Bulbinelonesides A-E, phenylanthraquinone glycosides from the roots of Bulbinella floribunda.
The roots of Bulbinella floribunda have been analyzed for the phenolic constituents, resulting in the isolation of five new phenylanthraquinone glycosides, named bulbinelonesides A-E (1-5), along with two known phenylanthraquinones, (+)-M-knipholone (6) and (+)-M-isoknipholone (7). The structures of the new compounds were determined on the basis of extensive spectroscopic analysis, including 2D NMR, and the results of enzymatic hydrolysis. Although the new compounds 3-5, whose absolute stereochemistry of the unsymmetric biaryl moiety was determined to be P by the CD spectrum, did not show apparent cytotoxicity against cultured HSC-2 tumor cells and HPC normal cells, the new compounds 1 and 2, as well as the known compounds 6 and 7, whose biaryl bond was assigned as M, exhibited a tumor-specific cytotoxicity against HSC-2 cells comparable to or slightly weaker than etoposide, used as a positive control.
Kuroda
Minpei
M
Laboratory of Medicinal Plant Science, School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
Mimaki
Yoshihiro
Y
Sakagami
Hiroshi
H
Sashida
Yutaka
Y
D000880:Anthraquinones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002294:Carcinoma, Squamous Cell; D002478:Cells, Cultured / Q000187:drug effects; D002942:Circular Dichroism; D004354:Drug Screening Assays, Antitumor; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D007564:Japan; D019668:Liliaceae / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018517:Plant Roots / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D013237:Stereoisomerism; D014407:Tumor Cells, Cultured / Q000187:drug effects
D000880:Anthraquinones; D000972:Antineoplastic Agents, Phytogenic; D006027:Glycosides