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    Natural Products
    Isocupressic acid
    Isocupressic acid
    Information
    CAS No. 1909-91-7 Price
    Catalog No.CFN99882Purity>=98%
    Molecular Weight320.5 Type of CompoundDiterpenoids
    FormulaC20H32O3Physical DescriptionPowder
    Download Manual    COA    MSDSSimilar structuralComparison (Web)
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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 / Inquiry
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  • Biological Activity
    Description: Isocupressic acid induces abortion in pregnant cows when ingested primarily during the last trimester, it decrease affects the angiogenesis of the female reproductive system, the decrease in blood flow and apoptosis of corpus luteum-derived endothelial cells of the uterine tissue results in abortion. Isocupressic acid shows strong inhibitory effect on Epstein-Barr virus early antigen (EBV-EA) induction (100 % inhibition at 1000 mol ratio/12-O-tetradecanoylphorbol 13-acetate (TPA).
    Targets: P450 (e.g. CYP17) | cAMP | PKA
    In vitro:
    Anim Reprod Sci. 2004 Apr;81(3-4):237-44.
    Efects of the pine needle abortifacient, isocupressic acid, on bovine oocyte maturation and preimplantation embryo development.[Pubmed: 14998650]
    Isocupressic acid (ICA) [15-hydroxylabda-8 (17), 13E-dien-19-oic acid], a labdane diterpene acid, isolated from ponderosa pine (Pinus ponderosa), Lodgepole pine (Pinus contorta), common juniper (Juniperus communis) and Monterey cypress (Cupressus macrocarpa), induces abortion in pregnant cows when ingested primarily during the last trimester. The objective of this study was to investigate the effects of Isocupressic acid on bovine oocyte maturation (in vitro maturation (IVM)-Experiment I) and preimplantation embryo development (in vitro culture (IVC)-Experiment II) using in vitro embryo production techniques and to subsequently evaluate viability and developmental competence of Isocupressic acid-cultured embryos via embryo transfer to recipient heifers (Experiment III).
    METHODS AND RESULTS:
    A complete randomized block experimental design was used. In Experiment I and II, Isocupressic acid was added to IVM or IVC media at 0 (TRT1, control), 1.3 (TRT2), and 2.6 microg/ml (TRT3) Results from Experiment I and II indicated that Isocupressic acid did not inhibit oocyte maturation and did not adversely affect preinpiantation embryo development. Furthermore, results from Experiment II demonstrated that Isocupressic acid enhanced bovine preimplantation embryo development in vitro in a dose dependent manner. Subsequently, Day 8 (Day 0 = IVF) blastocysts cultured in vitro in the medium containing 2.6 microg/ml Isocupressic acid were transferred to recipient heifers and resulted in normal pregnancies as determined by ultrasound imaging. Subsequently, all but two births were normal as evaluated by post natal veterinary examination.
    CONCLUSIONS:
    In conclusion, Isocupressic acid showed no adverse effects on oocyte maturation and preimplantation embryo development in vitro or subsequent viability in vivo using the Isocupressic acid concentrations and in vitro culture parameters of this study.
    Am J Chin Med. 2002;30(4):533-41.
    Isocupressic acid blocks progesterone production from bovine luteal cells.[Pubmed: 12568280]
    The needles of ponderosa pine (Pinus ponderosa Laws.) were reported to induce abortions when fed to late-term pregnant beef cows in North America. An in vivo study of pregnant cows suggested that Isocupressic acid (IA) was the main abortifacient isolated from needles and bark of the pine. However, the mechanism of abortifacient activity of Isocupressic acid is not clear yet. In a pregnant cow, the corpus luteum of the ovary helps the maintenance of pregnancy by its progesterone production. This study involved the Isocupressic acid extracted from the root of the Taiwan cypress (Juniperus formosana) and used a frozen-thawed bovine luteal cell culture system to investigate the action of Isocupressic acid on progesterone production.
    METHODS AND RESULTS:
    Thawed bovine luteal cells (1 x 10(5) cells/ml/well) in M199 medium were cultured in 24-well culture plates at 37 degrees C in a 5% CO2 incubator. Ten ml of tested drugs, Isocupressic acid at 1 to 1000 ng/ml and/or ovine luteinizing hormone (oLH) at 1 to 100 ng/microl or 8-bromo-cyclic adenosine monophosphate (8-Br-cAMP) with 0.1-10 mM, were added into each well. After 4 hours of incubation, the media were harvested and assayed for progesterone by an enzyme immunoassay. Progesterone production from cells was the indicator used to evaluate the action of Isocupressic acid. All tested doses of Isocupressic acid significantly inhibited progesterone production in both basal and oLH stimulating conditions. Also those dosages inhibited cyclic adenosine-3',5'- monophosphate (cAMP) stimulation, suggesting a post-cAMP mechanism is involved in the Isocupressic acid action.
    CONCLUSIONS:
    We concluded that Isocupressic acid can induce pregnant cows to abort partly through blocking luteal function and may be identified as a new abortifacient chemical.
    Planta Med. 2003 Jan;69(1):69-72.
    Potential antitumor promoting diterpenoids from the stem bark of Thuja standishii.[Pubmed: 12567284 ]
    Six diterpenes, including one new natural product, were isolated from a CHCl 3 extract of the stem bark of THUJA STANDISHII.
    METHODS AND RESULTS:
    The new compound has been characterized as 15-oxolabda-8(17),13 Z-dien-19-oic acid. The known compounds were identified as ferruginol ( 2), sugiol ( 3), Isocupressic acid ( 4), sandaracopimaric acid ( 5) and 15-oxolabda-8(17),13 E-dien-19-oic acid ( 6). Compounds 2 - 5 and the derivatives 4A and 4B were tested for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by 12- O-tetradecanoylphorbol 13-acetate (TPA).
    CONCLUSIONS:
    Compounds 2, 3, 4 and 5 showed strong inhibitory effect on EBV-EA induction (100 % inhibition at 1000 mol ratio/TPA).
    Isocupressic acid Description
    Source: The barks of Araucaria cunninghami
    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 3.1201 mL 15.6006 mL 31.2012 mL 62.4025 mL 78.0031 mL
    5 mM 0.624 mL 3.1201 mL 6.2402 mL 12.4805 mL 15.6006 mL
    10 mM 0.312 mL 1.5601 mL 3.1201 mL 6.2402 mL 7.8003 mL
    50 mM 0.0624 mL 0.312 mL 0.624 mL 1.248 mL 1.5601 mL
    100 mM 0.0312 mL 0.156 mL 0.312 mL 0.624 mL 0.78 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:
    Evid Based Complement Alternat Med. 2012;2012:190107.
    Molecular Mechanism of Isocupressic Acid Supresses MA-10 Cell Steroidogenesis.[Pubmed: 22666287]
    Consumption of ponderosa pine needles causes late-term abortions in cattle and is a serious poisonous plant problem in foothill and mountain rangelands. Isocupressic acid (IA) is the component of pine needles responsible for the abortifacient effect, its abortifacient effect may be due to inhibition of steroidogenesis.
    METHODS AND RESULTS:
    To investigate the more detail molecular mechanism, we used MA-10 cell, which is wild used to investigate molecular mechanism of steroidogenesis, to characterize the molecular mechanisms underlying the actions of IA in more detail. In this report, we focus on the function of IA on important steroidogenic genes, including steroidogenic acute regulatory protein (StAR), cytochrome P450 cholesterol side-chain cleavage (P450scc), and 3β-hydroxysteroid dehydrogenase (3β-HSD). We found that IA does not affect enzyme activities of these genes but inhibits transcription of P450scc and translation of StAR and P450scc through attenuating cAMP-PKA signaling.
    CONCLUSIONS:
    Thus, steroid productions of cells were suppressed.