Ultrasound-assisted conversion of toxic beta-asarone into nontoxic bioactive phenylpropanoid: isoacoramone, a metabolite of Piper marginatum and Acorus tararinowii.
Ultrasound-assisted synthesis of bioactive isoacoramone (1), a metabolite of Piper marginatum and Acorus tararinowii, has been achieved by oxidation of toxic beta-asarone (2) with potassium permanganate/copper sulphate/alumina into asaronaldehyde (3) followed by treatment with ethylmagnesium iodide to provide 1-(2,4,5-trimethoxy)phenyl-1-propanol (4) which upon further oxidation with potassium permanganate/copper sulphate afforded 1 in 64% yield (overall 32%). Toxicological evaluation of 1 reveals it to be nontoxic up to 60 mg/kg b.w.
Sinha
A K
AK
Natural Plant Products Division, Institute of Himalayan Bioresource Technology, Palampur, HP 176061, India. aksinha8@rediffmail.com
Joshi
B P
BP
Sharma
A
A
Goel
H C
HC
Prasad
J
J
D029023:Acorus / Q000737:chemistry*; D000081248:Allylbenzene Derivatives; D000840:Anisoles / Q000737:chemistry* / Q000633:toxicity; D002273:Carcinogens / Q000737:chemistry* / Q000633:toxicity; D010084:Oxidation-Reduction; D010666:Phenylpropionates / Q000302:isolation & purification* / Q000633:toxicity; D031701:Piper / Q000737:chemistry*; D014465:Ultrasonics
D000081248:Allylbenzene Derivatives; D000840:Anisoles; D002273:Carcinogens; D010666:Phenylpropionates; C012195:asarone; C486666:isoacoramone