title: Identification of New Diterpenes as Putative Marker Compounds Distinguishing Agnus Castus Fruit (Chaste Tree) from Shrub Chaste Tree Fruit (Viticis Fructus).
abstract: Agnus Castus Fruit is defined in the European Pharmacopoeia as the dried ripe fruit of Vitex agnus-castus. In Europe it is used as a medicine targeting premenstrual syndrome and climacteric disorder. In Japan, Agnus Castus Fruit is becoming popular as a raw material for over-the-counter drugs and health food products, though its congenic species, Vitex rotundifolia and Vitex trifolia, have been used as Shrub Chaste Tree Fruit in traditional medicines. Therefore, it is important to discriminate these Vitex plants from the viewpoint of regulatory science. Here we tried to identify putative marker compounds that distinguish between Agnus Castus Fruit and Shrub Chaste Tree Fruit. We analyzed extracts of each crude drug by liquid chromatography-mass spectrometry, and performed differential analysis by comparison of each chromatogram to find one or more peaks characteristic of Agnus Castus Fruit. A peak was isolated and identified as an equilibrium mixture of new compounds named chastol (1) and epichastol (1a). The planar structures of 1 and 1a were determined spectroscopically. Their relative configurations were revealed by nuclear Overhauser effect spectroscopy and differential nuclear Overhauser effect-NMR data. Since avoiding contamination from closely related species is needed for the quality control of natural pharmaceuticals, this information will be valuable to establish a method for the quality control of both, Agnus Castus Fruit and Shrub Chaste Tree Fruit products.
authors.affiliation: Division of Pharmacognosy, Phytochemistry and Narcotics, National Institute of Health Sciences, Tokyo, Japan.
authors.forename: Naohiro
authors.initials: N
authors.lastname: Oshima
authors.affiliation: Division of Pharmacognosy, Phytochemistry and Narcotics, National Institute of Health Sciences, Tokyo, Japan.
authors.forename: Sayaka
authors.initials: S
authors.lastname: Masada
authors.affiliation: Division of Pharmacognosy, Phytochemistry and Narcotics, National Institute of Health Sciences, Tokyo, Japan.
authors.forename: Ryuta
authors.initials: R
authors.lastname: Suzuki
authors.affiliation: Division of Pharmacognosy, Phytochemistry and Narcotics, National Institute of Health Sciences, Tokyo, Japan.
authors.forename: Kanae
authors.initials: K
authors.lastname: Yagi
authors.affiliation: College of bioresource Sciences, Nihon University, Kanagawa, Japan.
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Matsufuji
authors.affiliation: Division of Pharmacognosy, Phytochemistry and Narcotics, National Institute of Health Sciences, Tokyo, Japan.
authors.forename: Emi
authors.initials: E
authors.lastname: Suenaga
authors.affiliation: MS-Solutions Co. Ltd., Tokyo, Japan.
authors.forename: Yutaka
authors.initials: Y
authors.lastname: Takahashi
authors.affiliation: School of Pharmaceutical Sciences, International University of Health and Welfare, Tochigi, Japan.
authors.forename: Tadahiro
authors.initials: T
authors.lastname: Yahagi
authors.affiliation: Medicinal Plants Eco-frontier Center, School of Pharmacy, Kumamoto University, Kumamoto, Japan.
authors.forename: Masato
authors.initials: M
authors.lastname: Watanabe
authors.affiliation: Medicinal Plants Eco-frontier Center, School of Pharmacy, Kumamoto University, Kumamoto, Japan.
authors.forename: Shoji
authors.initials: S
authors.lastname: Yahara
authors.affiliation: Research Center for Medicinal Plant Resources, National Institute of Biomedical Innovation, Ibaraki, Japan.
authors.forename: Osamu
authors.initials: O
authors.lastname: Iida
authors.affiliation: Research Center for Medicinal Plant Resources, National Institute of Biomedical Innovation, Ibaraki, Japan.
authors.forename: Nobuo
authors.initials: N
authors.lastname: Kawahara
authors.affiliation: Division of Pharmacognosy, Phytochemistry and Narcotics, National Institute of Health Sciences, Tokyo, Japan.
authors.forename: Takuro
authors.initials: T
authors.lastname: Maruyama
authors.affiliation: Division of Pharmacognosy, Phytochemistry and Narcotics, National Institute of Health Sciences, Tokyo, Japan.
authors.forename: Yukihiro
authors.initials: Y
authors.lastname: Goda
authors.affiliation: Division of Pharmacognosy, Phytochemistry and Narcotics, National Institute of Health Sciences, Tokyo, Japan.
authors.forename: Takashi
authors.initials: T
authors.lastname: Hakamatsuka
mesh_terms: D002853:Chromatography, Liquid; D018744:DNA, Plant; D004224:Diterpenes / Q000302:isolation & purification*; D005060:Europe; D005638:Fruit / Q000737:chemistry; D007564:Japan; D010946:Plants, Medicinal / Q000737:chemistry / Q000145:classification; D011786:Quality Control; D017422:Sequence Analysis, DNA; D013045:Species Specificity; D053719:Tandem Mass Spectrometry; D020950:Vitex / Q000737:chemistry* / Q000145:classification* / Q000235:genetics
chemical_list: D018744:DNA, Plant; D004224:Diterpenes