Cytotoxic polyprenylated benzoylphloroglucinol derivatives with an unusual adamantyl skeleton from Hypericum sampsonii (Guttiferae).
[formula: see text] The structures of sampsoniones I and J, isolated from the aerial parts of the Chinese medicinal plant Hypericum sampsonii, have been elucidated by detailed spectral analysis. They are complex adamantyl derivatives, and sampsonione I is the first polyprenylated benzoylphloroglucinol derivative with the unique caged tetracyclo[7.3.1.1.0]tetradecane-2,12,14-trione skeleton. Cytotoxic sampsonione I has also been obtained by the biomimetic transformation of sampsonione J.
Hu
L H
LH
Department of Chemistry, National University of Singapore, Kent Ridge, Singapore.
Sim
K Y
KY
D000218:Adamantane / Q000031:analogs & derivatives* / Q000737:chemistry; D020902:Hypericum / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D018716:Molecular Mimicry; D015394:Molecular Structure; D010946:Plants, Medicinal
C409385:sampsonione I; C409384:sampsonione J; D000218:Adamantane