Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia cruciata

Abstract

Seven new bisbibenzyls (1−7) were isolated from the methanol extract of the liverwort Lunularia cruciata along with one previously known bibenzyl and five known bisbibenzyls. The structures of compounds 1−7 were elucidated on the basis of the spectroscopic data. These newly isolated bisbibenzyls may be divided into two groups, the acyclic bisbibenzyls, perrottetins (1− 3), and the cyclic analogues, riccardins (4−7). Besides standard perrottetin and riccardin structures (1 and 4, respectively), they contain phenanthrene (3 and 5), dihydrophenanthrene (2), and quinone moieties (6 and 7), rarely found in natural products. The new compounds 3 and 5, as well as the known riccardin G, exhibited cytotoxic activity against the A549 lung cancer cell line with IC 50 values of 5.0, 5.0, and 2.5 μM, respectively.

Bis-Bibenzyls from the Liverwort Pellia endiviifolia and Their Biological Activity

“…In this paper, the isolation and the structure investigation of the chemical constituents originated from Pellia endiviifolia are presented. Cytotoxic activity of the isolated compounds was tested on three human leukemia, one human embryonal teratocarcinoma, and two human glioblastoma cell lines, and compared to previously isolated bis-bibenzyls of similar structure [17,18]. All these results show the important anticancer role of the perrottetin-like compounds on the tested cell lines.…”

“…Perrottetin E (1) was already a known constituent from this liverwort (11), whereas 10 -hydroxyperrottetin E (2) and 10,10 -dihydroxyperrottetin E (3) were known compounds isolated from Pellia epiphylla [19] but in this work, they were isolated for the first time from P. endiviifolia. For the analysis of the biological activity, additional perrottetin-type compounds (4-7) and bibenzyl lunularin (8) isolated in previous works [17,19] were added to the isolated compounds 1, 2, and 3: perrottetin F (4), 8-hydroxyperrottetin F (5), perrottetin F-6 -sulphate (6), 2,3,7-trihydroxy-4-(3 -hydroxy-1-bibenzyloxy)-phenanthrene (7), and lunularin (8) (Figure 2). First, we analyzed the cytotoxic effects of Compounds 1-8 on acute (HL-60 and U-937) and chronic (K-562) myeloid leukemia cell lines.…”

Bisaurones – enzymatic production and biological evaluation

“…Pure chalcon butein and aurone sulfuretin were isolated from the C. coggygria bark. 52 Both compounds, as well as methanol extract of the plant bark were used for the biocatalytic transformation. T. versicolor laccase (1.07 U mg -1 ) was purchased from Sigma Aldrich (St.…”

Assessment of the Biological Effects of Pellia endiviifolia and its Constituents in Vitro

“…7 Furthermore, the bis-bibenzyls of riccardin and perrottetin types isolated from the liverwort Lunularia cruciata exhibited cytotoxic activity against the A549 lung cancer cell line. 8 Also, perrottetin F and metabolites obtained by its biotransformation by Aspergillus niger showed promising antimicrobial activity and antiproliferative effects on human lung carcinoma. 9 Perrottetin E isolated from Conocephalum japonicum and Radula perrottetii exhibited cytotoxic effects against human nasopharyngeal epidermoid carcinoma (KB) cells 10,11 and induced inhibition of thrombin activation.…”