Tetrahydroxanthene-1,3(2H)-dione derivatives from Uvaria valderramensis.
Two tetrahydroxanthene-1,3(2H)-dione metabolites, valderramenols A (1) and B (2), were isolated from the Philippine endemic Annonaceous species Uvaria valderramensis. Planar structures of the rac-xanthene-1,3-(2H)-diones 1 and 2 were established by MS and NMR measurements. Their enantiomers were separated by chiral HPLC, and the absolute configurations of the separated enantiomers were determined by comparison of the HPLC-ECD spectra with computed TDDFT-generated spectra. A TDDFT-ECD study of the known grandiuvarone (3) allowed the revision of its absolute configuration as S. Compound 1 showed antitubercular activity (MIC 10 μg/mL), while 3 and 4 had weaker activities (MIC 32 μg/mL). Oxepinone 3 exhibited cytotoxic activity against KB-562, a chronic myeloid leukemia cell line.
Phytochemistry and Organic Synthesis Laboratory, and ⊥Plant Sciences Laboratory, Research Center for the Natural and Applied Sciences, University of Santo Tomas , 1015 Manila, Philippines.
Allan Patrick G
AP
Macabeo
Franze Perry A
FP
Martinez
Tibor
T
Kurtán
László
L
Tóth
Attila
A
Mándi
Sebastian
S
Schmidt
Jörg
J
Heilmann
Grecebio Jonathan D
GJ
Alejandro
Matthias
M
Knorn
Hans-Martin
HM
Dahse
Scott G
SG
Franzblau
D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D004354:Drug Screening Assays, Antitumor; D007951:Leukemia, Myeloid / Q000188:drug therapy; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010679:Philippines; D018515:Plant Leaves / Q000737:chemistry; D013237:Stereoisomerism; D031046:Uvaria / Q000737:chemistry*; D044004:Xanthones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D000970:Antineoplastic Agents; D044004:Xanthones; C000595537:valderramenol A; C000595538:valderramenol B