Lichenochemicals: extraction, purification, characterization, and application as potential anticancer agents

Mohammadi, Mahshid; Zambare, Vasudeo; Malek, Ladislav; Gottardo, Christine; Suntres, Zacharias E.; Christopher, Lew P.

doi:10.1080/17460441.2020.1730325

Cited by 10 publications

(6 citation statements)

References 138 publications

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“…It has been reported that most of the lichen phenolics isolated from Parmelia caperata, Cladonia convoluta, C. rangiformis, Platisma glauca, and Ramalina cuspidata exhibited strong antioxidant activities and anticancer activities [47]. Lichen-derived compounds have been extensively discussed in previous reviews [48,49], and they provide in-depth information on their bio-therapeutic potential.…”

Section: Lichenochemical Analysismentioning

confidence: 99%

Isolation, Characterization, and Breast Cancer Cytotoxic Activity of Gyrophoric Acid from the Lichen Umbilicaria muhlenbergii

et al. 2022

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Lichens produce a large variety of secondary metabolites with diverse bioactivities, chemical structures, and physicochemical properties. For this reason, there is a growing interest in the use of lichen-derived bioactive molecules for drug discovery and development. Here, we report on the isolation, identification, and cytotoxic evaluation of gyrophoric acid (GA) from the lichen Umbilicaria muhlenbergii, a largely unexplored and scantly described lichen species. A simple purification protocol was developed for the fractionation of lichen crude extracts with silica gel column chromatography using solvents with changing polarity. GA was identified in one of the fractions with Fourier transform infrared spectroscopy (FTIR), ion trap mass spectrometry (MS), and nuclear magnetic resonance spectroscopy (1H-NMR and 13C-NMR). The FTIR spectra demonstrated the presence of aromatic and ester functional groups C=C, C-H, and C=O bonds, with the most remarkable signals recorded at 1400 cm−1 for the aromatic region, at 1400 cm−1 for the CH3 groups, and at 1650 cm−1 for the carbonyl groups in GA. The MS spectra showed a molecular ion [M-1]− at (m/z) 467 with a molecular weight of 468.4 and the molecular formula C24H20O10. that correspond to GA. The 1H-NMR and 13C-NMR spectra verified the chemical shifts that are typical for GA. GA reduced the cell viability of breast cancer cells from the MCF-7 cell line by 98%, which is indicative of the strong cytotoxic properties of GA and its significant potential to serve as a potent anticancer drug.

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Section: Lichenochemical Analysismentioning

confidence: 99%

Isolation, Characterization, and Breast Cancer Cytotoxic Activity of Gyrophoric Acid from the Lichen Umbilicaria muhlenbergii

et al. 2022

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“…There has been an increasing interest in studying the biological activities of various lichenochemicals in recent years. These chemicals have a broad range of biological activities, including anti-inflammatory ( Joshi et al., 2019 ; Lee et al., 2020 ), anticancer ( Cimmino et al., 2019 ; Mohammadi et al., 2020 ; Solárová et al., 2020 ), antiviral ( Luzina and Salakhutdinov, 2018 ; Hassan et al., 2019 ), antimicrobial ( Basile et al., 2015 ; Nishanth et al., 2015 ; Varol, 2018 ), expectorant ( De Barros Alves et al., 2014 ), and antioxidant ( Khadhri et al., 2019 ; Prokopiev and Filippova, 2019 ; Sahin et al., 2019 ). Among the therapeutic compounds in lichens are tridepsides, mainly found in the family Umbilicariaceae ( Posner et al., 1992 ; Narui et al., 1996 ; Narui et al., 1998 ).…”

Section: Introductionmentioning

confidence: 99%

“…In any case, since several other biological activities, including anticancer, antimicrobial, antioxidant, and anti-diabetic, have been attributed to GA or compounds of the same class ( Ranković and Kosanić, 2015 ), these compounds have attracted increased attention. Furthermore, tridepsides are a relatively understudied group of lichenochemicals that may lead us to discover new, promising bioactive compounds with therapeutic potential ( Ranković, 2019 ; Goga et al., 2020 ; Mohammadi et al., 2020 ). Recently, some non-lichenic tridepsides with interesting pharmacological activities have also been reported, particularly from cultivable fungal endophytes ( Rivera-Chávez et al., 2013 ; De Medeiros et al., 2015 ), which could be of considerable importance from a biotechnological point of view.…”

Section: Introductionmentioning

confidence: 99%

Tridepsides as potential bioactives: a review on their chemistry and the global distribution of their lichenic and non-lichenic natural sources

Norouzi

Sohrabi

Yousefi

et al. 2023

Front. Fungal Biol.

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Tridepsides, as fully oxidized polyketides, have been known to exist in lichens for more than a century. Recent studies have showed that these possible defensive lichenochemicals possess various biological activities. Also, a candidate biosynthetic gene cluster was recently reported for gyrophoric acid (GA), an important tridepside. The present study focused on biosynthesis, natural sources, biological activities, and bioanalytical methods of tridepside molecules. Our survey shows that, so far, lichenic tridepsides have been reported from 37 families, 111 genera, and 526 species of lichen. Because many of their species contain tridepsides, the families Parmeliaceae, Lobariaceae, and Peltigeraceae can be considered critical lichenic sources of tridepsides. Furthermore, several species of Hypotrachyna in Parmeliaceae family showed lichenic tridepsides, suggesting that this genus is a viable source of tridepsides. This research also explored tridepsides from non-lichenic sources, such as non-lichenized fungi, lichenicolous fungi, endophytes, parasites, and liverworts, which offer substantial potential as biotechnological sources to produce tridepsides, which are produced in small amounts in lichen thalli. Two lichenic tridepsides have also been detected in non-lichenic sources: GA and tenuiorin (TE). Additionally, no significant correlation was found between tridepside biosynthesis and geographical distribution patterns for several potentially tridepside-producing lichens. We further showed that GA is the most studied tridepside with various reported biological activities, including anticancer, wound healing, photoprotection, anti-aging, antioxidant, cardiovascular effect, DNA interaction, anti-diabetes, anti-Alzheimer’s, anti-bacterial, and antifungal. Last but not least, this study provides an overview of some bioanalytical methods used to analyze tridepsides over the past few years.

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“…In the plant world, lichens are unique symbionts between fungi and algae, distinguished by specific secondary metabolites [ 21 , 22 , 23 , 24 ] with phenolic structures. They are implied in defense against ultraviolet radiation or various pathogens’ aggression, thus assuring the lichen’s survival in difficult environmental conditions.…”

Section: Introductionmentioning

confidence: 99%

ROS-Induced DNA-Damage and Autophagy in Oral Squamous Cell Carcinoma by Usnea barbata Oil Extract—An In Vitro Study

Popovici

Musuc

Matei

et al. 2022

IJMS

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Oxidative stress is associated with aging, cancers, and numerous metabolic and chronic disorders, and phenolic compounds are well known for their health-promoting role due to their free-radical scavenging activity. These phytochemicals could also exhibit pro-oxidant effects. Due to its bioactive phenolic secondary metabolites, Usnea barbata (L.) Weber ex. F.H. Wigg (U. barbata) displays anticancer and antioxidant activities and has been used as a phytomedicine for thousands of years. The present work aims to analyze the properties of U. barbata extract in canola oil (UBO). The UBO cytotoxicity on oral squamous cell carcinoma (OSCC) CLS-354 cell line and blood cell cultures was explored through complex flow cytometry analyses regarding apoptosis, reactive oxygen species (ROS) levels, the enzymatic activity of caspase 3/7, cell cycle, nuclear shrinkage (NS), autophagy (A), and synthesis of deoxyribonucleic acid (DNA). All these studies were concomitantly performed on canola oil (CNO) to evidence the interaction of lichen metabolites with the constituents of this green solvent used for extraction. The obtained data evidenced that UBO inhibited CLS-354 oral cancer cell proliferation through ROS generation (316.67 × 104), determining higher levels of nuclear shrinkage (40.12%), cell cycle arrest in G0/G1 (92.51%; G0 is the differentiation phase, while during G1 phase occurs preparation for cell division), DNA fragmentation (2.97%), and autophagy (62.98%) than in blood cells. At a substantially higher ROS level in blood cells (5250.00 × 104), the processes that lead to cell death—NS (30.05%), cell cycle arrest in G0/G1 (86.30%), DNA fragmentation (0.72%), and autophagy (39.37%)—are considerably lower than in CLS-354 oral cancer cells. Our work reveals the ROS-mediated anticancer potential of UBO through DNA damage and autophagy. Moreover, the present study suggests that UBO pharmacological potential could result from the synergism between lichen secondary metabolites and canola oil phytoconstituents.

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Lichenochemicals: extraction, purification, characterization, and application as potential anticancer agents

Cited by 10 publications

References 138 publications

Isolation, Characterization, and Breast Cancer Cytotoxic Activity of Gyrophoric Acid from the Lichen Umbilicaria muhlenbergii

Isolation, Characterization, and Breast Cancer Cytotoxic Activity of Gyrophoric Acid from the Lichen Umbilicaria muhlenbergii

Tridepsides as potential bioactives: a review on their chemistry and the global distribution of their lichenic and non-lichenic natural sources

ROS-Induced DNA-Damage and Autophagy in Oral Squamous Cell Carcinoma by Usnea barbata Oil Extract—An In Vitro Study

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