Xanthorrhizol

Xanthorrhizol

1. Identity and Chemical Characterization

Xanthorrhizol (chemical name: 2-methyl-5-[(2R)-6-methylhept-5-en-2-yl]phenol) is a phenolic bisabolane sesquiterpenoid that appears as a colorless oil with an aromatic ring and a side chain with isoprene and hydroxyl groups. Its molecular formula is C₁₅H₂₂O. The compound is commonly abbreviated in the scientific literature as XNT or XTZ.

Xanthorrhizol is a bisabolane-type sesquiterpenoid compound extracted from Curcuma xanthorrhiza Roxb. It is abundantly present in that plant, together with curcumin, in particular in the essential oil of the rhizomes. Xanthorrhizol is the most abundant component (31.9%) of the essential oil of C. xanthorrhiza.

Xanthorrhizol has also been identified in the rhizomes of other Curcuma species, such as C. aromatica, C. longa, C. aeruginosa, and C. angustifolia. However, the presence of xanthorrhizol in C. xanthorrhiza is species-dependent, distinguishing C. xanthorrhiza (Temulawak) from C. longa (turmeric).

Parent Plant

C. xanthorrhiza, known as Java turmeric or temulawak (Bahasa), belongs to the family Zingiberaceae. It is widely distributed in the Java island of Indonesia, Malaysia, and Thailand and sparsely occurs in China and India. In Indonesia, this plant is widespread and cultivated in almost all major islands such as Java, Sumatra, Kalimantan, Sulawesi, and Maluku. C. xanthorrhiza has also been cultivated in several Southeast Asian countries such as Malaysia, Thailand, the Philippines, and Vietnam.

Common Preparations and Forms

Traditionally, C. xanthorrhiza rhizome is usually consumed in the form of fresh plant, decoction, steeping, powder, and even as food. The rhizomes are harvested, dried, and typically extracted using ethanol or processed to isolate specific compounds like xanthorrhizol through chromatography. Industrially, the semi-finished product from the rhizome of C. xanthorrhiza is simplicia, starch, essential oil, and extract.

2. Traditional and Historical Use

Curcuma xanthorrhiza Roxb., locally known as Temulawak, has been extensively utilized in Indonesia as a medicinal and nutritional plant since immemorial time. The rhizome of this plant is an important ingredient. Traditionally, C. xanthorrhiza has been greatly harnessed all over its local distribution area as an ingredient of jamu (Indonesian herbal supplement and medicine) or to medicate and control numerous sicknesses and disorders since ancient times.

In Indonesia, C. xanthorrhiza is a very well-known herb and has been widely applied by various tribes to treat various diseases. Some traditional uses include overcoming lack of appetite, constipation, hemorrhoid, acne, diarrhea, and seizures, as well as destroying gallstones, treating kidney and liver diseases, rheumatic pain, rheumatism, and arthritis, and treating thrush and vaginal discharge.

C. xanthorrhiza (Temulawak) has also been exported and utilized in Europe at least since 1963, particularly for the treatment of dyspepsia, infections, and skin and liver illness.

Traditionally, C. xanthorrhiza is widely used for the treatment of different health conditions, including common fever, infection, lack of appetite, fatigue, liver complaints, and gastrointestinal disorders. The rhizome has also been used to treat inflammation in postpartum uterine bleeding.

Within Indonesia, C. xanthorrhiza (Temulawak or Javanese turmeric) has several regional names such as koneng gede (Sundanese), temu labak (Madurese), tommo (Bali), tommon (South Sulawesi), and karbanga (Ternate).

3. Key Constituents and Phytochemistry

To date, over 40 active compounds, including terpenoids, curcuminoids, and other phenolic compounds, have been isolated and identified from C. xanthorrhiza Roxb. Among these chemicals, curcuminoids and terpenoids are the majority, and they own essential biological properties. Based on various studies, the majority in the quantity of the secondary metabolites obtained from the essential oil of C. xanthorrhiza rhizome is xanthorrhizol.

Other medicinally important constituents of this plant are curcumene, curzerenone, and turmerone. The extract also contains other bioactive compounds, such as curcuminoids, camphor, geranyl acetate, zerumbone, β-curcumene, zingiberene, and ar-curcumene, as well as xanthorrhizol.

4. Mechanisms of Action

Xanthorrhizol is a potential suppressor of carcinogenesis. Seeing that several monophenolic groups possess cytotoxic activities, the cytotoxic effect of xanthorrhizol may be contributed by its phenol group. Its anticancer mechanisms are comprehensive and diverse by modulating different levels of cellular growth and apoptosis.

In vitro and in vivo studies showed that xanthorrhizol targets different kinases, inflammatory cytokines, apoptosis proteins, and transcription factors, leading to the suppression of angiogenesis, metastasis, and the activation of apoptosis and cell cycle arrest.

The peer-reviewed literature (summarized in the 2015 Cancer Cell International review) documents the following specific mechanisms for xanthorrhizol:

• Anti-inflammatory: In vitro, xanthorrhizol reduced COX-2, iNOS, TNF-α, and IL-6 levels; in vivo it counteracted the effect of TPA-induced ODC, COX-2, and iNOS activation in mouse skin, and prevented IκBα degradation; it also blocked the neurogenic and inflammatory pain response in the formalin-induced pain test in rats.
• Antioxidant: Xanthorrhizol suppressed H₂O₂-induced lipid peroxidation in rat brain homogenates, attenuated glutamate-induced neurotoxicity and ROS production, and inhibited human LDL peroxidation.
• Antihyperglycemic: Reduced the levels of insulin, glucose, free fatty acids (FFA), and triglycerides (TG) in serum; reduced the size of epididymal fat pad and adipocyte; decreased the production of TNF-α, IL-6, IL-1β, and CRP in adipose tissue, liver, and muscle.
• Antihypertensive: Demonstrated calcium antagonistic activity in rat uterus and thoracic aorta.
• Antiplatelet: Inhibited platelet aggregation stimulated by arachidonic acid, collagen, and ADP.
• Nephroprotective and hepatoprotective: Attenuated JNK phosphorylation involved in MAPK signaling in cisplatin-treated models.

The hepatoprotective effect is partly attributed to phenolic compounds in the extract that possess antioxidant and anti-inflammatory properties. Moreover, xanthorrhizol's ability to regulate DNA-binding activities of transcription factors NF-κB and AP-1 may be a potential mechanism to explain its preventive effect on hepatotoxicity.

The antioxidant properties of xanthorrhizol contribute to its neuroprotective and LDL oxidation inhibitory effects.

Regarding hormonal activity, xanthorrhizol has been studied as a phytoestrogen in vitro. It may exert both estrogenic and anti-estrogenic effects on human metabolism, depending on xanthorrhizol and endogenous estrogen concentration, gender, and menopausal status.

5. Scientific Evidence by Area of Use

5.1 Anticancer Activity

Studies show that xanthorrhizol has preventive and therapeutic activities against different types of cancer, including breast, cervical, colon, liver, lung, oral and esophageal, and skin cancers. Xanthorrhizol regulates multiple signaling pathways that block carcinogenesis and proliferation.

Breast Cancer (In Vitro): Xanthorrhizol is a natural sesquiterpenoid compound isolated from the rhizome of Curcuma xanthorrhiza Roxb. It was tested for antioxidant and anti-inflammatory activities. An antiproliferation assay using the MTT method indicated that xanthorrhizol inhibited the proliferation of the human breast cancer cell line MCF-7 with an EC₅₀ value of 1.71 μg/mL. These results suggest that xanthorrhizol has antiproliferative effects on MCF-7 cells by inducing apoptosis through the modulation of Bcl-2, p53, and PARP-1 protein levels.

Breast Cancer (Combined Treatment, In Vitro): One study evaluated whether the combination of xanthorrhizol and curcumin might show synergistic growth inhibitory effects toward MDA-MB-231 human breast cancer cells via apoptosis induction. The effective dose that produced 50% growth inhibition (GI₅₀) was calculated from the log dose-response curve of fixed combinations of xanthorrhizol and curcumin. The investigations showed that xanthorrhizol was able to induce apoptotic cell death in the MDA-MB-231 cell line.

Cervical Cancer (In Vitro): An antiproliferative assay using methylene blue staining revealed that xanthorrhizol inhibited the proliferation of the cervical cancer cell line HeLa with an EC₅₀ value of 6.16 μg/mL. Xanthorrhizol significantly increased apoptosis in HeLa cells, as evaluated by the TUNEL assay and nuclear morphology by Hoechst 33258 staining. Western blot analysis implied an upregulation of tumor suppressor protein p53 and the pro-apoptotic protein Bax following treatment with xanthorrhizol. Xanthorrhizol, however, did not affect the expression of the anti-apoptotic protein Bcl-2 and the viral oncoprotein E6. Hence, xanthorrhizol is considered a promising antiproliferative and anticancer agent that induces p53- and Bax-dependent apoptosis in HeLa cervical cancer cells.

Colon Cancer (In Vitro): Xanthorrhizol dose-dependently exerted antiproliferative effects against HCT116 human colon cancer cells. Xanthorrhizol also arrested cell cycle progression in the G0/G1 and G2/M phase and induced the increase of sub-G1 peaks. Cell cycle arrest was highly correlated with the downregulation of cyclin A, cyclin B1, and cyclin D1; cyclin-dependent kinase 1 (CDK1), CDK2, and CDK4; proliferating cell nuclear antigen; and inductions of p21 and p27, cyclin-dependent kinase inhibitors. The apoptosis by xanthorrhizol was markedly evidenced by induction of DNA fragmentation, release of cytochrome c, activation of caspases, and cleavage of poly-(ADP-ribose) polymerase.

Anti-Metastatic Activity (In Vitro / In Vivo): In previous studies, xanthorrhizol suppressed cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) expression, inhibited cancer cell growth, and exerted an anti-metastatic effect in an animal model. A 2024 study in Planta Medica specifically investigated (R)-(−)-xanthorrhizol in triple-negative breast cancer (TNBC). The study aimed to investigate the antimigratory and anti-invasive properties, as well as the possible molecular mechanisms behind them, and demonstrated significant inhibitory effects on MDA-MB-231 cell migration and invasion.

Evidence Strength: All anticancer findings for xanthorrhizol to date are based on in vitro (cell-line) and in vivo animal model studies. As of the most recent comprehensive reviews, no clinical study of xanthorrhizol in cancer has been reported. The evidence base is therefore preliminary and cannot be extrapolated to human clinical outcomes without further investigation.

5.2 Antimicrobial Activity

Antibacterial (In Vitro): The antibacterial activity of xanthorrhizol, isolated from the methanol extract of Curcuma xanthorrhiza roots, was evaluated against oral microorganisms in comparison with chlorhexidine.

Dental Caries Prevention (Systematic Review): A systematic review published in Drug Design, Development and Therapy (2021) searched PubMed, Scopus, and Embase through September 2020 for studies examining the antibacterial and antimicrobial effects of xanthorrhizol in the prevention and treatment of dental caries. Eleven studies met the criteria for final inclusion. Findings showed that xanthorrhizol showed significant inhibition of notable caries-causing bacteria including Streptococcus mutans, Streptococcus sanguinis, Enterococcus faecalis, and Bacillus cereus. Furthermore, there was no reported toxicity. However, it could not selectively target the growth of cariogenic bacteria.

Studies exploring the use of xanthorrhizol as a potential drug for the prevention and treatment of dental caries have shown promising outcomes. However, more work needs to be done, especially in areas such as optimal dose or concentration; in vitro, in vivo, and clinical studies; and selective targeting of cariogenic bacteria.

Antifungal / Anticandidal (In Vitro): Xanthorrhizol was investigated for its anticandidal activity using six Candida species. In vitro susceptibility tests were carried out in terms of MIC and minimal fungicidal concentration (MFC). All Candida species showed susceptibility to xanthorrhizol in the MIC range 1.0–15.0 mg/L for Candida albicans, 1.0–10 mg/L for Candida glabrata, 2.0–8.0 mg/L for Candida guilliermondii, 2.5–7.5 mg/L for Candida krusei, 2.5–25 mg/L for Candida parapsilosis, and 2.0–8.0 mg/L for Candida tropicalis.

These results support the potential use of xanthorrhizol as an anticandidal agent, and it can be used complementarily with other conventional antifungal agents. Research showed that xanthorrhizol isolated from the rhizome of Java turmeric showed significant antifungal activity.

Evidence Strength: Antimicrobial evidence for xanthorrhizol is derived entirely from in vitro studies. The systematic review (2021) that pooled eleven studies confirmed inhibitory activity against oral cariogenic bacteria but noted the absence of clinical trials and the lack of selectivity for pathogenic organisms over commensal bacteria.

5.3 Anti-Inflammatory Activity

C. xanthorrhiza rhizome extracts have been used in traditional medicines as analgesic and anti-inflammatory agents. Preclinical evidence suggests xanthorrhizol inhibits key pro-inflammatory mediators. In prior studies, xanthorrhizol suppressed cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) expression. From the perspective of anti-inflammatory pharmacological activities, xanthorrhizol inhibits both pain response and inflammatory response.

In a study using three rodent pain models, standardized C. xanthorrhiza ethanolic extract did not show significant analgesic effect in the hot plate and tail flick tests. However, in the formalin-induced pain test, C. xanthorrhiza ethanolic extract significantly (P < 0.05) suppressed the paw licking time of rats in both early and late phases at doses of 200 and 400 mg/kg of the extract, respectively.

Evidence Strength: Anti-inflammatory and analgesic evidence is limited to in vitro mechanistic studies and in vivo animal models. No clinical trials in human subjects have been identified assessing xanthorrhizol specifically for inflammatory conditions.

5.4 Antidiabetic / Antihyperglycemic Activity

A study published in Evidence-Based Complementary and Alternative Medicine (PMC, 2014) examined the antihyperglycemic and anti-inflammatory effects of standardized Curcuma xanthorrhiza extract (CXE) and its active compound xanthorrhizol (designated XAN) in high-fat diet-induced obese mice. Xanthorrhizol and CXE treatments significantly attenuated the HFD-induced hyperglycemic, insulin-resistant, and chronic low-grade systemic inflammatory states in obese mice. Xanthorrhizol and CXE treatments effectively improved serum levels of insulin, glucose, FFA, and TG. In addition, treatment decreased epididymal fat pad mass by reducing adipocyte size and liver fat accumulation. Overall, these results suggest that xanthorrhizol and CXE, with their antihyperglycemic and anti-inflammatory activities, might be used as potent antidiabetic agents for the treatment of type 2 diabetes.

Evidence Strength: Antidiabetic evidence is limited to in vivo animal studies (high-fat diet obese mouse model). No human clinical trials have been identified. The evidence is preliminary.

5.5 Hepatoprotective Activity

Nephroprotective and hepatoprotective effects of xanthorrhizol have been studied in male ICR mice treated with cisplatin. Cisplatin is a potent chemotherapeutic drug, but the occurrence of nephrotoxicity has become the main limitation of cisplatin-based chemotherapy. Xanthorrhizol exhibited a nephroprotective effect by attenuating the increased specific gravity of the kidney induced by cisplatin.

Evidence Strength: Hepatoprotective and nephroprotective findings are from animal models only, specifically using cisplatin-induced organ damage. No human clinical data are available.

5.6 Antioxidant Activity

The methanol extracts and rhizome oils of C. xanthorrhiza showed strong inhibitory activity on copper-mediated oxidation of LDL. Curcumin, demethoxycurcumin, and bisdemethoxycurcumin isolated from the methanol extracts exhibited stronger activity than probucol (IC₅₀ value 0.57 μmol/L) as reference, with IC₅₀ values ranging from 0.15 to 0.33 μmol/L. Xanthorrhizol, the most abundant component (31.9%) of the oil of C. xanthorrhiza, showed relatively strong activity with an IC₅₀ value of 1.93 μmol/L.

Evidence Strength: LDL antioxidant evidence is based on in vitro human LDL assay data. No clinical antioxidant trials specific to xanthorrhizol have been identified.

5.7 Antiplatelet Activity

In vitro antiplatelet activity of xanthorrhizol at 100 µg/mL showed strong inhibition toward platelet aggregation stimulated by arachidonic acid (100%), collagen (81.3%), and adenosine diphosphate (ADP) (78.6%) in human whole blood. Although previous studies reported that the antiplatelet activity of curcumin was higher than xanthorrhizol, the potential of xanthorrhizol as an antiplatelet compound should not be neglected. Its antiplatelet mechanism requires further investigation.

Evidence Strength: This is an in vitro finding using human whole blood. No in vivo or clinical studies of xanthorrhizol's antiplatelet effects have been identified.

5.8 Antihypertensive Activity

The detailed antihypertensive activities and mechanisms of xanthorrhizol are yet to be elucidated. Preclinical evidence points to a calcium antagonistic mechanism, but no clinical studies exist.

6. Body Systems and Health Areas

Based on the peer-reviewed literature, xanthorrhizol has been studied in relation to the following body systems and health areas:

• Oncology: Multiple cancer cell lines including breast, cervical, colon, liver, lung, oral, esophageal, and skin.
• Oral Health / Dentistry: Prevention of dental caries via inhibition of cariogenic oral bacteria; antibacterial activities against Lactobacillus sp., Porphyromonas gingivalis, and Streptococcus sp.
• Gastrointestinal System: Xanthorrhizol also acts as a remedial agent for gastrointestinal and constipation-related disorders.
• Metabolic / Endocrine: Blood glucose regulation, insulin resistance, adipose tissue, and lipid metabolism in preclinical models.
• Hepatic and Renal Systems: Protection against drug-induced hepatotoxicity and nephrotoxicity in animal studies.
• Cardiovascular System: Antiplatelet and antihypertensive activities in preclinical models.
• Neurological System: Neuroprotective effects based on in vitro suppression of glutamate-induced neurotoxicity and ROS production.
• Immune and Inflammatory System: Suppression of NF-κB, COX-2, iNOS, and pro-inflammatory cytokines.
• Endocrine / Hormonal: Phytoestrogenic and anti-estrogenic activity in vitro.

7. Dosage Forms and Doses Reported in Studies

No established human clinical dosage has been determined for xanthorrhizol as an isolated compound, as clinical studies of xanthorrhizol are not available so far. The following dosages and concentrations are reported in preclinical research only:

• In a cervical cancer cell line study, xanthorrhizol inhibited proliferation of HeLa cells with an EC₅₀ of 6.16 μg/mL.
• In an MCF-7 breast cancer cell line study, xanthorrhizol inhibited cell proliferation with an EC₅₀ value of 1.71 μg/mL.
• In vitro antiplatelet studies used xanthorrhizol at a concentration of 100 µg/mL in human whole blood.
• Anticandidal MIC values ranged from 1.0–15.0 mg/L for Candida albicans across different isolates.
• In rodent analgesic models, the active dose for the extract (standardized C. xanthorrhiza ethanolic extract) was 200 and 400 mg/kg in both early and late phases of the formalin test.
• Animal safety studies showed that the aqueous extract of C. xanthorrhiza at up to 2 g/kg body weight orally did not demonstrate any signs of toxicity in mice or rats. The ethanolic extract of C. xanthorrhiza containing 0.1238 mg of xanthorrhizol per mg showed no toxic effect in mice until a dose of 5 g/kg body weight.

8. Safety Considerations and Interactions

8.1 Preclinical Toxicology

In acute oral toxicity studies, standardized Curcuma xanthorrhiza ethanolic extract showed no mortality in mice at doses up to 5 g/kg. There were no toxicity signs observed on the skin, fur, or eyes of the animals, and no noticeable behavioural changes in salivation, sleeping pattern, diarrhea, or lethargy were found in treated animals. This result indicates that the Curcuma xanthorrhiza ethanolic extract is non-toxic and safe at 300 mg/kg, 2,000 mg/kg, and 5,000 mg/kg.

In a multi-herb formulation containing C. xanthorrhiza, the acute oral toxicity assay showed that there was no toxic syndrome and mortality found during the period of the experiment. The lethal dose (LD₅₀) was more than 5,000 mg/kg, which was categorized as practically non-toxic.

8.2 Gaps in Toxicological Data

In vivo rodent pharmacokinetic and pharmacodynamic studies of xanthorrhizol should be conducted to ensure it has appropriate properties to be investigated in clinical pharmacology and safety studies. As of the most recent published review, no information is available about genotoxicity, carcinogenicity, and reproductive toxicity of xanthorrhizol; future studies on these areas would contribute important knowledge to the community.

8.3 Herb–Drug Interactions

Xanthorrhizol showed synergistic antifungal effects with amphotericin B and ketoconazole in vitro. This is a pharmacodynamic interaction observed only in laboratory conditions, and its clinical relevance is not established.

One study investigated the herb–drug interaction of xanthorrhizol and tamoxifen in human breast cancer cells. Using the MCF-7 cell line as an in vitro model, the interaction between xanthorrhizol and tamoxifen was measured by MTT assay, luciferase reporter assay, and cell cycle analysis. When MCF-7 cells were co-treated with tamoxifen and xanthorrhizol, there were no significant changes in terms of cell number, luciferase activity, percentage S-phase cells, and LC3-II expression. However, using the MCF-7-implanted nude mice model, it was possible to detect significantly increased tumor volumes, a larger tumor size, and increased protein expression of P38 and P27(Kip1) in the xanthorrhizol + tamoxifen group compared to the tamoxifen-alone group. It can be concluded that while there is no significant herb–drug interaction between xanthorrhizol and tamoxifen in vitro, there is such an interaction in tumor-bearing mice, which provides important information that affects breast cancer treatment translational research.

8.4 Hormonal and Estrogenic Considerations

Studies on xanthorrhizol's phytoestrogenic properties indicate that estrogen should not be excluded in experimental conditions. Xanthorrhizol may exert both estrogenic and anti-estrogenic effects on human metabolism, depending on xanthorrhizol and endogenous estrogen concentration, gender, and menopausal status. The clinical implications of this dual hormonal modulation have not been characterized in human studies.

8.5 Antiplatelet Precautions

Given xanthorrhizol's demonstrated in vitro inhibition of platelet aggregation stimulated by arachidonic acid, collagen, and ADP at 100 µg/mL, potential interactions with anticoagulant and antiplatelet medications are a theoretical concern, though this has not been investigated in clinical settings.

9. Overall Assessment of Evidence

Xanthorrhizol has been well established to possess a variety of biological activities such as anticancer, antimicrobial, anti-inflammatory, antioxidant, antihyperglycemic, antihypertensive, antiplatelet, nephroprotective, hepatoprotective, estrogenic and anti-estrogenic effects. However, the current body of evidence consists overwhelmingly of in vitro and animal studies. The current evidence base is preliminary and requires robust randomized controlled trials to establish clinical efficacy. Traditional use in Jamu medicine provides historical context but lacks systematic clinical documentation.

It is recommended that in vivo rodent pharmacokinetic and pharmacodynamic studies of xanthorrhizol be conducted to ensure appropriate properties for investigation in clinical pharmacology and safety studies. Since no information is available on genotoxicity, carcinogenicity, and reproductive toxicity of xanthorrhizol, future studies on these areas would contribute important knowledge.

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