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Arborine, a larval growth inhibitor from Glycoslnis pentaphylla
... Earlier, Chatterjee and Majumdar (1953) reported the chemical constitution and synthesis of Glycosin alkaloid from Glycosmis pentaphylla . After that, Glycosin was found to have a growth inhibitory effect on the larvae of Drosophila melanogaster ( Ahmad et al. 1996 ). ...
... Another doublet of doublet at 8.35 ( J = 7.8 and 1.3 Hz) was assigned to the deshielded fragrant proton in the peri-position to the carbonyl group of a quinazoline system. A complete assignment for the 1 H NMR chemical shifts of Glycosin was made by comparison with the data of similar compounds reported by Ahmad et al. (1996) . The 13 C NMR spectrum showed the presence of 16 carbons with four quaternary carbons at 168.0, 162.1, 149.5 and 119.1. ...
... The range likewise demonstrated the frequency of one methylene carbon which was confirmed. Complete assignments for the 13 C NMR compound arrangements of Glycosin were made by comparison with the data of similar compounds for both the heterocyclic and the isolated phenyl part of the molecule ( Chatterjee and Majumdar 1953;Dreyer and Brenner 1980;Ahmad et al. 1996 ). ...
... GP3-3 was assigned to 2,3-dimethoxy-1-hydroxy-10-methylacridone or arborinine (Figure 2a) (Mawardi et al., 2010), with characteristics identical to that of previously reported from Ruta angustifolia (Mohd Kamal et al., 2018). GP6-3 was confirmed as 2-benzyl-1-methylquinazolin-4(1H)-one with the trivial name arborine (Figure 2b) (Farediah et al., 1996). ...
Glycosmis pentaphylla (Retz.) DC., locally known as nerapan, has long been used in Asian countries as a traditional remedy for ailments attributed to microbial infections. This study aims to isolate antimicrobial alkaloids from G. pentaphylla, to determine their combination effects with selected antimicrobial agents and to screen for their photoactivated enzymatic restriction inhibitory activity. Bioautography-guided isolation of antimicrobial alkaloids was performed by using column chromatography with Staphylococcus aureus, Escherichia coli, and Candida albicans as the indicator microbes. The antimicrobial effects of the alkaloids combined with selected
antimicrobial agents, namely, ciprofloxacin, erythromycin, vancomycin, and ketoconazole, were determined by using a checkerboard assay. Photoactivated enzymatic restriction inhibitory activity was assessed by using agarose gel electrophoresis. Two antimicrobial active alkaloids were isolated and identified as arborinine and arborine. The antimicrobial activity of arborinine and arborine was determined to be in the range of 250 μg/ml and 1000 μg/ml. Partial synergy was observed for all arborine-antibiotics and arborinine-ketoconazole interactions against S. aureus and C. albicans, respectively. Arborine was relatively the strongest photoactivated enzymatic restriction inhibitor, particularly against EcoRI, PstI, and SalI. The results obtained are promising and encourage further research on the alkaloids as potential antimicrobial-enhancing agents.
The present article is a systematic and constructive review of the traditional medicinal uses, chemistry, pharmacology, toxicology, and formulation aspects of Glycosmis species. The genus Glycosmis comprise 51 accepted species broadly distributed in Australia, China, India, and South-East Asia. Traditionally, Glycosmis species are used in folk medicines to treat cancer, anaemia, rheumatism, fever, cough, liver-related problems, skin ailments, intestinal worm infections, wounds, and facial inflammation. This review aims to provide readers with the latest information highlighting chemical constituents isolated from the Glycosmis species, plant parts utilized for their isolation and their pharmacological activities. So far, 307 chemical constituents have been isolated and characterized from different species of the genus Glycosmis; among these constituents, alkaloids, flavonoids, terpenoids, phenolics, and sulphur-containing amides are the major bioactive compounds. Modern pharmacological studies have shown that the crude extracts and compounds isolated from this genus exhibit a broad spectrum of biological activities like anticancer, antimicrobial, anti-inflammatory, antipyretic, antidiabetic, antioxidant, larvicidal, insecticidal, hepatoprotective, wound healing, antiviral, antidiarrheal, and anxiolytic. The carbazole and acridone alkaloids from this genus have shown potential anticancer activity in various in vitro and in vivo studies. Rare scaffolds like dimeric carbazoles, dimeric acridone alkaloids, flavanocoumarins and sulphur-containing amides from this genus need further exploration for their potential bioactivity. This article also briefs about the toxicological screening and discusses various polyherbal and nano formulation aspects of Glycosmis species. Most of the pharmacological studies reported from this genus were carried out in vitro. An in-depth in vivo and toxicology evaluation of the crude extracts and isolated specialized compounds is required to explore the full therapeutic potential of this genus.
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