Product name: Macrozamin
Synonym name:
Catalogue No.: BP4206
Cas No.: 6327-93-1
Formula: C₁₃H₂₄N₂O₁₁
Mol Weight: 384.338
Botanical Source: Smilax glabra
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

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 Macrozamin

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

Introduction/Overview

Macrozamin (CAS number: 6327-93-1) is a natural product mainly found in the seeds and leaves of Cycas spp. in the Cycas family of plants. As one of the main components of cycad, daidzein has attracted widespread attention in the fields of pharmacology and natural product chemistry due to its unique chemical structure and diverse biological activities. Although daidzein exhibits certain toxicological risks such as carcinogenicity, mutagenicity, teratogenicity, and neurotoxicity, its potential application value in various biological functions such as anti-inflammatory has aroused the interest of researchers. In recent years, with the deepening of molecular biology and pharmacological mechanism research, there has been a gradual increase in related studies on the targets, signaling pathways, and pharmacological evaluation of Daze Mingsu, providing a theoretical basis for its rational utilization in drug development.

This article aims to systematically review the chemical structure and physicochemical properties, plant sources, and extraction methods of daidzein. Combined with the latest pharmacological activity research, it explores its mechanism of action and related molecular targets, evaluates its pharmacological properties and pharmacokinetic characteristics, and looks forward to its potential and challenges in clinical applications. By comprehensively reviewing existing literature, it is expected to provide scientific basis and reference for the subsequent research and development of daidzein.

Chemical structure and physicochemical properties

The chemical name of Daze Mingsu is (specific chemical name may vary slightly due to differences in literature), with a molecular formula of C17H24N2O9 and a molecular weight of 384.3380. Its structural characteristics are mainly manifested by the combination of a glycoside moiety and a nitrogen-containing heterocyclic structure, endowing it with high polarity and water solubility. The LogP value of Daze Mingsu is -2.2011, indicating its strong hydrophilicity and difficulty in freely diffusing through lipid membranes. Its topological polar surface area (TPSA) is as high as 196.7300 Å ², further confirming its polar molecular characteristics, which have important implications for its biofilm permeability and pharmacokinetic behavior.

The water solubility index is 169.7307, indicating good solubility in aqueous phase, which is beneficial for in vivo distribution and improved bioavailability. The low permeability of the blood-brain barrier suggests its limited ability to penetrate the central nervous system. The hERG channel inhibition experiment showed a negative result, indicating that daidzein has high electrophysiological safety for the heart. The Ames mutagenicity test value is 1.8, indicating that it has certain mutagenic potential and is consistent with its known carcinogenic mutagenic properties.

Structurally, the glycosidic bond connections and nitrogen-containing groups of daidzein provide the basis for its biological activity, especially playing an important role in binding to protein targets and signal transduction regulation. Its complex polar structure also provides diversity for its metabolism and excretion pathways in the body.

Plant sources and extraction methods

Da Ze Ming Su mainly comes from the seeds and leaves of Cycas spp. in the Cycas family of plants. As an ancient gymnosperm, the cycad plant has become an important object of natural product research due to its unique secondary metabolites. The content of daidzein in cycad seeds is relatively high, which is a typical characteristic component of this plant species.

Traditional extraction methods often use organic solvent extraction combined with column chromatography separation technology. Common extraction solvents include methanol, ethanol, and their aqueous solutions, which utilize their polarity characteristics to achieve effective dissolution. The extraction process generally includes the following steps:

1. Sample Pretreatment Dry and crush the seeds or leaves of cycad to increase surface area and promote solvent penetration.
2. leaching Multiple extractions were conducted using 70% -95% ethanol or methanol to extract the majority of polar components.
3. concentrate Remove the solvent by vacuum concentration to obtain the crude extract.
4. Separation and purification Using techniques such as silica gel column chromatography and reverse phase high performance liquid chromatography (RP-HPLC), combined with gradient elution, the separation and purification of puerarin were achieved.
5. appraisal Confirm the structure through methods such as mass spectrometry (MS), nuclear magnetic resonance (NMR), and infrared spectroscopy (IR).

In recent years, the application of ultrasound assisted extraction and microwave-assisted extraction technologies has improved extraction efficiency and purity, reduced solvent usage and time costs. In addition, molecular imprinting technology and immunoaffinity chromatography have also been attempted for highly selective separation of daidzein.

Pharmacological activity research

The pharmacological activity research of daidzein mainly focuses on its biological toxicity and anti-inflammatory effects. Although its carcinogenic, mutagenic, and neurotoxic properties limit its direct medicinal use, its potential value in regulating inflammatory responses has attracted attention from the academic community.

Carcinogenic and mutagenic properties

Numerous in vitro and in vivo experiments have shown that daidzein has significant carcinogenic and mutagenic effects. Its mutagenicity was verified through Ames test, which showed that it can induce gene mutations, leading to cellular malignancy. In animal experiments, Daze Mingsu can induce the occurrence of various tumors, especially in the liver and gastrointestinal system. Its carcinogenic mechanism is closely related to DNA adduct formation, oxidative stress, and abnormal cell cycle regulation.

Neurotoxicity and teratogenicity

Daze Mingsu has certain toxic effects on the nervous system, manifested as neuronal apoptosis, nerve conduction dysfunction, and behavioral abnormalities. Its teratogenic effect is mainly reflected in the embryonic development stage, which may lead to abnormal embryonic development and organ deformities by affecting cell division and differentiation processes.

anti-inflammatory activity

Despite the risk of toxicity, Daze Mingsu has shown certain potential in the field of anti-inflammatory. Studies on in vitro cell models and animal inflammation models have shown that daidzein can significantly inhibit the expression and release of various inflammatory mediators, including IL-6, TNF - α, NOS2, and PTGS2. Its anti-inflammatory effect may be achieved by regulating the inflammatory signaling pathway, reducing inflammation and tissue damage.

In addition, the regulation of TRPV1 and TRPA1 plasma channels by Daze Mingsu suggests its potential role in pain and inflammation transmission. The inhibitory effect on CASP1 (caspase 1) suggests that it may intervene in inflammasome activation and reduce the release of pro-inflammatory cytokines.

In summary, the pharmacological activity of Daze Mingsu exhibits a dual nature, with obvious toxicological risks and certain pharmacological regulatory functions. Further exploration of its application value is needed within the safe dosage range.

Mechanism of action and molecular targets

The biological activity of daidzein is closely related to its regulation of multiple molecular targets, especially in the fields of anti-inflammatory and cellular signaling. The current research mainly focuses on the following key targets and signaling pathways:

Inflammatory related targets

• IL-6 (interleukin-6)As a pro-inflammatory cytokine, IL-6 plays a central role in various inflammatory and immune responses. Da Ze Ming Su can inhibit the expression of IL-6 and alleviate inflammatory reactions.
• TNF (tumor necrosis factor)TNF - α is a key mediator of inflammatory response, and Daze Mingsu reduces the cascade of inflammation by inhibiting the release of TNF - α.
• NOS2 (inducible nitric oxide synthase)NOS2 catalyzes the generation of NO and participates in inflammation and oxidative stress. Daze Mingsu inhibits the expression of NOS2, which helps to reduce oxidative damage.
• PTGS1 and PTGS2 (prostaglandin endoperoxide synthase 1 and 2)PTGS2 (COX-2) is an important enzyme in the inflammatory process, and the inhibitory effect of puerarin on it helps to reduce prostaglandin mediated inflammatory response.

signal transducer activity

• STAT3 (Signal Transduction and Transcription Activation Factor 3)STAT3 plays a crucial role in cell proliferation, apoptosis, and immune regulation. Daze Mingsu affects inflammation and tumor related signaling pathways by regulating the activation state of STAT3.
• NFKB1 (nuclear factor kappa B subunit 1)NF - κ B is a classic inflammatory signaling factor, and puerarin can inhibit the activation of NF - κ B and reduce the transcriptional expression of inflammatory genes.
• CASP1 (caspase 1)CASP1 participates in the activation of inflammasomes and regulates the maturation and release of pro-inflammatory cytokines such as IL-1 β. The inhibitory effect of daidzein on CASP1 helps to control the inflammatory response.

Ion channel target

• TRPV1 (Transient receptor potential vanillic acid receptor 1)and TRPA1 (Transient receptor potential vanillic acid receptor subtype A1)These two ion channels play important roles in pain and inflammation signaling. The regulation of TRPV1 and TRPA1 by Daze Mingsu may affect neuroinflammation and pain perception.

In summary, Daze Mingsu exhibits complex pharmacological mechanisms by synergistically regulating inflammatory responses through multiple targets and pathways. The in-depth analysis of these mechanisms provides a theoretical basis for their secure applications and structural optimization.

Evaluation of drug properties and pharmacokinetics

The pharmacological evaluation of Daze Mingsu covers its physicochemical properties, pharmacokinetic characteristics, and safety indicators, comprehensively assessing its potential as a drug candidate molecule.

Physical and chemical properties and pharmacokinetics

• Molecular weight and polarity The molecular weight is 384.3380, belonging to the medium molecular weight range. High TPSA (196.73 Å ²) and negative LogP (-2.2011) suggest strong hydrophilicity and poor lipid solubility, which may limit oral absorption and cell membrane permeability.
• Water solubility Good water solubility (169.7307), beneficial for internal distribution and blood circulation.
• Blood-brain barrier permeability Low, indicating that it is difficult to enter the central nervous system, reducing the risk of central nervous system toxicity, but limiting the therapeutic potential for central targets.
• HERG inhibition No significant inhibitory effect, indicating a low risk of cardiac toxicity.
• Ames test 1.8, showing certain mutagenic potential, safety needs to be carefully evaluated.

Pharmacokinetic characteristics

At present, research on the in vivo absorption, distribution, metabolism, and excretion (ADME) of daidzein is relatively limited. Its high polarity and low fat solubility may lead to lower oral bioavailability, and the metabolic pathways may be mainly liver hydrolysis and glycosidase mediated degradation. The excretion pathway may be mainly through renal excretion, which needs to be further validated through in vivo pharmacokinetic experiments.

safety evaluation

The carcinogenic, mutagenic, and neurotoxic properties of daidzein are the main limiting factors for its medicinal properties. Although its hERG channel has no inhibitory effect and reduces the risk of cardiac toxicity, its mutagenicity and teratogenicity need to be controlled through rigorous toxicological evaluation and dose optimization. In addition, structural modification and derivative design may be effective strategies to reduce toxicity and enhance safety.

Clinical application prospects and prospects

Given the multi-target anti-inflammatory activity of Daze Mingsu, its potential application value in inflammation related diseases cannot be ignored. Inflammation, as the core pathological process of various chronic diseases such as rheumatoid arthritis, inflammatory bowel disease, neuroinflammation, etc., provides a broad space for the action of daidzein.

However, its significant toxicological risks limit its direct application as a clinical drug. Future research directions can focus on:

1. Structural modification and derivative development Reduce toxicity, improve selectivity and pharmacokinetic performance through molecular modification, and develop safe and effective analogues.
2. Targeted delivery system Using nanocarriers, liposomes and other technologies to achieve targeted delivery, reducing systemic toxicity and enhancing local efficacy.
3. Combination therapy strategy Combined use with other anti-inflammatory drugs or natural products to achieve synergistic effects, reduce single drug doses, and minimize adverse reactions.
4. In depth study of mechanisms Further analyze its molecular mechanism of action and signaling pathways, and discover new therapeutic targets and biomarkers.
5. Safety assessment and dose optimization Through systematic toxicology research, clarify the safe dose range and long-term application risks.

In summary, as a natural product with potential pharmacological activity, Daze Mingsu faces safety challenges, but through modern drug development techniques and strategies, it is expected to achieve clinical translation.

Conclusion

As an important active ingredient in cycad plants, daidzein has complex biological activities and significant toxicological risks. Its unique chemical structure endows it with multi-target anti-inflammatory effects, but at the same time, it also brings safety hazards such as carcinogenesis, mutagenesis, and neurotoxicity. Through a systematic review of its chemical properties, pharmacological activity, and mechanism of action, this article reveals the potential value and pharmacological limitations of daidzein in inflammation regulation.

Future research should focus on structural optimization, safety improvement, and precise targeted delivery to maximize its medicinal value. The study of daidzein not only enriches the theoretical system of natural product pharmacology, but also provides valuable natural molecular templates for the development of new anti-inflammatory drugs. With the advancement of scientific research technology and the strengthening of interdisciplinary cooperation, Osamu Daze is expected to play a more important role in the field of natural medicine.