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Synonym name: Bessisterol
Catalogue No.: BP0157
Cas No.: 481-18-5
Formula: C29H48O
Mol Weight: 412.702
Botanical Source: spinach (Spinacia oleracea) leaves, cucumber (Cucumis sativus), alfalfa meal, bark of Acacia concinu, Acacia caesia, pumpkin seeds and senega root. various marine sponges incl. Axinella cannabina
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 Alpha-Spinasterol
HNMR of Alpha-Spinasterol
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
20.2300
8.8600
No
No
No
No
Unknown
No
Unknown
Alpha-Spinasterol (CAS No.: 481-18-5) is a natural steroid compound and belongs to the category of jugmasterane hydride derivatives. In recent years, with the deepening study of pharmacological activity of natural products, bromelsterol has gradually become a research hotspot in the field of pharmacology due to its remarkable bioactivity and good safety. As a novel and safe transient receptor potential vanillin acid 1 (TRPV1) receptor antagonist, bromesterol demonstrates excellent anti-inflammatory, analgesic, and regulatory potential for various metabolic diseases. In addition, mestiol possesses multiple biological activities including antibacterial, antidepressant, and antioxidant properties, showing broad pharmacological application prospects.
This review aims to systematically summarize the chemical structure and physicochemical properties of brosterol, its plant origins and extraction methods, with a focus on its pharmacological activity and mechanism of action, explore its druggability and pharmacokinetic characteristics, and anticipate its clinical application potential, providing theoretical basis and reference for subsequent research and drug development.
The chemical name of spirasterol is α-spinasterol, with a molecular formula of C29H48O and a molecular weight of 412.69. Its structure is based on the stigmasterane framework, belonging to tetracyclic steroid compounds, containing a hydroxyl group as the only polar group. Domesterol has a LogP value as high as 8.86, indicating high hydrophobicity. Its TPSA (topological pole surface area) is 20.23 Ų, and it has 1 hydrogen bond acceptor, indicating low polarity and strong lipophilicity.
Structurally, the peptide sterol molecule contains a typical steroid nuclear structure, with multiple methyl and alkyl side chains, which give it strong membrane affinity and compatibility with lipid environments. Its high hydrophobicity may affect its distribution and bioavailability in vivo, but it also facilitates penetration of cell membranes and enables intracellular targeting.
Domesterol is widely found in various plants, especially in the leaves, stems, and roots of some medicinal plants. Common plants containing brodomesterol include those in the pineapple, legume, and cucurbite families. Its naturally occurring form is mostly in free form or in combination with sugars to form steroidogenic agents.
Common extraction methods for domesterol mainly include solvent extraction, supercritical fluid extraction, and column chromatography separation. Traditional solvent extraction mostly uses organic solvents such as ethanol, methanol, or ethyl acetate, combined with ultrasound-assisted extraction technology to improve extraction efficiency. The crude extract is further purified by silica gel column chromatography or high-performance liquid chromatography (HPLC) to obtain high-purity spirosterol.
In recent years, green extraction technologies such as supercritical carbon dioxide extraction and microwave-assisted extraction have gradually been applied to the separation of vosterol, offering advantages such as high extraction efficiency, low solvent residue, and environmental friendliness, providing technical support for large-scale production.
Research on the pharmacological activity of pentasterol covers multiple aspects including anti-inflammatory, analgesic, antibacterial, antidepressant, antioxidant, and metabolic disease regulation, demonstrating its multi-target and multi-pathway biological effects.
As an antagonist of the TRPV1 receptor, pentasterol can effectively inhibit TRPV1-mediated calcium influx, thereby reducing inflammation and pain. The TRPV1 receptor plays a key role in inflammation and pain signaling. Domesterol demonstrates good anti-inflammatory and analgesic effects by blocking the activation of this receptor and reducing the release of inflammatory mediators. Additionally, brosterol inhibits cyclooxygenase (COX-1 and COX-2) activity, with IC50s of 16.17 μM and 7.76 μM, respectively, further weakening the inflammatory response.
Pentasterol has shown significant potential in treating metabolic diseases such as diabetic nephropathy. Related studies have shown that domesterol improves the pathological progression of diabetic nephropathy by regulating signaling pathways such as AMPK, PTPN1, and STAT3, and reduces kidney inflammation and fibrosis. Additionally, its antioxidant activity helps alleviate oxidative stress caused by high blood sugar and protect kidney function.
Pentosolol can prevent testosterone propionate (TP)-induced benign prostatic hyperplasia, suggesting its potential application value in the treatment of benign prostatic hyperplasia (BPH). Its mechanism of action may involve regulating the inflammatory response and cell proliferation of prostate tissue, slowing down the process of prostate enlargement.
Pentasterol also exhibits various activities including antibacterial, antidepressant, and antioxidant properties. Its antibacterial effect targets various Gram-positive and negative bacteria, possibly by disrupting bacterial membrane structures or inhibiting key enzyme activities. The antidepressant effect may be related to its regulation of central nervous system neurotransmitters and antioxidant capacity. Antioxidant activity helps reduce cell damage caused by free radicals and protects tissue function.
The multiple pharmacological effects of domesterol stem from its regulation of various molecular targets, involving ion channels, enzymes, transcription factors, and signal transduction molecules.
TRPV1 is a non-selective cation channel widely found in sensory neurons and involved in pain and inflammation signaling. As an effective antagonist of TRPV1, Pentasterol blocks its activation, reduces calcium influx, inhibits nerve excitation and the release of inflammatory mediators, and exerts analgesic and anti-inflammatory effects.
Betasterol's inhibitory effect on cyclooxygenases 1 and 2 reduces prostaglandin synthesis and alleviates inflammatory responses. COX-2 is particularly highly expressed in the inflammatory and tumor microenvironment, and its inhibition by amphisterol helps control chronic inflammation.
Domesterol promotes cellular energy metabolism balance and improves insulin sensitivity by activating the AMPK (5' AMP-activated protein kinase) signaling pathway. PTPN1 (protein tyrosine phosphatase 1B) acts as a negative regulator of insulin signaling, with its activity inhibited by melostanol, enhancing insulin signaling. Regulation of the STAT3 signaling pathway helps suppress inflammation and fibrotic responses.
Additionally, memesterol regulates NFE2L2 (nuclear factor E2-related factor 2)-mediated antioxidant responses, enhancing cells' defense against oxidative stress. Its effect on HIF1A (hypoxia-inducing factor 1α) may be involved in regulating tissue hypoxia status and metabolic adaptation.
Domesterol modulates targets such as ABCB1 (P-glycoprotein) and PRKCA (protein kinase Cα), potentially affecting drug transport and signal transduction, further enriching its pharmacological spectrum of effects.
The druggability parameters of spirasterol indicate certain potential, but there are also challenges. Its molecular weight is 412.69, meeting the molecular weight requirements of the Lipinski rule. The LogP value reaches as high as 8.86, indicating strong lipophilicity, which may affect its water solubility and oral bioavailability, requiring pharmaceutical improvements to enhance its solubility and absorption rate.
TPSA is only 20.23 Ų, with a hydrogen bond receptor count of 1, which theoretically favors cell membrane penetration. Nevertheless, existing data indicate that betasterol does not easily cross the blood-brain barrier, limiting its application for central nervous system-related diseases but simultaneously reducing potential central toxicity risks.
In terms of safety, domesterol showed no hepatotoxicity, cardiotoxicity, or hERG channel inhibition, demonstrating a favorable safety profile. Ames-induced mutagenic assay data are still lacking, and further evaluation of its genotoxicity is needed.
Pharmacokinetic research is still in its early stages, and the absorption, distribution, metabolism, and excretion (ADME) characteristics of domesterol after oral administration in the body need further clarification. Its high lipophilicity may lead to tissue enrichment, affecting half-life and metabolic pathways. In the future, its pharmacokinetic properties can be improved through structural modification or nanocarrier systems.
As a multi-target, multifunctional natural steroid compound, spinsterol has broad clinical application potential in anti-inflammatory and analgesic relief, metabolic disease regulation, and prostate disease prevention and treatment.
Due to the key role of the TRPV1 receptor in various pain and inflammatory diseases, memesterol, as a safe and effective TRPV1 antagonist, is expected to become a new generation of analgesic and anti-inflammatory drugs, especially suitable for treating chronic pain, neuroinflammation, and other refractory diseases.
The regulatory effect of domesterol on diabetic nephropathy and related metabolic disorders provides a theoretical basis for its use as an adjunct therapy for metabolic syndrome and diabetic complications. Combined with its antioxidant and anti-inflammatory properties, it may improve the overall metabolic status and organ function of patients.
Experimental data on the prevention of TP-induced prostatic hyperplasia suggest promising applications of brosterol in treating benign prostatic hyperplasia, especially in reducing prostate inflammation and tissue hyperplasia.
Although the pharmacological activity of pentasterol has been preliminarily confirmed, its clinical translation still faces many challenges. Future research should focus on:
As a naturally derived steroid compound, spinsterol demonstrates broad pharmacological activity and clinical application potential thanks to its multi-target regulatory capabilities and good safety. Its unique advantage as a TRPV1 receptor antagonist gives it significant value in the field of anti-inflammatory and analgesic treatment; At the same time, its therapeutic potential in metabolic and prostate diseases also provides new directions for the development of natural product drugs.
In the future, by integrating modern medicinal chemistry, pharmaceutics, and molecular biology technologies, in-depth research into the mechanisms of action and pharmacokinetic characteristics of domesterol will lay a solid foundation for its clinical application, promote its transformation into safe and effective innovative drugs, and benefit a wide range of patients.
Shenshuai
Wenjing
Hedandan
