Product Name: (E)-Guggulsterone
Synonym name: E-Guggulsterone; trans-Guggulsterone; Guggulsterone E
Catalogue No.: BP1402
Cas No.: 39025-24-6
Formula: C21H28O2
Mol Weight: 312.453
Botanical Source: Commiphora mukul and Ailanthus grandis
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Can be supplied from milligrams to grams.
For Reference Standard and R&D, Not for Human Use Directly.
Inquire for bulk scale.
HPLC of (E)-Guggulsterone
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
Trans-myrrh sterone ((E)-Guggulsterone) is a 3-hydroxysteroid compound with significant biological activity, molecular formula C21H28O2, molecular weight 312.45, CAS number 39025-24-6. As one of the main active ingredients in the resin of the myrrh tree (Commiphora wightii), trans-myrrhosterone has attracted attention for its multi-target regulatory capabilities, especially showing potential medicinal value in anti-inflammatory, metabolic regulation, and hormone regulation. Its molecular structure contains a typical steroid backbone, which imparts androgen-like activity and can regulate various cellular signaling pathways, participating in the regulation of inflammatory responses.
In recent years, with the deepening of natural product pharmacology, research into the pharmacological effects and molecular mechanisms of trans-myrrhisterone has made significant progress, especially with its potential for application in inflammation-related diseases being widely explored. This paper will systematically review the chemical structure and physicochemical properties, plant origin and extraction methods, pharmacological activity and mechanism of action of trans-myrrhisterone, druggability evaluation and pharmacokinetic characteristics, combined with its clinical application prospects, aiming to provide theoretical basis and reference for further research and development of this compound.
Trans-myrrh sterone belongs to steroid compounds with a typical tetracyclic steroid backbone, and the presence of three hydroxyl groups gives it specific polarity and biological activity. Its chemical name is (3β)-3-hydroxy-20-ene-17-one-4-ene-steroid, with a molecular weight of 312.45 and a LogP value of 4.15, indicating good lipid solubility and facilitating cell membrane penetration. TPSA (topological pole surface area) is 34.14 Ų, with 2 hydrogen bond receptors, indicating moderate polarity in intermolecular interactions, which may affect receptor binding affinity and bioavailability.
In the structure of trans-myrrh sterone, the double bond is configured as trans (E-type), a conformation that has an important impact on its biological activity. The rigid structure of the steroid framework and the presence of 3-hydroxyl groups enable it to bind to various nuclear receptors and signaling molecules, exerting regulatory effects. Additionally, its physicochemical properties, such as moderate lipid solubility and molecular size, are beneficial for drug distribution and cellular uptake, but its blood-brain barrier penetration ability remains unclear and requires further experimental validation.
Trans-myrrh sterone mainly comes from the resin of the myrrh tree (Commiphora wightii, formerly Commiphora mukul), commonly known as "myrrh" or "Gugur resin." Myrrh trees are widely distributed in arid and semi-arid regions of the Indian subcontinent, and their resin is used in traditional Indian medicine (Ayurveda) as a natural medicinal material for anti-inflammatory, lipid-lowering, and arthritis treatment.
The resin contains a relatively high content of trans-myrrh sterone, and extraction typically uses organic solvent extraction combined with column chromatography separation. Common extraction solvents include ethanol, methanol, or ethyl acetate. The extraction process requires controlling temperature and time to prevent degradation of active ingredients. After extraction, purity identification and content determination were performed using high-performance liquid chromatography (HPLC) and mass spectrometry (MS) techniques. In recent years, the application of ultrasound-assisted extraction and supercritical CO2 extraction technologies has improved the extraction efficiency and purity of trans-myrrhisterone, reduced solvent residues, and aligned with green chemistry principles.
In addition, the diversity of plant sources and environmental factors significantly affect the content of trans-myrrh sterone, with fluctuations in resin content across different production areas and harvesting seasons, indicating that future research should emphasize raw material standardization and quality control.
Pharmacological activity studies of trans-myrrh sterone mainly focus on its anti-inflammatory, metabolic regulation, and hormone modulatory effects. As a 3-hydroxysteroid, it exhibits androgen-like activity, regulating various nuclear receptors and signaling pathways, exerting multi-target and multi-mechanism pharmacological effects.
Trans-myrrh sterone is the most extensively studied in the field of anti-inflammatory treatment. It inhibits the occurrence and progression of inflammatory responses by regulating various inflammatory mediators and signaling molecules. Both in vitro cell and animal inflammation models showed that this compound can significantly reduce the expression of pro-inflammatory cytokines such as IL-6 and TNF-α, inhibit activation of inflammatory signaling pathways like NF-κB and STAT3, thereby alleviating inflammatory damage.
Specifically, trans-myrrhisterone can inhibit the activity of CASP1 (inflammasome-associated caspase-1), reducing inflammasome-mediated cytokine maturation and release. Additionally, it modulates the TRPV1 and TRPA1 plasma channels, affecting neuroinflammation and pain perception. Inhibition of PTGS1 and PTGS2 (cyclooxygenases 1 and 2) further reduces prostaglandin synthesis and alleviates inflammatory responses. Downregulation of NOS2 (induced nitric oxide synthase) expression also helps alleviate oxidative stress and inflammation.
In addition to anti-inflammatory, trans-myrrh sterone has been reported to have potential activities such as regulating lipid metabolism, anti-tumor, and neuroprotection. Its androgen-like structure gives it a regulatory effect in hormone-related diseases, but the related mechanisms still require further study.
Trans-myrrhalone's mechanism of action is complex, involving multiple signaling pathways and molecular targets, reflecting its multi-target pharmacological properties.
As a steroid-structured compound, trans-myrrh sterone can bind to various nuclear receptors and regulate gene transcription. Research shows that it can antagonize the cholesterol metabolism-related Farnesoid X receptor (FXR), affecting bile acid metabolism and lipid homeostasis. Additionally, it has partial agonistic activity on androgen receptors (ARs) and may be involved in physiological and pathological processes related to hormone regulation.
Trans-myrrh sterone inhibits the NF-κB (nuclear factor κB) signaling pathway, blocks the transcription expression of pro-inflammatory genes, and reduces the production of key inflammatory mediators such as IL-6 and TNF-α. STAT3 (Signal Transduction and Transcription Activator 3) is also one of its targets; inhibiting this pathway helps alleviate chronic inflammation and inflammatory states in the tumor microenvironment.
TRPV1 and TRPA1 are ion channels involved in pain and inflammation perception; trans-myrrhinol-sterone alleviates inflammation-related pain and neuroinflammatory responses by modulating the activity of these channels.
CASP1, as a key enzyme in the inflammasome, is involved in the maturation and secretion of IL-1β. Trans-myrrh sterone inhibits CASP1 activity and reduces inflammatory responses mediated by inflammasomes. At the same time, by downregulating NOS2 expression, excess nitric oxide production is reduced, oxidative stress is alleviated, and tissue is protected from inflammatory damage.
Druggability evaluation of trans-myrrhisterone shows it has certain potential for drug development, but there are also several challenges.
Its molecular weight is 312.45, LogP 4.15, indicating good lipid solubility, facilitating cell membrane penetration and oral absorption. TPSA is 34.14 Ų, with 2 hydrogen bond acceptors, complying with Lipinski rules and expected to have good bioavailability.
However, current safety data on its blood-brain barrier penetration ability, hepatotoxicity, cardiotoxicity (including hERG channel inhibition), and genotoxicity (Ames assay) are still lacking and require further systematic evaluation.
A few in vivo pharmacokinetic studies have shown that trans-myrrh sterone is absorbed quickly after oral administration, but its bioavailability is limited by first-pass effects and metabolic stability. Its metabolic pathway mainly involves the hepatic cytochrome P450 enzyme system, and the activity and toxicity of these metabolites have not been fully elucidated.
Currently, systematic toxicological studies are lacking, especially regarding safety assessment for long-term medication. Given its androgen-like activity, attention should be paid to potential hormone-related side effects, such as endocrine disruption and changes in sex hormone levels.
Trans-myrrhosterone, as a multi-target anti-inflammatory natural product, has broad clinical application potential. Its application prospects in chronic inflammatory diseases (such as rheumatoid arthritis and inflammatory bowel disease), metabolic syndrome, and certain hormone-related diseases are promising.
Based on its regulation of key inflammatory factors such as IL-6, TNF-α, NF-κB, and STAT3, trans-myrrhsterone is expected to become a candidate molecule for novel anti-inflammatory drugs. Especially when traditional anti-inflammatory drugs have significant side effects, natural products offer new treatment approaches.
Trans-myrrh sterone may have an adjunctive therapeutic effect on metabolic diseases such as hyperlipidemia and atherosclerosis by regulating cholesterol metabolism-related nuclear receptors. Animal studies have supported its lipid-lowering and anti-atherosclerosis, but clinical data are lacking.
Although trans-myrrhosterone demonstrates good pharmacological activity, its druggability and safety still require systematic evaluation. Future research should focus on:
Moreover, based on modern molecular biology techniques, in-depth analysis of its targets and signaling pathways will help accurately identify its therapeutic indications and promote its clinical translation.
Trans-myrrh sterone, a 3-hydroxysteroid compound derived from traditional medicinal plant myrrh, has become a hot topic in natural product pharmacology research due to its multi-target regulatory ability and significant anti-inflammatory activity. Its potential applications in anti-inflammation, metabolic regulation, and hormone-related diseases demonstrate significant drug development value.
However, research on its safety, pharmacokinetics, and clinical applications is still in its early stages, urgently requiring systematic pharmacological and toxicological evaluation and clinical validation. In the future, through multidisciplinary collaboration combined with modern medicinal chemistry, molecular biology, and clinical medical approaches, trans-myrrhisterone is expected to become an important component of new natural medicines, providing new strategies and options for treating inflammatory and metabolic diseases.
