Investigations of Lichen Secondary Metabolites with Potential Anticancer Activity

Objective: Aspergillus fungus is a rich source of natural products with broad biological activities. This study was conducted to identify secondary metabolites from the rice culture of Aspergillus species isolated from Melaleuca subulata leaves and evaluated their anticancer activity. Methods: Ethyl acetate extract was fractionated on silica gel and Sephadex columns. Structures of the compounds were established using physical and chemical methods. Cytotoxic activities of the extract and pure compounds against two human cancer cell lines (Mcf-7and Hep G2) were evaluated using microculture tetrazolium assay as well as the mode of the cytotoxicity was evaluated. Molecular docking studies have been performed using the Hsp 90 enzyme as an anticancer target. Results: Methyl linoleate (1), arugosin C (2), ergosterol (3), sterigmatocystin (4), diorcinol (5), alternariol-5-O-methyl ether (6), averufin (7), averufanin (8), and alternariol (9) were identified from ethyl acetate extract. All tested compounds exhibit week activity against MCF-7 and Hep G2 cell lines but a mixture of compounds 7 and 8 is considered to be more active towards both MCF-7 and Hep G 2 in comparison to other compounds. Compound 4 exhibits moderate activity against Hep G2 only as well as the ethyl acetate extract exerts moderate activity against MCF-7 cell line Moreover, compound 4 and a mixture of 7 and 8 caused a decrease in the number of Hep G2 cancer cells due to apoptotic and necrotic processes. Most active anticancer candidates 7 and 8 showed binding to the active site similar to geldanamycin reference ligand. Conclusion: Secondary metabolites identified from Aspergillus sp. and their anticancer activity were evaluated. Molecular docking suggested active candidates as Hsp 90 inhibitors.

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Update on Monoterpenes from Red Macroalgae: Isolation, Analysis, and Bioactivity

Marine Drugs ◽

10.3390/md17090537 ◽

2019 ◽

Vol 17 (9) ◽

pp. 537

Author(s):

Ana-Marija Cikoš ◽

Mladenka Jurin ◽

Rozelindra Čož-Rakovac ◽

Stela Jokić ◽

Igor Jerković

Keyword(s):

Biological Activity ◽

Secondary Metabolites ◽

Anticancer Activity ◽

Structure Elucidation ◽

Present Review ◽

Red Macroalgae ◽

Methylerythritol Phosphate ◽

Halogenated Monoterpenes ◽

Wide Range ◽

Halogen Content

Macroalgae produce a wide range of monoterpenes as secondary metabolites of mevalonate (MVA) and/or methylerythritol phosphate (MEP) pathway (often including haloperoxidase action). Great biodiversity of macroalgal monoterpenes was reported including acyclic, monocyclic, and bicyclic structures. Halogenated monoterpenes exhibited significant biological activity (e.g., anticancer, antiplasmodial, and insecticidal) that is influenced by the number of present halogens (higher halogen content is preferable, especially bromine) and their position within the monoterpene skeleton. In distinction from the existing reviews, the present review provides novelty with respect to: (a) exclusively monoterpenes from red macroalgae are targeted; (b) biosynthesis, isolation, and analysis, as well as bioactivity of monoterpenes are represented; (c) the methods of their isolation, analysis, and structure elucidation are summarized; (d) the bioactivity of macroalgal monoterpenes is systematically presented with emphasis on anticancer activity; (e) the literature references were updated.

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Fungal metabolites with anticancer activity

Natural Product Reports ◽

10.1039/c3np70078j ◽

2014 ◽

Vol 31 (5) ◽

pp. 617-627 ◽

Cited By ~ 89

Author(s):

Antonio Evidente ◽

Alexander Kornienko ◽

Alessio Cimmino ◽

Anna Andolfi ◽

Florence Lefranc ◽

...

Keyword(s):

Secondary Metabolites ◽

Anticancer Activity ◽

Fungal Metabolites ◽

Biochemical Studies ◽

Fungal Secondary Metabolites

The review discusses the reported sources, structures and biochemical studies aimed at the exploitation of the anticancer potential associated with fungal secondary metabolites.

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2-(4-Chlorophenyl)-3-hydroxy-4H-chromen-4-one

IUCrData ◽

10.1107/s2414314617009968 ◽

2017 ◽

Vol 2 (7) ◽

Cited By ~ 2

Author(s):

Sarah Zingales ◽

Clifford Padgett

Keyword(s):

Crystal Structure ◽

Secondary Metabolites ◽

Transition Metals ◽

Anticancer Activity ◽

Biological Activities

Flavones are a subclass of flavonoids, secondary metabolites of plants which contain the 2-phenylbenzopyran pharmacophore. They are of interest as they display a wide variety of biological activities, such as anticancer and antioxidant. Recently, there has been an interest in coordinating flavones to various transition metals for anticancer activity. Our work in this area led to the synthesis and crystallization of flavones as intermediates. Herein, we report the first crystal structure of 2-(4-chlorophenyl)-3-hydroxy-4H-chromen-4-one, C15H9ClO3, a well studied compound.

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Antioxidant and Anticancer Properties of Leaf and Fruit Extracts of the Wild Raspberry (Rubus idaeus L.)

Notulae Botanicae Horti Agrobotanici Cluj-Napoca ◽

10.15835/nbha47111274 ◽

2018 ◽

Vol 47 (2) ◽

pp. 359-367 ◽

Cited By ~ 4

Author(s):

Bojana VELJKOVIC ◽

Natasa DJORDJEVIC ◽

Zana DOLICANIN ◽

Braho LICINA ◽

Marina TOPUZOVIC ◽

...

Keyword(s):

Antioxidant Activity ◽

Secondary Metabolites ◽

Anticancer Activity ◽

Cancer Cell Line ◽

Rubus Idaeus ◽

Colorectal Cancer Cell Line ◽

Leaf Extracts ◽

Fruit Extracts ◽

Anticancer Properties ◽

Human Colorectal Cancer Cell

In this study the leaves and fruits of wild raspberry (Rubus idaeus L.) populations from the central Balkan region were examined to determine the level of secondary metabolites and related antioxidant activity, as well as biological activity, upon existing ethnobotanical evidence, primarily linked to gastrointestinal disorders. The values obtained for total phenols ranged from 59.68 to 96.83 mg GA g-1 and 24.29 to 38.71 mg GA g-1 in leaf and fruit extracts, respectively. The highest values of tannins and anthocyanins were determined for leaf extracts from a population of east Serbia at a level of 1.27 mg mL-1 and 9.00 mg mL-1. Antioxidant activity was evaluated by measuring the scavenging capacity of the extracts on DPPH. Higher antioxidant activity was detected in the leaf extracts than in the fruit extracts. Leaf and fruit extract were the most effective against Escherichia coli (ATCC 8739). Anticancer activity was studied on a human colorectal cancer cell line HCT-116. Leaf extracts exhibited anticancer activity with IC50/24 h 162.38 μg mL-1 and IC50/48 h 95.69 μg mL-1. Wild raspberry leaf and fruit extracts contain numerous secondary metabolites providing marked antioxidant, antimicrobial and anticancer activity.

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