Incarvillea sinensis

Incarvillateine was isolated from the aerial parts of the Chinese plant known as jiao-hao, Incarvillea sinensis, in the family Bignoniaceae (48). This plant had not been studied previously, and indeed the genus of 11 species has been afforded scant attention. 

Several derivatives related to incarvilline (35) were also isolated from Incarvillea sinensis. Incarvine A (38), [a]D -0.9° (50), showed a molecular... 

The whole plant of Incarvillea sinensis is used in traditional Chinese medicine as an antirheumatic and analgesic (88). Examination of the alkaloid content led to a number of new monoterpene pyridine alkaloids discussed earlier (see Section II.A.20-22). Biological evaluation of the isolates indicated that incarvillateine (34) at 10 mg/kg i.p. inhibited both the first and second stages of formalin-induced pain and reduced spontaneous motor activity. At lower doses (1-5 mg/kg), the analgesic activity was maintained without sedative activity (88). 

Additional studies on the aerial parts of Incarvillea sinensis led to the isolation of four new monoterpene alkaloids (247). Incarvine D (393), [a]D -4.2°,... 

Incarvillea sinensis has been used in traditional Chinese medicine as a drug to treat rheumatism and relieve pain. Incarvillateine is a monoterpene alkaloid isolated from this plant. When intraperitoneally... 

Alkaloid from aerial parts of Incarvillea sinensis (Bignoniaceae). Powder, [a] -0.9 (CHCI3). 

Chi YM, Nakamura M, Zhao XY et al (2005) A monoterpene alkaloid from Incarvillea sinensis. Chem Pharm Bull 53 1178-1179... 

Huang DS, Zhang WD, Pei Yh, Peng XY, Huang ZS, Li HL, Shen YH (2009) Two new alkaloids from Incarvillea sinensis. Helv Chim Acta 92 1558-1561... 

Nakamura M, Chi YM, Yan WM et al (2000) Structure-antinociceptive activity studies of incarvillateine, a monoterpene alkaloid from Incarvillea sinensis. Planta Med 67 114-117... 

The asymmetric synthesis of the cyclopentane 66, a synthetic intermediate of the alkaloid (—)-incarvillateine 64 (a natural product with potent analgesic properties isolated firom the aerial parts of Incarvillea sinensis Lam.), via a Rh-catalyzed olefin C—H bond activation, is a follow-up of the methodology employed for the total synthesis of (-F)-litho-spermic acid disclosed by Bergman and EUman. The chiral imine 67, prepared in few steps, was submitted to [RhCl (coe)2l2 (coe = cyclooctene) as catalyst under various reaction conditions. The complete conversion of 67 occurred in the presence of a 4-(dimethylamino)phenyl... 

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