Determination of furocoumarins in essential oils

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1 Japan Journal of Aromatherapy Vol. 17, No. 1, * Determination of furocoumarins in essential oils Abstract In this study, phototoxic furocoumarins were detected in various essential oils to provide aromatherapy-related safety information. p-chlolorobenzophenone was employed as an internal standard in a selected ion monitoring mode for the detection of phototoxic compounds using gas chromatography-mass spectrometry GC-MS. To ensure the precise detection and determination of certain phototoxic compounds, including psoralen, xanthotoxin, bergapten, and isopimpinellin, as well as a non-phototoxic coumarin, aurapten, in the same GC-MS analysis, nine mass ions were selected. Among a total of 116 kinds of commercially available essential oil products, furocoumarins were detected in four Apiaceae and nine Rutaceae oils. Aurapten, on the other hand, was detected in six Rutaceae oils. Key words: essential oil, furocoumarin, phototoxicity, bergapten, GC-MS 1. 1, 2 1, 3 HIV A UVA, nm C 19 H 22 O ppm IFRA International Fragrance Association Masayoshi SAWAMURA* 1, Satoru SUZUKI 2, Noriko OHARA 2, Miyu SATO 2, Motifumi TOUTANI 2 1. FBC/Tosa Food Business Creator Project Team, Kochi University 2. /Umajimura Agricultural Cooperative

2 40 Vol. 17, No. 1, p- CBP 8-5- LKT Laboratories 1 20 mg/l 2.3 GC-MS 1.5 ml 0.1 ml 20.1 mg/l CBP 0.9 ml GC-MS mg/kg 19 GC-MS 2.4 GC-MS 19 GC-MS SIM selected ion monitoring GC-MS GC- MS QP-2010Plus AOC-20i DB-1 15 m 0.25 mm ID 0.2 µm J & W Scientific, USA /min /min min : 1 1 µl SIM TIC 3 mg/kg GC-MS SIM TIC 10

3 Japan Journal of Aromatherapy Vol. 17, No. 1, No. 1 Pimpinella anisum 2 Angelica archangelica 3 Inula graveolens 4 Helichrysum italicum 5 Iris pallida 6 Cananga odorata 7 Canarium luzonicum 8 Pimenta officinalis 9 Citrus sinensis 10 Citrus sinensis 11 Abs. Dianthus caryophyllus 12 Citrus sphaerocarpa 13 Matricaria chamomilla 14 Anthemis nobilis 15 Torreya nucifera 16 Melaleuca leucadendron 17 Elettaria cardamomum 18 Ferula galbaniflua 19 Daucus carota 20 Abs. Osmanthus fragrans 21 Cinnamomum camphora 22 Cuminum cyminum 23 Salvia sclarea 24 Citrus paradisi 25 Eugenia caryophyllata 26 Lindera umbellata 27 Alpinia specia 28 Sciadopitys verticillata 29 Copaifera officinalis 30 Coriandrum sativum 31 Cupressus sempervirens 32 Santalum album 33 Cistus ladaniferus 34 Perilla frutescens 35 Cedrus atlantica 36 Cymbopogon nardus 37 Cinnamomum zeylanicum 38 Abs. Jasminum sambac 39 Juniperus communis 40 Zingiber officinale 41 Cryptomeria japonica 42 Cryptomeria japonica 43 Illicium verum 44 Mentha spicata 45 Salvia officinalis 46 Pelargonium graveolens 47 Apium graveolens 48 Hypericum perforatum 49 Thymus vulgaris 50 Artemisia dracunculus 51 Citrus reticulata Blanco var. tangerine 52 Abs. Polianthes tuberosa 53 Melaleuca alternifolia 54 Malaleuca ericifolia 55 Leptospermum petersonii 56 Anethum graveolens 57 Myristica fragrans 58 Melaleuca quinquenervia 59 Melaleuca quinquenervia 60 Citrus aurantium 61 Abs. Viola odorata 62 Pinus sylvestris 63 Ocimum basilicum 64 Pogostemon cablin 65 Mentha arvensis 66 Abs. 10 Vanilla planifolia 67 Cymbopogon martini 68 Valeriana officinalis 69 Hyssopus officinalis 70 Chamaecyparis obtusa 71 Thujopsis dolabrata 72 Abs. Xanthorrhoea preissii 73 Foeniculum vulgare 74 Citrus aurantium 75 Piper nigrum

4 42 Vol. 17, No. 1, No. 76 Boswellia carterii 77 Abs. Plumeria alba 78 Callitris intratropica 79 Abs. Spartium junceum 80 Laurus nobilis 81 Vetiveria zizanioides 82 Mentha piperita 83 Citrus bergamia 84 Citrus bergamia Styrax tonkinensis 86 Cinnamomum camphora var. glaucescens 87 Origanum majorana 88 Myrtus communis 89 Leptospermum scoparium 90 Citrus reticulata 91 Abs 25 Acacia decurrens 92 Commiphora myrrha 93 Melissa officinalis 94 Abies sachalinensis 95 Abies sibirica 96 Achillea millefolium 97 Eucalyptus globulus 98 Citrus junos 99 Citrus junos 100 Citrus aurantifolia 101 Lavandula hybrida 102 Lavandula officinalis 103 Ravensara aromatica 104 Litsea cubeba 105 Citrus limon 106 Citrus limon 107 Cymbopogon flexuosus 108 Lippia citriodora 109 Backhousia citriodora 110 Rosa damascena 111 Abs. Rosa damascena 112 Aniba rosaeodora 113 Rosmarinus officinalis 114 Rosmarinus officinalis 115 Abs. Nelumbo nucifera 116 Levisticum officinalis 2. MS m/z p-cbp vw w w vw vw vw vw w w w vw w: weak, vw: very weak TIC SIM m/z GC-MS 100 SIM 1

5 Japan Journal of Aromatherapy Vol. 17, No. 1, m/z m/z m/z 185.9, CBP m/z 105.0, m/z 215.9, m/z 215.9, m/z 230.8, m/z 69.1, No α- δ-3- C 15 H 16 O mg/kg 61.2 mg/kg No β- 8.7, 1.8 mg/kg 10.5 mg/kg No. 73 No. 1 3 mg/kg No. Pso SD Xth SD Ber SD Ipp SD Aur SD * nd 12 nd nd nd nd nd nd 51 nd nd nd nd 60 nd nd nd nd 73 nd nd nd nd 74 nd nd nd nd nd nd nd nd nd nd 98 nd nd nd nd nd nd nd nd 100 nd nd nd 105 nd nd nd nd nd nd nd 116 nd nd nd nd Pso Xth Ber Ipp Aur nd * 3 SD)

6 44 Vol. 17, No. 1, 2016 No mg/kg No mg/kg No. 12 γ , 14.0 mg/kg 8,460 mg/kg No , mg/kg 7.0 mg/kg 0.9 mg/kg 78.1 mg/kg 5,470 mg/kg No Citrus reticulata mg/kg 13 No. 90 No. 60 R mg/kg mg/kg No mg/kg Citrus aurantium 13 No. 83, No mg/kg 1.4 mg/kg 1.1 mg/kg No mg/kg No. 98, /2 Yuzu

7 Japan Journal of Aromatherapy Vol. 17, No. 1, γ No mg/kg 10,300 mg/kg 116 No. 99 No. 100 γ- β , 4.9 mg/kg Peroutka et al , 4.5 mg/kg 4 No. 105, , 34 β- 25 No mg/kg 1.5 mg/kg 3.5 mg/kg No. 106 Naganuma et al mg/kg mg/kg , C 21 H 22 O 4 7 Messer et al. 37 P450 CYP3A ,000 mg/kg 7, mg/kg 1/260 IFRA GC-MS ,013 hpa Ruta graveolens 39

8 46 Vol. 17, No. 1, , No. 1 No. 18 No. 19 No. 22 No. 30 No No. 9 No. 10 No. 74 No. 90 No. 99 No Borges F., Roleira F., Milhazes N., Santana L., Uriarte E.: Simple coumarins and analogues in medicinal chemistry: Occurrence, synthesis and biological activity, Current Med. Chem., 12, Bubols G. B., da Rocha Vianna D., Medina-Remón A., von Poser G., Lamuela-Raventos R. M., Eifler-Lima V. L., Garcia S. C.: The antioxidant activity of coumarins and flavonoids, Mini-Reviews in Med. Chem., 13, Thakur A., Singla R., Jaitak V.: Coumarins as anticancer agents: A review on synthetic strategies, mechanism of action and SAR studies, Europ. J. Med. Chem., 101, Spino C., Dodler M., Sotheeswaran S.: Anti-HIV coumarins from calophyllum seed oil, Bioorg. Med. Chem. Letters, 8, Anand P., Singh B., Singh N.: A review on coumarins as acetylcholinesterase inhibitors for Alzheimer s disease, Bioorg. Med. Chem., 20, Caporale G., Musajo L., Rodighiero G., Baccichetti F.: Skin-photosensitizing activity of some methylpsoralens, Experientia, 23, pp , Zaynoun S. T., Johunson B. E., Frain-Bell W.: A study of bergamot and its importance as a phototoxic agent. II. Factors which affect the phototoxic reaction induced by bergamot oil and psoralen derivatives, Contact Dermatitis, 3, , Sheinfeld N., Deleo V.: A review of studies that have utilized different combinations of psoralenand ultraviolet B phototherapy and ultraviolet A phototherapy, Dermatol. Online J., 9, Kraemer C. K., Menegon D. B., Cestari T. F.: Determination of the minimal phototoxic dose and colorimetry in psoralen plus ultraviolet A radiation therapy, Photodermatol. Photoimmunol. Photomed., 21, Di Lemia V., Guareschi, E.: Successful treatment of hand and foot psoriasis with infliximab, Dermatol. Online J., 16, Nguyen Thi Lan Phi 9, Dugo P., Mondello L., Cogliandro E., Verzera A., Dugo G.: On the genuineness of citrus essential oils. 51. Oxygen heterocyclic compounds of bitter orange oil Citrus aurantium L., J. Agric. Food Chem., 44, Clark S. M., Wilkinson S. M.: Phototoxic contact dermatitis from 5-methoxypsoralen in aromatherapy oil, Contact Dermatitis, 38, Peroutka R., Schulzova V., Botek P., Hajslova J.: Analysis of furanocoumarins in vegetables Apiaceae and citrus fruits Rutaceae, J. Sci. Food Agric., 87, Belsito, E. L., Carbon C., Di Gioia M. L., Leggio A., Liguori, A., Perri F., Sicilaiano C., Viscomi M. C.: Comparison of the volatile constituents in cold-pressed bergamot oil and a volatile oil isolated by vacuum distillation, J. Agric. Food Chem., 55, pp , , Nivinskiene O., Butkiene R., Mockute D.: Changes in the chemical composition of essential oil of Angelica

9 Japan Journal of Aromatherapy Vol. 17, No. 1, archangelica L. roots during storage, Chemija Vilnius, T. 14, Zhang Z.-R., Leung W. N., Cheung H. Y., Chan C. W.: Osthole: A review on its bioactivities, pharmacological properties, and potential as alternative medicine, Evid.- Based Complement. Alternat. Med., 2015, Curtis S.: Essential Oils, Fennel; pp , Grapefruit; pp , Tangerine; pp , Bergamot; pp , Lemon and lime; pp , Aurum Press, London C L K P J B S Levisticum officinale W. D. J. Koch 8 Aroma Res., 2, Sawamura M.: Volatile components of essential oil of the Citrus genus, In Pandarai S. G. Ed., Recent Research Developments in Agricultural & Food Chemistry Vol. 4, pp , Research Signpost, Trivandrum, India , Aroma Res., 18, Niijima A., Nagai K.: Effect of olfactory stimulation with flavor of grapefruit oil and lemon oil on the activity of sympathetic branch in the white adipose tissue of the epididymis, Exp. Biol. Med., 228, p Aromatopia, 8, Aromatherapy Environment, 60, Citrus junos Aroma Res., 10, Nguyen Thi Lan Phi 9, Aroma Res., 10, p Naganuma M., Hirose S., Nakayama Y., Nakajima K., Someya T.: A study of the phototoxicity of lemon oil, Archiv. Dermatol. Res., 278, Aroma Res., 10, Messer A., Raquet N., Lohr C., Schrenk D.: Major furocoumarins in grapefruit juice II: Phototoxicity, photogenotoxicity, and inhibitory potency vs. cytochrome P450 3A4 activity, Food Chem. Toxicol., 50, Kakar S. M., Paine M. F., Stewart P. W., Watkins P. B.: 6,7 -Dihydroxybergamottin contributes to the grapefruit juice effect, Clinical Pharmacol. Therapeutics, 75, pp , Aroma Res., 7, Hirota R., Roger N. N., Nakamura H., Song H.-S., Sawamura M., Suganuma N.: Anti-inflammatory effects of limonene from yuzu Citrus junos Tanaka essential oil on eosinophils, J. Food Sci., 75, H87 H Aroma Res., 5, Aroma Res., 8, Aroma Res., 4, GC-MS p- SIM GC-MS FBC TEL: FAX: sawamuram@kochi-u.ac.jp

LESSON 1. Studies monoterpene rich essential oils. Dive in and find out all the amazing benefits of these essential oils.

LESSON 1. Studies monoterpene rich essential oils. Dive in and find out all the amazing benefits of these essential oils. LESSON 1 Studies monoterpene rich essential oils. Dive in and find out all the amazing benefits of these essential oils. 1. Blank Inhalers Multicolor 8 count 2. Glass Bottle w/orifice Reducer Cap Green