Paeoniflorin
[CAS# 23180-57-6]

Identification

• Classification: Biochemical >> Natural biochemical product
• Name: Paeoniflorin
• Synonyms: 5beta-[(Benzoyloxy)methyl]tetrahydro-5-hydroxy-2-methyl-2,5-methano-1H-3,4-dioxacyclobuta[cd]pentalen-1alpha(2H)-yl-beta-D-glucopyranoside
• Molecular Formula: C₂₃H₂₈O₁₁
• Molecular Weight: 480.47
• CAS Registry Number: 23180-57-6
• EC Number: 245-476-2
• SMILES: C[C@]12C[C@@]3([C@@H]4C[C@]1([C@@]4([C@H](O2)O3)COC(=O)C5=CC=CC=C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O

Properties

• Density: 1.6±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.686, Calc.^*
• Boiling Point: 683.3±55.0 °C (760 mmHg), Calc.^*
• Flash Point: 235.9±25.0 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P264-P270-P301+P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

Paeoniflorin is a major bioactive compound derived from the roots of Paeonia lactiflora, commonly known as white peony, a traditional medicinal herb extensively used in Chinese medicine for centuries. The discovery of paeoniflorin dates back to the early 20th century when researchers began isolating and characterizing the various constituents of peony roots. Its structure was elucidated in the 1940s, revealing it as a monoterpene glycoside with significant pharmacological properties. Since then, extensive research has been conducted to explore its therapeutic potential, leading to its recognition as a key ingredient in various herbal formulations.

Chemically, paeoniflorin is a glycoside, consisting of a paeonol aglycone linked to a glucose molecule. Its unique structure is responsible for its diverse biological activities. Paeoniflorin is typically extracted from the dried roots of Paeonia lactiflora through water or alcohol extraction methods, followed by purification techniques such as chromatography. Its extraction and purification have allowed researchers to conduct numerous studies on its health benefits.

Paeoniflorin is renowned for its anti-inflammatory effects. Research indicates that it can inhibit the production of pro-inflammatory cytokines and enzymes, making it beneficial for treating inflammatory diseases. It has been shown to alleviate symptoms in conditions such as arthritis, where inflammation plays a significant role. The compound's ability to modulate immune responses further supports its therapeutic potential in managing various inflammatory disorders.

In addition to its anti-inflammatory properties, paeoniflorin exhibits neuroprotective effects. Studies have demonstrated that it can protect neuronal cells from damage caused by oxidative stress and neuroinflammation. This property makes paeoniflorin a candidate for developing treatments for neurodegenerative diseases, such as Alzheimer’s and Parkinson’s disease. Research suggests that it may improve cognitive function and memory by promoting neuronal survival and enhancing synaptic plasticity.

Paeoniflorin has also been investigated for its analgesic properties. It has been shown to effectively reduce pain in various animal models, indicating its potential for use in pain management therapies. The compound's analgesic effects are believed to be associated with its action on the central nervous system, where it may modulate pain perception pathways.

Moreover, paeoniflorin is recognized for its hepatoprotective effects. Studies have indicated that it can protect the liver from damage induced by toxic substances, thereby supporting liver health. This property is particularly significant in the context of drug-induced liver injury and liver diseases.

Recent advancements in formulation technologies have expanded the applications of paeoniflorin. Innovative delivery systems, such as nanoparticles and liposomes, are being explored to enhance its bioavailability and target specific tissues more effectively. These advancements may lead to the development of more effective therapeutic formulations containing paeoniflorin for various health applications.

In summary, paeoniflorin is a crucial bioactive compound derived from Paeonia lactiflora, with a long history of use in traditional medicine and a wide range of pharmacological properties. Its anti-inflammatory, neuroprotective, analgesic, and hepatoprotective effects make it a promising candidate for various therapeutic applications. Ongoing research continues to unveil its mechanisms of action and potential benefits, solidifying paeoniflorin’s place in the field of natural remedies and health-promoting compounds.

References

2024. Antioxidant effects of Paeoniflorin and relevant molecular mechanisms as related to a variety of diseases: A review. *Biomedicine & Pharmacotherapy*, 176.
DOI: 10.1016/j.biopha.2024.116772

2024. Synthesis, Antioxidant Activity, and Molecular Docking of Novel Paeoniflorin Derivatives. *Chemical Biology & Drug Design*, 104(4).
DOI: 10.1111/cbdd.14629

1982. Biologically active principles of crude drugs. II. Anti-allergic principles in "SHOSEIRYU-TO" anti-inflammatory properties of paeoniflorin and its derivatives. *Journal of Pharmacobio-Dynamics*, 5(11).
DOI: 10.1248/bpb1978.5.921