Constituents of Cannabis sativa L. XXII: isolation of spiro-indan and dihydrostilbene compounds from a Panamanian variant grown in Mississippi, United States of America

Three spiro-compounds, namely cannabispiran, dehydrocannabispiran and beta-cannabispiranol, and 2 dihydrostilbenes [3-(2-(3-hydroxy-4-methoxyphenyl)ethyl)-5-methoxyphenol and canniprene] were isolated from a polar fraction of a Panamanian variant of Cannabis sativa L. grown in Mississippi, United States of America. The plant material was extracted with 95% ethanol and the dried ethanol extract was then partitioned between chloroform and water. The chloroform fraction was fractionated between hexane and 3N sodium hydroxide solution. Acidification of the basic fraction followed by extraction with ether afforded a polar acidic fraction from which the above-mentioned compounds were isolated through repeated chromatography. The structures of the above compounds were determined by spectral means as well as by comparison with reference samples. The isolation of two dihydrostilbenes and three spiro-indan compounds from a single variant provides good support that the dihydrostilbenes are the natural precursors to the spiro-indan compounds.