Toward the Synthesis and Pharmacological Screening of a Natural Cycloheptapeptide of Plant Origin

Dahiya, Rajiv; Singh, Sunil

doi:10.1177/1934578x1701200318

Cited by 5 publications

(3 citation statements)

References 16 publications

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“…The experimental details of the biological activity studies are described in our earlier reports [ 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 ]. Further, in order to describe the intermolecular forces of drug receptor interaction as well as the transport and distribution of drugs in a quantitative manner, various steric and the lipophilicity parameters need to be calculated for the synthesized linear and cyclic tetracyclopeptides ( 3 , 4 ).…”

Section: Methodsmentioning

confidence: 99%

Toward the Synthesis and Improved Biopotential of an N-methylated Analog of a Proline-Rich Cyclic Tetrapeptide from Marine Bacteria

et al. 2018

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An N-methylated analog of a marine bacteria-derived natural proline-rich tetracyclopeptide was synthesized by coupling the deprotected dipeptide fragments Boc-l-prolyl-l-N-methylleucine-OH and l-prolyl-l-N-methylphenylalanine-OMe. A coupling reaction was accomplished utilizing N,N′-Dicyclohexylcarbodidimde (DCC) and 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC·HCl) as coupling agents and Triethylamine (TEA) or N-methylmorpholine (NMM) as the base in the presence of the racemization suppressing agent. This was followed by the cyclization of the linear tetrapeptide fragment under alkaline conditions. The structure of the synthesized cyclooligopeptide was confirmed using quantitative elemental analysis, FTIR (Fourier-transform infrared spectroscopy), 1H NMR (Nuclear magnetic resonance spectroscopy), 13C NMR, and mass spectrometry. From the bioactivity results, it was clear that the newly synthesized proline-rich tetracyclopeptide exhibited better anthelmintic potential against Megascoplex konkanensis, Pontoscotex corethruses, and Eudrilus eugeniae at a concentration of 2 mg/mL as well as improved antifungal activity against pathogenic dermatophytes Trichophyton mentagrophytes and Microsporum audouinii at a concentration of 6 μg/mL, as compared to non-methylated tetracyclopeptide. Moreover, N-methylated tetracyclopeptide displayed significant activity against pathogenic Candida albicans.

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Section: Methodsmentioning

confidence: 99%

Toward the Synthesis and Improved Biopotential of an N-methylated Analog of a Proline-Rich Cyclic Tetrapeptide from Marine Bacteria

et al. 2018

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“…The experimental details of the biological activity studies are described in our previously published reports [ 51 , 52 , 53 , 54 , 55 ]. As per the International Union of Pure and Applied Chemistry (IUPAC) rules, the N -methylated cycloheptapeptide 8 can be named as “3,15-Dibenzyl-9-( sec -butyl)-12-(4-hydroxybenzyl)-6-isobutyl-2,11,17-trimethylperhydropyrrolo [1,2- a ][1,4,7,10,13,16,19]heptaazacyclohenicosine-1,4,7,10,13,16,19-heptaone”.…”

Section: Methodsmentioning

confidence: 99%

Total Synthesis and Pharmacological Investigation of Cordyheptapeptide A

et al. 2017

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The present investigation reports the synthesis of a phenylalanine-rich N-methylated cyclopeptide, cordyheptapeptide A (8), previously isolated from the insect pathogenic fungus Cordyceps sp. BCC 1788, accomplished through the coupling of N-methylated tetrapeptide and tripeptide fragments followed by cyclization of the linear heptapeptide unit. Structure elucidation of the newly synthesized cyclopolypeptide was performed by means of FT-IR, 1H-NMR, 13C-NMR, and fast atom bombardment mass spectrometry (FABMS), and screened for its antibacterial, antidermatophytic, and cytotoxic potential. According to the antimicrobial activity results, the newly synthesized N-Methylated cyclopeptide exhibited potent antibacterial activity against Gram-negative bacteria Pseudomonas aeruginosa and Klebsiella pneumoniae and antifungal activity against dermatophytes Trichophyton mentagrophytes and Microsporum audouinii at a concentration of 6 μg/mL, in comparison to the reference drugs, gatifloxacin and griseofulvin. In addition, cyclopolypeptide 8 displayed suitable levels of cytotoxicity against Dalton’s lymphoma ascites (DLA) and Ehrlich’s ascites carcinoma (EAC) cell lines.

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“…The incidence of toxicity and dependence has limited the therapeutic usefulness of these drugs (Desai et al 2009). Herbal formulations and medicinal plants have been in use for many years not only in Asian countries but also globally for human well-being as well as reported in literature for their biopotential (Dahiya et Dahiya and Singh, 2017a;2017b;2017c). The herbal formulations claimed to enhance physical endurance, mental functions ISSN: 2249-6041 (Print); ISSN: 2249-9245 (Online) and non-specific resistance of the body and have been termed as adaptogens (Desai et al 2009).…”

Section: Introductionmentioning

confidence: 99%

Isolation of Beta-Asarone and Forskolin and Their in Vivo Activity Against Stress

Tiwari¹

2019

BPR

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Stress is known to result in impairment of learning and memory and precipitate several affective disorders including depression and anxiety. Drugs of natural origin are known to possess several effects on the central nervous system and are emerging as promising alternative. Beta-asarone is one of the main bioactive constituents in traditional Chinese medicine Acorus calamus. Forskolin, a labdane diterpene is the main active ingredient in the ayurvedic herb Coleus forskohlii (Labatiae) that has been used in India since ancient times. The present study was designed to evaluate the antistress activity of the isolated compounds. The compounds were isolated by normal phase column chromatography and the structures were elucidated by spectroscopic methods. Beta-asarone and Forskolin were tested using elevated plus maze (EPM) model and forced swimming test (FST) respectively in Swiss albino mice. Albino mice were treated with different doses of the extracts (50, 100 and 200 mg/kg orally) and behavior was observed on the EPM and FST. Results showed that isolated compounds Beta-asarone and Forskolin at the dose of 100 mg/kg markedly increased the average time spent in the open arms in EPM and the same compounds showed a significant decrease in the time spent immobile by mice in FST. These results provide support for the potential antistress activity.

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Toward the Synthesis and Pharmacological Screening of a Natural Cycloheptapeptide of Plant Origin

Cited by 5 publications

References 16 publications

Toward the Synthesis and Improved Biopotential of an N-methylated Analog of a Proline-Rich Cyclic Tetrapeptide from Marine Bacteria

Toward the Synthesis and Improved Biopotential of an N-methylated Analog of a Proline-Rich Cyclic Tetrapeptide from Marine Bacteria

Total Synthesis and Pharmacological Investigation of Cordyheptapeptide A

Isolation of Beta-Asarone and Forskolin and Their in Vivo Activity Against Stress

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