Bioassay and ultraperformance liquid chromatography/mass spectrometry guided isolation of apoptosis-inducing benzophenones and xanthone from the pericarp of Garcinia yunnanensis Hu.
Bioassay and ultraperformance liquid chromatography/photodiode array/mass spectrometry (UPLC/PDA/MS) guided isolation of the apoptosis-inducing active metabolites on HeLa-C3 cells from the pericarp of Garcinia yunnanensis (Guttiferae) yielded five active compounds, including the new garciyunnanins A (1) and B (2). The structures of the compounds were elucidated by comprehensive nuclear magnetic resonance and mass spectrometry analysis. Garciyunnanin B (2), featured with a natural tetracyclic xanthone skeleton derived from a polyisoprenylated benzophenone, is structurally interesting since it can be seen as an evidence of the previously described cyclization of garcinol by 2,2-diphenyl-1-picrylhydrazyl (DPPH). Garciyunnanin A (1) contains a 3-monohydroxy benzophenone skeleton, which is rarely found in Garcinia species. Both new compounds induce HeLa-C3 cells into apoptosis after 72 h of incubation at 15 microM. It is noteworthy that oblongifolin C (4), the major constituent of this plant, has proved to be the most active one among the isolates for inducing apoptotic cell death in cervical cancer derived HeLa-C3 sensor cells.
Xu
Gang
G
Hong Kong Jockey Club Institute of Chinese Medicine, Shatin, Hong Kong, People's Republic of China.
Feng
Chao
C
Zhou
Yan
Y
Han
Quan-Bin
QB
Qiao
Chun-Feng
CF
Huang
Sheng-Xiong
SX
Chang
Donald C
DC
Zhao
Qin-Shi
QS
Luo
Kathy Q
KQ
Xu
Hong-Xi
HX
D017209:Apoptosis / Q000187:drug effects*; D001577:Benzophenones / Q000032:analysis* / Q000302:isolation & purification / Q000494:pharmacology*; D001681:Biological Assay; D002853:Chromatography, Liquid; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D029760:Garcinia / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D013058:Mass Spectrometry; D044004:Xanthones / Q000032:analysis* / Q000302:isolation & purification / Q000494:pharmacology*
D001577:Benzophenones; D004365:Drugs, Chinese Herbal; D044004:Xanthones; C009689:xanthone