Isolation and structure of ruprechstyril from Ruprechtia tangarana.
Bioassay (P388 lymphocytic leukemia cell line and human cancer cell lines)-guided separation of an extract prepared from the stem bark and twigs of the previously uninvestigated Ruprechtia tangarana led to the isolation of a new isocarbostyril designated ruprechstyril (1), secalonic acid A (2), 2'-O-methylevernic acid (3), 3,3',4-tri-O-methylflavellagic acid (4), lichexanthone (5), methyl asterrate (6), and 3beta,22E,24S-stigmasta-5,22-dien-3-ol (7). Only secalonic acid A exhibited cancer cell and microbial growth inhibition. The structure of ruprechstyril (1) was determined by HRMS and 1D and 2D NMR spectra and confirmed by single-crystal X-ray analysis. The structures and absolute stereochemistry of five of the other compounds were also established by X-ray crystal structure determination.
Pettit
George R
GR
Cancer Research Institute and Department of Chemistry and Biochemistry, Arizona State University, Tempe, Arizona 85287-2404, USA. bpettit@asu.edu
Meng
Yanhui
Y
Herald
Delbert L
DL
Graham
Keith A N
KA
Pettit
Robin K
RK
Doubek
Dennis L
DL
D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D006912:Hydroxyquinolines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007941:Leukemia P388; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010568:Peru; D010946:Plants, Medicinal / Q000737:chemistry*; D019664:Polygonaceae / Q000737:chemistry*; D013237:Stereoisomerism
D000972:Antineoplastic Agents, Phytogenic; D006912:Hydroxyquinolines; C479808:ruprechstyril