Product name: Taraxerol
Synonym name: Skimmiol; Alnulin
Catalogue No.: BP1365
Cas No.: 127-22-0
Formula: C₃₀H₅₀O
Mol Weight: 426.729
Botanical Source: Taraxacum officinale (dandelion), Alnus spp., Skimmia japonica, Rhododendron spp., Euphorbia spp. and other plants. Rather widely distributed. Also the lichen Pertusaria ophthalmiza (poss. not a genuine lichen constit.)
Physical Description: Powder
Type of Compound: Triterpenoids

Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle

Storage: Store in a well closed container, protected from air and light. Put into refrigerate or freeze for long term storage.
Whenever 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 -20℃. Generally, these will be useable for up to two weeks.

The product could be supplied from milligrams to grams, up to kilograms
Inquire for bulk scale.

Descriptions:
Taraxerol, a triterpenoid compound, has potent anti-inflammatory effects,it downregulates the expression of proinflammatory mediators in macrophages by interfering with the activation of TAK1 and Akt, thus preventing NF-κB activation. [1]
Taraxerol can produce triterpenoid anti-cancer compound in Agrobacterium-transformed root cultures of butterfly pea (Clitoria ternatea L.).[2]
Taraxerol can be used as a lipid biomarker for mangrove input to the SE Atlantic, the proxy-environment relations for taraxerol and Rhizophora pollen down-core show that increased taraxerol and Rhizophora pollen abundances occur during transgressions and periods with a humid climate, these environmental changes modify the coastal erosion and sedimentation patterns, enhancing the extent of the mangrove ecosystem and/or the transport of mangrove organic matter offshore.[3]
Taraxerol has inhibitory effects on AGS cell growth through inducing G2/M arrest and promotion of cell apoptosis, taraxeryl acetate has less effect on cell cycle arrest and apoptosis of AGS cells than taraxerol.[4]

References:
[1] Yao X, Li G, Bai Q, et al. Int Immunopharmacol, 2013, 15(2):316–24.
[2] Swain S S, Rout K K, Chand P K. Appl Biochem Biotech, 2012, 168(3):487-503.
[3] Versteegh G J M, Schefu? E, Dupont L, et al. Geochim Cosmochim Ac, 2004, 68(3):411-22.
[4] Tan B, Shi H L, Ji G, et al. Journal of Chinese Integrative Medicine, 2011, 32(6):1278-84.
[5] Kumar V, Mukherjee K, Kumar S, et al. Phytochem Anal, 2008, 19(19):244-50.

HPLC of Taraxerol

Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃

Introduction/Overview

Natural products, as an important treasure trove for drug discovery, play an irreplaceable role in the history of human disease prevention and treatment. Among them, triterpenoids have always been a hot topic in medicinal chemistry and pharmacology research due to their extensive and significant biological activities. Taraxerol (CAS number: 127-22-0), a pentacyclic triterpenoid compound widely present in various medicinal plants, has attracted much attention in recent years due to its outstanding pharmacological activities in anti-inflammatory, anticancer, and liver protection. Its name comes from its earliest isolation from Taraxacum plants, but subsequent research has found that it is also distributed in various traditional medicinal plants such as lychee leaves, loquat leaves, and water chestnuts. Modern pharmacological studies have shown that the core mechanism of action of dandelion terpenoids is closely related to the regulation of key inflammatory signaling pathways such as nuclear factor kappa B (NF - κ B), and can effectively induce tumor cell apoptosis. Especially in oxidative stress and inflammation related disease models such as alcoholic liver injury, dandelion terpenoids have shown the potential to exert protective effects by regulating the expression of tumor necrosis factor alpha (TNF - α), interleukin (IL-6, IL-1 β), inducible nitric oxide synthase (NOS2), and a series of oxidoreductases such as SOD, CAT, NQO1, CYP2E1. This article aims to systematically review the chemical properties, plant sources, pharmacological activities, molecular mechanisms of action, pharmacological parameters, and clinical application prospects of dandelion terpenoids, in order to provide comprehensive scientific references for the deep development and transformation research of this natural product.

Chemical structure and physicochemical properties

The chemical name of dandelion terpenol is (3 β) - D-Friedolean-14-en-3-ol, with a molecular formula of C30H50O and a molecular weight of 426.7290. Its basic skeleton is a pentacyclic triterpene of Oleanane type, but there is a double bond between positions C-13 and C-14, belonging to the D-friedooleanane structural type. Its C-3 position is replaced by a β - configured hydroxyl group, which is one of the key functional groups for its biological activity.

From the analysis of physical and chemical properties, dandelion terpenoids exhibit typical characteristics of triterpenoids. Its lipid water partition coefficient (LogP) is as high as 8.6065, indicating that the compound has extremely strong lipophilicity. Consistent with this, its water solubility is extremely low, about 0.0001 mg/mL, which poses the primary challenge for its formulation development. Its topological polar surface area (TPSA) is relatively small, only 20.23 Å ², further confirming its low molecular polarity. Based on these properties, computer models predict that dandelion terpenoids have a high blood-brain barrier permeability, indicating their potential application value in central nervous system related diseases. In early safety screening, the compound did not show significant hERG potassium channel inhibitory activity (low risk of arrhythmia) and Ames test mutagenicity (result 0.0), providing preliminary evidence for its relatively safe pharmacological properties.

Plant sources and extraction methods

Dandelion terpenoids are widely distributed in nature and mainly exist in the roots, stems, leaves, bark, and resin of various dicotyledonous plants.
1. Main plant sources：
* Dandelion genus Taraxacum officinale, also known as medicinal dandelion, is the earliest source of its isolation and naming.
* Unprotected Child Health The leaves and seeds of Litchi chinensis are important resources rich in dandelion terpenoids.
* Rosaceae Like the leaves of Eriobotrya japonica.
* Solanaceae family Like the roots and fruits of Solanum torvum.
* Other It has also been reported in various medicinal plants such as Euphorbiaceae, Fabaceae, and Euonymus.

1. Extraction and Separation Methods：
   Due to the strong lipophilicity of dandelion terpenoids, their extraction is usually carried out using organic solvent methods. The standard process includes:
   • Extract Dry and crushed plant materials are subjected to cold soaking, reflux, or ultrasound assisted extraction using moderately polar organic solvents (such as methanol, ethanol, acetone) or mixed solvents. Due to its low polarity, low polarity solvents such as ethyl acetate or chloroform are often used for liquid-liquid extraction and enrichment in the future.
   • Separation and purification The crude extract is initially separated by silica gel column chromatography using gradient elution systems such as petroleum ether ethyl acetate or chloroform methanol. Further purification can be achieved through reverse phase silica gel column chromatography (such as ODS, methanol water system), preparative thin-layer chromatography, or high-performance liquid chromatography (HPLC, commonly using C18 column and acetonitrile water as mobile phase). Modern technologies such as high-speed countercurrent chromatography (HSCCC) have also been applied for efficient separation of dandelion terpenoids due to their advantages of large preparation capacity and avoiding irreversible adsorption.
   • appraisal The purified compound was structurally confirmed by nuclear magnetic resonance (NMR, including 1H, 13C, 2D NMR), mass spectrometry (MS), infrared spectroscopy (IR), and chromatographic behavior compared to standard samples (such as TLC, HPLC).

Pharmacological activity research

A large number of pharmacological experiments in vitro and in vivo have confirmed that dandelion terpenoids have various biological activities, among which anti-inflammatory, anticancer, and liver protective effects are the most prominent.

1. anti-inflammatory activity Dandelion terpenoids have shown significant anti-inflammatory effects in various acute and chronic inflammation models. In acute inflammation models induced by carrageenan or acetic acid in mice, it can effectively reduce paw swelling and increase vascular permeability. Its anti-inflammatory effect is not limited to the periphery. In the lipopolysaccharide (LPS) - induced microglial activation model, it can inhibit the release of inflammatory mediators, suggesting its potential intervention effect on neuroinflammation.

2. anticancer activity Taraxacum terpenoid alcohol can inhibit the growth and induce apoptosis of many human cancer cell lines, including breast cancer (such as MCF-7, MDA-MB-231), colon cancer (such as HCT-116, HT-29), lung cancer (such as A549), liver cancer (such as HepG2), etc. Its anti-cancer mechanisms are diverse, including inducing apoptosis, blocking the cell cycle (often blocking cells in G0/G1 or G2/M phases), inhibiting cell migration and invasion (anti metastatic potential), and inducing autophagy.

3. Liver protective effect This is an active field of dandelion terpenoids that has received much attention in recent years, especially in the study of alcoholic liver injury models. Research has shown that pretreatment with dandelion terpenoids can significantly improve liver pathological damage caused by alcohol exposure, such as steatosis and inflammatory infiltration, and reduce serum transaminase (ALT, AST) levels. Its hepatoprotective effect is closely related to reducing oxidative stress and inhibiting inflammatory response.

4. Other activities In addition, the study also reported that taraxelian terpene alcohol has potential activities such as antibacterial, anti diabetes, anti osteoporosis, and cardiovascular protection, showing its multi target effect.

Mechanism of action and molecular targets

The pharmacological effects of dandelion terpenoids, especially anti-inflammatory and liver protective effects, involve the regulation of complex signaling networks and multiple molecular targets.

1. Core signaling pathway: inhibition of NF - κ B pathway NF - κ B is a key transcription factor that regulates inflammation, cell survival, and proliferation. Dandelion terpenoids have been proven to effectively inhibit NF - κ B activation induced by stimuli such as LPS and TNF - α. Its mechanism includes inhibiting the phosphorylation and degradation of I κ B α, preventing the nuclear translocation of p65 subunit, thereby downregulating the expression of a series of pro-inflammatory cytokines and enzymes, such as TNF-α、IL-6、IL-1βand Inducible nitric oxide synthase (NOS2)This is the core mechanism of its anti-inflammatory and induction of apoptosis in certain cancer cells.

2. Multi target regulation in alcoholic liver injury The core pathological processes of alcoholic liver injury are oxidative stress and inflammation. Dandelion terpenoids exhibit multi-target protective effects during this process:

   • Inhibit oxidative stress Key enzymes in alcohol metabolism Cytochrome P450 2E1 (CYP2E1)Overactivation is the main source of reactive oxygen species (ROS) production. Dandelion terpenoids can downregulate the expression of CYP2E1 and reduce ROS generation. Meanwhile, it can upregulate key molecules of the endogenous antioxidant defense system, including Superoxide dismutase (SOD1, SOD2)、Catalase (CAT)、Quinone oxidoreductase 1 (NQO1)and Glutathione S-transferase P1 (GSTP1)Thus enhancing the ability of cells to eliminate free radicals.
   • Regulating inflammation and apoptosis By inhibiting the NF - κ B pathway, reducing TNF-α、IL-6、IL-1βThe production of pro-inflammatory cytokines can alleviate liver inflammation infiltration. The decrease in TNF - α levels also helps alleviate its mediated hepatocyte apoptosis. In addition, it can regulate the Bcl-2/Bax ratio, activate the caspase cascade reaction, and may initiate protective autophagy or clear severely damaged cells in damaged liver cells.

3. Mechanism of inducing cell apoptosis In cancer cells, the pathways through which dandelion terpenoids induce apoptosis include mitochondrial pathway (mitochondrial membrane potential decrease, cytochrome c release), death receptor pathway (such as regulating Fas/FasL), and endoplasmic reticulum stress pathway. Its upstream signals typically involve the regulation of survival and stress signaling pathways such as PI3K/Akt and MAPK (such as JNK, p38).

Evaluation of drug properties and pharmacokinetics

Although the pharmacological activity of dandelion terpenoids is clear, there are significant challenges in their drug liking, mainly due to their extreme physicochemical properties.

1. Drug Challenge：

   • Solubility and permeability The extremely high LogP value (8.6065) and low water solubility are the biggest obstacles to its conversion to drugs. This can lead to poor oral absorption and low bioavailability. Although high lipophilicity may facilitate its penetration through cell membranes, excessive lipophilicity can also lead to abnormal distribution in the body, making it prone to accumulation in adipose tissue and potentially affecting its effective binding to targets.
   • Pharmacokinetic (PK) characteristics The pharmacokinetic research data of existing publicly available systems are relatively limited. Based on its properties, it can be inferred that it may be slowly and incompletely absorbed after oral administration, widely distributed in the body (predicted to cross the blood-brain barrier), mainly metabolized by the liver (CYP450 enzyme system), and metabolites may be excreted through bile or feces. The specific metabolic pathways, half-life, absolute bioavailability, and other key PK parameters urgently need to be clarified through standardized preclinical studies.

2. Formulation strategy and structural optimization：

   • New drug delivery system To improve its water solubility and bioavailability, researchers are exploring various formulation technologies, including nanocrystals, solid dispersions, liposomes, micelles, cyclodextrin inclusion complexes, and self microemulsion delivery systems. These technologies aim to increase their dissolution rate, improve solubility, and stability.
   • Prodrug design By chemically modifying its C-3 hydroxyl group and introducing hydrophilic groups (such as phosphate esters, amino acid esters, polyethylene glycol chains), water-soluble prodrugs can be prepared, which can be released in vivo through enzymatic interpretation to improve their pharmaceutical properties.
   • Structural modification Using its parent nucleus as a template for semi synthetic modification, exploring derivatives with better activity and more balanced physicochemical properties is a key direction in pharmaceutical chemistry research.

Clinical application prospects and prospects

Dandelion terpenoids, as a lead compound, have broad clinical application prospects, but the road ahead is long.

1. Potential therapeutic areas：

   • Chronic inflammatory diseases Such as rheumatoid arthritis, inflammatory bowel disease, neurodegenerative diseases related to neuroinflammation, etc.
   • Chemical Prevention and Adjuvant Anti Cancer As a natural source of chemopreventive agent, or in combination with existing chemotherapy drugs, it enhances efficacy and reduces side effects. Its anti transfer properties are also worth paying attention to.
   • Metabolic Liver Disease Not only alcoholic liver disease, but also in non-alcoholic fatty liver disease (NAFLD)/non-alcoholic steatohepatitis (NASH) models, as it simultaneously targets the two core mechanisms of oxidative stress and inflammation.
   • Other Based on its antioxidant and anti-inflammatory properties, it also has potential for exploration in fields such as skin inflammation and metabolic syndrome.

2. Future research directions and challenges：

   • In depth mechanism research It is necessary to use techniques such as gene knockout/knock in, proteomics, metabolomics, etc. to more accurately elucidate its direct target (whether it is a protein target or not) and upstream and downstream signaling networks.
   • Systematic pharmacokinetic/toxicological evaluation It is necessary to conduct standardized preclinical ADMET (absorption, distribution, metabolism, excretion, and toxicity) studies to clarify its in vivo processes, treatment window, and potential toxicity, providing a basis for clinical trial design.
   • Breakthrough in formulation development A successful formulation strategy is the key to driving it towards clinical practice. We need to develop stable, controllable, and highly bioavailable dosage forms.
   • Clinical translational research Ultimately, strict Phase I, II, and III clinical trials are required to validate its safety, efficacy, and optimal medication regimen in humans.

Conclusion

Dandelion terpenoids, as a naturally occurring pentacyclic triterpenoid compound, have shown remarkable potential in anti-inflammatory, anticancer, and liver protection fields due to their multiple pharmacological mechanisms, including inhibition of the NF - κ B pathway, regulation of oxidative stress and inflammation balance, and induction of tumor cell apoptosis. Its multidimensional regulation of key targets such as TNF - α, NOS2, CYP2E1, SOD, NQO1, etc. in the alcoholic liver injury model highlights the advantages of its multi-target effect. However, its extreme lipophilicity and low water solubility constitute the main bottlenecks in its conversion to drugs. Future research should focus on overcoming drug defects through advanced formulation techniques, prodrug strategies, or rational structural modifications, supplemented by systematic and in-depth mechanistic and pharmacokinetic studies. With the gradual resolution of these scientific issues, dandelion terpenoids are expected to develop from a promising natural lead compound into innovative drug candidates for the treatment of inflammation related diseases and liver diseases, contributing their unique value to human health.