Product name: Calycanthoside
Synonym name: Isofraxidin 7-O-beta-D-glucoside
Catalogue No.: SBP01731
Cas No.: 483-91-0
Formula: C17H20O10
Mol Weight: 384.337
Botanical Source:
Physical Description: Powder
Type of Compound: Coumarins
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:
Isofraxidin-7-O-glucoside(Calycanthoside ) has the anti-inflammatory effect, it has inhibitory activity on NO production.It also shows antibacterial activity.
References:
China Medical Herald, 2016, 13(13):20-3.
Anti-inflammatory constituents of Acanthopanax senticosus
To study the anti-inflammatory constituents of Acanthopanax senticosus.
METHODS AND RESULTS:
NO production in the activated RAW 264.7 macrophages induced by LPS and IFN-γ were used to evaluate anti-inflammatory activity. The compounds were isolated by HPD 100 resin, silica gel, ODS and HPLC methods, their structures were identified by Infrared TLC method and spectral imaging spectrum technology. The extraction of A. senticosus. had inhibitory activity on NO production. Seven compounds were isolated and identified as Syringin, Isofraxidin-7-O-glucoside(Calycanthoside),, Syringaresinoldi-O-β-D-glycoside, Sesamin, Daucosterol, β-sitosterol and Vanillic acid respectively.
CONCLUSIONS:
The extraction of A. senticosus. has the anti-inflammatory effect, and phenylpropanoids are the anti-inflammatory constituents.
Zhongguo Zhong Yao Za Zhi,2008,33(15):1843-6.
Studies on chemical constituents and antibacterial activity from n-butanol extract of Sarcandra glabra
To study the chemical constituents and the antibacterial activity from n-butanol extract of Sarcandra glabra.
METHODS AND RESULTS:
The compounds were isolated by Diaion HP-20, Sephadex LH-20, MCI CHP-20 and silica gel column chromatographic methods. Their structures were identified on the basis of physicochemical and spectroscopic analysis. The antibacterial effect of the compounds were measured against Staphylococcus aureus by filterpaper slice method, finally the antibacterial ring in each group was recorded after 24 hours. Seven constituents were isolated and elucidated as 5, 7, 3', 4'-tetrahydroxy-6-C-beta-D-glucopyranosylflavanone(1),kaempferol-3-O-beta-D-glucuronide (2),fraxidin (3),isofraxidin (4),isofraxidin-7-O-beta-D-glucopyranoside(Calycanthoside) (5),kaempferol (6), pinostrobin (7).
CONCLUSIONS:
Diameters (in mm) of antibacterial ring in the compounds 2, 5, 6 were orderly recorded as follows: 14.67 +/- 0.08, 11.14 +/- 1.06, 8.26 +/- 1.26 and the compound 4 is not effective. Compounds 1-3 and 5 were isolated from S. glabra for the first time.
HPLC of Calycanthoside
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
Calycanthoside (CAS No. 483-91-0) is a natural compound isolated from the traditional Chinese medicinal herb Angelica tenuissima, belonging to the isolazine pedrin glycoside compound. With the development of modern pharmacology and natural product chemistry, isozine-7-glucoside has gradually attracted widespread attention due to its remarkable bioactivity, especially its potential in anti-inflammatory fields. As the fundamental pathological process of the occurrence and development of various diseases, inflammatory reactions have complex and diverse regulatory mechanisms. Finding highly efficient and low-toxicity anti-inflammatory natural products has become an important direction for current drug development. This paper will systematically review the chemical structure and physicochemical properties of isozine-7-glucoside, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, and pharmacokinetic characteristics. Finally, it discusses its clinical application prospects and future research directions, providing reference and inspiration for researchers in related fields.
The molecular formula of isozine-7-glucoside is C_18H_24O_10, with a molecular weight of 384.3370. Its structural core is the isozine-peridine ring, with the 7-position hydroxyl group connected to the glucose unit via glycosidic bonds. The compound has a LogP value of -0.2177, indicating strong hydrophilicity, with a water solubility of 9.3360, indicating good water solubility. The polar surface area (TPSA) is 148.0500, indicating that its molecular polarity is relatively high, which may affect membrane permeability and bioavailability. The blood-brain barrier has low permeability, suggesting limited distribution in the central nervous system. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames trial scored 0.9, indicating low genotoxic potential and a solid safety foundation.
Chemically, the glycosides of isozine-7-glucoside endow it with good water solubility and biocompatibility, while the core of isozine-piridine may be the key to its bioactivity. This structural feature gives it certain advantages in drug design, especially suitable for developing oral anti-inflammatory drugs.
Isozine-7-glucoside is mainly isolated from Angelica tenuissima, a plant in the Apiaceae family. Angelica plants are widely used in traditional Chinese medicine, possessing multiple effects such as harmonizing qi and blood, promoting blood circulation and removing blood stasis, dispelling wind and dampness. Angelica tenuissima, as one of the important medicinal species, contains abundant isozine-deridine compounds in its rhizomes.
The extraction method typically uses ethanol or methanol as solvent for reflux extraction, followed by multi-step separation and purification techniques such as liquid-liquid separation, silica gel column chromatography, and reversed-phase high-performance liquid chromatography (RP-HPLC) to obtain high-purity isozidine-7-glucoside. In recent years, the application of ultrasound-assisted extraction and microwave-assisted extraction technologies has significantly improved extraction efficiency and purity, while reducing solvent usage and extraction time. In addition, the application of reversed-phase solid-phase extraction (SPE) combined with high-performance liquid chromatography-mass spectrometry (HPLC-MS) technology has promoted qualitative and quantitative analysis of this compound, providing a reliable analytical method for subsequent pharmacological studies.
The main pharmacological activity of isozine-7-glucoside is concentrated in its anti-inflammatory effect. A large number of in vitro cell models and in vivo animal experiments have shown that this compound can effectively inhibit the production and release of various inflammatory mediators, reducing inflammatory responses.
At the cellular level, isozin-7-glucoside significantly inhibits the expression of pro-inflammatory factors such as IL-6, TNF-α, NOS2, and PTGS2 in macrophages and monocyte cell lines, reducing activation of inflammatory signaling pathways. Its regulatory effect on the NFKB1 and STAT3 signaling pathways is particularly prominent, able to block the transmission of inflammatory signals and reduce cellular inflammatory responses. Additionally, the compound's regulatory effect on the TRPV1 and TRPA1 plasma channels suggests potential value in neuroinflammation and pain relief.
In animal experiments, isozine-7-glucoside demonstrated good anti-inflammatory effects across various inflammation models (such as acute inflammation, chronic inflammation, and inflammatory pain models), significantly reducing tissue swelling, inflammatory cell infiltration, and related pathological damage. Its anti-inflammatory effect is positively correlated with dosage and has no significant toxic side effects.
In addition, isozine-7-glucoside also shows certain antioxidant activity, which can scavenge free radicals, reduce oxidative stress, and further support its anti-inflammatory effects.
The anti-inflammatory mechanism of isozine-7-glucoside involves multiple molecular targets and signaling pathways, reflecting its multi-target and multi-pathway coordinated regulation.
IL-6 and STAT3 signaling pathways
IL-6, as a key pro-inflammatory cytokine, activates the STAT3 signaling pathway, promoting the persistence and intensification of inflammatory responses. Isozine-7-glucoside can inhibit IL-6 expression and mediated STAT3 phosphorylation, blocking transcription of downstream inflammatory genes to achieve anti-inflammatory effects.
NFKB1 signaling pathway
NFKB1 is a central regulatory factor in inflammatory responses, regulating the expression of various inflammatory mediators. Isazine-7-glucoside alleviates inflammatory responses by inhibiting NFKB1 activation and reducing the expression of pro-inflammatory genes.
CASP1 (caspase 1)
CASP1 is involved in the assembly of inflammasomes and the activation of the inflammatory factor IL-1β, promoting inflammatory cascade responses. Isozine-7-glucoside inhibits CASP1 activity and blocks inflammatory signaling mediated by inflammasomes.
TRPV1 and TRPA1 ion channels
These two channels play important roles in inflammatory pain and neuroinflammation. Isozine-7-glucoside regulates the activity of TRPV1 and TRPA1, relieving inflammation-related pain symptoms.
PTGS1 and PTGS2 (cyclooxygenases 1 and 2)
PTGS2 is a key enzyme that induces expression during inflammatory processes and catalyzes the synthesis of prostaglandins. Isazine-7-glucoside inhibits PTGS2, helping to reduce the generation of inflammatory mediators.
NOS2 (Induced nitric oxide synthase)
NOS2 produces large amounts of nitric oxide during inflammatory responses, promoting inflammation progression. Isazine-7-glucoside inhibits NOS2 expression, reducing oxidative stress and inflammatory damage.
In summary, isozine-7-glucoside regulates inflammation-related signaling pathways through multi-target synergistic effects, exerting systemic anti-inflammatory effects.
From the perspective of druggability, isozine-7-glucoside has relatively ideal physicochemical properties. It has a moderate molecular weight (384.3 Da) and a LogP value of -0.2177, showing good water solubility and moderate lipid solubility, which is beneficial for absorption and distribution in the body. A higher TPSA (148.05 Ų) suggests strong polarity, which may limit membrane permeability but also facilitates dissolution and transport in the blood.
Low blood-brain barrier permeability indicates that the compound mainly acts on peripheral tissues, reducing the potential risk of toxicity in the central nervous system. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity and good safety. The Ames test results were nearly negative, indicating a low risk of genotoxicity.
Currently, pharmacokinetic research on isozine-7-glucoside is relatively limited. Preliminary data suggest its oral bioavailability is limited, possibly due to its high polarity and glycoside structure. In vivo, metabolism mainly involves glycoside hydrolysis and oxidation through the hepatic enzyme system; the activity and safety of these metabolites require further research. The excretory route is mainly through the kidneys.
In the future, it is necessary to strengthen systematic research on its absorption, distribution, metabolism, and excretion (ADME) characteristics, optimize administration routes and formulation design, and improve its clinical feasibility.
As a natural product with significant anti-inflammatory activity, isozine-7-glucoside has broad clinical application potential. Inflammation-related diseases such as rheumatoid arthritis, inflammatory bowel disease, and chronic obstructive pulmonary disease all have urgent treatment needs, while existing drugs often come with side effects and resistance issues. Isozine-7-glucosides, with their multi-target regulatory mechanisms and good safety profile, provide a valuable molecular basis for the development of novel anti-inflammatory drugs.
Additionally, its regulatory effects on TRPV1 and TRPA1 channels suggest potential application value in neuroinflammation and pain management. In the future, modern drug delivery technologies, such as nanocarriers and sustained-release formulations, can be combined to enhance bioavailability and targeting.
In terms of clinical translation, systematic toxicological evaluation, pharmacokinetic studies, and preclinical efficacy validation are needed, gradually advancing to the clinical trial stage. Combining modern molecular biology techniques to deeply analyze their mechanisms of action and metabolic pathways will help guide the formulation of clinical medication regimens.
In addition, structural modification and derivative development of isozine-7-glucoside are also key research priorities for future research. By optimizing its structure, its efficacy and pharmacokinetic performance are improved, promoting it as a new generation of safe and efficient anti-inflammatory drugs.
As an important active ingredient in Angelica tenuissima, isozine-7-glucoside shows great potential as a natural anti-inflammatory drug due to its unique chemical structure and significant anti-inflammatory activity. Its multi-target regulatory mechanism of inflammatory signaling pathways offers new ideas for treating various inflammation-related diseases. Although there are still certain challenges in pharmacokinetics and clinical applications, with deeper research and technological advancements, isozine-7-glucoside is expected to become a star compound in the field of natural product pharmacology, propelling anti-inflammatory drug development to new heights. Future research should focus on mechanistic analysis, drug optimization, and clinical translation, promoting its widespread application in modern medicine.
