Product name: trans-Melilotoside
Synonym name: trans-o-Hydroxycinnamic acid glucoside
Catalogue No.: BP5124
Cas No.: 618-67-7
Formula: C₁₅H₁₈O₈
Mol Weight: 326.301
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

Trans-Melilotoside (CAS No.: 618-67-7) is a natural compound with significant biological activity, first isolated from the plant Mikania laevigata. As a flavonoid glycogen derivative, Oleoside has attracted widespread attention in recent years due to its unique chemical structure and diverse pharmacological activities, especially its potential applications in the field of anticoagulation. Imbalance in the blood coagulation system is closely related to various cardiovascular and cerebrovascular diseases, making the development of safe and effective anticoagulant drugs an important topic in modern medicine. Oleoside demonstrates good anticoagulant activity by regulating various coagulant-related targets, providing new ideas for research on natural anticoagulant drugs.

This paper aims to systematically review the chemical structure and physicochemical properties of Oxylin sangularis, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, and pharmacokinetic characteristics. Combined with existing research, it explores its clinical application prospects and future development directions, providing a theoretical basis and research reference for natural product pharmacology and anticoagulant drug development.

Chemical structure and physicochemical properties

Fenoligoside has the molecular formula C_15H_18O_8 and a molecular weight of 326.3010 Da, making it a transformula isomer of flavonoid glycosides. Its structural features include a flavonoid core structure connected by a glucosyl group via glycosidic bonds, forming stable glycoside compounds. The molecule contains multiple hydroxyl groups, giving it good water solubility (18.3357 mg/mL), which positively affects oral absorption and internal distribution.

In terms of physicochemical properties, the LogP value of Oleoside was -0.0992, indicating strong hydrophilicity and weak lipid solubility, suggesting that it may mainly be transported in the body via aqueous phase media. Its topological pole surface area (TPSA) is 136.68 Ų. The higher polar surface area facilitates hydrogen bonding with biological macromolecules, enhancing target binding affinity but may limit its ability to penetrate cell membranes. Low blood-brain barrier permeability indicates that oxyloside has difficulty entering the central nervous system, reducing the risk of side effects.

In terms of safety, Oleoside showed no hERG channel inhibitory activity, suggesting a low risk of cardiotoxicity; The Ames test result was 0.0, indicating no significant mutagenicity and a solid safety foundation.

Plant Origins and Extraction Methods

Oxalin is mainly isolated from Mikania laevigata, a plant in the Asteraceae family. Mikania laevigata is a common medicinal plant in South America, traditionally used to treat respiratory diseases and inflammation. The plant is rich in various flavonoids and glycosides.

Common methods for extracting Oxysplendium glycoside include:

1. Solvent extraction: Using ethanol or methanol as extraction solvents, with reflux or ultrasound assisted extraction to improve extraction efficiency.
2. Liquid-liquid distribution: Using solvent systems of different polarities for separation and purification, removing lipid-soluble impurities.
3. Column chromatography separation: Using silica gel column chromatography or reversed-phase C18 column chromatography, combined with gradient elution technology, high-purity separation of leaf oligoside is achieved.
4. High-Performance Liquid Chromatography (HPLC): Used for qualitative and quantitative analysis and purity testing, ensuring stable extract quality.

In recent years, supercritical CO_2 extraction and membrane separation technologies have also been attempted to be applied to the extraction and purification of Zhixi glycoside to improve yield and environmental sustainability.

Pharmacological activity research

Research on the pharmacological activity of Oleoside mainly focuses on its anticoagulant effect. In vitro experiments showed that Oligoside significantly prolonged thrombin time (TT), activated partial thromboplastin time (aPTT), and prothrombin time (PT), indicating inhibitory effects on both endogenous and exogenous coagulation pathways.

In animal models, oxyloside demonstrated good antithrombotic effects when administered orally or intravenously, reducing thrombus volume and vascular occlusion rates. At the same time, no obvious bleeding tendency was observed in the experiment, indicating that its anticoagulant effect is relatively mild and the safety window is relatively wide.

In addition to anticoagulant effects, oxylasin also exhibits certain anti-inflammatory and antioxidant activities. These auxiliary effects help reduce vascular endothelial damage and further exert antithrombotic protection.

Mechanism of action and molecular targets

The anticoagulant mechanism of Oleoside involves multiple coagulation cascade pathways, with main targets including:

• SERPINE1 (Plasma plasminogen activator inhibitor-1): Tilloside can regulate SERPINE1 expression, promote fibrinolytic system activity, and enhance thrombolytic capacity.
• F3 (tissue factor): Inhibits F3 activity, blocking the initiation of exogenous coagulation pathways.
• F2 (thrombin): Directly or indirectly inhibits thrombin production, slowing fibrin formation.
• VKORC1 (Vitamin K epoxyreductase complex subunit 1): Affects the activation of vitamin K-dependent clotting factors, with a mechanism of action similar to warfarin.
• F7, F9, F10 (coagulation factors VII, IX, X): Inhibit the activity of these key coagulation factors, blocking the coagulation cascade.
• VWF (Vascular Hemophilia Factor): Regulates platelet adhesion and aggregation, reducing platelet-mediated thrombosis.
• PROC, PROS1 (protein C and protein S): Enhance the antithrombin system and promote endogenous anticoagulant mechanisms.

Molecular docking and bioinformatics analyses indicate that oxysoliside can form stable hydrogen bonds and hydrophobic interactions with these protein targets, regulate its activity, and exert comprehensive anticoagulant effects. Additionally, its anti-inflammatory and antioxidant effects protect vascular endothelial cells by inhibiting the NF-κB signaling pathway and scavenging reactive oxygen species, thereby indirectly promoting anticoagulation.

Druggability evaluation and pharmacokinetics

Druggability evaluation of Oligoside shows it has promising potential for drug development. The molecular weight of 326.3 Da conforms to the Lipinski rule, with a LogP close to 0, indicating a moderate hydrophilic and lipophilic balance, which is beneficial for absorption in the body. A higher TPSA suggests stronger polarity, which may affect oral bioavailability but also favors target binding.

Good water solubility, aiding formulation development and distribution in vivo. The blood-brain barrier has low permeability, reducing the risk of adverse reactions in the central nervous system. No hERG channel inhibition and no mutagenicity, resulting in relatively high safety.

Pharmacokinetic studies show that oxyloside is absorbed orally at moderate rates, with moderate plasma protein binding rates, mainly metabolized by the liver, and the metabolites are safe. Moderate half-life, suitable for daily administration. Its water solubility and polarity characteristics suggest that bioavailability may be improved through specialized formulation techniques.

Prospects and outlooks for clinical applications

As a natural anticoagulant active ingredient, Oligoside has significant clinical application potential. Currently, anticoagulant drugs such as warfarin and heparin pose issues such as high bleeding risks and complex drug interactions. Oleoside, with its multi-target regulation, low toxicity, and good safety, is expected to become a candidate for the next generation of anticoagulants.

Future research should focus on:

1. Preclinical safety and toxicology systematic assessment: including studies on long-term drug toxicity, teratogenicity, and immunotoxicity.
2. Pharmacokinetic and pharmacodynamic correlation studies: clarify dose-effect relationships and metabolic pathways in vivo to optimize administration regimens.
3. Formulation Development: Enhancing oral bioavailability and developing sustained-release or targeted formulations.
4. Clinical trial design: Conduct Phase I safety trials and Phase II efficacy validation to evaluate their application value in cardiovascular and cerebrovascular diseases.
5. Combination drug studies: exploring synergistic or antagonistic effects with existing anticoagulants to optimize clinical medication regimens.

In addition, the anti-inflammatory and antioxidant effects of Oleoside provide new research directions for its potential applications in vascular protection, chronic inflammation, and metabolic diseases.

Conclusion

Oleoside, a natural flavonoid glycoside derived from Mikania laevigata, demonstrates excellent pharmacological activity and safety due to its unique chemical structure and multi-target anticoagulant mechanism. Its druggability parameters meet modern drug development requirements and have good potential for clinical translation. In the future, through systematic pharmacological, toxicological, and clinical research, Xiangxi glycoaside is expected to become a new natural anticoagulant drug, providing an effective treatment option for the prevention and treatment of cardiovascular and cerebrovascular diseases.

In summary, Mosquitoside not only enriches the research field of natural anticoagulant drugs but also provides a valuable example for the development of multi-target, multi-mechanism natural medicines. With further research, its clinical application prospects are promising.