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Kirenol

Cat No.:V14864 Purity: ≥98%
Kirenol (Kirel)is a natural product extracted fromSiegesbeckia orientalis with a variety of biological effects such as anti-inflammatory, antitumor, anti-oxidant, anti-allergic, and anti-arthritic activities.
Kirenol
Kirenol Chemical Structure CAS No.: 52659-56-0
Product category: Immunology & Inflammation related
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Kirenol (Kirel) is a natural product extracted from Siegesbeckia orientalis with a variety of biological effects such as anti-inflammatory, antitumor, anti-oxidant, anti-allergic, and anti-arthritic activities. It is effective against gram-positive bacteria and exhibits anticancer activity against human chronic myeloid leukemia K562 cells in vitro. Kirenol is capable of promoting osteoblast differentiation in MC3T3-E1 cells through activation of the BMP and Wnt/β-catenin signaling pathways. Kirenol can reduce pro-inflammatory cytokine secretion, increase anti-inflammatory cytokine production, inhibitcell proliferation and induce apoptosis of CII-specific lymphocytes in vitro.
Kirenol (CAS 52659-56-0) is a biologically active diterpenoid isolated from the herb of Siegesbeckia orientalis. It possesses a wide range of activities, including anti-oxidant, anti-inflammatory, anti-allergic, anti-adipogenic, and anti-arthritic activities. It reduces pro-inflammatory cytokine secretion, increases anti-inflammatory cytokine production, inhibits cell proliferation, and induces apoptosis of CII-specific lymphocytes. Kirenol may be a potential immunosuppressant for the treatment of rheumatoid arthritis. It also possesses antibacterial activity against gram-positive bacteria.
Biological Activity I Assay Protocols (From Reference)
Targets
Kirenol targets inflammatory pathways and immune cells. It reduces the secretion of pro-inflammatory cytokines such as TNF-α, IL-1β, and IL-6, while increasing the production of anti-inflammatory cytokines such as IL-10. It can upregulate nuclear Annexin-1, which is involved in the anti-inflammatory response. It inhibits the proliferation of CII-specific lymphocytes and induces their apoptosis, suggesting a direct effect on autoimmune T cells. Its anti-inflammatory and immunosuppressive effects make it a candidate for treating autoimmune diseases like rheumatoid arthritis. Its antioxidant activity also contributes to its protective effects.
ln Vitro
In vitro, Kirenol possesses anti-inflammatory, anti-oxidant, and anti-arthritic activities. It reduces pro-inflammatory cytokine secretion and increases anti-inflammatory cytokine production. It inhibits cell proliferation and induces apoptosis of CII-specific lymphocytes. It is effective against gram-positive bacteria. Kirenol induces autophagy, mitophagy, and osteoblast differentiation, and promotes mitochondrial fusion. It exerts antioxidant, anti-inflammatory, antifibrotic, renoprotective, cardioprotective, neuroprotective, and analgesic effects. It is a valuable tool for studying inflammation and immunity.
ln Vivo
In vivo, Kirenol has been shown to reduce motor deficit and delay disease onset by approximately five days in an animal model of arthritis. It possesses anti-inflammatory and analgesic activity. It may be a potential immunosuppressant for the treatment of rheumatoid arthritis. Its efficacy in animal models supports its potential for development as a therapeutic agent for inflammatory and autoimmune diseases. Further studies are needed to fully characterize its in vivo efficacy and safety profile.
Enzyme Assay
The in vitro assay for Kirenol involves measuring its anti-inflammatory effects on immune cells, such as macrophages or lymphocytes. Cells are treated with varying concentrations of Kirenol (0.1-100 µM) and stimulated with LPS or other inflammatory stimuli. Cytokine levels (TNF-α, IL-1β, IL-6, IL-10) in the culture supernatant are measured by ELISA. Cell proliferation is assessed using MTT or BrdU incorporation assays. Apoptosis is evaluated using Annexin V staining or caspase-3/7 activity assays. The compound's antibacterial activity is assessed using disc diffusion or MIC assays against gram-positive bacteria.
Cell Assay
In vitro cellular assays for Kirenol use immune cells such as macrophages (RAW 264.7), lymphocytes, or chondrocytes. Cells are cultured in appropriate media and treated with the compound at concentrations of 0.1-100 µM for 1-24 hours. Cytokine production is measured by ELISA or Luminex. Cell viability is assessed using MTT or CCK-8 assays. Apoptosis is evaluated using Annexin V staining and caspase-3/7 activity assays. The compound's effects on cell signaling pathways (e.g., NF-κB, MAPK) can be assessed by Western blot. These assays help characterize its mechanism of action as an anti-inflammatory agent.
Animal Protocol
In vivo animal studies for Kirenol involve models of rheumatoid arthritis, such as collagen-induced arthritis (CIA) in mice or rats. Animals are treated with the compound via oral gavage or intraperitoneal injection at doses of 1-50 mg/kg. Arthritis severity is assessed by clinical score, paw swelling, and histological analysis of joints. Cytokine levels in serum and joint tissues are measured by ELISA. The compound's effects on immune cell populations in spleen and lymph nodes are characterized by flow cytometry. These studies evaluate its efficacy as an anti-arthritic agent.
ADME/Pharmacokinetics
Kirenol has a molecular weight of 338.48 and a molecular formula of C20H34O4. It is a diterpenoid compound isolated from natural sources. It is soluble in DMSO and should be stored at -20°C for long-term preservation. Its pharmacokinetic properties, including oral bioavailability, half-life, and tissue distribution, are not extensively reported in the available literature. For in vivo studies, it can be formulated in suitable vehicles such as 10% DMSO + 90% corn oil or other standard formulations.
References

[1]. Topical anti-inflammatory and analgesic activity of kirenol isolated from Siegesbeckia orientalis, Journal of Ethnopharmacology, Volume 137, Issue 3, 2011, Pages 1089-1094, ISSN 0378-8741.

[2].Kirenol\nAttenuates Experimental Autoimmune Encephalomyelitis by Inhibiting\nDifferentiation of Th1 and Th17 Cells and Inducing Apoptosis of Effector\nT Cells[J]. Scientific Reports, 2015, 5(1):9022.

Additional Infomation
Kirenol is a diterpenoid compound. It has been reported to exist in Sigesbeckia glabrescens, Sigesbeckia orientalis, and Sigesbeckia pubescens, and relevant data are available.
Kirenol is a diterpenoid with the CAS number 52659-56-0. It has anti-inflammatory, anti-oxidant, anti-allergic, and anti-arthritic activities. It reduces pro-inflammatory cytokines and increases anti-inflammatory cytokines. It is effective against gram-positive bacteria and may be a potential immunosuppressant for rheumatoid arthritis. The compound is a research tool and is not for human therapeutic use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H34O4
Molecular Weight
338.49
Exact Mass
338.245
CAS #
52659-56-0
PubChem CID
15736732
Appearance
Off-white to light yellow solid powder
Density
1.2±0.1 g/cm3
Boiling Point
516.9±35.0 °C at 760 mmHg
Melting Point
197.0 to 201.0 °C
Flash Point
233.6±20.5 °C
Vapour Pressure
0.0±3.1 mmHg at 25°C
Index of Refraction
1.570
LogP
1.78
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
3
Heavy Atom Count
24
Complexity
518
Defined Atom Stereocenter Count
7
SMILES
C[C@@]1(CC[C@@H]2C(=C1)CC[C@H]3[C@]2(C[C@@H](C[C@@]3(C)CO)O)C)[C@H](CO)O
InChi Key
NRYNTARIOIRWAB-JPDRSCFKSA-N
InChi Code
InChI=1S/C20H34O4/c1-18(17(24)11-21)7-6-15-13(8-18)4-5-16-19(2,12-22)9-14(23)10-20(15,16)3/h8,14-17,21-24H,4-7,9-12H2,1-3H3/t14-,15-,16-,17+,18+,19+,20+/m1/s1
Chemical Name
(1R)-1-[(2S,4aR,4bS,6S,8R,8aS)-6-hydroxy-8-(hydroxymethyl)-2,4b,8-trimethyl-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-2-yl]ethane-1,2-diol
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~295.44 mM)
H2O : < 0.1 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 3.25 mg/mL (9.60 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 32.5 mg/mL clear DMSO stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 3.25 mg/mL (9.60 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 32.5 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 3.25 mg/mL (9.60 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 32.5 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.9543 mL 14.7715 mL 29.5430 mL
5 mM 0.5909 mL 2.9543 mL 5.9086 mL
10 mM 0.2954 mL 1.4771 mL 2.9543 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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