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

Ivana Ivković,Marija Mojsin,Petar D Marin,Milena Stevanović,Danka Bukvički,Milan Veljić,Miroslav Novaković

doi:10.3390/plants10061063

Abstract

Based on previous investigations where bis-bibenzyls isolated from liverworts showed various biological activities (cytotoxic, antimicrobial, and antiviral), we investigated their cytotoxic activity in several human cancer cell lines. From the methylene-chloride/methanol extract of the liverwort Pellia endiviifolia, three bis-bibenzyls of the perrottetin type were isolated, namely perrottetin E, 10′-hydroxyperrottetin E, and 10,10′-dihydroxyperrottetin E. The last two were found for the first time in this species. Their structures were resolved using 1D and 2D NMR, as well as by comparison with data in the literature. Cytotoxic activity of the isolated compounds was tested on three human leukemia cell lines, HL-60 (acute promyelocytic leukemia cells), U-937 (acute monocytic leukemia cells), and K-562 (human chronic myelogenous leukemia cells), as well as on human embryonal teratocarcinoma cell line (NT2/D1) and human glioblastoma cell lines A-172 and U-251, and compared to the previously isolated bis-bibenzyls (perrottetins) of similar structure. The isolated compounds exhibited modest activity against leukemia cells and significant activity against NT2/D1 and A-172. Overall, the most active cytotoxic compounds in this investigation were perrottetin E (1), isolated in this work from Pellia endiviifolia, and perrottetin F phenanthrene derivative (7), previously isolated from Lunularia cruciata and added for a comparison of their cytotoxic activity.

Highlights

Introduction published maps and institutional affilBryophytes—small, non-vascular plants—are usually divided into three separate divisions: Marchantiophyta, Bryophyta, and Anthocerotophyta [1]
(3) were known compounds isolated from Pellia epiphylla [19] but in this work, they were isolated for the first time from P. endiviifolia
We analyzed the cytotoxic effects of Compounds 1–8 on acute (HL-60 and U937) and chronic (K-562) myeloid leukemia cell lines

Summary

Introduction

Bryophytes—small, non-vascular plants—are usually divided into three separate divisions: Marchantiophyta (liverworts), Bryophyta (genuine mosses), and Anthocerotophyta (hornworts) [1]. Liverworts are classified into thalloid and leafy species. In comparison with the other two divisions, liverworts possess oil bodies in their cells that carry various secondary metabolites—mostly aromatic compounds, acetogenins, and terpenoids [2,3]. Different types of acyclic and cyclic bisbibenzyls, along with their derivatives, are the most characteristic compounds isolated from the liverworts. Phenolic bis-bibenzyls, with four aromatic rings, derive from the bibenzyl lunularin or its precursor lunularic acid [4]. Secondary metabolites produced by liverworts show interesting biological activities, such as cytotoxic, antibacterial, antifungal, iations

Results

Discussion

Conclusion