Bergaptene

Oil of bergamot contains about 5 per cent, of an odourless solid body known as bergaptene. This body has the formula Cj HgO, and melts at... 

Xanthotoxin, Cj HgO, is isomeric with bergaptene, and is present in the oil of Fagara xanthoxyloides. It is a solid compound, melting at 145° to 146°, and is a pyrogallol derivative, having the constitution—... 

CYP6D1 of the housefly (Musca domestica) has been found to hydroxylate cyper-methrin and thereby provide a resistance mechanism to this compound and other pyrethroids in this species (Scott et al. 1998 see also Chapter 12). Also, this insect P450 can metabolize plant toxins such as the linear furanocoumarins xanthotoxin and bergapten (Ma et al. 1994). This metabolic capability has been found in the lepi-dopteran Papilio polyxenes (black swallowtail), a species that feeds almost exclusively on plants containing furanocoumarins. 

Figure 11.1a [1] shows a schematic representation of a micropreparative thin-layer chromatogram obtained on a 0.5-mm Florisil (magnesium silicate) layer prewetted with benzene of a crude extract, i.e., containing coextracted plant oil obtained from Heracleum moelendorfi fruit. The initial band of extract was washed with benzene and then separated by continuous development with ethyl acetate in benzene [1]. As seen from the fraction analysis presented in Figure 11.1b, small quantities of pure bergapten and xanthotoxin can be isolated in this maimer. 

FIGURE 11.1 (a) Schematic representation of PLC of Heracleum moellendorfi fruit, crude extract (500-pl 2% solution), system Florisil/AcOEt + B plate preeluted with benzene (b) analytical HPLC of isolated fractions, system ClS/MeOH + HjO (6 4). Abbreviations B — bergaptene, I — imperatorin, Ph — phelopterin, X — xanthotoxin. (For details, see Waksmundzka-FIajnos, M. and Wawrzynowicz, T., 7. Planar Chromatogr., 5, 169-174, 1992.)... 

Bergapten Stems, leaves, cell cultures Arborinine ... 

A new class of secondary metabolites tyrolobibenzyls A 36 and B 37 were isolated from Scorzonera humilis (Asteraceae) of Tyrolean origin. Compounds 36 and 37 were shown to possess a unique phenylethylbenzofuran skeleton <00HCA292O>. The structure of the dimeric coumarin 38 was confirmed by an X-ray diffraction study, as well as by a photochemical synthesis from its co-occurring monomer bergapten <00H(53)441>. 

Genotoxicity of bergapten and bergamot oil in Saccharomyces cerevisiae. Journal of Photochemistry and Photobiology. B, Biology, 7, 209-229. 

Furocoumarins such as isopimpinellin, bergapten, and kokusagin have antifeedant activity against Spodoptera litura (54). A number of similar compounds from umbelliferous plants have been demonstrated to be active antifeedants against Spodoptera litura. Periplaneta americana. Musca domestica. Blattela germani ca, and Stylopyga rhombifolia (98). 

Coumarin 162 (Structure 4.49) is a naturally occurring lactone in crystal form found in hay and tonka beans. It is one of the most used fragrance materials and is responsible for spicy green notes. Dihydrocoumarine 163 is also present in various essential oils with a characteristic sweet herbal odour. Umbellif-erone 164, scopoletin 165, bergaptene 166 and coumarin are found in Rutaceae, Apiaceae, Lamiaceae and Asteraceae oils. Nepetalactones 167 are confined to the oils of Nepeta species [1,3, 21-23, 63]. 

Anethum graveoleus L. Shi Luo (Dill) (fruit, young shoot) Essential oils, d-carvone, dillapiole, limonene, bergapten, umbelliprenin, camphene, dihydrocarvone, dillapiole, dipentene, isomyristicin 48-50 Carminative, stimulant. 

Dictamnus albus L. subsp. dasycarpus (Turcz.) Winter D. dasycarpus Turcz. Bai Xian Pi (Fraxinella) (root bark) Dictamnine, skimmianine, saponins, preskinnianine, choline, fragarine, aurapten, bergapten, isomaculosindine, limonin, obakinone, fraxinellone, psoralen, trigonelline.50 60 Antifungal, antipyretic, antiseptic, antitussive, sedative, emmenagogue, tonic. 

Poncirus trifoliata Rafin Gou Gi (Trifoliate orange) (fruit) Poncirin, limonin, imperatorin, bergapten, neohesperidin, citrifoliol, myrcene, camphene, gamma-terpinene.33 Treat gastric pain, constipation, and prolapse of the uterus or rectum. 

Zanthoxylum schinifolium Sieb. et Zucc. Hua Jiao (Pepper) (pericarp) Estragol, citronellol, phellandrene, xanthoxylene, skimmianine, magnoflorine, xanthoplanine, dictamnine, bergapten, berberine, esculetin dimethyl ether.33 48-53 Treat ascaris, relieve abdominal pain caused by ascariar obstruction. 

N.A. Limonene, coumarins, apiin, oleic, linoleic, palmitic, paliloleic, petroselinic, petroselaidic, stearic, myristic, and myristoleic acids, bergapten.99-102 110 It is carminative and antirheumatic. 

Angelica amurensis Schischk. A. anomala Lallem. A. dahurica (Fisch.) Benth. et Hook. Byak-angelicin, byak-angelicol, oxypeucedanine, imperatorin, phellopterin, xanthotoxine, marmesin, scopoletin, marmesin, scopoletin, anomalin, angenomalin, bergapten.33 Antipyretic, treat toothache, headache. Externally for mastitis and wound infection. 

Umbelliferone (7-hydroxycoumarin) readily dimerizes in sunlight,236 and certain naturally occurring furocoumarins have been photochemically dimerized in the laboratory. These include psoralen (249), bergapten (5-methoxy psoralen), angelicin237 (250), and peucedanin.238 The corresponding dimer of xanthotoxin (8-methoxy-psoralen) could not be obtained under identical conditions, but on... 

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