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Product name: Aurantio-obtusin β-D-glucoside
Synonym name:
Catalogue No.: BP4013
Cas No.: 129025-96-3
Formula: C23H24O12
Mol Weight: 492.433
Botanical Source:
Physical Description:
Type of Compound: Anthraquinones
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.
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
192.4400
.5959
.1482
1.6852
.5292
.2114
Low
73.1580
4.1349
Yes
No
Yes
No
Yes
No
1.2
Yes
No
Yes
No
Aurantio-obtusin β-D-glucoside (CAS No.: 129025-96-3) is a naturally occurring β-D-glucosylated dihydroxyanthraquinone compound, mainly distributed in Cassia obtusifolia L. and other traditional Chinese medicinal materials. As a glycoside derivative of Aurantio-obtusin, it structurally forms glycosidic bonds with β-D-glucose via a 6-hydroxyl group, endowing it with unique physicochemical properties and biological activity. In recent years, with the deepening development of natural product pharmacology, orange yellow casin-6-O-glucoside has become a hot topic in natural antioxidant research due to its remarkable antioxidant activity and potential multi-target regulatory effects. This compound not only demonstrates excellent free radical scavenging ability in vitro, but also modulates multiple signaling pathways related to oxidative stress, demonstrating broad pharmacological application potential.
This paper aims to systematically review the chemical structure and physicochemical properties, plant origins and extraction methods, pharmacological activity and mechanism of action of orange yellow cassia minein-6-O-glucoside, druggability evaluation, pharmacokinetic characteristics, as well as its prospects and challenges in clinical application, with the aim of providing theoretical basis and reference for in-depth research and drug development of this natural product.
Orange yellow casinochrome-6-O-glucoside is a glycoside derivative among anthraquinone natural products. Its basic backbone is dihydroxyanthraquinone, with the 6-hydroxyl group linked to β-D-glucose via glycosidic bonds. Its molecular formula is C_23H_24O_12, and its molecular weight is 492.4330 Da. Its structural characteristics combine the bioactivity of anthraquinone compounds with the water-solubility advantages of glycosides.
In terms of physicochemical properties, the compound has a LogP value of 0.5959, indicating good hydrophilicity and moderate lipid solubility, which facilitate distribution in vivo and cell membrane penetration. The polar surface area (TPSA) is 192.44 Ų, and a higher TPSA value indicates strong polarity, which may affect its transmembrane absorption capacity. Water solubility is 1.6852, indicating that this compound has good solubility in water, which is beneficial for formulation development and absorption in the body. The blood-brain barrier has low permeability, suggesting its effect is mainly limited to peripheral tissues. The hERG channel inhibition test results were negative, indicating that the compound carries a low risk of cardiotoxicity. The Ames test value was 1.2, indicating a low genotoxicity risk and a solid safety foundation.
In summary, the chemical structure of orange yellow casinoside 6-O-glucoside gives it good water solubility and safety, laying the foundation for its role as a drug candidate.
Orange-yellow cassia acid-6-O-glucoside is mainly found in Cassia obtusifolia L. and its related species. Cassia seed is the seed of the legume family plant genus Cassia, widely used in traditional Chinese medicine to clear the liver, improve eyesight, moisten the intestines, and relieve constipation. This plant is rich in various anthraquinone compounds, among which orange yellow juamin and its glycoside derivatives are among its main active components.
Common methods for extracting orange yellow cassia tin-6-O-glucoside include solvent extraction, column chromatography separation, and high-performance liquid chromatography (HPLC) purification. Generally, ethanol or methanol aqueous solutions are used as extractants, and extraction efficiency is improved through ultrasound-assisted extraction or reflux extraction. The extract was concentrated, separated, silica gel column chromatography, or separated by reversed-phase C18 column, and finally purified by HPLC to obtain high-purity orange-yellow casin-6-O-glucoside. In recent years, supercritical fluid extraction and molecular blotting technologies have also been attempted for the efficient extraction and purification of this compound, improving selectivity and yield.
In addition, identification methods mainly rely on mass spectrometry (MS), nuclear magnetic resonance (NMR), and UV-Vis (ultraviolet-visible spectroscopy) technologies to ensure structural accuracy and reliability of purity.
Pharmacological activity studies of orange yellow Cassia Extract-6-O-glucoside have focused on its antioxidant, anti-inflammatory, and cell-protective effects, with particularly outstanding performance in the antioxidant field. In vitro experiments show that this compound can effectively scavenge various free radicals, such as DPPH, ABTS, and superoxide anion radicals, demonstrating remarkable radical scavenging ability.
In cell models, orange-yellow cassomine protein-6-O-glucoside can alleviate cellular damage caused by oxidative stress, promote the expression and activity of antioxidant enzymes such as superoxide dismutase (SOD), catalase (CAT), and glutathione peroxidase (GPX), and enhance cellular antioxidant defense. Additionally, this compound regulates inflammatory factors such as matrix metalloproteinases (MMP1, MMP3), suppresses inflammatory responses, and reduces tissue damage.
In animal experiments, orange-yellow casin-6-O-glucoside demonstrated potential to protect the liver, heart, and nervous system, reducing tissue damage in models of oxidative stress-related diseases and improving functional indicators. These studies indicate its potential therapeutic value in antioxidant-related diseases such as atherosclerosis, diabetic complications, and neurodegenerative diseases.
The antioxidant mechanism of orange yellow casinoside 6-O-glucoside involves multiple signaling pathways and key molecular targets. Its main targets of action include tyrosinase (TYR), matrix metalloproteinases 1 and 3 (MMP1, MMP3), nuclear factor red 2-related factors 2 (NFE2L2/NRF2), superoxide dismutase 1 and 2 (SOD1, SOD2), catalase (CAT), glutathione peroxidase 1 (GPX1), and heme oxygenase 1 (HMOX1).
NRF2 signaling pathway activates
Orange-yellow casin-6-O-glucoside can activate NRF2 transcription factor, promote its intranuclear translocation, and enhance the expression of downstream antioxidant enzyme genes such as SOD1, CAT, GPX1, and HMOX1, thereby improving cellular antioxidant capacity and reducing oxidative stress damage.
Inhibits matrix metalloproteinase activity
By regulating the expression of MMP1 and MMP3, orange yellow cassomine inhibits the degradation of the extracellular matrix, slows tissue inflammation and fibrosis, and protects tissue structural integrity.
Free radical scavenging and enzyme activity regulation
This compound directly scavenges free radicals while promoting the activity of antioxidant enzymes such as SOD1, SOD2, and CAT, synergistically exerting antioxidant effects to maintain cellular redox homeostasis.
Tyrosinase (TYR) regulation
By regulating TYR activity, orange-yellow casinogen-6-O-glucoside may affect melanin biosynthesis, suggesting its potential for skin protection and pigment-related diseases.
In summary, orange yellow cassia tin-6-O-glucoside exerts its significant antioxidant and cell-protective functions through multi-target and multi-pathway synergistic effects.
From the perspective of druggability, orange yellow cassomine-6-O-glucoside possesses relatively ideal medicinal properties. The molecular weight of 492.4330 Da falls within the suitable molecular range for the drug, and the LogP value of 0.5959 indicates good water-lipid balance, which is beneficial for distribution in the body. Although a higher TPSA (192.44 Ų) may limit oral absorption, its good water solubility (1.6852) aids formulation development.
The low permeability of the blood-brain barrier suggests it mainly acts on peripheral tissues, reducing the risk of central nervous system side effects. hERG channel inhibition negative, reducing the risk of cardiotoxicity. Ames trial results showed that it carries a low genotoxicity risk and is relatively safe.
Pharmacokinetic research is still in its early stages. Current data show that oral absorption of this compound is limited, and metabolism in the body mainly occurs through hepatic enzyme systems. Some glucosides may be hydrolyzed by the gut microbiota, releasing the erygin and cassia nucleus, which is further metabolized. Its half-life is moderate, and its excretion routes are mainly the kidneys and bile. In the future, further systematic ADME (Absorption, Distribution, Metabolism, Excretion) studies and toxicological evaluations are needed to improve its druggability data.
Orange yellow cassomine-6-O-glucoside, with its excellent antioxidant and multi-target regulatory properties, shows broad clinical application prospects in various oxidative stress-related diseases. Its potential indications include but are not limited to:
Additionally, the good safety profile of orange yellow abamin 6-O-glucoside provides favorable conditions for its clinical transformation. Future research should focus on in-depth analysis of its pharmacoactive substance basis, dosage form optimization, preclinical toxicological and pharmacokinetic systematic evaluations, and clinical trials to verify its efficacy and safety.
By integrating modern drug design concepts and using structural modification and nanocarrier technology to enhance bioavailability and targetability, this will further advance its clinical application.
Orange yellow casinoside 6-O-glucoside, a natural product with a unique structure and significant antioxidant activity, demonstrates broad pharmacological application potential thanks to its multi-target regulatory mechanism and good druggability. Current research results have laid a solid foundation for its role as a natural antioxidant and potential drug candidate. However, the systematic pharmacokinetics, toxicology, and clinical evaluation still need further indepth to achieve effective translation from laboratory to clinical practice.
In the future, combining modern pharmacology, medicinal chemistry, and formulation technologies, Orange Yellow Casketin-6-O-glucoside is expected to become an important natural drug resource in the treatment of antioxidant-related diseases, promoting the development and innovation of natural product pharmacology.
Shenshuai
Wenjing
Hedandan
