Disease relevance of Tulipalin A

• Preliminary in vitro evaluation indicated that the 7-[4-(2-hydroxyiminoethyl)piperazin-1-yl] derivatives 3b-e possess distinct cytotoxicity profiles as compared with their alpha-methylene-gamma-butyrolactone counterparts, 4b,e: i.e., excellent activities against the renal cancer subpanel [1].
• Allergic contact dermatitis due to sesquiterpene lactones. A comparative study of human and animal sensitivity to alpha-methylene-gamma-butyrolactone and derivatives [2].
• The possibility that airborne tulipalin A from Alstroemeria could be a source of airborne contact dermatitis is discussed [3].
• Alpha-methylene-gamma-butyrolactone is better known as the cause of both Alstroemeria dermatitis in retail florists and tulip finger in wholesale floral workers who handle the bulbs [4].

High impact information on Tulipalin A

• In this study, CYL-19 s and CYL-26z, two synthetic alpha-methylene-gamma-butyrolactone derivatives, were shown to inhibit the tumor necrosis factor-alpha (TNF-alpha)-induced intercellular adhesion molecule-1 (ICAM-1) expression in human A549 alveolar epithelial cells and the adhesion of U937 cells to these cells [5].
• The biological activity of compound 9 obtained by introducing an alpha-methylene-gamma-butyrolactone group into 3-(4-hydroxyphenyl)propionic acid, 1, was studied for possible effects on HL-60 cells, murine splenocytes, and human peripheral mononuclear cells (PBMC) [6].
• C75 [4-methylene-2-octyl-5-oxo-tetrahydro-furan-3-carboxylic acid] is an alpha-methylene-butyrolactone that has been characterized as both an inhibitor of fatty acid synthase and more recently, an activator of CPT-1 (Thupari et al., 2002) [7].
• The alpha-methylene-gamma-butyrolactone group is necessary for cross-reaction, but to be active, it has first to be substituted [2].
• The results of this study are as follows (1) for the vasorelaxing activity, coumarin-7-yl alpha-methylene-gamma-butyrolactone 6d, with an IC50 value of 9.4 microM against pig coronary arterial contraction induced by KCl, is a more active vasorelaxant than its coumarin-4-yl counterpart 6a and its gamma-methyl congener 1 [8].

Chemical compound and disease context of Tulipalin A

• Direct release of the allergen tulipalin A from Alstroemeria cut flowers: a possible source of airborne contact dermatitis [3]?
• The content of the allergens 6-tuliposide A and tulipalin A was also determined by RP-HPLC and the possibility that tuliposide D is a further causative agent of allergic contact dermatitis in Alstroemeria is discussed [9].
• Chemicals with a well-known capacity to induce contact dermatitis in man like 2,4-dinitro-1-chlorobenzene, alpha-methylene-gamma-butyrolactone, p-phenylenediamine, 5-nitro-2-furaldehyde semicarbazone, 2-mercapto-benzothiazol and 1,3-dibutyl-2-thiourea caused marked PLN reactions, while the non-sensitizer 2,4-dichloro-1-nitrobenzene failed to do so [10].

Biological context of Tulipalin A

• Inhibition of ICAM-1 gene expression, monocyte adhesion and cancer cell invasion by targeting IKK complex: molecular and functional study of novel alpha-methylene-gamma-butyrolactone derivatives [5].
• The structure-activity relationship indicated that alpha-methylene-gamma-butyrolactone is required for the inhibitory effect [11].

Anatomical context of Tulipalin A

• Certain alpha-methylene-gamma-butyrolactone derivatives of coumarin, naphthalene, and quinoline were synthesized and evaluated for vasorelaxing effects on isolated rat thoracic aorta [12].

Associations of Tulipalin A with other chemical compounds

• 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 [13].
• Alpha-methylene-gamma-butyrolactone also showed inhibitory activity (IC50 = 9.6 microM), while mokko lactone and watsonol A etc., reductants of the alpha-methylene-gamma-butyrolactone moiety by NaBH4 or DIBAL, and a 2-mercaptoethanol adduct of dehydrocostus lactone showed little activity (IC50 > or = 18 microM) [14].

Gene context of Tulipalin A

• Besides the alpha-methylene-gamma-butyrolactone moiety the epoxy group in the acyl residue might take part in the NF-kappa B inhibitory activity of sesquiterpene lactones [15].

Analytical, diagnostic and therapeutic context of Tulipalin A

• Several compounds containing the alpha-methylene-gamma-butyrolactone moiety have been tested on human volunteers and on guinea-pigs; the animals were experimentally sensitized by alantolactone, isoalantolactone and laurel oil [2].
• Results of a patch test to alpha-methylene-gamma-butyrolactone were strongly positive, and the patient determined that the exposure had occurred when he stripped leaves from the tulip stems to arrange cut flowers [4].

References