+86-28-82633987
Product Name: Z-Guggulsterone
Synonym name: Z-Guggulsterone; cis-Guggulsterone; (Z)-Guggulsterone
Catalogue No.: BP0368
Cas No.: 39025-23-5
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 Z-Guggulsterone
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
34.1400
3.5189
3.5189
.0151
9.0020
35.3773
High
83.1671
4.2203
No
Yes
No
No
Yes
No
0.0
No
No
Yes
Yes
Cis-myrrh sterone ((Z)-Guggulsterone) is a naturally occurring 3-hydroxysteroid compound, mainly extracted from the resin of the Indian traditional medicinal plant Myrrh Tree (Commiphora wightii). As a cis-isomer of myrrh sterone, cis-myrrh sterone has attracted widespread attention in the field of natural product pharmacology in recent years due to its unique chemical structure and biological activity. Research shows that cis-myrrh sterone has significant anti-inflammatory effects and demonstrates regulatory ability to target various inflammation-related molecules. In addition, its androgen-like activity provides a theoretical basis for its potential applications in endocrine regulation and metabolic diseases. This paper will systematically review the chemical structure and physicochemical properties of cis-myrrhosterone, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation and pharmacokinetic characteristics, and explore its clinical application prospects and research prospects, aiming to provide theoretical support and research directions for the in-depth development and application of this natural product.
The molecular formula of cis-myrrh sterone is C21H28O2, with a molecular weight of 312.4530. Its chemical structure belongs to 3-hydroxysteroids, with a typical steroidal backbone structure. Unlike trans isomers, it is distinguished by its cis configuration (Z configuration) in which it has double bonds in the steroid skeleton. This cis configuration gives it a unique spatial configuration, which in turn influences its affinity for binding to biological targets and its biological activity.
In terms of physicochemical properties, cis-myrrh sterone has a LogP value of 3.5189, indicating good lipid solubility, which helps penetrate cell membranes and the blood-brain barrier (BBB has high permeability). Its topological pole surface area (TPSA) is 34.14 Ų, indicating low molecular polarity and further supporting its good membrane permeability. Low water solubility (0.0151 mg/mL) suggests limited solubility in the aqueous phase, which may affect oral bioavailability. Notably, this compound does not exhibit hERG channel inhibitory activity, suggesting a low risk of cardiotoxicity; The Ames mutagenic test result was 0.0, indicating a low genotoxicity risk and providing a positive basis for safety evaluation.
Cis-myrrh sterone mainly comes from the resin of the myrrh tree (Commiphora wightii), which is a small tree or shrub widely distributed across the Indian subcontinent and parts of the Middle East. Myrrh tree resin has long been used in traditional medicine as a natural source for anti-inflammatory, analgesic, and lipid-lowering drugs. Cis-myrrh sterone, as one of the active components in myrrh resin, has relatively low content and requires efficient extraction and separation techniques.
The extraction method usually uses organic solvent extraction methods, with commonly used solvents including ethanol, methanol, and ethyl acetate. The extraction steps generally include resin crushing, solvent soaking, filtration, and concentration. To improve purity, subsequent purification is often performed by column chromatography (such as silica gel column chromatography) or high-performance liquid chromatography (HPLC). In recent years, supercritical CO2 extraction technology has also been applied to the extraction of myrrh sterone, as it is environmentally friendly and effectively protects active ingredients from thermal degradation. Additionally, isomer separation of cis-myrrh sterone usually relies on chiral chromatography techniques to ensure the acquisition of high-purity cis conformation.
The most notable pharmacological activity of cis-myrrhisterone is its anti-inflammatory effect. Numerous in vivo and in vitro experiments have shown that this compound can effectively inhibit the production of inflammatory mediators and activate inflammatory signaling pathways. In mouse inflammation models, cis-myrrh sterone significantly reduced the expression levels of pro-inflammatory cytokines such as tumor necrosis factor α (TNF-α), interleukin-6 (IL-6), and nitric oxide synthase 2 (NOS2), alleviating tissue inflammatory responses.
Additionally, cis-myrrh sterone inhibits inflammation-related enzymes such as cyclooxygenase 1 (PTGS1) and cyclooxygenase 2 (PTGS2), further blocking prostaglandin synthesis and reducing the release of inflammatory mediators. Its regulation of the inflammasome-related protein CASP1 suggests that it may alleviate pyroptosis and inflammatory cascade by inhibiting inflammasome activation.
Cis-myrrhalone, which has androgen-like activity, can bind to androgen receptors and activate related signaling pathways. This property gives it potential application value in regulating endocrine functions and promoting metabolic balance. Some studies have shown that cis-myrrh sterone can affect lipid metabolism, lower blood lipid levels, and has anti-atherosclerotic effects.
Cis-myrrh sterone modulates pain receptors such as TRPV1 and TRPA1, demonstrating analgesic potential. By inhibiting the excessive activation of these ion channels, it alleviates neuroinflammation and pain transmission, suggesting its potential application in chronic pain and neuroinflammatory diseases.
The anti-inflammatory mechanism of cis-myrrhosterone involves multiple signaling pathways and key molecular targets. Its main targets include:
In summary, cis-myrrh sterone exerts its broad-spectrum anti-inflammatory and analgesic effects through multi-target and multi-pathway coordinated regulation.
The druggability parameters of cis-myrrhosterone indicate that it has good potential for drug development. Its molecular weight is 312.4530, which meets the Lipinski rule, and its LogP is 3.5189, indicating moderate lipid solubility, which is beneficial for oral absorption and cell membrane penetration. The TPSA is 34.14 Ų, and its low polarity helps penetrate the blood-brain barrier, suggesting its potential for central nervous system diseases.
Low water solubility (0.0151 mg/mL) may limit its oral bioavailability, and solubility needs to be improved through formulation technology. Cis-myrrh sterone did not show hERG channel inhibition, reducing the risk of cardiotoxicity. A negative Ames test indicated a low genotoxicity risk and good safety.
Pharmacokinetic studies have shown that cis-myrrh sterone has good distribution capacity in the body, especially effective in crossing the blood-brain barrier. Its metabolism mainly occurs through the hepatic enzyme system, and the metabolites and excretion pathways still require further research. Preliminary in vivo pharmacokinetic data indicate a moderate half-life, making it suitable for development as an oral formulation.
Cis-myrrh sterone, due to its remarkable anti-inflammatory and androgen-like activity, shows broad clinical application prospects in various disease fields. Its potential therapeutic effects in chronic inflammatory diseases (such as rheumatoid arthritis, inflammatory bowel disease, neuroinflammation, etc.) warrant further study. Additionally, cis-myrrh sterone regulates lipid metabolism and suggests its potential in metabolic syndrome, atherosclerosis, and non-alcoholic fatty liver disease.
In neurological diseases, cis-myrrh sterone regulates the TRPV1/TRPA1 channel, providing analgesic and neuroprotective effects, and may become a novel treatment for chronic pain and neurodegenerative diseases.
Future research should focus on preclinical safety evaluation, pharmacokinetic optimization, and formulation development of cis-myrrh sterone. At the same time, by integrating modern molecular biology techniques, the molecular mechanisms and target networks are further elucidated, providing a solid foundation for clinical translation. The implementation of multicenter, randomized controlled clinical trials will be a key step in verifying their clinical efficacy and safety.
Cis-myrrhosterone, as a natural 3-hydroxysteroid with androgen-like activity and multi-target anti-inflammatory effects, demonstrates good pharmacological activity and druggability. Its unique chemical structure endows it with diverse biological functions, especially excelling in inflammation regulation and pain relief. Although research on its pharmacokinetics and clinical applications is still in its early stages, its safety and multi-target mechanism of action lay a solid foundation for subsequent drug development. In the future, cis-myrrhosterone is expected to become an important natural drug candidate for treating inflammation-related and metabolic diseases, promoting the translation of pharmacological research on natural products into clinical applications.
Shenshuai
Wenjing
Hedandan
