Acyl flavonoids, biflavones, and flavonoids from Cephalotaxus harringtonia var. nana

• Published in: Journal of natural medicines 2015-10, Vol.69 (4), p.479-486
• Main Authors: Komoto, Noriko, Nakane, Takahisa, Matsumoto, Sachiko, Hashimoto, Shusuke, Shirota, Osamu, Sekita, Setsuko, Kuroyanagi, Masanori
• Format: Article
• Language: English
• Subjects: Biological Products - chemistry; Biomedical and Life Sciences; Biomedicine; Chromatography, High Pressure Liquid; Complementary & Alternative Medicine; Flavonoids - chemistry; Harringtonines - chemistry; Humans; Magnetic Resonance Spectroscopy; Medicinal Chemistry; Molecular Structure; Original Paper; Pharmacology/Toxicology; Pharmacy; Plant Leaves - chemistry; Plant Sciences
• ISSN: 1340-3443; 1861-0293
• DOI: 10.1007/s11418-015-0912-x

A methanol extract of the leaves of Cephalotaxus harringtonia var. nana and its ethyl acetate (EtOAc)-soluble fraction demonstrated strong antitumor activity against A549 and HT-29 cell lines. The EtOAc-soluble fraction was purified by column chromatography and high-performance liquid chromatography (HPLC) using a reverse-phase column to yield three novel acyl flavonoids and a biflavonoid, along with 15 other known compounds that included flavonoids, biflavonoids, and other phenolics. The structures of the new compounds were elucidated using spectral data from HR-MS and NMR, including two-dimensional NMR studies, as (2 R, 3 R )-3- O -eicosanoyltaxifolin ( 1 ), (2 R ,3 R )-3- O -docosanoyltaxifolin ( 2 ), (2 R ,3 R )-3- O -tetracosanoyltaxifolin ( 3 ), and 6-methyl-4′,7,7″-tri- O -methylamentoflavone ( 4 ). The isolated compounds, including the known compounds, were tested for possible antitumor activity; some of the biflavones were found to be active. The potent antitumor activity of the extract was attributed to Cephalotaxus alkaloids, such as homoharringtonine ( 20 ).