1943
DOI: 10.1021/ja01249a023
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The Isolation of Photosensitizing Agents from Buckwheat1

Abstract: It has been shown that M-butyllithium dimetalates 9-phenylcarbazole homonuclearly to give, subsequent to earbonation and hydrolysis, 9-(2',-6'-dicarboxyphenyl)-carbazole. The structure of this dibasic acid was established by cyclodehydration reactions. Some experiments concerned with resolution studies of cyclodehydration derivatives are described.

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Cited by 22 publications
(15 citation statements)
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“…These data indicate that the compound I has a structure, 1, 12-bis-(2-hydroxypropyl)-2, 6, 7, 11-tetramethoxy-4, 9-dihydroxyperylene-3, 10-quinone (Fig. 1) It has been known that some of the compounds derived from 4, 9-dihydroxyperylene-3, lO-quinone are related to photogenic disease (e. g. hypericism,6) fagopyrism 7 » and/or show a photodynamic nature; the compounds belonging to the former are hypericin S ) and fagopyrin, S) and those of the latter are erythroapines,9) fagopyrin,rO) elsinochromes 3 ) and cercosporin. It is interesting that phleichrome which showed the phytotoxic activity has a structural similarity with those physiological active compounds described above.…”
mentioning
confidence: 81%
“…These data indicate that the compound I has a structure, 1, 12-bis-(2-hydroxypropyl)-2, 6, 7, 11-tetramethoxy-4, 9-dihydroxyperylene-3, 10-quinone (Fig. 1) It has been known that some of the compounds derived from 4, 9-dihydroxyperylene-3, lO-quinone are related to photogenic disease (e. g. hypericism,6) fagopyrism 7 » and/or show a photodynamic nature; the compounds belonging to the former are hypericin S ) and fagopyrin, S) and those of the latter are erythroapines,9) fagopyrin,rO) elsinochromes 3 ) and cercosporin. It is interesting that phleichrome which showed the phytotoxic activity has a structural similarity with those physiological active compounds described above.…”
mentioning
confidence: 81%
“…The sensitizing effect of raw buckwheat in several animal species is well known (4,10,11) ; it produces an occasional eruption and irritation of the skin upon exposure to light. This need not interfere with its potential use in vegetable formulas for human consumption since these are invariably cooked and since buckwheat flour has been extensively used as a staple of human diets.…”
Section: Discussionmentioning
confidence: 99%
“…19 The most promising isolation approach appears to be reported by Samel, 23 but our unpublished reproduction of their procedure was unsuccessful, as we were unable to elute a fluorescent fraction from silica gel 60 with any solvent. 23 In all reported isolation attempts, effective extraction solvents for fagopyrins are evidently highly (5), protofagopyrin (6), and fagopyrin (7).…”
Section: ■ Isolation Attemptsmentioning
confidence: 93%