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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
A class of substances often brought into connection with phototoxicity of EOs are the furocoumarins. They are synthesized and used by plants as defensive chemicals and are characterized by their coumarin structure conjoined with a furan ring. Depending on their position, they can be differentiated into two subtypes: the linear psoralen type and the angular angelicin type (see Figure 28.16). Furocoumarins like psoralen, bergapten (= 5-MOP), xanthotoxin, and angelicin, which are abundant in the Apiaceae, Rutaceae (e.g., some Citrus species), Moraceae. and other families, are known to be phototoxic and also carcinogenic under UV irradiation (Fu et al., 2013). Others, like bergamottin, bergaptol, isobergapten, and isopimpinellin are non-phototoxic. Furocoumarins are larger than most EO constituents, but can pass over during steam-distillation anyway. Still, cold-pressed EOs show much higher content of these compounds than steam-distilled ones. Commonly available EOs that are known to be phototoxic include the EOs of angelica root, bergamot (cold pressed), bitter orange (cold pressed), cumin, fig leaf absolut, grapefruit (cold pressed), lemon (cold pressed), lime (cold pressed), mandarin leaf, opopanax, rue, and tagetes. The following might be phototoxic: clementine (cold pressed), combava fruit, skimmia, angelica root, celery leaf and seed, cumin seed, khella, lovage leaf, and parsnip (Tisserand and Young, 2014).
Identifying Pharmaceutical-Grade Essential Oils and Using Them Safely and Effectively in Integrative Medicine
Published in Aruna Bakhru, Nutrition and Integrative Medicine, 2018
A limited number of essential oils may cause chemically induced skin irritation when minor compounds present absorb energy from long-wave ultraviolet (UV-A 320–380 nm) radiation. When these compounds are present in the epidermis or dermis and exposed to UVA, activated derivatives are formed that induce cellular damage. The reaction typically begins approximately 24 hours after exposure and peaks at 48–72 hours.88 Phytophotodermatitis reactions resemble an exaggerated sunburn, but have the potential to induce postinflammatory hyperpigmentation lasting weeks to months. Phytophotodermatitis can be avoided by preventing sun exposure for at least 12 hours following the application of photosensitive oils—angelica, bay laurel absolute, bergamot, bitter orange, cumin, grapefruit, khella, Mediterranean mandarin, neroli, lemon (expressed), lime (expressed), petitgrain, rue, and tagetes. These oils contain compounds known to induce phytophotodermatitis based on their concentration of phototoxic furanocoumarin compound(s), such as angelicin, bergamottin, bergapten, citropten, imperatrotin, isobergapten, isoimperatorin, methyoxsalen, and oxypeucedanin, and the duration of UVA exposure.89–91
Catalog of Herbs
Published in James A. Duke, Handbook of Medicinal Herbs, 2018
Roots and fruits contain several furocoumarins, e.g., angelicin, bergapten and xanthotoxin, as well as umbelliprenin and various phenols. The main constituent of the root essential oil is beta-phellandrene; others include alpha-pinene, borneol, osthenole, osthole, angelicin, methyl ethyl acetic acid, diacetyl, methanol, ethanol, and furfural. The most important aroma compound is a lactone of 15-hydroxypentadecanoic acid. The flavonoid archange-lenone has recently been identified Escher et al. identified five previously unknown phellandrene derivatives with a typical angelica smell from the root oil: 2-nitro-l,5-P-menthadiene, cis and trans 6-nitro-1(7), 2P menthadiene; trans-1(7)-5P menthadiene-2-yl-acetate, and 7-isopropyl-5-methyl-5-bicyclo(2.2.2.) octan-2-on.86 The seed oil is said to contain 0.5% imperatorin, 0.1% bergaptene, 0.02% xanthotoxol, 0.04% umbelliprenin and a phenol. Phellandrene, methyl ethyl acetic acid, and hydroxymynstic acid are also reported.
The state of the art of fetal hemoglobin-inducing agents
Published in Expert Opinion on Drug Discovery, 2022
Aline Renata Pavan, Juliana Romano Lopes, Jean Leandro Dos Santos
Phenotypic screening for small libraries using BFU-E cells found zileuton and the natural product angelicin to be interesting prototypes. Zileuton (75 µM) increased the HbF levels by 4.6-fold, while angelicin (200 µM) induced about an eight-fold increase in the percentage of F-cells (Table SI, Supplementary Material) [22].