Anti-inflammatory and anti-tumor-promoting effects of 5-deprenyllupulonol C and other compounds from Hop (Humulus lupulus L.).
A new phloroglucinol derivative, 5-deprenyllupulonol C (1), along with four other phloroglucinol derivatives, 2-5, five chalcones, 6-10, four flavanones, 11-14, two flavonol glycosides, 15 and 16, and five triterpenoids, 17-21, were isolated from the female inflorescence pellet extracts of hop (Humulus lupulus L.). Upon evaluation of these compounds against the Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol 13-acetate (TPA) in Raji cells, twelve compounds, i.e., 1-4, 11-14, 17-19, and 21, showed potent inhibitory effects on EBV-EA induction, with IC₅₀ values in the range of 215-393 mol ratio/32 pmol TPA. In addition, eleven compounds, i.e., 1-4, 6, 11, 12, 14, 17, 18, and 20, were found to inhibit TPA-induced inflammation (1 μg/ear) in mice, with ID₅₀ values in the range of 0.13-1.06 μmol per ear. Further, lupulone C (2) and 6-prenylnaringenin (14) exhibited inhibitory effects on skin-tumor promotion in an in vivo two-stage mouse-skin carcinogenesis test based on 7,12-dimethylbenz[a]anthracene (DMBA) as initiator and with TPA as promoter.
College of Science and Technology, Nihon University, 1-8-14 Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan.
Hiroyuki
H
Akazawa
Hideki
H
Kohno
Harukuni
H
Tokuda
Nobutaka
N
Suzuki
Ken
K
Yasukawa
Yumiko
Y
Kimura
Aranya
A
Manosroi
Jiradej
J
Manosroi
Toshihiro
T
Akihisa
D015127:9,10-Dimethyl-1,2-benzanthracene / Q000633:toxicity; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry* / Q000494:pharmacology / Q000627:therapeutic use; D016588:Anticarcinogenic Agents / Q000737:chemistry* / Q000494:pharmacology / Q000627:therapeutic use; D000956:Antigens, Viral / Q000737:chemistry / Q000378:metabolism; D002273:Carcinogens / Q000633:toxicity; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy; D005260:Female; D027582:Humulus / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008968:Molecular Conformation; D010696:Phloroglucinol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D012871:Skin Diseases / Q000139:chemically induced / Q000188:drug therapy; D012878:Skin Neoplasms / Q000139:chemically induced / Q000188:drug therapy; D013755:Tetradecanoylphorbol Acetate / Q000633:toxicity
C575701:5-deprenyllupulonol C; D000893:Anti-Inflammatory Agents; D016588:Anticarcinogenic Agents; D000956:Antigens, Viral; D002273:Carcinogens; C033305:Epstein-Barr virus early antigen; D015127:9,10-Dimethyl-1,2-benzanthracene; D010696:Phloroglucinol; D013755:Tetradecanoylphorbol Acetate