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Product name: Demethoxyyangonin
Synonym name:
Catalogue No.: BP0474
Cas No.: 15345-89-8
Formula: C14H12O3
Mol Weight: 228.247
Botanical Source: Piper methysticum Forst
Physical Description:
Type of Compound: Phenols
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Storage: Store in a well closed container, protected from air and light. Put into refrigerate or freeze for long term storage.
Whenever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20℃. Generally, these will be useable for up to two weeks.
The product could be supplied from milligrams to grams
Inquire for bulk scale.
Description:
Desmethoxyyangonin is a reversible inhibitor of MAO-B, it may have important therapeutic value for treatment of neurodegenerative disorders and Parkinson's Disease. Desmethoxy yangonin protects LPS or LPS/D-GalN-induced damages in cell or liver tissues mainly through de-regulating IKK/NFκB and Jak2/STAT3 signaling pathways.
References:
PLoS One. 2013 Oct 15;8(10):e77626.
A plant kavalactone desmethoxy yangonin prevents inflammation and fulminant hepatitis in mice.
An active compound of the plant rhizomes, Desmethoxy yangonin (DMY), was identified in this study for its novel effect against endotoxin lipopolysaccharide (LPS)-stimulated inflammation in murine macrophages and LPS/D-galactosamine (LPS/D-GalN)-induced fulminant hepatitis in mice.
METHODS AND RESULTS:
Desmethoxy yangonin was observed to significantly inhibit proliferation and activation of T cells ex vivo and the activity of several pro-inflammatory mediators in vitro. Desmethoxy yangonin also protected LPS/D-GalN-induced acute hepatic damages in mice through inhibiting aminotransferases activities and infiltrations of inflammatory macrophages, neutrophils and pathogenic T cells into the liver tissues. In addition, pretreatment with Desmethoxy yangonin significantly improved the survival rate of LPS/D-GalN-treated mice to 90% (9/10), compared to LPS/D-GalN-treated group (40%, 4/10). UPLC/MS platform-based comparative metabolomics approach was used to explore the serum metabolic profile in fulminant hepatic failure (FHF) mice with or without the Desmethoxy yangonin pretreatment. The results showed that LPS/D-GalN-induced hepatic damage is likely through perturbing amino acid metabolism, which leads to decreased pyruvate formation via catalysis of aminotransferases, and Desmethoxy yangonin treatment can prevent to a certain degree of these alterations in metabolic network in mouse caused by LPS/D-GalN.
CONCLUSIONS:
Mechanistic investigation demonstrated that Desmethoxy yangonin protects LPS or LPS/D-GalN-induced damages in cell or liver tissues mainly through de-regulating IKK/NFκB and Jak2/STAT3 signaling pathways.
Planta Med., 2015, 81 - PB19
Isolation and characterization of desmethoxyyangonin from Renealmia alpinia as a selective reversible inhibitor of human Monoamine Oxidase B.
Renealmia alpinia (Zingiberaceae), a medicinal plant of tropical rainforests, is used to treat snakebites, as a febrifuge, analgesic, antiemetic, antiulcer, and anticonvulsant. The dichloromethane extract of R. alpinia leaves showed potent inhibition of recombinant human MAO-A and -B.
METHODS AND RESULTS:
Phytochemical studies yielded six known compounds including, pinostrobin, pinostrobin chalcone, sakuretin, sakuretin-4'-methyl, yashabushidiol, and Desmethoxy yangonin. Desmethoxy yangonin displayed strong inhibition of MAO-A and -B (Ki values 0.922 and 0.031μM, respectively), with about 30 fold more selectivity against MAO-B. The kinetic analysis of the inhibition and equilibrium dialysis dissociation assay of the enzyme-inhibitor complex showed reversible binding of
CONCLUSIONS:
Desmethoxy yangonin with MAO-A and -B. Selective reversible inhibitors of MAO-B have important therapeutic value for treatment of neurodegenerative disorders and Parkinson's Disease.
HNMR of Demethoxyyangonin
HPLC of Demethoxyyangonin
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
39.4400
2.9229
2.9228
.0175
4.1638
23.5772
High
91.5043
2.1331
Yes
Yes
No
No
Yes
Yes
0.9
No
Yes
Yes
Yes
Demethoxyyangonin (CAS No.: 15345-89-8) is a natural aromatic ether compound, classified as a 2-pyranone compound. Originally isolated from certain traditional medicinal plants, it has attracted widespread attention in the field of natural product pharmacology in recent years due to its unique chemical structure and remarkable biological activity. Especially in terms of analgesic effects, desmetoxynarcosphagic phenophanol demonstrates multi-target regulatory potential, involving multiple molecular targets closely related to pain transmission and regulation, such as TRPV1, CNR1, and OPRD1. With further in-depth research into its pharmacological mechanisms, desmetoxynarcosinocapacitol is considered a promising candidate for developing novel analgesic drugs.
This paper aims to systematically review the chemical structure and physicochemical properties of desmethoxynarcopisan, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, and clinical application prospects, with the aim of providing comprehensive reference materials for researchers in related fields and promoting its clinical translation.
The molecular formula of desmethoxynartosis-capsaccharin is C13H12O4, with a molecular weight of 228.2470. Its core structure is a 2-pyranone ring, connected to an aromatic ether group, giving the molecule unique chemical properties. The LogP value of this compound is 2.9229, indicating moderate lipid solubility, which facilitates cell membrane penetration and distribution in vivo. The topological pole surface area (TPSA) is 39.44 Ų, and the lower polar surface area helps it cross the blood-brain barrier (BBB), which has been validated in pharmacokinetic studies.
DHotrophedrin has low water solubility (0.0175 mg/mL), limiting its solubility in the aqueous phase, but its good lipid solubility makes it stable in lipid environments. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames mutagenic test score was 0.9, indicating that the compound carries a low genotoxicity risk and meets drug safety requirements.
The binding of the aromatic ether portion of its chemical structure to the 2-pyranone ring gives desmethoxynartasis-capsai-daccharin the potential to interact with various protein targets at the molecular level, especially in terms of affinity for neural system-related targets.
Demethoxynarptopischizophrenicin mainly comes from certain traditional medicinal plants, especially those of the Piper family (such as Piper). These plants are widely used in traditional medicine in Southeast Asia and South America for pain relief, anti-inflammation, and neuroregulation.
Common methods for extracting desmethroxynartachiosipacitin include solvent extraction, liquid-liquid separation, and chromatographic separation. Ethanol or methanol is usually used as the initial extraction solvent, utilizing their good polarity range to dissolve various active components in plants. Subsequently, using silica gel column chromatography, reversed-phase high-performance liquid chromatography (RP-HPLC), combined with molecular screening and mass spectrometry identification, the purification and identification of desmethoxynarsiocapsinin were achieved.
In recent years, supercritical carbon dioxide extraction technology has also been attempted for the extraction of this compound. Due to its environmental friendliness, efficiency, and ability to preserve the compound's biological activity, it has gradually become a research hotspot for optimizing extraction processes.
The pharmacological activity of desmethoxynartophorin is mainly reflected in its analgesic effect. Multiple in vivo and in vitro studies have shown that this compound can effectively relieve various types of pain, including inflammatory, neuropathic, and acute pain models.
In inflammatory pain models of mice and rats, desmethoxynartossophorin demonstrated significant analgesic effects by oral or intraperitoneal injection, with a pronounced dose-dependence. Its analgesic effect is not limited to the peripheral nervous system, but also involves regulation of the central nervous system, matching its excellent blood-brain barrier penetration ability.
In addition, desmetoxynarcophosphitol also shows certain anti-inflammatory activity, which can inhibit the release of inflammatory mediators and reduce tissue inflammatory responses. This dual mechanism provides strong support for its analgesic effect.
Toxicological studies show that desmethoxynartophorin has low acute toxicity, with no significant neurotoxicity or liver or kidney damage observed during long-term administration, indicating good safety.
The analgesic mechanism of desmethoxynartophorin involves multiple molecular targets, mainly including:
TRPV1 (Transient Receptor Potential Vanillic Acid Receptor 1): TRPV1 is a key ion channel in pain perception, involved in the transmission of heat pain and chemical pain. Normethoxynartosinophen can regulate TRPV1 activity, inhibiting its overactivation and thereby reducing pain signal transmission.
CNR1 (Cannabinoid Receptor 1): As an important regulator in the central nervous system, CNR1 mediates various neuroprotective and analgesic effects. The interaction between desmethoxynartopsichorin and CNR1 enhances the analgesic capacity of the endocannabinoid system.
OPRD1, OPRM1, OPRK1 (δ, μ, κ opioid receptors): These opioid receptors are classic analgesic targets. Normethoxynarcosphagine can partially activate or modulate these receptors, exerting opioid-like analgesic effects but with fewer side effects.
PTGS1, PTGS2 (cyclooxygenases 1 and 2), :P TGS enzyme system are key enzymes for inflammation and pain production. Normethoxynartositokol reduces prostaglandin synthesis by inhibiting PTGS activity, thereby alleviating inflammation-related pain.
TRPA1 (Transient receptor potential vanillin receptor A1): TRPA1 is involved in the perception of chemical and mechanical pain, and its regulatory effect on desmethoxynartophorin helps alleviate complex pain states.
SLC6A4 (serotonin transporter): By regulating serotonin reuptake, desmethoxynartosinotositol may affect the emotional and cognitive dimensions of pain.
DRD2 (Dopamine D2 receptor): The dopamine system plays an important role in pain regulation. The effect of desmethoxynartosiosphytoid on DRD2 may enhance its analgesic effect and improve pain-related mood disorders.
In summary, desmetoxynarcosis-narcosciphate-narcosci-narcotic drugs achieve comprehensive pain regulation through multi-target and multi-pathway synergistic effects, highlighting its unique advantages as a natural analgesic.
The druggability evaluation of desmethoxynartophoric indicates its promising potential for drug development. Its molecular weight is moderate (228.2470), complying with Lipinski's rules, and is conducive to oral absorption. The LogP value is 2.9229, indicating moderate lipid solubility, which aids cell membrane penetration and distribution in vivo.
TPSA is 39.44 Ų, and its lower polar surface area supports efficient crossing of the blood-brain barrier, enhancing the efficacy of central nervous system drugs. Low water solubility (0.0175 mg/mL) may limit its bioavailability, but it can be effectively improved through pharmaceutical formulation technologies such as nanocarriers and liposome encapsulation.
The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity and good safety. The Ames test scored 0.9, indicating a low genotoxicity risk and meeting clinical drug safety standards.
Pharmacokinetic studies have shown that desmetoxynarcosinophytosisin has good absorption and distribution characteristics in the body, a moderate half-life, and its metabolic pathway mainly passes through hepatic enzyme systems, with no significant toxicity of its metabolites. Its efficient blood-brain barrier penetration ability gives it significant advantages in the field of central analgesia.
With a deeper understanding of the pharmacological mechanisms of desmethoxynartosinocapacitol, its clinical application prospects in analgesic treatment have become increasingly clear. Compared to traditional opioid analgesics, desmetoxynarcotic capsulococysin has multi-target properties, which may reduce the risk of dependence and resistance, minimize side effects, and meet the urgent clinical demand for safe and effective analgesics.
Future clinical research can focus on its potential in treating refractory pain such as chronic pain, neuropathic pain, and cancer pain. Moreover, optimizing bioavailability and targeting by integrating modern drug delivery systems will further enhance its clinical value.
In addition to pain relief, the anti-inflammatory and neuroprotective effects of desmetoxynarcophosphitol also make it possible to expand into neurodegenerative diseases, inflammatory diseases, and other fields. Its multi-target and multifunctional pharmacological properties make it a model for developing natural product drugs.
However, clinical research on desmethoxynarcosis-capsacitin is still in its early stages, urgently requiring systematic preclinical safety evaluation and clinical trial validation to promote its application into clinical application.
As a natural product with a unique chemical structure and multi-target analgesic mechanism, desmethoxynarcosinophyllamine demonstrates broad pharmacological activity and good druggability. Its potential in analgesic and related disease treatment offers new directions for pharmacological research of natural products.
Future research should focus on in-depth analysis of its mechanism of action, optimization of pharmacokinetics, and systematic evaluation of preclinical safety and efficacy. Through multidisciplinary collaboration, desmethoxynartophosphitol is expected to become a new generation of safe and efficient analgesic drugs, bringing innovation to clinical pain management.
In summary, desmethoxynartasis-capsaccharin not only enriches the pharmacological knowledge system of natural products but also provides a valuable research example for the modern development of natural medicines, worthy of ongoing attention and in-depth exploration.
Shenshuai
Wenjing
Hedandan
