Cholinesterase inhibitory activity of isoquinoline alkaloids from three Cryptocarya species (Lauraceae)

Othman, Wan Nurul Nazneem Wan; Liew, Sook Yee; Khaw, Kooi Yeong; Murugaiyah, Vikneswaran; Litaudon, Marc; Awang, Khalijah

doi:10.1016/j.bmc.2016.07.043

Cited by 49 publications

(47 citation statements)

References 26 publications

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“…Epidemiological evidence suggests that higher consumption of flavonoids is associated with lower incidence of AD. 29 Similarly, S. argel contains multipotent components that might be useful in the treatment of AD. Values (mean ± S.D.)…”

Section: Resultsmentioning

confidence: 99%

Chemical Constituents from Solenostemma argel and their Cholinesterase Inhibitory Activity

et al. 2019

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− Alzheimer's disease is a chronic neurodegenerative disorder with no curative treatment. The commercially available drugs, which target acetylcholinesterase, are not satisfactory. The aim of this study was to investigate the cholinesterase inhibitory activity of Solenostemma argel aerial part. Eight compounds were isolated and identified by NMR: kaempferol-3-O-glucopyranoside (1), kaempferol (2), kaempferol-3-glucopyranosyl(1→6)rhamnopyranose (3) p-hydroxybenzoic acid (4), dehydrovomifoliol (5), 14,15-dihydroxypregn-4-ene-3,20-dione (6), 14,15-dihydroxy-pregn-4-ene-3,20-dione-15β-D-glucopyranoside (7) and solargin I (8). Two of them (compounds 2 and 3) could inhibit over 50 % of butyrylcholinesterase activity at 100 µM. Compound (2) displayed the highest inhibitory effect against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) with a slight selectivity towards the latter. Molecular docking studies supported the in vitro results and revealed that (2) had made several hydrogen and π-π stacking interactions which could explain the compound potency to inhibit AChE and BChE.

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Section: Resultsmentioning

confidence: 99%

Chemical Constituents from Solenostemma argel and their Cholinesterase Inhibitory Activity

et al. 2019

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“…32 Akihisa et al 33 isolated noroxyhydrastinine Corydalis tomentella [28] 402 Oleracein E Portulaca oleracea [31] 403 Pipermullesine B Piper mullesua [108] 404 Pipermullesine C Piper mullesua [108] 405 Delavatine A Incarvillea delavayi [109] 406 Neotatarine Acorus calamus [110] Cryptocarya griffithiana, and Dehaasia longipedicellata, over the past 5 years. [34][35][36][37][38][39] (+)-N-Methylisococlaurine (24) also was found in Cryptocarya species and (−)-N-methylcoclaurine (25) was identified in the rhizomes of Sinomenium acutum in 2014. 40 Berbithine (26) and 6-( [1,3]dioxolo[4,5-g]isoquinoline-5-carbonyl)-2,3-dimethoxybenzoic acid methyl ester (27) were isolated from the rhizome of Coptis chinensis.…”

Section: 4′-oo-didemethylancistrocladinium a (A/b)mentioning

confidence: 99%

“…40 Berbithine (26) and 6-( [1,3]dioxolo[4,5-g]isoquinoline-5-carbonyl)-2,3-dimethoxybenzoic acid methyl ester (27) were isolated from the rhizome of Coptis chinensis. 41 In 2018, several benzylisoquinoline alkaloids, including 24, 25, norcolaurine-4′-O-glucoside (28), N-methylhigenamine (29), norcoclaurine-6-O-glucoside (30), norcoclaurine (31), argemexirine (32), lotusine (33), isococlaurine (34), armepavine (35), 6-demethy-4′-methyl-N-methylcoclaurine (36), coclaurine (37), N-nor-O-methylarmepavine (38), isococlaurine-5′-Opentoside (39), and coclaurine-5′-O-pentoside (40) were identified from P. nelumbinis through UPLC-ESI-QTOF-MS. 30 Subsequently, juzirine (41) was identified from the aerial parts of Leonurus japonicus. 42 (R)-(+)-1-Benzyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline (42) from P. oleracea showed anti-inflammatory and β2-adrenergic receptor agonist activities.…”

Section: 4′-oo-didemethylancistrocladinium a (A/b)mentioning

confidence: 99%

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Biologically active isoquinoline alkaloids covering 2014–2018

Shang

Yang

Morris‐Natschke

et al. 2020

Medicinal Research Reviews

145

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Isoquinoline alkaloids, an important class of N-based heterocyclic compounds, have attracted considerable attention from researchers worldwide since the early 19th century. Over the past 200 years, many compounds from this class were isolated, and most of them and their analogs possess various bioactivities. In this review, we survey the updated literature on bioactive alkaloids and highlight research achievements of this alkaloid class during the period of 2014-2018. We reviewed over 400 molecules with a broad range of bioactivities, including antitumor, antidiabetic and its complications, antibacterial, antifungal, antiviral, antiparasitic, insecticidal, anti-inflammatory, antioxidant, neuroprotective, and other activities. This review should provide new indications or directions for the discovery of new and better drugs from the original naturally occurring isoquinoline alkaloids.

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“…6−25 These chemical components show diverse bioactivities, including nitric oxide inhibitory activity, 7 glucose transport inhibitory effects, 8 cytotoxicity, 8−11 antimicrobial activity, 11 and dengue virus NS5 polymerase inhibitory properties, 12 as well as anti-inflammatory, 13 antioxidant, antiplasmodial, 25 and cholinesterase inhibitory activities. 26 Among over 350 species in the genus Cryptocarya , phytochemical research on C . laevigata has not been reported, except for one article published in 1978.…”

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confidence: 99%

(−)-Neocaryachine, an Antiproliferative Pavine Alkaloid from Cryptocarya laevigata, Induces DNA Double-Strand Breaks

et al. 2017

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Twelve benzylisoquinoline alkaloids, including pavine and phenanthroindolizidine types, were isolated from a MeOH/CH2Cl2 extract of Cryptocarya laevigata (stem bark) through bioactivity-guided fractionation for antitumor effects. Selected compounds were evaluated for antiproliferative activity against five human tumor cell lines, including a multidrug-resistant subline. Since more common 2,3,8,9-tetrasubstituted pavine alkaloids, such as crychine (3), exhibit very mild or no cytotoxicity, this compound type has not been well investigated for antitumor activity. Thus, this report is the first discovery of a 7-hydroxylated pavine alkaloid, (−)-neocaryachine (1), to demonstrate strong antiproliferative activity, with IC50 values of 0.06 to 0.41 µM against five tested tumor cell lines, including an MDR subline. Further mechanism of action studies revealed that 1 impacts the cellular S-phase by inducing DNA double-strand breaks.

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Cholinesterase inhibitory activity of isoquinoline alkaloids from three Cryptocarya species (Lauraceae)

Cited by 49 publications

References 26 publications

Chemical Constituents from Solenostemma argel and their Cholinesterase Inhibitory Activity

Chemical Constituents from Solenostemma argel and their Cholinesterase Inhibitory Activity

Biologically active isoquinoline alkaloids covering 2014–2018

(−)-Neocaryachine, an Antiproliferative Pavine Alkaloid from Cryptocarya laevigata, Induces DNA Double-Strand Breaks

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