Theoretical Study on the Antioxidant Activity of Natural Depsidones

Bay, Mai Van; Nam, Pham Cam; Quang, Duong Tuan; Mechler, Ádám; Hien, Nguyen Khoa; Hòa, Nguyễn Thị; Vo, Quan V.

doi:10.1021/acsomega.9b04179

Cited by 20 publications

(19 citation statements)

References 56 publications

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“…In general, the neutral molecule dominates in pH in polyprotic acid) for target molecules, while the deprotonation occurs in pH pK . pK ’s of some typical metabolites are known in the literature 28 , 73 – 76 . Thus, we discuss complexation stabilities of the metabolites mainly in physiological pH range around pH 7.4 ± 1.5 with literature information of pK ’s of the present target molecules seen in Fig.…”

Section: Calculation Resultsmentioning

confidence: 99%

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Quantum chemical calculation studies toward microscopic understanding of retention mechanism of Cs radioisotopes and other alkali metals in lichens

Suno

Machida

Dohi

et al. 2021

Sci Rep

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We evaluate stability of cesium (Cs) and other alkali-metal cation complexes of lichen metabolites in both gas and aqueous phases to discuss why lichens can retain radioactive Cs in the thalli over several years. We focus on oxalic acid, (+)-usnic acid, atranorin, lecanoric acid, and protocetraric acid, which are common metabolite substances in various lichens including, e.g., Flavoparmelia caperata and Parmotrema tinctorum retaining Cs in Fukushima, Japan. By performing quantum chemical calculations, their gas-phase complexation energies and aqueous-solution complexation free energies with alkali-metal cations are computed for their neutral and deprotonated cases. Consequently, all the molecules are found to energetically favor cation complexations and the preference order is Li$$^+>$$ + > Na$$^+>$$ + > K$$^+>$$ + > Rb$$^+>$$ + > Cs$$^+$$ + for all conditions, indicating no specific Cs selectivity but strong binding with all alkali cations. Comparing complexation stabilities among these metabolites, lecanoric and protocetraric acids seen in medullary layer are found to keep higher affinity in their neutral case, while (+)-usnic acid and atranorin in upper cortex exhibit rather strong affinity only in deprotonated cases through forming stable six atoms’ ring containing alkali cation chelated by two oxygens. These results suggest that the medullary layer can catch all alkali cations in a wide pH range around the physiological one, while the upper cortex can effectively block penetration of metal ions when the metal stress grows. Such insights highlight a physiological role of metabolites like blocking of metal-cation migrations into intracellular tissues, and explain long-term retention of alkali cations including Cs in lichens containing enough such metabolites to bind them.

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Section: Calculation Resultsmentioning

confidence: 99%

“…Aside from biochemical roles described above, lichen metabolites have been confirmed to be also widely useful in pharmaceutical applications 22 – 28 . For example, some metabolites are now known to possess several useful properties like UV-light shielding, antibiotic, anti-proliferative, anti-inflammatory, and anti-oxidant ones 29 .…”

Section: Introductionmentioning

confidence: 99%

Quantum chemical calculation studies toward microscopic understanding of retention mechanism of Cs radioisotopes and other alkali metals in lichens

Suno

Machida

Dohi

et al. 2021

Sci Rep

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“…Antioxidant Hydroxyl and superoxide anion radical scavengers in polar environments [131] Deoxystictic acid Fumarprotocetraric acid Cetraria islandica (L.) Ach.…”

Section: Computational Studiesmentioning

confidence: 99%

Lichen Depsidones with Biological Interest

et al. 2021

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Depsidones are some of the most abundant secondary metabolites produced by lichens. These compounds have aroused great pharmacological interest due to their activities as antioxidants, antimicrobial, and cytotoxic agents. Hence, this paper aims to provide up-to-date knowledge including an overview of the potential biological interest of lichen depsidones. So far, the most studied depsidones are fumarprotocetraric acid, lobaric acid, norstictic acid, physodic acid, salazinic acid, and stictic acid. Their pharmacological activities have been mainly investigated in in vitro studies and, to a lesser extent, in in vivo studies. No clinical trials have been performed yet. Depsidones are promising cytotoxic agents that act against different cell lines of animal and human origin. Moreover, these compounds have shown antimicrobial activity against both Gram-positive and Gram-negative bacteria and fungi, mainly Candida spp. Furthermore, depsidones have antioxidant properties as revealed in oxidative stress in vitro and in vivo models. Future research should be focused on further investigating the mechanism of action of depsidones and in evaluating new potential actions as well as other depsidones that have not been studied yet from a pharmacological perspective. Likewise, more in vivo studies are prerequisite, and clinical trials for the most promising depsidones are encouraged.

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“…Their variable linked patterns and different substituents lead to rich structural diversity. Naturally occurring depsides and depsidones were recently found with a wide array of remarkable bioactivities, including antimicrobial [ 8 , 9 ], α-glucosidase inhibitory [ 10 , 11 ], anti-inflammatory [ 12 , 13 ], cytotoxic [ 12 ], antioxidant [ 14 ], and anti-viral activities [ 15 ], arousing considerable interest from the communities of chemistry and pharmacology [ 6 , 16 ]. Curiously, a depsidone natural product, norstictic acid, was very recently reported as a key selective allosteric transcriptional regulator in a patient-derived model of triple-negative breast cancer [ 17 ].…”

Section: Introductionmentioning

confidence: 99%

Anti-Osteoclastogenic and Antibacterial Effects of Chlorinated Polyketides from the Beibu Gulf Coral-Derived Fungus Aspergillus unguis GXIMD 02505

Zhang

Huang

et al. 2022

Marine Drugs

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One new depsidone derivative, aspergillusidone H (3), along with seven known biosynthetically related chlorinated polyketides, were obtained from the Beibu Gulf coral-derived fungus Aspergillus unguis GXIMD 02505. Their structures were determined by comprehensive physicochemical and spectroscopic data interpretation. Notably, the X-ray crystal structure of 2 and the previously unknown absolute configuration of 8, assigned by ECD calculations, are described here for the first time. Compounds 1–5, 7 and 8 exhibited inhibition of lipopolysaccharide (LPS)-induced NF-κB in RAW 264.7 macrophages at 20 μM. In addition, the two potent inhibitors (2 and 7) dose-dependently suppressed RANKL-induced osteoclast differentiation without any evidence of cytotoxicity in bone marrow macrophages cells (BMMs). This is the first report of osteoclastogenesis inhibitory activity for the metabolites of these kinds. Besides, compounds 1, 2, 4, and 6–8 showed inhibitory activity against marine biofilm-forming bacteria, methicillin-resistant Staphylococcus aureus, Microbulbifer variabilis, Marinobacterium jannaschii, and Vibrio pelagius, with their MIC values ranging from 2 to 64 μg/mL. These findings provide a basis for further development of chlorinated polyketides as potential inhibitors of osteoclast differentiation and/or for use as anti-fouling agents.

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Theoretical Study on the Antioxidant Activity of Natural Depsidones

Cited by 20 publications

References 56 publications

Quantum chemical calculation studies toward microscopic understanding of retention mechanism of Cs radioisotopes and other alkali metals in lichens

Quantum chemical calculation studies toward microscopic understanding of retention mechanism of Cs radioisotopes and other alkali metals in lichens

Lichen Depsidones with Biological Interest

Anti-Osteoclastogenic and Antibacterial Effects of Chlorinated Polyketides from the Beibu Gulf Coral-Derived Fungus Aspergillus unguis GXIMD 02505

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