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Product name: 6-Shogaol
Synonym name: 1-(4-Hydroxy-3-methoxyphenyl)-4-decen-3-one
Catalogue No.: BP0095
Cas No.: 555-66-8
Formula: C17H24O3
Mol Weight: 276.376
Botanical Source: grains of paradise (Amomum melegueta) and Zingiber officinale (ginger)
Physical Description: Oil
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, up to kilograms
Inquire for bulk scale.
Descriptions:
6-Shogaol, an active constituent of ginger, is a potent inhibitor of MDA-MB-231 cell invasion, and the molecular mechanism involves at least in part the down-regulation of MMP-9 transcription by targeting the NF-κB activation cascade, thus has potential for clinical use as antimetastatic treatments. [1]
6-Shogaol and 6-gingerol might both exert anti-invasive activity against hepatoma cells through regulation of MMP-9 and TIMP-1 and that 6-shogaol could further regulate urokinase-type plasminogen activity.[2]
6-Shogaol exerts its anti-inflammatory effects by inhibiting the production of prostaglandin E2 (PGE2) and proinflammatory cytokines, such as interleukin-1β (IL-1β) and tumor necrosis factor-α (TNF-α), and by downregulating cyclooxygenase-2 (COX-2), p38 mitogen-activated protein kinase (MAPK), and nuclear factor kappa B (NF-κB) expression; it shows significant neuroprotective effects in vivo in transient global ischemia via the inhibition of microglia, suggests that it is an effective therapeutic agent for treating neurodegenerative diseases.[3]
6-Shogaol reduces the inflammatory response and protects the femoral cartilage from damage produced in a CFA monoarthritic model of the knee joint of rats.[4]
6-Shogaol induces apoptosis in human hepatocellular carcinoma cells in relation to caspase activation and endoplasmic reticulum (ER) stress signaling, affects the ER stress signaling by regulating unfolded protein response (UPR) sensor PERK and its downstream target eIF2α, thus, the PERK/eIF2α pathway plays an important role in 6-shogaol-mediated ER stress and apoptosis in SMMC-7721 cells in vitro and in vivo .[5]
6- Shogaol can prevent secondary pathological events in traumatic Spinal cord injury (SCI) and promotes recovery of motor functions in an animal model raises the issue of whether shogaol could be used therapeutically in humans after SCI.[6]
References:
[1] Ling H, Yang H, Tan S H, et al. Brit J Pharmacol, 2010, 161(8):1763–77.
[2] Chia-Jui Weng ?, Cheng-Feng Wu ?, Huang H W, et al. Mol Nutr Food Res, 2010, 54(11):1618–27.
[3] Sang K H, Moon E, Mi S J, et al. Neuropharmacology, 2012, 63(2):211-23.
[4] Levy A S, Simon O, Shelly J, et al. Bmc Pharmacology, 2006, 6(1):12.
[5] Hu R, Zhou P, Peng Y B, et al. Plos One, 2012, 7(6):1634.
[6] Kang S K, Gon J H, Geun K Y, et al. Eur J Neurosci, 2006, 24(4):1042-52.
[7] Zhang K W, Shen S, Cui X B, et al. J Chinese Pharm Sci, 2009, 44(22):1692-4.
HPLC of 6-Shogaol
HNMR of 6-Shogaol
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
49.6900
3.5900
3.3100
High
No
No
No
No
No
No
6-Shogaol (CAS No.: 555-66-8) is a type of ginger (Zingiber officinale) from the ginger family ) is an important active natural product and belongs to the gingerol class of compounds. As the main component obtained from the dehydration transformation of 6-shogaolol during ginger drying, 6-shogaolol has attracted widespread attention due to its unique chemical structure and significant biological activity. In recent years, with advances in natural product pharmacology and molecular biology technologies, 6-shogaolol has shown great potential in anti-cancer, neuroprotection, anti-inflammatory, and metabolic disease regulation, becoming a hot molecular in the treatment of various diseases.
This review aims to systematically summarize the chemical properties, plant origins, and extraction methods of 6-shogaol, explore its pharmacological activity and mechanism of action in depth, evaluate its druggability and pharmacokinetic characteristics, and look ahead to its clinical application prospects. By integrating the latest research progress, it is hoped that scientific basis and theoretical support will be provided for the drug development and clinical translation of 6-shogaol.
The chemical formula of 6-gingerol is C17H24O3, with a molecular weight of 276.37. Structurally, it belongs to the gingerol family as a dehydration product. Its core framework consists of aromatic phenols containing α,β-unsaturated ketone structures. Specific structural features include a benzene ring with allyl side chains and a ketone group, giving it strong biological activity and reactivity.
In terms of physicochemical properties, the LogP value of 6-gingerol is about 3.59, indicating good lipid solubility, which facilitates cell membrane penetration and distribution in vivo. Its topological pole surface area (TPSA) is 49.69 Ų, and it has 3 hydrogen bond acceptors, suggesting that it possesses certain polarity and binding ability in intermolecular interactions. 6-Sgingerol can cross the blood-brain barrier (BBB) and has the potential to act on the nervous system. Toxicological evaluation showed no significant hepatotoxicity, cardiotoxicity, or hERG channel inhibition; Ames mutagenic test was negative, indicating high safety.
6-Shogaolol is mainly found in the dried rhizomes of ginger and is a secondary metabolite produced by dehydration during heating or drying. As a traditional Chinese medicine and ingredient, ginger's drying conditions (such as temperature and time) significantly affect the content of 6-shogaolol. Generally, the higher the drying temperature, the more shogaolol is produced.
There are various methods for extracting 6-shogaolol, mainly including solvent extraction, ultrasound-assisted extraction, and supercritical fluid extraction. Common solvents include ethanol, methanol, ethyl acetate, etc. During extraction, temperature and time must be controlled to prevent component degradation. Modern extraction technologies, such as ultrasound-assisted extraction, can improve extraction efficiency and purity, and are more environmentally friendly. After extraction, liquid chromatography (HPLC) combined with mass spectrometry (MS) is usually used for qualitative and quantitative analysis to ensure the content and purity of 6-shogaolol in the extract.
6-Sgingerol has demonstrated significant anticancer activity across various tumor models, especially in research on pancreatic cancer and hepatocellular carcinoma. Research shows that 6-gingerol can inhibit the proliferation of human pancreatic tumor cells and enhance the sensitivity of gemcitabine to tumor cells. Its mechanism involves inhibiting tumor-related inflammatory signaling pathways, particularly by blocking the TLR4/NF-κB signaling axis to reduce the expression of pro-tumor inflammatory factors, thereby suppressing the deterioration of the tumor microenvironment.
In hepatocellular carcinoma, apoptosis induced by 6-shoganeol is closely related to activation of castanase and also activates the ER stress signaling pathway. It promotes the expression of apoptosis-related genes by modulating the unfolded protein response (UPR) sensor PERK and its downstream target eIF2α, ultimately leading to cancer cell death.
6-Shoganeol has excellent blood-brain barrier penetration ability and demonstrates potential neuroprotective effects. It alleviates nerve damage and inflammatory responses by providing antioxidant, anti-inflammatory, and regulating neuronal apoptosis-related pathways. Related studies indicate that 6-shogaolol can inhibit the release of neuroinflammatory mediators, improve cognitive impairment, and have potential for treating neurodegenerative diseases such as Alzheimer's and Parkinson's.
6-Sgingerol regulates inflammatory signaling pathways through multiple targets, demonstrating significant anti-inflammatory effects. Its main mechanisms of action include inhibiting signaling pathways such as NF-κB and MAPK, and reducing the expression of pro-inflammatory cytokines such as TNF-α and IL-6. In addition, 6-gingerol can regulate the activity of immune cells, alleviate chronic inflammatory states, and is suitable as an adjunct treatment for inflammation-related diseases.
In studies related to hyperglycemia and diabetes, 6-gingerolol has shown effects in regulating blood glucose and improving insulin sensitivity. Its targets involve several key proteins, including EHMT2, UBP2, PAI1, AMPK, SGLT2, GCK, APP, BACE1, CES1, and PTPN1. By activating the AMPK signaling pathway and regulating the activity of glucose-metabolizing enzymes, 6-shoganeol helps lower blood sugar levels and improve metabolic disorders.
The multiple pharmacological effects of 6-shogaolol depend on its regulation of multiple signaling pathways and molecular targets:
TLR4/NF-κB signaling pathway: 6-Sgaenophenol blocks nuclear translocation of downstream NF-κB transcription factors by inhibiting TLR4 receptor activation, reducing pro-inflammatory gene expression, and suppressing tumor-related inflammation and immune evasion.
ER stress and UPR pathways: 6-Sgingerol activates the PERK-eIF2α axis, inducing unfolded protein responses and promoting cancer cell apoptosis. This mechanism is particularly pronounced in hepatocellular carcinoma cells.
AMPK signaling pathway: By activating AMPK, 6-shogunol promotes energy metabolism balance, enhances insulin sensitivity, and regulates glucose and lipid metabolism.
Caspasin-dependent apoptosis pathway: 6-Shogaolol induces activation of caspasins 3, 7, and 9, initiating programmed cell death.
Metabolic targets: EHMT2 (histone methyltransferase), UBP2 (ubiquitin-specific protease), PAI1 (plasminogen activator inhibitor 1), SGLT2 (sodium-glucose cotransporter 2), GCK (glucokinase), APP (amyloid precursor protein), BACE1 (β-secretase 1), CES1 (carboxylesterase 1), PTPN1 (protein tyrosine phosphatase 1B) and others are involved in its multiple regulatory and neuroprotective functions.
The druggability parameters of 6-shogaolol indicate that it has promising potential for drug development. The molecular weight is moderate (276.37), and the LogP value of 3.59 complies with the Lipinski rule, with good lipid solubility and biofilm penetration ability. The TPSA value is 49.69 Ų, and the number of hydrogen bond receptors is 3, indicating moderate molecular polarity and facilitating oral absorption.
In terms of toxicological evaluation, 6-shoganeol showed no hepatotoxicity, cardiotoxicity, or hERG channel inhibition; Ames-induced mutagenic test was negative, indicating high safety. Its high blood-brain barrier penetration ability makes it possible to treat neurological diseases.
Pharmacokinetic studies show that 6-gingerol is rapidly absorbed orally and widely distributed, with particularly high concentrations in liver and brain tissue. Metabolism mainly occurs through hepatic enzyme systems, and the activity of these metabolites still requires further research. Its half-life is moderate, and it has a certain degree of internal stability.
As a multifunctional natural product, 6-shogaolol shows broad clinical application prospects due to its multiple pharmacological effects including anti-cancer, neuroprotection, and anti-inflammatory effects. In tumor treatment, 6-shogaolol can serve as an adjunct drug to enhance the efficacy of chemotherapy drugs, reduce drug resistance, and improve patient outcomes. Its ability to regulate the tumor microenvironment offers new ideas for tumor immunotherapy.
In the field of neurodegenerative diseases, 6-shogaolol is expected to slow disease progression and improve cognitive function through its antioxidant and anti-inflammatory effects. Its excellent blood-brain barrier penetration makes it an ideal candidate for drug development for neurological diseases.
Additionally, 6-gingerol shows potential in regulating metabolic diseases such as diabetes and hyperglycemia, and may be developed as an adjunctive therapy for metabolic syndrome in the future.
However, clinical research on 6-shogaolol is still relatively limited, and further systematic clinical trials are needed to clarify its safety, effective dosage, and long-term efficacy. At the same time, improving bioavailability and targeting and developing novel drug delivery systems will also be key research priorities for the future.
6-Shogaolol, as an important active ingredient in ginger, has become a hot topic in natural product pharmacology research due to its unique chemical structure and diverse pharmacological activities. It demonstrates significant therapeutic potential in multiple fields, including anti-cancer, neuroprotection, anti-inflammation, and metabolic regulation. It has good druggability and high safety, laying a solid foundation for its drug development.
In the future, with deeper elucidation of molecular mechanisms and advances in clinical research, 6-shogaolol is expected to become a novel natural drug or adjunct for treating various diseases. Enhancing its pharmacokinetic optimization and dosage form innovation will further advance its clinical translational process and contribute more value to human health.
Shenshuai
Wenjing
Hedandan
