Xanthorrhizol

The sesquiterpenoid hydrocarbons (5)-a-curcumene (59) and (5)-xanthorrhizol (60) were prepared by asymmetric conjugate addition of the appropriate aryllithium reagent to unsaturated oxazoline 56 to afford alcohols 57 (66% yield, 96% ee) and 58 (57% yield, 96% ee) upon hydrolysis and reduction. The chiral alcohols were subsequently converted to the desired natural products. ... 

PONCE-MONTER, H., CAMPOS, M.G., AGUILAR, I., DELGADO, G Effect of xanthorrhizol, xanthorrhizol glycoside and trachylobanoic acid isolated from Cachani complex plants upon the contractile activity of uterine smooth muscle., Phytother. Res., 1999,13,202-205. 

An elegant enantiocontrolled, five-step, total synthesis of the sesquiterpenoid plant product (+)-heliannuol D 51 has now been realised starting from (-)-xanthorrhizol and utilising a palladium-catalysed cyclisation to form the seven-membered ring <03H(61)125>. A racemic synthesis of 51 was also reported <03T1679>. 

Reference T1 thymol (—R, range of xanthorrhizol) coiiipouiiit T2 curcumin... 

The phenolic sesquiterpene xanthorrhizol is found as a blue-violet zone at R, — 0.55, directly above the reference compound thymol (Tl). 

Xanthorrhizol is a characteristic constituent of C. zanthorrhiza. Due to the phenolic structure xanthorrhizol and the reference compound thymol (Tl) react to give an intense violet-red when treated with the FBS res ent. 

The di.stillates 2 and 4 from C. zanthorrhiza show xanthorrhizol as a prominenl zone at Rf - 0..55, in lower concentration in oil 3, distilled from commercial C. xanthorrhiza. In oil 1 from Cui cuma domestica, only weak red zone.s can be detected. Very often trade samples are mixtures of both turmeric rhizomes. 

Four anti-tumor bisabolane sesquiterpenes, a-curcumene (224), ar-turmerone (225), P-atlantone (226) and xanthorrhizol (227), were isolated from the rhizomes of C. xanthorrhiza and 224 was reported to be the most active compound [170]. On further examination of the rhizomes, four additional bisabolanes, bisacurone (228), biscumol (229), bisacurol (230) and curlone (231) were obtained [171]. The absolute stereostructures of compounds 228-231 were determined by spectroscopy methods, chemical conversions and the CD exciton chirality method for allylic alcohols [171]. In more work by the same group, four related sesquiterpenes, bisacurone epoxide (232), bisacurone A (233), bisacurone B (234) and bisacurone C (235) were isolated from the same extract and their stereostructures were... 

Rodrfguez JC, Pastor E, Ruiz M, Flores E, Royo G (2007) Antibiotic resistance during therapy mechanisms and means of control. Infect Disord Drug Targets 7 43-45 Rukayadi Y, Hwang JK (2006) Effect of coating the weUs of a polystyrene microtiter plate with xanthorrhizol on the biofilm formation of Streptococcus mutans. J Basic Microbiol 46 410- 15... 

Fuganti, C. and Serra, S. (2000) Baker s yeast-mediated enantiosdective synthesis of the bisabolane sesquiterpenes (+)-curcuphenol, (-l-)-xanthorrhizol, (—)-curcuquinone and (+)-curcuhydroquinone. J. CiKm. Soc. Perkin Trans. I, 3758-3764. 

Montiel, L.E., Zepeda, L.G., and Tamariz, J. (2010) Efficient total synthesis of racemic bisabolane sesquiterpenes curcuphenol and xanthorrhizol starting from substituted acetophenones. Hdv. Chem. Acta, 93,1261-1273. 

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