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Lithospermic acid B (identical to salvianolic acid B) is a dimeric phenolic acid (C₃₆H₃₀O₁₆) found in plants like Salvia miltiorrhiza (Danshen).
Key features:
Structure: Composed of rosmarinic acid linked to danshensu (salvianic acid A) via ester bonds.
Functional groups: Contains four catechol units (ortho-dihydroxyphenyl) and carboxylic acids, making it highly water-soluble and a potent antioxidant.
Bioactivity: Protects cardiovascular/liver/neural tissues by scavenging free radicals, reducing inflammation, and inhibiting fibrosis.
Stability: Light/heat-sensitive; degrades in alkaline conditions.
Name note: "Lithospermic acid B" (historically from Lithospermum) = "Salvianolic acid B" (from Danshen); distinct from monomeric lithospermic acid (C₂₇H₂₂O₁₂).
CAS: 121521-90-2; Key applications: herbal medicine (e.g., cardiovascular drugs), antioxidant research.
Lithospermic acid B is chemically identical to salvianolic acid B (Sal B), which is a prominent bioactive compound derived from Salvia miltiorrhiza (Danshen). Here is its chemical characterization:
Structural Class:
Dimeric phenolic acid formed from rosmarinic acid and danshensu (salvianic acid A) units.
Comprises four phenylpropanoid subunits (caffeic acid derivatives).
Molecular Formula: C₃₆H₃₀O₁₆
Molecular Weight: 718.6 g/mol.
Core Functional Groups:
Two ester bonds: Linking danshensu and two caffeic acid residues.
Four catechol groups (ortho-dihydroxyphenyl): Responsible for potent antioxidant activity.
Carboxylic acid groups (–COOH): Enhancing water solubility.
Labile lactone ring: Easily hydrolyzed under heat/alkaline conditions.
Stereochemistry:
Contains chiral centers (e.g., in danshensu unit), typically existing as a racemic mixture in natural extracts.
Systematic Name:
β-[[2-O-(3,4-Dihydroxybenzoyl)-3-(3,4-dihydroxyphenyl)-1-oxopropoxy]-3,4-dihydroxybenzenepropanoic acid.
| Property | Description |
|---|---|
| Solubility | Highly water-soluble (polar groups) |
| Stability | Sensitive to light, heat, and pH; degrades in alkaline conditions |
| Reactivity | Strong antioxidant (electron-donating catechol groups) |
| Chromatography | Detected via HPLC-UV (λ~max~ ≈ 286 nm) |
Lithospermic acid (monomeric) is a precursor to lithospermic acid B (dimeric).
Lithospermic acid formula: C₂₇H₂₂O₁₂; lacks one caffeic acid unit compared to Sal B.
Note: In pharmacology and botany, "lithospermic acid B" and "salvianolic acid B" are used interchangeably. Its dimeric structure underpins its potent bioactivities (antioxidant, cardioprotective, etc.).
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