(±)-Walskiiglucinol A, a pair of rearranged acylphloroglucinol derivative enantiomers from Hypericum przewalskii

Abstract

A pair of rearranged acylphloroglucinol derivative enantiomers with a 1-oxaspiro[4.4]nonane skeleton, derived from monocyclic polyprenylated acylphloroglucinols (MPAPs), was obtained from Hypericum przewalskii.

(±)-Hypandrone A, a pair of polycyclic polyprenylated acylphloroglucinol enantiomers with a caged 7/6/5/6/6 pentacyclic skeleton from Hypericum androsaemum

“…(±)-Hypandrone A ((±)- 1 ) represent a new type of PPAPs with an unprecedented 7/6/5/6/6 pentacyclic skeleton, and are distinguished from the reported PPAP-class natural products. In nature, chiral natural products are usually produced in the optically pure form, where on occasion nature is known to produce opposite enantiomeric metabolites, such as (±)-garmultin A, 17 (±)-garcimulin A, 9 (±)-walskiiglucinol A, 18 etc . Presumably, different precursors before the biosynthetic cyclization reactions may be the main reason for the phenomenon.…”