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Monographs of essential oils that have caused contact allergy / allergic contact dermatitis
Published in Anton C. de Groot, Monographs in Contact Allergy, 2021
Formerly, the most frequent side effect of bergamot oil present in cosmetics was phototoxicity due to its content of furocoumarines, notably 5-methoxypsoralen (bergapten). Its presence in fragrances caused ‘Berloque’ pigmentation, sometimes preceded by erythema, classically assuming a drop-like or pendant-like configuration over the sides of the neck in adult females from perfumes dripping down. However, pigmentation of the face from perfumes or aftershaves or at other body parts where perfumes were applied have also been observed. Concentrations of 12 ppm of 5-methoxypsoralen could induce phototoxicity with hyperpigmentation (24). Already in the 1970s, the incidence of such reactions decreased from lowering the concentration of bergamot oil in perfumes and using bergapten-free oil. Yet, at the end of the 1970s, 8 cases of phototoxic hyperpigmentation from 5-methoxypsoralen in perfumes were seen in one clinic in Lebanon (24).
Influence of Light on Essential Oil Constituents
Published in K. Hüsnü Can Başer, Gerhard Buchbauer, Handbook of Essential Oils, 2020
Marie-Christine Cudlik, Gerhard Buchbauer
Bergapten (= 5-methoxypsoralen) causes phototoxic reactions when skin treated with bergamot EO is exposed to UV light. The laser photolysis at 10 Hz by Moulin et al. (1995) eliminated 35% of the bergapten in the EO after 1 hour, and 60% after 2 hours of irradiation. Other constituents were not affected, and the process seems to be irreversible due to unchanging absorption spectra several days after the phototreatment (Moulin et al., 1995). In their study, the authors also aimed for the destruction of safrole in the oil of sassafras, which can be obtained from the roots of Sassafras albidum (Nutt.) Nees (Lauraceae) or some members of the genus Ocotea, which are closely related. Furthermore, it can be sourced from Piper hispidinervum L. (Piperaceae), the EO of which also contains high levels of safrole (Rocha and Chau Ming, 1999). Interestingly, the trade of plant extracts rich in safrole is restricted in the European Union, due to the fact that safrole is a precursor in the production of 3,4-methylendioxy-N-methylamphetamin (MDMA) (EMCDDA, 2016). Additionally, safrole is known to have carcinogenic effects. The sassafras EO was subdued to laser photolysis, and with the help of chromatograms before and after, the authors could verify the complete disappearance of the safrole peak. Instead, three new peaks appeared, which can be assumed to be those of short fragments of safrole, because of their short retention times and because laser photolysis generally creates smaller products in comparison to UV photoreactions, a fact attributed to the large difference in energy (Moulin et al., 1995).
Photochemotherapy
Published in Henry W. Lim, Nicholas A. Soter, Clinical Photomedicine, 2018
Psoralens belong to the furocoumarin group of compounds. The parent compound psoralen, and many of its derivatives, are widely distributed in plants and fruit such as limes, celery, figs, and lemons. Thus, psoralens are ingested in small quantities in a normal diet; the biological significance of this is unknown. Four psoralens are used for therapeutic purposes (Fig. 1). Methoxsalen, or 8-methoxypsoralen, which is obtained from the seeds of a plant called Ammi majus that grows in the Nile Valley, is the most commonly used psoralen. Trioxsalen, or 4, 5′-8-trimethylpsoralen, is a synthetic compound used for the treatment of vitiligo. Bergapten, or 5-methoxypsoralen, is available in Europe and is now undergoing trials in the United States to confirm its efficacy in psoriasis. Psoralen is used in some Mediterranean countries for the treatment of psoriasis and vitiligo.
Biological effects of bergamot and its potential therapeutic use as an anti-inflammatory, antioxidant, and anticancer agent
Published in Pharmaceutical Biology, 2023
Sabrina Adorisio, Isabella Muscari, Alessandra Fierabracci, Trinh Thi Thuy, Maria Cristina Marchetti, Emira Ayroldi, Domenico Vittorio Delfino
Other recent studies have evaluated the anti-inflammatory activity of a new phytochemical formulation called bergapten (Sicari 2018), a furanocoumarin derived from various Citrus species (including bergamot) through a complex separation process requiring optimized CO2 and temperature conditions. In in vitro studies, this phytocomplex decreased the expression and release of pro-inflammatory cytokines, such as TNF-α and interleukins, reduced prostaglandin levels, promote the clearance of neutrophils and macrophages from sites of inflammation, and reduced oxidative stress through the inhibition of ROS (Zhou et al. 2017). In addition, the anti-inflammatory properties of bergapten were further confirmed in a rat acetic acid-colitis model. Following treatment with bergapten, rats with colitis showed a normal colon-weight-length ratio, reduced colon damage, and reduced degranulation of mast cells, which are involved in the inflammatory process, in the mucosa (Adakudugu et al. 2020). Similarly, another bergamot derivative, a heteropolysaccharide termed CMSPB80-1 that was isolated and purified from Citrus medica var. sarcodactylis by alkaline extraction and characterized by mass spectrometry, shows strong antioxidant activity. This compound enhances the phagocytosis of macrophages and significantly promotes NO production and proliferation of mouse splenocytes, suggesting potential as an immunomodulatory agent (Peng et al. 2019).
Bergamot oil as an integral component of nanostructured lipid carriers and a photosensitizer for photodynamic treatment of vitiligo: Characterization and clinical experimentation
Published in Expert Opinion on Drug Delivery, 2021
Mai Shaaban, Maha Nasr, Abeer A. Tawfik, Maha Fadel, Omaima Sammour
The use of plants rich in psoralens (natural photosensitizers) was employed many centuries ago in ancient India and Egypt for the treatment of leukoderma and vitiligo [23]. One of the most important plant products that have been frequently used is bergamot oil (BO), which is the oil of citrus bergamia belonging to family Rutaceae [24], and is mainly composed of volatile ingredients as limonene, linalool, linalyl acetate, and nonvolatile compounds as bergamottin, bergapten, and citropten. BO was reported to induce phototoxic reactions with persistent pigmentation following application to the skin, and subsequent irradiation using ultraviolet light either UVA or UVB light [25–27]. This can be particularly advantageous for the treatment of dermatological diseases such as vitiligo, which is an acquired idiopathic skin pigmentation disease resulting from the loss of melanocytes from the basal layer of the epidermis [28]. Among the phototherapy protocols used for the management of vitiligo is the narrowband ultraviolet B (NB-UVB) light (with a peak at 311 nm) [29]. However, the NB-UVB light was reported to be more effective when combined with psoralens (P-NBUVB) owing to the direct melanin-inducing effect of 311 nm radiation, in addition to the psoralen-induced photochemical effects [29–31].
Relationship between Furocoumarin Intake and Melanoma History among US Adults in the National Health and Nutrition Examination Survey 2003-2012
Published in Nutrition and Cancer, 2020
Melissa M. Melough, Kijoon Kim, Eunyoung Cho, Ock K. Chun
Average furocoumarin consumption among all US adults was about 81 μg/day. Few other studies have attempted to estimate total furocoumarin intake, and these estimates have varied widely and changed over time (1). In 1991, Wagstaff estimated that individuals in the US consuming furocoumarin-containing foods consumed an average of 1300 μg of furocoumarins per day (27), approximately 16 times more than estimated in this study. Importantly, Wagstaff’s study was limited to scarce analytical information regarding the furocoumarin contents of foods. For example, in Wagstaff’s estimation, the only furocoumarin attributed to grapefruit was bergapten at a concentration of 120 μg/g based on a single report from 1975 (33). In contrast, more recent studies have found only trace amounts of bergapten in grapefruit (11, 12, 26, 29) and have suggested that 6′7′-DHB and bergamottin are the two major furocoumarins in grapefruit (11, 12, 29, 32, 34). Furthermore, Wagstaff assumed a high concentration of furocoumarins in lemon- or lime-flavored carbonated beverages and therefore estimated that limes contributed approximately 97% of total furocoumarin intake.