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| Targets |
1. PI3K/AKT signaling pathway, apoptotic proteins (Bax, Bcl-2, cleaved caspase-3/9), cell cycle regulatory proteins (Cyclin D1, p21) [1]
2. Nrf2/HO-1 antioxidant pathway, inflammatory factors (TNF-α, IL-6, IL-1β), apoptotic proteins (Bax, Bcl-2) [2] |
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| ln Vitro |
1. Anticancer activity in non-small cell lung carcinoma (NSCLC) cells (A549, H1299):
- α-Bisabolol (20–80 μM) inhibited cell proliferation in a concentration-dependent manner, with IC50 values of 45 μM (A549) and 52 μM (H1299) after 72 hours (MTT assay) [1] - At 60 μM, it induced apoptosis: Annexin V-positive cells increased from 8% (control) to 42% (A549), accompanied by upregulated Bax (2.3-fold) and cleaved caspase-3/9 (3.1-fold), and downregulated Bcl-2 (0.4-fold) (Western blot) [1] - It caused G0/G1 cell cycle arrest: G0/G1 phase cells increased from 45% (control) to 68% (A549) at 60 μM, with reduced Cyclin D1 (0.3-fold) and elevated p21 (2.8-fold) [1] - It inhibited cell migration (scratch assay: 60 μM reduced wound closure from 85% to 32% at 24 hours) and invasion (Transwell assay: 60 μM decreased invasive cells by 65%) [1] - It downregulated phosphorylated AKT (p-AKT, 0.5-fold) to suppress the PI3K/AKT signaling pathway [1] 2. Nephroprotective activity in human renal proximal tubular cells (HK-2): - α-Bisabolol (10–40 μM) protected HK-2 cells from cisplatin (20 μM)-induced damage: cell viability increased from 40% (cisplatin alone) to 78% (40 μM α-Bisabolol) [2] - It reduced cisplatin-induced oxidative stress: 40 μM decreased intracellular ROS by 55% and MDA by 48%, while increasing SOD activity by 2.1-fold and GSH by 1.8-fold [2] - It inhibited inflammation: 40 μM downregulated TNF-α (0.4-fold) and IL-6 (0.3-fold) (ELISA), and suppressed apoptosis: cleaved caspase-3 decreased by 60% (Western blot) [2] - It activated the Nrf2/HO-1 pathway: 40 μM increased nuclear Nrf2 (2.5-fold) and HO-1 (3.2-fold) [2] |
| ln Vivo |
In cisplatin-induced acute kidney injury (AKI) in C57BL/6 mice:
- Mice were divided into 4 groups: control, cisplatin (20 mg/kg, intraperitoneal injection, single dose), cisplatin + α-Bisabolol (20 mg/kg), cisplatin + α-Bisabolol (40 mg/kg) [2] - α-Bisabolol was administered intraperitoneally once daily for 7 days (starting 1 day before cisplatin). At 40 mg/kg, it reduced serum creatinine (from 180 μmol/L to 95 μmol/L) and blood urea nitrogen (BUN, from 35 mmol/L to 18 mmol/L) [2] - Renal histopathology showed reduced tubular necrosis (from 85% to 30%) and inflammatory cell infiltration at 40 mg/kg [2] - It decreased renal MDA (45%) and increased SOD (2.2-fold) and GSH (1.9-fold) to alleviate oxidative stress [2] - It downregulated renal TNF-α (0.4-fold) and IL-1β (0.3-fold), and upregulated Nrf2 (2.8-fold) and HO-1 (3.5-fold) in renal tissue [2] |
| Enzyme Assay |
1. Antioxidant enzyme activity assay (SOD, CAT):
- Renal tissue homogenates (from mice) or HK-2 cell lysates were prepared. Incubate samples with SOD/CAT assay buffer and substrate (e.g., xanthine for SOD) at 37°C for 30 minutes [2] - For SOD: Measure absorbance at 560 nm to quantify inhibition of superoxide anion; for CAT: Measure absorbance at 240 nm to monitor H2O2 decomposition. Calculate enzyme activity using standard curves [2] 2. Inflammatory factor ELISA assay (TNF-α, IL-6): - Collect mouse serum or HK-2 cell culture supernatant. Add 100 μL samples to antibody-coated ELISA plates, incubate at 37°C for 1 hour [2] - Wash plates, add biotinylated secondary antibody, incubate for 30 minutes, then add streptavidin-HRP. Incubate for 15 minutes, add TMB substrate, stop reaction with H2SO4, and measure absorbance at 450 nm. Quantify using TNF-α/IL-6 standards [2] |
| Cell Assay |
1. NSCLC cell proliferation assay (MTT):
- Seed A549/H1299 cells (1×10⁴/well) in 96-well plates, treat with α-Bisabolol (0–80 μM) for 72 hours. Add MTT (5 mg/mL), incubate 4 hours, dissolve formazan with DMSO, measure absorbance at 570 nm. Calculate IC50 via nonlinear regression [1] 2. Apoptosis assay (Annexin V-FITC/PI): - Treat A549 cells (5×10⁵/well) with α-Bisabolol (60 μM) for 24 hours. Harvest cells, stain with Annexin V-FITC and PI, analyze by flow cytometry. Count Annexin V-positive/PI-negative (early apoptosis) and Annexin V-positive/PI-positive (late apoptosis) cells [1] 3. HK-2 cell ROS detection: - Seed HK-2 cells (2×10⁴/well) in 96-well plates, treat with cisplatin (20 μM) ± α-Bisabolol (40 μM) for 24 hours. Add DCFH-DA (10 μM), incubate 30 minutes at 37°C. Measure fluorescence intensity at 488 nm (excitation) and 525 nm (emission) to quantify ROS levels [2] 4. Western blot assay: - Lyse cells/tissues, extract protein, separate by SDS-PAGE, transfer to PVDF membranes. Block with 5% BSA, incubate with primary antibodies (e.g., Bax, Bcl-2, p-AKT, Nrf2) at 4°C overnight [1,2] - Add HRP-conjugated secondary antibody, incubate 1 hour, detect signals via chemiluminescence. Quantify band intensity using ImageJ, normalize to β-actin [1,2] |
| Animal Protocol |
Cisplatin-induced AKI mouse model:
- Male C57BL/6 mice (8–10 weeks old) were acclimated for 1 week. The AKI model was induced by a single intraperitoneal injection of cisplatin (20 mg/kg) [2] - α-Bisabolol was dissolved in 0.9% saline + 5% DMSO. Mice in treatment groups received 20 or 40 mg/kg α-Bisabolol via intraperitoneal injection once daily for 7 days (day -1 to day 5, with cisplatin administered on day 0) [2] - On day 6, mice were sacrificed. Collect blood via cardiac puncture to measure serum creatinine and BUN; harvest kidneys, fix in 4% paraformaldehyde for histopathology, or freeze in liquid nitrogen for Western blot and oxidative stress assays [2] |
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
This study aimed to investigate the skin absorption of sesquiterpenoids (the main active ingredient in chamomile). To this end, we prepared 14C-labeled levo-chamomileol ((-)-6-methyl-2-(4-methyl-3-cyclohexen-1-yl)-5-hepten-2-ol; (-)-α-bisabolol) by incorporating [14C]-acetate into the molecule using biochemical methods. Five hours after topical application of the radiolabeled substance to nude mouse skin, half of the radioactive material was present in the skin. The other half was present in tissues and organs. Analysis revealed that 90% of the radioactive material was intact levo-chamomileol. To demonstrate the distribution of this substance in the skin, we used a cryostat to cut some skin tissue into horizontal sections. These sections were then subjected to autoradiography analysis. Density measurements showed that levomethoxazole rapidly penetrated the skin. Five hours after topical application, the substance had migrated from the outer layer of the skin to the inner layer. Therefore, it can be seen that levomethasone has rapid skin absorption and long-lasting anti-inflammatory and antispasmodic effects. |
| Toxicity/Toxicokinetics |
1. In vitro experiments: α-bisabolol (concentration up to 80 μM) showed extremely low toxicity to normal human bronchial epithelial cells (BEAS-2B) and normal renal proximal tubular cells (HK-2), with cell survival rate >80% [1,2]
2. In vivo experiments: α-bisabolol (40 mg/kg, intraperitoneal injection, for 7 consecutive days) did not cause weight loss (>5% of initial body weight) or abnormal liver function (normal ALT and AST levels) in mice. No pathological damage was observed in the kidney tissue of non-AKI mice treated with α-bisabolol alone [2] |
| References |
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| Additional Infomation |
(-)-α-Bisabolol is a sesquiterpene compound. Bisabolol, or more formally known as α-(−)-bisabolol, also called levobariol, is found in fats and oils. (-)-α-bisabolol is isolated from the essential oil of chamomile (German chamomile). (-)-α-bisabolol belongs to the sesquiterpene class of compounds. Sesquiterpenes are terpenoids composed of three consecutive isoprene units. Levobilool has been reported in Japanese spruce (Picea jezoensis), kidney fir (Abies nephrolepis), and other organisms with relevant data. See also: Chamomile (partial); Adenosine; Levomentol (ingredient)... See more...
Drug Indications Levomentol is known to cause a variety of potentially beneficial pharmacological effects, including anti-irritant, anti-inflammatory, and antibacterial effects. Bisabolol has also been shown to enhance the transdermal absorption of certain molecules. Pharmacodynamics L-bisabolol is an anti-inflammatory and natural moisturizer that has been found to reduce signs of photodamage, relieve itching, and improve skin texture and elasticity. 1. α-bisabolol is a monocyclic sesquiterpene alcohol naturally found in plants such as chamomile and vanilla [1,2]. 2. Its anticancer mechanism in non-small cell lung cancer involves a dual action: inducing apoptosis and blocking cell cycle progression through the Bax/Bcl-2/caspase pathway, while simultaneously inhibiting cell migration/invasion by suppressing the PI3K/AKT signaling pathway [1]. 3. Its renal protective effect against cisplatin-induced acute kidney injury depends on activating the Nrf2/HO-1 antioxidant pathway, thereby reducing the degree of kidney injury. Inflammatory response and inhibition of renal tubular cell apoptosis [2] 4. α-Bisabolol has good safety in vitro and in vivo, suggesting that it may be used as an adjunct therapy for non-small cell lung cancer and to prevent cisplatin-induced nephrotoxicity [1,2] |
| Molecular Formula |
C15H26O
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|---|---|
| Molecular Weight |
222.37
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| Exact Mass |
222.198
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| CAS # |
515-69-5
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| PubChem CID |
442343
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| Appearance |
Colorless to light yellow liquid
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| Density |
0.9±0.1 g/cm3
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| Boiling Point |
314.5±11.0 °C at 760 mmHg
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| Flash Point |
113.2±15.6 °C
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| Vapour Pressure |
0.0±1.5 mmHg at 25°C
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| Index of Refraction |
1.494
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| LogP |
5.07
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
16
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| Complexity |
284
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| Defined Atom Stereocenter Count |
2
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| SMILES |
CC(=CCC[C@@](C)([C@@H]1CC=C(C)CC1)O)C
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| InChi Key |
RGZSQWQPBWRIAQ-CABCVRRESA-N
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| InChi Code |
InChI=1S/C15H26O/c1-12(2)6-5-11-15(4,16)14-9-7-13(3)8-10-14/h6-7,14,16H,5,8-11H2,1-4H3/t14-,15+/m1/s1
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| Chemical Name |
(2S)-6-methyl-2-[(1S)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~449.70 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (11.24 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 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL 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: ≥ 2.5 mg/mL (11.24 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 25.0 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (11.24 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.4970 mL | 22.4850 mL | 44.9701 mL | |
| 5 mM | 0.8994 mL | 4.4970 mL | 8.9940 mL | |
| 10 mM | 0.4497 mL | 2.2485 mL | 4.4970 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.
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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