Unprecedented polycyclic polyprenylated acylphloroglucinols with anti-Alzheimer's activity from St. John's wort.

ABSTRACT: Hyperforones A-J (1-10), ten degraded and reconstructed polycyclic polyprenylated acylphloroglucinols (PPAPs) with six different types of unusual architectures, were isolated from Hypericum perforatum (St. John's wort). Compound 1 is characterized by an unprecedented 1,5-epoxyfuro[3',4':1,5]cyclopenta[1,2-c]oxecine ring system; compounds 2 and 3 represent the first PPAPs with a contracted B-ring leading to the unique 5/5 core skeletons; compound 4, a proposed biosynthetic precursor of 2, is defined by an oxonane-2,7-dione architecture; compound 5 features an unusual spiro[furo[3',4':1,5]cyclopenta[1,2-b]oxepine-3,2'-oxetane] ring system; compounds 6-8 possess a rare macrocyclic lactone ring in addition to the newl

SUBMITTER: Guo Y 

PROVIDER: S-EPMC8409492 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature