Purification, crystallization and anticancer activity evaluation of the compound alternariol methyl ether from endophytic fungiAlternaria alternata

Abstract

Aims: Medicinal plant-associated endophytic fungi are important sources of precious bioactive compounds, contributing more than 80% of the natural drugs for various ailments. The present study was aimed at evaluating the anticancer activity of the crystallized compound alternariol methyl ether (AME) against hepatocellular carcinoma (HCC) both in vitro and in vivo from an endophytic fungus residing in the medicinal plant Vitex negundo. Methods and Results: The secondary metabolites from the endophytic fungus Alternaria alternata MGTMMP031 were isolated. Purification and characterization of the compound was performed and the potential compound was identified as AME. The crystal structure of AME was unambiguously confirmed by X-ray analysis. AME has been checked for its antibacterial and anticancer properties which showed its effectiveness against various bacteria and demonstrated marked anti-proliferative activity against the human HCC cells (HUH-7) both in vitro and in vivo. Mode of actions included cell cycle arrest, reducing the level of markers enzymes of liver cancer and preventing tumour growth. Conclusions: Alternariol methyl ether acts as a potential therapeutic target against HCC. The compound was isolated and the crystal structure was obtained for the first time from the endophytic fungus A. alternata MGTMMP031. In the present study, the crystallized structure of AME was obtained by slow evaporation technique. It can be concluded that AME acts as a potential therapeutic target against HCC. Significance and Impact of the Study: Endophytic fungi residing in the medicinal plants have strong biological significance and bioactive compounds from these fungi provide better therapeutic targets against diseases.

Fungal Endophytes: A Potential Source of Antibacterial Compounds

“…A new 4-hydroxycinnamic acid derivative compound, methyl 2-{(E)-2-[4-(formyloxy) phenyl]ethenyl}-4-methyl-3-oxopentanoate (146), along with the known compounds (3R,6R)-4-methyl-6-(1-methylethyl)-3-phenylmethylperhydro-1,4-oxazine-2,5-dione (147), (3R,6R)-N-methyl-N-(1-hydroxy-2-methylpropyl)-phenylalanine (148), siccanol (149), sambutoxin (150, Figure 9) and fusaproliferin (106), were extracted from Pyronema sp. an endophyte of the Taxus mairei.…”

“…Compound 347 exhibited potential activity against B. cereus, Klebsiella pneumoniae with a MIC at 30 µM/L. The compound inhibited the growth of E. coli, Salmonella typhi, Proteus mirabilis, S. aureus and S. epidermidis at a MIC of 35 µM/L [149].…”

Coumarins as Fungal Metabolites with Potential Medicinal Properties

“…For the first time, the crystal structure of an alternariol methyl ether was obtained by a slow evaporation technique after isolation of an alternariol in the form of methyl ether from the secondary metabolites of the endophytic fungus A. alternata MGTMMP031 residing in the medicinal plant Vitex negundo [ 75 ]. This study was aimed at evaluating the anticancer activity of the crystallized compound alternariol methyl ether against hepatocellular carcinoma both in vitro and in vivo.…”

“…The assays showed its efficiency versus different bacteria and demonstrated marked anti-proliferative activity against the human hepatocellular carcinoma cells (HUH-7), both in vitro and in vivo. The mode of functionality involved cell cycle arrest, reducing the level of markers enzymes of liver cancer and preventing tumor growth [ 75 ]. The authors concluded that the alternariol methyl ether acts as a potential therapeutic target against hepatocellular carcinoma cells.…”

Synthesis of Chloro-Substituted 6<i>H</i>-Dibenzo[<i>b</i>,<i>d</i>]pyran-6-one Natural Products, Graphislactone G, and Palmariols A and B

“…A variety of natural products, which possess the 6Hdibenzo [b,d] pyran-6-one core has attracted our interest because of their unique biological activities. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18] Among them, graphislactone G (1) was isolated from Cephalosporium acremonium IFB-E007 in 2005 and known to exhibit an inhibitory activity against the SW1116 cell line. 19) In addition, palmariols A (2) and B (3) were found from Lachnum palmae in 2010, 20) and their antimicrobial, antinematodal, and acetylcholinesterase inhibitory activities were investigated.…”