Cryptomeridiol 11-rhamnoside 98% Purity CAS 349112-30-7 Research Grade Sesquiterpenoid Glycoside Reference Standard for Natural Product Analysis and B

• Product Overview

  Cryptomeridiol 11‑rhamnoside (CAS 349112‑30‑7) is a high‑purity naturally occurring glycosylated sesquiterpenoid reference standard. The molecular formula is C₂₁H₃₈O₆ with a molecular weight of 386.53 g/mol. This compound features a cryptomeridiol aglycone (a bicyclic sesquiterpene alcohol with the eudesmane skeleton) glycosylated at the 11‑position with an α‑L‑rhamnoside moiety. The IUPAC name is (2S,3R,4R,5R,6S)-2-[2-[(2R,4aR,8R,8aR)-8‑hydroxy‑4a,8‑dimethyl‑1,2,3,4,5,6,7,8a‑octahydronaphthalen‑2‑yl]propan‑2‑yloxy]‑6‑methyloxane‑3,4,5‑triol.

  The compound is isolated from the branches of Eucalyptus globulus Labill. and is also found in Cryptomeria japonica (Japanese cedar), where it is synthesized as part of the plant's secondary metabolite profile. As a research‑grade reference standard, it is intended exclusively for scientific research purposes, including content determination, bioactivity screening, and natural product analysis. The product is supplied at ≥98.0% purity as determined by HPLC and is manufactured under strict quality control to ensure batch‑to‑batch consistency.

  Biological Activity

  Cryptomeridiol 11‑rhamnoside has demonstrated significant biological activities in preclinical studies:

  • Cytotoxicity: This compound has been evaluated for its cytotoxic effects against human cancer cell lines. Studies indicate that it exhibits cytotoxic activity against HepG2 human hepatocellular carcinoma cells with an IC₅₀ value of 0.01 μg/mL, and against HepG2(2.2.15) cells (a stable HBV‑expressing cell line) with an IC₅₀ of 0.36 μg/mL.

  • Anti‑inflammatory Potential: It interacts with cellular receptors and enzymes, potentially modulating inflammatory signaling pathways and reducing inflammatory responses.

  • Antioxidant Properties: The compound may influence cellular oxidative stress through its interaction with biochemical pathways involved in redox balance.

  • Antimicrobial Activity: Preliminary research suggests potential antimicrobial properties, though specific mechanisms are still under investigation.

  Mechanism of Action

  As a glycosylated sesquiterpenoid, cryptomeridiol 11‑rhamnoside exerts its bioactivity through multiple biochemical pathways:

  • Cellular Receptor Modulation: The compound interacts with specific cellular receptors, potentially influencing downstream signaling cascades involved in cell survival, proliferation, and apoptosis.

  • Enzyme Interaction: It may modulate the activity of enzymes involved in inflammatory and oxidative stress pathways, contributing to its observed anti‑inflammatory and antioxidant effects.

  • Secondary Metabolite Role: As a plant secondary metabolite, it may function as a defense compound, protecting the source plants from pathogens and herbivores, which correlates with its observed antimicrobial and cytotoxic activities.

  Synthetic Process / Isolation Method

  Cryptomeridiol 11‑rhamnoside is isolated from natural plant sources:

  • Extraction: Dried plant material (branches of Eucalyptus globulus or other source species) is extracted with organic solvents such as ethanol or methanol.

  • Partitioning: The crude extract is subjected to liquid‑liquid partitioning to concentrate the glycosylated terpenoid fraction.

  • Column Chromatography: The enriched fraction undergoes repeated column chromatography using silica gel, Sephadex LH‑20, or preparative HPLC to isolate the target compound.

  • Recrystallization: The purified compound is recrystallized from appropriate solvent systems to achieve ≥98% purity.

  • Quality Confirmation: The final product is rigorously characterized by HPLC (purity ≥98%), ¹H‑NMR, ¹³C‑NMR, and mass spectrometry to confirm structural identity and purity.

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