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Product name: 8-Prenylnaringenin
Synonym name: (+/-)-8-Prenylnaringenin; 68682-02-0
Catalogue No.: SBP02804
Cas No.: 53846-50-7
Formula: C20H20O5
Mol Weight: 340.375
Botanical Source:
Physical Description:
Type of Compound: Flavonoids
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.
The product could be supplied from milligrams to grams
Inquire for bulk scale.
For Reference Standard and R&D, Not for Human Use Directly.
Description:
8-Prenylnaringenin is a phytoestrogen with high estrogenic activity, it shows more potent effects on promoting osteoblastic bone formation and inhibiting osteoclastic bone resorption by ERα instead of ERβ than the two classic phytoestrogens: genistein and daidzein. 8-Prenylnaringenin at all assayed doses (0.001-20 µM) presumably improves mitochondrial function, whereas a high dose of XN (5 µM) worsens the functionality of this organelle.
References:
Strahlenther Onkol. 2015 May;191(5):429-36.
8-prenylnaringenin and tamoxifen inhibit the shedding of irradiated epithelial cells and increase the latency period of radiation-induced oral mucositis : cell culture and murine model.
The major component in the pathogenesis of oral radiation-induced mucositis is progressive epithelial hypoplasia and eventual ulceration. Irradiation inhibits cell proliferation, while cell loss at the surface continues. We conceived to slow down this desquamation by increasing intercellular adhesion, regulated by the E-cadherin/catenin complex. We investigated if 8-Prenylnaringenin (8-PN) or tamoxifen (TAM) decrease the shedding of irradiated human buccal epithelial cells in vitro and thus delay the ulcerative phase of radiation-induced mucositis in vivo.
METHODS AND RESULTS:
In vitro, aggregates of buccal epithelial cells were irradiated and cultured in suspension for 11 days. 8-PN or TAM were investigated regarding their effect on cell shedding. In vivo, the lower tongue surface of mice was irradiated with graded single doses of 25 kV X-rays. The incidence, latency, and duration of the resulting mucosal ulcerations were analyzed after topical treatment with 8-PN, TAM or solvent. 8-PN or TAM prevented the volume reduction of the irradiated cell aggregates during the incubation period. This was the result of a higher residual cell number in the treated versus the untreated irradiated aggregates. In vivo, topical treatment with 8-PN or TAM significantly increased the latency of mucositis from 10.9 to 12.1 and 12.4 days respectively, while the ulcer incidence was unchanged.
CONCLUSIONS:
8-PN and TAM prevent volume reduction of irradiated cell aggregates in suspension culture. In the tongues of mice, these compounds increase the latency period. This suggests a role for these compounds for the amelioration of radiation-induced mucositis in the treatment of head and neck tumors.
Planta Med. 2015 Mar;81(4):305-11.
Neurodifferentiating potential of 8-prenylnaringenin and related compounds in neural precursor cells and correlation with estrogen-like activity.
Neurodegenerative diseases are an increasing burden for our ageing societies; there is an as yet unmet need for the development of effective therapies. Neurogenesis, i.e., the generation of new neurons in the adult brain from neural stem cells, has received increasing attention since it offers the potential for endogenous brain repair and functional regeneration. Adult neurogenesis is partially under the control of sex hormones such as estradiol, and boosting neurogenesis with estradiol in animals correlates with cognitive improvement. 8-Prenylnaringenin imitates as highly potent phytoestrogen the effects of estradiol.
METHODS AND RESULTS:
Here, we studied the potential of 8-Prenylnaringenin, 6-prenylnaringenin, and related compounds on differentiation induction in vitro using neural precursor cells transiently transfected with a doublecortin promoter luciferase construct, which was recently shown to indicate neuronal fate and differentiation. The flavanones 8-Prenylnaringenin and 6-prenylnaringenin showed slight activity in this assay but significant activity by immunostaining. Although the estrogen-like activities of 8-Prenylnaringenin and 6-prenylnaringenin are very different, the activity in differentiation induction is similar. Interestingly, also some prenylflavonoids with extended prenyl groups, e.g., a geranyl group, showed increased differentiation activity, while estrogen-like activity is decreased.
CONCLUSIONS:
This allows the conclusion that estrogen-like activity of prenylflavanones does not correlate directly with the activity of differentiation induction in neural precursor cells.
HPLC of 8-Prenylnaringenin
HNMR of 8-Prenylnaringenin
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
94.8300
3.5000
3.2000
Low
Unknown
Unknown
Unknown
Unknown
Unknown
Unknown
8-Prenylnaringenin (8-Prenylnaringenin, hereinafter referred to as 8-PN) is a natural product of isopentylflavonoids with significant biological activity, mainly derived from hops (Humulus lupulus). ) is separated and obtained. As an orally active compound, 8-PN has attracted attention for its multi-target and multi-pathway pharmacological effects, especially showing broad research and application prospects in fields such as antioxidant properties, bone health, metabolic diseases, and tumor treatment. This paper aims to systematically review the chemical structure, origin, pharmacological activity, mechanism of action, and druggability evaluation of 8-PN, exploring its potential and future development directions in preclinical research.
8-PN has a chemical structure of isopentenyl-modified flavonoids, with the molecular formula C₂₀H₂₄O₅ and a molecular weight of 340.37. Its structural feature is that the 8th position of the naringetin skeleton connects to an isopentyl side chain, and this structural modification significantly enhances its bioactivity and lipid solubility. In terms of physicochemical properties, 8-PN has a LogP value of about 3.5, indicating moderate lipid solubility, which facilitates cell membrane penetration and oral absorption. The topological pole surface area (TPSA) is 94.83 Ų, and the number of hydrogen bond acceptors is 5, suggesting that it possesses certain hydrophilicity and binding ability in organisms. The blood-brain barrier has a relatively low penetration capacity, suggesting that its role in the central nervous system may be limited. Currently, there is no clear data on its hepatotoxicity, cardiotoxicity, or safety indicators such as hERG channel inhibition, and further systematic evaluation is needed.
8-PN mainly comes from the flower spikes of hops (Humulus lupulus), which are an indispensable raw material in beer brewing and a natural reservoir of various bioactive flavonoids. Although the content of 8-PN is not as high as other active hop components such as picric acid, its biological effects are more significant. The extraction method typically uses organic solvents (such as ethanol and methanol) for extraction combined with liquid chromatography (HPLC) separation and purification technology to obtain high-purity 8-PN. In recent years, supercritical CO₂ extraction and membrane separation technologies have also been applied to improve extraction efficiency and purity. In addition, research on biosynthetic pathways provides a theoretical basis for the bioengineering synthesis of 8-PN, with prospects for large-scale production in the future.
8-PN activates the Nrf2 (nuclear factor 2-related factor) signaling pathway, upregulating various antioxidant enzymes such as superoxide dismutase (SOD1, SOD2), glutathione peroxidase (GPX1), catalase (CAT), and heme oxygenase 1 (HMOX1), effectively reducing intracellular reactive oxygen species (ROS) levels and alleviating oxidative stress damage. Additionally, 8-PN can regulate matrix metalloproteinase (MMP1, MMP3) activity, protecting extracellular matrix stability and delaying tissue aging.
As a natural plant estrogen, 8-PN has a significant regulatory effect on bone metabolism. It promotes bone formation and inhibits bone resorption by activating estrogen receptor α (ESR1) and Sirt1 protein. 8-PN can also activate the AMPK pathway, regulate the expression balance of osteoprotectin (OPG, TNFRSF11B) and nuclear factor κB receptor-activating factor ligand (RANKL, TNFSF11), inhibit osteoclast activity, and prevent bone loss. Animal model studies have shown that 8-PN can effectively improve bone density and slow the progression of osteoporosis.
8-PN regulates lipid metabolism-related gene expression by activating the AMPK signaling pathway, including peroxisome proliferator-activated receptor γ (PPARγ), fatty acid synthase (FASN), adiponectin receptor 1 (ADIPOR1), and lipase-activated protein kinase (LIPE), promoting fat breakdown and energy metabolism. It showed significant effects on weight control and adipose tissue improvement in obese model animals, suggesting its potential application value in metabolic syndrome and related diseases.
8-PN exhibits multi-target anticancer activity in glioblastoma and colon cancer. It blocks tumor cell proliferation and survival signals by inhibiting the PI3K/Akt/mTOR signaling pathway; At the same time, it regulates the activity of cyclin-dependent kinases (CDK2, CDK4), inducing tumor cell cycle arrest and apoptosis. In colon cancer, 8-PN also regulates Wnt/β-catenin (CTNNB1) signaling, promotes the restoration of tumor suppressor protein p53 (TP53) function, and suppresses tumor progression. Additionally, the anti-angiogenic effect of 8-PN inhibits the expression of vascular endothelial growth factor receptor 2 (KDR), restricting tumor angiogenesis and blocking tumor nutrient supply.
8-PN has activity in regulating luteinizing hormone (LH) and follicle-stimulating hormone (FSH) levels, demonstrating the endocrine regulatory function of plant estrogens. This characteristic makes it of great significance in the study of female menopausal syndrome and related endocrine disorders.
The multi-target mechanism of 8-PN mainly involves the following key pathways:
PI3K/Akt signaling pathway: 8-PN activates PI3K (PIK3CA) and its downstream Akt (AKT1), regulating cell survival, metabolism, and proliferation. In tumor cells, 8-PN achieves antiproliferative and pro-apoptotic effects by inhibiting this pathway.
AMPK pathway: As an energy-sensing enzyme, AMPK (PRKAA1) is activated by 8-PN, promoting lipid metabolism and mitochondrial function, improving metabolic abnormalities and obesity.
Regulation of oxidative phosphorylation complexes: 8-PN upregulates mitochondrial oxidative phosphorylation complexes (II, III, V), enhancing cellular energy metabolism efficiency, reducing ROS production, and protecting cells from oxidative damage.
Sirt1 activation: By activating the deacetylating enzyme Sirt1,8-PN, it regulates apoptosis, inflammation, and metabolic homeostasis, promoting bone and muscle health.
Nrf2 antioxidant pathway: 8-PN activates Nrf2, inducing antioxidant enzyme expression and enhancing cellular antioxidant defense.
Wnt/β-catenin signaling: In colon cancer, 8-PN regulates CTNNB1 activity, affecting cell proliferation and differentiation.
Cell cycle regulation: By modulating CDK2 and CDK4 activities, 8-PN induces cell cycle arrest and inhibits tumor cell proliferation.
Angiogenesis inhibition: suppresses KDR expression and blocks tumor angiogenesis.
The synergistic effects of these multi-target, multi-pathway mechanisms enable 8-PN to demonstrate significant therapeutic potential across various disease models.
The molecular weight and lipophilic parameters of 8-PN meet the basic requirements for oral small molecule drugs and have good cell membrane penetration. However, its low blood-brain barrier penetration limits its application in central nervous system diseases. A moderate number of hydrogen bond receptors facilitates binding to target proteins. Currently, systematic data on safety indicators such as hepatotoxicity, cardiotoxicity, and genotoxicity (Ames assay) are lacking, and further toxicological studies are needed.
Pharmacokinetics, previous studies have shown that 8-PN has good bioavailability after oral administration, but its metabolic pathways and distribution in vivo are not yet fully understood. The 8-PN content in hops is relatively low, and its metabolism in vivo may involve extensive involvement of liver enzyme systems. Future research should combine pharmacokinetics and pharmacodynamics to optimize dosage forms and administration regimens to enhance clinical application potential.
As a natural plant estrogen, 8-PN has shown broad application prospects in osteoporosis prevention and treatment, metabolic disease regulation, and tumor adjuvant therapy. Its antioxidant and anti-inflammatory properties give it potential value in the prevention and treatment of chronic degenerative diseases and geriatric diseases. Especially in the management of female menopausal syndrome, 8-PN may be a safe and effective alternative to hormone therapy.
Future research should focus on the following areas:
Safety evaluation: Systematic toxicological and long-term safety studies are conducted to clarify the spectrum of toxic side effects of 8-PN.
Pharmacokinetic optimization: Enhancing bioavailability and targeting through structural modification or formulation technologies.
In-depth Mechanism Analysis: Using multi-omics techniques to reveal its network of effects, promoting the development of precision treatment strategies.
Clinical trial advancement: Designing reasonable clinical studies to verify efficacy and safety in osteoporosis, metabolic syndrome, and tumor treatment.
Biosynthesis and industrialization: Develop biosynthesis technology to achieve large-scale production of 8-PN, reduce costs, and promote clinical translation.
8-isopentenylnaringin, as a versatile natural isoprenyl flavonoid, demonstrates potential in fields such as antioxidant properties, bone health, metabolic regulation, and anti-tumor due to its unique chemical structure and multi-target pharmacological activity. Although current understanding of its safety and pharmacokinetics is still insufficient, with the continuous development of modern pharmacology and natural product chemistry, 8-PN is expected to become an important candidate for natural product drug development. In the future, through in-depth mechanistic research and clinical validation, 8-PN is expected to provide new strategies and options for the prevention and treatment of related diseases.
Shenshuai
Wenjing
Hedandan
