Cytotoxic prenylated xanthones from the young fruit of Garcinia mangostana.
Three new prenylated xanthones, mangostenones C (1), D (2), and E (3), together with 16 known xanthones 4-19, were isolated from the young fruit (7-week maturity stage) of Garcinia mangostana. The structural elucidation of the new compounds was mainly established on the basis of 1D and 2D NMR and HR-MS spectroscopic analysis. Compound 1 showed cytotoxic properties against three human cancer cell lines, epidermoid carcinoma of the mouth (KB), breast cancer (BC-1), and small cell lung cancer (NCI-H187), with IC50 values of 2.8, 3.53, and 3.72 microg/ml, respectively. Among the isolates, alpha-mangostin (12), the major metabolite, exhibited the most potent effects against the BC-1 cells with an IC50 value of 0.92 microg/ml, an activity greater than that of the standard drug ellipticine (IC50 = 1.46 microg/ml). Compound 12 also showed the highest activity against KB cells, while gartanin (10) displayed the strongest activity against the NCI-H187 cells at the respective IC50 values of 2.08 microg/ml and 1.08 microg/ml.
Suksamrarn
Sunit
S
Department of Chemistry, Faculty of Science, Srinakharinwirot University, Sukhumvit, Bangkok, Thailand. sunit@swu.ac.th
Komutiban
Orapin
O
Ratananukul
Piniti
P
Chimnoi
Nitirat
N
Lartpornmatulee
Nattapat
N
Suksamrarn
Apichart
A
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000494:pharmacology*; D002236:Carbohydrate Conformation; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D005638:Fruit / Q000737:chemistry; D029760:Garcinia / Q000737:chemistry*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D014970:Xanthines / Q000737:chemistry / Q000494:pharmacology*
D000972:Antineoplastic Agents, Phytogenic; D014970:Xanthines