Anti-inflammatory and potential cancer chemopreventive constituents of the fruits of Morinda citrifolia (Noni).
A new anthraquinone, 1,5,15-tri-O-methylmorindol (1), and two new saccharide fatty acid esters, 2-O-(beta-D-glucopyranosyl)-1-O-hexanoyl-beta-D-gluropyranose (4) and 2-O-(beta-D-glucopyranosyl)-1-O-octanoyl-beta-D-gluropyranose (5), have been isolated from a methanol extract of the fruits of Morinda citrifolia (noni) along with 10 known compounds, namely, two anthraquinones (2, 3), six saccharide fatty acid esters (6-11), an iridoid glycoside (12), and a flavanol glycoside (13). Upon evaluation of six compounds (5-7, 9, 10, and 13) for inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1 microg/ear) in mice, four saccharide fatty acid esters, 5-7 and 9, exhibited potent anti-inflammatory activity, with ID50 values of 0.46-0.79 mg per ear. In addition, when compounds 1-13 were evaluated against the Epstein-Barr virus early antigen (EBV-EA) activation induced by TPA, all of the compounds exhibited moderate inhibitory effects (IC50 values of 386-578 mol ratio/32 pmol TPA).
Akihisa
Toshihiro
T
College of Science and Technology, Nihon University, 1-8 Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan. akihisa@chem.cst.nihon-u.ac.jp
Matsumoto
Kazumi
K
Tokuda
Harukuni
H
Yasukawa
Ken
K
Seino
Ken-ichi
K
Nakamoto
Katsuo
K
Kuninaga
Hideki
H
Suzuki
Takashi
T
Kimura
Yumiko
Y
D000818:Animals; D000880:Anthraquinones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D016588:Anticarcinogenic Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D000956:Antigens, Viral / Q000187:drug effects; D002208:Caproates / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D002210:Caprylates / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D004423:Ear; D004487:Edema / Q000139:chemically induced; D005638:Fruit / Q000737:chemistry; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D007564:Japan; D051379:Mice; D015394:Molecular Structure; D032066:Morinda / Q000737:chemistry*; D010946:Plants, Medicinal / Q000737:chemistry*; D013755:Tetradecanoylphorbol Acetate / Q000494:pharmacology
C520803:1,5,15-tri-O-methylmorindol-(6-hydroxy-1,5-dimethoxy-2-(methoxymethyl)anthraquinone); C520804:2-O-(beta-D-glucopyranosyl)-1-O-hexanoyl-beta-D-gluropyranose; C520805:2-O-(beta-D-glucopyranosyl)-1-O-octanoyl-beta-D-gluropyranose; D000880:Anthraquinones; D000893:Anti-Inflammatory Agents; D016588:Anticarcinogenic Agents; D000956:Antigens, Viral; D002208:Caproates; D002210:Caprylates; C033305:Epstein-Barr virus early antigen; D005960:Glucosides; D013755:Tetradecanoylphorbol Acetate