Product name: Phaseoloidin
Synonym name:
Catalogue No.: BP4223
Cas No.: 118555-82-1
Formula: C₁₄H₁₈O₉
Mol Weight: 330.289
Botanical Source:
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.

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

Introduction/Overview

Phaseoloidin (CAS No.: 118555-82-1) is a natural product derived from plants that has attracted attention in recent years due to its multi-target pharmacological activity. As an orally active compound, Butengziside demonstrates unique biological functions in multiple fields including inflammation regulation, enhancement of autophagy, resistance to insect herbivory defense, and antiparasitic effects. It can effectively inhibit the activation of NLRP3 inflammasomes, block the caspase-11-GSDMD-mediated pyroptosis pathway, and maintain cartilage matrix integrity by regulating collagen-degrading enzyme expression, showing potential therapeutic value in models of acute gouty arthritis and pulmonary fibrosis. Additionally, Tengziside enhances cellular autophagy by activating the AMPK/mTOR signaling pathway, further revealing its multiple mechanisms of action. It inhibits the growth and development of Lepidoptera herbivorous insects Manduca sexta and Spodoptera littoralis larvae, reflecting its ecological significance in plant defense. This paper will systematically review the chemical structure, plant origin, pharmacological activity, mechanism of action, druggability evaluation, and clinical application prospects of Ketengzi Glycoside, aiming to provide a theoretical foundation and reference for in-depth research and drug development of this natural product.

Chemical structure and physicochemical properties

The molecular formula of Ketengzi Side is C_17H_18O_7, with a molecular weight of 330.2890 Da. Its structural features include multiple hydroxyl and glycosidic groups, giving it high polarity and water solubility. The calculated LogP value was -1.0070, indicating low hydrophobicity and strong hydrophilicity, which is beneficial for oral absorption and internal distribution. The polar surface area (TPSA) is 156.9100 Ų, indicating high polarity that may affect its ability to pass through cell membranes, but also aids in binding to polar targets. Water solubility is 28.7555 mg/mL, indicating good solubility in the aqueous phase, which is beneficial for formulation development. The low permeability of the blood-brain barrier (BBB) suggests its limited distribution in the central nervous system, which may reduce the risk of central side effects. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames-induced mutagenic test result was 0.0, indicating a low genotoxicity risk and good safety potential.

The chemical structure of Ketaneoside contains a typical flavonoid backbone linked to glycosides, offering good structural stability and suitable for chemical modification to optimize pharmacodynamics and pharmacokinetic properties. The presence of hydroxyl groups makes it possible to form hydrogen bonds, aiding in binding to biological macromolecule targets.

Plant Origins and Extraction Methods

Phaseolus spp. is mainly found in plants of the genus Phaseolus (Phaseolus spp.), especially in the seeds and roots of legumes such as Phaseolus vulgaris. These plants are widely distributed in tropical and subtropical regions and have significant economic and medicinal value. The extraction of pentanine usually uses traditional solvent extraction methods, combined with ultrasound-assisted or microwave-assisted technologies to improve extraction efficiency.

Common extraction processes include: first, plant materials are dried and crushed, then methanol or ethanol is used as extraction solvents for extraction extraction; Subsequently, coarse separation and purification are performed through liquid-liquid distribution and column chromatography (such as silica gel columns and C18 reversed-phase columns); Finally, purity improvement is further achieved using high-performance liquid chromatography (HPLC) or preparative HPLC. In recent years, supercritical CO_2 extraction and membrane separation technologies have also been attempted to extract glutin, aiming to achieve green environmental protection and efficient separation.

During extraction, attention must be paid to controlling solvent polarity and temperature to prevent structural degradation of glucoside. Purified tengzi glycoside can be identified structurally by mass spectrometry (MS), nuclear magnetic resonance (NMR), and other methods to ensure its chemical purity and structural integrity.

Pharmacological activity research

Anti-inflammatory and immunomodulatory effects

Ketengzi glycoside has been studied in the field of anti-inflammatory research, especially in regulating NLRP3 inflammasome activation. NLRP3 inflammasomes are important drivers of various inflammatory diseases, and their excessive activation can lead to pyroptosis and the release of pro-inflammatory factors. Ketengzi glycoside can effectively inhibit the assembly and activation of NLRP3 inflammasomes, block the caspase-11-GSDMD-mediated pyroptosis pathway, reduce the release of pro-inflammatory cytokines, and thus alleviate inflammatory responses.

Additionally, Tengziside protects the integrity of cartilage matrix by reducing the expression of collagen-degrading enzymes (such as MMPs), showing potential therapeutic effects on arthritis, especially acute gouty arthritis. Relevant in vivo and in vitro experiments have shown that Phytosinoside can significantly alleviate arthritis symptoms, inhibit cartilage destruction, and improve joint function.

Autophagy regulation

Autophagy, as an important intracellular metabolic and quality control mechanism, plays a key role in maintaining cellular homeostasis and responding to pathological stimuli. Butengziside can activate the AMPK/mTOR signaling pathway, promoting the initiation and progression of autophagy. By enhancing autophagy, pegin helps clear damaged components and inflammatory mediators within cells, exerting a protective effect on cells.

This mechanism is particularly evident in pulmonary fibrosis models, where Tengziside promotes autophagy activity in lung tissue cells and slows fibrotic progression, suggesting its potential in treating lung diseases.

Insect resistance and herbivorous defense

Pentinoside has a significant inhibitory effect on the growth and development of Lepidoptera larvae such as Manduca sexta and Spodoptera littoralis. This compound enhances the plant Nicotiana attenuata's defense against herbivorous insects by interfering with insect metabolism and development, inhibiting larval growth and survival rates. This ecological function not only reflects the natural defensive role of gutanzi glycoside, but also provides a theoretical basis for the development of new biopesticides.

Antimalarial activity

Although the antimalarial effects of ketanine are still in the preliminary research stage, their potential inhibitory effects on malaria parasite-related targets (such as PFCRT, PFMDR1, PFDHFR, PFK13, etc.) have been reported. Through multi-target action, ketengzi glycoside may interfere with the metabolism and drug tolerance mechanisms of malaria parasites, demonstrating potential for the development of novel antimalarial drugs.

Mechanism of action and molecular targets

The multi-target mechanism of Tengziside is the basis of its pharmacological diversity. The main aspects involved are as follows:

1. NLRP3 inflammasome inhibition: Butengziside acts directly or indirectly on the NLRP3 protein complex, blocking its assembly and activation, reducing caspase-1 activation and the release of pro-inflammatory cytokines such as IL-1β and IL-18, thereby alleviating inflammatory responses.

2. Block of caspase-11-GSDMD cell pyrroptosis: Butengzidin inhibits caspase-11 activation, prevents the cleavage and pore formation of Gasdermin D (GSDMD), blocks pyroptosis, and protects tissue cells from inflammatory damage.

3. Regulation of collagen-degrading enzyme expression: By downregulating matrix metalloproteinases (MMPs) and other collagen-degrading enzymes, pentaneoside maintains structural stability of cartilage matrix and delays degenerative joint disease.

4. AMPK/mTOR signaling pathway activation: Phytosinoside activates the energy-sensitive kinase AMPK, inhibits mTOR signaling, promotes autophagy, enhances the cell's ability to clear damaged components, and improves cell function.

5. Inhibition of insect growth and development: Tengzi glycoside may inhibit larval growth and development by interfering with insect endocrine regulation and energy metabolism; the specific molecular mechanism requires further elucidation.

6. Malaria-related target interventions: Phytosinoside has potential binding and inhibitory effects on membrane transporters (PFCRT, PFMDR1), enzymes (PFDHFR), and other key metabolic proteins, possibly inhibiting parasite growth through multi-target synergistic effects.

Druggability evaluation and pharmacokinetics

Ketengziside shows good potential in terms of druggability. It has a moderate molecular weight and good water solubility, which is beneficial for the development of oral formulations. Lower LogP values and high TPSA suggest greater polarity, which may affect its ability to cross lipid membranes, but this is partially overcome by its oral activity. Low blood-brain barrier permeability reduces the risk of central nervous system side effects.

In terms of safety, tengzi glycoside does not inhibit the hERG channel, reducing the risk of cardiotoxicity; A negative Ames test indicates a low genotoxicity risk and relatively high safety.

Currently, pharmacokinetic research on Butengziside is limited. Preliminary data show good oral absorption, but key parameters such as metabolic pathways, half-life, and bioavailability still require systematic study. In the future, in vivo pharmacokinetic and toxicological assessments should be strengthened to guide preclinical research and formulation optimization.

Prospects and outlooks for clinical applications

As a multi-target natural product, Tengziside has broad clinical application potential. Its therapeutic efficacy in inflammatory diseases such as acute gouty arthritis and pulmonary fibrosis provides important directions for clinical development. By regulating inflammatory bodies and autophagy pathways, Tengziside is expected to become a novel anti-inflammatory drug that fills the gaps of existing treatment methods.

Moreover, the role of glutin in plant defense and insect resistance provides natural candidate molecules for agricultural biocontrol, promising development as an environmentally friendly biopesticide that reduces the use of chemical pesticides.

Although its antimalarial activity is still in the early research stage, its multi-target mechanism of action provides a theoretical basis for developing novel antimalarial drugs, especially when facing the challenge of drug-resistant malaria, where betanoside and its derivatives have potential application value.

Future research should focus on pharmacokinetic optimization, formulation development, and preclinical safety evaluation of tengzi glycoside, while also deeply analyzing its molecular mechanisms and exploring structural modifications to enhance activity and selectivity. Multidisciplinary collaboration will drive Tengzi Glycoside from the laboratory to clinical applications.

Conclusion

As a natural product with multi-target regulatory capabilities, Ketengzi Side demonstrates rich pharmacological activity and promising drug potential. Its research achievements in anti-inflammation, autophagy regulation, insect resistance, and antiparasitic areas provide valuable resources for natural product pharmacology and new drug development. Although current research on its pharmacokinetics and clinical applications is insufficient, its unique mechanism of action and safety advantages make it an important candidate for future drug development. Through ongoing basic research and translational medical efforts, Tengziside is expected to become a novel drug for treating inflammatory diseases and antiparasitic infections, contributing new strength to human health.