Acanthopanaxoside A , CAS No.915792-02-8

CAS: 915792-02-8 Cat. No.: A1440873 Summenformel: C₆₀H₉₄O₂₇ Molekulargewicht: 1247.37

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Übersicht

Acanthopanaxoside A, a triterpenoid saponin, has pancreatic lipase inhibitory action.

Specifications

Storage

Store at -20°C

Verschickt in

Ice chest + Ice pads

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Aktionsart

INHIBITOR

Namen und Kennungen

Molekulargewicht

1247.37

Application Protocols

No manufacturer-tested biological assay protocols are provided for this item. The following general-use protocols are offered as starting points for analytical work; adapt as needed.

• LC–MS reference standard preparation (general):

  1. Equilibrate vial to room temperature in a desiccator.
  2. Accurately weigh 1–2 mg into a glass LC vial insert.
  3. Dissolve to 1.0 mg/mL in methanol (or DMSO if required). Sonicate briefly if needed.
  4. For calibration, prepare serial dilutions (e.g., 1.0 → 0.01 mg/mL) in MeOH/water (50:50) containing 0.1% formic acid; maintain ≥2% MeOH to prevent precipitation.
  5. Store working solutions at 4 °C for short term; freeze aliquots at −20 °C for long term.

• RP‑HPLC system suitability (general):

  1. Column: C18, 150–250 mm.
  2. Mobile phase: A = water + 0.1% formic acid; B = methanol.
  3. Gradient: 30–90% B over 25 min; flow 1.0 mL/min; column temp 30 °C.
  4. Detection: ELSD or MS; UV at 200–210 nm if required.
  5. Acceptance: consistent retention time (±2%), peak symmetry 0.9–1.5.

• NMR sample (general): Dissolve 3–10 mg in CD3OD or DMSO‑d6; acquire 1H, 13C, HSQC, HMBC, COSY at 25 °C. For sugar configuration, analyze anomeric coupling constants.

Note: These are generic guidelines for saponin-type analytes and are not item-specific test methods.

Biological Roles

Item-specific biological data are not provided. The following context is literature/general and intended to guide basic research planning only.

• Provenance: Acanthopanaxoside A has been reported as a constituent of Acanthopanax (Eleutherococcus) species (Araliaceae), a family known for triterpenoid saponins and related glycosides.
• Structural class: Saponin-type glycosides are amphiphilic molecules composed of a triterpene (or steroid) aglycone linked to one or more sugars. This architecture confers surfactant properties and the ability to interact with biological membranes.
• Biochemical interactions (in vitro, literature/general): Saponins can form complexes with membrane sterols, modulate membrane permeability, and influence vesicle and liposome integrity. They often exhibit hemolytic activity proportional to aglycone type and sugar chain arrangement. These effects are highly structure-dependent and concentration-dependent.
• Analytical biomarkers: Within plant metabolomics, such glycosides function as chemotaxonomic markers to differentiate species, plant parts, and processing states.
• Metabolism/degradation: In biological systems and microbial cultures, glycosidic bonds are susceptible to enzymatic hydrolysis (glycosidases), releasing sugar units and the aglycone; subsequent phase I/II transformations may occur (literature/general).

Important note: No medical, diagnostic, or therapeutic use is intended or claimed. Use strictly for laboratory research, method development, and phytochemical analysis.

Buffer Applications

This product is not a buffering reagent and does not define pH in solution. Therefore, dedicated “buffer recipes” do not apply.

Practical guidance (general):

• If preparing aqueous working solutions or assay media, dissolve Acanthopanaxoside A first in a miscible organic solvent (e.g., DMSO or ethanol), then dilute into a compatible biological buffer (PBS, HEPES, or Tris) while maintaining sufficient cosolvent (typically 1–2% v/v) to prevent precipitation.
• Maintain neutral to mildly acidic pH (ca. pH 5.5–7.4) to minimize non-enzymatic hydrolysis of glycosidic linkages during prolonged incubations. Avoid strong base.
• For biophysical studies, consider using surfactant-free buffers and low-binding plastics/glass to mitigate adsorption and micelle formation artifacts.

For precise composition and compatibility, optimize empirically in the context of your assay.

Green Alternatives

Context: For extraction, purification, and analytical use of plant glycosides like Acanthopanaxoside A, solvent choice drives the environmental footprint. While item-specific requirements may dictate certain solvents, consider the following greener practices (literature/general):

• Prefer ethanol–water over methanol for plant extraction when feasible. Ethanol is bio-based, less toxic, and widely accepted for green extraction.
• Replace chlorinated solvents (CHCl3, DCM) in normal-phase separations with EtOAc or MTBE where resolution allows. For ternary systems, EtOAc/MeOH/H2O can sometimes substitute CHCl3/MeOH/H2O.
• For RP‑HPLC, water–ethanol gradients (or MeOH) are greener than acetonitrile; test method robustness and detection sensitivity.
• Minimize DMSO usage in routine dissolution by employing ethanol or propylene carbonate when compatible with downstream assays (check solubility and assay tolerance).
• Employ solid-phase extraction (SPE) cleanup to reduce solvent volumes before preparative chromatography.

Illustrative comparison (general):

• Methanol vs Ethanol (extraction/mobile phase): Ethanol offers lower toxicity and renewable sourcing; methanol may deliver slightly higher solubility/elution strength for highly polar saponins—tradeoff is performance vs. safety.
• CHCl3 vs EtOAc (normal phase): EtOAc is less persistent and less hazardous; may require adjusting polarity with small % MeOH/H2O to match separation.

Always verify that green substitutions maintain analyte recovery, purity, and chromatographic selectivity for your specific method.

Pharmaceutical Uses

No pharmacopeial status, excipient role, or formulation specifications are provided for this item; it is supplied strictly for research use only.

General R&D and manufacturing-adjacent contexts (non-clinical, literature/general):

• Analytical reference: Can serve as a reference standard in QC of botanical raw materials and extracts (identification tests, system suitability, retention time locking) when developing in-house monographs.
• Process development: Used to evaluate extraction/partitioning procedures (ethanol–water optimization, solid–liquid ratios) and to validate clean-up steps (SPE method development) for Araliaceae matrices.
• Stability studies: Employed to establish stress conditions (acid/base hydrolysis, oxidative, thermal, photolytic) and to develop stability-indicating HPLC methods for complex glycosides.
• Formulation research: In pre-formulation studies, its amphiphilicity may be leveraged to study self-assembly/micellization phenomena; however, no claims are made regarding suitability or safety for human or veterinary use.

Compliance note: Do not use in any drug product or clinical study without appropriate qualification and regulatory review. For cGMP or compendial needs, contact us to discuss documentation and lot control requirements.

Physical Properties

Item-specific quantitative properties:

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point: Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point: Not applicable (decomposes before boiling, typical for complex glycosides; literature/general).
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not applicable to solids; if oily/foamy solid, Not specified for this item; refer to CoA/Spec Sheet.
• Solubility: Not specified for this item; refer to CoA/Spec Sheet.
• LogP/logD: Not specified for this item; refer to CoA/Spec Sheet.
• pKa: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general behavior for triterpenoid saponins (for planning purposes only):

• Physical form: typically amorphous to microcrystalline solids that can appear off-white due to minor impurities.
• Solubility profile: often soluble in polar organic solvents (methanol, ethanol, n‑butanol) and DMSO; sparingly soluble in acetonitrile/ethyl acetate; limited solubility in water but can form micelles/foams due to surfactant character. Actual solubility is structure- and lot-dependent—verify experimentally.
• Thermal characteristics: many saponins darken and decompose >180–220 °C without a sharp melt (literature). Avoid prolonged heating.
• Chromatographic behavior: retain strongly on RP‑HPLC; elute with water–acetonitrile or water–methanol gradients containing 0.05–0.1% acid modifier. On normal phase, often require CHCl3/MeOH/H2O mixtures.

Important note: Do not treat the above as specifications. For quantitative release values and acceptance limits, consult the item’s CoA/Spec Sheet.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

Interpretation and expectations:

• For natural products such as Acanthopanaxoside A, quality is commonly demonstrated by chromatographic purity (e.g., RP‑HPLC area %) and orthogonal identity confirmation (HRMS, 1H/13C NMR). If a grade (e.g., “analytical standard,” “≥95% HPLC”) is assigned on the CoA, it indicates the minimum acceptance criterion measured by a validated assay.
• Impurities in plant-derived glycosides may include closely related saponins (positional isomers, different sugar sequences), aglycone fragments, residual solvents, and water. Acceptance criteria, if applicable, will be defined on the CoA.
• UV absorbance characteristics and LC-MS response factors can vary across lots due to microheterogeneity; for quantitative work, establish a lot-specific calibration curve.
• Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. Most saponins are shipped without stabilizers; if any excipient (e.g., mannitol) is present, it will be listed on the CoA.
• Documentation: Each lot should be supported by an SDS and a CoA (purity, identity data, and storage guidelines). For regulated analytical applications, retain copies of chromatograms and spectra.

Recommendations for users:

• Upon receipt, verify identity by LC–MS and retain a small aliquot as an in-house reference. If you require a tighter purity assurance (e.g., ≥98% by qNMR), contact us before ordering to confirm availability.

Reaction and Applications

Manufacturer application text: Not provided for this item.

Research and analytical applications (literature/general):

• Reference standard: Used as an analytical reference to characterize and quantify Acanthopanax/Eleutherococcus extracts by LC–UV/LC–MS, supporting botanical authentication, dereplication, and quality control.
• Metabolomics/natural products workflows: Serves as a marker compound in targeted metabolomics panels for Araliaceae species; facilitates peak identification by retention time and MS/MS library matching.
• Spectroscopic characterization: Useful for NMR method development on complex glycosides (assignment of sugar anomeric protons/carbons, HMBC correlations establishing linkage positions).
• Surface-active behavior: As a saponin-class compound (literature), can form micelles and foams; exploited in studying membrane interactions, permeability assays, and hemolytic potential in vitro (research use only).

Practical tips:

• Sample preparation: Prepare concentrated stocks in MeOH or DMSO. Filter sample solutions (0.22 µm PTFE) prior to HPLC to remove particulates; PVDF/nylon may adsorb amphiphiles—evaluate recovery.
• LC–MS considerations: Employ soft ionization (ESI), monitor characteristic glycosidic neutral losses (e.g., 162, 146 amu for hexose/rhamnose; literature/general). Optimize source temperature to balance desolvation with thermal stability.
• Stability: Protect from strong acids/bases and elevated temperatures; avoid extended exposure to aqueous buffers, which may promote slow hydrolysis. Work cold and dry for sample archiving.

Note: The above applications reflect general use of saponin-type glycosides; confirm suitability for your specific assay.

Reaction Conditions

No item-specific reactivity parameters are provided. The following are literature/general conditions commonly employed for saponin-type glycosides and should be validated for Acanthopanaxoside A before scale-up:

• Per‑O‑acetylation: Ac2O/pyridine (or Ac2O/DMAP in CH2Cl2) at 0–25 °C, 1–12 h, monitoring by TLC/RP‑HPLC. Quench into MeOH/H2O, neutralize, and purify by column chromatography.
• Selective acylation/silylation: Use sterically hindered bases (2,6‑lutidine) and bulky reagents (TBDMS‑Cl, TBDPS‑Cl) at 0–25 °C with catalytic DMAP; control equivalents to target primary OH.
• Acidic hydrolysis of glycosides: 0.01–0.1 M HCl in 50–80% aqueous MeOH, 25–60 °C, 0.5–6 h; isolate aglycone and sugars. Minimize overhydrolysis by close monitoring (LC‑MS).
• Enzymatic cleavage: β‑glucosidase or specific glycosidases in acetate/phosphate buffer (pH 5–6), 25–37 °C, hours to days.
• Oxidative modifications: Periodate oxidation (NaIO4) of sugar vicinal diols at 0–4 °C in aqueous alcohols; follow with NaBH4 reduction or derivatization as required.

Analytical method conditions (general):

• RP‑HPLC: C18, 5 µm, 250 × 4.6 mm; mobile phase A: water + 0.1% formic acid; B: MeOH or ACN; gradient 20→95% B over 30–40 min; detection by ELSD or UV (weak chromophore; often <210 nm) and by MS (ESI).
• Sample handling: Prepare 1–10 mg/mL stocks in MeOH or DMSO. Store aliquots at −20 °C; avoid repeated freeze–thaw.

These conditions are representative; optimize for your specific substrate and analytical endpoints.

Safety and Handling

Authoritative safety information for this specific item (GHS):

• Signal word: Not specified for this item; refer to SDS.
• Hazard statements (H-codes): Not specified for this item; refer to SDS.
• GHS classification and pictograms: Not specified for this item; refer to SDS.

General laboratory precautions (non-specific, best practice):

• Handle in a chemical fume hood; avoid inhalation of powders and contact with skin/eyes. Wear appropriate PPE: lab coat, nitrile gloves, and splash goggles. Wash thoroughly after handling.
• Avoid creating dust/aerosols. Use antistatic measures when weighing fine powders.
• Incompatibilities: strong oxidants and strong acids/bases may degrade glycosidic natural products; avoid prolonged exposure to moisture and heat. Protect from light when feasible.
• First-aid overview: If inhaled—move to fresh air; seek medical advice if symptoms persist. Skin contact—wash with soap and water. Eye contact—rinse cautiously with water for several minutes; remove contact lenses if present and easy; seek medical attention if irritation continues. Ingestion—rinse mouth; do not induce vomiting; obtain medical attention.
• Spill/cleanup: Avoid dust. Sweep up with minimal agitation; place in a suitable container for disposal according to institutional and local regulations.
• Fire response: Use CO2, dry chemical, or foam. Combustion may produce CO/CO2 and irritant fumes; firefighters should wear SCBA.

Always consult the product-specific SDS for definitive hazard, exposure limits, and emergency procedures.

Solvent Selection

Item-specific solubility is not provided for this product; verify experimentally and consult the CoA/Spec Sheet.

General solvent guidance for triterpenoid saponins and related glycosides (literature/general):

• Primary solvents for dissolution at analytical scale: DMSO (excellent solvating power for amphiphiles), methanol, ethanol. For aqueous assays, prepare a DMSO or EtOH stock and dilute into buffered saline with gentle mixing; avoid precipitation by keeping final organic content ≥1–2% v/v.
• Water solubility: variable; many saponins disperse to form colloids/micelles and foam. True molecular solubility may be modest. Warming to 30–40 °C and sonication can aid dissolution.
• Partitioning: amphiphilic molecules may adhere to plastics at low concentrations; use glass vials and pipette tips with low-retention surfaces for quantitative work.
• For preparative chromatography:
  • Normal phase: CHCl3/MeOH/H2O ternary systems (e.g., 65:35:10 with phase separation management) or EtOAc/MeOH/H2O; adjust with NH4OAc to improve peak shape.
  • Reversed phase: Water–acetonitrile or water–methanol with 0.05–0.1% formic acid to enhance MS response and reproducibility.
• Avoid strongly basic conditions during dissolution, which can promote glycosidic hydrolysis.

Comparison (literature/general):

• DMSO: highest solvency, but may complicate bioassays at >0.5–1% v/v.
• Methanol/Ethanol: greener and volatile; suitable for stock solutions and HPLC.
• ACN: often less effective for highly hydroxylated saponins; use mainly for RP‑HPLC elution.

Storage and Reconstitution

Item-specific storage and shipping:

• Storage conditions: Store at −20 °C (per product data). Keep container tightly closed in a dry, inert atmosphere. Protect from light and moisture.
• Shipped in: Ice chest + ice pads (per product data) to maintain cold chain.

Reconstitution and handling (general guidance for glycosides):

• Upon receipt, allow the sealed container to equilibrate to room temperature in a desiccator before opening to prevent moisture condensation.
• For stock solutions, dissolve in methanol, ethanol, or DMSO at 1–10 mg/mL. If preparing aqueous solutions, dilute an organic stock into buffer while maintaining 1–2% v/v organic to avoid precipitation.
• Aliquot stock solutions into amber vials to minimize freeze–thaw cycles; purge headspace with inert gas if long-term storage is planned.

Stability guidance:

• Solid state: When stored dry at −20 °C and protected from light, complex glycosides are generally stable for many months. Actual retest/expiry dates are per CoA/Spec Sheet.
• Solution: Store at −20 °C; avoid repeated freeze–thaw. Monitor for degradation by LC–MS/HPLC (appearance of aglycone or sugar-loss peaks). Acidic or basic media can accelerate hydrolysis—prefer neutral to mildly acidic conditions for short-term work.

Always refer to the CoA/Spec Sheet for lot-specific stability data and to the SDS for safe handling during reconstitution.

Structure and Identity

• Product name: Acanthopanaxoside A (SKU: A1440873)
• CAS: 915792-02-8
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

Structural overview (literature/general):

• Acanthopanaxoside A is reported in the phytochemistry literature as a plant secondary metabolite isolated from Acanthopanax/Eleutherococcus spp., typically categorized among triterpenoid saponins (glycosides of a pentacyclic triterpene aglycone) or related multi-glycosylated natural products.
• Common structural motifs for such saponins include: a hydrophobic pentacyclic triterpene core (e.g., oleanane/ursane type, literature) bearing multiple hydroxyl groups, and one or more O‑glycosidic linkages to a carbohydrate chain (glucose, rhamnose, arabinose, etc.), often terminally acetylated or otherwise decorated. The exact sugar sequence, linkages, and aglycone for Acanthopanaxoside A should be verified from the CoA/Spec Sheet or primary literature for this specific lot.
• 2D description (literature/general): central polycyclic hydrophobic skeleton with appended polyhydroxy sugar residues; multiple stereocenters at the aglycone ring junctions and within the monosaccharide units; glycosidic anomeric configurations typically defined (α/β) at each sugar–oxygen linkage.

Identity confirmation guidance:

• Recommend confirming by high-resolution LC–MS (accurate mass and characteristic adducts), diagnostic MS/MS glycosidic cleavages, and 1D/2D NMR (1H, 13C, HSQC, HMBC, COSY) to establish sugar sequence and substitution pattern. Use of an authentic reference spectrum is advised.

Synthetic Utility

Although primarily sourced as an isolated natural product, Acanthopanaxoside A can be a valuable substrate or benchmark in synthetic and semi-synthetic studies (literature/general):

• Derivatization chemistry:
  • Selective acylation or silylation of sugar hydroxyls to probe structure–activity relationships and modulate polarity.
  • Periodate-mediated oxidative cleavage of vicinal diols (on sugars) followed by reductive steps to map connectivity.
  • Per-acetylation for improved chromatographic behavior and crystallization during structural studies.
• Glycosidic manipulation:
  • Acid-catalyzed hydrolysis (very mild, aqueous MeOH with catalytic acid) to release the aglycone and individual sugars for identification.
  • Enzymatic deglycosylation using specific glycosidases to dissect sugar sequence and anomeric configurations.
• Analytical synthesis:
  • Preparation of isotopically labeled analogs (e.g., 13C-enriched sugars) for NMR assignment and quantitative isotope-dilution LC–MS.
• Retrosynthetic value (conceptual): the molecule exemplifies strategies for assembling densely functionalized frameworks—iterative glycosylations with protecting-group orchestration onto a polyhydroxylated triterpene scaffold.

Caveats:

• The compound contains multiple stereocenters and acid/base-labile linkages; maintain low temperatures and neutral to mildly acidic conditions for manipulations.
• Protecting-group strategies should balance stability with deprotection orthogonality to avoid aglycone rearrangements or sugar elimination.

Target Specificity

Not applicable. This product is a small-molecule natural product standard, not an antibody, enzyme, or affinity reagent. No antigen/epitope or species reactivity information applies to this item.