Three New Cholinesterase-Inhibiting cis-Clerodane Diterpenoids from Otostegia limbata

Ahmad, Viqar Uddin; Khan, Afsar; Farooq, Umar; Kousar, Farzana; Khan, Saleha Suleman; Nawaz, Syed Junaid; Abbasi, Muhammad Athar; Choudhary, M. Iqbal

doi:10.1248/cpb.53.378

Cited by 35 publications

(25 citation statements)

References 12 publications

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“…With CO 2 H at the decalin C-4 position and OMe or H, respectively, at the butenolide C-4 position, limbatolides B ( 533 ) and C ( 534 ) from Otostegia limbata inhibited acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes in a concentration-dependent manner with IC 50 values of 47.2, 103.7 and 17.5, 14.2 μM, respectively. 189 Polylongifoliaon B ( 543 ) from Polyalthia longifolia is one of a few type III subtype IIa compounds with an α,β-unsaturated ketone in the decalin ring A. 220 This compound improved the viability of human neuroblastoma cells (SK-N-MC cells) under Aβ-induced neurotoxicity with an IC 50 value of 3.75 μM.…”

Section: Structure Classifications and Sources Of Clerodane Diterpmentioning

confidence: 99%

Clerodane diterpenes: sources, structures, and biological activities

2016

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The clerodane diterpenoids are a widespread class of secondary metabolites and have been found in several hundreds of plant species from various families and in organisms from other taxonomic groups. These substances have attracted interest in recent years due to their notable biological activities, particularly insect antifeedant properties. In addition, the major active clerodanes of Salvia divinorum can be used as novel opioid receptor probes, allowing greater insight into opioid receptor-mediated phenomena, as well as opening additional areas for chemical investigation. This article provides extensive coverage of naturally occurring clerodane diterpenes discovered from 1990 until 2015, and follows up on the 1992 review by Merritt and Ley in this same journal. The distribution, chemotaxonomic significance, chemical structures, and biological activities of clerodane diterpenes are summarized. In the cases where sufficient information is available, structure activity relationship (SAR) correlations and mode of action of active clerodanes have been presented.

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Section: Structure Classifications and Sources Of Clerodane Diterpmentioning

confidence: 99%

Clerodane diterpenes: sources, structures, and biological activities

2016

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“…19 The structures of 3 and 4 were identified by NMR as patagonic acid 14 and (4aR,5S,6R,8aR)-5-[2-(2,5-dihydro-5-methoxy-2-oxofuran-3-yl)ethyl]-3,4,4a,5,6,7,8,8a-octahydro-5,6,8a-trimethylnaphthalene-1-carboxylic acid, respectively, both diterpenes of the clerodane type. 15,24,25 According to the literature 14 on substance 3 the chemical shifts of C-2 is 27.4 and C-7 is 27.2. HMBC spectrum showed a correlation of the signal at 0.85 (d, J 6.7 Hz, CH 3 -17) with the signal at 27.2, being this signal assigned to C-7, and a correlation of the signal at 6.81 (br s H-3) with the signal at 27.4, which was assigned to C-2.…”

Section: Resultsmentioning

confidence: 99%

3',8"-biisokaempferide, a cytotoxic biflavonoid and other chemical constituents of Nanuza plicata (Velloziaceae)

Pinto

Silva

Schindler

et al. 2010

J. Braz. Chem. Soc.

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“…In addition, the thiophene moiety is central in the structure of different antiepileptic drugs (AEDs) such as brotizolam [9], etizolam [10], and tiagabine [11], structures of which are shown in Fig. 1.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, X-ray structure, computational studies, and bioassay of novel compounds combining thiophene and benzimidazole or 1,2,4-triazole moieties

Mabkhot

Al–Showiman

Soliman

et al. 2017

Chemistry Central Journal

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BackgroundDue to their interesting and versatile biological activity, thiophene-containing compounds have attracted the attention of both chemists and medicinal chemists. Some of these compounds have anticancer, antibacterial, antiviral, and antioxidant activity. In addition, the thiophene nucleus has been used in the synthesis of a variety of heterocyclic compounds.ResultsIn the present work, two novel thiophene-containing compounds, 4-phenyl-2-phenylamino-5-(1H-1,3-a,8-triaza-cyclopenta[α]inden-2-yl)-thiophene-3-carboxylic acid ethyl ester (3) and 5-(1H-Imidazo[1,2-b] [1,2,4] triazol-5-yl)-4-phenyl-2-phenylamino-thiophene-3-carboxylic acid ethyl ester (4), have been synthesized by reaction of 5-(2-bromo-acetyl)-4-phenyl-2-phenylaminothiophene-3-carboxylic acid ethyl ester (2) with 2-aminobenzimidazole and 3-amino-1H-1,2,4-triazole in the presence of triethylamine, respectively. Compound 2, on the other hand, was prepared by bromination of 5-acetyl-4-phenyl-2-phenylaminothiophene-3-carboxylic acid ester (1). Structures of the newly prepared compounds were confirmed by different spectroscopic methods such as 1H-NMR, 13C-NMR, and mass spectrometry, as well as by elemental analysis. Furthermore, bromination of compound 1 led to the formation of two constitutional isomers (2a and 2b) that were obtained in an 80:20 ratio. Molecular structures of 2b were confirmed with the aid of X-ray crystallography. Compound 2 was crystallized in the triclinic, P-1, a = 8.8152 (8) Å, b = 10.0958 (9) Å, c = 12.6892 (10) Å, α = 68.549 (5)°, β = 81.667 (5)°, γ = 68.229 (5)°, V = 976.04 (15) Å3, Z = 2, and was found in two isomeric forms regarding the position of the bromine atom. The antibacterial and antifungal activities of the prepared compounds were evaluated.ConclusionsThree new thiophene derivatives were synthesized in good yield. Antimicrobial screening revealed that compound 3 was a promising candidate as a potential antibacterial and antifungal agent; it exhibits remarkable activity against the studied bacterial strains, especially the gram negative bacteria E. coli in addition to some fungi. More work is needed to evaluate its safety and efficacy.

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Three New Cholinesterase-Inhibiting cis-Clerodane Diterpenoids from Otostegia limbata

Cited by 35 publications

References 12 publications

Clerodane diterpenes: sources, structures, and biological activities

Clerodane diterpenes: sources, structures, and biological activities

3',8"-biisokaempferide, a cytotoxic biflavonoid and other chemical constituents of Nanuza plicata (Velloziaceae)

Synthesis, characterization, X-ray structure, computational studies, and bioassay of novel compounds combining thiophene and benzimidazole or 1,2,4-triazole moieties

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