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Tulipalin A Sale

(Synonyms: 郁金香素A; α-Methylene butyrolactone) 目录号 : GC66063

2-Methylenebutyrolactone (Tulipalin A, MBL, α-methylene-γ-butyrolactone), also known as α-methylene-γ-butyrolactone (MBL) (Tulipalin A), belongs to the class of sesquiterpene lactone family and is considered as cyclic analog of most common vinyl monomer methyl methacrylate (MMA).

Tulipalin A Chemical Structure

Cas No.:547-65-9

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产品描述

2-Methylenebutyrolactone (Tulipalin A, MBL, α-methylene-γ-butyrolactone), also known as α-methylene-γ-butyrolactone (MBL) (Tulipalin A), belongs to the class of sesquiterpene lactone family and is considered as cyclic analog of most common vinyl monomer methyl methacrylate (MMA).

After exposure of Jurkat T cells to 2-Methylenebutyrolactone (Tulipalin A , TUPA) for 72 h, a dose dependent toxicity is detected. Concentrations higher than 20 μM lead to a significant reduction of viable cells. Compared to vehicle-treated control cells, concentrations of 47.6 and 26.8 μM decrease the cell viability significantly by 50% (IC50) and 10% (IC10), respectively. In contrast, THP-1 cells are less sensitive toward TUPA. Concentrations >41 μM lead to a significant reduction of viable cells. IC10 is calculated with 50 μM, whereas a concentration of 83 μM is necessary to decrease the cell viability to 50% (IC50). In Jurkat T cells, four proteins responsible for the de novo purine synthesis, namely phosphoribosylformylglycinamidine synthase (PFAS), GMP synthase (GMPS), and ribosephosphate pyrophosphokinases 1 and 2 (PRPS1/2) are increased through TUPA treatment. Glutamine is also increased after TUPA treatment. In addition to the proteins belonging to the purine synthesis pathway, the abundances of proteins for DNA synthesis and repair (XRCC5, XRCC6, MCM3, MCM6, MCM7, TRA1) are also increased/induced during the treatment. While in THP-1 cells, no indication for higher purine synthesis induced by TUPA in subtoxic concentrations is discovered. TUPA induces the expression of proteins in Jurkat T cells responsible for cell stress, drug response, and protein folding: HYOU1, PDIA3, and DNAJB11. Additionally, the treatment with TUPA leads to the induction of three heat shock proteins (HSP90AA1, HSP90AB1, and HSP90B1) and three proteins belonging to the TRiC complex (CCT3,6,8) that are also responsible for proper protein folding. Treatment with TUPA leads to the induction of ROS that have adverse effects on Jurkat T cells and evokes slight cell stress responses in THP-1 cells. TUPA has influence on proteins in Jurkat T cells that contribute to different immune-specific, especially immunostimulating, reactions as allergic contact dermatitis. In THP-1 cells, no proteins regarding immune-specific reactions are up- or downregulated due to TUPA treatment[1].

[1] Zwicker P, et al. Proteomics. 2016, 16(23):2997-3008.

Chemical Properties

Cas No. 547-65-9 SDF Download SDF
别名 郁金香素A; α-Methylene butyrolactone
分子式 C5H6O2 分子量 98.1
溶解度 DMSO : ≥ 100 mg/mL (1019.37 mM) 储存条件 Store at -20°C, protect from light, stored under nitrogen
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1 mg 5 mg 10 mg
1 mM 10.1937 mL 50.9684 mL 101.9368 mL
5 mM 2.0387 mL 10.1937 mL 20.3874 mL
10 mM 1.0194 mL 5.0968 mL 10.1937 mL
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Research Update

Botanical Briefs: Tulipalin A

Cutis 2022 Sep;110(3):145-149.PMID:36446113DOI:10.12788/cutis.0613.

Contact dermatitis is a common issue for many floral employees. Tulips are one of the most common causes of hand dermatitis. Tulipalin A is the main sensitizer in tulips and also is found in the Peruvian lily. "Tulip fingers" is the most typical clinical presentation of hand dermatitis from tulips and is characterized by erythematous scaling seen in periungual skin and between the first and second fingertips of the dominant hand. The best prevention for tulip contact dermatitis is to avoid exposure to the inciting plants or use nitrile gloves.

Tulipalin A induced phytotoxicity

Int J Crit Illn Inj Sci 2014 Apr;4(2):181-3.PMID:25024947DOI:10.4103/2229-5151.134187.

Tulipalin A induced phytotoxicity is a persistent allergic contact dermatitides documented in floral workers exposed to Alstroemeria and its cultivars.[1] The causative allergen is Tulipalin A, a toxic glycoside named for the tulip bulbs from which it was first isolated.[2] The condition is characterized by fissured acropulpitis, often accompanied by hyperpigmentation, onychorrhexis, and paronychia. More of the volar surface may be affected in sensitized florists. Dermatitis and paronychia are extremely common conditions and diagnostic errors may occur. A thorough patient history, in conjunction with confirmatory patch testing with a bulb sliver and tuliposide A exposure, can prevent misdiagnosis. We report a case of Tulipalin A induced phytotoxicity misdiagnosed as an unresolved tinea manuum infection in a patient evaluated for occupational exposure.

A proteomic approach for the identification of immunotoxic properties of Tulipalin A

Proteomics 2016 Dec;16(23):2997-3008.PMID:27687999DOI:10.1002/pmic.201600130.

The immune system is permanently exposed to several environmental influences that can have adverse effects on immune cells or organs leading to immunosuppression or inappropriate immunostimulation, called direct immunotoxicity. The natural compound Tulipalin A (TUPA), a lactone with α-methylene-γ-butyrolactone moiety, can influence the immune system and lead to allergic contact dermatitis. This in vitro study focused on effects of TUPA using two immune cell lines (Jurkat T cells and THP-1 monocytes). To evaluate the immunotoxic potential of the compound, a proteomic approach applying 2D gel electrophoresis and MALDI-TOF/TOF-MS in combination with metabolomic analysis was used after exposure of the cells to IC10 of TUPA. THP-1 cells showed a strong robustness to TUPA treatment since only five proteins were altered. In contrast, in Jurkat T cells an increase in the abundance of 66 proteins and a decrease of six proteins was determined. These intracellular proteins were mapped to biological processes. Especially an accumulation of chaperones and an influence on the purine synthesis were observed. The changes in purine synthesis were confirmed by metabolomic analysis. In conclusion, the data indicate possible target processes of low doses of TUPA in Jurkat T cells and provides knowledge of how TUPA affects the functionality of immune cells.

A simple HPLC method for the isolation and quantification of the allergens tuliposide A and Tulipalin A in Alstroemeria

Contact Dermatitis 1995 Apr;32(4):199-203.PMID:7600774DOI:10.1111/j.1600-0536.1995.tb00669.x.

A practical, rapid, reliable and sensitive method for the isolation and determination of the allergens tuliposide A and alpha-methylene-gamma-butyrolactone (Tulipalin A), by reversed-phase high-performance liquid chromatography (RP-HPLC), has been developed in order to select Alstroemeria species for breeding purposes. From the aqueous extracts of flowers, stems and leaves, of several Alstroemeria species, the contents of 6-tuliposide A and Tulipalin A were determined by isocratic RP-HPLC, using distilled water as mobile phase. The compounds were detected by an UV detector at 208 nm. Differences in 6-tuliposide A and Tulipalin A content were found among the species investigated, with the highest concentrations in stems and flowers. The absence of other tuliposides (e.g., 1-tuliposide A, 1- and 6-tuliposide B) in extracts was proven by TLC, RP-HPLC, 1H- and 13C-NMR. 6-Tuliposide A and Tulipalin A were identified by 1H- and 13C-NMR and comparison with authentic material, respectively. With this HPLC method, it is possible to investigate a large number of plants for their contents of tuliposide A and Tulipalin A, within a minimum of time, and to isolate them directly from aqueous extracts.

Initiated Chemical Vapor Deposition (iCVD) of Bio-Based Poly(Tulipalin A) Coatings: Structure and Material Properties

Polymers (Basel) 2022 Sep 23;14(19):3993.PMID:36235940DOI:10.3390/polym14193993.

A solvent-free route of initiated chemical vapor deposition (iCVD) was used to synthesize a bio-renewable poly(α-Methylene-γ-butyrolactone) (PMBL) polymer. α-MBL, also known as Tulipalin A, is a bio-based monomer that can be a sustainable alternative to produce polymer coatings with interesting material properties. The produced polymers were deposited as thin films on three different types of substrates-polycarbonate (PC) sheets, microscopic glass, and silicon wafers-and characterized via an array of characterization techniques, including Fourier-transform infrared (FTIR), proton nuclear magnetic resonance spectroscopy (1H NMR), ultraviolet visible spectroscopy (UV-vis), differential scanning calorimetry (DSC), size-exclusion chromatography (SEC), and thermogravimetric analysis (TGA). Optically transparent thin films and coatings of PMBL were found to have high thermal stability up to 310 °C. The resulting PMBL films also displayed good optical characteristics, and a high glass transition temperature (Tg~164 °C), higher than the Tg of its structurally resembling fossil-based linear analogue-poly(methyl methacrylate). The effect of monomer partial pressure to monomer saturation vapor pressure (Pm/Psat) on the deposition rate was investigated in this study. Both the deposition rate and molar masses increased linearly with Pm/Psat following the normal iCVD mechanism and kinetics that have been reported in literature.