Buy Hyperforin (Hypericum) Cas 11079-53-1

Hyperforin is a phytochemical produced by some of the members of the plant genus Hypericum, notably Hypericum perforatum (St John’s wort).^[2] Hyperforin may be involved in the pharmacological effects of St. John’s wort,^[2] specifically in its antidepressant effects.^[3][4][5] Meta-analyses of clinical trials suggest that H. perforatum is as effective as SSRIs for treating mild to moderate depression and is better tolerated, although findings are limited by short study durations.

Hyperforin is found in significant amounts only in H. perforatum, where it accumulates as a probable plant defense compound, with modern carbon dioxide extraction methods used to isolate it from mixtures containing related compounds like adhyperforin.

Hyperforin has only been found in significant amounts in Hypericum perforatum with other related species such as Hypericum calycinum containing lower levels of the phytochemical.^[2] It accumulates in oil glands, pistils, and fruits, probably as a plant defensive compound.^[6] The first natural extractions were done with ethanol and afforded a 7:1 yield of crude extract to phytochemical however, this technique produced a mixture of hyperforin and adhyperforin.^[3][7][8] The extraction technique has since been modernized using lipophilic liquid CO₂ extraction to afford a 3:1 crude to phytochemical extraction which is then further purified away from adhyperforin.^[3][7][8] This CO₂ extraction is rather tricky still because typical ‘supercritical’ conditions extract less material whereas anything over 40 °C (100 °F) will degrade hyperforin.^[3][7][8] Other Hypericum species contain low amounts of hyperforin.^[9]

Hyperforin is a prenylated phloroglucinol derivative and is a member of the Polycyclic polyprenylated acylphloroglucinol family, also known as the PPAP family. Hyperforin is a unique PPAP because it consists of a C8 quaternary stereocenter which was a synthetic challenge unlike other PPAP synthetic targets.^[3][4][10] The structure of hyperforin was elucidated by a research group from the Shemyakin Institute of Bio-organic Chemistry (USSR Academy of Sciences in Moscow) and published in 1975.^[11][12] A total synthesis of the non-natural hyperforin enantiomer was reported in 2010 which required approximately 50 synthetic transformations.^[13] In 2010, an enantioselective total synthesis of the correct enantiomer was disclosed. The retrosynthetic analysis was inspired by hyperforin’s structural symmetry and biosynthetic pathway. The synthetic route undertaken generated a prostereogenic intermediate which then established the synthetically challenging C8 stereocenter and facilitated the stereochemical outcomes for the remainder of the synthesis.^[10]