Product name: Taxifolin 7-rhamnoside
Synonym name: Dihydroquercetin 7-rhamnoside
Catalogue No.: BP2001
Cas No.: 137592-12-2
Formula: C₂₁H₂₂O₁₁
Mol Weight: 450.396
Botanical Source:
Physical Description:
Type of Compound:

Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
The product could be supplied from milligrams to grams. Inquire for bulk scale.
We provide solution to improve the water-solubility of compounds, thereby facilitating the variety of activity tests and clinic uses.

For Reference Standard and R&D, Not for Human Use Directly.

Description:

Taxifolin 7-O-rhamnoside is a natural product from Hypericum japonicum.

References:

Phytochemistry, 1991, 30(30):3152-3.    

A flavanonol rhamnoside from Hypericum japonicum.    

A new flavanonol (2R,3R)-taxifolin-7-rhamnoside(Taxifolin 7-O-rhamnoside), from whole plant of Hypericum japonicum has been isolated together with the known quercitrin and vincetoxicoside B. Their structures were elucidated using spectral techniques.    

HPLC of Taxifolin 7-rhamnoside

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

Dihydrotianjihuang glycoside: a natural flavonoid glycoside with multi-target pharmacological activity

1. Overview

Taxifolin 7-rhamnoside, also known as (+) - Dihydroquercetin 7-O - α - L-rhamnoside, is a naturally occurring dihydroflavonol glycoside compound. Its CAS number is 137592-12-2, molecular formula is C21H22O11, and molecular weight is approximately 450.39 g/mol. This compound is mainly derived from traditional medicinal plants Tianji Huang It was isolated from Hypericum japonicum (family Hypericum). Tianjihuang is commonly used in folk medicine to treat hepatitis, jaundice, and traumatic injuries. The modern pharmacological research on its active ingredients provides a scientific basis for traditional applications.

In recent years, with the deepening of research on natural products, dihydrotianjihuang glycoside has attracted attention due to its wide range of biological activities. Existing research reveals that it not only has significant antioxidant and free radical scavenging Ability, still there Antityrosinase、Inhibition of collagenase、anti-fibrotic It exhibits significant activity in various aspects. Its function involves multiple targets, including NQO1, SOD1, CAT, CYP2E1, and GSTP1, which are closely related to pathological processes such as oxidative stress, inflammatory response, and chemical liver injury. Therefore, dihydrotianjihuang glycoside is regarded as a lead compound with multi-target therapeutic potential, especially showing good application prospects in the fields of liver protection, skin photoprotection, and anti-inflammatory. This article will systematically elaborate on its chemical structure, plant origin, pharmacological mechanism, evaluation of medicinal properties, and research prospects.

2. Chemical structure and physicochemical properties

The chemical structure of dihydrotianjihuang glycoside is based on the Taxifolin skeleton, and an α - L-rhamnose group is attached to its hydroxyl group at position 7. The SMILES string is:C[C@H]1O[C@@H](Oc2cc(O)c3c(c2)O[C@@H](c2ccc(O)c(O)c2)[C@H](O)C3=O)[C@H](O)[C@@H](O)[C@H]1OIt displays its stereochemical configuration (multiple chiral centers) and glycosidic bond connection mode. This glycosylation modification typically affects the water solubility, bioavailability, and target selectivity of compounds.

From the analysis of pharmacological parameters:
- Molecular weight (MW)：450.3960 g/mol， Slightly higher than the 500 Da threshold recommended by Lipinski's Five Rules, but still within an acceptable range (usually natural products can be moderately relaxed).
- Lipid water partition coefficient (LogP)0.4301 indicates that the compound has moderate lipophilicity and leans towards hydrophilicity. Its LogD (at pH 7.4) is 0.3556, further confirming its good water solubility tendency in physiological pH environments.
- Topological Polarity Surface Area (TPSA)Up to 186.37 Å ², mainly due to the presence of multiple hydroxyl and sugar groups in the molecule, resulting in high polarity. High TPSA is usually unfavorable for passive transmembrane diffusion, but may be beneficial for interactions with polar targets.
- Water solubility The value is 4.1195 (usually measured in mg/mL or log mol/L, indicating good solubility), which is consistent with its high TPSA and multiple hydroxyl structures.
- Permeability The permeability of Caco-2 cells is 0.1440 (usually measured in units of × 10 ⁻⁶ cm/s), which is a low value, indicating that its oral absorption may be limited. BBB permeability is' low ', indicating that it is not easily able to penetrate the blood-brain barrier, which has a lower risk of central nervous system side effects, but also limits its use in brain diseases.
- Plasma protein binding rate (PPB)74.88%, belonging to moderate binding, may affect its free blood drug concentration and distribution.
- Toxicity warning Ames test is negative (0.0), indicating no mutagenicity; HERG inhibition is' no ', indicating a low risk of cardiac toxicity; However, the chromosomal aberration test is' present 'and further assessment of its genetic toxicity risk is needed. Other parameters such as skin sensitization, respiratory sensitization, and phototoxicity are all negative, indicating good safety.

In summary, dihydrotianjihuang glycoside is a natural glycoside compound with high polarity, good water solubility, but low membrane permeability. The glycosylation in its structure may affect its pharmacokinetic behavior in vivo through active transport or hydrolysis by gut microbiota (generating glycosides).

3. Plant sources and traditional applications

The main plant source of dihydrotianjihuang glycoside is Tianji Huang（Hypericum japonicum Thunb.）， Also known as ground ear grass or sparrow tongue grass, it belongs to the Hypericaceae family and the Hypericaceae genus of plants. This plant is widely distributed in East Asia and grows in various provinces south of the Yangtze River in China. It is commonly found in moist areas near fields and ditches.

In traditional medicine, the whole herb of Tianji Huang is used as medicine, with a bitter, pungent, and cool nature, and is associated with the liver, gallbladder, and large intestine meridians. Its application history is long, and its main functions include:
- Clear heat and eliminate dampness Used for treating liver and gallbladder diseases such as damp heat jaundice, hepatitis, cirrhosis ascites, etc. It is commonly consumed orally or externally by pounding it into soup in folk medicine.
- Detoxification and swelling reduction Used for carbuncles, sores, venomous snake bites, and injuries caused by falls, it has anti-inflammatory and analgesic effects.
- Relieve blood stasis and relieve pain Treat bruising, swelling, and pain caused by traumatic injuries.

Modern plant chemistry research has isolated various active ingredients from tianjihuang, including flavonoids (such as dihydrotianjihuang glycoside, quercetin derivatives), phloroglucinol, volatile oils, etc. Among them, flavonoids are considered to be an important material basis for their hepatoprotective and anti-inflammatory effects. Dihydrotianjihuang glycoside, as its characteristic glycoside component, directly links traditional applications with modern pharmacological activities (such as anti liver injury and antioxidant), reflecting the research paradigm of "traditional knowledge guiding modern discovery".

It is worth noting that the plant Hypericum perforatum, belonging to the same genus, is known for its antidepressant activity. Its main active ingredients are naphthoquinone compounds such as hyperoxin, which have significant differences in chemical composition spectrum from Tianjihuang. This suggests that the plants of the Primula genus have rich chemical diversity, and different species have different medicinal values.

4. Pharmacological activity and mechanism of action

Dihydrotianjihuang glycoside has a wide range of pharmacological activities, and its mechanism of action involves multi-target regulation. The core lies in its strong antioxidant capacity and regulatory effect on key enzymes.

4.1 Main pharmacological activities

1. Antioxidant and free radical scavenging The catechol structure in dihydrotianjihuang glycoside is the chemical basis for its antioxidant activity. It can directly neutralize reactive oxygen species (ROS) and reactive nitrogen species (RNS), interrupt free radical chain reactions, and protect cell membrane lipids, proteins, and DNA from oxidative damage.
2. Antityrosinase activity Tyrosinase is a key enzyme in melanin synthesis. Dihydrotianjihuang glycoside can effectively inhibit the activity of this enzyme, thereby reducing melanin production. This is for its skin whitening and Treating pigmentary disorders The application of (such as melasma) provides a basis.
3. Inhibition of collagenase Collagenases (such as matrix metalloproteinase-1, MMP-1) can degrade collagen, leading to wrinkles and sagging of the skin. The IC50 of dihydrotianjihuang glycoside for inhibiting collagenase is 193.3 μ M, indicating its ability to Anti skin photoaging Potential, helps maintain skin elasticity.
4. Anti fibrotic effect In fibrosis models of organs such as the liver and lungs, dihydrotianjihuang glycoside can inhibit fibroblast activation and reduce collagen deposition. Its mechanism is related to regulating the TGF - β/Smad signaling pathway and inhibiting inflammatory responses.
5. Other activities The study also reported that it has anti-inflammatory, cardioprotective, osteoblast differentiation promoting, osteoclast inhibition, and synergistic enhancement of anticancer drug activity.

4.2 Target and Mechanism Analysis

The five targets provided by the database (NQO1, SOD1, CAT, CYP2E1, GSTP1) reveal the core role of dihydroquercetin in the cellular defense system:

• NQO1 (NAD (P) H: quinone oxidoreductase 1)This is a phase II detoxifying enzyme that can catalyze the reduction of quinone compounds to hydroquinone, preventing the generation of semiquinone radicals and ROS. Dihydrotianjihuang glycoside may enhance the detoxification ability of cells towards quinone toxins by inducing or activating NQO1.
• SOD1 (Superoxide Dismutase 1) and CAT (catalase)Both are key enzymes in the endogenous antioxidant system. SOD1 converts superoxide anion (O ₂•⁻) into hydrogen peroxide (H ₂ O ₂), and CAT further decomposes H ₂ O ₂ into water and oxygen. Dihydroquercetin may enhance the antioxidant defense ability of cells by upregulating the activity or expression of these enzymes.
• CYP2E1 (Cytochrome P450 2E1)This is a phase I enzyme involved in the metabolism of exogenous substances, which can activate many prodrugs (such as acetaminophen and carbon tetrachloride) to produce hepatotoxic metabolites. Dihydrotianjihuang glycoside may be obtained through Inhibition of CYP2E1 Excessive activity reduces the generation of toxic metabolites, which is its Prevention and treatment of chemical liver injury One of the important mechanisms.
• GSTP1 (Glutathione S-transferase P1)This is an important II binding enzyme that can catalyze the binding of glutathione (GSH) to electrophilic toxins, promoting their excretion. Dihydrotianjihuang glycoside may enhance the GSH mediated detoxification pathway by inducing GSTP1 expression.

4.3 Association with related diseases (chemical liver injury)

Chemical liver injury Liver cell damage is caused by drugs, alcohol, environmental toxins, etc. Its core mechanism includes: ① CYP450 metabolism produces active intermediates; ② Oxidative stress and lipid peroxidation; ③ Inflammatory response; ④ Mitochondrial dysfunction.

Dihydrotianjihuang Glycoside Multi target synergistic effect Combat these pathological processes:
1. Source suppression Inhibit CYP2E1 and reduce toxin activation.
2. Antioxidant defense Directly eliminate free radicals and upregulate endogenous antioxidant enzymes such as SOD1, CAT, GSTP1, enhancing the liver's antioxidant capacity.
3. Detoxification enhancement Inducing NQO1 and GSTP1 to accelerate the harmless treatment and excretion of toxins and their metabolites.
4. Anti inflammation and anti fibrosis Reduce inflammatory cell infiltration and hepatic stellate cell activation, prevent acute injury from developing into chronic liver fibrosis.

Therefore, the protective effect of dihydrotianjihuang glycoside on chemical liver injury is Multidimensional and networked This reflects the advantage of multi-target action of natural products.

5. Evaluation of drug properties

Based on the provided pharmacokinetic parameters, combined with the Lipinski Rule of Five (Ro5) and general standards for drug development, the potential for the development of dihydrotianjihuang glycoside as a drug is evaluated as follows:

5.1 Evaluation based on Lipinski's Five Rules:

1. Molecular weight (MW)：450.39 < 500 Da（Comply with）。
2. Lipid water partition coefficient (LogP)：0.43 < 5（Comply with）。
3. Hydrogen bond donor (HBD)According to the structural formula, the molecule contains approximately 7-8 hydroxyl groups (including sugar groups), with a quantity greater than 5（not conform to， Ro5 recommendation ≤ 5).
4. Hydrogen bond acceptor (HBA)The molecule contains 11 oxygen atoms (all potential HBAs), with a quantity greater than 10（not conform to， Ro5 recommendation ≤ 10).
5. Number of rotatable keys Not directly provided, but there are many glycosidic and connecting bonds, possibly exceeding 10 (need to be calculated and confirmed, usually Ro5 is recommended to be ≤ 10).

Conclusion Dihydrotianjihuang glycoside violates the HBD and HBA rules in Ro5, which is consistent with its glycoside structure and high polarity characteristics. Ro5 is mainly used to predict the passive diffusion absorption of oral small molecules, and violating the rules usually indicates that the oral bioavailability may be low. However, many successful natural product drugs (such as cardiac glycosides and antibiotics) also violate Ro5, and they may be administered through active transport, prodrug modification, or non oral routes.

5.2 Analysis of Key Medicinal Parameters:

• absorb Low Caco-2 permeability (0.1440) and moderate Peff (0.6690, units may be x 10 ⁻⁴ cm/s) suggest poor oral absorption. This is directly related to its high TPSA (186.37) and multiple HBDs/HBAs. β - glucosidase in the intestine may hydrolyze it into aglycones (dihydroquercetin), which have lower LogP and slightly reduced polarity, and may improve absorption, but their bioavailability still needs to be validated through in vivo experiments.
• distribution BBB has low penetration and is mainly distributed in peripheral tissues. A moderate plasma protein binding rate (74.88%) means that approximately 25% exists in free form and is available for tissue uptake.
• Metabolism and excretion As a flavonoid glycoside, it may undergo metabolic processes such as intestinal microbiota hydrolysis and liver II binding (glucuronidation, sulfation). Further research is needed to determine whether it inhibits or induces CYP450 enzymes (excluding CYP2E1).
• toxicity Overall safety is good (Ames negative, hERG negative, no phototoxicity and sensitization). but Chromosomal aberration positive It is an important warning signal that must be evaluated for its risk through more in-depth genetic toxicity testing (such as micronucleus test, comet assay). Ser_LK and Ser_ST in liver enzyme indicators are "yes", indicating that they may affect liver function under specific conditions and require special attention in toxicology studies.

5.3 Potential and Optimization Direction of Medicinal Products:

Dihydrotianjihuang glycoside as lead compound Has clear multi-target pharmacological activity, especially suitable for development as Liver protective drugs or External skin preparation(such as anti-aging and whitening cosmetics). Its oral drug development faces challenges, and possible optimization strategies include:
1. Prodrug design Esterification and alkylation modification of polar hydroxyl groups to improve lipid solubility and membrane permeability, and release the active ingredient through hydrolysis in vivo.
2. Selection of administration route Develop injections (such as for acute liver injury), transdermal delivery systems, or topical formulations to avoid oral absorption issues.
3. Simplified structure Study its aglycone (dihydroquercetin) or simplified analogues to improve its pharmacological properties while maintaining its activity.
4. Formulation technology Using delivery technologies such as nanocrystals, liposomes, and cyclodextrin inclusion to improve its solubility and bioavailability.

6. Research Status and Application Prospects

6.1 Current research progress

At present, research on dihydrotianjihuang glycoside is still in progress Preclinical stage Mainly focused on:
- Activity screening and mechanism research It has been confirmed that it has in vitro and animal model activities in antioxidant, anti-inflammatory, hepatoprotective, and skin protective aspects, and its multi-target mechanism of action has been preliminarily elucidated.
- Extraction, Separation, and Synthesis Efficient extraction and separation from Tianjihuang have been achieved, and there have been reports of total synthesis routes, laying the foundation for its large-scale supply.
- Pharmacokinetic study Preliminary data suggests that its oral bioavailability may be low, and the metabolic pathway is mainly combined with II, requiring more systematic ADME research.

6.2 Future research directions and challenges

1. In depth study on the mechanism of action Using omics techniques (transcriptome, proteome, metabolome) to systematically reveal the network pathways regulated by it and search for more specific key targets.
2. Optimization of drug properties and development of dosage forms As mentioned earlier, solving the problem of poor absorption through chemical modification or novel delivery systems is the key to promoting its conversion into drugs.
3. Preclinical evaluation of the system Complete standardized pharmacological (different disease models), pharmacokinetic (absolute bioavailability, tissue distribution, metabolite identification), and toxicological (especially genetic toxicity and long-term toxicity) studies to provide data support for clinical trial applications.
4. Exploration of clinical indications Based on existing evidence, the most promising indications include:
5. Adjuvant therapy for chemical liver injury(such as drug-induced liver injury, alcoholic liver disease).
6. Dermatology applications As a functional cosmetic ingredient, it is used for whitening, wrinkle resistance, and sun protection.
7. Chronic inflammatory diseases Such as osteoarthritis (combined with its regulation of bone metabolism activity), pulmonary fibrosis, etc.
8. Combination therapy research Explore its synergistic effect with existing drugs such as antiviral drugs and chemotherapy drugs to improve efficacy or reduce side effects.

6.3 Outlook

Dihydrotianjihuang glycoside, as a natural active ingredient discovered from traditional medicinal plants, perfectly embodies the value of natural products in drug discovery: providing novel chemical frameworks and multi-target modes of action. Despite facing challenges in physicochemical properties and pharmacokinetics on its path to becoming a drug, these challenges are expected to be overcome through modern medicinal chemistry and pharmaceutical methods. With the increasing emphasis on multi-target and network pharmacology treatment strategies, compounds such as dihydrotianjihuang glycoside that can simultaneously regulate oxidative stress, detoxifying enzyme systems, and inflammatory pathways may have advantages over single target drugs in the treatment of complex diseases such as metabolic liver disease and chronic inflammation. In the future, it is expected to be developed into a new type of liver protective drug or skin protectant, bringing new choices to human health.

Statement This article is based on existing public data and scientific research, and its content is for professional communication and reference only. It does not constitute any medical or investment advice. The development of compounds requires rigorous preclinical and clinical trial validation.