title: Androgen modulators from the roots of Paeonia lactiflora (paeoniae radix) grown and processed in nara prefecture, Japan.
abstract: The monoterpene glycoside, 3'-O-galloylpaeoniflorin (1), and four known compounds, 6'-O-galloylalbiflorin (2), pentagalloylglucose (3), 6'-O-benzoylpaeoniflorin (4) and 6'-O-galloylpaeoniflorin (5), were isolated from the roots of Paeonia lactiflora that had been grown and processed in Nara prefecture, Japan, as androgen modulators. Their structures were elucidated based on spectroscopic analysis. Compounds 2 and 3 showed strong androgen receptor (AR) binding activity (IC(50) values 33.7 and 4.1 microg/ml, respectively), 1, 4 and 5 showed weak activity (20, 31 and 12% at 120 microg/ml, respectively). However, paeoniflorin (6) and albiflorin (7), the structures of which are related to 1, 2, 4 and 5, showed no activity. These results suggested that both the structure of albiflorin and the galloyl moiety are important for 2 to show strong AR binding activity. Furthermore, compounds 1-5 inhibited growth of an androgen-dependent LNCaP-FGC (prostate cancer cell line), and were indicated to be AR antagonists. Compounds 2 and 3 might be candidates as safe, natural anti-androgens.
authors.affiliation: Nara Prefectural Small and Medium-sized Enterprises Support Corporation, Nara Prefectural Agricultural Experiment Station, Japan. kwashida@festa.ocn.ne.jp
authors.forename: Kazuto
authors.initials: K
authors.lastname: Washida
authors.forename: Yoshiyuki
authors.initials: Y
authors.lastname: Itoh
authors.forename: Takashi
authors.initials: T
authors.lastname: Iwashita
authors.forename: Kyosuke
authors.initials: K
authors.lastname: Nomoto
mesh_terms: D000726:Androgen Antagonists / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D059002:Androgen Receptor Antagonists; D045744:Cell Line, Tumor; D006801:Humans; D007564:Japan; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D039821:Monoterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D029596:Paeonia / Q000737:chemistry*; D018517:Plant Roots / Q000737:chemistry; D011944:Receptors, Androgen / Q000378:metabolism
chemical_list: D000726:Androgen Antagonists; D059002:Androgen Receptor Antagonists; D039821:Monoterpenes; D011944:Receptors, Androgen