5-Methoxypsoralen, an ingredient in several suntan preparations, has lethal, mutagenic and clastogenic properties

Ashwood-Smith, M.J.; Poulton, G. A.; Barker, Molly F.; Mildenberger, M.

doi:10.1038/285407a0

Cited by 176 publications

(53 citation statements)

References 36 publications

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“…The significant inhibitory effect of extract obtained from Taiwan-jashoshi on melanin production at the concentration of 25 mg/ml may be attributable to its major constituent, columbianadin (15). Similarly, the significant inhibitory effect of the extract from Hakuryo-dokkatsu on both melanin production and cell proliferation at the concentration of 25 mg/ml may be attributable to its major constituent, heraclenin (8).…”

Section: Discussionmentioning

confidence: 92%

“…The results concerning the melanogenesis activities of sixteen coumarins (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16) are shown in Fig. 3.…”

Section: Discussionmentioning

confidence: 99%

“…Since, their activities were not desirable for our purpose, further studies were suspended. The decreased stimulatory effect on melanogenesis of the extracts from To-dokkatsu at the concentration of 25 mg/ml may be attributable to its major constituents, osthol (14) and columbianadin (15).…”

Section: Discussionmentioning

confidence: 99%

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Melanogenesis Stimulation in Murine B16 Melanoma Cells by Umberiferae Plant Extracts and Their Coumarin Constituents

Matsuda

Hirata

Kawaguchi

et al. 2005

Biological & Pharmaceutical Bulletin

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Gray hair is caused by a genetic predisposition, aging, decrement of melanocytes by environmental stress, and decrement of the biosynthesis of melanin pigment or melanogenesis.1,2) Hair dye agents are used for the treatment of gray hair. However, there remain some problems with these agents, such as side effects due to the dyes. Thus, there is a need for anti-gray hair agents that exhibit satisfactory melanogenesis activity and gray hair prevention. For the development of gray hair prevention agents, we have carried out a screening program to find a potential stimulant of melanogenesis from natural resources by using cultured murine B16 melanoma cells with theophylline as a reference drug. In a preceding paper, 3) we reported that a methanolic extract from the leaves of Piper nigrum L. showed a significant stimulatory effect on melanogenesis in cultured murine B16 melanoma cells and that two lignans, (Ϫ)-cubebin and (Ϫ)-3,4-dimethoxy-3,4-desmethylenedioxycubebin, were isolated as its active constituents. As the next step in our herbal screening, we report here the melanogenesis stimulation effect of seven ethanolic extracts obtained from Umbelliferae -dokkatsu), and the fruits of Cinidium monnieri (L.) CUSSON (Jashoshi) and C. formosanum YABE (Taiwan-jashoshi). The melanogenesis stimulation effects of sixteen coumarins (1-16, Fig. 1) isolated from the Umberiferae crude drugs were also evaluated. MATERIALS AND METHODS MaterialsThe roots of Angelica biserrata (Todokkatsu), Notopterygium incisum (Kyokatsu), the fruits of Cinidium monnieri (Jashoshi) and Cinidium formosanum (Taiwan-jashoshi) were obtained from Osaka market. The roots of Angelica dahurica (Byakushi) and Heracleum candicans (Hakuryo-dokkatsu) were obtained from Chinese market (Yunnan Province). The roots of Heracleum lanatum (Gyubi-dokkatsu) were grown at the Osaka University of Pharmaceutical Sciences.Preparation of Ethanolic Extracts Seven crude drugs (each 10 g) were extracted with EtOH (100 ml) in a water bath at 70°C for 2 h and then filtrated. Each solution was concentrated under reduced pressure to give the corresponding extract: To-dokkatsu (1.00 g), Kyokatsu (1.45 g), Byakushi (0.70 g), Hakuryo-dokkatsu (1.00 g), Gyubidokkatsu (1.17 g), Jashoshi (0.40 g), and Taiwan-jashoshi (0.40 g).Drugs Fourteen coumarins (1-7, 9, 11-16, Fig. 1) were isolated from the Umbelliferae crude drugs.4-10) The isolation yields of each compound are depicted in Table 1. Synthetic melanin and 0.4 M HEPES buffer (pH 6.8) were purchased from Sigma-Aldrich Japan (Tokyo, Japan). Dulbecco's modified Eagle medium (D-MEM), Antibiotic-Antimycotic (a mixture of 10000 U/ml penicillin, 10000 mg/ml streptomycin sulfate, and 25 mg/ml amphotericine B), Dulbecco's phosphate buffered saline (Ca Isolation of Heraclenin (8) and Heraclenol (10) from Hakuryo-dokkatsu (H. candicans WALL.) Powdered Hakuryo-dokkatsu (500 g) was successively extracted with hexane (5 l) and EtOAc (5 l) under reflux for 2 h. Each extract was evaporated under reduced pressure to give a hexane ex-

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Section: Discussionmentioning

confidence: 92%

“…The results concerning the melanogenesis activities of sixteen coumarins (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16) are shown in Fig. 3.…”

Section: Discussionmentioning

confidence: 99%

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Melanogenesis Stimulation in Murine B16 Melanoma Cells by Umberiferae Plant Extracts and Their Coumarin Constituents

Matsuda

Hirata

Kawaguchi

et al. 2005

Biological & Pharmaceutical Bulletin

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“…The mutagenic activity of compounds such as 8-methoxypsoralen (xanthotoxin) and 5-methoxypsoralen (bergapten) is well established, and reports have appeared documenting the tumorogenic activity of psoralens in a number of species, including man (Ashwood-Smith et al, 1980;Stern et al, 1979;Epstein, 1979).…”

mentioning

confidence: 99%

The psoralen-DNA photoreaction. Characterization of the monoaddition products from 8-methoxypsoralen and 4,5',8-trimethylpsoralen

Kanne¹,

Straub²,

Rapoport³

et al. 1982

Biochemistry

204

129

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“…In addition, experimental evidence demonstrates that the phytocomplex may interfere with the receptor-mediated mechanisms of regulation of synaptic levels of amino acid neurotransmitters [28]. Then, the bergapten compound binding to DNA under ultraviolet A light exposure, produces compounds which are cytotoxic and highly mutagenic [29,30]. So, bergamot essence was restricted or banned in many countries, because of certain adverse effects, due to photosensitive and melanogenic properties of bergapten; in fact, the bergapten-free extract of the essence are prepared by extractive industries for perfumery and cosmetic uses.…”

Section: Cosmetic Usementioning

confidence: 99%

The Fascinating History of Bergamot (Citrus Bergamia Risso & Poiteau), the Exclusive Essence of Calabria: A Review

Maruca¹,

Laghetti²,

Mafrica³

et al. 2017

JESE-A

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Abstract:The bergamot (Citrus bergamia Risso et Poiteau), a citrus fruit growing almost exclusively in the South Italy, is considered the "prince of citrus" for its storical role in the perfume industry due to its essential oil, a product in great demand of a pleasant and refreshing scent. Recently, analgesic, anxiolytic, neuroprotective consistent effects have been ascribed to bergamot essential oil when it is used in aromatherapy, for the relief of pain and symptoms associated with stress-induced anxiety and depression. Moreover, today, bergamot fruit due to a considerable abundance and variety of nutraceutical compounds which are present in its juice, is becoming increasingly important also in the food, pharmaceutical and confectionery industries. In this review, it is discussed that the literature on C. bergamia, focusing on the several studies performed with the experimental data, and recently accumulated, may form the rational basis for further development.

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5-Methoxypsoralen, an ingredient in several suntan preparations, has lethal, mutagenic and clastogenic properties

Cited by 176 publications

References 36 publications

Melanogenesis Stimulation in Murine B16 Melanoma Cells by Umberiferae Plant Extracts and Their Coumarin Constituents

Melanogenesis Stimulation in Murine B16 Melanoma Cells by Umberiferae Plant Extracts and Their Coumarin Constituents

The psoralen-DNA photoreaction. Characterization of the monoaddition products from 8-methoxypsoralen and 4,5',8-trimethylpsoralen

The Fascinating History of Bergamot (Citrus Bergamia Risso & Poiteau), the Exclusive Essence of Calabria: A Review

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