Protoapigenin

[Flavonoids with special B-ring from Macrothelypteris viridifrons and their anti-proliferative effects on tumor cell].[Pubmed:21657076]

Zhongguo Zhong Yao Za Zhi. 2011 Mar;36(5):582-4.

OBJECTIVE: To study the chemical constituents of Macrothelypteris viridifrons and their anti-proliferative effects on tumor cell. METHOD: The compounds were isolated by column chromatography with silica gel, C18 reverse-phase silica gel, sephadex LH-20, and their structures were elucidated on the basis of physiochemical propertities and spectral analysis. The antitumor activities of all compounds were tested with MOLT4, Hep G2, A-549, MCF-7, HT-29, PC-3 tumor cell lines. RESULT: Five compounds were isolated and identified as protoapigenone (1), Protoapigenin (2), Protoapigenin-4'-O-beta-D-glucopyanoside (3), 5,7-dihydroxy-2-(1,2-isopropyldioxy-4-oxo-cyclohex-5-enyl) -chromen-4-one (4), 5,7-dihydroxy-2-(1-hydroxy-2,6-dimethoxy-cyclohex-4-oxo) -chromen-4-one (5), respectively. CONCLUSION: All compounds were obtained from this plant for the first time. Compounds 1, 4 and 5 showed strong anti-proliferative effects on six tumor cells, which were in concentration-dependent manner.

Flavonoids from the aerial parts of Macrothelypteris torresiana.[Pubmed:21240759]

Nat Prod Res. 2011 Jan;25(1):36-9.

Two new flavone derivatives (1 and 2) were isolated from the aerial parts of Macrothelypteris torresiana, along with four known flavonoids: Protoapigenin, apigenin, kaempferol and quercetin. The structures were determined on the basis of spectroscopic data. Compound 1 showed weak cytotoxic activity against human tumour cell lines HepG(2) , MCF(7) and K562.

Protoflavonoids from ferns impair centrosomal integrity of tumor cells.[Pubmed:20945277]

Planta Med. 2011 Mar;77(5):461-6.

Six protoflavonoids, including two new compounds, were isolated during a large scale screening of fern extracts for original interaction with mitosis. The new compounds isolated from PHEGOPTERIS decursive-pinnata and EQUISETUM fluviatile were 2',3'-dihydroprotogenkwanone (1) and 2',3'-dihydro-2'-hydroxyprotoapigenone (2). Known compounds were: protoapigenone, protogenkwanone, Protoapigenin, and 4'- O- beta-D-glucopyranosyl Protoapigenin. They showed a cytotoxic activity against HeLa cells at a micromolar level. IC(5)(0) values were 2 microM for compound 1 > 10 microM for compound 2, and respectively 2.4, 0.6, > 10 microM for the known compounds. Their cytotoxic effects were associated with phenotypic changes never observed before and characterized by the loss of centrosomal gamma-tubulin labelling in both mitotic and interphasic cells.

New cytotoxic flavonoids from Thelypteris torresiana.[Pubmed:16206043]

Planta Med. 2005 Sep;71(9):867-70.

During our search for anti-tumor agents from pteridophytes, three new flavonoids, protoapigenone (1), 5',6'-dihydro-6'-methoxyprotoapigenone (2), and Protoapigenin (3), along with four known compounds, Protoapigenin 4'- O-beta- D-glucoside (4), apigenin 4'- O-beta- D-glucoside (5), kaempferol 3- O-alpha- L-rhamnopyranoside (6), kaempferol 3,7-di- O-alpha- L-rhamnopyranoside (7), were isolated from Thelypteris torresiana using bioactivity-guided fractionation methods . The structures of the new isolates were elucidated by 1D- and 2D-NMR spectral analysis. Among the 7 compounds, protoapigenone (1) exhibited significant anti-tumor activities toward Hep G2, Hep 3B, MCF-7, A549, and MDA-MB-231 with IC50 values of 1.60, 0.23, 0.78, 3.88 and 0.27 microg/mL, respectively.