Product name: Scheffoleoside A
Synonym name:
Catalogue No.: BP5038
Cas No.: 160669-23-8
Formula: C₄₈H₇₈O₁₉
Mol Weight: 959.133
Botanical Source:
Type of Compound: Triterpenoids

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

Centella asiatica-28-O-rhamnose (1-4) glucose (1-6) glucoside (Scheffoleoside A) is derived from the traditional Chinese medicinal plant centella asiatica) and belongs to the triterpene saponin class of compounds. Centella asiatica, a medicinal plant widely used in traditional Asian medicine, has attracted much attention for its significant effects in promoting wound healing, anti-inflammatory, antioxidant, and neuroprotective effects. Scheffoleoside A, as one of the important active ingredients in Centella asiatica, has shown potential pharmacological value in recent years in neuroprotection and skin repair. This paper aims to systematically review the chemical structure and physicochemical properties, plant origin and extraction methods, pharmacological activity, mechanism of action, druggability evaluation, and clinical application prospects of Scheffoleoside A, aiming to provide a theoretical basis and reference for subsequent related research and new drug development.

Chemical structure and physicochemical properties

The chemical name of Scheffoleoside A is Centella Asiatic-28-O-rhamnose (1-4)Glucoside (1-6)glucoside, molecular formula C_48H_76O_19, molecular weight 959.1330. Its core structure is a triterpene backbone of asiatic acid, with a 28-position carboxyl group linked by glycosidic bonds to a trisaccharide chain composed of rhamnose and two glucose molecules. The trisaccharide chain is connected by rhamnose (1→4) glucose (1→6) glucose, forming a relatively complex glycoside structure.

In terms of physicochemical properties, Scheffoleoside A has a LogP value of about 1.92, indicating moderate hydrophobicity, which facilitates cell membrane penetration but has limited water solubility. Its topological polar surface area (TPSA) reaches as high as 315.21 Ų, indicating strong molecular polarity that may limit its ability to cross the blood-brain barrier. Its water solubility is 0.1882, making it a low-solubility compound. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity; Ames-induced mutagenic test results were zero, indicating no significant genotoxicity risk. In summary, Scheffoleoside A demonstrates good safety and certain bioactivity potential in terms of physicochemical properties, but its high polarity and molecular weight pose challenges to the drug's bioavailability.

Plant Origins and Extraction Methods

Scheffoleoside A is mainly found on the leaves and stems of centella asiatica. Centella asiatica is a perennial herbaceous plant in the Apiaceae family, widely distributed in tropical and subtropical Asia. It has a long medicinal history and has traditionally been used to treat skin wounds, scars, varicose veins, and neurological diseases.

Common methods for extracting Scheffoleoside A include solvent extraction, liquid-liquid partitioning, and column chromatography separation. Ethanol or methanol is generally used as the preliminary extraction solvent, utilizing their good solubility of triterpene saponins. After concentration, the extract was separated and purified using a silica gel column or a C18 reversed phase column with water-ethanol gradient elution. High-performance liquid chromatography (HPLC) and mass spectrometry (MS) technologies are used for purity detection and structural confirmation. In recent years, ultrasound-assisted extraction and microwave-assisted extraction technologies have also been applied to improve the extraction efficiency and purity of Scheffoleoside A.

Pharmacological activity research

Neuroprotective effects

Research on Scheffoleoside A in the field of neuroprotection is gradually increasing. In vitro experiments show that this compound exhibits moderate inhibitory activity against neuronal cytotoxicity induced by 6-hydroxydopamine (6-OHDA). 6-OHDA is a commonly used Parkinson's disease model toxin that induces oxidative stress and mitochondrial dysfunction, leading to the death of dopaminergic neurons. Scheffoleoside A protects nerve cell survival by reducing cellular oxidative damage and inflammatory responses, demonstrating its potential neuroprotective effects.

Additionally, Scheffoleoside A may enhance its neuroprotective effects by modulating intracellular signaling pathways, inhibiting the expression of apoptosis-related proteins, promoting nerve cell regeneration, and enhancing its neuroprotective effects. Although there is currently limited research related to it in vivo, its application prospects in neurodegenerative diseases warrant in-depth exploration.

Skin repair effects

Centella asiatica and its main components have been widely proven to promote skin repair. Scheffoleoside A, as a glycoside derivative of centella asiaticalate, is involved in regulating various molecular targets related to skin repair, including matrix metalloproteinases (MMP1, MMP2, MMP9), epidermal growth factor receptor (EGFR), fibroblast growth factor 2 (FGF2), transforming growth factor β1 (TGFB1), collagen (COL3A1, COL4A1), vascular endothelial growth factor A (VEGFA) and integrin beta-1 (ITGB1), among others.

These targets play key roles in skin cell proliferation, migration, collagen synthesis, angiogenesis, and inflammation regulation. Scheffoleoside A promotes skin wound healing, suppresses excessive inflammatory responses, and improves skin structural integrity by modulating the expression and activity of these targets. Relevant cell experiments and animal model studies support its potential as a skin repair agent.

Mechanism of action and molecular targets

The pharmacological effects of Scheffoleoside A mainly depend on its interactions with various molecular targets, regulating cellular signaling networks.

1. Matrix metalloproteinases (MMPs) are regulated
   MMP1, MMP2, and MMP9 are key enzymes involved in the degradation of the extracellular matrix (ECM); overactivation leads to collagen degradation, affecting skin structure and function. Scheffoleoside A can regulate MMP expression, inhibit their overactivation, maintain ECM stability, and promote skin repair.

2. Growth factors and their receptors
   EGFR and FGF2 play important roles in cell proliferation and migration. Scheffoleoside A promotes fibroblast proliferation and collagen synthesis by activating the EGFR signaling pathway. Regulation of FGF2 contributes to angiogenesis and tissue regeneration.

3. Transforming Growth Factor β1 (TGFB1)
   TGFB1 is a multifunctional factor regulating cell proliferation, differentiation, and ECM synthesis. The effect of Scheffoleoside A on TGFB1 helps control inflammatory responses and promotes fibrotic responses during wound healing.

4. Collagen and integrin
   COL3A1 and COL4A1 are the main types of skin collagen, with ITGB1 acting as a bridge between the extracellular matrix and cells, participating in cell adhesion and signal transduction. Scheffoleoside A enhances the integrity of skin structure and functional recovery by promoting the expression of these proteins.

5. Antioxidant and anti-inflammatory mechanisms
   In terms of neuroprotection, Scheffoleoside A inhibits oxidative stress-related pathways, reduces reactive oxygen species (ROS) production, lowers apoptosis, and protects neurons from toxin damage. Additionally, its anti-inflammatory effect reduces neuroinflammatory responses by inhibiting the expression of pro-inflammatory factors.

Druggability evaluation and pharmacokinetics

Scheffoleoside A has a larger molecular weight (959.1330 Da) and a high TPSA value (315.21 Ų), indicating strong polarity, which may limit oral absorption and the ability to penetrate the blood-brain barrier. The LogP value is 1.92, indicating moderate lipid solubility that facilitates cell membrane penetration, but overall bioavailability may be limited.

Assessment of blood-brain barrier permeability shows low permeability, suggesting that its direct role in the central nervous system may be limited and requires structural modification or improved drug delivery through carrier systems. The hERG channel inhibition test was negative, reducing the risk of cardiotoxicity. The Ames test result was 0, indicating no mutagenicity and relatively high safety.

Currently, pharmacokinetic data on Scheffoleoside A are relatively scarce. Given its high polarity and large molecular weight, it is inferred that its metabolism in the body mainly involves glycoside hydrolysis through hepatic enzyme systems and triterpene skeleton metabolism, with excretion likely primarily via bile and urine. In the future, in vivo pharmacokinetic studies are needed to clarify its absorption, distribution, metabolism, and excretion (ADME) characteristics to provide a basis for clinical application.

Prospects and outlooks for clinical applications

Scheffoleoside A, as an important active ingredient in Centella asiatica, demonstrates broad clinical application potential due to its dual pharmacological activities of neuroprotective and skin repair.

In the field of neuroprotection, Scheffoleoside A is expected to become an adjunctive therapy for neurodegenerative diseases such as Parkinson's and Alzheimer's. Its antioxidant, anti-inflammatory, and anti-apoptotic effects can slow down the process of neuronal damage and improve patients' neurological function. However, the low blood-brain barrier permeability limits central functions, and future drug delivery system optimization or structural modification is needed to increase brain concentrations.

In the field of skin repair, Scheffoleoside A can be used as a topical ingredient to promote wound healing, reduce scar formation, and improve skin aging. Its ability to regulate multiple skin repair-related targets provides a theoretical basis for developing novel wound treatment drugs. Combined with modern formulation technologies, such as nanocarriers and transdermal drug delivery systems, it is expected to improve local bioavailability and therapeutic effects.

Additionally, Scheffoleoside A has a good safety profile, with hERG and Ames trials showing no significant toxicity, which is beneficial for clinical translation. In the future, it is necessary to strengthen in vivo efficacy evaluation, toxicology research, and clinical trial design, clarify effective doses and safe dosage ranges, and promote its transition from laboratory to clinical application.

Conclusion

Centella asiatica-28-O-rhamnose (1-4)glucose (1-6)glucoside (Scheffoleoside A), as an important triterpene saponin in Centella asiatica, exhibits significant neuroprotective and skin repair activities. Its complex glycoside structure endows it with unique physicochemical properties and biological functions. By regulating multiple key molecular targets, Scheffoleoside A plays a role in promoting cell proliferation, inhibiting inflammatory responses, and providing antioxidant properties, demonstrating promising pharmacological potential.

Although its high molecular weight and polarity limit oral absorption and blood-brain barrier penetration, its safety is good, providing favorable conditions for further drug development. In the future, modern drug delivery technologies and structural optimization strategies should be combined to overcome druggability bottlenecks and promote clinical application in neurodegenerative diseases and skin repair.

In summary, Scheffoleoside A, as a candidate molecule for natural product drugs, has broad research and application prospects and is worthy of in-depth and systematic research in pharmacological mechanisms, pharmacokinetics, and clinical translation.