Identification of New Diterpenes as Putative Marker Compounds Distinguishing Agnus Castus Fruit (Chaste Tree) from Shrub Chaste Tree Fruit (Viticis Fructus)

Naohiro Oshima; Sayaka Masada; Ryuta Suzuki; Kanae Yagi; Hiroshi Matsufuji; Emi Suenaga; Yutaka Takahashi; Tadahiro Yahagi; Masato Watanabe; Shoji Yahara; Osamu Iida; Nobuo Kawahara; Takuro Maruyama; Yukihiro Goda; Takashi Hakamatsuka

doi:10.1055/s-0035-1558089

Planta Medica, Table of Contents

Planta Med 2016; 82(01/02): 147-153
DOI: 10.1055/s-0035-1558089

Natural Product Chemistry

Original Papers

Georg Thieme Verlag KG Stuttgart · New York

Identification of New Diterpenes as Putative Marker Compounds Distinguishing Agnus Castus Fruit (Chaste Tree) from Shrub Chaste Tree Fruit (Viticis Fructus)

Naohiro Oshima^*

¹Division of Pharmacognosy, Phytochemistry and Narcotics, National Institute of Health Sciences, Tokyo, Japan

,

Sayaka Masada^*

¹Division of Pharmacognosy, Phytochemistry and Narcotics, National Institute of Health Sciences, Tokyo, Japan

,

Ryuta Suzuki

¹Division of Pharmacognosy, Phytochemistry and Narcotics, National Institute of Health Sciences, Tokyo, Japan

,

Kanae Yagi

¹Division of Pharmacognosy, Phytochemistry and Narcotics, National Institute of Health Sciences, Tokyo, Japan

,

Hiroshi Matsufuji

²College of bioresource Sciences, Nihon University, Kanagawa, Japan

,

Emi Suenaga

¹Division of Pharmacognosy, Phytochemistry and Narcotics, National Institute of Health Sciences, Tokyo, Japan

,

Yutaka Takahashi

³MS-Solutions Co. Ltd., Tokyo, Japan

,

Tadahiro Yahagi

⁴School of Pharmaceutical Sciences, International University of Health and Welfare, Tochigi, Japan

,

Masato Watanabe

⁵Medicinal Plants Eco-frontier Center, School of Pharmacy, Kumamoto University, Kumamoto, Japan

,

Shoji Yahara

⁵Medicinal Plants Eco-frontier Center, School of Pharmacy, Kumamoto University, Kumamoto, Japan

,

Osamu Iida

⁶Research Center for Medicinal Plant Resources, National Institute of Biomedical Innovation, Ibaraki, Japan

,

Nobuo Kawahara

⁶Research Center for Medicinal Plant Resources, National Institute of Biomedical Innovation, Ibaraki, Japan

,

Takuro Maruyama

¹Division of Pharmacognosy, Phytochemistry and Narcotics, National Institute of Health Sciences, Tokyo, Japan

,

Yukihiro Goda

¹Division of Pharmacognosy, Phytochemistry and Narcotics, National Institute of Health Sciences, Tokyo, Japan

,

Takashi Hakamatsuka

¹Division of Pharmacognosy, Phytochemistry and Narcotics, National Institute of Health Sciences, Tokyo, Japan

› Author Affiliations

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.

Key words

Vitex agnus-castus - Vitex rotundifolia - Vitex trifolia - Verbenaceae - Lamiaceae - Agnus Castus Fruit (ACF) - Shrub Chaste Tree Fruit (SCTF) - chastol - marker compound

Full Text

References

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