strain. We also investigated the methanol extract of G. uralensis. From the extract, three new isoflavonoids (3-arylcoumarin, pterocarpan, and isoflavan) with a pyran ring, gancaonols A[bond]C, were isolated together with 15 known flavonoids. Among these compounds, vestitol, licoricone, 1-methoxyphaseollidin and gancaonol C exhibited anti-H. pylori activity against the CLAR and AMOX-resistant strain as well as four CLAR (AMOX)-sensitive strains. Glycyrin, formononetin, isolicoflavonol, glyasperin D, 6,8-Diprenylorobol, gancaonin I, dihydrolicoisoflavone A, and gancaonol B possessed weaker anti-H. pylori activity.
    These compounds may be useful chemopreventive agents for peptic ulcer or gastric cancer in H. pylori-infected individuals.
    J. Funct. Foods, 2017, 29:104-14.
    Orobol derivatives and extracts from Cudrania tricuspidata fruits protect against 6-hydroxydomamine-induced neuronal cell death by enhancing proteasome activity and the ubiquitin/proteasome-dependent degradation of α-synuclein and synphilin-1[Reference: WebLink]
    We investigated the neuroprotective effects of orobol derivatives and ethanol extracts from Cudrania tricuspidata fruits.
    Among the nine isolates from a 50% ethanol extract from Cudrania tricuspidata fruits (CTE50), orobol (OB), 6-prenylorobol (POB), and 6,8-Diprenylorobol (DPOB) showed neuroprotective effects in 6-OHDA-induced SH-SY5Y cell death. In addition, CTE50 and the three orobol derivatives (OB, POB, and DPOB) attenuated the cleavage of caspase-3, caspase-9, and PARP and inhibited the excessive generation of ROS. Furthermore, it enhanced the 6-OHDA-induced dysfunction of proteasome activity and reduced the accumulation of ubiquitin conjugated-proteins and the polyubiquitination of α-synuclein and synphilin-1. The proteasome inhibitor MG132 blocked the neuroprotective effects and the enhanced proteasome activity produced by CTE50 and the three orobol derivatives.
    These results demonstrate that CTE50 and three orobol derivatives protect against 6-OHDA-induced neurotoxicity by enhancing the ubiquitin/proteasome-dependent degradation of α-synuclein and synphilin-1, suggesting that they might be possible candidates for the treatment of neurodegenerative diseases.
    J Asian Nat Prod Res. 2017 May;19(5):510-518.
    Prenylated isoflavones from Cudrania tricuspidata inhibit NO production in RAW 264.7 macrophages and suppress HL-60 cells proliferation.[Pubmed: 27649772]

    Inhibitory effects of NO production in RAW 264.7 macrophages guided the isolation of nine prenylated isoflavones, including a new cudraisoflavone L (1) and eight known metabolites furowanin B (2), erysubin A (3), wighteone (4), lupalbigenin (5), laburnetin (6), isolupalbigenin (7), 6,8-Diprenylorobol (8), millewanin H (9) from the leaves of Cudrania tricuspidata.
    At the concentration of 10 μM, compounds 1, 2, and 4 significantly inhibited NO production with the inhibitory values of 72.5 ± 2.4, 66.9 ± 1.8, and 55.4 ± 2.7%, respectively. In addition, all of isolated compounds 1-9 showed promising cytotoxic effects toward HL-60 cells (IC50 4.3 ± 0.7 to 18.0 ± 1.7 μM).
    Nat. Prod. Sci., 2011(17):206-11.
    Isolation of Prenylated Isoflavonoids from Cudrania tricuspidata Fruits that Inhibit A2E Photooxidation.[Reference: WebLink]

    High-performance liquid chromatography coupled to an online -based assay (online HPLC-) system was used to determine the principal antioxidants in Cudrania tricuspidata fruits. Six prenylated isoflavonoids (1 - 6) were isolated from C. tricuspidata fruits according to the online HPLC- system. The structures of isolated compounds, alpiniumisoflavone (1), 6,8-Diprenylorobol (2), 6,8-diprenylgenistein (3), pomiferin (4), 4'-methylalpiniumisoflavone (5), and osajin (6) were identified by their retention time, UV spectra, ESI-MS, and NMR data.
    Among these compounds, 6,8-Diprenylorobol (2) and pomiferin (4) reduced A2E photooxidation in a dose dependent manner.
    6,8-Diprenylorobol Description
    Source: The roots of Glycyrrhiza uralensis Fisch
    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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    Recently, ChemFaces products have been cited in many studies from excellent and top scientific journals

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    Calculate Dilution Ratios(Only for Reference)
    1 mg 5 mg 10 mg 20 mg 25 mg
    1 mM 2.367 mL 11.8349 mL 23.6698 mL 47.3395 mL 59.1744 mL
    5 mM 0.4734 mL 2.367 mL 4.734 mL 9.4679 mL 11.8349 mL
    10 mM 0.2367 mL 1.1835 mL 2.367 mL 4.734 mL 5.9174 mL
    50 mM 0.0473 mL 0.2367 mL 0.4734 mL 0.9468 mL 1.1835 mL
    100 mM 0.0237 mL 0.1183 mL 0.2367 mL 0.4734 mL 0.5917 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.
    Structure Identification:
    Planta Med. 2001 Feb;67(1):87-9.
    Antifungal chalcones from Maclura tinctoria.[Pubmed: 11270732]
    Five prenylated flavonoids, including one new natural product, were isolated from an ethanol extract of the leaves of Maclura tinctoria (L.) Gaud.
    The new compound has been characterized as 2',4',4,2''-tetrahydroxy-3'-[3''-methylbut-3''-enyl]chalcone (1). The known compounds were identified as 2',4',4-trihydroxy-3'-[3''-methylbut-3''-enyl]chalcone (isobavachalcone) (2), 4,2'-dihydroxy-2''-[1-hydroxy-1-methylethyl]-2'',3''-dihydrofurano[4'',5'':3',4']chalcone (bakuchalcone) (3), 4,4',5''-trihydroxy-6'',6''-dimethyldihydropyrano[2'',3'':5',6'']chalcone (bavachromanol) (4), and 5,7,3',4'-tetrahydroxy-6,8-diprenylisoflavone (6,8-Diprenylorobol) (5). All the isolated compounds were evaluated against the AIDS-related opportunistic fungal pathogens, Candida albicans and Cryptococcus neoformans.
    Compound 2 was active against both yeasts.
    J. Health Sci., 2006, 52(2):186-91.
    Anti-Estrogenic Activity of Prenylated Isoflavones from Millettia pachycarpa: Implications for Pharmacophores and Unique Mechanisms[Reference: WebLink]
    Phytoestrogens containing isoflavonoids are thought to exhibit preventative effects on estrogen-responsive diseases. Chemical modifications, such as prenylation, in biosynthetic processes enhance the structural variety of isoflavonoids and prompted us to carry out a structure-activity relationship study.
    We determined the estrogenic/anti-estrogenic activities and estrogen receptor (ER)-binding affinities of eight kinds of prenylated isoflavones isolated from Millettia pachycarpa (Leguminosae), and those of two kinds of non-prenylated compounds (genistein and daidzein). By comparing these compounds, the pharmacophores for estrogenic/anti-estrogenic activities were elucidated. None of the tested compounds (except genistein) were estrogenic on ligand-dependent yeast-two hybrid assay. On the other hand, 5 isoflavones showed distinct anti-estrogenic activity. Unexpectedly, the most potent antagonists, isoerysenegalensein E and 6,8-Diprenylorobol, showed anti-estrogenic activity comparable to that of 4-hydroxytamoxifen, a typical ER antagonist.
    This suggests that genistein became an antagonist after prenylation and hydroxylation. The pharmacophores providing genistein with strong anti-estrogenic activity were as follows: prenyl groups of the 6- and 8-positions on the A-ring, hydroxyl group of the 6-prenyl moiety or the B-ring (catechol form), non-cyclization of the prenyl group with the A-ring, and non-hydroxylation of the 8-prenyl group on the A-ring. The ER-binding affinities of the isoflavonoids were not sufficiently high to explain their potent antagonistic activities, thus suggesting 17β-estradiol-non-competitive mechanisms.