Acerogenin M, a cyclic diarylheptanoid, and other phenolic compounds from Acer nikoense and their anti-inflammatory and anti-tumor-promoting effects.
A new cyclic diarylheptanoid, acerogenin M (1), has been isolated along with nine known diarylheptanoids, 2-10, and two known phenolic compounds, 11 and 12, from a MeOH extract of the stem bark of Acer nikoense MAXIM. (Aceraceae). The structure of 1 was determined on the basis of a spectroscopic method. Upon evaluation of the inhibitory effects on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1 microg/ear) in mice of nine of the compounds (2-6, 8, 10-12), six (2, 4-6, 8, 10) showed a marked anti-inflammatory effect with a 50% inhibitory dose (ID(50)) of 0.26-0.81 mg per ear. In addition, upon an evaluation against the Epstein-Barr virus early antigen (EBV-EA) activation induced by TPA for all of the compounds, all exhibited moderate inhibitory effects against EBV-EA induction (IC(50) values of 356-534 mol ratio/32 pmol TPA).
Akihisa
Toshihiro
T
College of Science and Technology, Nihon University, 1-8 Kanda Surugadai, Chiyoda-ku, 101-8308 Tokyo, Japan. akihisa@chem.cst.nihon-u.ac.jp
Taguchi
Yosuke
Y
Yasukawa
Ken
K
Tokuda
Harukuni
H
Akazawa
Hiroyuki
H
Suzuki
Takashi
T
Kimura
Yumiko
Y
D031002:Acer / Q000737:chemistry*; D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry* / Q000494:pharmacology*; D016588:Anticarcinogenic Agents / Q000737:chemistry* / Q000494:pharmacology*; D002460:Cell Line; D036381:Diarylheptanoids / Q000737:chemistry / Q000494:pharmacology*; D004431:Ear, External / Q000473:pathology; D004487:Edema / Q000139:chemically induced / Q000517:prevention & control; D005260:Female; D004854:Herpesvirus 4, Human / Q000187:drug effects; D006801:Humans; D007564:Japan; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008813:Mice, Inbred ICR; D010636:Phenols / Q000737:chemistry* / Q000494:pharmacology*; D024301:Plant Bark / Q000737:chemistry; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology; D018547:Plant Stems / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D013755:Tetradecanoylphorbol Acetate; D000097566:Cyclophanes
D000894:Anti-Inflammatory Agents, Non-Steroidal; D016588:Anticarcinogenic Agents; D036381:Diarylheptanoids; D010636:Phenols; D010936:Plant Extracts; D013755:Tetradecanoylphorbol Acetate; C511426:acerogenin M; D000097566:Cyclophanes