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Synonym name: Populnin
Catalogue No.: BP0825
Cas No.: 16290-07-6
Formula: C21H20O11
Mol Weight: 448.38
Botanical Source: Thespesia populnea and many other plant spp.
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Can be supplied from milligrams to grams.
For Reference Standard and R&D, Not for Human Use Directly.
Inquire for bulk scale.
HNMR-山奈酚-7-O-葡萄糖苷-Kaempferol-7-O-β-D-glucopyranoside
HPLC of Kaempferol-7-O-beta-D-glucopyranoside
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
190.2800
.0879
-.0372
1.1903
.5381
.0787
Low
80.8812
3.8940
Yes
No
No
No
Yes
No
0.6
Yes
No
Yes
No
Kaempferol-7-O-glucopyranoside (CAS No. 16290-07-6) is a typical flavonoid compound, mainly isolated from the flowers of Malus pumila mill., a plant of the genus Malus. As an important member of flavonoid natural products, kaempol-7-O-glucoside has attracted widespread attention in pharmacology and natural product chemistry in recent years due to its unique chemical structure and diverse bioactivity. It mainly exhibits significant antioxidant, anti-inflammatory, and procoagulant activities, demonstrating potential application value in the prevention and treatment of various diseases.
Antioxidant damage is an important pathological basis for the occurrence and development of various chronic diseases, such as neurodegenerative diseases, cardiovascular diseases, and inflammatory diseases. Kaempol-7-O-glucoside regulates various antioxidant-related targets such as NFE2L2 (NRF2), SOD1, CAT, GPX1, HMOX1, and SOD2, effectively alleviating oxidative stress and protecting cells from free radical damage. Moreover, its anti-inflammatory effect is closely related to regulating the expression of pro-inflammatory factors, further expanding its potential application in inflammatory diseases. This paper will systematically review the chemical structure and physicochemical properties of kaempol-7-O-glucoside, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, and pharmacokinetic characteristics, and explore its clinical application prospects and future research directions.
Kaempol-7-O-glucoside belongs to the flavonoid glycoside class of flavonoid compounds, with a molecular formula C21H20O11 and a molecular weight of 448.38. Its structural core is kaempferol, which is connected to the β-D-glucoside bond via a 7-hydroxyl group to form 7-O-glucoside. This structure imparts high polarity and water solubility, with a TPSA (topological pole surface area) of 190.28 Ų, indicating it has strong polar groups, especially multiple hydroxyl and glycoside groups.
In terms of physicochemical properties, the LogP value of kaempole-7-O-glucoside is 0.0879, indicating strong hydrophilicity, and water solubility of 1.1903, suitable for biological activity in aqueous phase systems. Its molecular structure contains multiple hydroxyl groups, which can form hydrogen bonds with biological macromolecules, enhancing their biological activity and targeted binding ability. The low permeability of the blood-brain barrier suggests that its direct effect on the central nervous system may be limited, but this also reduces the potential risk of toxicity in the central nervous system. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames mutagenic test scored 0.6, indicating a low genotoxicity risk and a solid safety foundation.
Kaempol-7-O-glucoside mainly comes from the flowers of Malus pumila mill., a plant of the genus Malus. This plant is widely distributed in temperate regions, and its flowers are rich in various flavonoids and polyphenolic compounds, making it an important resource in traditional medicinal and food industries. After flower collection, they are usually dried and crushed to facilitate extraction.
The extraction method mostly uses solvent extraction combined with column chromatography for separation and purification. Common solvents include ethanol, water, methanol, and their mixed solvent systems. The typical process is: repeatedly reflux extraction of the dried powder with 70% ethanol, filtering and concentration, and then separating and purifying by silica gel column chromatography or reversed-phase high-performance liquid chromatography (RP-HPLC). Purity testing is mostly confirmed using HPLC-UV and mass spectrometry techniques. In recent years, green extraction technologies such as ultrasound-assisted extraction (UAE) and microwave-assisted extraction (MAE) have also been applied to improve extraction efficiency and purity.
The antioxidant effect of kaempol-7-O-glucoside is one of its most notable pharmacological properties. In vitro studies have shown that this compound can effectively scavenge free radicals (such as DPPH and ABTS free radicals), inhibit lipid peroxidation, and protect cells from oxidative stress damage. In cell models, kaempol-7-O-glucoside significantly enhances intracellular superoxide dismutase (SOD), catalase (CAT), and glutathione peroxidase (GPX1) activity, lowers reactive oxygen species (ROS) levels, and alleviates oxidative damage.
In animal experiments, kaempol-7-O-glucoside activates the NFE2L2 (NRF2) signaling pathway, inducing downstream antioxidant enzyme expression such as HMOX1, enhancing the body's antioxidant defense capacity, reducing myocardial ischemia-reperfusion injury and nerve cell oxidative damage, and demonstrating good protective effects.
Inflammatory responses are common pathological processes in various diseases. Kaempol-7-O-glucoside inhibits the expression of pro-inflammatory factors such as TNF-α, IL-1β, and IL-6, reducing the release of inflammatory mediators and demonstrating a significant anti-inflammatory effect. Its mechanism of action is partly attributed to inhibiting activation of the NF-κB signaling pathway, reducing the transcription of inflammatory genes. Additionally, this compound can regulate the MAPK pathway, further suppressing inflammatory responses.
There is limited research on the activity of Kaempol-7-O-glucoside in promoting coagulation, but existing data indicate it can promote platelet aggregation and shorten clotting time, possibly by regulating coagulation factor activity and platelet function. This characteristic suggests its potential application value in hemostasis and wound repair, but its potential thrombosis risk should also be watched.
The main mechanism of action of kaempol-7-O-glucoside focuses on regulating antioxidant and anti-inflammatory signaling pathways. Its core target is NFE2L2 (NRF2), a key regulator of cellular antioxidant defense. Kaempol-7-O-glucoside promotes NRF2 nuclear translocation, enhances its binding to antioxidant reaction elements (AREs), induces the expression of downstream antioxidant enzymes such as SOD1, SOD2, CAT, GPX1, and HMOX1, and enhances cellular ability to clear ROS.
Additionally, this compound inhibits the NF-κB signaling pathway, reducing the expression of pro-inflammatory cytokines and alleviating inflammatory responses. Its regulation of the MAPK pathway further improves the anti-inflammatory mechanism.
Procoagulant activity may involve regulation of platelet membrane receptor and coagulation factor activity, but specific molecular targets remain unclear and require further research.
Druggability evaluation of kaempol-7-O-glucoside shows good safety and efficacy potential. The molecular weight is 448.38, moderate, with LogP close to zero, indicating strong hydrophilicity, which is beneficial for oral absorption and internal distribution. A higher TPSA value suggests greater polarity, which may limit cell membrane permeability, especially the lower permeability of the blood-brain barrier, which may restrict the central nervous system's function.
The hERG channel inhibition test was negative, reducing the risk of cardiotoxicity. The Ames trial scored 0.6, indicating a low genotoxicity risk and good safety.
In terms of pharmacokinetics, current research on metabolism and excretion in vivo is relatively limited. Considering its glycoside structure, it may be hydrolyzed by gut microbes and liver enzyme systems to form kaempamol, which has higher biological activity and better pharmacokinetic properties. In the future, systematic research is needed on its absorption, distribution, metabolism, and excretion (ADME) characteristics to guide clinical application and formulation design.
With its remarkable antioxidant and anti-inflammatory activities, kaempol-7-O-glucoside shows broad application prospects in various oxidative stress-related diseases. It has potential preventive and therapeutic value in cardiovascular diseases, neurodegenerative diseases, chronic inflammatory diseases, and metabolic syndromes.
Moreover, its procoagulant activity offers new ideas for hemostasis and wound repair, but the risk of thrombosis should be carefully assessed. In the future, structural modification and drug carrier technologies can optimize their pharmacokinetic performance to improve bioavailability and targeting.
In terms of clinical translation, systematic toxicological evaluation and preclinical efficacy validation are still needed to clarify effective dosage and safety ranges. Combining modern drug development technologies, such as nanocarriers, sustained-release formulations, and combination drug strategies, is expected to accelerate its clinical application.
As an important natural flavonoid product, kaemprol-7-O-glucoside demonstrates promising pharmacological potential and pharmaceutical prospects due to its unique chemical structure and diverse biological activities. By regulating key antioxidant signaling pathways such as NFE2L2/NRF2, it exerts significant antioxidant and anti-inflammatory effects, providing a new molecular basis and drug candidate for the prevention and treatment of related diseases.
Future research should focus on further elucidating its molecular mechanisms, optimizing extraction and synthesis processes, improving pharmacokinetics and safety evaluations, and promoting its translation into clinical application. With continuous advances in natural product pharmacology and drug development technologies, kaempol-7-O-glucoside is expected to become an important representative in the development of natural flavonoid drugs, contributing new strength to human health.
Shenshuai
Wenjing
Hedandan
