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The Presently Known Distribution of Furocoumarins (Psoralens) in Plants* M

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The Presently Known Distribution of Furocoumarins (Psoralens) in Plants* M THE PRESENTLY KNOWN DISTRIBUTION OF FUROCOUMARINS (PSORALENS) IN PLANTS* M. A. PATHAK, Pn.D.**, FARRINGTON DANIELS, JR., M.D.*** AND T. B. FITZPATRICK, M.D.** The recent use of psoralen compounds (1) in(including psoralen and imperatorin) were the the treatment of vitiligo and as a means ofmost effective antifungal agents among seventeen natural coumarin derivatives tested. Some hither- increasing the tolerance of human skin to solarto unreported results of Dolcher, Rodighiero and radiation and increasing the pigmentationCaporale have been mentioned by Musajo (8): which follows exposure to ultraviolet radiationthey described the mutagenic properties of five illustrates how ancient medical lore may some-furocoumarins and found 5-methoxypsoralen and times be modified to satisfy present-day demands.psoralen to be almost as effective mutagenic agents as is light-sensitized trypafiavin. Altenburg The furocoumarins, more commonly known as(9) reports that psoralens increase the mutation psoralens, are pharmacologic agents which, withrate in drosophila. modern technics, can be isolated from herbal During the last three decades an increasing number of reports have been published about a remedies that have been employed for manyform of dermatitis in man which follows contact centuries (2). Concomitantly with recent prog-with many plants and subsequent exposure of the ress in the synthesis of new organic moleculesskin to sunlight (10, 11, 12, 13). It has long been for therapeutic purposes, interest in manyknown that photosensitization dermatitis with ancient drugs and herbal concoctions has beenresidual pigmentation develops in skin which has come into contact with figs, cow parsnip, wild revived because some of these medicaments haveparsnip, wild carrot, fennel, caraway, anise, been found to contain specific pharmacologicalcoriander, angelica, parsley and several other agents which exert scientifically recognizableplants. The condition has also been described in therapeutic effects. individuals exposed to the oil of Persian limes (14) and among carrot processers (13, 15). Recently Furocoumarins (psoralen, 8-methoxypsoralenthe phytophotodermatitis due to furocoumarins (xanthotoxin) and 5-methoxypsoralen (bergap-has become a public health problem among celery ten)) occur naturally in the leaves, roots and fruitpickers (16). This phytophotodermatitis, as well of plants which have been used for centuries inas that which follows contact with plants of other India, Egypt and other oriental countries (2) forspecies, is thought to be caused largely by furo- the treatment of vitiligo. Fowiks et at. (3) havecoumarin compounds which are characteristically reported that furocoumarins exert a photosensi-present in these plants. The occurrence of furo- tizing effect on bacteria in the presence of long-coumarins in many familiar edible plants, and the wave ultraviolet light. In a later publication,widely recognized photosensitizing action of these Fowiks (4) has also pointed out that these com-compounds have recently led the authors (17) to pounds belong to a group of substances whichstudy the mechanisms of photosensitivity and can inhibit certain aspects of plant growth with-photodynamic action in detail. Whether the skin out otherwise harming the plant; he has furthercan be photosensitized by ingestion of natural postulated that furocoumarins may act as naturalfurocoumarin containing foods has not yet been growth regulators in certain plants (5, 6). Chakra-established. borty et al. (7) have shown that the psoralens Several clinical manifestations of phytophoto- dermatitis have specific names: e.g., "berloque *Fromthe Research Laboratories of thedermatitis" which is the reaction to 5-methoxy- Department of Dermatology of the Harvardpsoralen present in the oil of Bergamot used in Medical School at the Massachusetts Generalcertain perfumes (10, 18, 19, 20); and "dermatitis Hospital, Boston 14, Massachusetts and the De-bullosa striata pratensis" (21, 22, 23, 24) which partment of Dermatology of the University offollows exposure of the skin to sunlight after it Oregon Medical School, Portland, Oregon. has come into contact with "meadow grass" (in **Presentaddress; Dept. of Dermatology Mass. most cases Agrimony eupatoria). General Hospital, Boston 14, Mass. Several publications dealing with dermatitis 5*5Presentaddress: Division of Dermatology Cornell University Medical School, New York,caused by plants and eau de cologne have ap- N.Y. peared in European and American dermatologic This work was supported by Grant CY-2837journals. A large number of these deal with the (C-2 and C-3) P. E. T., and Grant #CY-5003 (C-i)erythemal response and hyperpigmentation asso- from the National Institutes of Health, Unitedciated with sea bathing and outdoor sun bathing States Public Health Service. on clear sunny days after the application of eau Received for publication November 24, 1961. de cologne. It is known that several perfumes 225 TABLE 1 Distribution of Furocoumarins in Nature No. Compound and Structure Natural Sourres Common Name Family References Psoralen Psoralea corylifolia Babachi Leguminosae 27, 28, 29 (Ficusin) Ficus carica Fig Moraceae 28, 30, 31 0 Coronilla glauca Leguminosae 8, 32 Phebalium argenteum 33, 34 ' ' 1 2 Xanthoxylum flavum West Indian satin Rutaceae 35 WOO d a 2. 5-Methoxypsoralen Ficus carica Fig Moraceae 8, 28, 30, 36, 37, (Bergapten, Majudin, ileraclin) 38, 39 Z Fagara xanthoxyloides Artar prickly ash Rutaceae 28, 37, 40 0 Skimmialaureola Neera Rutaceae 8, 28, 37, 41 ,.7 Citrus bergamia (Risso) Bergemot oil Rutaceae 8, 28, 37, 42 J j Ruta graveolens Rue Rutaceae 8, 38, 39, 43, 44, 45 Citrus limonum Lemon Rutaceae 38 0C112 Citrus acida Lime Rutaceae 37, 46 Fagara schinofolia Rutaceac 47 Ligusticum acutifolium ljmbelliferae 8, 28, 37 acutilobum Umbelliferae 48 Ligusticum N Heracleum sphondylium Cow parsley Umbelliferae 8, 28, 37, 39, European cow parsnip N Heracleum giganteum IJmbelliferae 8, 37, 39 Ammi majus Linn Bishop's weed I.Jmbelliferae 50 Heracleum nepalense Ilmbelliferae 8, 39 Seseli indicum Hoegen celery IJmbelliferae 8, 26, 37, 39 Pastinaca sativa Garden parsnip IJmbelliferae 8, 30, 51 Heracleum lanatum Cow parsnip Umbelliferae 52 Angelica archangelica Angelica, Engel- Umbelliferae 53, 54 wurz Ammi majus Bishop's weed Umbelliferae 39, 50 Pimpinella magna Umbelliferae 8, 39 Pimpinella saxifraga Cow parsnip lJmbelliferae 8, 28, 37, 39, 55, 56 Petroselium sativum Garden parsley Umbelliferae 8, 39, 57 3. 8-Methoxypsoralen Ammi majus Bishop's weed IJmbelliferae 50, 58, 59, 60, 61 (Xanthotoxin or Methoxalen or Ammoidin) Angelica archangelica Engelwurz lJmbelliferae 52 Pastinaca sativa Garden parsnip IJmbelliferae 51 00H3 Ficus carica Fig Moraeeae 38 0 Ruta chalepensis Rutaceae 8, 28, 37, 39, 41 Fagara xanthoxyloides Rutaceae 28, 29, 40, 62 70(IV0/ Ruta montana Rutaceae 8, 39, 63 Aegle marmelos Bel Rutaceae 64 Ruta graveolens Rue Rutaceae 8, 38, 39, 44 Luvanga scandens Lavanga Rutaceae 65 Xanthoxylum flavum West Indian satin Rutaceae 35 '-3 wood Ruta bracteosa Rutaceae 41 4. 8-Isopentenyloxypsoralen Imperatoria ostruthium Masterwort IJmbelliferae 28, 37, 66 (Imperatorin or Ammidin) Hog fennel z Umbelliferae 28, 37, 64 Angelica glabra C Angelica archangelica Engelwurz IJmbelliferae 28, 37, 67 OH3 Ammi majus Umbelliferae 59, 60, 61 / Peucedanum ostruthium Masterwort Ijmbelliferae 28, 29 OCH2—CH=C Pastinaca sativa Parsnip IJmbelliferae 37 C \ Prangos pabularia Umbelliferae 37, 76 C OH3 Aegle marmelos Bel Rutaceae 37, 68, 69 Ruta chalepensis Rutaceae 53 /O\1/O\\/V 5. 5,8-Dimethoxypsoralen Pimpinella saxifraga Oow parsnip Umbelliferae 28, 37, 70, 71 (Isopimpinellin) Heracleum sphondylium Oow parsley IJmbelliferae 28, 37, 72 Sesli indicum Hog celery lJmbelliferae 28, 37 00H3 Skimmialaureola Neera Rutaceae 41 Oitrus aurantifolia West Indian lime Rutaceae 37, 73 oil Luvanga scandens Rutaceae 65 I_11//V Thamnosma montana Rutaceae 5 Fagara oilanthoides Rutaceae 74 00H3 Heracleumlanatum (var. Rutaceae 52 nipponicum) Oitrus acida Lime Rutaceae 46 -4 TABLE 1—Continued No. Compound and Structure Natural Sources Common Name Family References 6. 5-Isopentenyloxypsoralen Peucedanum ostruthium Masterwort Umbelliferae 28, 29, 37 (Isoimperatorin) Imperatoria ostruthium Masterwort TJmbelliferae 28 Pastinaca sativa Garden Umbelliferae 75 /"\ /\/0 parsnip CH LHL)OCH2—CH=C CH3 7. Prangenine Prangos pabularia Tlmbelliferae 76 / 0 0 /°N/I z I U) 0CH2(CH2)2CH3 8. 4'-Methoxy,-S'-isopropylpsoralen Peucedanum offleinale Masterwort lJmbelliferae 28, 77 s. (Peucedanin) Prangos pabularia IJmbelliferae 37 H3C H / C 0 H3C \/U\/\I 9. 5-Epoxy isopentenyloxypsoralen Peucedanum offleinale Masterwort TJmbelliferae 28, 29, 37 (Oxypeucedanin) Peucedanum ostruthium Masterwort Umbelliferae 37 Prangos pabularia lJmbelliferae 37 / 0 \/0 Imperatoria ostruthium Masterwort lJmbelliferae 8 Ii /I OCH2—CH—C—(CH3)2 0 10. Oreoselone Peucedanumofficinale Masterwort TJmbelliferae 29 Peucedanumoreoselinum 78 H30 ' /0 113 11. Ostruthol' Peucedanum ostruthium Masterwort Umbelliferae 28, 29, 37, 79 (ii/\ /N/0 OCH2CH—C(C113)2 ()H OCOC===CH CU3 CH3 12. 5-Methoxy,8-isopentenyloxypsoralen Angelica glabra Umbelliferae 29 (Phellaptorin) Phellopterus littoralis Umbelliferae 29 CU3 OCH2CH=C" -4 /0\/0\/OCH3 Z 13. 4',5-dihydro,5'(-1-glucosoxy-isopropyl)psoralen Peucedanum decursivum Umbelliferae 37, 80 (Nodakenin) H3C 0C6H1105 / 0 H3C/ NJ 112 TABLE 1—Continued No. Compound and Structure Natural Sources Common Name Family References 14. Aglucone of nodakenin Peucedanum decursivum Marmesin Umbelliferae
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