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Product name: Rhamnocitrin
Synonym name:
Catalogue No.: SBP02530
Cas No.: 569-92-6
Formula: C16H12O6
Mol Weight: 300.266
Botanical Source:
Type of Compound: Flavonoids
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
Inquire for bulk scale.
For Reference Standard and R&D, Not for Human Use Directly.
HPLC of Rhamnocitrin
HNMR of Rhamnocitrin
HNMR of Rhamnocitrin
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
110.3800
2.1600
1.8900
Low
3.5400
null
No
No
No
No
No
Negative
null
Rhamnocitrin (CAS No.: 569-92-6) is a naturally occurring flavonoid compound that has attracted widespread attention in pharmacology due to its remarkable anti-inflammatory and antioxidant activities. In recent years, as the incidence of chronic inflammatory diseases and oxidative stress-related pathological conditions continues to rise, research on natural products as potential therapeutic agents has continued to gain attention. Rhamnosis limonin, with its unique molecular structure and multi-target regulatory capability, exhibits selective inhibition of oxidative stress and inflammatory responses in vascular endothelial cells and neurons, making it an important molecular tool for studying anti-inflammatory, antioxidant, and neuroprotective mechanisms.
This review aims to systematically summarize the chemical structure and physicochemical properties of rhamnoderma limonin, plant origins and extraction methods, thoroughly analyze its pharmacological activity and mechanism of action, evaluate its druggability and pharmacokinetic characteristics, and explore its clinical application prospects in vascular endothelium-related inflammatory diseases and neuroprotection, striving to provide theoretical basis and research directions for subsequent basic research and clinical translation.
Rhamnosis limonin belongs to the flavonoid class of compounds with a molecular formula of C16H14O6 and a molecular weight of 290.26. Its chemical structure typically includes a flavonoid backbone, with multiple hydroxyl and methoxy substituents, giving it excellent bioactivity. In terms of structure, rhamnosis limonin has a relatively high number of hydroxyl groups (6 hydrogen bond receptors), which helps it form stable hydrogen bond interactions with various protein targets, thereby regulating signaling pathways.
In terms of physicochemical properties, the LogP value of rhamnosis limonin was 2.16, indicating moderate lipid solubility, which is beneficial for cell membrane penetration and distribution in vivo. Its topological pole surface area (TPSA) is 110.38 Ų, indicating good solubility in polar environments, but low blood-brain barrier permeability (BBB), which may limit its direct action in the central nervous system. Toxicological evaluation showed that rhamnosis limonin was not hepatotoxic or cardiotoxic, and did not inhibit hERG channels. Ames-induced mutagenic tests were negative, indicating high safety and promising drug potential.
Rhamnus limonin is mainly found in various plants, especially abundant in Rhamnus spp. and lemon species. Its natural sources include the bark, leaves, and fruit of the rhamna. Plants containing these flavonoids in traditional Chinese medicinal materials are often used to treat inflammatory and oxidative stress-related diseases.
In terms of extraction methods, organic solvent extraction combined with column chromatography is commonly used. The specific steps usually include:
In recent years, the application of ultrasound-assisted extraction and microwave-assisted extraction technologies has improved extraction efficiency and purity, while reducing solvent usage, aligning with the concept of green chemistry.
Rhamnosis limonin exhibits significant anti-inflammatory effects, mainly by inhibiting inflammatory signaling pathways and downstream expression of pro-inflammatory factors. In vitro studies have shown that rhamnoderma limonin can selectively inhibit inflammatory responses in vascular endothelial cells and nerve cells, reduce the release of pro-inflammatory cytokines such as IL-6 and IL-8, and decrease the expression of adhesion molecules ICAM-1 and VCAM-1, thereby blocking the migration and adhesion of inflammatory cells.
In animal models, rhamnosis limonin demonstrated protective effects against vascular endothelium-related inflammatory diseases such as sepsis, acute lung injury, and atherosclerosis, significantly reducing tissue damage and inflammatory responses, indicating its potential clinical value.
As a natural antioxidant, rhamnosis limonin can efficiently scavenge free radicals. In DPPH radical scavenging experiments, its IC50 is 28.38 mM, demonstrating excellent free radical scavenging ability. Its antioxidant effects are not only reflected in directly scavenging free radicals but also by regulating the intracellular antioxidant enzyme system.
Rhamnosis limonin upregulates the expression of heme oxygenase HO-1, enhancing cellular antioxidant defense capacity. At the same time, it regulates the ERK/p38 MAPK signaling pathway, promotes the expression of antioxidant enzymes such as SOD1, CAT, and GPX1, reduces oxidative stress damage, and protects cellular function integrity.
In neural cell models, rhamnosis limonin has a significant protective effect against oxidative damage in PC12 cells. By inhibiting apoptosis induced by oxidative stress, maintaining intracellular calcium homeostasis, and reducing nerve cell damage, it suggests its potential application value in neurodegenerative diseases and cerebrovascular lesions.
The pharmacological effects of rhamnosis limonin involve multiple signaling pathways and molecular targets, forming a complex regulatory network.
Rhamnosis limonin upregulates miR-185 expression to inhibit the controlled calcium immigration (SOCE) mediated by STIM-1 (stromal interaction molecule 1). STIM-1, as a key regulator of intracellular calcium signaling, has activity that influences calcium homeostasis and downstream signaling. Inhibition of SOCE blocks the relocation of the calcium-dependent transcription factor NFATc3 (nuclear factor of activated T cells, cytoplasmic 3) into the nucleus, thereby reducing the transcription and expression of pro-inflammatory factors.
NFATc3 is a key transcription factor in inflammatory responses, regulating the expression of various inflammatory mediators. Rhamnoderma limonin reduces the production of pro-inflammatory cytokines such as IL-6 and IL-8 by inhibiting NFATc3 nuclear translocation, thereby alleviating inflammatory responses.
Rhamnosis limonin regulates the ERK and p38 MAPK pathways, bidirectionally regulating cellular antioxidant and anti-inflammatory responses. By activating ERK/p38 MAPK, it promotes the expression of antioxidant enzymes and enhances cells' resistance to oxidative stress; At the same time, it suppresses pro-inflammatory signals, reducing the activity of adhesion molecules and inflammatory factors.
Rhamnosis limonin promotes activation of the NFE2L2 (nuclear factor red-related factor 2, NRF2) signaling pathway, enhances the expression of intracellular antioxidant enzymes such as SOD1, SOD2, CAT, GPX1, and HMOX1, improves cells' ability to scavenge reactive oxygen species (ROS), and reduces oxidative damage.
Rhamnosis limonin may also influence extracellular matrix matrix remodeling by regulating matrix metalloproteinases MMP1 and MMP3, participating in the regulation of the inflammatory microenvironment, and further exerting its anti-inflammatory and tissue-protective effects.
The molecular weight of rhamnosis limonin is 290.26, which complies with the Lipinski rule and is beneficial for oral absorption. A LogP value of 2.16 indicates moderate lipid solubility, balancing water and lipid solubility, which is beneficial for distribution in vivo. TPSA was 110.38 Ų, indicating moderate polarity, but lower blood-brain barrier permeability, limiting its direct effect in the central nervous system.
Toxicological evaluation showed that rhamnosis limonin was not hepatotoxic or cardiotoxic, did not inhibit hERG channels, was negative in Ames test, and had a relatively high safety. Its good safety lays the foundation for clinical application.
Pharmacokinetics, existing research is limited, suggesting that the oral bioavailability of rhamnamous limonin is moderate, and metabolism in the body mainly occurs through hepatic enzyme systems, with metabolites possibly involved in hydroxylation and methylation modifications. Future research on in vivo pharmacokinetics is needed to clarify its absorption, distribution, metabolism, and excretion characteristics, providing a basis for dosage form development and clinical administration regimens.
Rhamnosis limonin has broad clinical application potential due to its multi-target anti-inflammatory and antioxidant effects.
Diseases such as sepsis, acute lung injury, and atherosclerosis are closely related to vascular endothelial inflammation and oxidative stress. Rhamnosis limonin has potential therapeutic value by inhibiting STIM-1/NFATc3 and modulating the MAPK pathway, thereby alleviating endothelial cell inflammatory responses and oxidative damage. In the future, animal models and clinical samples can be combined to verify efficacy and safety, promoting clinical translation.
Although the blood-brain barrier permeability of rhamnosis limonin is relatively low, its antioxidant and anti-inflammatory protective effects in neural cell models suggest its potential as an auxiliary neuroprotective agent or by structural modification to improve brain accessibility, applicable in the treatment of neurodegenerative diseases and cerebrovascular diseases.
Given its ability to regulate multiple signaling pathways, rhamnosis limonin may also be applied in chronic inflammation, autoimmune diseases, and tumor microenvironment regulation. By combining modern drug design technologies with the development of derivatives or combination drug strategies, their clinical application scope will be expanded.
Rhamnosis limonin, a natural flavonoid compound with significant anti-inflammatory and antioxidant activities, demonstrates broad research and application prospects in vascular endothelial inflammation and neuroprotection due to its multi-target regulatory capabilities. Its excellent druggability and safety provide a solid foundation for clinical translation. In the future, research on its pharmacokinetics and in vivo efficacy should be strengthened, combined with modern medicinal chemistry and molecular biology techniques, to promote the clinical application of rhamnosis limonin and its derivatives, providing new therapeutic strategies for the prevention and treatment of inflammation-related diseases.
Shenshuai
Wenjing
Hedandan
