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Product name: Bergapten
Synonym name: Heraclin; Majudin; 5-Methoxypsoralen (obsol;)
Catalogue No.: BP0256
Cas No.: 484-20-8
Formula: C12H8O4
Mol Weight: 216.192
Botanical Source: Cnidium monnieri（L.）Cuss.
Physical Description:
Type of Compound: Coumarins
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.
Chengdu Biopurify Phytochemicals Ltd. is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine，TCM), Natural Active Pharmaceutical Ingredients worldwide.
The main services:
A. Supply active ingredients and reference standards of TCM, from mgs to kgs scale
B. Custom extraction and purification, target Herb Active Ingredients
C. Custom synthesis and semi-synthesis for Natural Active Ingredients
D. CR(contract research), CM(contract manufacture) and PD(process development) services from lab scale, pilot scale to commercial scale(GMP is also available)
E. TCM compounds library for drug screen,more than 3000 compounds available, many of them are rare and unique.
HPLC of Bergapten
HNMR of Bergapten
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
55.7600
1.8000
1.7400
High
No
Yes
Positive
Bergamot lactone (Bergapten), also known as 5-methoxypsoralen, is a natural furanocoumarin-type compound widely found in bergamot and other rutaceae plants. As a methoxy derivative of psoralen, bergamot lactone has attracted widespread attention in the field of natural product pharmacology in recent years due to its unique chemical structure and biological activity. Numerous studies have shown that bergamot lactone has significant liver-protective and anti-inflammatory effects, and plays an important role in regulating various inflammation-related signaling pathways. This paper will systematically review the chemical structure and physicochemical properties of bergamot lactone, plant origin and extraction methods, pharmacological activity, mechanism of action and molecular targets, druggability evaluation, and pharmacokinetic characteristics, and explore its clinical application prospects and future research directions.
The chemical name of bergamot lactone is 5-methoxyfuranocoumarin, with the molecular formula C12H8O4 and a molecular weight of 216.19. Its structure is based on the furanocoumarin-based framework of psoralen, with a methoxy substituent introduced at position 5, forming a unique 5-methoxypsoralen structural unit. This structure gives bergamot lactones strong photosensitivity and bioactivity.
In terms of physicochemical properties, bergamot lactone has a LogP value of 1.8, showing moderate lipid solubility that benefits its cell membrane penetration capability. Its topological polar surface area (TPSA) is 55.76 Ų, and it has 4 hydrogen bond acceptors, indicating that its molecules possess certain polarity and hydrogen bond formation capabilities, facilitating binding to biological macromolecule targets. Bergamot lactone can cross the blood-brain barrier, suggesting its potential application value in central nervous system diseases. Toxicological evaluation showed no hepatotoxicity or hERG channel inhibition, but the Ames test was positive, suggesting a possible genotoxicity risk and requiring in-depth safety evaluation before clinical use.
Bergamot lactones are mainly found in Rutaceae plants, especially in the peel and essential oil of bergamot (Citrus bergamia risso et Poiteau). Additionally, plants such as Psoralea (Psoralea corylifolia) also contain this compound. Due to its wide distribution, bergamot lactone has become an important active ingredient in many traditional Chinese medicinal materials and aromatic plants.
The extraction methods mainly include solvent extraction and chromatographic separation techniques. Traditional extraction processes use ethanol or methanol as solvents, with crude extracts obtained by reflux or ultrasound-assisted extraction, followed by purification using silica gel column chromatography, high-performance liquid chromatography (HPLC), and other technologies. In recent years, supercritical CO2 extraction technology, due to its green environmental protection and strong selectivity, has also been applied to the extraction and separation of bergamot lactones, significantly improving extraction efficiency and purity.
Research on the pharmacological activity of bergamot lactone mainly focuses on its anti-inflammatory, hepatoprotective, antioxidant, and photosensitive therapies.
Anti-inflammatory activity
Bergamot lactone regulates various inflammation-related signaling pathways and inhibits the release of pro-inflammatory cytokines, demonstrating significant anti-inflammatory effects. Both in vitro and in vivo experiments have confirmed that it can reduce the expression of inflammatory mediators such as TNF-α, IL-6, and IL-1β, thereby alleviating inflammatory responses.
Liver-protective effects
Multiple studies have shown that bergamot lactone has a protective effect against drug- or toxin-induced liver damage. Its mechanism involves antioxidant stress, inhibition of hepatocyte apoptosis, and regulation of liver metabolic enzyme activity, thereby alleviating inflammation and fibrosis in liver tissue.
Antioxidant and cell protection
Bergamot lactone can activate the NFE2L2 (Nrf2) signaling pathway, enhance the expression of intracellular antioxidant enzymes, scavenge reactive oxygen species (ROS), and protect cells from oxidative damage.
Photosensitivity treatment potential
As a furanocoumarin-class compound, bergamot lactone has certain photosensitizing activity and has been studied for use in photodynamic therapy (PDT), especially showing potential in the treatment of skin diseases such as psoriasis and vitiligo.
The biological effects of bergamot lactone mainly occur through interactions with multiple key molecular targets and involve regulation of multiple signaling pathways.
TLR4 (Toll-like receptor 4)
Bergamot lactone can inhibit TLR4-mediated inflammatory signaling, reduce downstream NF-κB activation, and decrease pro-inflammatory factor expression, thereby alleviating inflammatory responses.
PTPN1 (protein tyrosine phosphatase 1B)
By regulating PTPN1 activity, bergamot lactone participates in the regulation of cellular signal transduction, affecting metabolic and inflammatory processes.
STAT3 (Signal Transduction and Transcription Activation Factor 3)
Bergamot lactone inhibits STAT3 phosphorylation, blocks its nuclear translocation, suppresses the expression of pro-inflammatory genes, and exerts anti-inflammatory and antitumor effects.
ALOX15 and ALOX5 (lipoxygenases 15 and 5)
These two lipoxygenases are involved in the synthesis of inflammatory mediators, and bergamot lactone reduces their production by inhibiting their activity.
PRKCA (protein kinase Cα)
Bergamot lactone regulates the PRKCA signaling pathway, affecting cell proliferation and apoptosis.
NFE2L2（Nrf2）
Bergamot lactone activates the Nrf2 signaling pathway, enhancing antioxidant defenses and reducing oxidative stress damage.
PIK3CG (phosphatidyl-inositol 3-kinase γ)
By modulating the PI3K/AKT pathway, bergamot lactone affects cell survival and inflammatory response.
PLA2G2A (phospholipase A2) and MAPK1 (mitogen-activated protein kinase 1)
Involved in lipid metabolism and signal transduction in cell membranes, bergamot lactone modulates inflammation and cellular stress responses by regulating these targets.
In summary, bergamot lactone exerts its broad biological functions through multi-target and multi-pathway synergistic effects, especially showing significant potential in the prevention and treatment of inflammatory diseases.
The druggability parameters of bergamot lactone indicate that it has promising potential for drug development. The molecular weight is moderate (216.19), with a LogP value of 1.8, indicating suitable lipophilic properties, which facilitate oral absorption and cell membrane penetration. The TPSA value is 55.76 Ų and the number of hydrogen bond receptors is 4, which is beneficial for its binding affinity with target proteins.
The high permeability of the blood-brain barrier suggests its potential in treating central nervous system-related diseases. Toxicologically, there was no hepatotoxicity or hERG suppression, reducing the risk of cardiotoxicity, but a positive Ames test suggested the need for potential genotoxicity, requiring further toxicological and safety studies.
Pharmacokinetic studies show that bergamot lactone is well absorbed orally, widely distributed in the body, metabolized mainly through hepatic enzyme systems, and excreted primarily by the kidneys. It has a moderate half-life and a certain degree of in vivo stability, but photosensitivity may affect its in vivo stability and duration of efficacy, which needs to be addressed through formulation improvements and optimized administration regimens.
Bergamot lactone, due to its remarkable anti-inflammatory and hepatoprotective effects, has broad application prospects in inflammatory diseases such as hepatitis, rheumatoid arthritis, and metabolic syndrome. Its multi-target mechanism of action provides a theoretical basis for the development of novel multi-target anti-inflammatory drugs.
Moreover, the photosensitive properties of bergamot lactone give it great potential in photodynamic therapy, especially as an adjunct treatment for skin diseases and certain tumors. Future research can further explore its synergistic effects with other drugs and innovative formulations to improve efficacy and safety.
However, the genotoxic risks and photosensitive side effects of bergamot lactone still require close attention. Systematic toxicological assessment and preclinical safety studies are key steps in its clinical translation. At the same time, in-depth analysis of its pharmacokinetic characteristics and metabolic pathways helps optimize administration regimens and dosage form design.
In the future, modern medicinal chemistry and molecular biology techniques can be used to design bergamot lactone derivatives to improve their pharmacokinetic properties and safety, expanding their clinical applications. Additionally, based on its multi-target regulatory characteristics and combined with precision medicine concepts, developing personalized treatment strategies targeting specific inflammatory pathways will be a research hotspot.
Bergamot lactone, as a natural furanocoumarin, with a unique structure and multiple bioactive properties, demonstrates significant anti-inflammatory, liver-protecting, and antioxidant effects. By regulating multiple key molecular targets such as TLR4, STAT3, and Nrf2, it exerts multi-target synergistic therapeutic effects, showing promising drug development potential and broad clinical application prospects. Although its genotoxicity and photosensitivity pose certain challenges, with continuous advances in extraction and purification technology, pharmacokinetic optimization, and safety evaluation, bergamot lactone is expected to become an important candidate molecule in natural product drug development. Future research should focus on in-depth mechanism analysis, structural optimization, and clinical translation, promoting its application in inflammatory diseases and related fields.
Shenshuai
Wenjing
Hedandan
