8-Hydroxydihydrochelerythrine and 8-Hydroxydihydrosanguinarine with a Potent Acetylcholinesterase Inhibitory Activity from Chelidonium majus L.

Cho, Kyung-Mi; Yoo, Ick Dong; Kim, Won‐Gon

doi:10.1248/bpb.29.2317

Cited by 64 publications

(49 citation statements)

References 18 publications

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“…By comparison of the activity of 1 (R = H) with that of the other compounds (2-24) on each the fungus (Table 1), it was clearly seen that the introduction of various substituents to N-aromatic ring had significant effects on the activity, indicating that the N-phenyl group was a high sensitive structural moiety for the activity. The general trend was that electron-withdrawing substituents like halogen atoms (2-12), trifluoromethyl groups (-CF 3 ) (13)(14)(15) and nitro groups (m-and p-NO 2 ) (17, 18), especially halogen atoms, remarkably enhanced the activity. On the contrary, the presence of electron-donating groups like -CH 3 (19)(20)(21), o-OH (22), and p-OCH 3 (24) led to a decrease of the activity in most cases (Figure 2).…”

Section: Structure-activity Relationshipmentioning

confidence: 99%

“…Among them, sanguinarine (SA) and chelerythrine (CH) (Figure 1) are the most common. QBAs had been proven to have low toxicity to mammals [7][8][9] and extensive pharmacological activities such as antitumor [10], antimicrobial [11,12], anti-inflammatory [7], anti-HIV [13], anti-angiogenesis [14], anti-acetylcholinesterase [15] and antiparasitic actions against Trichodina sp. [16], Dactylogyrus intermedius [17], malaria [18] and Psoroptes cuniculi [6].…”

Section: Introductionmentioning

confidence: 99%

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2-(Substituted phenyl)-3,4-dihydroisoquinolin-2-iums as Novel Antifungal Lead Compounds: Biological Evaluation and Structure-Activity Relationships

et al. 2013

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Abstract:The title compounds are a class of structurally simple analogues of quaternary benzo [c]phenanthridine alkaloids (QBAs). In order to develop novel QBA-like antifungal drugs, in this study, 24 of the title compounds with various substituents on the N-phenyl ring were evaluated for bioactivity against seven phytopathogenic fungi using the mycelial growth rate method and their SAR discussed. Almost all the compounds showed definite activities in vitro against each of the test fungi at 50 μg/mL and a broad antifungal spectrum. In most cases, the mono-halogenated compounds 2-12 exhibited excellent activities superior to the QBAs sanguinarine and chelerythrine. Compound 8 possessed the strongest activities on each of the fungi with EC 50 values of 8.88-19.88 µg/mL and a significant concentration-dependent relationship. The SAR is as follows: the N-phenyl group is a high sensitive structural moiety for the activity and the characteristics and position of substituents intensively influence the activity. Generally, electron-withdrawing substituents remarkably enhance the activity while electron-donating substituents cause a decrease of the activity. In most cases, ortha-and para-halogenated isomers were more active than the corresponding m-halogenated isomers. Thus, the title compounds emerged as promising lead compounds for the development of novel biomimetic antifungal

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Section: Structure-activity Relationshipmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

2-(Substituted phenyl)-3,4-dihydroisoquinolin-2-iums as Novel Antifungal Lead Compounds: Biological Evaluation and Structure-Activity Relationships

et al. 2013

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“…The use of AChE inhibitors (which increases the amount of acetylcholine present in the synapses between cholinergic neurons) has become one among the various therapeutic strategies to enhance the cholinergic functions in the brain (Cho et al, 2006). Table 1 demonstrates the AChE inhibitory activity of various concentrations (20-100 mg/mL) of solvent extracts of S. wightii.…”

Section: Evaluation Of Cholinesterase Inhibitory Activity Of S Wightiimentioning

confidence: 99%

Antioxidant and anti-cholinesterase activity ofSargassum wightii

Syad

Shunmugiah

Kasi

2013

Pharmaceutical Biology

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Context: Sargassum has been used in traditional Chinese medicine since the eighth century AD to treat goiter. Sargassum wightii Greville (Sargassaceae) is a major source of alginic acid used widely in food and drug industries. Objective: To evaluate the anti-Alzheimer potential of S. wightii through evaluation of antioxidant and cholinesterase inhibitory activities. Materials and methods: Successive extraction was done using solvents of varying polarity. Solvent extracts (100-500 mg/mL) were employed for all the antioxidant assays. Free radical scavenging activity was evaluated by 2,2-diphenyl-1-picrylhydrazyl, OH. , H 2 O 2 radical scavenging assay. The reducing power of the seaweed was evaluated by ferric reducing antioxidant power and reducing power assay. Cholinesterase (ChE) inhibitory activity was evaluated and the Km, Vmax and Ki were calculated. Further, compound characterization was done by GC-MS analysis. Results: The non-polar extracts were found to possess significant antioxidant activity. At 100 mg/mL, petroleum ether, hexane, benzene and dichloromethane extracts showed significant ChE inhibitory activity with IC 50 values of 19.33 AE 0.56, 46.81 AE 1.62, 27.24 AE 0.90, 50.56 AE 0.90 mg/mL, respectively, for AChE, and 17.91 AE 0.65, 32.75 AE 1.00, 12.98 AE 0.31, 36.16 AE 0.64 mg/mL, respectively, for BuChE. GC-MS reveals that 1,2-benzenedicarboxylic acid, diisooctyl ester is the major compound present in dichloromethane extract of S. wightii. The mode of inhibition exhibited by dichloromethane extract against the cholinesterases was found to be competitive type. Discussion and conclusion: The presence of high amount of terpenoids could be the possible reason for its potential antioxidant and ChE inhibitory activity.

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“…1), which is a relatively small subclass of isoquinoline alkaloids and mainly presents in the families of the Fumariaceae, Papaveraceae and Rutaceae families. 9) In the past decades, QBAs have given rise to a lot of attention because of their biological activities including antitumor, 10) antimicrobial, 11,12) anti-inflammatory, 13) anti-human immunodeficiency virus (HIV), 14) anti-angiogenesis 15) and anti-acetylcholinesterase, 16) and antiparasitic actions against Trichodina sp., 17) Dactylogyrus intermedius 18) and malaria. 19) Our recent research found that 6-alkoxy dihydrosanguinarines ( Fig.…”

mentioning

confidence: 99%

Synthesis of 2-Aryl-3,4-dihydroisoquinolin-2-ium Bromides and Their <i>in Vitro</i> Acaricidal Activity against <i>Psoroptes cuniculi</i>

Yang

Pan

et al. 2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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By employing sanguinarine, a natural active quaternary isoquinoline alkaloid, as a model molecule, a series of structurally simple quaternary 2-aryl-3,4-dihydroisoquinolin-2-ium compounds were designed and synthesized and evaluated for in vitro acaricidal activity against P. cuniculi. A new approach towards the title compounds was developed with isochroman as starting material. The results showed that 22 of 24 tested compounds displayed the activity in varying degrees at 0.4 mg/mL. Fourteen compounds were significantly more effective than ivermectin, a standard acaricide, and 6-methoxy dihydrosanguinarine, a derivative of sanguinarine (p<0.05). And their comprehensive relative activity was 1.4 to 16.5 times than that of ivermectin and 1.5 to 18.8 times than that of 6-methoxy dihydrosanguinarine. The structure-activity relationship indicated that the introduction of a substituent to N-benzene ring, especially halogen atom and trifluoromethyl group, led to great improvement of the activity. The position of fluorine atom, methyl group and hydroxyl group made very significant effects on the activity. It was concluded that 2-aryl-3,4-dihydroisoquinolin-2-iums are very promising candidates for the development of new isoquinoline acaricidal agents.Key words acaricidal activity; Psoroptes cuniculi; 2-aryl-3,4-dihydroisoquinolin-2-ium; 6-methoxy dihydrosanguinarine; sanguinarine; structure-activity relationship Acariasis is a chronic skin disease caused by mites, an ectoparasite, and widely occurs in animals and human. Psoroptes cuniculi is one of animal mites and mainly infects rabbits, goats, horses and sheep.1) It causes intense pruritus of animals with the formation of crusts and scabs and reduction of weight gain, or even death of animals.2,3) Therefore, this mite species causes serious economic losses for animal industry.Therapy and control of both human scabies and animal mange are based mainly on the use of effective drugs and chemicals. At present, the use of drugs to control these parasitic arthropods presents several problems including drugresistance 4,5) and environmental damage. 6,7) Ivermectin (Fig. 1), a clinically used acaricide, is increasingly being used to treat human scabies but often treatment failures, recrudescence and reinfection can occur.8) Concern over toxicity of many acaricides limits their use and reduces the number of Regular Article * To whom correspondence should be addressed. e-mail: zhoulechem@yahoo.com.cn; miaofangmf@163.com The authors declare no conflict of interest. # These authors contributed equally to this work.

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8-Hydroxydihydrochelerythrine and 8-Hydroxydihydrosanguinarine with a Potent Acetylcholinesterase Inhibitory Activity from Chelidonium majus L.

Cited by 64 publications

References 18 publications

2-(Substituted phenyl)-3,4-dihydroisoquinolin-2-iums as Novel Antifungal Lead Compounds: Biological Evaluation and Structure-Activity Relationships

2-(Substituted phenyl)-3,4-dihydroisoquinolin-2-iums as Novel Antifungal Lead Compounds: Biological Evaluation and Structure-Activity Relationships

Antioxidant and anti-cholinesterase activity ofSargassum wightii

Synthesis of 2-Aryl-3,4-dihydroisoquinolin-2-ium Bromides and Their <i>in Vitro</i> Acaricidal Activity against <i>Psoroptes cuniculi</i>

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