Triterpene acids from the leaves of Perilla frutescens and their anti-inflammatory and antitumor-promoting effects.
Nine triterpene acids, viz., six of the ursane type, ursolic acid (1), corosolic acid (2), 3-epicorosolic acid (3), pomolic acid (4), tormentic acid (5) and hyptadienic acid (6), and three of the oleanane type, oleanolic acid (7), augustic acid (8) and 3-epimaslinic acid (9), among which 1 constituted the most predominant triterpene acid, were isolated and identified from ethanol extracts of the leaves of red perilla [Perilla frutescens (L.) Britton var. acuta Kudo] and green perilla [P. frutescens (L.) Britton var. acuta Kudo forma viridis Makino]. These eight compounds, 1, 2, 4-9, were evaluated for their inhibitory effects on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1 microg/ear) in mice. All the compounds tested showed a marked anti-inflammatory effect, with a 50% inhibitory dose (ID50) of 0.09-0.3 mg per ear. In addition, an evaluation against the Epstein-Barr virus early antigen (EBV-EA) activation induced by TPA showed five compounds, 1-3, 5 and 9, with a potent inhibitory effect on EBV-EA induction (91-93% inhibition at 1x10(3) mol ratio/TPA). Furthermore, compound 5 exhibited strong antitumor-promoting activity in an in vivo two-stage carcinogenesis test of mouse tumor by using 7,12-dimethylbenz(a)anthracene (DMBA) as an initiator and TPA as a promoter.
Banno
Norihiro
N
Ichimaru Pharcos Company Ltd., Gifu, Japan.
Akihisa
Toshihiro
T
Tokuda
Harukuni
H
Yasukawa
Ken
K
Higashihara
Hiroshi
H
Ukiya
Motohiko
M
Watanabe
Kenji
K
Kimura
Yumiko
Y
Hasegawa
Jun-Ichi
J
Nishino
Hoyoku
H
D015127:9,10-Dimethyl-1,2-benzanthracene / Q000009:adverse effects; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000494:pharmacology*; D000956:Antigens, Viral / Q000187:drug effects; D000970:Antineoplastic Agents / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004353:Drug Evaluation, Preclinical / Q000379:methods; D005260:Female; D051379:Mice; D008813:Mice, Inbred ICR; D010031:Otitis / Q000139:chemically induced / Q000188:drug therapy; D010212:Papilloma / Q000139:chemically induced / Q000188:drug therapy; D031344:Perilla frutescens / Q000737:chemistry*; D018515:Plant Leaves / Q000737:chemistry; D012878:Skin Neoplasms / Q000139:chemically induced / Q000188:drug therapy; D013755:Tetradecanoylphorbol Acetate / Q000009:adverse effects / Q000494:pharmacology; D014315:Triterpenes / Q000302:isolation & purification / Q000494:pharmacology*
D000893:Anti-Inflammatory Agents; D000956:Antigens, Viral; D000970:Antineoplastic Agents; C033305:Epstein-Barr virus early antigen; D014315:Triterpenes; C007695:euscaphic acid; D015127:9,10-Dimethyl-1,2-benzanthracene; D013755:Tetradecanoylphorbol Acetate