Decursin

Decursin: A Comprehensive Reference

1. Identity: Chemical and Botanical Profile

Decursin is a naturally occurring pyranocoumarin compound. It is a pyranocoumarin — a rare secondary metabolic plant product — isolated from the roots of Angelica gigas Nakai. Angelica gigas Nakai (AGN) belongs to the Angelica L. genus within the Umbelliferae family, which contains more than 60 species. Decursin exhibits anti-cancer, anti-inflammatory, and neuroprotective activities.

Its CAS registry number is 5928-25-6. Decursinol (DOH) is a direct analog of decursin (C₁₄H₁₄O₄) with MW = 246 Da, where the (CH₃)₂–C=CH–COO– side chain is replaced with a hydroxyl (–OH) group. The structures of decursin, DA, and DOH have been confirmed by UV, IR, MS, ¹H-NMR, ¹³C-NMR, and optical rotation by different research groups.

Angelica gigas is a stout plant 1 to 2 meters high with deep thick roots and a purplish, ribbed stem. The plant is a biennial that flowers in the months of July to August in dark purple umbels and self-seeds abundantly when the seeds have ripened. It is mainly distributed in the north temperate zone, especially in China, Korea, and Japan.

1.1 Related Pyranocoumarin Compounds

The pyranocoumarin compound decursin and its isomer decursinol angelate (DA) are the major chemical components in the alcoholic extracts of the root of AGN. A third closely related compound, decursinol (DOH), is both a biosynthetic precursor in the plant and the primary metabolite produced in the human liver upon oral ingestion. The attachment of a 2-methylbut-2-ene side chain results in the formation of 7-demethylsuberosin, which then undergoes cyclization to generate decursinol; subsequent modifications of decursinol give rise to its isomeric derivatives, decursin and decursinol angelate.

Pyranocoumarins are the major chemical constituents identified in the ethanolic and methanolic extracts of A. gigas. To date, decursinol (DOH), decursin (D), decursinol angelate (DA), xanthyletin, decursidin, and several related epoxy and glucosyl variants have been identified, as well as 116 volatile oil compounds including α-pinene, α-limonene, camphene, and β-eudesmol.

1.2 Common Forms and Preparations

AGN root ethanolic extracts have been marketed as dietary supplements in the United States for memory health and pain management. In the clinical trial NCT02114957, a single oral dose human pharmacokinetic study was conducted using decursin and DA delivered through an AGN-based dietary supplement called Cogni.Q; the study involved 20 healthy subjects consuming 119 mg decursin and 77 mg DA from 4 vegicapsules. Decursinol (DOH) can also be prepared semi-synthetically. A protocol to produce DOH by mild basic hydrolysis of decursin and DA has been introduced.

2. Traditional and Historical Use

Angelica gigas Nakai is a Korean plant belonging to the Angelica L. genus within the Umbelliferae family; it was found in Korean moist soil, and is recognized as a traditional medicine mainly in Korea, China, and Japan. In Korea, its root has been traditionally used as a folk medicine for the relief of menstrual pain and for anemia.

Traditionally, its dried root has been used to treat anemia, pain, infection, and articular rheumatism in Korea, most often through boiling in water to prepare the dosage forms. The root of A. gigas is most commonly prepared by decocting with water, and is used as a blood tonic, for the treatment of gynecological diseases, anti-inflammatory, analgesic, and laxative purposes.

Widely growing in many Asian countries, such as Korea, Japan, and China, the roots of this plant have been traditionally used to treat hormonal imbalance and anemia, and for liver detoxification. Angelica gigas (local name dang-gui) is also well-known as "female ginseng" due to its favorable properties in female afflictions, and has been used for centuries in Far East countries.

In traditional herbal medicine, the root of this plant is used to promote blood flow, to treat anemia, and is used as a sedative or tonic agent. The native Korean species Angelica gigas Nakai is widely used as a remedy for a variety of medical conditions including hematopoiesis, improving women's circulation, as sedatives, analgesics, and tonic.

It is important to note that the specific constituent decursin was not isolated and characterized as an individual compound in classical traditional medicine. Traditional preparations using the whole dried root or water decoctions represent the historical practice; decursin as a defined chemical entity is a product of modern phytochemical investigation.

3. Key Constituents and Active Compounds

3.1 Phytochemical Profile of Angelica gigas

Eleven monocoumarins, ten furocoumarins, eleven pyranocoumarins, nine volatile oils, nine flavonoids, and six other constituents of A. gigas have been summarized and discussed. Among these, the pyranocoumarins are considered the most pharmacologically significant fraction. Studies show that A. gigas contains pyranocoumarin compounds as major active principles, including decursin, its isomer decursinol angelate, and decursinol.

The major chemical constituents of A. gigas, decursin and decursinol angelate, have been detailed for their anti-inflammatory, anticancer, analgesic, and sedative effects. The chemical constituents of Angelica species vary depending on geographic origin. Roots of A. sinensis (Chinese dong quai) contained higher levels of ferulic acid, Z-ligustilide, and senkyunolide A, while high amounts of butylphthalide and Z-butylenephthalide were found in A. gigas roots — a distinction of practical importance for users who may confuse the two species.

3.2 Metabolism and Pharmacokinetics

First-pass hepatic metabolism of ingested decursin and DA occurs through portal vein entry to DOH by cytochrome P450 (CYP) 2C19 and 3A4 isoforms, with additional participation of hepatic carboxyesterase 2 (CES2) for decursin. The relative peak circulating level for decursin is approximately 1/10th of DA and approximately 1/1,000th of DOH in human blood. Plasma analysis in the human study revealed that men absorbed decursin and DA faster than women and reached the maximum concentration of DOH more rapidly, supporting the conversion of decursin and DA to DOH. Notably, DA conversion occurs slightly slower in humans than in rodents.

Pharmacokinetic studies after oral and intravenous administration of 10 mg/kg showed that after 8 hours, all test compounds stayed in the gastrointestinal tract at more than 1.5% of the dose, and less than 0.5% was excreted in urine. Findings have revealed that decursin expresses poor oral bioavailability, a significant limitation for clinical translation that researchers have sought to address through formulation strategies and semi-synthetic derivative development.

4. Mechanisms of Action

4.1 Anticancer Mechanisms

Decursin has pleiotropic effects in the anticancer domain, including inhibition of tumor activity, cell proliferation, angiogenesis, metastasis, and invasion, induction of apoptosis and autophagy, and also affecting immune function.

Apoptosis induction: Decursin induces cell death in melanoma B16F10 cells and breast cancer MCF-7 cells through the Bcl-2/Bax-mediated apoptosis pathway. In bladder cancer 253J and colon cancer HCT116, decursin decreases the potential of the mitochondrial membrane, makes the membranes more permeable, releases cytochrome c from the mitochondria, and activates caspase-3 to cause apoptosis.

PKC modulation: Decursin's mechanisms include protein kinase C (PKC) and ROS modulation; hypoxia-inducible factor 1α degradation; chemokine receptor CXCR7 downregulation; glutamate dehydrogenase (GDH) inhibition; reduction of the expression of cyclooxygenase-2 enzyme (COX-2); VEGFR inhibition; downregulation of CYP2A6 expression; and CYP2J2 modulation. PKC family members are serine/threonine kinases involved in signal transduction for cellular proliferation and differentiation through phosphorylation of downstream effectors.

Anti-angiogenic activity: Decursin has significant in vivo antiangiogenic effects, primarily via preventing the angiogenesis generated by vascular endothelial growth factor (VEGF) by reducing ERK and JNK activation in human umbilical vein endothelial cells (HUVECs). In multiple myeloma U266 cells, decursin regulates tumor cell viability by downregulating survivin, Bcl-2, Bcl-XL, and vascular endothelial growth factor (VEGF).

HIF-1α degradation: Decursin promotes HIF-1α degradation in A549 human non–small-cell lung carcinoma cells and in human colorectal HCT116 cancer cells under hypoxic conditions. It showed transcriptional suppression of target genes such as CXCR4 and VEGF; decursin also promoted apoptosis and decreased cell invasion.

Wnt/β-catenin pathway: Decursin, isolated from the Korean Angelica gigas root, inhibits the growth of androgen-independent human prostate cancer cells. Using a cell-based screen, researchers found that decursin attenuates the Wnt/β-catenin pathway. It antagonized β-catenin response transcription (CRT) induced by Wnt3a-conditioned medium and LiCl by promoting the degradation of β-catenin, and suppressed the expression of cyclin D1 and c-myc, downstream target genes of β-catenin, thus inhibiting the growth of PC3 prostate cancer cells.

PI3K/AKT/mTOR and JAK/STAT: Decursin shows anticancer properties through various mechanisms such as apoptosis, cell cycle arrest, inhibition of cell proliferation, autophagy, inhibition of angiogenesis, cytotoxicity, and the inhibition of invasion and migration against a number of cancers. It has the ability to affect several signaling pathways in the molecular anticancer mechanisms, such as the PI3K/AKT/mTOR, JAK/STAT, and MAPK signaling pathways.

Androgen receptor antagonism: Using activity-guided fractionation, it was discovered that decursin from AGN is an intriguing antiandrogen and androgen receptor (AR) drug that suppresses prostate-specific antigen (PSA) expression with a half-maximal inhibitory concentration (IC50) of around 0.4 μg/mL (1.3 μmol/L, 48-hour exposure). Experimentally, decursin reduced the amount of AR protein without changing the level of AR mRNA. It accomplished this by blocking androgen-stimulated AR translocation to the nucleus.

Immune microenvironment: Decursin enhances CD8+ T cell infiltration within the tumor microenvironment while inhibiting PD-L1 expression and immunosuppressive cell populations such as regulatory T cells.

4.2 Neuroprotective Mechanisms

In mice, decursin dramatically reduced scopolamine-induced amnesia as assessed by the Morris water maze and passive avoidance tests. The findings suggested that decursin might have anti-amnestic effects by reducing acetylcholinesterase (AChE) activity in mice's hippocampal regions. In amyloid β-induced neurotoxicity in PC12 cells, decursin greatly reduced cytotoxicity and lipid peroxidation, and enhanced glutathione levels and antioxidant enzyme activities. Moreover, decursin promoted Nuclear factor erythroid 2-related factor 2 (Nrf2) expression in PC12 cells and inhibited Aβ aggregation.

4.3 Anti-inflammatory Mechanisms

Research has demonstrated that decursinol angelate can reduce the activity of the Akt and NF-κB signaling pathways, and that decursin has the potential to treat sepsis. In the context of joint disease, decursin (DE), the major active component isolated from Angelica gigas Nakai, has been demonstrated to possess an anti-inflammatory effect in many diseases. In vitro cell experiments show the inflammatory response in chondrocytes is mediated via interleukin-1β (IL-1β), which leads to abnormal secretion of pro-inflammatory factors such as prostaglandin E2 (PGE2), interleukin-6 (IL-6), tumor necrosis factor alpha (TNF-α), COX-2, nitric oxide (NO), and inducible nitric oxide synthase (iNOS).

5. Scientific Evidence by Area of Use

5.1 Oncology

Scope of in vitro and animal evidence: Decursin exhibits anti-cancer effects across a wide spectrum of malignancies, including pancreatic, cervical, gastric, colorectal, prostate, liver, esophageal, head and neck, brain (glioblastoma), ovarian, non-small-cell lung, and inflammation-associated colorectal and skin cancers, B-cell lymphoma, FLT3-ITD acute myeloid leukemia, and hypoxia-driven tumors, underscoring its broad potential as a multi-targeted therapeutic agent.

Evidence strength — in vitro: The in vitro anti-tumor activities of decursin and/or DA against prostate cancer, lung cancer, breast cancer, colon cancer, bladder cancer, sarcoma, myeloma, and leukemia have been increasingly reported in the past decade, whereas the in vivo efficacy in mouse models was established only for a few organ sites.

Prostate cancer (preclinical): The anticancer properties of decursin were investigated in vivo and in vitro in B16F10 cells, which were shown to decrease the proliferation of B16F10 cells, but not of normal cells, in a dose-dependent manner. The anti-cancer activity of AGN alcoholic extract has been established in a number of animal cancer models, including a transgenic model of prostate carcinogenesis.

Osteosarcoma (preclinical): Decursin increased the number of cells in the G0/G1 phase and decreased in the S-phase on human osteosarcoma cell lines at 24 hours. Decursin also inhibited the Akt pathway by suppressing the phosphorylation of Akt. The increasing tumor volume was suppressed in the decursin-administered group with further suppression in combination with cisplatin compared to sole cisplatin administration. The decrease in renal function and renal epithelial cell damage caused by cisplatin was improved by the combinatorial treatment with decursin.

Melanoma (preclinical): Treatment with decursin inhibited cell proliferation in a dose-dependent manner in B16F10 cells, but not in normal cells. Decursin also induced apoptosis in B16F10 cells, as determined by annexin V-staining assay and TUNEL staining assay.

Clinical translation status: A second clinical trial was approved (NCT05375539). The Phase I study is entitled "Angelica herbal supplement Angelica gigas Nakai–CognI.Q acute dose safety and pharmacokinetics dose-response in prostate cancer patients (PK Dose Trial)" and aims to obtain acute dose safety and PK/PD data in a dose-response design. The trial's primary endpoint is maximum tolerated dose determination, with secondary endpoints including pharmacokinetic metrics, CYP 2C19 and 3A4 metabolizer genotype status, natural killer cell counts, inflammatory and immunological cytokines as potential pharmacodynamic markers. No completed Phase II or III efficacy trials for any cancer indication have been published at the time of this writing. The anticancer evidence for decursin remains at the preclinical (cell culture and animal model) stage.

5.2 Cognitive Function and Neuroprotection

Animal and in vitro evidence: Scopolamine-induced cognitive dysfunction was significantly attenuated by a single or sub-chronic administration of INM-176 (an AGN extract) in the passive avoidance and the Morris water maze tasks. A single or sub-chronic administration also ameliorated memory impairments induced by Aβ_1–42 protein. INM-176 inhibited acetylcholinesterase activity in the hippocampal tissue in vitro and ex vivo.

Decursin displays neuroprotective effects against amyloid β_25–35-induced neurotoxicity in rat pheochromocytoma PC12 cells via suppressing mitochondrial apoptotic processes.

Cerebrovascular model: Angelica gigas Nakai root contains decursin which exerts beneficial properties such as anti-amnesic and anti-inflammatory activities. A study in a gerbil transient ischemia model examined whether post-treatment with decursin and the root extract could protect against neuronal damage and BBB leakage. The major objective was to investigate protective effects in neuronal damage and spatial and learning memory impairment in gerbil hippocampus when the extract and decursin were therapeutically administered after transient ischemia in the forebrain. Furthermore, the study examined transient ischemia-induced changes in BBB integrity and leakage along with the alteration of astrocyte endfeet in the hippocampus.

Evidence strength: All neuroprotective and cognitive data for decursin specifically are from preclinical models (rodent behavioral tests, cell culture). No controlled human clinical trials have evaluated decursin's cognitive or neuroprotective efficacy as a primary endpoint. AGN root ethanolic extract dietary supplements are marketed in the United States for memory health and pain management. This marketing precedes clinical trial confirmation of efficacy.

5.3 Inflammation and Pain (Analgesic Activity)

Both in vitro and in vivo studies have demonstrated that decursin has potential neuroprotective, anti-inflammatory, anti-melanogenic, anti-angiogenic, and antioxidant activities. The major chemical constituents of A. gigas, decursin and decursinol angelate, have been detailed for their anti-inflammatory, anticancer, analgesic, and sedative effects.

Evidence strength: Anti-inflammatory and analgesic claims for decursin are supported by in vitro mechanistic studies and animal models, but no published randomized controlled trials in humans have tested pain or inflammation as primary endpoints. The U.S. supplements market reflects traditional use and preclinical data rather than confirmed human trial outcomes.

5.4 Osteoarthritis

One in vitro study specifically examined decursin in chondrocytes. The object of the study was to assess the therapeutic effect of decursin on osteoarthritis and explore its potential anti-inflammatory mechanisms. In vitro, the inflammatory response in chondrocytes mediated by IL-1β led to abnormal secretion of pro-inflammatory factors such as PGE2, IL-6, TNF-α, COX-2, NO, and iNOS. Decursin was found to suppress these mediators through the PI3K-Akt and NF-κB pathways. This evidence is limited to cell culture; no human osteoarthritis trials with decursin have been reported.

5.5 Other Investigated Areas (Preclinical Only)

Reviewed in vivo medicinal activities of AGN and/or its pyranocoumarins and furanocoumarin nodakenin include findings in models of cancer, pain, memory loss, cerebral ischemia-reperfusion stroke, metabolic syndrome and vascular endothelial dysfunction, anxiety, sleep disorder, epilepsy, inflammatory bowel disease, osteoporosis, and osteoarthritis. All these represent areas of ongoing preclinical investigation; human clinical trials for most of these indications had not been completed or published at the time of this writing.

Epilepsy: Decursin is able to attenuate kainic acid-induced seizures and could have potential as an antiepileptic drug — evidence that is, as of current published literature, confined to animal models.

Hepatoprotection: Decursin exhibits hepatoprotective effects, potentially by inhibiting the TGF-β1–induced NOX activation and Smad signaling.

6. Body Systems and Health Areas

• Oncology / Cell Biology: Decursin has gained significant attention as a potent antitumor agent owing to its substantial inhibitory effects on cancer progression and low toxicity in normal tissues.
• Nervous System: Preclinical support for anti-amnestic activity via AChE inhibition in hippocampal tissue, protection against amyloid-beta neurotoxicity, and ischemia-reperfusion neuroprotection.
• Endocrine / Reproductive: Stabilizing the side chain composition of decursin has been suggested as a viable and promising strategy to increase its in vivo anti-androgen receptor activity. Traditional gynecological uses for menstrual pain and hormonal balance are consistent with this anti-androgenic profile.
• Musculoskeletal System: In vitro evidence for anti-inflammatory effects in chondrocytes; preclinical activity in osteosarcoma models with cisplatin combination.
• Cardiovascular / Angiogenic: Decursin and decursinol inhibit VEGF-induced angiogenesis by reducing the activation of ERK and JNK in HUVECs, and possess potent in vivo anti-angiogenic activity, coupled with the advantage of oral dosing.
• Immune System: Preclinical data on enhancement of bacterial killing by macrophages and modulation of the tumor immune microenvironment.
• Gastrointestinal: Another study indicated that treatment with AGN extract mitigated weight loss, lowered disease activity index scores, and reduced colon reduction in mice with dextran sulfate sodium-triggered ulcerative colitis.

7. Dosage Forms and Doses Reported in Studies

No internationally recognized therapeutic dosage for decursin has been established by any regulatory or pharmacopeial authority. The following dosages are those reported in published human or preclinical research, reported here solely as found in those sources.

7.1 Human Pharmacokinetic Study (the Only Published Human Trial)

In the clinical trial NCT02114957, researchers conducted a single oral dose human pharmacokinetic study of decursin and DA delivered through an AGN-based dietary supplement Cogni.Q. The study involved 20 healthy subjects — 10 men and 10 women — each consuming 119 mg decursin and 77 mg DA from 4 vegicapsules.

For decursin, decursinol angelate, and decursinol, the estimated mean area under the curve (AUC_0–48h) was 37,335 and 27,579 h nmol/L, correspondingly.

7.2 Preclinical In Vitro and Animal Dosages

In preclinical in vitro experiments, concentrations of 10 μM, 20 μM, and 40 μM have been used. Time-course experiments with decursin concentration maintained at 10 μM demonstrated progressive downregulation of both TP63 and SOX-2 proteins at 24, 48, and 72 hours post-treatment. Dose–response analysis with treatment duration fixed at 24 hours revealed concentration-dependent reduction in these oncoproteins at 10, 20, and 40 μM of decursin.

In a Lewis lung carcinoma murine model, decursin was administered at 10 mg/kg (as cited by the 2024 PMC review from Sestito et al.). For pharmacokinetic studies in rodents, oral and intravenous administration of 10 mg/kg has been a standard experimental dose. Pharmacokinetic studies after oral and intravenous administration of 10 mg/kg showed that after 8 hours all test compounds stayed in the gastrointestinal tract at more than 1.5% of the dose and less than 0.5% was excreted in urine.

7.3 Phase I Dose-Escalation Trial (Ongoing/Approved)

A second clinical trial (NCT05375539) was approved. The Phase I study aims to obtain acute dose safety and pharmacokinetic/pharmacodynamic data in a dose-response design in prostate cancer patients. Results from this trial were not published at the time of this writing.

8. Safety Considerations and Drug Interactions

8.1 Observed Safety in the Human Pharmacokinetic Trial

Considering safety, all 20 participants tolerated the dietary supplement CognI.Q extremely well. For the first 48 hours, none of the subjects experienced any treatment-related side effects, such as fever, discomfort, nausea, or rash. Vital signs were taken and recorded pre-dose at hour 0 and post-dose at hours 1, 5, 8, 12, 24, and 48. Additional blood samples collected at hours 0 (baseline) and 24 were tested for hepatic function panel, blood urea nitrogen (BUN) and creatinine panel (renal function), and CBC by a College of American Pathologists–certified clinical laboratory. On the 30th day post-dose, all participants were contacted by telephone for follow-up adverse event assessments.

8.2 Normal Cell Selectivity

Decursin showed no toxic effects on normal human cell lines. By modulating COX-2 and survivin, decursin induces an apoptotic process that is safe for human peripheral blood lymphocytes but detrimental to leukemia cells. Decursin did not produce retinal toxicity at concentrations up to 50 μmol/L, which is five times the therapeutically effective value, implying that it can be used to treat retinopathy without putting the retina or healthy retinal vessels at risk.

8.3 CYP Enzyme Inhibition and Drug Interaction Risk

This is a documented, source-backed concern. Decursin, DA, and DOH are reported to inhibit not only CYP2A6 and CYP2J2 activity, but also CYP1A2, thus impeding the first-pass metabolism of drugs that are substrates of the corresponding CYP isoforms. Decursin, used as a traditional Asian medicine, is a typical substrate of CYP1A2 enzyme.

Decursin also inhibits CYP2J2. In 2013, the main substance decursin, decursinol angelate, the ether form (JH714), and epoxide decursin were analyzed in vitro and in vivo. CYP isoforms were inhibited more than 50%. The inhibition of CYP isoforms carries theoretical risk of pharmacokinetic drug–drug interactions when decursin or AGN extracts are co-administered with pharmaceutical drugs that depend on these enzymes for metabolism. The clinical magnitude of this risk in humans at supplement doses has not been formally characterized.

8.4 Limitations of Safety Data and Evidence Gaps

Further studies are still needed to assess the genotoxicity and reproductive toxicity of decursin, among others, in order to support anticancer studies. Published data support the similarity of metabolic fate of decursin and DA in humans and rodents, with suggestion of a potential slower metabolism of DA in humans than in rodents. One limitation of the human pharmacokinetic study was that dietary supplement Cogni.Q was not the ideal form for a pharmacokinetic study of decursin and DA, and the small number of subjects was another recognized limitation.

8.5 Cytotoxicity Toward Normal Cells

One study has noted a nuance in normal cell toxicity. Decursin was also cytotoxic against normal cells under some tested conditions — a finding that stands in partial contrast to the more selective toxicity observed in most published work, and underscores the importance of concentration-dependent assessments.

9. Evidence Summary and Current Research Status

The anticancer, analgesic, pro-memory, and other bio-activities of AGN extract and its signature phytochemicals decursin, decursinol angelate, and decursinol were comprehensively reviewed over a decade ago and have been periodically updated. In the last decade, significant progress has been made in understanding the pharmacokinetics and metabolism of these compounds in animal models, and single-dose human pharmacokinetic studies have been published.

In addition to increased knowledge of the known bioactivities, new bioactivities with potential novel health benefits have been reported in animal models of cerebral ischemia/stroke, anxiety, sleep disorder, epilepsy, inflammatory bowel disease, sepsis, metabolic disorders, osteoporosis, and osteoarthritis.

The scientific evidence base for decursin is characterized by extensive in vitro mechanistic data and a growing body of animal model studies, one published human single-dose pharmacokinetic trial in 20 healthy subjects (NCT02114957), and one Phase I dose-escalation trial in cancer patients (NCT05375539) whose results have not been published. Based on data analysis from available literature, decursin has properties to be considered as a potential candidate in the treatment of cancer. However, more clinical research is suggested to establish proper efficacy and safety. All therapeutic efficacy claims at this stage are preliminary and not validated by completed human clinical trials with defined efficacy endpoints.

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