Calycosin and 8-O-methylretusin isolated from Maackia amurensis as potent and selective reversible inhibitors of human monoamine oxidase-B

Oh, Jong Min; Jang, Hyun‐Jae; Kim, Won Jun; Kang, Myung-Gyun; Baek, Seung Cheol; Lee, Jae Pil; Park, Daeui; Oh, Sei‐Ryang; Kim, Hoon

doi:10.1016/j.ijbiomac.2020.02.144

Cited by 42 publications

(34 citation statements)

References 57 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…( Leguminosae )) is common in Korea, Japan, Northeastern China and Eastern Russia. The trunk bark of this tree has traditionally been used for the treatment of cancer, cholecystitis, arthritis and hyperthyroidism, as well as for hepatoprotection [ 102 , 103 ]. The chemical composition of M. amurensis has been determined with identified isoflavonoids, polyphenol and isoflavone glycosides, prenylated flavonoids [ 104 , 105 , 106 ].…”

Section: Resultsmentioning

confidence: 99%

Medicinal Plants to Strengthen Immunity during a Pandemic

et al. 2020

View full text Add to dashboard Cite

The development of new effective anti-coronavirus drugs and therapies is important, but it requires significant human, financial and, most importantly, time expenditures. The current pandemic is neither the first nor the last. Humanity has already accumulated considerable survival experience. We cannot do without prevention and epidemiological protection measures. This study reviews medicinal plants that grow in Northeast Asia and whose antioxidant, antiviral, anti-inflammatory and immunomodulatory characteristics are already known, also in the framework of the prevention and treatment of pneumonia of various etiologies. The need for a comprehensive approach to maintaining immunodefences, including functional foods and positive emotions, is emphasized. In the period of pandemics, it is important to research various areas that allow to us accumulate a critical mass of information and cope with the next global disease.

show abstract

Section: Resultsmentioning

confidence: 99%

Medicinal Plants to Strengthen Immunity during a Pandemic

et al. 2020

View full text Add to dashboard Cite

show abstract

“…In our previous studies, we isolated the MAO-A inhibitors, hispidol from Glycin max Merrill 39 and decursin from Angelica gigas Nakai 40 , and the MAO-B inhibitors, maackiain from Sophora flavescens 21 and calycosin from Maackia amurensis 11 . In the present study, of the 276 herbal extracts examined, the methanol extract of the stems of C. cuspidata was selected as a potential source of AChE inhibitors and five compounds were subsequently isolated using a bioassay-guided method and identified.…”

Section: Discussionmentioning

confidence: 99%

“…During our on-going efforts to identify potent natural inhibitors of MAO-A, MAO-B, and AChE in a herbal extract library, we found that rhamnocitrin isolated from the leaves of Prunus padus var. seoulensis , potently and selectively inhibits human MAO-A 10 , and that calycosin isolated from Maackia amurensis potently and selectively inhibits human MAO-B 11 . In this study, we screened Castanopsis cuspidata var.…”

Section: Introductionmentioning

confidence: 96%

Acetylcholinesterase and monoamine oxidase-B inhibitory activities by ellagic acid derivatives isolated from Castanopsis cuspidata var. sieboldii

Jang

Kang

et al. 2021

Sci Rep

Self Cite

View full text Add to dashboard Cite

Among 276 herbal extracts, a methanol extract of Castanopsis cuspidata var. sieboldii stems was selected as an experimental source for novel acetylcholinesterase (AChE) inhibitors. Five compounds were isolated from the extract by activity-guided screening, and their inhibitory activities against butyrylcholinesterase (BChE), monoamine oxidases (MAOs), and β-site amyloid precursor protein cleaving enzyme 1 (BACE-1) were also evaluated. Of these compounds, 4′-O-(α-l-rhamnopyranosyl)-3,3′,4-tri-O-methylellagic acid (3) and 3,3′,4-tri-O-methylellagic acid (4) effectively inhibited AChE with IC50 values of 10.1 and 10.7 µM, respectively. Ellagic acid (5) inhibited AChE (IC50 = 41.7 µM) less than 3 and 4. In addition, 3 effectively inhibited MAO-B (IC50 = 7.27 µM) followed by 5 (IC50 = 9.21 µM). All five compounds weakly inhibited BChE and BACE-1. Compounds 3, 4, and 5 reversibly and competitively inhibited AChE, and were slightly or non-toxic to MDCK cells. The binding energies of 3 and 4 (− 8.5 and − 9.2 kcal/mol, respectively) for AChE were greater than that of 5 (− 8.3 kcal/mol), and 3 and 4 formed a hydrogen bond with Tyr124 in AChE. These results suggest 3 is a dual-targeting inhibitor of AChE and MAO-B, and that these compounds should be viewed as potential therapeutics for the treatment of Alzheimer’s disease.

show abstract

“…For contrast, MAO-B was preincubated with lazabemide (a reference reversible MAO-B inhibitor) or pargyline (a reference irreversible MAO-B inhibitor) at 0.20 and 0.30 µM. Reversibility patterns were analyzed by comparing the activities of dialyzed (A D ) and undialyzed (A U ) samples [58].…”

Section: Inhibitor Reversibility Analysismentioning

confidence: 99%

Trimethoxylated Halogenated Chalcones as Dual Inhibitors of MAO-B and BACE-1 for the Treatment of Neurodegenerative Disorders

Vishal

Khames

et al. 2021

Pharmaceutics

Self Cite

View full text Add to dashboard Cite

Six halogenated trimethoxy chalcone derivatives (CH1–CH6) were synthesized and spectrally characterized. The compounds were further evaluated for their inhibitory potential against monoamine oxidases (MAOs) and β-secretase (BACE-1). Six compounds inhibited MAO-B more effectively than MAO-A, and the 2′,3′,4′-methoxy moiety in CH4–CH6 was more effective for MAO-B inhibition than the 2′,4′,6′-methoxy moiety in CH1–CH3. Compound CH5 most potently inhibited MAO-B, with an IC50 value of 0.46 µM, followed by CH4 (IC50 = 0.84 µM). In 2′,3′,4′-methoxy derivatives (CH4-CH6), the order of inhibition was –Br in CH5 > -Cl in CH4 > -F in CH6 at the para-position in ring B of chalcone. CH4 and CH5 were selective for MAO-B, with selectivity index (SI) values of 15.1 and 31.3, respectively, over MAO-A. CH4 and CH5 moderately inhibited BACE-1 with IC50 values of 13.6 and 19.8 µM, respectively. When CH4 and CH5 were assessed for their cell viability studies on the normal African Green Monkey kidney cell line (VERO) using MTT assays, it was noted that both compounds were found to be safe, and only a slightly toxic effect was observed in concentrations above 200 µg/mL. CH4 and CH5 decreased reactive oxygen species (ROS) levels of VERO cells treated with H2O2, indicating both compounds retained protective effects on the cells by antioxidant activities. All compounds showed high blood brain barrier permeabilities analyzed by a parallel artificial membrane permeability assay (PAMPA). Molecular docking and ADME prediction of the lead compounds provided more insights into the rationale behind the binding and the CNS drug likeness. From non-test mutagenicity and cardiotoxicity studies, CH4 and CH5 were non-mutagenic and non-/weak-cardiotoxic. These results suggest that CH4 and CH5 could be considered candidates for the cure of neurological dysfunctions.

show abstract

Calycosin and 8-O-methylretusin isolated from Maackia amurensis as potent and selective reversible inhibitors of human monoamine oxidase-B

Cited by 42 publications

References 57 publications

Medicinal Plants to Strengthen Immunity during a Pandemic

Medicinal Plants to Strengthen Immunity during a Pandemic

Acetylcholinesterase and monoamine oxidase-B inhibitory activities by ellagic acid derivatives isolated from Castanopsis cuspidata var. sieboldii

Trimethoxylated Halogenated Chalcones as Dual Inhibitors of MAO-B and BACE-1 for the Treatment of Neurodegenerative Disorders

Contact Info

Product

Resources

About