title: Characterization of natural aryl hydrocarbon receptor agonists from cassia seed and rosemary.
abstract: Many recent studies have suggested that activation of the aryl hydrocarbon receptor (AhR) reduces immune responses, thus suppressing allergies and autoimmune diseases. In our continuing study on natural AhR agonists in foods, we examined the influence of 37 health food materials on the AhR using a reporter gene assay, and found that aqueous ethanol extracts of cassia seed and rosemary had particularly high AhR activity. To characterize the AhR-activating substances in these samples, the chemical constituents of the respective extracts were identified. From an active ethyl acetate fraction of the cassia seed extract, eight aromatic compounds were isolated. Among these compounds, aurantio-obtusin, an anthraquinone, elicited marked AhR activation. Chromatographic separation of an active ethyl acetate fraction of the rosemary extract gave nine compounds. Among these compounds, cirsimaritin induced AhR activity at 10-10² μM, and nepitrin and homoplantagenin, which are flavone glucosides, showed marked AhR activation at 10-10³ μM.
authors.affiliation: College of Pharmaceutical Sciences, Matsuyama University, 4-2 Bunkyo-cho, Matsuyama, Ehime 790-8578, Japan. amakura@cc.matsuyama-u.ac.jp.
authors.forename: Yoshiaki
authors.initials: Y
authors.lastname: Amakura
authors.affiliation: College of Pharmaceutical Sciences, Matsuyama University, 4-2 Bunkyo-cho, Matsuyama, Ehime 790-8578, Japan. myoshimu@cc.matsuyama-u.ac.jp.
authors.forename: Morio
authors.initials: M
authors.lastname: Yoshimura
authors.affiliation: College of Pharmaceutical Sciences, Matsuyama University, 4-2 Bunkyo-cho, Matsuyama, Ehime 790-8578, Japan. matakaoka@shikoku-cc.go.jp.
authors.forename: Masashi
authors.initials: M
authors.lastname: Takaoka
authors.affiliation: College of Pharmaceutical Sciences, Matsuyama University, 4-2 Bunkyo-cho, Matsuyama, Ehime 790-8578, Japan. aranharu.0205@gmail.com.
authors.forename: Haruka
authors.initials: H
authors.lastname: Toda
authors.affiliation: Division of Foods, National Institute of Health Sciences, 1-18-1 Kamiyoga, Setagaya-ku, Tokyo 158-8501, Japan. tutumi@nihs.go.jp.
authors.forename: Tomoaki
authors.initials: T
authors.lastname: Tsutsumi
authors.affiliation: Division of Foods, National Institute of Health Sciences, 1-18-1 Kamiyoga, Setagaya-ku, Tokyo 158-8501, Japan. matsuda@nihs.go.jp.
authors.forename: Rieko
authors.initials: R
authors.lastname: Matsuda
authors.affiliation: Division of Foods, National Institute of Health Sciences, 1-18-1 Kamiyoga, Setagaya-ku, Tokyo 158-8501, Japan. rteshima@nihs.go.jp.
authors.forename: Reiko
authors.initials: R
authors.lastname: Teshima
authors.affiliation: Hiyoshi Corporation, 908 Kitanosho-cho, Omihachiman, Shiga 523-8555, Japan. m.nakamura@hiyoshi-es.co.jp.
authors.forename: Masafumi
authors.initials: M
authors.lastname: Nakamura
authors.affiliation: Hiyoshi Corporation, 908 Kitanosho-cho, Omihachiman, Shiga 523-8555, Japan. handa@hiyoshi-es.co.jp.
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Handa
authors.affiliation: College of Pharmaceutical Sciences, Matsuyama University, 4-2 Bunkyo-cho, Matsuyama, Ehime 790-8578, Japan. tyoshida@gem.e-catv.ne.jp.
authors.forename: Takashi
authors.initials: T
authors.lastname: Yoshida
mesh_terms: D000818:Animals; D000880:Anthraquinones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D002366:Cassia / Q000737:chemistry*; D045744:Cell Line, Tumor; D047309:Flavones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D015870:Gene Expression / Q000187:drug effects; D017930:Genes, Reporter; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D022781:Hepatocytes / Q000166:cytology / Q000187:drug effects / Q000378:metabolism; D006801:Humans; D007155:Immunologic Factors / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D029794:Ledum / Q000737:chemistry*; D008156:Luciferases / Q000235:genetics / Q000378:metabolism; D047311:Luteolin / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D051379:Mice; D010936:Plant Extracts / Q000737:chemistry; D018515:Plant Leaves / Q000737:chemistry*; D018336:Receptors, Aryl Hydrocarbon / Q000819:agonists* / Q000235:genetics / Q000378:metabolism; D012639:Seeds / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: C403862:6-methoxy-4',5-dihydroxyflavone-7-O-glucoside; D000880:Anthraquinones; D047309:Flavones; D005419:Flavonoids; D005960:Glucosides; D007155:Immunologic Factors; D010936:Plant Extracts; D018336:Receptors, Aryl Hydrocarbon; C007072:cirsimaritin; D008156:Luciferases; D047311:Luteolin; C035839:nepitrin
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