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Protopine

Protopine is a benzylisoquinoline alkaloid with the molecular formula C₂₀H₁₉NO₅ and CAS number 130-86-9, naturally occurring in various plants of the Papaveraceae and Fumariaceae families, including Corydalis yanhusuo, Papaver somniferum (opium poppy), Fumaria officinalis, and Glaucium species.^[1]^[2]^[3] Derived biosynthetically from (S)-reticuline, it features a characteristic methyl substituent on the nitrogen atom and oxygen-containing groups on the aromatic rings, contributing to its pharmacological profile as a multifunctional bioactive compound.^[4] This alkaloid is renowned for its diverse therapeutic potential, acting as a histamine H₁ receptor antagonist, opioid-like analgesic, and inhibitor of platelet aggregation.^[4] Key pharmacological activities include antiarrhythmic effects by blocking multiple ion channels (such as I_Ca-L, I_Kr, and I_Na), which reduce ventricular fibrillation incidence in animal models; antihypertensive and cardioprotective properties; and anti-inflammatory, neuroprotective, and anticancer actions through mechanisms like apoptosis induction in tumor cells (e.g., IC₅₀ values of 6.68 µM for HL-60 leukemia cells and 20.47 µM for A-549 lung cancer cells). As of 2025, ongoing research explores its potential in breast cancer therapy, cardioprotection under hypoxic conditions, and antimicrobial activity against pathogens like Escherichia coli.^[2]^[5]^[6]^[7]^[8] Additionally, protopine demonstrates spasmolytic, smooth muscle stimulant, antibacterial, antifungal, and antimalarial effects, with low tissue residue levels (<6.5 ng/g) observed in pharmacokinetic studies following oral administration in rats.^[1]^[3]^[4] Protopine's metabolism involves phase I (demethylation, ring cleavage) and phase II (glucuronidation) pathways, yielding multiple metabolites detectable in plasma, urine, feces, and cecal contents, while its pharmacokinetics reveal wide tissue distribution but minimal accumulation.^[3]^[5] Although generally considered safe at therapeutic doses, it may exhibit cytotoxicity in high concentrations and potential hepatotoxicity, as associated with certain alkaloid-rich plants, underscoring the need for further toxicological research.^[5] Traditionally used in Chinese medicine from Corydalis tubers for pain relief and cardiovascular support, protopine continues to be investigated for its role in mitigating morphine withdrawal and as a component in herbal preparations for inflammatory and thrombotic conditions.^[2]^[4]

Chemical Characteristics

Molecular Structure

Protopine is a naturally occurring isoquinoline alkaloid characterized by the molecular formula C₂₀H₁₉NO₅ and a molar mass of 353.37 g/mol.^[9] Its systematic IUPAC name is (13aS)-5,13a-dihydro-2,3,9,10-tetramethoxy-6H-dibenzo[f,g]isoquino[1,9a,3,4]oxadiazolo[3,2-a]azecin-7-one, though commonly referred to by its trivial name.^[9] This formula reflects its composition of 20 carbon atoms, 19 hydrogen atoms, one nitrogen atom, and five oxygen atoms, consistent with its classification as a protoberberine-derived compound.^[9] The core structure of protopine features a tricyclic system composed of two benzene rings (designated as rings A and C) fused and connected via a central ten-membered heterocyclic ring (ring B) that includes a nitrogen atom.^[10] This arrangement incorporates methylenedioxy groups on the benzene rings and a lactam functionality in the central ring, contributing to its rigidity and characteristic alkaloid profile. The nitrogen in the central ring is N-methylated, and the structure includes ether linkages from the methylenedioxy groups.^[4] Protopine represents a ring-opened derivative of protoberberine alkaloids, where the B and C rings of the parent protoberberine skeleton undergo oxidative cleavage, resulting in the expanded central ring and altered connectivity.^[4] This structural modification distinguishes protopine within the isoquinoline alkaloid family while maintaining biosynthetic ties to protoberberines.^[10]

Physical and Chemical Properties

Protopine is a white to light yellow crystalline solid at room temperature.^[11] Its melting point is 208 °C.^[9] The calculated density of protopine is 1.399 g/cm³.^[9] Protopine exhibits low solubility in water, rendering it practically insoluble under standard conditions. It demonstrates good solubility in organic solvents, including chloroform at a 1:15 ratio, ethanol, and acetone.^[9] The compound remains stable under ordinary storage conditions but is sensitive to light, which can lead to degradation.^[12] Spectroscopic techniques are essential for the identification and characterization of protopine. In ultraviolet-visible (UV-Vis) spectroscopy, it shows a maximum absorption at 293 nm in methanol (log ε = 3.93).^[13] Infrared (IR) spectroscopy reveals a characteristic peak at 1675 cm⁻¹ (KBr), attributable to carbonyl-amide interactions.^[13] For nuclear magnetic resonance (NMR), key ¹H NMR signals in acetone-d₆ (500 MHz) include multiplets at 2.04–3.83 ppm (8H, aliphatic protons), singlets at 5.93 and 5.97 ppm (each 2H, methylenedioxy groups), aromatic singlets and doublets between 6.63 and 6.91 ppm (4H), and a singlet at 1.88 ppm (3H, N-methyl).^[13]

Occurrence and Biosynthesis

Natural Sources

Protopine is primarily found in plants belonging to the Papaveraceae family (including the Fumarioideae subfamily), where it occurs as a benzylisoquinoline alkaloid.^[9] Key species include Papaver somniferum (opium poppy), Corydalis yanhusuo, Fumaria officinalis, and Chelidonium majus.^[9]^[14] Concentration levels of protopine vary by plant species and tissue, with higher amounts typically in underground parts. In Corydalis yanhusuo tubers, protopine is a significant component of the alkaloid profile, though levels fluctuate based on cultivation and processing conditions.^[15] In Papaver somniferum, protopine is a minor alkaloid compared to dominant ones like morphine.^[16] These protopine-containing plants are distributed across temperate regions globally. Corydalis yanhusuo is native to southwestern China and parts of Asia, including the Himalayas, while Papaver somniferum originates from the Mediterranean but is widely cultivated in Asia (e.g., India, Turkey) and Europe for medicinal and ornamental purposes.^[17] Fumaria officinalis is widespread in Europe, northern Asia, and introduced to North America, often growing in disturbed soils.^[14] Many of these species are cultivated specifically for medicinal extraction in Asia and Europe.^[18] Protopine is typically isolated from plant roots or tubers through solvent-based extraction methods. Common approaches involve maceration or Soxhlet extraction using organic solvents such as ethanol or chloroform, which effectively dissolve the alkaloid due to its solubility properties.^[19]^[20] These techniques allow for the separation of protopine from other alkaloids in the plant matrix.^[21] Commercially, protopine is available as a component of herbal extracts, particularly in traditional Chinese medicine formulations like Yan Hu Suo (Corydalis yanhusuo rhizome), where it contributes to the overall alkaloid profile of pain-relief preparations.^[22] These extracts are processed into granules, powders, or tinctures and distributed through herbal supplement suppliers for medicinal use.^[23]

Biosynthetic Pathway

Protopine is biosynthesized in plants of the Papaveraceae family from the benzylisoquinoline alkaloid precursor (S)-reticuline through a series of five enzymatic transformations that establish its characteristic tetracyclic structure with a protoberberine core.^[24] The pathway begins with the berberine bridge enzyme (BBE), an FAD-dependent oxidoreductase, which catalyzes the stereospecific oxidation of (S)-reticuline to form the methylene bridge, yielding (S)-scoulerine and initiating the protoberberine skeleton. Subsequent steps involve cytochrome P450 monooxygenases: cheilanthifoline synthase (CHS, CYP719A5) converts (S)-scoulerine to (S)-cheilanthifoline via 3'-hydroxylation, followed by stylopine synthase (STS, CYP719A) that introduces a methylenedioxy bridge to produce (S)-stylopine.^[24]^[25] The pathway proceeds with (S)-tetrahydroprotoberberine N-methyltransferase (TNMT), which methylates (S)-stylopine at the nitrogen to form the quaternary salt (S)-cis-N-methylstylopine (also known as allocryptopine), setting the stage for ring modification. The final transformation is mediated by (S)-cis-N-methylstylopine 14-hydroxylase (MSH, CYP719A25), a cytochrome P450 enzyme that hydroxylates the C-14 position, triggering spontaneous C-N bond cleavage and ring opening to yield protopine.^[24] Although protopine 6-hydroxylase (P6H, CYP82N) is involved in downstream conversion to dihydrosanguinarine in related benzophenanthridine pathways, it is not required for protopine formation itself.^[24] This sequence can be visualized as a linear progression: (S)-reticuline → (S)-scoulerine → (S)-cheilanthifoline → (S)-stylopine → allocryptopine → protopine, highlighting the role of oxidative cyclization and rearrangement in structural diversification. The genetic regulation of protopine biosynthesis relies on a coordinated network of cytochrome P450 enzymes and oxidoreductases, primarily expressed in the sieve elements and laticifers of Papaveraceae species such as Papaver somniferum and Corydalis species.^[24] Transcription factors like WRKY regulate these genes, ensuring compartmentalized synthesis within specialized plant cells.^[26] The protopine pathway represents a key branch in the diversification of protoberberine alkaloids, involving cytochrome P450 gene duplications that enable structural variations.^[27]

Pharmacological Profile

Biological Activities

Protopine exhibits diverse receptor interactions that contribute to its physiological effects. It acts as an antagonist at histamine H1 receptors, selectively binding without activation to block endogenous histamine actions, thereby modulating allergic responses. Additionally, protopine blocks voltage-gated calcium channels, suppressing calcium influx in vascular smooth muscle and neuronal tissues, which underlies its vasorelaxant and antiarrhythmic properties.^[9]^[28] The anti-inflammatory effects of protopine primarily involve inhibition of the NF-κB signaling pathway, leading to reduced production of pro-inflammatory cytokines such as TNF-α and IL-6. In lipopolysaccharide-stimulated macrophages, protopine attenuates NF-κB activation by preventing IκBα phosphorylation and p65 nuclear translocation, thereby decreasing inflammatory mediator release. This mechanism has been demonstrated in models of acute inflammation, where protopine dose-dependently suppresses cytokine expression and edema formation.^[29]^[30] In the cardiovascular system, protopine inhibits platelet aggregation by interfering with ADP- and collagen-induced pathways. It suppresses ADP-evoked shape change and aggregation in platelet-rich plasma, likely through interference with purinergic receptors and downstream signaling, while also reducing collagen-triggered responses via modulation of glycoprotein receptors. These actions contribute to its antithrombotic potential without significantly affecting prostacyclin pathways.^[31]^[32] Protopine displays antimicrobial properties, particularly against Gram-positive bacteria like Staphylococcus aureus, where it exhibits significant inhibitory activity with a minimum inhibitory concentration of 125 µg/mL. Its antibacterial mechanism may involve disruption of bacterial cell membranes or interference with essential enzymes, as observed in extracts rich in protopine from Hypecoum erectum. Against fungi, protopine shows weak to moderate activity toward Candida species, including C. albicans, contributing to the antifungal effects of alkaloid mixtures from plants like Glaucium oxylobum.^[33]^[34] The analgesic mechanism of protopine involves modulation of opioid receptors, particularly through activation of μ- and κ-subtypes, as evidenced by antagonism of its effects by naloxone in pain models. Furthermore, it inhibits cyclooxygenase (COX) enzymes, especially COX-2, reducing prostaglandin E2 synthesis in inflamed tissues and enhancing pain relief in inflammatory conditions. These dual actions—opioid agonism and COX inhibition—provide a multifaceted approach to analgesia without strong sedative side effects at therapeutic doses.^[35]^[29]

Therapeutic Applications and Research

Protopine, a key alkaloid in plants like Corydalis yanhusuo (Yan Hu Suo), has been utilized in traditional Chinese medicine for its analgesic and sedative properties, particularly in formulations aimed at relieving various types of pain, such as headache, abdominal discomfort, and menstrual pain associated with blood stasis. These traditional applications stem from the herb's role in promoting blood circulation and alleviating qi stagnation, with protopine contributing to the overall pain-relieving effects observed in clinical practice over centuries.^[36]^[37] Modern research has explored protopine's potential in several therapeutic areas, including anti-cancer effects through induction of apoptosis in tumor cells, such as those from liver, breast, and colon cancers, often via pathways involving ROS accumulation and caspase activation. Studies have also investigated its anti-neurodegenerative properties, demonstrating neuroprotection in models of cerebral ischemia and tau pathology relevant to Alzheimer's disease, with derivatives like bromo-protopine enhancing tau degradation via HDAC6 inhibition. Additionally, protopine exhibits antithrombotic activity by inhibiting platelet aggregation induced by agents like ADP, arachidonic acid, and PAF, primarily through suppression of thromboxane A2 synthesis. Animal studies further support its vasodilatory effects, relaxing vascular smooth muscle in rabbit aorta and mesenteric arteries by modulating calcium influx and cAMP/cGMP levels.^[38]^[5]^[39]^[32]^[40] Clinical evidence for protopine remains limited, with most data derived from studies on Corydalis yanhusuo extracts containing it; a controlled trial in humans showed that such extracts reduced pain intensity during cold pressor testing, suggesting potential efficacy for mild to moderate pain relief, including possible applications in migraine management based on preclinical nitroglycerin-induced models. In terms of drug development, protopine is considered a candidate for adjunct therapy in opioid alternatives due to its analgesic effects mediated partly through opioid receptor activation, with patents filed in the 2010s for protopine total alkaloids and derivatives aimed at enhancing bioavailability for veterinary and potential human uses. However, significant research gaps persist, including the absence of large-scale randomized controlled trials (RCTs) to confirm efficacy and safety, as well as incomplete data on long-term effects as of 2025, necessitating further clinical investigation to translate preclinical promise into approved therapies.^[41]^[42]^[40]^[20]

Safety and Toxicology

Toxicity and Side Effects

Protopine exhibits moderate acute toxicity, with an oral LD50 of approximately 313 mg/kg in mice, classifying it as toxic based on standard criteria.^[43] At high doses, symptoms include muscular weakness, severe ataxia, tremors, lethargy, convulsions, coma, and cyanosis, leading to death within 10–30 minutes in lethal exposures; autopsy findings reveal hemorrhage in the lungs, suggesting respiratory depression, along with congestion and edema in the heart, liver, kidney, and brain.^[43] Another study reports an oral LD50 of 482 mg/kg in ICR mice, with observed sedation and slowed movement as primary acute effects.^[44] Common side effects associated with protopine exposure include neurotoxic manifestations such as ataxia and lethargy, as well as gastrointestinal disturbances.^[43] Protopine demonstrates central nervous system depressant properties, which may contribute to respiratory depression at high doses.^[43] High-dose acute exposure to protopine can cause hepatotoxicity, evidenced by liver edema, vacuolar degeneration, nuclear pyknosis, and hyperemia in histopathological examinations of exposed rodents.^[43] Low-dose chronic studies (up to 48.2 mg/kg over 180 days) show no significant toxicity in rats.^[44] Regarding mutagenicity, genotoxicity assays including sperm abnormality, micronucleus, and chromosome aberration tests are negative at doses up to 241 mg/kg.^[44] Protopine is contraindicated during pregnancy due to demonstrated reproductive and embryonic developmental toxicity at doses exceeding 7.53 mg/kg, with a no-observed-effect level (NOEL) at that threshold in rodent models.^[44] As an isolated compound, protopine is not approved by the FDA for any therapeutic use. Extracts from plants like Macleaya cordata containing protopine are used in animal feed additives in some regions, but with dosage limits to avoid toxicity.^[45]

Pharmacokinetics and Metabolism

Protopine is rapidly absorbed following oral administration, with peak plasma concentrations achieved within a few hours in rat models. Studies in rats indicate an absolute oral bioavailability of approximately 25.8%, attributed to extensive first-pass metabolism in the liver rather than significant efflux inhibition by P-glycoprotein in the gut.^[46]^[3] The compound exhibits wide tissue distribution, reaching maximum concentrations in various organs including the liver (C_max ≈ 6.78 µg/mL at T_max ≈ 5.3 h) and lungs (C_max ≈ 11.42 µg/mL at T_max ≈ 5.1 h) after oral dosing in rats, suggesting higher affinity for these tissues. Protopine crosses the blood-brain barrier, enabling potential central nervous system effects.^[47]^[48] Metabolism of protopine occurs primarily in the liver through cytochrome P450 enzymes, including CYP2D1 and CYP2C11 in rats (homologous to human CYP2D6 and CYP3A4, respectively), leading to demethylation, ring cleavage, and subsequent glucuronidation or hydroxylation of metabolites. Identified metabolites include demethylated forms and those following the allocryptopine pathway, with over 10 phase I and II products detected in rat urine and feces; protopine itself undergoes rapid biotransformation, with negligible unchanged parent compound in circulation after 3 hours.^[3]^[49] Excretion is predominantly renal, with the majority of metabolites eliminated in urine within 24 hours post-administration in rats, while fecal elimination accounts for a smaller portion containing specific metabolites like demethylated derivatives; less than 1% of the dose is excreted unchanged. The elimination half-life in rats is approximately 5 hours, reflecting efficient clearance.^[3] Pharmacokinetic parameters of protopine can vary with co-administration of certain compounds sharing structural features, such as piperine, which may influence CYP2D6 activity due to the common methylenedioxyphenyl moiety, potentially altering metabolism rates. Additionally, liver function impacts disposition, as protopine exhibits hepatoprotective effects by inhibiting microsomal drug-metabolizing enzymes, though impaired hepatic metabolism could prolong exposure in disease states. Gender differences in biotransformation efficiency have been noted in rat studies, with potential implications for variability. Data on human pharmacokinetics and toxicity are limited, and further research is needed to assess clinical safety.^[50]^[40]^[3]

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