First total synthesis of structurally unique flavonoids and their strong anti-inflammatory effect

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 12, 2004, Pages 3201-3203

  Nakatsuka, Takashi ^a   Tomimori, Yoshiaki ^a   Fukuda, Yoshiaki ^a   Nukaya, Haruo ^b  

^a SUNTORY LTD   (Japan)

^b UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFLAMMATORY AGENT; FLAVONOID;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; DELAYED HYPERSENSITIVITY; DRUG EFFECT; DRUG STRUCTURE; DRUG SYNTHESIS; MOUSE; NONHUMAN;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; DERMATITIS, CONTACT; FEMALE; FLAVONOIDS; MICE; MICE, INBRED BALB C; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 2442436532     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.03.108     Document Type: Article

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17. 3OD): δ 3.3-3.4 (m, 1H), 3.55-3.65 (m, 2H), 3.82 (dd, 1H, J=3 Hz, 12 Hz), 3.99 (dd, 1H, J=5 Hz, 9 Hz), 4.7-4.75 (m, 1H), 5.22 (d, 1H, J=3 Hz), 6.70 (s, 1H), 6.81 (s, 1H), 7.5-7.6 (m, 3H), 7.95-8.05 (m, 2H)
18. Asherson G.L., Ptak W. Immunology. 15:1968;405. Female BALB/c mice (7-9 weeks old, N=7, Charles River Japan, Inc., Kanagawa) were sensitized by an epicutaneous application with 100 μL of 7% 2, 4, 6-trinitro-1-chlorobenzene (TNCB) (in a 4:1 mixture of acetone and olive oil) to shaved abdomen of mice. Six days after the sensitization, 20 μL of 1% TNCB in acetone/olive oil (1:9) was applied to each side of right ears of the mice to induce contact hypersensitivity response. As a control, the TNCB solution was painted to ears similarly to unsensitized mice. Test compounds were suspended in 0.5% of hydroxy propyl cellulose (HPC) (Nippon Soda Co., Ltd, Tokyo, Japan) and administered orally three times (30 min prior to the elicitation, 6 and 21 h after the elicitation). Ear thickness was measured at 0 and 24 h after the elicitation utilizing a thickness gauge (Digimatic Indicator, Mitsutoyo, Tokyo, Japan), and contact hypersensitivity response was determined by the difference. Betamethasone valerate (Wako pure chemicals, Osaka, Japan) was suspended in 0.5% HPC and administered orally as a positive control. The statistical analysis was performed with Dunnett's multiple comparison test or Student's t -test using SuperANOVA (Abacus Concepts, Berkeley, CA) or Statview (SAS Institute Inc., Cary, NC), respectively. The P -value less than 0.05 was considered significant