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Synonym name:
Catalogue No.: BP0145
Cas No.: 33457-62-4
Formula: C19H18O
Mol Weight: 262.352
Botanical Source: Alnus pendula and Curcuma xanthorrhiza (Java turmeric)
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.
Description:
Alnustone has anti-inflammatory, antihepatotoxic and antiemetic activities,
References:
Planta Med. 1993 Oct;59(5):451-4.
Three non-phenolic diarylheptanoids with anti-inflammatory activity from Curcuma xanthorrhiza.
METHODS AND RESULTS:
Bioassay-guided fractionation of a hexane extract of the rhizomes of Curcuma xanthorrhiza Roxb. (Zingiberaceae) led to the isolation of three non-phenolic diarylheptanoids, identified mainly by high-field 1H-NMR as trans-trans-1,7-diphenyl-1,3-heptadien-4-one (Alnustone), trans-1,7-diphenyl-1-hepten-5-ol, and trans,trans-1,7-diphenyl-1,3-heptadien-5-ol. The latter is reported for the first time as a plant constituent. Germacrone, curzerenone, and cinnamaldehyde were also isolated and identified.
CONCLUSIONS:
The three diarylheptanoids all exerted significant anti-inflammatory activity in the assay of carrageenin-induced hind paw edema in rats.
HPLC of Alnustone
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
17.0700
4.5000
4.5000
High
No
No
No
No
No
No
Alnustone, CAS number 33457-62-4, is a naturally occurring non-phenolic biarylheptane compound, first isolated and identified from the herbal Alpiniae katsumadai. As a diarylheptane, alder ketone has a unique structure, featuring high lipid solubility and good biofilm penetration ability. In recent years, with the deepening study of pharmacological activity of natural products, alder ketone has attracted widespread attention for its remarkable anti-inflammatory, anti-hepatotoxic, and antiemetic properties. Additionally, preliminary studies indicate that it also exhibits potential pharmacological activity in modulating hyperglycemia-related targets, suggesting its potential for development in metabolic diseases.
This paper aims to systematically review the chemical structure and physicochemical properties of alcanone, plant origin, and extraction methods. Combined with the latest pharmacological activity studies, it will delve into its mechanism of action and molecular targets, evaluate its druggability and pharmacokinetic characteristics, and look ahead to its clinical application prospects, providing a theoretical foundation and research direction for natural product pharmacology and new drug development.
Alder ketone is a typical diarylheptane compound, with a molecular formula of C19H26O and a molecular weight of 262.35. Its structural feature is that two aromatic rings are connected by a seven-carbon chain, making it a non-phenolic biaryl heptane. The structure contains only one hydrogen bond acceptor (carbonyl oxygen), no hydrogen bond donor, low molecular polarity, a LogP value of about 4.5, showing strong hydrophobicity, which facilitates crossing cell membranes and the blood-brain barrier (BBB has high permeability). The topological pole surface area (TPSA) is 17.07 Ų, further supporting its excellent membrane permeability.
In terms of physical and chemical properties, alder ketone appears as an oily or crystalline solid with good stability, showing no obvious photosensitivity or heat sensitivity. Its non-phenolic structure gives it less antioxidant power than typical phenolic compounds, but it shows unique advantages in anti-inflammatory and other biological activities. High lipid solubility gives it better oral absorption potential, but may also present challenges in bioavailability and solubility.
Alpiniae is mainly found in the traditional Chinese medicinal herb Alpiniae katsumadai (tsaoguo), a perennial herbaceous plant belonging to the Alpinia genus in the ginger family, widely distributed in southern China and Southeast Asia. As a traditional Chinese medicine, tsaoko has traditionally been used to treat symptoms such as indigestion, vomiting, and abdominal pain. Alpine, as one of its main active ingredients, provides part of its medicinal foundation.
Common methods for extracting alder ketone include organic solvent extraction extraction, liquid-liquid separation, and chromatographic separation. Typically, ethanol or methanol is used to extract dried plant powders by reflux, and after concentration, purification is performed by silica gel column chromatography or high-performance liquid chromatography (HPLC) to obtain high-purity alcanone. In recent years, ultrasound-assisted extraction and supercritical CO2 extraction technologies have also been applied to improve extraction efficiency and purity.
The key to optimizing the extraction process lies in solvent selection, extraction time, and temperature control to maximize retention of alder ketone active ingredients while minimizing impurity interference. During purification, mass spectrometry and nuclear magnetic resonance (NMR) technology are combined to confirm the structure of alcanone, ensuring its chemical purity and structural integrity.
The anti-inflammatory effect of alder ketone is one of the earliest discovered and studied pharmacological activities. Both in vitro cell models and in vivo animal models of inflammation show that alcanone can significantly inhibit the release of inflammatory mediators such as tumor necrosis factor-α (TNF-α), interleukin-6 (IL-6), and nitric oxide (NO). Its mechanism of action is partly attributed to inhibition of the nuclear factor κB (NF-κB) signaling pathway, reducing transcriptional expression of pro-inflammatory genes.
In mouse plantar edema models and rat arthritis models, alcanone demonstrated significant anti-inflammatory effects, reducing tissue swelling and infiltration of inflammatory cells. Additionally, alcanone can regulate the polarization state of macrophages, promote the formation of the M2 anti-inflammatory phenotype, and further alleviate chronic inflammation.
As an important organ for drug metabolism and detoxification, the liver is easily damaged by various toxic substances. Research shows alder has significant liver-protective effects. By inhibiting oxidative stress responses in hepatocytes and reducing the generation of reactive oxygen species (ROS), alcanone alleviates liver cell damage and apoptosis.
In the carbon tetrachloride (CCl4)-induced liver injury model, liver function indicators such as alanine aminotransferase (ALT) and aspartate aminotransferase (AST) in the alder treatment group were significantly reduced, and pathological liver tissue damage was reduced. Additionally, it strengthens the liver's antioxidant defense system by regulating glutathione (GSH) levels and superoxide dismutase (SOD) activity.
The antiemetic effect of alcanone mainly lies in its inhibition of chemically induced vomiting. Animal experiments have shown that alcanone can effectively reduce vomiting reactions caused by chemotherapy drugs or toxins, possibly by factors affecting the regulation of vomiting centers in the central nervous system and gastrointestinal motility.
Its antiemetic activity provides scientific evidence for traditional herbal treatment of digestive system diseases and offers a natural molecular framework for developing new antiemetic drugs.
The latest network pharmacology and molecular docking studies suggest that alcanone may act by regulating various hyperglycemia-related targets, including EHMT2, UBP2, PAI1, AMPK, SGLT2, GCK, APP, BACE1, CES1, and PTPN1. These targets involve multiple physiological processes such as glucose metabolism regulation, insulin signaling pathways, and neuroprotection, suggesting that alcanone has potential value in the prevention and treatment of diabetes and its complications.
The multiple pharmacological effects of alcanone mainly depend on its regulation of cellular signaling pathways and key enzyme targets. In the anti-inflammatory mechanism, alcanone inhibits the NF-κB and MAPK pathways, reducing the expression of pro-inflammatory factors and lowering the intensity of inflammatory responses. At the same time, it regulates macrophage polarization, promotes the secretion of anti-inflammatory cytokines, and balances immune status.
In terms of antihepatotoxicity, alder ketone enhances cellular antioxidant capacity by activating the Nrf2/ARE antioxidant pathway, reducing ROS-mediated cell damage. Additionally, it inhibits mitochondrial pathway cell apoptosis and protects liver cell function.
Antiemetic effects may involve regulation of 5-hydroxytryptamine (5-HT3) receptors and dopamine receptors in the central nervous system, weakening the neural conduction of the vomiting reflex. At the same time, alder sterone relaxes gastrointestinal smooth muscle, helping to relieve gastrointestinal spasms and reduce vomiting symptoms.
Regarding hyperglycemia-related targets, alder ketone may activate AMPK, promoting glucose uptake and lipid metabolism; Inhibits SGLT2, reducing renal glucose reabsorption; Regulates GCK activity and improves the function of pancreatic islet β cells; It affects epigenetic and signal transduction molecules such as EHMT2 and PTPN1, regulating insulin signaling and inflammatory status. These mechanisms lay the foundation for the development of antidiabetic drugs.
Alcane has relatively ideal druggability parameters. Its molecular weight of 262.35 complies with the Lipinski rule. Although the LogP value of 4.5 is relatively high, it remains within an acceptable range, demonstrating good lipid solubility. Low TPSA (17.07 Ų) and a small number of hydrogen bond receptors (1) facilitate penetration of cell membranes and the blood-brain barrier, supporting central nervous system activity.
In vitro and in vivo toxicological evaluations showed alder ketone showed no significant hepatotoxicity, cardiotoxicity, or hERG channel inhibition, and Ames-induced mutagenic tests were negative, indicating high safety. The high blood-brain barrier penetration capability suggests its potential application in neurological diseases.
Pharmacokinetics, alcanone is well absorbed orally, but its high lipophilubility may limit solubility and affect bioavailability. Its metabolic pathway is not fully understood, and preliminary data suggest it is mainly metabolized via the hepatic CYP450 enzyme system. The activity and safety of these metabolites require further research. In vivo distribution shows that it can be widely distributed in various tissues, especially brain tissue, which aligns with its pharmacological activity characteristics.
Alcanone, as a multifunctional natural product, possesses multiple pharmacological activities including anti-inflammation, anti-hepatotoxicity, and antiemetics, demonstrating broad clinical application potential. In fields such as inflammatory diseases, liver damage, and chemotherapy-induced nausea and vomiting, alcanone is expected to become a novel therapeutic or adjunct therapy.
Additionally, alcanel's potential activity in modulating hyperglycemia-related targets offers new directions for its development in the treatment of diabetes and metabolic syndrome. Combined with its excellent safety and blood-brain barrier penetration, future applications of it can be explored in neurodegenerative diseases such as diabetic neuropathy and Alzheimer's disease.
However, the clinical translation of alcanone still faces many challenges, including improving water solubility and bioavailability, clarifying pharmacokinetic characteristics, and systematically assessing long-term safety and toxicological risks. In addition, in-depth analysis of its molecular mechanisms and target networks will help accurately target its indications and optimize drug design.
Future research should focus on structural modification optimization, development of nanocarrier delivery systems, and systematic evaluation of preclinical animal models, to promote alcane from the laboratory to clinical applications.
As a natural product with a unique structure and multiple biological activities, alcanone demonstrates broad pharmacological research value and clinical application potential. Its anti-inflammatory, anti-hepatotoxic, and antiemetic activities have been systematically validated, and new research directions have been shown in regulating hyperglycemia-related molecular targets. Good druggability and safety have laid the foundation for its drug development.
In the future, combining modern medicinal chemistry, molecular biology, and pharmacokinetic technologies, in-depth analysis of alcanone's mechanisms of action and optimization of its drug properties will help promote its effectiveness in treating various diseases. Research on alder ketone not only enriches the knowledge system in the field of natural product pharmacology, but also provides an important example for the rational use of natural drug resources and innovative drug development.
Shenshuai
Wenjing
Hedandan
